CN111620772A - Production process for preparing isooctanoic acid by using isooctenal as raw material - Google Patents

Production process for preparing isooctanoic acid by using isooctenal as raw material Download PDF

Info

Publication number
CN111620772A
CN111620772A CN202010622761.6A CN202010622761A CN111620772A CN 111620772 A CN111620772 A CN 111620772A CN 202010622761 A CN202010622761 A CN 202010622761A CN 111620772 A CN111620772 A CN 111620772A
Authority
CN
China
Prior art keywords
reactor
aldehyde
isooctenal
micro
reaction
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CN202010622761.6A
Other languages
Chinese (zh)
Other versions
CN111620772B (en
Inventor
楚庆岩
崔课贤
杨彬
刁统贺
周立亮
郭振兴
杨震
孙圆
商芳芳
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Zibo Nalcohol Chemical Co ltd
Shandong University of Technology
Original Assignee
Zibo Nalcohol Chemical Co ltd
Shandong University of Technology
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Zibo Nalcohol Chemical Co ltd, Shandong University of Technology filed Critical Zibo Nalcohol Chemical Co ltd
Priority to CN202010622761.6A priority Critical patent/CN111620772B/en
Publication of CN111620772A publication Critical patent/CN111620772A/en
Application granted granted Critical
Publication of CN111620772B publication Critical patent/CN111620772B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
    • C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
    • C07C51/235—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups of —CHO groups or primary alcohol groups
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/0093—Microreactors, e.g. miniaturised or microfabricated reactors
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention belongs to the technical field of fine chemical engineering, and particularly relates to a production process for preparing isooctanoic acid by taking isooctenal as a raw material. In a micro-bubble reactor, carrying out selective hydrogenation reaction by taking isooctenal as a raw material under the action of a nano particle hydrogenation catalyst to prepare isooctanal; adding the obtained isooctaldehyde into an oxidation reactor, blowing micro bubbles through an air generator, and reacting the isooctaldehyde with oxygen in the micro bubbles to obtain the isooctanoic acid. The production process has low cost, does not use high-corrosivity materials such as alkali, sulfuric acid, potassium permanganate and the like, does not generate environmental pollutants in the whole production process, and has strong environmental friendliness and good atom economy.

Description

Production process for preparing isooctanoic acid by using isooctenal as raw material
Technical Field
The invention belongs to the technical field of fine chemical engineering, and particularly relates to a production process for preparing isooctanoic acid by taking isooctenal as a raw material.
Background
Isooctanoic acid, also known as 2-ethylhexanoic acid, is a colorless, slightly odorous liquid, slightly soluble in cold water, soluble in hot water and diethyl ether, slightly soluble in ethanol, is an important fine chemical, and is widely used in the fields of coatings, inks, plastics, medicines, pesticides, national defense and the like. Isooctanoic acid is an alternative chemical to naphthenic acid, mostly used for the production of metal salts of isooctanoic acid. In general, isooctanoate has better performance than naphthenate and is more widely used.
At present, raw materials for synthesizing isooctanoic acid mainly comprise isooctenal, isooctylaldehyde and isooctyl alcohol. Isooctanoic acid is mainly used for preparing various metal salts as drier for coatings and paints, and its esters can be used as raw materials of plasticizer or carbenicillin. 2-ethyl caproic acid is mostly converted into salts of zirconium, cobalt, molybdenum, zinc and the like, and is used as a paint drier and a heat stabilizer of polyvinyl chloride plastics; tin salt is used as an additive of the plastic pipe; barium salt and cadmium salt are used for plastic rolling products and stabilizers, 2-ethylhexanoic acid and esters thereof are also used in the fields of medicines, bactericides, metal lubricants, cosmetics and the like, and glyceride thereof is an excellent plasticizer. 2-ethylhexanoic acid is a starting material for the pharmaceutical carbenicillin, used in the synthesis of many dyes, fragrances, and it is also an intermediate for paint and coating driers, used as an alkyd modifier, and the peroxide produced as a catalyst for polymerization reactions (e.g., PE), lubricating oil esters, and PVC stabilizers.
There are three main methods for the synthesis of 2-ethylhexanoic acid: a 2-ethylhexanol oxidation method; (xii) 2-ethylhexenal oxidation; ③ 2-ethyl hexanol dehydrogenation esterification method. The 2-ethylhexanol oxidation method is mainly characterized in that 2-ethylhexanol reacts with potassium permanganate in an alkaline or acidic medium to generate 2-potassium ethylhexanoate, and the potassium ethylhexanoate is acidified by concentrated sulfuric acid after being cooled to room temperature; the 2-ethylhexanol dehydrogenation esterification method is to use 2-ethylhexanol and sodium hydroxide to carry out oxidative dehydrogenation reaction to prepare 2-ethylhexanoic acid sodium, and then to neutralize with sulfuric acid to obtain isooctanoic acid. The two methods are both traditional processes, the scale of the device is small, and the three wastes are serious.
Chinese patent CN1817845A discloses a new process for preparing isooctanoic acid by a composite catalytic method, which comprises the steps of filling isooctanol and sodium hydroxide aqueous solution into a reaction kettle to ensure that the molar ratio of alcohol to alkali is 1.2-1.5; then adding a composite catalyst which is formed by combining 0.8-1.2 unit mass of calcium oxide, 0.6-0.9 unit mass of vanadium pentoxide and 0.1-0.4 unit mass of rare earth oxide under stirring; stirring and gradually heating to 240-280 ℃ to finish the alcohol-base oxidation reaction for 1.8-2.2 hours; hydrogen gas is discharged; then cooling the reaction materials, adding 5-10% of water for dilution, and filtering out the solid composite catalyst; then adding H with the content of 30-40 percent2SO4The pH value of the materials is adjusted to 3 by the water solution, the materials are stirred for acidification reaction for 30 to 40 minutes, and the materials are kept stand for layering and are drained of a water layer; then washing the material with water; and (5) carrying out reduced pressure dehydration to prepare an isooctanoic acid product. The patent belongs to a process for preparing isooctanoic acid by a 2-ethylhexanol oxidation method, the scale of a device is small, sodium hydroxide and sulfuric acid are required in the process, the corrosion to equipment is serious, a large amount of environmental pollutants are generated, and the problem of three wastes is serious.
Chinese patent CN107930647A discloses a catalyst, a preparation method thereof and a preparation method of 2-ethylhexanal. The preparation method of the 2-ethylhexanal comprises the following steps: heating the isooctene aldehyde feed to 180-220 ℃ to gasify the isooctene aldehyde, and introducing hydrogen into the isooctene aldehyde to obtain a mixed gas of the gasified isooctene aldehyde and the hydrogen; and the mixed gas is contacted with a catalyst in the hydrogenation reactor to carry out selective hydrogenation reaction, so as to obtain the mixed gas flow rich in 2-ethylhexanal. The patent has high hydrogenation temperature and large energy consumption, only obtains 2-ethylhexanal, and does not disclose the production process of the isooctanoic acid.
Chinese patent CN111054437A discloses a catalyst for preparing isooctylaldehyde by selective hydrogenation of isooctylaldehyde, a preparation method and application thereof. The catalyst is a metal-polymer composite catalyst and comprises a polyacid crosslinked polymer matrix and a metal active component, wherein the polyacid crosslinked polymer matrix is obtained by the coordination crosslinking action of the polymer matrix with a polyacid crosslinking agent. The method for preparing isooctylaldehyde comprises the following steps: in the presence of hydrogen, under the conditions of reaction temperature of 50-130 ℃ and reaction pressure of 1.0-5.0MPa, in a high-pressure kettle reactor, isooctyl aldehyde is obtained under the catalytic action of the metal-polymer composite catalyst. The catalyst of the patent requires sulfuric acid, phosphoric acid, peroxymolybdic acid and chloroplatinic acid during preparation, and three wastes are generated.
At present, the market of isooctanoic acid is in short supply, most of isooctanoic acid is produced by an alcohol method in China, and the device scale is small. The isooctanoic acid produced by hydrogenation and oxidation of isooctenal has the advantages of low consumption, little pollution, stable product quality, etc. Therefore, a production process for preparing isooctanoic acid by using isooctenal as a raw material by utilizing the advantages of the isooctenal is needed to meet the increasing demand of isooctanoic acid.
Disclosure of Invention
The invention aims to provide a production process for preparing isooctanoic acid by using isooctenal as a raw material, which has low production cost, does not use high-corrosive materials such as alkali, sulfuric acid, potassium permanganate and the like, and does not generate environmental pollutants in the whole production process.
The technical scheme adopted by the invention for solving the technical problems is as follows:
the production process for preparing isooctanoic acid by using isooctenal as a raw material comprises the following steps:
(1) in a micro-bubble reactor, carrying out selective hydrogenation reaction by taking isooctenal as a raw material under the action of a nano particle hydrogenation catalyst to prepare isooctanal;
(2) adding the isooctyl aldehyde obtained in the step (1) into an oxidation reactor, blowing micro bubbles through an air generator, and reacting the isooctyl aldehyde with oxygen in the micro bubbles to obtain the isooctanoic acid.
Wherein:
in the step (1), the nanoparticle hydrogenation catalyst is nanoparticles of gold, palladium, platinum, nickel, vanadium, molybdenum, manganese or oxides thereof; the molar ratio of the nanoparticle hydrogenation catalyst to the amount of isooctenal fed per hour is 0.00008 to 0.01:1, preferably 0.0001 to 0.009: 1.
In the step (1), the temperature of the selective hydrogenation reaction is 30-170 ℃, preferably 80-160 ℃; the pressure is 0.1-10MPa, preferably 0.2-8 MPa.
In the step (1), the space velocity of the isooctene aldehyde in the selective hydrogenation reaction process is 0.005-1h-1Preferably 0.01 to 0.9h-1(ii) a The feed molar ratio of isooctenal to hydrogen is 1:1 to 40, preferably 1:2 to 30.
In the step (2), the isooctyl aldehyde enters an oxidation reactor for reaction, and the space velocity of the isooctyl aldehyde is 0.005-1h-1Preferably 0.01 to 0.9h-1(ii) a The reaction temperature of the isooctyl aldehyde in the oxidation reactor is 20-150 ℃, and the preferred temperature is 30-120 ℃; the feed molar ratio of isooctylaldehyde to oxygen is from 1:1 to 40, preferably from 1:2 to 30.
The production process for preparing isooctanoic acid by using isooctenal as a raw material comprises the following steps:
(1) in a micro-bubble reactor, carrying out selective hydrogenation reaction by taking isooctenal as a raw material under the action of a nano particle hydrogenation catalyst to prepare isooctanal;
(2) mixing the isooctyl aldehyde obtained in the step (1) with an oxidation catalyst, adding the mixture into an oxidation reactor, blowing micro bubbles through an air generator, and reacting the isooctyl aldehyde with oxygen in the micro bubbles to obtain isooctanoic acid; the oxidation catalyst is recovered with the mother liquor after being filtered by a filter at an isooctanoic acid outlet for recycling.
Wherein:
in the step (2), the oxidation catalyst is cobalt acetate, molybdenum acetate, silver acetate, manganese isooctanoate, cobalt isooctanoate, molybdenum isooctanoate, silver isooctanoate, manganese dioxide, silver oxide, vanadium acetylacetonate, molybdenum trioxide, vanadium pentoxide, aluminum oxide, ferric chloride or palladium oxide;
the molar ratio of oxidation catalyst to isooctylaldehyde feed per hour is from 0 to 0.1:1, preferably from 0 to 0.09: 1.
Preferably, the production process for preparing isooctanoic acid by using isooctenal as a raw material comprises the following steps:
(1) the microbubble reactor comprises a gas phase inlet, a liquid phase inlet, a microbubble tube and a reaction zone, wherein the microbubble tube, the gas phase inlet and the liquid phase inlet are positioned at the upper part of the reaction zone, an annular space channel is formed between the microbubble tube and the tube wall of the microbubble reactor, the liquid phase inlet is connected with the annular space channel, and the gas phase inlet is connected with the microbubble tube; a nano particle hydrogenation catalyst is arranged inside the reaction zone, and a heating medium channel is arranged outside the reaction zone;
hydrogen enters the micro bubble tube from the gas phase inlet, isooctene aldehyde enters an annular channel formed between the micro bubble tube and the tube wall of the micro bubble reactor from the liquid phase inlet, the hydrogen penetrates through the micro bubble tube and carries out selective hydrogenation reaction with isooctene aldehyde under the action of a nano particle hydrogenation catalyst in a reaction zone to prepare isooctene aldehyde, and the isooctene aldehyde flows out from the bottom of the micro bubble reactor;
(2) an air generator is arranged at the bottom of the oxidation reactor, an air outlet is arranged at the top of the oxidation reactor, an isooctyl aldehyde inlet is arranged on one side surface of the oxidation reactor, an isooctanoic acid outlet is arranged on the other side surface of the oxidation reactor, the isooctanoic acid outlet is higher than the isooctyl aldehyde inlet, and a filter is arranged at the isooctanoic acid outlet; an insulating layer is arranged around the oxidation reactor;
and (2) enabling the isooctaldehyde obtained in the step (1) to enter an oxidation reactor from an isooctaldehyde inlet, blowing micro-bubbles through an air generator, enabling the isooctaldehyde to react with oxygen in the micro-bubbles to obtain isooctanoic acid, and enabling the isooctanoic acid to flow out of the oxidation reactor from an isooctanoic acid outlet.
Wherein: in the step (1), the microbubble reactor is an annular space flow fixed bed reactor; the width of the annular gap channel is 1-5mm, preferably 2-3 mm; the micro bubble tube is made of a ceramic membrane, and the pore size of the ceramic membrane is 5-100nm, preferably 5-10 nm; the length of the ceramic membrane is 5-100cm, preferably 20-30 cm. The material of the micro bubble tube body can also be a metal film.
In the step (2), the air blowing pipes of the air generator are 1-10 groups, preferably 5-8 groups; the height of the air blast pipe is 5-100cm, preferably 50-60 cm; the width between the air blowing tubes is 5-100cm, preferably 30-50 cm.
And (2) introducing a heating medium into the heat-insulating layer for heat insulation, wherein the filter is a membrane filter.
The invention has the following beneficial effects:
the invention provides a production process for preparing isooctanoic acid by using isooctenal as a raw material, which is characterized in that the isooctenal is used as the raw material and is catalyzed by a nano particle hydrogenation catalyst in a microbubble reactor to carry out selective hydrogenation at a certain pressure, temperature and airspeed to prepare the isooctanal, and the obtained isooctanal can directly enter an oxidation system for oxidation reaction without purification.
In the microbubble reactor, hydrogen enters a microbubble tube and is dispersed into a large number of microbubbles to enter a liquid phase, the raw materials of isooctene aldehyde and hydrogen can carry out mass transfer and heat transfer under the micro-nano condition, and then catalytic hydrogenation is carried out on a nano particle hydrogenation catalyst micro interface, the reaction efficiency is high, the reaction selectivity is good, the reaction selectivity is not less than 95%, and the conversion rate is not less than 97%.
The obtained isooctyl aldehyde is added into an oxidation reactor, the periphery of the oxidation reactor is wrapped by a heating medium to ensure that the reaction is carried out at constant temperature, an air generator can generate a large amount of controllable micro bubbles, the control is carried out in real time according to the reaction condition, an air outlet is arranged at the upper part of the reactor to ensure that redundant gas is discharged, isooctyl aldehyde and an oxidation catalyst are uniformly mixed and then enter the oxidation reactor to be oxidized into isooctyl acid by oxygen in the micro bubbles, the product isooctyl acid is discharged at an outlet, the oxidation catalyst is recovered with mother liquor after the isooctyl acid is filtered by a filter at the outlet of the isooctyl acid and is recycled, the selectivity of the reaction is more than or equal.
The production process has low cost, does not use high-corrosivity materials such as alkali, sulfuric acid, potassium permanganate and the like, does not generate environmental pollutants in the whole production process, and has strong environmental friendliness and good atom economy.
Drawings
FIG. 1 is a schematic diagram of a microbubble reactor;
FIG. 2 is a schematic diagram of the structure of an oxidation reactor;
wherein: 1. a gas phase inlet; 2. a liquid phase inlet; 3. a micro bubble tube; 4. a nanoparticle hydrogenation catalyst; 5. a heating medium passage; 6. a reaction zone; 7. an air outlet; 8. an iso-octanal inlet; 9. an air generator; 10. a heat-insulating layer; 11. an isooctanoic acid outlet; 12. and (3) a filter.
Detailed Description
The present invention is further described below with reference to examples.
As shown in fig. 1 and 2, the microbubble reactor according to the present invention includes a gas phase inlet 1, a liquid phase inlet 2, a microbubble tube 3, and a reaction zone 6, wherein the microbubble tube 3, the gas phase inlet 1, and the liquid phase inlet 2 are located at an upper portion of the reaction zone 6, an annular gap channel is formed between the microbubble tube 3 and a tube wall of the microbubble reactor, the liquid phase inlet 2 is connected to the annular gap channel, and the gas phase inlet 1 is connected to the microbubble tube 3; a nano particle hydrogenation catalyst 4 is arranged inside the reaction zone 6, and a heating medium channel 5 is arranged outside the reaction zone 6;
the bottom of the oxidation reactor is provided with an air generator 9, the top of the oxidation reactor is provided with an air outlet 7, one side surface of the oxidation reactor is provided with an isooctyl aldehyde inlet 8, the other side surface of the oxidation reactor is provided with an isooctyl acid outlet 11, the isooctyl acid outlet 11 is higher than the isooctyl aldehyde inlet 8, and a filter 12 is arranged at the isooctyl acid outlet 11; an insulating layer 10 is also arranged around the oxidation reactor.
The microbubble reactor is an annular space flow fixed bed reactor; the width of the annular gap channel is 1-5 mm; the micro bubble tube 3 is made of a ceramic membrane, the pore of the ceramic membrane is 5-100nm, and the length of the ceramic membrane is 5-100 cm.
The air generator has 1-10 groups of air blowing pipes, the height of the air blowing pipes is 5-100cm, and the width between the air blowing pipes is 5-100 cm.
Hydrogen enters a micro bubble tube 3 from a gas phase inlet 1, isooctene aldehyde enters an annular space channel formed between the micro bubble tube 3 and the tube wall of a micro bubble reactor from a liquid phase inlet 2, the hydrogen penetrates through the micro bubble tube 3 and carries out selective hydrogenation reaction with the isooctene aldehyde under the action of a nano particle hydrogenation catalyst 4 in a reaction zone 6 to prepare the isooctene aldehyde, and the isooctene aldehyde flows out from the bottom of the micro bubble reactor; the obtained isooctaldehyde enters the oxidation reactor from an isooctaldehyde inlet 8, micro-bubbles are blown in through an air generator 9, the isooctaldehyde reacts with oxygen in the micro-bubbles to prepare isooctanoic acid, and the isooctanoic acid flows out of the oxidation reactor from an isooctanoic acid outlet 11.
Example 1
The isooctene aldehyde enters a microbubble reactor, and under the pressure of 1MPa and the temperature of 130 ℃ and the action of a palladium nanoparticle hydrogenation catalyst, the isooctene aldehyde and hydrogen undergo a selective hydrogenation reaction to produce the isooctene aldehyde, wherein the selectivity of the reaction is 99.5 percent, and the conversion rate is 100 percent. Wherein the space velocity of the raw material isooctenal in the reactor is 0.1h-1The feeding molar ratio of raw materials of isooctene aldehyde and hydrogen is 1:6, the molar ratio of the consumption of a palladium nanoparticle hydrogenation catalyst to the feeding amount of isooctene aldehyde per hour is 0.001:1, a microbubble reactor is an annular space flow fixed bed reactor, the width of an annular space channel is 3mm, the pore space of a ceramic membrane is 10nm, and the length of the ceramic membrane is 25 cm;
the obtained isooctyl aldehyde enters an oxidation reactor, and is oxidized into isooctyl acid by oxygen in micro-bubbles at the temperature of 70 ℃ through micro-bubbles blown by an air generator; the space velocity of the isooctyl aldehyde in the reactor is 0.1h-1The feeding molar ratio of isooctylaldehyde to oxygen is 1:6, the number of air blowing pipes of an air generator in the oxidation reactor is 8, the height of the air blowing pipes is 60cm, the width between the air blowing pipes is 35cm, the selectivity of the reaction is 98.0%, and the conversion rate is 100%.
Example 2
The isooctenal enters a microbubble reactor, and is subjected to selective hydrogenation reaction with hydrogen under the pressure of 0.3MPa and the temperature of 130 ℃ and under the action of a palladium nanoparticle hydrogenation catalyst to produce the isooctenal, the selectivity of the reaction is 96.3 percent, and the conversion rate is 98 percent. Wherein the space velocity of the raw material isooctenal in the reactor is 0.1h-1The feeding molar ratio of raw materials of isooctene aldehyde and hydrogen is 1:6, the molar ratio of the consumption of a palladium nanoparticle hydrogenation catalyst to the feeding amount of isooctene aldehyde per hour is 0.001:1, a microbubble reactor is an annular space flow fixed bed reactor, the width of an annular space channel is 3mm, the pore space of a ceramic membrane is 10nm, and the length of the ceramic membrane is 25 cm;
feeding the obtained isooctylaldehyde into an oxidation reactor, and passing through a reactorUnder the temperature of 70 ℃, the isooctyl aldehyde is oxidized into isooctanoic acid by oxygen in the microbubbles by the microbubbles blown by the gas generator; the space velocity of the isooctyl aldehyde in the reactor is 0.1h-1The feeding molar ratio of isooctylaldehyde to oxygen is 1:6, the number of air blowing pipes of an air generator in the oxidation reactor is 8, the height of the air blowing pipes is 60cm, the width between the air blowing pipes is 35cm, the selectivity of the reaction is 98.0%, and the conversion rate is 100%.
Example 3
The isooctene aldehyde enters a microbubble reactor, and under the pressure of 5MPa and the temperature of 130 ℃ and the action of a palladium nanoparticle hydrogenation catalyst, the isooctene aldehyde and hydrogen undergo a selective hydrogenation reaction to produce the isooctene aldehyde, wherein the selectivity of the reaction is 98.5 percent, and the conversion rate is 99 percent. Wherein the space velocity of the raw material isooctenal in the reactor is 0.1h-1The feeding molar ratio of raw materials of isooctene aldehyde and hydrogen is 1:6, the molar ratio of the consumption of a palladium nanoparticle hydrogenation catalyst to the feeding amount of isooctene aldehyde per hour is 0.001:1, a microbubble reactor is an annular space flow fixed bed reactor, the width of an annular space channel is 3mm, the pore space of a ceramic membrane is 10nm, and the length of the ceramic membrane is 25 cm;
the obtained isooctyl aldehyde enters an oxidation reactor, and is oxidized into isooctyl acid by oxygen in micro-bubbles at the temperature of 70 ℃ through micro-bubbles blown by an air generator; the space velocity of the isooctyl aldehyde in the reactor is 0.1h-1The feeding molar ratio of isooctylaldehyde to oxygen is 1:6, the number of air blowing pipes of an air generator in the oxidation reactor is 8, the height of the air blowing pipes is 60cm, the width between the air blowing pipes is 35cm, the selectivity of the reaction is 98.0%, and the conversion rate is 100%.
Example 4
The isooctene aldehyde enters a microbubble reactor, and under the pressure of 1MPa and the temperature of 90 ℃ and the action of a palladium nanoparticle hydrogenation catalyst, the isooctene aldehyde and hydrogen undergo a selective hydrogenation reaction to produce the isooctene aldehyde, wherein the selectivity of the reaction is 98.6 percent, and the conversion rate is 98 percent. Wherein the space velocity of the raw material isooctenal in the reactor is 0.1h-1The feeding molar ratio of the raw material isooctenal to hydrogen is 1:6, the dosage of the palladium nano particle hydrogenation catalyst is equal toThe mol ratio of the feeding amount of isooctene aldehyde per hour is 0.001:1, the microbubble reactor is an annular space flow fixed bed reactor, the width of an annular space channel is 3mm, the pore space of the ceramic membrane is 10nm, and the length of the ceramic membrane is 25 cm;
the obtained isooctyl aldehyde enters an oxidation reactor, and is oxidized into isooctyl acid by oxygen in micro-bubbles at the temperature of 70 ℃ through micro-bubbles blown by an air generator; the space velocity of the isooctyl aldehyde in the reactor is 0.1h-1The feeding molar ratio of isooctylaldehyde to oxygen is 1:6, the number of air blowing pipes of an air generator in the oxidation reactor is 8, the height of the air blowing pipes is 60cm, the width between the air blowing pipes is 35cm, the selectivity of the reaction is 98.0%, and the conversion rate is 100%.
Example 5
The isooctene aldehyde enters a microbubble reactor, and under the action of a palladium nanoparticle hydrogenation catalyst at the pressure of 1MPa and the temperature of 170 ℃, the isooctene aldehyde and hydrogen undergo a selective hydrogenation reaction to produce the isooctene aldehyde, wherein the selectivity of the reaction is 97.1 percent, and the conversion rate is 99 percent. Wherein the space velocity of the raw material isooctenal in the reactor is 0.1h-1The feeding molar ratio of raw materials of isooctene aldehyde and hydrogen is 1:6, the molar ratio of the consumption of a palladium nanoparticle hydrogenation catalyst to the feeding amount of isooctene aldehyde per hour is 0.001:1, a microbubble reactor is an annular space flow fixed bed reactor, the width of an annular space channel is 3mm, the pore space of a ceramic membrane is 10nm, and the length of the ceramic membrane is 25 cm;
the obtained isooctyl aldehyde enters an oxidation reactor, and is oxidized into isooctyl acid by oxygen in micro-bubbles at the temperature of 70 ℃ through micro-bubbles blown by an air generator; the space velocity of the isooctyl aldehyde in the reactor is 0.1h-1The feeding molar ratio of isooctylaldehyde to oxygen is 1:6, the number of air blowing pipes of an air generator in the oxidation reactor is 8, the height of the air blowing pipes is 60cm, the width between the air blowing pipes is 35cm, the selectivity of the reaction is 98.0%, and the conversion rate is 100%.
Example 6
The isooctenal enters a microbubble reactor, and under the pressure of 1MPa and the temperature of 130 ℃, the nickel nano particle hydrogenation catalyst actsThen, the isooctylaldehyde and hydrogen are subjected to selective hydrogenation reaction to produce isooctylaldehyde, the selectivity of the reaction is 95.9%, and the conversion rate is 98%. Wherein the space velocity of the raw material isooctenal in the reactor is 0.1h-1The feeding molar ratio of raw materials of isooctene aldehyde and hydrogen is 1:6, the molar ratio of the dosage of a nickel nano particle hydrogenation catalyst to the feeding amount of isooctene aldehyde per hour is 0.001:1, a microbubble reactor is an annular space flow fixed bed reactor, the width of an annular space channel is 3mm, the pore space of a ceramic membrane is 10nm, and the length of the ceramic membrane is 25 cm;
the obtained isooctyl aldehyde enters an oxidation reactor, and is oxidized into isooctyl acid by oxygen in micro-bubbles at the temperature of 70 ℃ through micro-bubbles blown by an air generator; the space velocity of the isooctyl aldehyde in the reactor is 0.1h-1The feeding molar ratio of isooctylaldehyde to oxygen is 1:6, the number of air blowing pipes of an air generator in the oxidation reactor is 8, the height of the air blowing pipes is 60cm, the width between the air blowing pipes is 35cm, the selectivity of the reaction is 98.0%, and the conversion rate is 100%.
Example 7
The isooctene aldehyde enters a microbubble reactor, and under the pressure of 1MPa and the temperature of 130 ℃ and the action of a molybdenum nanoparticle hydrogenation catalyst, the isooctene aldehyde and hydrogen undergo a selective hydrogenation reaction to produce the isooctene aldehyde, wherein the selectivity of the reaction is 96.3 percent, and the conversion rate is 97 percent. Wherein the space velocity of the raw material isooctenal in the reactor is 0.1h-1The feeding molar ratio of raw materials of isooctene aldehyde and hydrogen is 1:6, the molar ratio of the consumption of a molybdenum nanoparticle hydrogenation catalyst to the feeding amount of isooctene aldehyde per hour is 0.001:1, a microbubble reactor is an annular space flow fixed bed reactor, the width of an annular space channel is 3mm, the pore space of a ceramic membrane is 10nm, and the length of the ceramic membrane is 25 cm;
the obtained isooctyl aldehyde enters an oxidation reactor, and is oxidized into isooctyl acid by oxygen in micro-bubbles at the temperature of 70 ℃ through micro-bubbles blown by an air generator; the space velocity of the isooctyl aldehyde in the reactor is 0.1h-1The feeding molar ratio of isooctyl aldehyde to oxygen is 1:6, the number of air blowing pipes of the air generator in the oxidation reactor is 8, and the height of the air blowing pipes is60cm, with a width between the sparge tubes of 35cm, the selectivity of the reaction was 98.0% and the conversion was 100%.
Example 8
The isooctene aldehyde enters a microbubble reactor, and under the pressure of 1MPa and the temperature of 130 ℃ and the action of a platinum nanoparticle hydrogenation catalyst, the isooctene aldehyde and hydrogen undergo a selective hydrogenation reaction to produce isooctene aldehyde, the selectivity of the reaction is 97.5 percent, and the conversion rate is 99 percent. Wherein the space velocity of the raw material isooctenal in the reactor is 0.1h-1The feeding molar ratio of raw materials of isooctene aldehyde and hydrogen is 1:6, the molar ratio of the consumption of a platinum nanoparticle hydrogenation catalyst to the feeding amount of isooctene aldehyde per hour is 0.001:1, a microbubble reactor is an annular space flow fixed bed reactor, the width of an annular space channel is 3mm, the pore space of a ceramic membrane is 10nm, and the length of the ceramic membrane is 25 cm;
the obtained isooctyl aldehyde enters an oxidation reactor, and is oxidized into isooctyl acid by oxygen in micro-bubbles at the temperature of 70 ℃ through micro-bubbles blown by an air generator; the space velocity of the isooctyl aldehyde in the reactor is 0.1h-1The feeding molar ratio of isooctylaldehyde to oxygen is 1:6, the number of air blowing pipes of an air generator in the oxidation reactor is 8, the height of the air blowing pipes is 60cm, the width between the air blowing pipes is 35cm, the selectivity of the reaction is 98.0%, and the conversion rate is 100%.
Example 9
The isooctene aldehyde enters a microbubble reactor, and under the pressure of 1MPa and the temperature of 130 ℃ and the action of a vanadium nanoparticle hydrogenation catalyst, the isooctene aldehyde and hydrogen undergo a selective hydrogenation reaction to produce isooctene aldehyde, the selectivity of the reaction is 97.9 percent, and the conversion rate is 98 percent. Wherein the space velocity of the raw material isooctenal in the reactor is 0.1h-1The feeding molar ratio of raw materials of isooctene aldehyde and hydrogen is 1:6, the molar ratio of the dosage of a vanadium nanoparticle hydrogenation catalyst to the feeding amount of isooctene aldehyde per hour is 0.001:1, a microbubble reactor is an annular space flow fixed bed reactor, the width of an annular space channel is 3mm, the pore space of a ceramic membrane is 10nm, and the length of the ceramic membrane is 25 cm;
the obtained isooctyl aldehyde enters an oxidation reactor,the isooctyl aldehyde is oxidized into isooctyl acid by oxygen in the micro-bubbles at the temperature of 70 ℃ through the micro-bubbles blown by the air generator; the space velocity of the isooctyl aldehyde in the reactor is 0.1h-1The feeding molar ratio of isooctylaldehyde to oxygen is 1:6, the number of air blowing pipes of an air generator in the oxidation reactor is 8, the height of the air blowing pipes is 60cm, the width between the air blowing pipes is 35cm, the selectivity of the reaction is 98.0%, and the conversion rate is 100%.
Example 10
The isooctenal enters a microbubble reactor, and is subjected to selective hydrogenation reaction with hydrogen under the pressure of 1MPa and the temperature of 130 ℃ and under the action of a palladium oxide nanoparticle hydrogenation catalyst to produce the isooctenal, the selectivity of the reaction is 96.6 percent, and the conversion rate is 98 percent. Wherein the space velocity of the raw material isooctenal in the reactor is 0.1h-1The feeding molar ratio of raw materials of isooctene aldehyde and hydrogen is 1:6, the molar ratio of the consumption of a palladium oxide nano particle hydrogenation catalyst to the feeding amount of isooctene aldehyde per hour is 0.001:1, a microbubble reactor is an annular space flow fixed bed reactor, the width of an annular space channel is 3mm, the pore space of a ceramic membrane is 10nm, and the length of the ceramic membrane is 25 cm;
the obtained isooctyl aldehyde enters an oxidation reactor, and is oxidized into isooctyl acid by oxygen in micro-bubbles at the temperature of 70 ℃ through micro-bubbles blown by an air generator; the space velocity of the isooctyl aldehyde in the reactor is 0.1h-1The feeding molar ratio of isooctylaldehyde to oxygen is 1:6, the number of air blowing pipes of an air generator in the oxidation reactor is 8, the height of the air blowing pipes is 60cm, the width between the air blowing pipes is 35cm, the selectivity of the reaction is 98.0%, and the conversion rate is 100%.
Example 11
The isooctenal enters a microbubble reactor, and is subjected to selective hydrogenation reaction with hydrogen under the pressure of 1MPa and the temperature of 130 ℃ and under the action of a nickel oxide nano particle hydrogenation catalyst to produce the isooctenal, the selectivity of the reaction is 98.5 percent, and the conversion rate is 99 percent. Wherein the space velocity of the raw material isooctenal in the reactor is 0.1h-1The feeding molar ratio of raw material isooctenal and hydrogen is 1:6, nickel oxideThe molar ratio of the dosage of the nano particle hydrogenation catalyst to the feeding amount of the isooctene aldehyde per hour is 0.001:1, the microbubble reactor is an annular flow fixed bed reactor, the width of an annular channel of the microbubble reactor is 3mm, the pore of a ceramic membrane is 10nm, and the length of the ceramic membrane is 25 cm;
the obtained isooctyl aldehyde enters an oxidation reactor, and is oxidized into isooctyl acid by oxygen in micro-bubbles at the temperature of 70 ℃ through micro-bubbles blown by an air generator; the space velocity of the isooctyl aldehyde in the reactor is 0.1h-1The feeding molar ratio of isooctylaldehyde to oxygen is 1:6, the number of air blowing pipes of an air generator in the oxidation reactor is 8, the height of the air blowing pipes is 60cm, the width between the air blowing pipes is 35cm, the selectivity of the reaction is 98.0%, and the conversion rate is 100%.
Example 12
The isooctene aldehyde enters a microbubble reactor, and under the pressure of 1MPa and the temperature of 130 ℃ and the action of a molybdenum oxide nano particle hydrogenation catalyst, the isooctene aldehyde and hydrogen undergo selective hydrogenation reaction to produce the isooctene aldehyde, wherein the selectivity of the reaction is 98.8 percent, and the conversion rate is 98 percent. Wherein the space velocity of the raw material isooctenal in the reactor is 0.1h-1The feeding molar ratio of raw materials of isooctene aldehyde and hydrogen is 1:6, the molar ratio of the consumption of molybdenum oxide nano particle hydrogenation catalyst to the feeding amount of isooctene aldehyde per hour is 0.001:1, the microbubble reactor is an annular space flow fixed bed reactor, the width of an annular space channel is 3mm, the pore space of a ceramic membrane is 10nm, and the length of the ceramic membrane is 25 cm;
the obtained isooctyl aldehyde enters an oxidation reactor, and is oxidized into isooctyl acid by oxygen in micro-bubbles at the temperature of 70 ℃ through micro-bubbles blown by an air generator; the space velocity of the isooctyl aldehyde in the reactor is 0.1h-1The feeding molar ratio of isooctylaldehyde to oxygen is 1:6, the number of air blowing pipes of an air generator in the oxidation reactor is 8, the height of the air blowing pipes is 60cm, the width between the air blowing pipes is 35cm, the selectivity of the reaction is 98.0%, and the conversion rate is 100%.
Example 13
The isooctenal enters a microbubble reactor under the pressure of 1MPaUnder the action of a palladium nanoparticle hydrogenation catalyst at the temperature of 130 ℃, isooctenal and hydrogen are subjected to selective hydrogenation reaction to produce isooctylaldehyde, the selectivity of the reaction is 98.5%, and the conversion rate is 99%. Wherein the space velocity of the raw material isooctenal in the reactor is 0.02h-1The feeding molar ratio of raw materials of isooctene aldehyde and hydrogen is 1:6, the molar ratio of the consumption of a palladium nanoparticle hydrogenation catalyst to the feeding amount of isooctene aldehyde per hour is 0.001:1, a microbubble reactor is an annular space flow fixed bed reactor, the width of an annular space channel is 3mm, the pore space of a ceramic membrane is 10nm, and the length of the ceramic membrane is 25 cm;
the obtained isooctyl aldehyde enters an oxidation reactor, and is oxidized into isooctyl acid by oxygen in micro-bubbles at the temperature of 70 ℃ through micro-bubbles blown by an air generator; the space velocity of the isooctyl aldehyde in the reactor is 0.1h-1The feeding molar ratio of isooctylaldehyde to oxygen is 1:6, the number of air blowing pipes of an air generator in the oxidation reactor is 8, the height of the air blowing pipes is 60cm, the width between the air blowing pipes is 35cm, the selectivity of the reaction is 98.0%, and the conversion rate is 100%.
Example 14
The isooctene aldehyde enters a microbubble reactor, and under the pressure of 1MPa and the temperature of 130 ℃ and the action of a palladium nanoparticle hydrogenation catalyst, the isooctene aldehyde and hydrogen undergo a selective hydrogenation reaction to produce isooctene aldehyde, the selectivity of the reaction is 97.9 percent, and the conversion rate is 97 percent. Wherein the space velocity of the raw material isooctenal in the reactor is 0.9h-1The feeding molar ratio of raw materials of isooctene aldehyde and hydrogen is 1:6, the molar ratio of the consumption of a palladium nanoparticle hydrogenation catalyst to the feeding amount of isooctene aldehyde per hour is 0.001:1, a microbubble reactor is an annular space flow fixed bed reactor, the width of an annular space channel is 3mm, the pore space of a ceramic membrane is 10nm, and the length of the ceramic membrane is 25 cm;
the obtained isooctyl aldehyde enters an oxidation reactor, and is oxidized into isooctyl acid by oxygen in micro-bubbles at the temperature of 70 ℃ through micro-bubbles blown by an air generator; the space velocity of the isooctyl aldehyde in the reactor is 0.1h-1The feeding molar ratio of isooctylaldehyde to oxygen is 1:6, and the oxidation reactorThe number of the air blowing pipes of the hollow gas generator was 8, the height of the air blowing pipes was 60cm, the width between the air blowing pipes was 35cm, the selectivity of the reaction was 98.0%, and the conversion was 100%.
Example 15
The isooctene aldehyde enters a microbubble reactor, and under the pressure of 1MPa and the temperature of 130 ℃ and the action of a palladium nanoparticle hydrogenation catalyst, the isooctene aldehyde and hydrogen undergo a selective hydrogenation reaction to produce the isooctene aldehyde, wherein the selectivity of the reaction is 96.9 percent, and the conversion rate is 98 percent. Wherein the space velocity of the raw material isooctenal in the reactor is 0.1h-1The feeding molar ratio of raw materials of isooctene aldehyde and hydrogen is 1:2, the molar ratio of the consumption of a palladium nanoparticle hydrogenation catalyst to the feeding amount of isooctene aldehyde per hour is 0.001:1, a microbubble reactor is an annular space flow fixed bed reactor, the width of an annular space channel is 3mm, the pore space of a ceramic membrane is 10nm, and the length of the ceramic membrane is 25 cm;
the obtained isooctyl aldehyde enters an oxidation reactor, and is oxidized into isooctyl acid by oxygen in micro-bubbles at the temperature of 70 ℃ through micro-bubbles blown by an air generator; the space velocity of the isooctyl aldehyde in the reactor is 0.1h-1The feeding molar ratio of isooctylaldehyde to oxygen is 1:6, the number of air blowing pipes of an air generator in the oxidation reactor is 8, the height of the air blowing pipes is 60cm, the width between the air blowing pipes is 35cm, the selectivity of the reaction is 98.0%, and the conversion rate is 100%.
Example 16
The isooctene aldehyde enters a microbubble reactor, and under the pressure of 1MPa and the temperature of 130 ℃ and the action of a palladium nanoparticle hydrogenation catalyst, the isooctene aldehyde and hydrogen undergo a selective hydrogenation reaction to produce the isooctene aldehyde, wherein the selectivity of the reaction is 98.9 percent, and the conversion rate is 99 percent. Wherein the space velocity of the raw material isooctenal in the reactor is 0.1h-1The feeding molar ratio of raw materials of isooctene aldehyde and hydrogen is 1:20, the molar ratio of the consumption of a palladium nanoparticle hydrogenation catalyst to the feeding amount of isooctene aldehyde per hour is 0.001:1, a microbubble reactor is an annular space flow fixed bed reactor, the width of an annular space channel is 3mm, the pore space of a ceramic membrane is 10nm, and the length of the ceramic membrane is 25 cm;
the obtained isooctyl aldehyde enters an oxidation reactor, and is oxidized into isooctyl acid by oxygen in micro-bubbles at the temperature of 70 ℃ through micro-bubbles blown by an air generator; the space velocity of the isooctyl aldehyde in the reactor is 0.1h-1The feeding molar ratio of isooctylaldehyde to oxygen is 1:6, the number of air blowing pipes of an air generator in the oxidation reactor is 8, the height of the air blowing pipes is 60cm, the width between the air blowing pipes is 35cm, the selectivity of the reaction is 98.0%, and the conversion rate is 100%.
Example 17
The isooctene aldehyde enters a microbubble reactor, and under the pressure of 1MPa and the temperature of 130 ℃ and the action of a palladium nanoparticle hydrogenation catalyst, the isooctene aldehyde and hydrogen undergo a selective hydrogenation reaction to produce isooctene aldehyde, the selectivity of the reaction is 96.8 percent, and the conversion rate is 98 percent. Wherein the space velocity of the raw material isooctenal in the reactor is 0.1h-1The feeding molar ratio of raw materials of isooctenal and hydrogen is 1:6, the molar ratio of the consumption of a palladium nanoparticle hydrogenation catalyst to the feeding amount of isooctenal per hour is 0.0005:1, a microbubble reactor is an annular flow fixed bed reactor, the width of an annular channel is 3mm, the pore of a ceramic membrane is 10nm, and the length of the ceramic membrane is 25 cm;
the obtained isooctyl aldehyde enters an oxidation reactor, and is oxidized into isooctyl acid by oxygen in micro-bubbles at the temperature of 70 ℃ through micro-bubbles blown by an air generator; the space velocity of the isooctyl aldehyde in the reactor is 0.1h-1The feeding molar ratio of isooctylaldehyde to oxygen is 1:6, the number of air blowing pipes of an air generator in the oxidation reactor is 8, the height of the air blowing pipes is 60cm, the width between the air blowing pipes is 35cm, the selectivity of the reaction is 98.0%, and the conversion rate is 100%.
Example 18
The isooctene aldehyde enters a microbubble reactor, and under the pressure of 1MPa and the temperature of 130 ℃ and the action of a palladium nanoparticle hydrogenation catalyst, the isooctene aldehyde and hydrogen undergo a selective hydrogenation reaction to produce the isooctene aldehyde, wherein the selectivity of the reaction is 98.8 percent, and the conversion rate is 99 percent. Wherein the space velocity of the raw material isooctenal in the reactor is 0.1h-1Isooctene as raw materialThe feeding molar ratio of aldehyde to hydrogen is 1:6, the molar ratio of the consumption of the palladium nanoparticle hydrogenation catalyst to the feeding amount of isooctene aldehyde per hour is 0.008:1, the microbubble reactor is an annular space flow fixed bed reactor, the width of an annular space channel is 3mm, the pore of a ceramic membrane is 10nm, and the length of the ceramic membrane is 25 cm;
the obtained isooctyl aldehyde enters an oxidation reactor, and is oxidized into isooctyl acid by oxygen in micro-bubbles at the temperature of 70 ℃ through micro-bubbles blown by an air generator; the space velocity of the isooctyl aldehyde in the reactor is 0.1h-1The feeding molar ratio of isooctylaldehyde to oxygen is 1:6, the number of air blowing pipes of an air generator in the oxidation reactor is 8, the height of the air blowing pipes is 60cm, the width between the air blowing pipes is 35cm, the selectivity of the reaction is 98.0%, and the conversion rate is 100%.
Example 19
The isooctene aldehyde enters a microbubble reactor, and under the pressure of 1MPa and the temperature of 130 ℃ and the action of a palladium nanoparticle hydrogenation catalyst, the isooctene aldehyde and hydrogen undergo a selective hydrogenation reaction to produce the isooctene aldehyde, wherein the selectivity of the reaction is 99.5 percent, and the conversion rate is 100 percent. Wherein the space velocity of the raw material isooctenal in the reactor is 0.1h-1The feeding molar ratio of raw materials of isooctene aldehyde and hydrogen is 1:6, the molar ratio of the consumption of a palladium nanoparticle hydrogenation catalyst to the feeding amount of isooctene aldehyde per hour is 0.001:1, a microbubble reactor is an annular space flow fixed bed reactor, the width of an annular space channel is 3mm, the pore space of a ceramic membrane is 10nm, and the length of the ceramic membrane is 25 cm;
the obtained isooctyl aldehyde enters an oxidation reactor, and is oxidized into isooctyl acid by oxygen in micro-bubbles at the temperature of 50 ℃ through the micro-bubbles blown by an air generator; the space velocity of the isooctyl aldehyde in the reactor is 0.1h-1The feeding molar ratio of isooctylaldehyde to oxygen is 1:6, the number of air blowing pipes of the air generator in the oxidation reactor is 8, the height of the air blowing pipes is 60cm, the width between the air blowing pipes is 35cm, the selectivity of the reaction is 96.5%, and the conversion rate is 98%.
Example 20
Entry of isooctenal into microbubble reverse reactionIn a reactor, under the pressure of 1MPa and the temperature of 130 ℃ and the action of a palladium nanoparticle hydrogenation catalyst, isooctylaldehyde and hydrogen are subjected to selective hydrogenation reaction to produce isooctylaldehyde, wherein the selectivity of the reaction is 99.5%, and the conversion rate is 100%. Wherein the space velocity of the raw material isooctenal in the reactor is 0.1h-1The feeding molar ratio of raw materials of isooctene aldehyde and hydrogen is 1:6, the molar ratio of the consumption of a palladium nanoparticle hydrogenation catalyst to the feeding amount of isooctene aldehyde per hour is 0.001:1, a microbubble reactor is an annular space flow fixed bed reactor, the width of an annular space channel is 3mm, the pore space of a ceramic membrane is 10nm, and the length of the ceramic membrane is 25 cm;
the obtained isooctyl aldehyde enters an oxidation reactor, and is oxidized into isooctyl acid by oxygen in micro-bubbles at the temperature of 120 ℃ through micro-bubbles blown by an air generator; the space velocity of the isooctyl aldehyde in the reactor is 0.1h-1The feeding molar ratio of isooctylaldehyde to oxygen was 1:6, 8 sets of air-blowing tubes of the air generator in the oxidation reactor, the height of the air-blowing tubes was 60cm, the width between the air-blowing tubes was 35cm, the selectivity of the reaction was 95.9%, and the conversion was 98%.
Example 21
The isooctene aldehyde enters a microbubble reactor, and under the pressure of 1MPa and the temperature of 130 ℃ and the action of a palladium nanoparticle hydrogenation catalyst, the isooctene aldehyde and hydrogen undergo a selective hydrogenation reaction to produce the isooctene aldehyde, wherein the selectivity of the reaction is 99.5 percent, and the conversion rate is 100 percent. Wherein the space velocity of the raw material isooctenal in the reactor is 0.1h-1The feeding molar ratio of raw materials of isooctene aldehyde and hydrogen is 1:6, the molar ratio of the consumption of a palladium nanoparticle hydrogenation catalyst to the feeding amount of isooctene aldehyde per hour is 0.001:1, a microbubble reactor is an annular space flow fixed bed reactor, the width of an annular space channel is 3mm, the pore space of a ceramic membrane is 10nm, and the length of the ceramic membrane is 25 cm;
the obtained isooctyl aldehyde enters an oxidation reactor, and is oxidized into isooctyl acid by oxygen in micro-bubbles at the temperature of 70 ℃ through micro-bubbles blown by an air generator; the space velocity of the isooctyl aldehyde in the reactor is 0.02h-1Feeding of isooctanal and oxygenThe molar ratio was 1:6, 8 sets of gas tubes in the air generator of the oxidation reactor, the height of the gas tubes was 60cm, the width between the gas tubes was 35cm, the selectivity of the reaction was 97.6%, and the conversion was 98%.
Example 22
The isooctene aldehyde enters a microbubble reactor, and under the pressure of 1MPa and the temperature of 130 ℃ and the action of a palladium nanoparticle hydrogenation catalyst, the isooctene aldehyde and hydrogen undergo a selective hydrogenation reaction to produce the isooctene aldehyde, wherein the selectivity of the reaction is 99.5 percent, and the conversion rate is 100 percent. Wherein the space velocity of the raw material isooctenal in the reactor is 0.1h-1The feeding molar ratio of raw materials of isooctene aldehyde and hydrogen is 1:6, the molar ratio of the consumption of a palladium nanoparticle hydrogenation catalyst to the feeding amount of isooctene aldehyde per hour is 0.001:1, a microbubble reactor is an annular space flow fixed bed reactor, the width of an annular space channel is 3mm, the pore space of a ceramic membrane is 10nm, and the length of the ceramic membrane is 25 cm;
the obtained isooctyl aldehyde enters an oxidation reactor, and is oxidized into isooctyl acid by oxygen in micro-bubbles at the temperature of 70 ℃ through micro-bubbles blown by an air generator; the space velocity of the isooctyl aldehyde in the reactor is 0.8h-1The feeding molar ratio of isooctylaldehyde to oxygen was 1:6, 8 sets of air-blowing tubes of the air generator in the oxidation reactor, the height of the air-blowing tubes was 60cm, the width between the air-blowing tubes was 35cm, the selectivity of the reaction was 96.6%, and the conversion was 98%.
Example 23
The isooctene aldehyde enters a microbubble reactor, and under the pressure of 1MPa and the temperature of 130 ℃ and the action of a palladium nanoparticle hydrogenation catalyst, the isooctene aldehyde and hydrogen undergo a selective hydrogenation reaction to produce the isooctene aldehyde, wherein the selectivity of the reaction is 99.5 percent, and the conversion rate is 100 percent. Wherein the space velocity of the raw material isooctenal in the reactor is 0.1h-1The feeding molar ratio of raw materials of isooctenal and hydrogen is 1:6, the molar ratio of the dosage of the palladium nano particle hydrogenation catalyst to the feeding amount of isooctenal per hour is 0.001:1, the microbubble reactor is an annular space flow fixed bed reactor, the width of an annular space channel is 3mm, the pore space of a ceramic membrane is 10nm, and the length of the ceramic membrane is 25cm；
The obtained isooctyl aldehyde enters an oxidation reactor, and is oxidized into isooctyl acid by oxygen in micro-bubbles at the temperature of 70 ℃ through micro-bubbles blown by an air generator; the space velocity of the isooctyl aldehyde in the reactor is 0.1h-1The feeding molar ratio of isooctylaldehyde to oxygen was 1:2, 8 sets of air-blowing tubes of the air generator in the oxidation reactor, the height of the air-blowing tubes was 60cm, the width between the air-blowing tubes was 35cm, the selectivity of the reaction was 96.1%, and the conversion was 97%.
Example 24
The isooctene aldehyde enters a microbubble reactor, and under the pressure of 1MPa and the temperature of 130 ℃ and the action of a palladium nanoparticle hydrogenation catalyst, the isooctene aldehyde and hydrogen undergo a selective hydrogenation reaction to produce the isooctene aldehyde, wherein the selectivity of the reaction is 99.5 percent, and the conversion rate is 100 percent. Wherein the space velocity of the raw material isooctenal in the reactor is 0.1h-1The feeding molar ratio of raw materials of isooctene aldehyde and hydrogen is 1:6, the molar ratio of the consumption of a palladium nanoparticle hydrogenation catalyst to the feeding amount of isooctene aldehyde per hour is 0.001:1, a microbubble reactor is an annular space flow fixed bed reactor, the width of an annular space channel is 3mm, the pore space of a ceramic membrane is 10nm, and the length of the ceramic membrane is 25 cm;
the obtained isooctyl aldehyde enters an oxidation reactor, and is oxidized into isooctyl acid by oxygen in micro-bubbles at the temperature of 70 ℃ through micro-bubbles blown by an air generator; the space velocity of the isooctyl aldehyde in the reactor is 0.1h-1The feeding molar ratio of isooctylaldehyde to oxygen was 1:20, 8 sets of air-blowing tubes of the air generator in the oxidation reactor, the height of the air-blowing tubes was 60cm, the width between the air-blowing tubes was 35cm, the selectivity of the reaction was 96.3%, and the conversion was 98%.
Example 25
The isooctene aldehyde enters a microbubble reactor, and under the pressure of 1MPa and the temperature of 130 ℃ and the action of a palladium nanoparticle hydrogenation catalyst, the isooctene aldehyde and hydrogen undergo a selective hydrogenation reaction to produce the isooctene aldehyde, wherein the selectivity of the reaction is 99.5 percent, and the conversion rate is 100 percent. Wherein the space velocity of the raw material isooctenal in the reactor is 0.1h-1The feeding molar ratio of raw materials of isooctene aldehyde and hydrogen is 1:6, the molar ratio of the consumption of a palladium nanoparticle hydrogenation catalyst to the feeding amount of isooctene aldehyde per hour is 0.001:1, a microbubble reactor is an annular space flow fixed bed reactor, the width of an annular space channel is 3mm, the pore space of a ceramic membrane is 10nm, and the length of the ceramic membrane is 25 cm;
uniformly mixing the obtained isooctyl aldehyde and a manganese acetate oxidation catalyst, then feeding the mixture into an oxidation reactor, and oxidizing the isooctyl aldehyde into isooctanoic acid by oxygen in microbubbles at the temperature of 70 ℃ through microbubbles blown by an air generator; the space velocity of the isooctyl aldehyde in the reactor is 0.1h-1The feeding molar ratio of isooctanal to oxygen is 1:6, the molar ratio of the amount of manganese acetate oxidation catalyst to the hourly feeding amount of isooctanal is 0.05:1, 8 sets of air blowing pipes of the air generator in the oxidation reactor are provided, the height of the air blowing pipes is 60cm, the width between the air blowing pipes is 35cm, the selectivity of the reaction is 95.6%, and the conversion rate is 99%.
Example 26
The isooctene aldehyde enters a microbubble reactor, and under the pressure of 1MPa and the temperature of 130 ℃ and the action of a palladium nanoparticle hydrogenation catalyst, the isooctene aldehyde and hydrogen undergo a selective hydrogenation reaction to produce the isooctene aldehyde, wherein the selectivity of the reaction is 99.5 percent, and the conversion rate is 100 percent. Wherein the space velocity of the raw material isooctenal in the reactor is 0.1h-1The feeding molar ratio of raw materials of isooctene aldehyde and hydrogen is 1:6, the molar ratio of the consumption of a palladium nanoparticle hydrogenation catalyst to the feeding amount of isooctene aldehyde per hour is 0.001:1, a microbubble reactor is an annular space flow fixed bed reactor, the width of an annular space channel is 3mm, the pore space of a ceramic membrane is 10nm, and the length of the ceramic membrane is 25 cm;
uniformly mixing the obtained isooctyl aldehyde and a manganese acetate oxidation catalyst, then feeding the mixture into an oxidation reactor, and oxidizing the isooctyl aldehyde into isooctanoic acid by oxygen in microbubbles at the temperature of 70 ℃ through microbubbles blown by an air generator; the space velocity of the isooctyl aldehyde in the reactor is 0.1h-1The molar ratio of the feed of isooctanal to oxygen was 1:6, the molar ratio of the amount of manganese acetate oxidation catalyst to the feed of isooctanal per hour was 0.005:1, and oxygen was addedThe number of the gas blowing tubes of the gas generator in the chemical reactor was 8, the height of the gas blowing tubes was 60cm, the width between the gas blowing tubes was 35cm, the selectivity of the reaction was 94.9%, and the conversion was 98%.
Example 27
The isooctene aldehyde enters a microbubble reactor, and under the pressure of 1MPa and the temperature of 130 ℃ and the action of a palladium nanoparticle hydrogenation catalyst, the isooctene aldehyde and hydrogen undergo a selective hydrogenation reaction to produce the isooctene aldehyde, wherein the selectivity of the reaction is 99.5 percent, and the conversion rate is 100 percent. Wherein the space velocity of the raw material isooctenal in the reactor is 0.1h-1The feeding molar ratio of raw materials of isooctene aldehyde and hydrogen is 1:6, the molar ratio of the consumption of a palladium nanoparticle hydrogenation catalyst to the feeding amount of isooctene aldehyde per hour is 0.001:1, a microbubble reactor is an annular space flow fixed bed reactor, the width of an annular space channel is 3mm, the pore space of a ceramic membrane is 10nm, and the length of the ceramic membrane is 25 cm;
uniformly mixing the obtained isooctyl aldehyde and a cobalt acetate oxidation catalyst, then feeding the mixture into an oxidation reactor, and oxidizing the isooctyl aldehyde into isooctanoic acid by oxygen in microbubbles at the temperature of 70 ℃ through microbubbles blown by an air generator; the space velocity of the isooctyl aldehyde in the reactor is 0.1h-1The feeding molar ratio of isooctylaldehyde to oxygen is 1:6, the molar ratio of the dosage of the cobalt acetate oxidation catalyst to the hourly feeding amount of isooctylaldehyde is 0.08:1, 8 groups of air blowing pipes of the air generator in the oxidation reactor are provided, the height of the air blowing pipes is 60cm, the width between the air blowing pipes is 35cm, the selectivity of the reaction is 96.5%, and the conversion rate is 98%.
Example 28
The isooctene aldehyde enters a microbubble reactor, and under the pressure of 1MPa and the temperature of 130 ℃ and the action of a palladium nanoparticle hydrogenation catalyst, the isooctene aldehyde and hydrogen undergo a selective hydrogenation reaction to produce the isooctene aldehyde, wherein the selectivity of the reaction is 99.5 percent, and the conversion rate is 100 percent. Wherein the space velocity of the raw material isooctenal in the reactor is 0.1h-1The feeding molar ratio of raw materials of isooctenal and hydrogen is 1:6, the molar ratio of the dosage of the palladium nano particle hydrogenation catalyst to the feeding amount of isooctenal per hour is 0.001:1, and the microbubble reactor is an annular space flowThe width of an annular space channel of the fixed bed reactor is 3mm, the pore space of the ceramic membrane is 10nm, and the length of the ceramic membrane is 25 cm;
uniformly mixing the obtained isooctyl aldehyde and a cobalt acetate oxidation catalyst, then feeding the mixture into an oxidation reactor, and oxidizing the isooctyl aldehyde into isooctanoic acid by oxygen in microbubbles at the temperature of 70 ℃ through microbubbles blown by an air generator; the space velocity of the isooctyl aldehyde in the reactor is 0.1h-1The feeding molar ratio of isooctanal to oxygen was 1:6, the molar ratio of the amount of cobalt acetate oxidation catalyst to the amount of isooctanal fed per hour was 0.009:1, 8 sets of air-blowing tubes of the air generator in the oxidation reactor, the height of the air-blowing tubes was 60cm, the width between the air-blowing tubes was 35cm, the selectivity of the reaction was 96.1%, and the conversion was 98%.
Example 29
The isooctene aldehyde enters a microbubble reactor, and under the pressure of 1MPa and the temperature of 130 ℃ and the action of a palladium nanoparticle hydrogenation catalyst, the isooctene aldehyde and hydrogen undergo a selective hydrogenation reaction to produce the isooctene aldehyde, wherein the selectivity of the reaction is 99.1 percent, and the conversion rate is 100 percent. Wherein the space velocity of the raw material isooctenal in the reactor is 0.1h-1The feeding molar ratio of raw materials of isooctene aldehyde and hydrogen is 1:6, the molar ratio of the consumption of a palladium nanoparticle hydrogenation catalyst to the feeding amount of isooctene aldehyde per hour is 0.001:1, a microbubble reactor is an annular space flow fixed bed reactor, the width of an annular space channel is 5mm, the pore space of a ceramic membrane is 50nm, and the length of the ceramic membrane is 25 cm;
the obtained isooctyl aldehyde enters an oxidation reactor, and is oxidized into isooctyl acid by oxygen in micro-bubbles at the temperature of 70 ℃ through micro-bubbles blown by an air generator; the space velocity of the isooctyl aldehyde in the reactor is 0.1h-1The feeding molar ratio of isooctylaldehyde to oxygen is 1:6, the number of blowing tubes of the air generator in the oxidation reactor is 4, the height of the blowing tubes is 30cm, the width between the blowing tubes is 55cm, the selectivity of the reaction is 98.2%, and the conversion rate is 99%.
Example 30
Introducing isooctenal into a microbubble reactor at a pressure of 1MPa and a temperature of 130 deg.CUnder the action of the palladium nanoparticle hydrogenation catalyst at the temperature, the isooctenal and hydrogen are subjected to selective hydrogenation reaction to produce the isooctylaldehyde, the selectivity of the reaction is 99.3%, and the conversion rate is 100%. Wherein the space velocity of the raw material isooctenal in the reactor is 0.1h-1The feeding molar ratio of raw materials of isooctene aldehyde and hydrogen is 1:6, the molar ratio of the consumption of a palladium nanoparticle hydrogenation catalyst to the feeding amount of isooctene aldehyde per hour is 0.001:1, a microbubble reactor is an annular space flow fixed bed reactor, the width of an annular space channel is 2mm, the pore space of a ceramic membrane is 80nm, and the length of the ceramic membrane is 85 cm;
the obtained isooctyl aldehyde enters an oxidation reactor, and is oxidized into isooctyl acid by oxygen in micro-bubbles at the temperature of 70 ℃ through micro-bubbles blown by an air generator; the space velocity of the isooctyl aldehyde in the reactor is 0.1h-1The feeding molar ratio of isooctylaldehyde to oxygen is 1:6, 5 groups of air blowing pipes of an air generator in an oxidation reactor are provided, the height of the air blowing pipes is 80cm, the width between the air blowing pipes is 85cm, the selectivity of the reaction is 98.9 percent, and the conversion rate is 99 percent.

Claims (10)

1. A production process for preparing isooctanoic acid by using isooctenal as a raw material is characterized by comprising the following steps:
(1) in a micro-bubble reactor, carrying out selective hydrogenation reaction by taking isooctenal as a raw material under the action of a nano particle hydrogenation catalyst to prepare isooctanal;
(2) and (2) feeding the isooctaldehyde obtained in the step (1) into an oxidation reactor, blowing micro bubbles through an air generator, and reacting the isooctaldehyde with oxygen in the micro bubbles to obtain the isooctanoic acid.
2. The production process for preparing isooctanoic acid from isooctenal as claimed in claim 1, characterized in that: in the step (1), the nanoparticle hydrogenation catalyst is nanoparticles of gold, palladium, platinum, nickel, vanadium, molybdenum, manganese or oxides thereof; the molar ratio of the nanoparticle hydrogenation catalyst to the isooctenal feed per hour is 0.00008-0.01: 1.
3. The production process for preparing isooctanoic acid from isooctenal as claimed in claim 1, characterized in that: in the step (1), the temperature of the selective hydrogenation reaction is 30-170 ℃, and the pressure is 0.1-10 MPa.
4. The production process for preparing isooctanoic acid from isooctenal as claimed in claim 1, characterized in that: in the step (1), the space velocity of the isooctene aldehyde in the selective hydrogenation reaction process is 0.005-1h-1The feeding molar ratio of the isooctenal to the hydrogen is 1: 1-40.
5. The production process for preparing isooctanoic acid from isooctenal as claimed in claim 1, characterized in that: in the step (2), the isooctyl aldehyde enters an oxidation reactor for reaction, and the space velocity of the isooctyl aldehyde is 0.005-1h-1The feeding molar ratio of the isooctyl aldehyde to the oxygen is 1: 1-40; the reaction temperature of the isooctyl aldehyde in the oxidation reactor is 20-150 ℃.
6. The process for preparing isooctanoic acid from isooctenal according to any one of claims 1 to 5, wherein: the method comprises the following steps:
(1) in a micro-bubble reactor, carrying out selective hydrogenation reaction by taking isooctenal as a raw material under the action of a nano particle hydrogenation catalyst to prepare isooctanal;
(2) mixing the isooctaldehyde obtained in the step (1) with an oxidation catalyst, then feeding the mixture into an oxidation reactor, blowing micro bubbles through an air generator, and reacting the isooctaldehyde with oxygen in the micro bubbles to obtain the isooctanoic acid.
7. The production process for preparing isooctanoic acid from isooctenal as claimed in claim 6, wherein: in the step (2), the oxidation catalyst is cobalt acetate, molybdenum acetate, silver acetate, manganese isooctanoate, cobalt isooctanoate, molybdenum isooctanoate, silver isooctanoate, manganese dioxide, silver oxide, vanadium acetylacetonate, molybdenum trioxide, vanadium pentoxide, aluminum oxide, ferric chloride or palladium oxide; the molar ratio of the oxidation catalyst to the amount of isooctylaldehyde fed per hour is 0-0.1: 1.
8. The production process for preparing isooctanoic acid from isooctenal as claimed in claim 6, wherein: the method comprises the following steps:
(1) the microbubble reactor comprises a gas phase inlet (1), a liquid phase inlet (2), a microbubble tube (3) and a reaction zone (6), the microbubble tube (3), the gas phase inlet (1) and the liquid phase inlet (2) are positioned at the upper part of the reaction zone (6), an annular space channel is formed between the microbubble tube (3) and the tube wall of the microbubble reactor, the liquid phase inlet (2) is connected with the annular space channel, and the gas phase inlet (1) is connected with the microbubble tube (3); a nano particle hydrogenation catalyst (4) is arranged in the reaction zone (6), and a heating medium channel (5) is arranged outside the reaction zone (6);
hydrogen enters a micro bubble tube (3) from a gas phase inlet (1), isooctene aldehyde enters an annular space channel formed between the micro bubble tube (3) and the tube wall of the micro bubble reactor from a liquid phase inlet (2), the hydrogen and the isooctene aldehyde undergo selective hydrogenation reaction under the action of a nano particle hydrogenation catalyst (4) in a reaction zone (6) through the micro bubble tube (3) to prepare isooctene aldehyde, and the isooctene aldehyde flows out from the bottom of the micro bubble reactor;
(2) an air generator (9) is arranged at the bottom of the oxidation reactor, an air outlet (7) is arranged at the top of the oxidation reactor, an isooctyl aldehyde inlet (8) is arranged on one side surface of the oxidation reactor, an isooctanoic acid outlet (11) is arranged on the other side surface of the oxidation reactor, the isooctanoic acid outlet (11) is higher than the isooctyl aldehyde inlet (8), and a filter (12) is arranged at the isooctanoic acid outlet (11); an insulating layer (10) is also arranged around the oxidation reactor;
and (2) enabling the isooctaldehyde obtained in the step (1) to enter an oxidation reactor from an isooctaldehyde inlet (8), blowing micro-bubbles through an air generator (9), enabling the isooctaldehyde to react with oxygen in the micro-bubbles to prepare isooctanoic acid, and enabling the isooctanoic acid to flow out of the oxidation reactor from an isooctanoic acid outlet (11).
9. The production process for preparing isooctanoic acid from isooctenal as claimed in claim 8, wherein: in the step (1), the microbubble reactor is an annular space flow fixed bed reactor; the width of the annular gap channel is 1-5 mm; the micro bubble tube (3) is made of a ceramic membrane, the pore size of the ceramic membrane is 5-100nm, and the length of the ceramic membrane is 5-100 cm.
10. The production process for preparing isooctanoic acid from isooctenal as claimed in claim 8, wherein: in the step (2), the air blowing pipes of the air generator are 1-10 groups, the height of the air blowing pipes is 5-100cm, and the width between the air blowing pipes is 5-100 cm.
CN202010622761.6A 2020-07-01 2020-07-01 Production process for preparing isooctanoic acid by using isooctene aldehyde as raw material Active CN111620772B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202010622761.6A CN111620772B (en) 2020-07-01 2020-07-01 Production process for preparing isooctanoic acid by using isooctene aldehyde as raw material

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202010622761.6A CN111620772B (en) 2020-07-01 2020-07-01 Production process for preparing isooctanoic acid by using isooctene aldehyde as raw material

Publications (2)

Publication Number Publication Date
CN111620772A true CN111620772A (en) 2020-09-04
CN111620772B CN111620772B (en) 2023-04-18

Family

ID=72269520

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202010622761.6A Active CN111620772B (en) 2020-07-01 2020-07-01 Production process for preparing isooctanoic acid by using isooctene aldehyde as raw material

Country Status (1)

Country Link
CN (1) CN111620772B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116212962A (en) * 2023-02-24 2023-06-06 润和科华催化剂(上海)有限公司 Oil-soluble molybdenum isooctanoate catalyst and preparation method thereof

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU1697381A1 (en) * 1990-04-28 1997-02-27 Ленинградское научно-производственное объединение по разработке и внедрению нефтехимических процессов "Леннефтехим" Method for production of 2-ethylhexylic acid
CN106237966A (en) * 2016-08-23 2016-12-21 南京大学 The reactor of aromatic aldehyde is produced for the oxidation of toluene class material
CN108250069A (en) * 2018-01-22 2018-07-06 万华化学集团股份有限公司 A kind of preparation method of isooctyl acid
CN109225073A (en) * 2018-09-17 2019-01-18 清华大学 Hydrogenation reaction device and its method for carrying out hydrogenation reaction in a kind of micro- packed bed
CN109679690A (en) * 2017-10-19 2019-04-26 中国石油化工股份有限公司 A kind of liquid-phase hydrogenatin system and liquid phase hydrogenating method
CN111054437A (en) * 2018-10-17 2020-04-24 中国石油化工股份有限公司 Catalyst for preparing isooctylaldehyde through selective hydrogenation of isooctenal, preparation method and application

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU1697381A1 (en) * 1990-04-28 1997-02-27 Ленинградское научно-производственное объединение по разработке и внедрению нефтехимических процессов "Леннефтехим" Method for production of 2-ethylhexylic acid
CN106237966A (en) * 2016-08-23 2016-12-21 南京大学 The reactor of aromatic aldehyde is produced for the oxidation of toluene class material
CN109679690A (en) * 2017-10-19 2019-04-26 中国石油化工股份有限公司 A kind of liquid-phase hydrogenatin system and liquid phase hydrogenating method
CN108250069A (en) * 2018-01-22 2018-07-06 万华化学集团股份有限公司 A kind of preparation method of isooctyl acid
CN109225073A (en) * 2018-09-17 2019-01-18 清华大学 Hydrogenation reaction device and its method for carrying out hydrogenation reaction in a kind of micro- packed bed
CN111054437A (en) * 2018-10-17 2020-04-24 中国石油化工股份有限公司 Catalyst for preparing isooctylaldehyde through selective hydrogenation of isooctenal, preparation method and application

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116212962A (en) * 2023-02-24 2023-06-06 润和科华催化剂(上海)有限公司 Oil-soluble molybdenum isooctanoate catalyst and preparation method thereof

Also Published As

Publication number Publication date
CN111620772B (en) 2023-04-18

Similar Documents

Publication Publication Date Title
CN106430108B (en) System and method for preparing hydrogen peroxide by anthraquinone method under supergravity condition
CN103936559A (en) Method for continuously producing resorcin
CN111620772B (en) Production process for preparing isooctanoic acid by using isooctene aldehyde as raw material
CN103755521A (en) Method for producing KA oil through oxidizing cyclohexane by using air on basis of gas-liquid-solid heterogeneous reaction separation synchronization reactor
CN115716918A (en) Method for preparing metal-organic framework material by ball milling-solution blending
CN110026145A (en) A kind of hypergravity reaction unit and its application
CN100372827C (en) Production of isooctaacid by composite catalytic method
CN104844436B (en) A kind of clean preparation method of vanillic aldehyde
CN107778175A (en) The synthesis technique of the tricaprylate of Isosorbide-5-Nitrae cyclohexanedimethanol two
CN103626681A (en) Method for preparing 4,4'-dinitrostilbene-2,2'-disulfonic acid
CN1312103C (en) Oxosynthesis of azelaic acid and nonoic acid with mixed ozone solvent
CN110240197B (en) Ultrathin nanosheet self-assembled multilayer BiOCl microsphere and application thereof in photocatalytic coupling of benzylamine to imine
CN111151201A (en) Reaction device and system and method for synthesizing acetic acid by methanol carbonylation
CN101830820B (en) Method for preparing 2,5-diparamethylaniline terephthalic acid (DTTA)
CN110016001A (en) A kind of continuous synthetic method of benzotriazole
CN212595615U (en) Reaction unit and system for synthesizing acetic acid by methanol carbonyl
CN106220513B (en) A method of preparing nonamethylene diamine
CN212142628U (en) Production equipment for continuously carbonizing synthetic calcium carbonate
CN116178130A (en) Green synthesis method of 2-ethylhexanoic acid
CN109320397A (en) A kind of preparation method of neopentyl glycol
CN215828659U (en) Device for continuously hydrolyzing ethylene carbonate
CN1079388C (en) Method for preparing cyclohexanol and cyclohexanone
CN102001938A (en) Process and production system for synthesizing dimethyl oxalate or diethyl oxalate and coproducing oxalic acid
CN111744452A (en) 2-chlorobenzoic acid continuous flow synthesis device and method for synthesizing 2-chlorobenzoic acid
CN101289379B (en) Process for preparing bromoundecanoic acid by tower type addition of undecylenic acid

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
CB02 Change of applicant information

Address after: 255086 room 313, block A, Gao Chuang garden, hi tech Development Zone, Zibo, Shandong.

Applicant after: Shandong University of Technology

Applicant after: Zibo Nalcohol Chemical Co.,Ltd.

Address before: 255086 room 313, block A, Gao Chuang garden, hi tech Development Zone, Zibo, Shandong.

Applicant before: Shandong University of Technology

Applicant before: ZIBO NALCOHOL CHEMICAL CO.,LTD.

CB02 Change of applicant information
GR01 Patent grant
GR01 Patent grant