CN113620796B - Continuous preparation method and system of dibenzoylmethane - Google Patents

Continuous preparation method and system of dibenzoylmethane Download PDF

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Publication number
CN113620796B
CN113620796B CN202110707833.1A CN202110707833A CN113620796B CN 113620796 B CN113620796 B CN 113620796B CN 202110707833 A CN202110707833 A CN 202110707833A CN 113620796 B CN113620796 B CN 113620796B
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heating area
dibenzoylmethane
esterification reaction
tank
rectifying tower
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CN113620796A (en
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李兑
童庆军
李平
张国靓
王艳
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ANHUI JIAXIAN FUNCTIONAL AUXILIARY CO LTD
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ANHUI JIAXIAN FUNCTIONAL AUXILIARY CO LTD
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    • 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
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
    • B01D3/14—Fractional distillation or use of a fractionation or rectification column
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
    • B01D3/14—Fractional distillation or use of a fractionation or rectification column
    • B01D3/32—Other features of fractionating columns ; Constructional details of fractionating columns not provided for in groups B01D3/16 - B01D3/30
    • 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
    • B01J19/0006—Controlling or regulating processes
    • B01J19/0013—Controlling the temperature of the process
    • 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
    • B01J19/24—Stationary reactors without moving elements inside
    • B01J19/245—Stationary reactors without moving elements inside placed in series
    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0215—Sulfur-containing compounds
    • B01J31/0225—Sulfur-containing compounds comprising sulfonic acid groups or the corresponding salts
    • 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
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/19—Catalysts containing parts with different compositions
    • 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
    • B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • 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
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/49—Esterification or transesterification
    • 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
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/02—Sulfur, selenium or tellurium; Compounds thereof
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/584—Recycling of catalysts

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention discloses a continuous preparation method and a continuous preparation system of dibenzoylmethane, wherein the preparation method comprises the following steps: taking benzoic acid and methanol as raw materials, carrying out esterification reaction for 3-6 hours at 100-110 ℃ under the catalysis of a composite catalyst, and rectifying after the reaction is finished to obtain methyl benzoate; methyl benzoate is directly mixed with a dimethylbenzene solution containing acetophenone and sodium methoxide to carry out a claisen condensation reaction, and after the reaction is finished, dibenzoylmethane is obtained by crystallization and filtration; the invention overcomes the defects of the prior art, ensures continuous production, improves the reaction speed, shortens the reaction time and improves the yield of dibenzoylmethane.

Description

Continuous preparation method and system of dibenzoylmethane
Technical Field
The invention relates to the technical field of dibenzoylmethane production, and in particular relates to a continuous preparation method and system of dibenzoylmethane.
Background
The PVC heat stabilizer is mainly a lead salt stabilizer used in the domestic market at present, but the use of the lead salt heat stabilizer is greatly limited in the future along with the implementation of new environmental protection laws in China and the gradual enhancement of environmental protection consciousness of people along with the soundness of environmental protection laws and concerns on the quality and safety of products. Meanwhile, along with the revision of national environmental protection laws and the continuous enhancement of people on environmental protection consciousness, the leadless heat stabilizer has huge market potential. In the year 2016, 12 months, the departments of industrial and telecommunication, scientific and technical and environmental protection, etc. are going out from the national encouragement of the replacement of the catalogue 2016 edition by toxic and harmful raw materials (products), and the encouragement of the replacement of lead salt heat stabilizers by heat stabilizers such as calcium-based, calcium-zinc and the like.
The common environment-friendly leadless heat stabilizer mainly comprises calcium stearate, zinc stearate and the like. The single stearate has the problems of zinc burning, early color difference, insufficient weather resistance and the like when being singly used, and needs to be matched with heat stabilizer additives such as dibenzoylmethane and the like serving as a core material. However, in the industrial production, dibenzoylmethane has key technical problems, mainly comprising: (1) The industrial synthesis technology has low yield, high raw material consumption and high production cost; (2) a plurality of byproducts and great difficulty in subsequent treatment; (3) The industrial drying technology has low efficiency, restricts the production capacity, and cannot meet the increasing market demands; (4) The color and luster of the product are poor, the smell is large, and the color and luster and long-term stability of the PVC product are affected; (5) The three-waste treatment technology is not mature, and the normal production of products is restricted.
Disclosure of Invention
The invention aims to provide a continuous preparation method and a continuous preparation system of dibenzoylmethane, which solve the problems of low yield, high raw material consumption and high production cost of the industrial synthesis technology of dibenzoylmethane.
In order to solve the problems, the technical scheme adopted by the invention is as follows:
a continuous preparation method of dibenzoylmethane, comprising the following steps:
s1, using benzoic acid and methanol as raw materials, carrying out esterification reaction for 3-6 hours at 100-110 ℃ under the catalysis of a composite catalyst, and rectifying after the reaction is finished to obtain methyl benzoate;
s2, directly mixing methyl benzoate with a dimethylbenzene solution containing acetophenone and sodium methoxide, performing a claisen condensation reaction, crystallizing and filtering after the reaction is finished to obtain dibenzoylmethane;
the composite catalyst is a mixture of p-toluenesulfonic acid and concentrated sulfuric acid, wherein the mass of the p-toluenesulfonic acid is 5-10% of the mass of the concentrated sulfuric acid, and the addition amount of the composite catalyst is 1-3% of the total mass of benzoic acid and methanol.
Preferably, the ratio of the amounts of the substances of benzoic acid and methanol is 1:4-7.
Preferably, the claisen condensation reaction is carried out at three gradient temperatures of 80-90 ℃, 130-140 ℃, 90-100 ℃.
The utility model provides a serialization preparation system of dibenzoylmethane, includes esterification reaction kettle, rectifying column, temporary storage tank and condensation tank, the lateral wall of esterification reaction kettle on be equipped with inlet pipe and inlet pipe down, lower inlet pipe set up in the liquid level below in the esterification reaction kettle, the bottom of rectifying column and the bottom of esterification reaction kettle pass through two conveying pipeline and connect, the lower part of rectifying column be equipped with and cut apart into the liquid board of controlling two parts with rectifying column bottom, the conveying pipeline of rectifying column bottom be located respectively and divide the both sides of liquid board, the top of rectifying column be connected with the condensation tank through the pipeline, temporary storage tank install on the pipeline between rectifying column and the condensation tank, the pipeline between temporary storage tank and the condensation tank on still be connected with the filling tube, last inlet pipe, lower inlet pipe, filling tube and the pipeline between filling tube and the temporary storage tank on install a feeding pump respectively.
Preferably, two partition boards for dividing the condensation tank into a first heating area, a second heating area and a third heating area are arranged in the condensation tank, the pipeline is arranged at the bottom of the first heating area, two siphon pipes are respectively arranged on the two partition boards in the condensation tank, the height of each siphon pipe between the first heating area and the second heating area is larger than that between the second heating area and the third heating area, and the temperatures of the first heating area, the second heating area and the third heating area are respectively 80-90 ℃, 130-140 ℃ and 90-100 ℃.
Preferably, the esterification reaction kettle, the first heating zone, the second heating zone and the third heating zone are all provided with reflux pipes.
Compared with the prior art, the invention has the following implementation effects:
according to the invention, the composite catalyst is used for catalyzing the reaction of benzoic acid and methanol, wherein the dosage of the organic catalyst p-toluenesulfonic acid is only 5-10% of that of the original single catalyst concentrated sulfuric acid, so that the reversibility of the p-toluenesulfonic acid is improved, the residual liquid at the bottom of the kettle containing the catalyst can be recycled, no hazardous waste is generated, and the reaction process is more environment-friendly;
according to the invention, methanol is added under the liquid level, so that the esterification reaction is complete, alkali washing and water washing are not needed, and the rectified methyl benzoate can be directly used for condensation reaction, thereby ensuring continuous production;
the invention takes dimethylbenzene as a condensation reaction solvent, adopts a mixed mode of dimethylbenzene and acetophenone to add acetophenone, and simultaneously carries out three-time gradient temperature reaction, thereby improving the reaction speed, shortening the reaction time and improving the yield of dibenzoylmethane while keeping the concentration of a reaction system in a higher state.
Drawings
Fig. 1 is a schematic diagram of the system of the present invention.
Reference numerals illustrate: 1. an esterification reaction kettle; 11. feeding a pipe; 12. a lower feed pipe; 2. a feed pump; 3. a rectifying tower; 31. a liquid separation plate; 4. a temporary storage tank; 5. a feeding tube; 6. a condensation tank; 61. a first heating zone; 62. a second heating zone; 63. a third heating zone; 7. a partition plate; 8. and (5) a return pipe.
Detailed Description
The following description of the embodiments of the present invention will be made clearly and completely with reference to the accompanying drawings, in which it is apparent that the embodiments described are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
In the description of the present invention, it should be noted that the directions or positional relationships indicated by the terms "upper", "lower", "front", "rear", "left", "right", "vertical", "inner", "outer", etc. are based on the directions or positional relationships shown in the drawings, are merely for convenience of describing the present invention and simplifying the description, and do not indicate or imply that the devices or elements to be referred to must have a specific direction to construct and operate in a specific direction, and thus should not be construed as limiting the present invention.
In the description of the present invention, it should be noted that, unless explicitly specified and limited otherwise, the terms "mounted," "connected," and "connected" are to be construed broadly, and may be either fixedly connected, detachably connected, or integrally connected, for example; can be mechanically or electrically connected; can be directly connected or indirectly connected through an intermediate medium. The specific meaning of the above terms in the present invention will be understood in specific cases by those of ordinary skill in the art.
Example 1
Taking benzoic acid and methanol as raw materials, wherein the mass ratio of the benzoic acid to the methanol is 1:4, carrying out esterification reaction for 5 hours under the catalysis of a composite catalyst of p-toluenesulfonic acid and concentrated sulfuric acid at 110 ℃, and rectifying after the reaction is finished to obtain methyl benzoate; wherein the mass of the p-toluenesulfonic acid is 5% of the mass of the concentrated sulfuric acid, and the addition amount of the composite catalyst is 2% of the total mass of the benzoic acid and the methanol.
And then, directly mixing methyl benzoate with a dimethylbenzene solution containing acetophenone and sodium methoxide, wherein the mass ratio of the methyl benzoate to the acetophenone is 3:1, the concentration of the acetophenone and the sodium methoxide in the dimethylbenzene solution is 53wt% and 1.6wt%, carrying out claisen condensation reaction after mixing, carrying out three gradient temperature reactions at 8 ℃, 130 ℃ and 100 ℃, and carrying out acid washing, alkali washing, water washing and crystallization after the reaction is finished to obtain dibenzoylmethane.
The continuous preparation system of dibenzoylmethane that this preparation method adopted includes esterification reaction kettle 1, rectifying column 3, temporary storage tank 4 and condensation tank 6, be equipped with upper inlet pipe 11 and lower inlet pipe 12 on the lateral wall of esterification reaction kettle 1, lower inlet pipe 12 sets up in the liquid level below in the esterification reaction kettle 1, the bottom of rectifying column 3 and the bottom of esterification reaction kettle 1 are connected through two conveying pipelines, the lower part of rectifying column 3 is equipped with divides liquid board 31 of dividing rectifying column 3 bottom into left and right sides two parts, the conveying pipeline of rectifying column 3 bottom is located respectively and divides liquid board 31 both sides, the top of rectifying column 3 is connected with condensation tank 6 through the pipeline, temporary storage tank 4 is installed on the pipeline between rectifying column 3 and condensation tank 6, still be connected with feed pump 2 on the pipeline between upper inlet pipe 11, lower inlet pipe 12, the conveying pipeline, feed pump 5 and feed pump 2 on the pipeline between feed pump 5 and the temporary storage tank 4, wherein the feed pump 2 on the pipeline between feed pump 5 and the temporary storage tank 4 adopts.
In addition, two partition plates 7 dividing the condensation tank 6 into a first heating zone 61, a second heating zone 62 and a third heating zone 63 are arranged in the condensation tank 6, pipelines are arranged at the bottom of the first heating zone 61, a siphon pipe is respectively arranged on the two partition plates 7 in the condensation tank 6, the height of the siphon pipe between the first heating zone 61 and the second heating zone 62 is larger than that between the second heating zone 62 and the third heating zone 63, the temperatures of the first heating zone 61, the second heating zone 62 and the third heating zone 63 are respectively 80 ℃, 130 ℃ and 100 ℃, and reflux pipes 8 are arranged on the esterification reaction kettle 1, the first heating zone 61, the second heating zone 62 and the third heating zone 63.
When the preparation system is used, benzoic acid and methanol are added into the esterification reaction kettle 1, wherein the methanol is added under the liquid level, after the esterification reaction, the solution in the esterification reaction kettle 1 is sent into the rectification tower 3 through one of the feed pumps 2 between the esterification reaction kettle 1 and the rectification tower 3 for rectification, the methanol and the benzoic acid are continuously added into the esterification reaction kettle 1, after the esterification reaction is finished again, the solution in the esterification reaction kettle 1 is sent into the rectification tower 3 through the other feed pump 2 between the esterification reaction kettle 1 and the rectification tower 3, meanwhile, the rectified base solution is pumped back into the esterification reaction kettle 1 for reuse, so that the esterification reaction and rectification can be synchronously carried out, continuous production is realized, the rectified methyl benzoate enters the temporary storage tank 4 and is pumped into the condensation tank 6 through the feed pump 2, the solution in the second heating zone 62 is added to the third heating zone 63 after the liquid level rises to the top of the siphon between the second heating zone 62 and the third heating zone 63 after the condensation in the second heating zone 62, the dibenzoylmethane solution is obtained after the third condensation, and finally the dibenzoylmethane is obtained after acid washing, alkali washing, water washing and crystallization, and the yield of the dibenzoylmethane can reach 93 percent according to the feeding amount of the acetophenone, the yield is far higher than 82% of batch production.
Although embodiments of the present invention have been shown and described, it will be understood by those skilled in the art that various changes, modifications, substitutions and alterations can be made therein without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.

Claims (2)

1. The continuous preparation method of dibenzoylmethane is characterized by comprising the following steps:
s1, using benzoic acid and methanol as raw materials, carrying out esterification reaction for 3-6 hours at 100-110 ℃ under the catalysis of a composite catalyst, and rectifying after the reaction is finished to obtain methyl benzoate;
s2, directly mixing methyl benzoate with a dimethylbenzene solution containing acetophenone and sodium methoxide, performing a claisen condensation reaction, crystallizing and filtering after the reaction is finished to obtain dibenzoylmethane;
the composite catalyst is a mixture of p-toluenesulfonic acid and concentrated sulfuric acid, wherein the mass of the p-toluenesulfonic acid is 5-10% of the mass of the concentrated sulfuric acid, and the adding amount of the composite catalyst is 1-3% of the total mass of benzoic acid and methanol;
the preparation method comprises the following steps: the device comprises an esterification reaction kettle, a rectifying tower, a temporary storage tank and a condensation tank, wherein an upper feed pipe and a lower feed pipe are arranged on the side wall of the esterification reaction kettle, the lower feed pipe is arranged below the liquid level in the esterification reaction kettle, the bottom of the rectifying tower is connected with the bottom of the esterification reaction kettle through two feed pipes, the lower part of the rectifying tower is provided with a liquid separation plate for dividing the bottom of the rectifying tower into a left part and a right part, the feed pipes at the bottom of the rectifying tower are respectively positioned at two sides of the liquid separation plate, the top of the rectifying tower is connected with the condensation tank through pipelines, the temporary storage tank is arranged on the pipeline between the rectifying tower and the condensation tank, a feed pipe is also connected on the pipeline between the temporary storage tank and the condensation tank, and a feed pump is respectively arranged on the pipelines between the upper feed pipe, the lower feed pipe, the feed pipe and the temporary storage tank;
the condensing tank is internally provided with two partition boards for dividing the condensing tank into a first heating area, a second heating area and a third heating area, the pipeline is arranged at the bottom of the first heating area, two partition boards in the condensing tank are respectively provided with a siphon pipe, the height of the siphon pipe between the first heating area and the second heating area is larger than that between the second heating area and the third heating area, and the temperatures of the first heating area, the second heating area and the third heating area are respectively 80-90 ℃, 130-140 ℃ and 90-100 ℃;
and return pipes are arranged on the esterification reaction kettle, the first heating zone, the second heating zone and the third heating zone.
2. The continuous process for the preparation of dibenzoylmethane according to claim 1, characterized in that the ratio of the amounts of benzoic acid and methanol is 1:4-7.
CN202110707833.1A 2021-06-24 2021-06-24 Continuous preparation method and system of dibenzoylmethane Active CN113620796B (en)

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JPS59163338A (en) * 1983-03-08 1984-09-14 Teijin Ltd Production of aromatic carboxylic acid
US5015777A (en) * 1989-11-02 1991-05-14 Witco Corporation Process for the preparation of aromatic beta-diketones
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CN104803848A (en) * 2015-04-23 2015-07-29 安徽佳先功能助剂股份有限公司 Method for producing methyl benzoate using benzoic acid containing sodium chloride as raw materials
CN110818543A (en) * 2018-08-09 2020-02-21 山东瑞丰高分子材料股份有限公司燕崖分公司 Novel method for efficiently synthesizing dibenzoyl methane

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