CN106748677A - Take support type acidic ion liquid as the method for catalyst preparation diethoxymethane - Google Patents
Take support type acidic ion liquid as the method for catalyst preparation diethoxymethane Download PDFInfo
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- CN106748677A CN106748677A CN201611131871.2A CN201611131871A CN106748677A CN 106748677 A CN106748677 A CN 106748677A CN 201611131871 A CN201611131871 A CN 201611131871A CN 106748677 A CN106748677 A CN 106748677A
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- formaldehyde
- diethoxymethane
- ethanol
- catalyst
- bed reactor
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/48—Preparation of compounds having groups
- C07C41/50—Preparation of compounds having groups by reactions producing groups
- C07C41/56—Preparation of compounds having groups by reactions producing groups by condensation of aldehydes, paraformaldehyde, or ketones
-
- 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
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
- B01J31/0281—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member
- B01J31/0282—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member of an aliphatic ring, e.g. morpholinium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/48—Preparation of compounds having groups
- C07C41/58—Separation; Purification; Stabilisation; Use of additives
-
- 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
- B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
- B01J2231/4277—C-X Cross-coupling, e.g. nucleophilic aromatic amination, alkoxylation or analogues
- B01J2231/4288—C-X Cross-coupling, e.g. nucleophilic aromatic amination, alkoxylation or analogues using O nucleophiles, e.g. alcohols, carboxylates, esters
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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)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Abstract
The present invention discloses a kind of method with support type acidic ion liquid as catalyst preparation diethoxymethane, belongs to Organic Chemicals synthesis technical field.Using formaldehyde and ethanol raw material, with support type acidic ion liquid as catalyst, in the technique that fluidized-bed reactor synthesizes diethoxymethane.Formaldehyde and ethanol are respectively through measuring pump, after preheater gasification, blended device is sufficiently mixed two kinds of raw materials, squeeze into and be pre-loaded with supported acidic ionic-liquid catalyst and be warming up in 80 100 DEG C of series fluidized bed reactor, keep the MPa of pressure 0.1 1.0, the residence time be 5 10min, after by gas-liquid separator, unreacted formaldehyde is reclaimed, to recycle；Restructuring lease making adsorption tower, the moisture of adsorption reaction generation, then separates diethoxymethane and a small amount of ethanol by rectifying column.Present invention process has the advantages that energy consumption is low, invest small, ethanol conversion and selectivity height, catalyst efficiency high, service life cycle long, environment-friendly, high degree of automation, safe.
Description
Technical field
The present invention relates to a kind of method with support type acidic ion liquid as catalyst preparation diethoxymethane, especially
It is related to a kind of method that diethoxymethane is prepared with support type acidic ion liquid as catalyst, under temperate condition, belonging to
Compound synthesis technical field.
Background technology
88 DEG C of diethoxymethane (Diethoxymethane, DEM) boiling point, energy azeotrope with water, and have relatively low with water
Affinity.In recent years, DEM shows the performance of uniqueness in organic synthesis field, under the conditions of popular response, can stablize and deposit
, or even after the completion of alkali metal reaction, without drying.DEM is likely to become tetrahydrofuran（THF）, dichloromethane
（CH2Cl2）, glycol dimethyl ether（1,2-dimethoxyethane）, dimethoxym ethane（1,1-dimethoxymethane）Equal solvent
Potential substitute, or even be expected to turn into new generation environmental type oxo solvent in the future, instead of engine fuel.In recent years
Come, its demand increases into geometric progression amount, by scientific worker and the extensive concern of business circles.
Patent application CN103739462A " a kind of preparation method of diethoxymethane ", discloses one kind ethylenediamine tetraacetic
Acetic acid and malic acid combination catalyst, formaldehyde and ethanol prepare diethoxymethane technique for raw material.But its reaction time is
2.5h, the reaction time is more long, and catalyst efficiency is not high.
Patent application CN105585462A " a kind of method for preparing diethoxymethane ", discloses using dimethoxy first
Alkane and ethanol are raw material, with liquid acid and support type liquid acid as catalyst, the technique for preparing diethoxymethane.But used by it
Acid be Compound-acid, sulfuric acid, hydrofluoric acid, hydrochloric acid etc. are higher to equipment corrosion, and cost of investment is high, can exist in industrialization a lot
Problem.
Patent application CN102206145A " a kind of continuous catalyzing rectifying synthesis technique of diethoxymethane ", disclose with
Formaldehyde and ethanol are raw material, the technique that diethoxymethane is catalyzed and synthesized using the linkage of two-part rectifying column, wherein in rectifying column
What is loaded is solid acid catalyst.But its process operation temperatures is higher, solid acid catalyst is easily dissolved in rectifying column, and pollution is produced
Thing, difficulty is brought to follow-up separation process.
The content of the invention
The invention aims to solve it is existing synthesis diethoxymethane technology in, there is high energy consumption, catalyst makes
Temperature is high, high to equipment requirement, the shortcomings of cost of investment is big, there is provided one kind is with support type acidic ion liquid as catalyst system
The method of standby diethoxymethane, cleaning, safe, environment-friendly, low energy consumption, small investment, can continuously produce, stable performance.
A kind of is the method for catalyst preparation diethoxymethane with support type acidic ion liquid, is comprised the following steps：
（1）In advance in the fluidized-bed reactor load type acidic ionic liquid catalysts of series connection；
（2）Preheated fluidification bed reactor is warming up to 80-100 DEG C simultaneously；
（3）Formaldehyde and ethanol respectively through measuring pump, then it is preheated after to 80-90 DEG C, blended device is sufficiently mixed squeezes into fluidisation
In bed reactor；
（4）The mass ratio for keeping ethanol and formaldehyde in step (3) is 1:1-3:1, flow velocity is 3-7kg/h；
（5）By adjusting the outlet valve of fluidized-bed reactor, holding pressure is 0.1-1.0MPa, material is contacted with catalyst
Time be 5-10min；
（6）By step（5）Product is obtained after gas-liquid separation, light component formaldehyde is recycled；Restructuring lease making adsorption tower absorption water
After point, target product diethoxymethane is obtained into rectifying assembling device, after separation.
The structural formula of described support type acidic ion liquid is：
。
The carrier of the catalyst is aluminum oxide molecular sieve, and particle mean size 2-3 ㎜, compression strength is more than 100N/, heap density
0.4-1g/ml。
Described fluidized-bed reactor is four fluidized-bed reactors of series connection.
Adsorbent in the adsorption tower is aluminum oxide spheroidal adsorbent, granularity 4-5mm, water absorption rate 70-80%.
Simple production process, operation temperature pressure in the present invention is low, with energy consumption is low, ethanol conversion and selectivity
Height, catalyst efficiency high, service life cycle are long, environment-friendly, clean, accessory substance is few, waste water is few, the advantages of safe,
It is easy to utilize.
Brief description of the drawings
Fig. 1 is process chart of the invention,
Wherein shown in icon：Formaldehyde Tank 1, ethanol storage tank 2, formaldehyde measuring pump 3, ethanol measuring pump 4, formaldehyde preheater 5, ethanol
Preheater 6, blender 7, the first series fluidized bed reactor 8, the second series fluidized bed reactor the 9, the 3rd are series fluidized bed anti-
Answer device 10, the 4th series fluidized bed reactor 11, gas-liquid separation device 12, formaldehyde circulating line 13, liquid composition feed pump 14,
Water adsorption tower 15, feed pump 16, rectifying column 17, diethoxymethane storage tank 18, ethanol circulating line 19.
Specific embodiment
Formaldehyde, ethanol after fully mixed, are squeezed into reactor according to certain mass ratio in the present invention, are closed
Into diethoxymethane.In order to improve the conversion ratio of ethanol, using excessive formaldehyde, mass ratio is 1:1-3:1, flow velocity is 3-
7kg/h, reactor pressure is 0.1-1.0MPa, and temperature is 80-100 DEG C, and material is 5-10min with catalyst contact time；Instead
After the completion of answering, by gas-liquid separation tower, excessive formaldehyde is separated；Added adsorption tower, the moisture of adsorption reaction generation；Then rectifying
Obtain product.The method has simple to operate, easily realizes Automated condtrol, and energy consumption is low, the advantages of ethanol conversion is high.
Reaction principle is as follows：
The catalyst for using is support type acidic ion liquid, and structural formula is：
Below in conjunction with accompanying drawing 1 and embodiment 1-6, the invention will be further described.
Reaction system as shown in figure 1, formaldehyde raw material is connected by principal goods pipe material with formaldehyde feed pump 3 in Formaldehyde Tank 1,
Formaldehyde preheater 5 is delivered to preheat；Ethanol raw material in ethanol storage tank 2 is connected by principal goods pipe material with ethanol feed pump 4, is delivered to
Ethanol preheater 6 is preheated；After two strands of materials mix at blender 7, automatically into fluidized-bed reactor under the promotion of pressure
（8-11）；Gas-liquid separation device 12 is connected with the bottom of the 4th fluidized-bed reactor 11；Gas formaldehyde after separation is followed through pipeline 13
Ring enters Formaldehyde Tank；Restructuring lease making liquid composition feed pump 14 is connected with water adsorption tower 15；Rectifying column 17 and feed pump 16
It is connected；Rectifying light component ethanol is circulated through ethanol circulating line 19；Diethoxymethane storage tank 18 is connected with rectifying column 17.
The carrier of the catalyst is aluminum oxide molecular sieve, and particle mean size 2-3 ㎜, compression strength is more than 100N/, and heap is close
Degree 0.4-1g/ml.
Adsorbent in the adsorption tower is aluminum oxide spheroidal adsorbent, granularity 4-5mm, water absorption rate 70-80%.
Embodiment 1
Support type acidic ionic liquid catalysts are filled in 4 fluidized-bed reactors of series connection in advance, is loaded in adsorption tower
Adsorbent.Each temperature-controlling system, instrument and the valve of pilot-plant have been debugged, and with the air in nitrogen displacement system, while entering
Row leak detection.Formaldehyde preheater 5, the temperature adjustment of ethanol preheater 6 are to 80 DEG C；4 reactors are heated simultaneously to 100 DEG C；Start formaldehyde meter
Amount pump 3, ethanol measuring pump 4, it is 1 with the mass ratio of ethanol to keep formaldehyde:1, exit velocity is 4kg/h after mixing；By regulation
Reactor outlet valve opening, regulation material is 5min by the beds time；By adsorption tower adsorption moisture, rectifying is separated
Diethoxymethane is obtained, gas chromatographic detection purity is 99.8%.
Embodiment 2
Support type acidic ionic liquid catalysts are filled in 4 fluidized-bed reactors of series connection in advance, is loaded in adsorption tower
Adsorbent.Each temperature-controlling system, instrument and the valve of pilot-plant have been debugged, and with the air in nitrogen displacement system, while entering
Row leak detection.Formaldehyde preheater 5, the temperature adjustment of ethanol preheater 6 are to 90 DEG C；4 reactors are heated simultaneously to 80 DEG C；Start formaldehyde metering
Pump 3, ethanol measuring pump 4, it is 2 with the mass ratio of ethanol to keep formaldehyde:1, exit velocity is 3kg/h after mixing；It is anti-by regulation
Device is answered to export valve opening, regulation material is 8min by the beds time；By adsorption tower adsorption moisture, rectifying is separated
To diethoxymethane, gas chromatographic detection purity is 99.5%.
Embodiment 3
Support type acidic ionic liquid catalysts are filled in 4 fluidized-bed reactors of series connection in advance, is loaded in adsorption tower
Adsorbent.Each temperature-controlling system, instrument and the valve of pilot-plant have been debugged, and with the air in nitrogen displacement system, while entering
Row leak detection.Formaldehyde preheater 5, the temperature adjustment of ethanol preheater 6 are to 80 DEG C；4 reactors are heated simultaneously to 100 DEG C；Start formaldehyde meter
Amount pump 3, ethanol measuring pump 4, it is 3 with the mass ratio of ethanol to keep formaldehyde:1, exit velocity is 5kg/h after mixing；By regulation
Reactor outlet valve opening, regulation material is 7min by the beds time；By adsorption tower adsorption moisture, rectifying is separated
Diethoxymethane is obtained, gas chromatographic detection purity is 99.3%.
Embodiment 4
Support type acidic ionic liquid catalysts are filled in 4 fluidized-bed reactors of series connection in advance, is loaded in adsorption tower
Adsorbent.Each temperature-controlling system, instrument and the valve of pilot-plant have been debugged, and with the air in nitrogen displacement system, while entering
Row leak detection.Formaldehyde preheater 5, the temperature adjustment of ethanol preheater 6 are to 90 DEG C；4 reactors are heated simultaneously to 90 DEG C；Start formaldehyde metering
Pump 3, ethanol measuring pump 4, it is 2 with the mass ratio of ethanol to keep formaldehyde:1, exit velocity is 3kg/h after mixing；It is anti-by regulation
Device is answered to export valve opening, regulation material is 5min by the beds time；By adsorption tower adsorption moisture, rectifying is separated
To diethoxymethane, gas chromatographic detection purity is 99.6%.
Embodiment 5
Support type acidic ionic liquid catalysts are filled in 4 fluidized-bed reactors of series connection in advance, is loaded in adsorption tower
Adsorbent.Each temperature-controlling system, instrument and the valve of pilot-plant have been debugged, and with the air in nitrogen displacement system, while entering
Row leak detection.Formaldehyde preheater 5, the temperature adjustment of ethanol preheater 6 are to 90 DEG C；4 reactors are heated simultaneously to 100 DEG C；Start formaldehyde meter
Amount pump 3, ethanol measuring pump 44, it is 3 with the mass ratio of ethanol to keep formaldehyde:1, exit velocity is 3kg/h after mixing；By regulation
Reactor outlet valve opening, regulation material is 6min by the beds time；By adsorption tower adsorption moisture, rectifying is separated
Diethoxymethane is obtained, gas chromatographic detection purity is 98.9%.
Embodiment 6
Support type acidic ionic liquid catalysts are filled in 4 fluidized-bed reactors of series connection in advance, is loaded in adsorption tower
Adsorbent.Each temperature-controlling system, instrument and the valve of pilot-plant have been debugged, and with the air in nitrogen displacement system, while entering
Row leak detection.Formaldehyde preheater 5, the temperature adjustment of ethanol preheater 6 are to 80 DEG C；4 reactors are heated simultaneously to 100 DEG C；Start formaldehyde meter
Amount pump 3, ethanol measuring pump 4, it is 3 with the mass ratio of ethanol to keep formaldehyde:1, exit velocity is 7kg/h after mixing；By regulation
Reactor outlet valve opening, regulation material is by beds time 10min；By adsorption tower adsorption moisture, rectifying is separated
Diethoxymethane is obtained, gas chromatographic detection purity is 99.1%.
Claims (5)
1. a kind of method with support type acidic ion liquid as catalyst preparation diethoxymethane, it is characterised in that：Including
Following steps：
（1）In advance in the fluidized-bed reactor load type acidic ionic liquid catalysts of series connection；
（2）Preheated fluidification bed reactor is warming up to 80-100 DEG C simultaneously；
（3）Formaldehyde and ethanol respectively through measuring pump, then it is preheated after to 80-90 DEG C, blended device is sufficiently mixed squeezes into fluidisation
In bed reactor；
（4）The mass ratio for keeping ethanol and formaldehyde in step (3) is 1:1-3:1, flow velocity is 3-7kg/h；
（5）By adjusting the outlet valve of fluidized-bed reactor, holding pressure is 0.1-1.0MPa, material is contacted with catalyst
Time be 5-10min；
（6）By step（5）Product is obtained after gas-liquid separation, light component formaldehyde is recycled；Restructuring lease making adsorption tower absorption water
After point, target product diethoxymethane is obtained into rectifying assembling device, after separation.
2. the method for claim 1, it is characterised in that：The structural formula of described support type acidic ion liquid is：
。
3. the method for claim 1, it is characterised in that：The carrier of the catalyst is aluminum oxide molecular sieve, average grain
Degree 2-3 ㎜, compression strength is more than 100N/, heap density 0.4-1g/ml.
4. the method for claim 1, it is characterised in that：Described fluidized-bed reactor is that the fluid bed of four series connection is anti-
Answer device.
5. the method for claim 1, it is characterised in that：Adsorbent in the adsorption tower is the absorption of aluminum oxide ball-type
Agent, granularity 4-5mm, water absorption rate 70-80%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201611131871.2A CN106748677A (en) | 2016-12-09 | 2016-12-09 | Take support type acidic ion liquid as the method for catalyst preparation diethoxymethane |
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| CN201611131871.2A CN106748677A (en) | 2016-12-09 | 2016-12-09 | Take support type acidic ion liquid as the method for catalyst preparation diethoxymethane |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114920628A (en) * | 2022-03-30 | 2022-08-19 | 江西浩普海诚新材料有限公司 | Continuous method for preparing dialkoxy methane compound by reactor series dehydration membrane |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103965029A (en) * | 2013-01-30 | 2014-08-06 | 李云勇 | Production method of dibutoxymethane, diethoxymethane, dipropoxymethane or dipentyloxymethane |
| CN104045530A (en) * | 2014-05-15 | 2014-09-17 | 上海盘马化工工程技术有限公司 | System using supported ionic liquid catalyst for continuous preparation of polyoxymethylene dimethyl ether |
-
2016
- 2016-12-09 CN CN201611131871.2A patent/CN106748677A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103965029A (en) * | 2013-01-30 | 2014-08-06 | 李云勇 | Production method of dibutoxymethane, diethoxymethane, dipropoxymethane or dipentyloxymethane |
| CN104045530A (en) * | 2014-05-15 | 2014-09-17 | 上海盘马化工工程技术有限公司 | System using supported ionic liquid catalyst for continuous preparation of polyoxymethylene dimethyl ether |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114920628A (en) * | 2022-03-30 | 2022-08-19 | 江西浩普海诚新材料有限公司 | Continuous method for preparing dialkoxy methane compound by reactor series dehydration membrane |
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Application publication date: 20170531 |