CN101863761A - Method for preparing dipropylene glycol methyl ether acetate - Google Patents
Method for preparing dipropylene glycol methyl ether acetate Download PDFInfo
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- CN101863761A CN101863761A CN201010213655A CN201010213655A CN101863761A CN 101863761 A CN101863761 A CN 101863761A CN 201010213655 A CN201010213655 A CN 201010213655A CN 201010213655 A CN201010213655 A CN 201010213655A CN 101863761 A CN101863761 A CN 101863761A
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- dipropylene glycol
- methyl ether
- glycol methyl
- ether acetate
- esterification
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Abstract
The invention discloses a process for preparing dipropylene glycol methyl ether acetate, which uses dipropylene glycol monomethyl ether and acetic acid as raw materials. The process is characterized in that: performing a fixed bed continuous esterification reaction in the presence of a solid acid catalyst at an esterification temperature of 70 to 150 DEG and removing the water generated by the esterification reaction by azeotropic distillation; distilling the product of the esterification reaction, removing and recovering unreacted dipropylene glycol monomethyl ether and acetic acid, and obtaining the dipropylene glycol methyl ether acetate. The method of the invention realizes the continuous production of the dipropylene glycol methyl ether acetate, is simple in operation mode, obviously improves the production efficiency of the dipropylene glycol methyl ether acetate, reduces the production cost of the dipropylene glycol methyl ether acetate, can reduce solid pollutants and waste water discharge and has high scale industrial application values.
Description
Technical field
The present invention relates to a kind of preparation method of dipropylene glycol methyl ether acetate, especially be particularly related to the method that a kind of continuous esterification prepares dipropylene glycol methyl ether acetate.
Background technology
Dipropylene glycol methyl ether acetate (DPMA) is the important industrial solvent of a class, this solvent molecule structure uniqueness, with existing nonpolar part in a part, polar group is arranged again, so it all has dissolving power preferably to polarity and apolar substance, its solubility property is much higher than common solvent and propylene glycol ethers and glycol ethers solvent.Change little and characteristics such as corrodibility is little because dipropylene glycol methyl ether acetate has solvent nature height, Heat stability is good, viscosity, be widely used in industry such as coating, washing composition, printing and dyeing, agricultural chemicals and pluronic polymer.
By dipropylene glycol methyl ether and acetic acid through esterification system dipropylene glycol methyl ether acetate, though be general technological line, but the at present industrial method that generally adopts is an intermittent type esterification dehydration reaction technology, the catalyzer that uses in the reaction process is generally mineral acid or organic acid, and mineral acid is mainly: phosphoric acid, hydrochloric acid, the vitriol oil and chlorsulfonic acid; Organic acid is mainly: oxalic acid, citric acid, methylsulfonic acid and tosic acid, take homogeneous reaction (Liu Zhun etc., Chinese patent CN1515537A, on July 28th, 2004; Zhu Xinbao etc., CN101475469A, on July 8th, 2009).The problem that aforesaid method exists is, need after reaction finishes by removing employed catalyzer in the alkali, and this method side reaction is many, corrodibility strong, complex technical process, production efficiency is low, generation is a large amount of solid waste and contaminated wastewater environment.The heteropllyacids of employing solid acid catalyst (Wang Xi is also arranged, Liaoning teachers training school journal: natural science edition, 2000 the 2nd the 1st phases of volume) be used for propylene-glycol ether acetate synthetic report, but all multifactor considerations such as complicacy from the The Nomenclature Composition and Structure of Complexes of heteropolyacid own and work-ing life are bigger in industrial practical application difficulty.Employing modified molecular screen class composite solid-acid catalysts such as Chen Yuandong also add auxiliary agent (Chinese patent CN1048990A such as metallic tin compound, on February 6th, 1991) carry out esterification, it is said and to reduce esterification reaction temperature, react 2-3 hour transformation efficiency near 100%.But the contained tin compound auxiliary agent of this type of solid acid catalyst has big toxicity and runs off easily, and apparent, its actual application and popularization value can be subjected to bigger restriction undoubtedly.
Summary of the invention
The object of the invention is to provide a kind of preparation method of dipropylene glycol methyl ether acetate, this method can overcome the existing product of existing batch production technology to be needed through neutralizing treatment, and complex technical process, production efficiency low, produce shortcomings such as a large amount of solid waste and waste water, realize the serialization production of dipropylene glycol methyl ether acetate, improve the production efficiency of dipropylene glycol methyl ether acetate, reduce its production cost.
The technical solution adopted in the present invention is as follows:
A kind of method for preparing dipropylene glycol methyl ether acetate, with dipropylene glycol methyl ether and acetic acid is raw material, it is characterized in that: adopt solid acid catalyst to carry out the fixed bed continuous esterification, esterification temperature 70-150 ℃, the water that generates in the esterification removes through component distillation; With esterification reaction product rectifying, remove and reclaim unreacted dipropylene glycol methyl ether and acetic acid, obtain dipropylene glycol methyl ether acetate.
Described solid acid catalyst is a kind of composite enhanced macroporous polystyrene sulfonic acid type storng-acid cation exchange resin.Described Zeo-karb polymkeric substance can adopt the common synthetic method of polystyrolsulfon acid type storng-acid cation exchange resin, and soon sulfonation makes behind vinylbenzene and the Vinylstyrene monomer polymerization.The mole number of Vinylstyrene accounts for 20～35% in its polymerization single polymerization monomer of described Zeo-karb, and adding weight accounts for the micron order graphite whisker of polymerization single polymerization monomer total amount 1～3% (wt/wt) and the pore-creating agent of polymerization single polymerization monomer total amount 40～70% (wt/wt).Described pore-creating agent comprises toluene, dimethylbenzene, gasoline, normal heptane, octane-iso, isooctyl alcohol or 2-ethyl butanol etc., or their mixture.Add composite pore-forming, can make the ion exchange resin that obtains have the equally distributed basically aperture of macropore, mesopore, aperture, thereby improve intensity, thermostability and the specific surface area of catalyst backbone greatly.Through the actual trial run that investigate and carry out on full scale plant the work-ing life on the pilot plant, the work-ing life of described solid acid catalyst is at least more than 1 year.
Described fixed bed continuous esterification can adopt the two-part fixed bed to carry out continuous esterification, promptly carries out two sections esterifications continuously in two fixed-bed reactor that all are filled with described solid acid catalyst.In view of esterification is the reversible reaction that is subjected to thermodynamics equilibrium limit, carry out to the direction of expectation for helping esterification, after first section esterification reaction product removes the water of reaction generation, carry out second section esterification again, to obtain higher transformation efficiency.Specific practice is, earlier raw material dipropylene glycol methyl ether and acetic acid mixed by certain mole proportioning, carries out esterification through entering first section fixed-bed reactor that solid acid catalyst is housed continuously after the preheating, and reaction product enters the distillation tower dehydration; Material after the dehydration is extracted out continuously in distillation tower stripping section bottom, and delivers in second section fixed-bed reactor as the charging of second section esterification and to proceed esterification.Entering the raw material dipropylene glycol methyl ether of first section fixed-bed reactor and the mol ratio of acetic acid is 0.7-2: 1, and preferable range is 0.9-1.2: 1; The mass flow of extracting and be input to second section fixed-bed reactor out at the distillation tower stripping section be first section fixed-bed reactor inlet amount 1-5 doubly, preferable range be 2-3 doubly.Equally, the product of second section esterification enters the distillation tower dehydration again after the reaction product with first section esterification merges.
In described two fixed-bed reactor, first section esterification reaction temperature is 70-150 ℃, and preferable range is 80-110 ℃; Air speed is 1-5h
-1, preferable range is 3-4h
-1Second section esterification reaction temperature is 70-150 ℃, and preferable range is 105-140 ℃; Air speed is 5-10h
-1, preferable range is 6-8h
-1
The water that esterification generated removes in the component distillation mode in distillation tower, and the band aqua that is adopted is benzene or hexanaphthene.First section reaction product with second section esterification enters distillation tower and carries out component distillation from top, forming water steams from the distillation tower cat head with the azeotrope of being with aqua, after condenser condenses, enter the layering jar, and in the layering jar, be divided into organic phase and water, lower floor's water is drawn, and upper organic phase is back to distillation tower and uses for the band aqua.
Unreacted dipropylene glycol methyl ether, acetic acid and with object esterification products dipropylene glycol methyl ether acetate by discharging at the bottom of the distillation tower still, enter lightness-removing column rectifying, the lighting end that cat head steams is dipropylene glycol methyl ether and acetic acid, with its recovery.The dipropylene glycol methyl ether and the acetic acid that reclaim can be used as the reaction raw materials cycling and reutilization.Lightness-removing column bottoms material is the object dipropylene glycol methyl ether acetate.
Through the prepared product of aforesaid method is the dipropylene glycol methyl ether acetate crude product.The lightness-removing column bottom product is delivered to the rectifying of product rectifying tower, can obtain the pure product of dipropylene glycol methyl ether acetate.
Fig. 1 prepares the schema of the main part of dipropylene glycol methyl ether acetate technology for two sections fixed bed continuous esterifications that adopt solid acid catalyst.
In Fig. 1,
1For first section fixed-bed reactor of solid acid catalyst are housed,
2For second section fixed-bed reactor of solid acid catalyst are housed,
3Be distillation tower,
4Be condenser,
5Be the layering jar,
6Be first section fixed-bed reactor feeding pipe position,
7Be second section fixed-bed reactor feeding pipe position,
8For the esterification material enters distillation tower pipeline position,
9Be the water outlet,
10Be the band aqua into distillation tower pipeline position of refluxing,
11For distillation Tata still material is sent to the lightness-removing column pipeline.
Dipropylene glycol methyl ether and acetic acid raw material after preheating by
6Enter first section fixed-bed reactor that solid acid catalyst is housed
1, propylene glycol monomethyl ether and acetic acid generation esterification under catalyst action are carried out for helping the esterification forward direction, improve transformation efficiency, with the reaction mass of first section fixed-bed reactor by
8Send distillation tower to
3Dehydration.At distillation tower
3In, the water that esterification generates is constantly gone out from cat head is separated in 68-71 ℃ of formation azeotrope in the presence of band aqua of the present invention.The esterification material is drawn out of in distillation tower stripping section bottom continuously through the dehydration back, by
7Deliver to second section fixed-bed reactor
2Proceed esterification.The mass flow of extracting and be input to second section fixed-bed reactor out at the distillation tower stripping section be first section fixed-bed reactor inlet amount 1-5 doubly, preferable range be 2-3 doubly.Through the material of second section fixed-bed reactor reaction equally by
8Enter distillation tower
3Separation removal moisture.Distillation tower
3Cat head steams thing through condenser
4After the condensation, enter the layering jar
5, and at the layering jar
5In be divided into organic phase and water, lower floor's water from
9Draw, upper organic phase is the band aqua, by
10Be back to distillation tower
3Dipropylene glycol methyl ether acetate and unreacted dipropylene glycol methyl ether and acetic acid that esterification generates are by distillation tower
3Discharging warp at the bottom of the still
11Enter lightness-removing column (not marking among Fig. 1) rectifying of other outfit, dipropylene glycol methyl ether and acetic acid that the lightness-removing column top steams reclaim Recycling, the thick product of dipropylene glycol methyl ether acetate at the bottom of the lightness-removing column still is delivered to product rectifying tower (not marking among Fig. 1) rectifying, obtains the pure product of dipropylene glycol methyl ether acetate.
In sum, the production method of dipropylene glycol methyl ether acetate of the present invention, novel process by serialization production, can realize the suitability for industrialized production of dipropylene glycol methyl ether acetate product expeditiously, and operating method is simple, production efficiency is high, reduces the discharging of slag and effluent in production process; Reaction product need not a large amount of alkali and neutralizes, the long service life of catalyzer, and the products production cost reduces.Continuous esterification of the present invention prepares the method for dipropylene glycol methyl ether acetate, and good economic benefit and environmental benefit are arranged.
Describe the present invention below in conjunction with specific embodiment.Scope of the present invention is not exceeded with embodiment, but is limited by the scope of claim.
Description of drawings
Fig. 1 continuous esterification prepares the process flow diagram of dipropylene glycol methyl ether acetate
Technical process as shown in Figure 1, to be preheated to 110 ℃ raw material dipropylene glycol methyl ether and acetic acid 1: 1 in molar ratio, import first section fixed-bed reactor 1 that 5L macroporous polystyrene sulfonic acid type storng-acid cation exchange resin solid acid catalyst is housed continuously with the 15L/h flow, 110 ℃ of esterification reaction temperatures, air speed are 3h
-1Material through first section fixed-bed reactor 1 reaction enters distillation tower 3, and in distillation tower 3, the water that esterification generates is in the presence of water liquid benzene, in 68-71 ℃ of formation azeotrope and constantly separated.The material that is removed moisture is drawn out of and is transported to second section fixed-bed reactor 2 that the above-mentioned solid acid catalyst of 5L is housed continuously at the stripping section of distillation tower 3 and proceeds esterification with the 30L/h flow, 120 ℃ of temperature of reaction, air speed are 6h
-1The mass flow that is input to second section fixed-bed reactor is 2 times of first section fixed-bed reactor 1 inlet amount.Material through 2 reactions of second section fixed-bed reactor enters distillation tower 3 separation removal moisture equally, distillation tower 3 cats head steam thing after condenser 4 condensations, enter layering jar 5, and in layering jar 5, be divided into organic phase and water, water is drawn, and organic phase is that water liquid benzene is back to distillation tower 3 and uses.Mass ratio is formed in distillation tower 3 tower still dischargings: dipropylene glycol methyl ether acetate 57.8%, acetic acid 12.2%, dipropylene glycol methyl ether 30.0%.Distillation tower 3 tower still dischargings enter the lightness-removing column rectifying of other outfit, and the dipropylene glycol methyl ether that cat head steams and acetic acid reclaim Recycling, and tower still material is delivered to product rectifying tower purifying, but output dipropylene glycol methyl ether acetate product 8kg per hour.
Technical process as shown in Figure 1, to be preheated to 95 ℃ raw material dipropylene glycol methyl ether and acetic acid 1.5: 1 in molar ratio, import first section fixed-bed reactor 1 that 5L macroporous polystyrene sulfonic acid type storng-acid cation exchange resin solid acid catalyst is housed continuously with the 20L/h flow, 95 ℃ of esterification reaction temperatures, air speed are 4h
-1Material through first section fixed-bed reactor 1 reaction enters distillation tower 3, and in distillation tower 3, the water that esterification generates is in the presence of hexanaphthene band aqua, in 69-71 ℃ of formation azeotrope and constantly separated.The esterification material that removes moisture is extracted and is transported to out second section fixed-bed reactor 2 that the above-mentioned solid acid catalyst of 5L is housed at the stripping section of distillation tower 3 continuously with the 40L/h flow, 105 ℃ of esterification reaction temperatures, and air speed is 8h
-1The mass flow that is input to second section fixed-bed reactor 2 is 2 times of first section fixed-bed reactor 1 inlet amount.Material through 2 reactions of second section fixed-bed reactor enters distillation tower 3 separation removal moisture equally, and distillation tower 3 cats head steam thing after condenser 4 condensations, enter layering jar 5, and in layering jar 5, be divided into organic phase and water, water is drawn, and organic phase is a hexanaphthene, turns back to distillation tower 3.Distillation tower 3 tower still dischargings consist of: dipropylene glycol methyl ether acetate 49.5%, acetic acid 6.7%, dipropylene glycol methyl ether 43.8%.Distillation tower 3 tower still dischargings enter the lightness-removing column fractionation of other outfit, and the dipropylene glycol methyl ether that cat head steams and acetic acid reclaim Recycling, and tower still material is got to the rectifying of product rectifying tower, but output dipropylene glycol methyl ether acetate product 9.2kg per hour.
Claims (10)
1. method for preparing dipropylene glycol methyl ether acetate, with dipropylene glycol methyl ether and acetic acid is raw material, it is characterized in that: adopt solid acid catalyst to carry out the fixed bed continuous esterification, esterification temperature 70-150 ℃, the water that generates in the esterification removes through component distillation; With esterification reaction product rectifying, remove and reclaim unreacted dipropylene glycol methyl ether and acetic acid, obtain dipropylene glycol methyl ether acetate.
2. the method for preparing dipropylene glycol methyl ether acetate according to claim 1 is characterized in that: described solid acid catalyst is composite enhanced macroporous polystyrene sulfonic acid type storng-acid cation exchange resin.
3. the method for preparing dipropylene glycol methyl ether acetate according to claim 2, it is characterized in that: described ion exchange resin by vinylbenzene and Vinylstyrene monomer polymerization after sulfonation make, the mole number of Vinylstyrene accounts for 20～35% in its polymerization single polymerization monomer, and adding weight accounts for the micron order graphite whisker of polymerization single polymerization monomer total amount 1～3% (wt/wt) and the pore-creating agent of monomer total amount 40～70% (wt/wt).
4. the method for preparing dipropylene glycol methyl ether acetate according to claim 1 and 2, it is characterized in that: described fixed bed continuous esterification, be all to be filled with two sections esterifications of carrying out continuously in the fixed-bed reactor of solid acid catalyst at two, first section esterification reaction product carries out second section esterification after removing and reacting the water that generates.
5. the method for preparing dipropylene glycol methyl ether acetate according to claim 4, it is characterized in that: described fixed bed continuous esterification comprises, after raw material dipropylene glycol methyl ether and acetic acid mix also preheating, enter first section fixed-bed reactor that solid acid catalyst is housed continuously and carry out esterification, reaction product enters the distillation tower dehydration; Material after the dehydration is extracted out continuously in distillation tower stripping section bottom, and delivers in second section fixed-bed reactor as the charging of second section esterification and to proceed esterification.
6. the method for preparing dipropylene glycol methyl ether acetate according to claim 4 is characterized in that: entering the raw material dipropylene glycol methyl ether of first section fixed-bed reactor and the mol ratio of acetic acid is 0.7-2: 1; The mass flow that enters into second section fixed-bed reactor is 1-5 a times of first section fixed-bed reactor inlet amount.
7. the method for preparing dipropylene glycol methyl ether acetate according to claim 4 is characterized in that: first section esterification reaction temperature is 80-110 ℃; Second section esterification reaction temperature is 105-140 ℃.
8. the method for preparing dipropylene glycol methyl ether acetate according to claim 4 is characterized in that: the esterification air speed of described first section fixed-bed reactor is 1-5h
-1The esterification air speed of second section fixed-bed reactor is 5-10h
-1
9. the method for preparing dipropylene glycol methyl ether acetate according to claim 1 and 2 is characterized in that: the band aqua that described component distillation adopts is benzene or hexanaphthene.
10. the method for preparing dipropylene glycol methyl ether acetate according to claim 1 and 2 is characterized in that: the dipropylene glycol methyl ether acetate that obtains obtains the pure product of dipropylene glycol methyl ether acetate through rectifying.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103435481A (en) * | 2013-09-13 | 2013-12-11 | 江苏华伦化工有限公司 | Production method of ethylene glycol diacetate (EGDA) |
| CN103483191A (en) * | 2013-09-13 | 2014-01-01 | 江苏华伦化工有限公司 | Method for producing DPMA |
| CN106966898A (en) * | 2017-04-21 | 2017-07-21 | 江苏天音化工有限公司 | A kind of method that presence of acidic ionic liquid catalyst synthesizes dipropylene glycol methyl ether acetate |
| CN107098810A (en) * | 2017-05-16 | 2017-08-29 | 天津大学 | A kind of process for separation and purification for preparing electronic grade propylene glycol methyl ether acetate |
| CN112010754A (en) * | 2020-08-19 | 2020-12-01 | 江门谦信化工发展有限公司 | Refining method for esterification synthesis of ethylene glycol methyl ether acetate |
| CN115215745A (en) * | 2022-09-07 | 2022-10-21 | 成都中金黎阳新材料科技有限公司 | Synthesis of diethylene glycol phenyl ether acetate and application of diethylene glycol phenyl ether acetate in high-temperature and low-temperature slurry |
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| CN101722027A (en) * | 2009-11-26 | 2010-06-09 | 沈阳工业大学 | Esterification catalyst for synthesizing ethylene/propylene glycol ether carboxylate, and preparation method thereof |
Non-Patent Citations (1)
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103435481A (en) * | 2013-09-13 | 2013-12-11 | 江苏华伦化工有限公司 | Production method of ethylene glycol diacetate (EGDA) |
| CN103483191A (en) * | 2013-09-13 | 2014-01-01 | 江苏华伦化工有限公司 | Method for producing DPMA |
| CN106966898A (en) * | 2017-04-21 | 2017-07-21 | 江苏天音化工有限公司 | A kind of method that presence of acidic ionic liquid catalyst synthesizes dipropylene glycol methyl ether acetate |
| CN107098810A (en) * | 2017-05-16 | 2017-08-29 | 天津大学 | A kind of process for separation and purification for preparing electronic grade propylene glycol methyl ether acetate |
| CN112010754A (en) * | 2020-08-19 | 2020-12-01 | 江门谦信化工发展有限公司 | Refining method for esterification synthesis of ethylene glycol methyl ether acetate |
| CN112010754B (en) * | 2020-08-19 | 2023-02-28 | 江门谦信化工发展有限公司 | Refining method for esterification synthesis of ethylene glycol methyl ether acetate |
| CN115215745A (en) * | 2022-09-07 | 2022-10-21 | 成都中金黎阳新材料科技有限公司 | Synthesis of diethylene glycol phenyl ether acetate and application of diethylene glycol phenyl ether acetate in high-temperature and low-temperature slurry |
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