CN101337885B - Method for preparing 1-Methoxy-2-propyl acetate by continuous esterification reaction - Google Patents
Method for preparing 1-Methoxy-2-propyl acetate by continuous esterification reaction Download PDFInfo
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- CN101337885B CN101337885B CN2008100216301A CN200810021630A CN101337885B CN 101337885 B CN101337885 B CN 101337885B CN 2008100216301 A CN2008100216301 A CN 2008100216301A CN 200810021630 A CN200810021630 A CN 200810021630A CN 101337885 B CN101337885 B CN 101337885B
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Abstract
The invention discloses a process for preparing propylene glycol methyl ether acetate by continuous esterification reaction, which adopts propylene glycol methyl ether and acetic acid as the raw materials. The process is characterized in that a solid acid catalyst is adopted to carry out two-section fixed bed continuous esterification reaction at the esterification temperature of 70 to 150 DEG C; water generated in the sterification reaction is removed by azeotropic distillation; and the result of the esterification reaction is rectified to remove and recover unreacted propylene glycol methyl ether and acetic acid to obtain propylene glycol methyl ether acetate. The method can achieve continuous production of propylene glycol methyl ether acetate, and has the advantages of simple operation manner, greatly improved production efficiency of propylene glycol methyl ether acetate, lowered production cost, reduced emission of solid contaminants and wastewater, and excellent large-scale industrial application value.
Description
Technical field
The present invention relates to a kind of preparation method of 1-Methoxy-2-propyl acetate, especially be particularly related to a kind of method of preparing 1-Methoxy-2-propyl acetate by continuous esterification reaction.
Background technology
1-Methoxy-2-propyl acetate (PMA) 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.Because 1-Methoxy-2-propyl acetate has characteristics such as solvent nature height, Heat stability is good, little, the high foaming of viscosity variation and corrodibility are little, is widely used in industry such as coating, washing composition, printing and dyeing, agricultural chemicals and pluronic polymer.
By propylene glycol monomethyl ether and acetic acid through esterification system 1-Methoxy-2-propyl 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).The problem that aforesaid method exists is, after finishing, reaction needs to handle by alkali neutralization and washing, removing employed catalyzer, and this method side reaction is many, corrodibility strong, complex technical process, production efficiency are low, produce 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, allegedly can 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 1-Methoxy-2-propyl acetate, this method can overcome the existing product of existing batch production technology to be needed to handle through neutralization and washing, and complex technical process, production efficiency low, produce shortcomings such as a large amount of solid waste and waste water, the present invention can realize the serialization production of 1-Methoxy-2-propyl acetate, and reduce the slag and effluent discharging in process of production, improve the production efficiency of 1-Methoxy-2-propyl acetate, reduce its production cost.
The technical solution adopted in the present invention is as follows:
A kind of method of preparing 1-Methoxy-2-propyl acetate by continuous esterification reaction, with propylene glycol monomethyl ether and acetic acid is raw material, it is characterized in that: adopt solid acid catalyst to carry out two-part 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 propylene glycol monomethyl ether and acetic acid, obtain 1-Methoxy-2-propyl acetate.
Described solid acid catalyst is a kind of cancellated composite enhanced polystyrolsulfon acid class strong-acid ion exchange resin that has.Synthetic this cancellated polymkeric substance, adopt the synthetic method of polystyrolsulfon acid class ion exchange resin commonly used, in the proportioning raw materials of polymerization single polymerization monomer, add mole number and account for the Vinylstyrene of polymerization single polymerization monomer 20-35%, and add the micron order graphite whisker that weight accounts for monomer total amount 1-3% (wt/wt).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 two-part fixed bed continuous esterification is meant at two all to be filled with two sections esterifications of carrying out continuously in the fixed-bed reactor of 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 propylene glycol monomethyl 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 propylene glycol monomethyl 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, esterification reaction temperature is 70-150 ℃, and preferable range is 90-120 ℃; The esterification air speed of two fixed-bed reactor is 1-10h
-1, preferable range is 3-6h
-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 propylene glycol monomethyl ether, acetic acid and with object esterification products 1-Methoxy-2-propyl acetate by discharging at the bottom of the distillation tower still, enter lightness-removing column rectifying, the lighting end that cat head steams is propylene glycol monomethyl ether and acetic acid, with its recovery.The propylene glycol monomethyl 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 1-Methoxy-2-propyl acetate.
Through the prepared product of aforesaid method is the 1-Methoxy-2-propyl acetate crude product.The lightness-removing column bottom product is delivered to the rectifying of product rectifying tower, can obtain the pure product of 1-Methoxy-2-propyl acetate.
Fig. 1 is the schema of the main part of two sections fixed bed preparing 1-Methoxy-2-propyl acetate by continuous esterification reaction technologies of employing 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.
Propylene glycol monomethyl 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
31-Methoxy-2-propyl acetate and unreacted propylene glycol monomethyl 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, propylene glycol monomethyl ether (121 ℃ of boiling points) and acetic acid (118.1 ℃ of boiling points) that the lightness-removing column top steams reclaim Recycling, the thick product of 1-Methoxy-2-propyl acetate at the bottom of the lightness-removing column still is delivered to product rectifying tower (not marking among Fig. 1) rectifying, obtain the pure product of 1-Methoxy-2-propyl acetate, 146 ℃ of boiling points.
In sum, the production method of 1-Methoxy-2-propyl acetate of the present invention by the novel process that serialization is produced, can realize the suitability for industrialized production of 1-Methoxy-2-propyl 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 and wash, the long service life of catalyzer, and the products production cost reduces.The method of preparing 1-Methoxy-2-propyl acetate by continuous esterification reaction of the present invention has good economic benefit and environmental benefit.
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
The process flow diagram of Fig. 1 preparing 1-Methoxy-2-propyl acetate by continuous esterification reaction
Technical process will be preheated to 110 ℃ raw material propylene glycol monomethyl ether and acetic acid 1: 1 in molar ratio, import first section fixed-bed reactor 1 that the 5L solid acid catalyst is housed continuously with the 15L/h flow as shown in Figure 1,110 ℃ of esterification reaction temperatures, and air speed is 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 5L solid acid catalyst 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 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, 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: 1-Methoxy-2-propyl acetate 57.6%, acetic acid 17.2%, propylene glycol monomethyl ether 25.2%.Distillation tower 3 tower still dischargings enter the lightness-removing column rectifying of other outfit, and the propylene glycol monomethyl ether that the lightness-removing column cat head steams and acetic acid reclaim Recycling, and lightness-removing column tower still material is delivered to product rectifying tower purifying, but output 1-Methoxy-2-propyl acetate product 7.6kg per hour.
Technical process as shown in Figure 1, be preheated to 90 ℃ raw material propylene glycol monomethyl ether and acetic acid 1.5: 1 in molar ratio, with the 10L/h flow continuously input be equipped with the 5L solid acid catalyst first section fixed-bed reactor 1,90 ℃ of esterification reaction temperatures, air speed is 2h
-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 5L solid acid catalyst is housed at the stripping section of distillation tower 3 continuously with the 10L/h flow, 90 ℃ of esterification reaction temperatures, and air speed is 2h
-1The mass flow that is input to second section fixed-bed reactor 2 is 1 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: 1-Methoxy-2-propyl acetate 44.2%, acetic acid 12.7%, propylene glycol monomethyl ether 43.1%.Distillation tower 3 tower still dischargings enter the lightness-removing column fractionation of other outfit, and the propylene glycol monomethyl ether that the lightness-removing column cat head steams and acetic acid reclaim Recycling, and lightness-removing column tower still material is got to the rectifying of product rectifying tower, but output 1-Methoxy-2-propyl acetate product 3.9kg per hour.
Claims (9)
1. the method for a preparing 1-Methoxy-2-propyl acetate by continuous esterification reaction, with propylene glycol monomethyl ether and acetic acid is raw material, it is characterized in that: employing has cancellated composite enhanced polystyrolsulfon acid class strongly acidic ion-exchange resin catalyst and carries out two-part 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 propylene glycol monomethyl ether and acetic acid, obtain 1-Methoxy-2-propyl acetate.
2. the method for preparing 1-Methoxy-2-propyl acetate by continuous esterification reaction according to claim 1, it is characterized in that: in the proportioning raw materials of synthetic described ion exchange resin, add mole number and account for the Vinylstyrene of polymerization single polymerization monomer 20-35%, and add the micron order graphite whisker that weight accounts for monomer total amount 1-3%.
3. the method for preparing 1-Methoxy-2-propyl acetate by continuous esterification reaction according to claim 1, it is characterized in that: described two-part fixed bed continuous esterification, be meant at two all to be filled with two sections esterifications of carrying out continuously in the fixed-bed reactor of solid acid catalyst that first section esterification reaction product carries out second section esterification after removing and reacting the water that generates.
4. the method for preparing 1-Methoxy-2-propyl acetate by continuous esterification reaction according to claim 3, it is characterized in that: described two-part fixed bed continuous esterification comprises, after raw material propylene glycol monomethyl 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.
5. according to the method for claim 1 or 3 described preparing 1-Methoxy-2-propyl acetate by continuous esterification reaction, it is characterized in that: entering the raw material propylene glycol monomethyl 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.
6. according to the method for claim 1 or 3 described preparing 1-Methoxy-2-propyl acetate by continuous esterification reaction, it is characterized in that: esterification reaction temperature is 90-120 ℃.
7. according to the method for claim 1 or 3 described preparing 1-Methoxy-2-propyl acetate by continuous esterification reaction, it is characterized in that: the esterification air speed of described fixed-bed reactor is 1-10h
-1
8. according to the method for claim 1 or 3 described preparing 1-Methoxy-2-propyl acetate by continuous esterification reaction, it is characterized in that: the band aqua that described component distillation adopts is benzene or hexanaphthene.
9. according to the method for claim 1 or 3 described preparing 1-Methoxy-2-propyl acetate by continuous esterification reaction, it is characterized in that: the 1-Methoxy-2-propyl acetate that obtains obtains the pure product of 1-Methoxy-2-propyl acetate through rectifying.
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| CN108299203A (en) * | 2018-01-29 | 2018-07-20 | 淄博高新技术产业开发区精细化工和高分子材料研究院 | A method of PGMEA being recycled from PGMEA/ aqueous solutions using intermittent azeotropic rectifying |
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