CN107032986B - A kind of method of presence of acidic ionic liquid catalyst synthesis 2- methoxy-1-propanol ether acetate - Google Patents
A kind of method of presence of acidic ionic liquid catalyst synthesis 2- methoxy-1-propanol ether acetate Download PDFInfo
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Abstract
The invention discloses a kind of methods of presence of acidic ionic liquid catalyst synthesis 2- methoxy-1-propanol ether acetate, it is characterized by: using 2- methoxy-1-propanol and acetic acid as raw material, under acidic ionic liquid catalysts 1- butyl -3- methylimidazolium hydrogen sulphate salt and hexamethylene dehydrating agent collective effect, 2- methoxy-1-propanol ether acetate is synthesized using esterification evaporation, wherein, catalyst amount is the 0.2-8% of 2- methoxy-1-propanol and acetic acid quality；The molar ratio of 2- methoxy-1-propanol and acetic acid is 1: 1-3；75-150 DEG C of esterification reaction temperature, the water generated in esterification and hexamethylene azeotropic distillation remove；2- methoxy-1-propanol ether acetate will be obtained after esterification reaction product rectifying, the kettle liquid after rectifying is recycled containing catalyst and part 2- methoxy-1-propanol ether acetate.The method of the present invention catalyst activity is high, and stability is good, and low to equipment corrosion, catalyst can be recycled.
Description
Technical field
The present invention relates to a kind of synthetic methods of 2- methoxy-1-propanol ether acetate, and in particular to a kind of acidic ionic liquid
The method of body catalytic esterification synthesis 2- methoxy-1-propanol ether acetate.
Background technique
During using propylene oxide and methanol to produce propylene glycol monomethyl ether for raw material, not due to propylene oxide molecule
Symmetry, propylene oxide open loop and the addition of methanol obtain two kinds of isomers, i.e. 1- methoxy-2-propanol and 2- methoxy
Base -1- propyl alcohol, 1- methoxy-2-propanol are purpose products propylene glycol methyl ether (PM), and 2- methoxy-1-propanol is by-product, referred to as
2- methoxy-1-propanol ether acetate is made (also known as in 2- methoxy-1-propanol and acetic acid reaction by isomery propylene glycol monomethyl ether (IPM)
Isomery propylene glycol methyl ether acetate, I PMA) have become the important utilization ways of by-product I PM.
2- methoxy-1-propanol ether acetate (IPMA) is a kind of important industrial solvent, the solvent molecule unique structure, together
Existing nonpolar part in one molecule, and polarized group, therefore it has preferable dissolution energy to polarity and apolar substance
Power, solubility property are much higher than common solvent and gylcol ether and propylene glycol ether solvent.Since I PMA has dissolubility
Can be high, thermal stability is good, viscosity change is small and corrosivity is small the features such as, be widely used in coating, detergent, printing and dyeing, pesticide and
The industry such as pluronic polymer.
It through esterification isomery propylene glycol methyl ether acetate (IPMA) is logical by isomery propylene glycol monomethyl ether (IPM) and acetic acid
Technology path, the method industrially generallyd use at present be esterification dehydration technique, as CN1515537A,
CN101475469A etc., catalyst used in reaction process are usually inorganic acid or organic acid, and inorganic acid is main are as follows: phosphoric acid,
Hydrochloric acid and the concentrated sulfuric acid；Organic acid is main are as follows: oxalic acid, citric acid, methanesulfonic acid and p-methyl benzenesulfonic acid take homogeneous reaction.Above-mentioned side
Method the problem is that, need after reaction by alkali neutralization remove used in catalyst, and this method side reaction it is more, corrode
Property it is strong, complex technical process, production efficiency are low, generate a large amount of solid waste and contaminated wastewater environment.
Also there are report (Wang Xi, Liaoning teacher that propylene-glycol ether acetate synthesis is used for using heteropllyacids solid acid catalyst
Special journal: natural science edition, the 1st phase of volume 2 in 2000), but from the complexity on heteropoly acid the Nomenclature Composition and Structure of Complexes itself and make
Consider that industrially practical application difficulty is bigger with factors such as service life.
The method that applicant had previously used solid acid catalyst continuous esterification to prepare 2- methoxy-1-propanol ether acetate
(CN101985418B, on January 2nd, 2013) can overcome product present in batch production technique to need neutralized processing, generate
The disadvantages of a large amount of solid waste and waste water, realize the continuous production of 2- methoxy-1-propanol ether acetate, but due to the ester
Change and react existing reversible reaction, is limited by thermodynamics of reactions balance, reaction conversion ratio is lower.
Ionic liquid many advantages, such as low melting point, good solubilising and is considered as one since it is with non-volatile
Class novel green solvent and reaction medium, ionic liquid also show that good application prospect in terms of being catalyzed organic reaction.
Summary of the invention
The purpose of the present invention is being directed to the deficiencies in the prior art, a kind of presence of acidic ionic liquid catalyst synthesis 2- is provided
The method of methoxy-1-propanol ether acetate.
The technical solution adopted in the present invention is as follows:
A kind of method of presence of acidic ionic liquid catalyst synthesis 2- methoxy-1-propanol ether acetate, with 2- methoxy-1-propanol
It is raw material with acetic acid, it is common in acidic ionic liquid catalysts 1- butyl -3- methylimidazolium hydrogen sulphate salt and dehydrating agent hexamethylene
Under effect, esterification occurs and synthesizes 2- methoxy-1-propanol ether acetate, the water and hexamethylene azeotropic generated in esterification steams
Evaporate removing；Esterification reaction product rectifying is obtained into 2- methoxy-1-propanol ether acetate product.
In above-mentioned synthetic method, the suitable use of acidic ionic liquid catalysts 1- butyl -3- methylimidazolium hydrogen sulphate salt
Amount is the 0.2-8% of the quality of 2- methoxy-1-propanol and acetic acid, and catalyst amount is more, and reaction speed increase is unobvious, and urges
The excessively few then reaction speed of agent dosage is slow, and the required reaction time is long.
In above-mentioned synthetic method, 2- methoxy-1-propanol and the acetic acid suitable molar ratio that feeds intake are 1: 1-3, acetic acid mistake
Measure more, advantageous to the progress and shortening reaction time that promote positive reaction, but the amount of acetic acid can excessively make the yield of unit equipment
It reduces, the energy consumption of recovery of acetic acid increases.
In above-mentioned synthetic method, suitable esterification reaction temperature is 75-150 DEG C, and reaction temperature is too low, then reaction speed
Slowly；Reaction temperature is excessively high, is easy to produce side reaction, and deepens reactant color.
In above-mentioned synthetic method, suitable reaction time of esterification is 2-4h, and the reaction time is too long, and side reaction increases, instead
Damp intensification should be looked for；Reaction time is too short, and esterification conversion ratio is low.
The water generated in esterification in above-mentioned synthetic method and hexamethylene azeotropic distillation remove, dehydrating agent hexamethylene
Suitable dosage is the 45-55% of 2- methoxy-1-propanol quality.Dehydrating agent hexamethylene dosage is excessive, and reaction temperature can be made inclined
Low, reaction speed is slow；Dehydrating agent hexamethylene dosage is very few, and the water that cannot be generated with esterification forms azeotropic composition, makes to be dehydrated
Effect is bad, influences reaction conversion ratio.
In the method, esterification reaction product carries out two step rectifying, and a small amount of unreacted 2- methoxyl group-is recycled in first rectifying
1- propyl alcohol and acetic acid, then rectifying obtain 2- methoxy-1-propanol ether acetate product, kettle liquid 1- containing the catalyst butyl-after rectifying
3- methylimidazolium hydrogen sulphate salt and part 2- methoxy-1-propanol ether acetate are recycled.
The method of the present invention compared with prior art, has catalyst activity high, and stability is good, and height is received in reaction, to equipment corruption
The advantages that corrosion is low, and catalyst can be recycled.The method can significantly improve the production of 2- methoxy-1-propanol ether acetate
Efficiency reduces its production cost, and can be reduced solid pollutant and discharge of wastewater, has splendid large-scale industrial application valence
Value.
Specific embodiment
The present invention will be described in detail combined with specific embodiments below.The scope of the present invention is not with specific embodiment
It is limited, but is limited by the scope of the claims.
Raw material acetic acid in following embodiment and comparative example is technical grade, raw by Celanese Nanjing Chemical Co., Ltd.
It produces；2- methoxy-1-propanol is technical grade, is produced by Dena (Nanjing) Chemical Co., Ltd.；Hexamethylene is that chemistry is pure, by me
The production of fourth reagent (Shanghai) Co., Ltd.；Acidic ionic liquid catalysts 1- butyl -3- methylimidazolium hydrogen sulphate salt, 1- butyl -
3- methylimidazole dibutylphosphoric acid ester salt, 1- hexyl -3- methylimidazolium nitrate are produced by upper marine origin victory Chemical Co., Ltd., pure
Degree >=99%；Water content≤1000ppm；Halogen content≤800ppm.
Reaction yield refers to that the quality of the 2- methoxy-1-propanol ether acetate generated in reactant of esterification accounts for the 2- methoxy that feeds intake
Base -1- propyl alcohol generates the ratio of the Theoretical Mass of 2- methoxy-1-propanol ether acetate completely.Using reaction solution weighing and gas phase color
Spectrum analysis measures 2- methoxy-1-propanol ether acetate content in reaction solution and calculates reaction yield.
Embodiment 1
In the 1000ml glass four-hole boiling flask that thermometer, rectifying column, condenser pipe, water segregator are housed, 2- methoxyl group-is added
The molar ratio of 1- propyl alcohol 270g, acetic acid 198g, 2- methoxy-1-propanol and acetic acid is 1: 1.1, acidic ionic liquid catalysts 1-
Butyl -3- methylimidazolium hydrogen sulphate salt dosage is 4.7g, and dehydrating agent hexamethylene is 135g, heats up and reactant is kept to be in always
Fluidized state (75-150 DEG C), reflux water-dividing, 4h reaction terminate, 2- in reactant weighing and gas chromatographic analysis measurement reaction solution
Methoxy-1-propanol ether acetate content, calculating reaction yield is 97.7%.
Esterification reaction product is subjected to two step rectifying, a small amount of unreacted 2- methoxy-1-propanol and vinegar are recycled in first rectifying
Acid (contains a small amount of hexamethylene dehydrating agent, do not influence to be recycled), then rectifying obtains finished product 2- methoxy-1-propanol ether acetate, produces
Product purity 99.91%.The kettle liquid butyl of 1- containing catalyst -3- methylimidazolium hydrogen sulphate salt and part 2- methoxyl group -1- after rectifying
Propanol ether acetate needs to be recycled.
Embodiment 2
By the catalyst that is recycled after use in embodiment 1 investment equipped with thermometer, rectifying column, condenser pipe, water segregator
In 1000ml glass four-hole boiling flask, 2- methoxy-1-propanol 270g is added, acetic acid 198g, 2- methoxy-1-propanol and acetic acid
Molar ratio is 1: 1.1, and dehydrating agent hexamethylene is 135g, heats up and reactant is kept to be in fluidized state (75-150 DEG C) always,
Reflux water-dividing, 4h reaction terminate, 2- methoxy-1-propanol ether acetate in reactant weighing and gas chromatographic analysis measurement reaction solution
Content, calculating reaction yield is 97.6%.
Esterification reaction product is subjected to two step rectifying, a small amount of unreacted 2- methoxy-1-propanol and vinegar are recycled in first rectifying
Acid (contains a small amount of hexamethylene dehydrating agent, do not influence to be recycled), then rectifying obtains finished product 2- methoxy-1-propanol ether acetate, produces
Product purity 99.92%.The kettle liquid butyl of 1- containing catalyst -3- methylimidazolium hydrogen sulphate salt and part 2- methoxyl group -1- after rectifying
Propanol ether acetate needs recycled.
Embodiment 3
After the catalyst recycled after use in embodiment 2 is reused 5 times investment equipped with thermometer, rectifying column, condenser pipe,
In the 1000ml glass four-hole boiling flask of water segregator, 2- methoxy-1-propanol 270g, acetic acid 198g, 2- methoxy-1-propanol is added
Molar ratio with acetic acid is 1: 1.1, and dehydrating agent hexamethylene is 135g, heats up and reactant is kept to be in fluidized state (75- always
150 DEG C), reflux water-dividing, 4h reaction terminates, 2- methoxyl group -1- third in reactant weighing and gas chromatographic analysis measurement reaction solution
Alcohol acetate content, calculating reaction yield is 97.3%.
Esterification reaction product is subjected to two step rectifying, a small amount of unreacted 2- methoxy-1-propanol and vinegar are recycled in first rectifying
Acid (contains a small amount of hexamethylene dehydrating agent, do not influence to be recycled), then rectifying obtains finished product 2- methoxy-1-propanol ether acetate, produces
Product purity 99.91%.The kettle liquid butyl of 1- containing catalyst -3- methylimidazolium hydrogen sulphate salt and part 2- methoxyl group -1- after rectifying
Propanol ether acetate needs recycled.
Embodiment 4
In the 1000ml glass four-hole boiling flask that thermometer, rectifying column, condenser pipe, water segregator are housed, 2- methoxyl group-is added
The molar ratio of 1- propyl alcohol 270g, acetic acid 360g, 2- methoxy-1-propanol and acetic acid is 1: 2, acidic ionic liquid catalysts 1- fourth
Base -3- methylimidazolium hydrogen sulphate salt dosage is 6.3g, and dehydrating agent hexamethylene is 122g, heats up and reactant is kept to be in boiling always
It rises state (75-150 DEG C), reflux water-dividing, 4h reaction terminates, 2- first in reactant weighing and gas chromatographic analysis measurement reaction solution
Oxy-1-propanol acetate ester content, calculating reaction yield is 97.9%.
Esterification reaction product is subjected to two step rectifying, a small amount of unreacted 2- methoxy-1-propanol and vinegar are recycled in first rectifying
Acid (contains a small amount of hexamethylene dehydrating agent, do not influence to be recycled), then rectifying obtains finished product 2- methoxy-1-propanol ether acetate, produces
Product purity 99.91%.The kettle liquid butyl of 1- containing catalyst -3- methylimidazolium hydrogen sulphate salt and part 2- methoxyl group -1- after rectifying
Propanol ether acetate needs to be recycled.
Embodiment 5
In the 1000ml glass four-hole boiling flask that thermometer, rectifying column, condenser pipe, water segregator are housed, 2- methoxyl group-is added
The molar ratio of 1- propyl alcohol 270g, acetic acid 198g, 2- methoxy-1-propanol and acetic acid is 1: 1.1, acidic ionic liquid catalysts 1-
Butyl -3- methylimidazolium hydrogen sulphate salt dosage is 18.8g, and dehydrating agent hexamethylene is 135g, heats up and reactant is kept to locate always
In fluidized state (75-150 DEG C), reflux water-dividing, 4h reaction terminates, in reactant weighing and gas chromatographic analysis measurement reaction solution
2- methoxy-1-propanol ether acetate content, calculating reaction yield is 97.8%.
Esterification reaction product is subjected to two step rectifying, a small amount of unreacted 2- methoxy-1-propanol and vinegar are recycled in first rectifying
Acid (contains a small amount of hexamethylene dehydrating agent, do not influence to be recycled), then rectifying obtains finished product 2- methoxy-1-propanol ether acetate, produces
Product purity 99.92%.The kettle liquid butyl of 1- containing catalyst -3- methylimidazolium hydrogen sulphate salt and part 2- methoxyl group -1- after rectifying
Propanol ether acetate needs to be recycled.
Embodiment 6
In the 1000ml glass four-hole boiling flask that thermometer, rectifying column, condenser pipe, water segregator are housed, 2- methoxyl group-is added
The molar ratio of 1- propyl alcohol 270g, acetic acid 198g, 2- methoxy-1-propanol and acetic acid is 1: 1.1, acidic ionic liquid catalysts 1-
Butyl -3- methylimidazolium hydrogen sulphate salt dosage is 4.7g, and dehydrating agent hexamethylene is 135g, heats up and reactant is kept to be in always
Fluidized state (75-150 DEG C), reflux water-dividing, 3h reaction terminate, 2- in reactant weighing and gas chromatographic analysis measurement reaction solution
Methoxy-1-propanol ether acetate content, calculating reaction yield is 96.2%.
Esterification reaction product is subjected to two step rectifying, a small amount of unreacted 2- methoxy-1-propanol and vinegar are recycled in first rectifying
Acid (contains a small amount of hexamethylene dehydrating agent, do not influence to be recycled), then rectifying obtains finished product 2- methoxy-1-propanol ether acetate, produces
Product purity 99.91%.The kettle liquid butyl of 1- containing catalyst -3- methylimidazolium hydrogen sulphate salt and part 2- methoxyl group -1- after rectifying
Propanol ether acetate needs to be recycled.
Embodiment 7
In the 1000ml glass four-hole boiling flask that thermometer, rectifying column, condenser pipe, water segregator are housed, 2- methoxyl group-is added
The molar ratio of 1- propyl alcohol 270g, acetic acid 198g, 2- methoxy-1-propanol and acetic acid is 1: 1.1, acidic ionic liquid catalysts 1-
Butyl -3- methylimidazolium hydrogen sulphate salt dosage is 4.7g, and dehydrating agent hexamethylene is 150g, heats up and reactant is kept to be in always
Fluidized state (75-145 DEG C), reflux water-dividing, 4h reaction terminate, 2- in reactant weighing and gas chromatographic analysis measurement reaction solution
Methoxy-1-propanol ether acetate content, calculating reaction yield is 97.1%.
Esterification reaction product is subjected to two step rectifying, a small amount of unreacted 2- methoxy-1-propanol and vinegar are recycled in first rectifying
Acid (contains a small amount of hexamethylene dehydrating agent, do not influence to be recycled), then rectifying obtains finished product 2- methoxy-1-propanol ether acetate, produces
Product purity 99.91%.The kettle liquid butyl of 1- containing catalyst -3- methylimidazolium hydrogen sulphate salt and part 2- methoxyl group -1- after rectifying
Propanol ether acetate needs to be recycled.
Comparative example 1
In the 1000ml glass four-hole boiling flask that thermometer, rectifying column, condenser pipe, water segregator are housed, 2- methoxyl group-is added
The molar ratio of 1- propyl alcohol 270g, acetic acid 198g, 2- methoxy-1-propanol and acetic acid is 1: 1.1, acidic ionic liquid catalysts 1-
Butyl -3- methylimidazole dibutylphosphoric acid ester salt dosage is 4.7g, and dehydrating agent hexamethylene is 150g, heats up and keeps reactant always
In fluidized state (75-145 DEG C), reflux water-dividing, 4h reaction terminates, and reactant weighing and gas chromatographic analysis measure reaction solution
Middle 2- methoxy-1-propanol ether acetate content, calculating reaction yield is 86.6%.
Esterification reaction product is subjected to two step rectifying, a small amount of unreacted 2- methoxy-1-propanol and vinegar are recycled in first rectifying
Acid (contains a small amount of hexamethylene dehydrating agent, do not influence to be recycled), then rectifying obtains finished product 2- methoxy-1-propanol ether acetate, produces
Product purity 97.62%.
Comparative example 2
In the 1000ml glass four-hole boiling flask that thermometer, rectifying column, condenser pipe, water segregator are housed, 2- methoxyl group-is added
The molar ratio of 1- propyl alcohol 270g, acetic acid 198g, 2- methoxy-1-propanol and acetic acid is 1: 1.1, acidic ionic liquid catalysts 1-
Hexyl -3- methylimidazolium nitrate dosage is 4.7g, and dehydrating agent hexamethylene is 150g, heats up and reactant is kept to be in boiling always
It rises state (75-145 DEG C), reflux water-dividing, 4h reaction terminates, 2- first in reactant weighing and gas chromatographic analysis measurement reaction solution
Oxy-1-propanol acetate ester content, calculating reaction yield is 87.3%.
Esterification reaction product is subjected to two step rectifying, a small amount of unreacted 2- methoxy-1-propanol and vinegar are recycled in first rectifying
Acid (contains a small amount of hexamethylene dehydrating agent, do not influence to be recycled), then rectifying obtains finished product 2- methoxy-1-propanol ether acetate, produces
Product purity 96.64%.
Claims (8)
1. a kind of method of presence of acidic ionic liquid catalyst synthesis 2- methoxy-1-propanol ether acetate, it is characterised in that: with 2- methoxy
Base -1- propyl alcohol and acetic acid are raw material, in acidic ionic liquid catalysts 1- butyl -3- methylimidazolium hydrogen sulphate salt and dehydrating agent ring
Under hexane collective effect, esterification occurs and synthesizes 2- methoxy-1-propanol ether acetate；The water and hexamethylene generated in esterification
Alkane azeotropic distillation removing；Esterification reaction product rectifying is obtained into 2- methoxy-1-propanol ether acetate product.
2. the method for presence of acidic ionic liquid catalyst synthesis 2- methoxy-1-propanol ether acetate according to claim 1, special
Sign is: the acidic ionic liquid catalysts 1- butyl -3- methylimidazolium hydrogen sulphate salt dosage is 2- methoxy-1-propanol
With the 0.2-8% of acetic acid quality.
3. the method for presence of acidic ionic liquid catalyst synthesis 2- methoxy-1-propanol ether acetate according to claim 1, special
Sign is: the molar ratio of the 2- methoxy-1-propanol and acetic acid is 1: 1-3.
4. the method for presence of acidic ionic liquid catalyst synthesis 2- methoxy-1-propanol ether acetate according to claim 1, special
Sign is: the dosage of the dehydrating agent hexamethylene is the 45-55% of 2- methoxy-1-propanol quality.
5. the method for presence of acidic ionic liquid catalyst synthesis 2- methoxy-1-propanol ether acetate according to claim 1, special
Sign is: esterification reaction temperature is 75-150 DEG C.
6. the method for presence of acidic ionic liquid catalyst synthesis 2- methoxy-1-propanol ether acetate according to claim 1, special
Sign is: reaction time of esterification 2-4h.
7. the method for presence of acidic ionic liquid catalyst synthesis 2- methoxy-1-propanol ether acetate according to claim 1, special
Sign is: esterification reaction product being carried out two step rectifying, a small amount of unreacted 2- methoxy-1-propanol and vinegar are recycled in first rectifying
Acid, then rectifying obtain 2- methoxy-1-propanol ether acetate product.
8. the method for presence of acidic ionic liquid catalyst synthesis 2- methoxy-1-propanol ether acetate according to claim 1, special
Sign is: the kettle liquid butyl of 1- containing catalyst -3- methylimidazolium hydrogen sulphate salt and part 2- methoxy-1-propanol acetic acid after rectifying
Ester is recycled.
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