CN107032986A - A kind of method that presence of acidic ionic liquid catalyst synthesizes the propanol ether acetate of 2 methoxyl group 1 - Google Patents
A kind of method that presence of acidic ionic liquid catalyst synthesizes the propanol ether acetate of 2 methoxyl group 1 Download PDFInfo
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- CN107032986A CN107032986A CN201710264882.6A CN201710264882A CN107032986A CN 107032986 A CN107032986 A CN 107032986A CN 201710264882 A CN201710264882 A CN 201710264882A CN 107032986 A CN107032986 A CN 107032986A
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- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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Abstract
The invention discloses a kind of method that presence of acidic ionic liquid catalyst synthesizes the propanol ether acetate of 2 methoxyl group 1, it is characterised in that：Using the propyl alcohol of 2 methoxyl group 1 and acetic acid as raw material, under the methylimidazolium hydrogen sulphate salt of 1 butyl of acidic ionic liquid catalysts 3 and hexamethylene dehydrating agent collective effect, using the esterification evaporation synthesis propanol ether acetate of 2 methoxyl group 1, wherein, catalyst amount is the 0.2 8% of the propyl alcohol of 2 methoxyl group 1 and acetic acid quality；The mol ratio of the propyl alcohol of 2 methoxyl group 1 and acetic acid is 1: 13；75 150 DEG C of esterification reaction temperature, the water generated in esterification is removed with hexamethylene azeotropic distillation；The propanol ether acetate of 2 methoxyl group 1 will be obtained after esterification reaction product rectifying, the kettle liquid after rectifying is recycled containing catalyst and the propanol ether acetate of 2 methoxyl group of part 1.The inventive method 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 method of 2- methoxy-1-propanol ether acetates, and in particular to a kind of acidic ionic liquid
The method that body catalytic esterification synthesizes 2- methoxy-1-propanol ether acetates.
Background technology
During expoxy propane and methanol is used for raw material production propylene glycol monomethyl ether, due to expoxy propane molecule not
Symmetry, expoxy propane open loop and the addition of methanol obtain two kinds of isomers, i.e. 1- methoxy-2-propanols and 2- methoxies
Base -1- propyl alcohol, 1- methoxy-2-propanols are purpose products propylene glycol methyl ether (PM), and 2- methoxy-1-propanols are by-product, are referred to as
Isomery propylene glycol monomethyl ether (IPM), 2- methoxy-1-propanol ether acetates are made (also known as by 2- methoxy-1-propanols and acetic acid reaction
Isomery propylene glycol methyl ether acetate, I PMA) turn into accessory substance I PM important utilization ways.
2- methoxy-1-propanol ether acetates (IPMA) are the important industrial solvents of a class, the solvent molecule unique structure, together
Existing nonpolar part in one molecule, and polarized group, therefore it has preferably dissolving energy to polarity and apolar substance
Power, its solubility property is much higher than common solvent and gylcol ether and propane diols ether solvent.Because I PMA have dissolubility
Can height, good heat endurance, small viscosity B coefficent and the features such as small corrosivity, be widely used in coating, detergent, printing and dyeing, agricultural chemicals and
The industry such as pluronic polymer.
Through esterification isomery propylene glycol methyl ether acetate (IPMA) it is logical by isomery propylene glycol monomethyl ether (IPM) and acetic acid
Technology path, the method generally used industrial at present is to be esterified dehydration technique, such as CN1515537A,
CN101475469A etc., the catalyst used in course of reaction is usually inorganic acid or organic acid, and inorganic acid is mainly：Phosphoric acid,
Hydrochloric acid and the concentrated sulfuric acid；Organic acid is mainly：Oxalic acid, citric acid, methanesulfonic acid and p-methyl benzenesulfonic acid, take homogeneous reaction.Above-mentioned side
The problem of method is present is that reaction is needed after terminating by catalyst in alkali and used in removing, and this method side reaction is more, corrosion
Property strong, complex technical process, production efficiency are low, produce substantial amounts of solid waste and contaminated wastewater environment.
Also have is used for report (Wang Xi, Liaoning teacher that propylene-glycol ether acetate is synthesized 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 than larger with factors such as life-spans.
The method that applicant had previously prepared 2- methoxy-1-propanol ether acetates using solid acid catalyst continuous esterification
(CN101985418B, on January 2nd, 2013) can overcome the product present in batch production technique to need neutralized processing, produce
The shortcomings of substantial amounts of solid waste and waste water, the continuous production of 2- methoxy-1-propanol ether acetates is realized, but due to the ester
Change the reversible reaction that reaction is present, limited by thermodynamics of reactions balance, reaction conversion ratio is relatively low.
Ionic liquid has non-volatile a, low melting point due to it, is considered as one many advantages, such as good solubilising
Class new green solvent and reaction medium, ionic liquid also show that good application prospect in terms of organic reaction is catalyzed.
The content of the invention
The purpose of the present invention is that there is provided a kind of presence of acidic ionic liquid catalyst synthesis 2- for the deficiencies in the prior art
The method of methoxy-1-propanol ether acetate.
The technical solution adopted in the present invention is as follows：
A kind of method that presence of acidic ionic liquid catalyst synthesizes 2- methoxy-1-propanol ether acetates, with 2- methoxy-1-propanols
It is raw material with acetic acid, it is common in acidic ionic liquid catalysts 1- butyl -3- methylimidazolium hydrogen sulphates salt and dehydrating agent hexamethylene
Under effect, the water for occurring to generate in esterification synthesis 2- methoxy-1-propanol ether acetates, esterification steams with hexamethylene azeotropic
Evaporate removing；Esterification reaction product rectifying is obtained into 2- methoxy-1-propanol ether acetate products.
In above-mentioned synthetic method, the use of acidic ionic liquid catalysts 1- butyl -3- methylimidazolium hydrogen sulphates salt suitably
The 0.2-8% of the quality for 2- methoxy-1-propanols and acetic acid is measured, catalyst amount is more, and reaction speed increase is not obvious, and urges
Agent consumption crosses reaction speed at least, and slowly, the required reaction time is long.
In above-mentioned synthetic method, 2- methoxy-1-propanols and the acetic acid suitable mol ratio that feeds intake are 1: 1-3, acetic acid mistake
Amount is more, and the progress and shortening reaction time to promotion positive reaction are favourable, but the amount of acetic acid can excessively make the yield of unit equipment
Reduce, the energy consumption increase of recovery of acetic acid.
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 too high, easily produces side reaction, and deepen reactant color and luster.
In above-mentioned synthetic method, suitable reaction time of esterification is 2-4h, and the reaction time is long, and side reaction increases, instead
Damp intensification should be looked for；Reaction time is too short, and esterification conversion ratio is low.
In above-mentioned synthetic method, the water generated in esterification is removed with hexamethylene azeotropic distillation, dehydrating agent hexamethylene
Suitable consumption is the 45-55% of 2- methoxy-1-propanol quality.Dehydrating agent hexamethylene consumption is excessive, reaction temperature can be made inclined
Low, reaction speed is slow；Dehydrating agent hexamethylene consumption is very few, it is impossible to the water formation azeotropic composition generated with esterification, makes dehydration
Effect is bad, influences reaction conversion ratio.
In described method, esterification reaction product two step rectifying of progress, the first a small amount of unreacted 2- methoxyl groups of rectifying recovery-
1- propyl alcohol and acetic acid, then rectifying obtain 2- methoxy-1-propanol ether acetate products, and kettle liquid 1- containing the catalyst butyl after rectifying-
3- methylimidazolium hydrogen sulphates salt and part 2- methoxy-1-propanol ether acetates are recycled.
The inventive method is compared with prior art, high with catalyst activity, and stability is good, and reaction receives high, rotten to equipment
Corrosion is low, the advantages of catalyst can be recycled.Described method can significantly improve the production of 2- methoxy-1-propanol ether acetates
Efficiency, reduces its production cost, and can reduce solid pollutant and discharge of wastewater, with splendid large-scale industrial application valency
Value.
Embodiment
With reference to specific embodiment, the present invention will be described in detail.The scope of the present invention is not with embodiment
It is limited, but is limited by the scope of claim.
Raw material acetic acid in following examples and comparative example is technical grade, is given birth to by Celanese Nanjing Chemical Co., Ltd.
Production；2- methoxy-1-propanols are technical grade, are produced by Dena (Nanjing) Chemical Co., Ltd.；Hexamethylene is pure for chemistry, by me
Fourth reagent (Shanghai) Co., Ltd. produces；Acidic ionic liquid catalysts 1- butyl -3- methylimidazolium hydrogen sulphates salt, 1- butyl -
3- methylimidazole dibutylphosphoric acid esters salt, 1- hexyl -3- methylimidazolium nitrates, by upper marine origin, prompt Chemical Co., Ltd. produces, pure
Degree >=99%；Water content≤1000ppm；Halogen content≤800ppm.
Reaction yield refers to that the quality of the 2- methoxy-1-propanol ether acetates generated in reactant of esterification accounts for the 2- methoxies that feed intake
Base -1- propyl alcohol generates the ratio of the Theoretical Mass of 2- methoxy-1-propanol ether acetates completely.Weighed and gas phase color using reaction solution
Analysis of spectrum determines 2- methoxy-1-propanol ether acetate cubage reaction yields in reaction solution.
Embodiment 1
In equipped with thermometer, rectifying column, condenser pipe, the 1000ml glass four-hole boiling flasks of water knockout drum, addition 2- methoxyl groups-
The mol 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 consumption is 4.7g, and dehydrating agent hexamethylene is 135g, heats up and keeps reactant to be in all the time
Fluidized state (75-150 DEG C), reflux water-dividing, 4h reactions terminate, and reactant is weighed and determines 2- in reaction solution with gas chromatographic analysis
Methoxy-1-propanol ether acetate content, it is 97.7% to calculate reaction yield.
Esterification reaction product is subjected to two step rectifying, a small amount of unreacted 2- methoxy-1-propanols and vinegar are reclaimed in first rectifying
Acid (contains a small amount of hexamethylene dehydrating agent, do not influence to recycle), then rectifying obtains finished product 2- methoxy-1-propanol ether acetates, produces
Product purity 99.91%.Kettle liquid 1- containing catalyst butyl -3- methylimidazolium hydrogen sulphates salt and part 2- methoxyl groups -1- after rectifying
Propanol ether acetate needs to be recycled.
Embodiment 2
The catalyst that is reclaimed after use in embodiment 1 is put into equipped with thermometer, rectifying column, condenser pipe, water knockout drum
In 1000ml glass four-hole boiling flasks, 2- methoxy-1-propanol 270g are added, acetic acid 198g, 2- methoxy-1-propanol and acetic acid
Mol ratio is 1: 1.1, and dehydrating agent hexamethylene is 135g, heats up and keeps reactant to be in fluidized state (75-150 DEG C) all the time,
Reflux water-dividing, 4h reactions terminate, and reactant is weighed and determines 2- methoxy-1-propanol ether acetates in reaction solution with gas chromatographic analysis
Content, it is 97.6% to calculate reaction yield.
Esterification reaction product is subjected to two step rectifying, a small amount of unreacted 2- methoxy-1-propanols and vinegar are reclaimed in first rectifying
Acid (contains a small amount of hexamethylene dehydrating agent, do not influence to recycle), then rectifying obtains finished product 2- methoxy-1-propanol ether acetates, produces
Product purity 99.92%.Kettle liquid 1- containing catalyst butyl -3- methylimidazolium hydrogen sulphates salt and part 2- methoxyl groups -1- after rectifying
Propanol ether acetate needs recycled.
Embodiment 3
By the catalyst reclaimed after use in embodiment 2 reuse after 5 times input equipped with thermometer, rectifying column, condenser pipe,
In the 1000ml glass four-hole boiling flasks of water knockout drum, 2- methoxy-1-propanol 270g, acetic acid 198g, 2- methoxy-1-propanol are added
Mol ratio with acetic acid is 1: 1.1, and dehydrating agent hexamethylene is 135g, heats up and keeps reactant to be in fluidized state (75- all the time
150 DEG C), reflux water-dividing, 4h reactions terminate, and reactant is weighed and determines 2- methoxyl groups -1- third in reaction solution with gas chromatographic analysis
Alcohol acetate content, it is 97.3% to calculate reaction yield.
Esterification reaction product is subjected to two step rectifying, a small amount of unreacted 2- methoxy-1-propanols and vinegar are reclaimed in first rectifying
Acid (contains a small amount of hexamethylene dehydrating agent, do not influence to recycle), then rectifying obtains finished product 2- methoxy-1-propanol ether acetates, produces
Product purity 99.91%.Kettle liquid 1- containing catalyst butyl -3- methylimidazolium hydrogen sulphates salt and part 2- methoxyl groups -1- after rectifying
Propanol ether acetate needs recycled.
Embodiment 4
In equipped with thermometer, rectifying column, condenser pipe, the 1000ml glass four-hole boiling flasks of water knockout drum, addition 2- methoxyl groups-
The mol ratio of 1- propyl alcohol 270g, acetic acid 360g, 2- methoxy-1-propanol and acetic acid is 1: 2, acidic ionic liquid catalysts 1- fourths
Base -3- methylimidazolium hydrogen sulphate salt consumption is 6.3g, and dehydrating agent hexamethylene is 122g, heats up and keeps reactant all the time in boiling
State (75-150 DEG C) is risen, reflux water-dividing, 4h reactions terminate, and reactant is weighed and determines 2- first in reaction solution with gas chromatographic analysis
Oxy-1-propanol acetate ester content, it is 97.9% to calculate reaction yield.
Esterification reaction product is subjected to two step rectifying, a small amount of unreacted 2- methoxy-1-propanols and vinegar are reclaimed in first rectifying
Acid (contains a small amount of hexamethylene dehydrating agent, do not influence to recycle), then rectifying obtains finished product 2- methoxy-1-propanol ether acetates, produces
Product purity 99.91%.Kettle liquid 1- containing catalyst butyl -3- methylimidazolium hydrogen sulphates salt and part 2- methoxyl groups -1- after rectifying
Propanol ether acetate needs to be recycled.
Embodiment 5
In equipped with thermometer, rectifying column, condenser pipe, the 1000ml glass four-hole boiling flasks of water knockout drum, addition 2- methoxyl groups-
The mol 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 consumption is 18.8g, and dehydrating agent hexamethylene is 135g, heats up and keeps reactant to locate all the time
In fluidized state (75-150 DEG C), reflux water-dividing, 4h reactions terminate, and reactant is weighed to be determined in reaction solution with gas chromatographic analysis
2- methoxy-1-propanol ether acetate contents, it is 97.8% to calculate reaction yield.
Esterification reaction product is subjected to two step rectifying, a small amount of unreacted 2- methoxy-1-propanols and vinegar are reclaimed in first rectifying
Acid (contains a small amount of hexamethylene dehydrating agent, do not influence to recycle), then rectifying obtains finished product 2- methoxy-1-propanol ether acetates, produces
Product purity 99.92%.Kettle liquid 1- containing catalyst butyl -3- methylimidazolium hydrogen sulphates salt and part 2- methoxyl groups -1- after rectifying
Propanol ether acetate needs to be recycled.
Embodiment 6
In equipped with thermometer, rectifying column, condenser pipe, the 1000ml glass four-hole boiling flasks of water knockout drum, addition 2- methoxyl groups-
The mol 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 consumption is 4.7g, and dehydrating agent hexamethylene is 135g, heats up and keeps reactant to be in all the time
Fluidized state (75-150 DEG C), reflux water-dividing, 3h reactions terminate, and reactant is weighed and determines 2- in reaction solution with gas chromatographic analysis
Methoxy-1-propanol ether acetate content, it is 96.2% to calculate reaction yield.
Esterification reaction product is subjected to two step rectifying, a small amount of unreacted 2- methoxy-1-propanols and vinegar are reclaimed in first rectifying
Acid (contains a small amount of hexamethylene dehydrating agent, do not influence to recycle), then rectifying obtains finished product 2- methoxy-1-propanol ether acetates, produces
Product purity 99.91%.Kettle liquid 1- containing catalyst butyl -3- methylimidazolium hydrogen sulphates salt and part 2- methoxyl groups -1- after rectifying
Propanol ether acetate needs to be recycled.
Embodiment 7
In equipped with thermometer, rectifying column, condenser pipe, the 1000ml glass four-hole boiling flasks of water knockout drum, addition 2- methoxyl groups-
The mol 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 consumption is 4.7g, and dehydrating agent hexamethylene is 150g, heats up and keeps reactant to be in all the time
Fluidized state (75-145 DEG C), reflux water-dividing, 4h reactions terminate, and reactant is weighed and determines 2- in reaction solution with gas chromatographic analysis
Methoxy-1-propanol ether acetate content, it is 97.1% to calculate reaction yield.
Esterification reaction product is subjected to two step rectifying, a small amount of unreacted 2- methoxy-1-propanols and vinegar are reclaimed in first rectifying
Acid (contains a small amount of hexamethylene dehydrating agent, do not influence to recycle), then rectifying obtains finished product 2- methoxy-1-propanol ether acetates, produces
Product purity 99.91%.Kettle liquid 1- containing catalyst butyl -3- methylimidazolium hydrogen sulphates salt and part 2- methoxyl groups -1- after rectifying
Propanol ether acetate needs to be recycled.
Comparative example 1
In equipped with thermometer, rectifying column, condenser pipe, the 1000ml glass four-hole boiling flasks of water knockout drum, addition 2- methoxyl groups-
The mol 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 consumption is 4.7g, and dehydrating agent hexamethylene is 150g, heats up and keeps reactant all the time
In fluidized state (75-145 DEG C), reflux water-dividing, 4h reactions terminate, and reactant is weighed and determines reaction solution with gas chromatographic analysis
Middle 2- methoxy-1-propanol ether acetates content, it is 86.6% to calculate reaction yield.
Esterification reaction product is subjected to two step rectifying, a small amount of unreacted 2- methoxy-1-propanols and vinegar are reclaimed in first rectifying
Acid (contains a small amount of hexamethylene dehydrating agent, do not influence to recycle), then rectifying obtains finished product 2- methoxy-1-propanol ether acetates, produces
Product purity 97.62%.
Comparative example 2
In equipped with thermometer, rectifying column, condenser pipe, the 1000ml glass four-hole boiling flasks of water knockout drum, addition 2- methoxyl groups-
The mol 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 nitrates consumption is 4.7g, and dehydrating agent hexamethylene is 150g, heats up and keeps reactant all the time in boiling
State (75-145 DEG C) is risen, reflux water-dividing, 4h reactions terminate, and reactant is weighed and determines 2- first in reaction solution with gas chromatographic analysis
Oxy-1-propanol acetate ester content, it is 87.3% to calculate reaction yield.
Esterification reaction product is subjected to two step rectifying, a small amount of unreacted 2- methoxy-1-propanols and vinegar are reclaimed in first rectifying
Acid (contains a small amount of hexamethylene dehydrating agent, do not influence to recycle), then rectifying obtains finished product 2- methoxy-1-propanol ether acetates, produces
Product purity 96.64%.
Claims (8)
1. a kind of method that presence of acidic ionic liquid catalyst synthesizes 2- methoxy-1-propanol ether acetates, it is characterised in that：With 2- methoxies
Base -1- propyl alcohol is raw material with acetic acid, in acidic ionic liquid catalysts 1- butyl -3- methylimidazolium hydrogen sulphates salt and dehydrating agent ring
Under hexane collective effect, occur esterification synthesis 2- methoxy-1-propanol ether acetates；The water and hexamethylene generated in esterification
Alkane azeotropic distillation is removed；Esterification reaction product rectifying is obtained into 2- methoxy-1-propanol ether acetate products.
2. the method that presence of acidic ionic liquid catalyst according to claim 1 synthesizes 2- methoxy-1-propanol ether acetates, it is special
Levy and be：Described acidic ionic liquid catalysts 1- butyl -3- methylimidazolium hydrogen sulphate salt consumption is 2- methoxy-1-propanols
With the 0.2-8% of acetic acid quality.
3. the method that presence of acidic ionic liquid catalyst according to claim 1 synthesizes 2- methoxy-1-propanol ether acetates, it is special
Levy and be：Described 2- methoxy-1-propanols and the mol ratio of acetic acid are 1: 1-3.
4. the method that presence of acidic ionic liquid catalyst according to claim 1 synthesizes 2- methoxy-1-propanol ether acetates, it is special
Levy and be：The consumption of described dehydrating agent hexamethylene is the 45-55% of 2- methoxy-1-propanol quality.
5. the method that presence of acidic ionic liquid catalyst according to claim 1 synthesizes 2- methoxy-1-propanol ether acetates, it is special
Levy and be：Esterification reaction temperature is 75-150 DEG C.
6. the method that presence of acidic ionic liquid catalyst according to claim 1 synthesizes 2- methoxy-1-propanol ether acetates, it is special
Levy and be：Reaction time of esterification 2-4h.
7. the method that presence of acidic ionic liquid catalyst according to claim 1 synthesizes 2- methoxy-1-propanol ether acetates, it is special
Levy and be：Esterification reaction product is subjected to two step rectifying, a small amount of unreacted 2 one methoxy-1-propanol and vinegar are reclaimed in first rectifying
Acid, then rectifying obtain 2- methoxy-1-propanol ether acetate products.
8. the method that presence of acidic ionic liquid catalyst according to claim 1 synthesizes 2- methoxy-1-propanol ether acetates, it is special
Levy and be：Kettle liquid 1- containing catalyst butyl -3- methylimidazolium hydrogen sulphates salt and part 2- methoxy-1-propanol acetic acid after rectifying
Ester is recycled.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109265340A (en) * | 2018-11-19 | 2019-01-25 | 深圳市前海博扬研究院有限公司 | A kind of glycol ChanShuDing ether carboxylate and preparation method thereof |
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| JPH0725821A (en) * | 1993-07-15 | 1995-01-27 | Mitsubishi Chem Corp | New solvent and its production |
| CN101985418A (en) * | 2010-08-16 | 2011-03-16 | 江苏天音化工有限公司 | Method for preparing 2-methoxy-1-propanol ether acetate |
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2017
- 2017-04-21 CN CN201710264882.6A patent/CN107032986B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0725821A (en) * | 1993-07-15 | 1995-01-27 | Mitsubishi Chem Corp | New solvent and its production |
| CN101985418A (en) * | 2010-08-16 | 2011-03-16 | 江苏天音化工有限公司 | Method for preparing 2-methoxy-1-propanol ether acetate |
Non-Patent Citations (1)
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| 乔艳辉等: "1-甲基-3-丁基咪唑硫酸氢盐催化合成乙二醇丁醚乙酸酯", 《化工进展》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109265340A (en) * | 2018-11-19 | 2019-01-25 | 深圳市前海博扬研究院有限公司 | A kind of glycol ChanShuDing ether carboxylate and preparation method thereof |
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