CN103183611A - Preparation method of ethylene glycol monoalkyl ether acetate - Google Patents
Preparation method of ethylene glycol monoalkyl ether acetate Download PDFInfo
- Publication number
- CN103183611A CN103183611A CN2011104596513A CN201110459651A CN103183611A CN 103183611 A CN103183611 A CN 103183611A CN 2011104596513 A CN2011104596513 A CN 2011104596513A CN 201110459651 A CN201110459651 A CN 201110459651A CN 103183611 A CN103183611 A CN 103183611A
- Authority
- CN
- China
- Prior art keywords
- ethylene glycol
- sec
- glycol monoalkyl
- monoalkyl ether
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Abstract
The invention discloses a preparation method of ethylene glycol monoalkyl ether acetate. The preparation method is to take sec-butyl acetate and ethylene glycol monoalkyl ether as raw materials, and perform transesterification in the presence of a solid base catalyst to prepare ethylene glycol monoalkyl ether acetate. The preparation method comprises the steps of primary transesterification, breaking the chemical reaction equilibrium of transesterification, final-phase transesterification, separation and purification of the product ethylene glycol monoalkyl ether acetate, and the like. The preparation method of ethylene glycol monoalkyl ether acetate is high in the product yield, quick in reaction speed, low in energy consumption, easy to separation and purification of the products, low in cost and simple in the technique. In addition, by virtue of the synthetic method, another important common solvent sec-butyl alcohol can be obtained too. Therefore, the products are all required by application, the utilization ratio of the products is high, the three wastes are a little, and the preparation method is green and environment-friendly.
Description
Technical field
The present invention relates to the synthetic field of organic compound, relate in particular to a kind of method that ester-interchange method prepares ethylene glycol monoalkyl ether acetate of using.
Background technology
Ethylene glycol monoalkyl ether acetate is a class non-optical class non-pollution solvent that has aromatic odour commonly used.Possess ehter bond, carbonyl and alkyl in its molecule simultaneously, this polyfunctional group structures shape it have the character of alkyl oxide and acetic ester simultaneously, make its both solubilized small organic molecule, larger molecular organics and macromolecular compound, can dissolve each other with water or water-soluble cpds to some extent again, and it can form azeotrope with water.Therefore it has the not available performance of common organic solvents, can be used as cellosolve, high polymer solvent, rubber solvent and natural macromolecular compound solvent etc.In addition, make solvent with ethylene glycol monoalkyl ether acetate, can improve the performance of coating and printing ink, be lowered into film temperature, increase gloss, improve paint film adhesion, insulativity and anti-fastness.
Since ethylene glycol monoalkyl ether acetate came out, owing to its excellent property, be widely used, existing multiple homologue was succeeded in developing, and wherein a part has realized suitability for industrialized production, and its synthesis technique is updated.At present, the synthetic method of ethylene glycol monoalkyl ether acetate mainly contains three kinds of direct esterification method, one-step synthesis and ester-interchange methods.
The direct esterification method is to be raw material with acetic acid and ethylene glycol monoalkyl ether, with acid (as sulfuric acid) or Zeo-karb etc. as being that catalyst for making direct esterification is reacted and made product, this method water generation reaction, ethylene glycol monoalkyl ether acetate not only dissolved each other with water but also with can dissolve each other by unreacted organic raw material, form the close azeotrope of a series of boiling points, make the product separation difficulty, generally need to adopt the multistage rectification method, make the synthesis technique complexity, strengthen production cost, and can be in various degree in the product that rectifying gets moisture, influence the performance of solvent.One-step synthesis is to be raw material with oxyethane and methyl acetate, with ZrCl
4Or Zr (OPr)
4Being Primary Catalysts, is promotor with triethylamine or N-methylpyridone, and reaction makes product.This method raw materials cost is low, and the product purity height neither generates water in the reaction process, also do not generate ethanol, reactant is formed simple, and product separates easily, but this method by product is many, and multiple derivatives such as glycol ether and triglycol are arranged simultaneously, influences the gained end properties.Ester-interchange method generally is to be that raw material carries out the transesterification reaction synthetic product with ethyl acetate and ethylene glycol monoalkyl ether.This method reaction generates ethanol, do not exist owing to generating the problems that water brings, yet also can form the close azeotrope of multiple boiling point between product, raw material and the ethanol, refining separation difficulty, and the by product ethanol of this method is drained as waste liquid and is polluted the environment, produce waste, if the ethanol separation purification meaning of cheapness is also little.
Summary of the invention
The technical problem to be solved in the present invention is: provide a kind of product yield height, speed of response is fast, energy consumption is low, product separates purifies easily, the method for with low cost, the simple ethylene glycol monoalkyl ether acetate of technology.Another kind of product of the present invention is important common solvent sec-butyl alcohol in addition, makes that the product among the present invention all is to use needed product, product utilization rate height, few, the environmental protection of the three wastes.
In order to solve the problems of the technologies described above, the technical solution adopted in the present invention is:
A kind of preparation method of ethylene glycol monoalkyl ether acetate is raw material with sec-butyl acetate and ethylene glycol monoalkyl ether, carries out transesterification reaction and be prepared into ethylene glycol monoalkyl ether acetate in the presence of solid base catalyst, specifically may further comprise the steps:
1) preliminary transesterification reaction: under the solid base catalyst existence condition, sec-butyl acetate and ethylene glycol monoalkyl ether carry out initial transesterification reaction, wherein, the mol ratio of solid base catalyst, ethylene glycol monoalkyl ether, sec-butyl acetate is 0.01～0.08: 1: 0.9～1.5, this step reaction response temperature is 90～140 ℃, and the reaction times is 2～15h;
2) break the transesterify chemical reaction equilibrium: finish 1) maintain the temperature at 90～140 ℃ after the step, distill out the sec-butyl alcohol that generates in the step 1), detect the amount of the sec-butyl acetate that contains in the mixture that distills out in batches, and in former reaction system, add sec-butyl acetate, the amount of substance of the sec-butyl acetate of at every turn adding is 1～4 times of the amount of substance of the sec-butyl acetate that at every turn distills out, and the time that this step continues is 7～15h;
3) latter stage transesterification reaction: in step 2) in add for the last time add sec-butyl acetate after, keep 90～140 ℃ and proceed transesterification reaction 1～6h;
4) separation of glycol product monoalky lether acetic ester is purified: the ethylene glycol monoalkyl ether acetate that the mixture rectification and purification in the reaction vessel is obtained needs;
Preferably, further comprising the steps of: the mixture that contains sec-butyl alcohol that distills out the separation purification of product sec-butyl alcohol: to step 2) carries out rectification and purification and obtains sec-butyl alcohol.
Preferably, described ethylene glycol monoalkyl ether is the glycol monomethyl aliphatic ether.
Preferably, described glycol monomethyl aliphatic ether is a kind of in the following compounds: ethylene glycol monomethyl ether, ethylene glycol ethyl ether, butyl glycol ether.
Preferably, described solid base catalyst is KOH, K
2CO
3, NaOH, Na
2CO
3, CH
3ONa, C
2H
5The combination of one or more among the ONa.
Preferably, described solid base catalyst is K
2CO
3
Preferably, the mol ratio of solid base catalyst, ethylene glycol monoalkyl ether, sec-butyl acetate is 0.02: 1: 1.
Preferably, the described preliminary transesterification reaction time is 5～7h, and temperature is 110～120 ℃.
Preferably, describedly break that temperature is 110～120 ℃ in the transesterify chemical reaction equilibrium step, the amount of substance of the sec-butyl acetate of adding is 2 times of the amount of substances of the sec-butyl acetate that distills out.
Preferably, the reaction times of described last transesterification reaction is 2～3h, and temperature of reaction is 110～120 ℃.
The invention has the beneficial effects as follows: the present invention adopts sec-butyl acetate and ethylene glycol monoalkyl ether to carry out transesterification reaction under the effect of solid base catalyst and obtains ethylene glycol monoalkyl ether acetate and sec-butyl alcohol, uses sec-butyl acetate to replace ethyl acetate in traditional ester-interchange method as raw material.Make the present invention and can also obtain another important solvent sec-butyl alcohol commonly used the ethylene glycol monoalkyl ether acetate except obtaining, with respect to the secondary butyl ester of raw acetic acid and ethylene glycol monoalkyl ether, the value height of product, product of the present invention all is to use required product, make product utilization rate height, the combined coefficient height, few, the environmental protection of the three wastes.The raw material of sec-butyl alcohol and reaction and the few azeotropic of glycol product monoalky lether acetic ester among the present invention make the separation of product purify easily in addition.In the synthesis technique of the present invention, by distilling out product sec-butyl alcohol and hand in the chemical equilibrium that the reactant sec-butyl acetate is broken transesterification reaction retroactively, make the product yield height, and temperature of reaction and reaction times control is rationally among the present invention, technology is simple, and speed of response is fast, energy consumption is low.At last, the cheap and recyclable utilization of catalyzer in the synthetic method of the present invention.
Embodiment
The invention will be further elaborated below by concrete embodiment.
Embodiment one
(1) preliminary transesterification reaction:
339g (4.45mol) ethylene glycol monomethyl ether is added in the four-hole boiling flask of band separator column, reflux exchanger, thermometer, add 10g (0.072mol) K
2CO
3, add 517g (4.45mol) sec-butyl acetate, temperature is elevated to 110 ℃ of reaction 7h, in the reaction process, the temperature control of reflux exchanger backflow capital is below 100 ℃.
(2) break the transesterification reaction chemical equilibrium
After the previous step reaction is finished, maintain the temperature at 110 ℃, the sec-butyl alcohol that produces is steamed (wherein containing a spot of sec-butyl acetate and ethylene glycol monomethyl ether acetate), the content of sec-butyl acetate in the mixture that every interval 2h steams by gas chromatographic analysis, calculate the amount of the sec-butyl acetate that this section steam in the timed interval, and in reaction system, add sec-butyl acetate, the amount of the sec-butyl acetate of at every turn adding is 2 times of amount of the sec-butyl acetate that steams.This distills out sec-butyl alcohol, and to add the time that the process of sec-butyl acetate continues be 8h, adds sec-butyl acetate 210g (1.80mol) altogether, output sec-butyl alcohol mixed solution 555g.
(3) latter stage, transesterification reaction and product oxalic acid methyl ether acetate were purified
Continue after in step (2), adding sec-butyl acetate for the last time under 110 ℃ of temperature, to carry out transesterification reaction 2h.Be oxalic acid methyl ether acetate and a small amount of sec-butyl acetate of not participating in reaction this moment in the flask, and it is carried out rectifying, and rectification temperature is 125～135 ℃, can obtain oxalic acid methyl ether acetate product, and product advances the finished product jar.
(4) separation of product sec-butyl alcohol is purified
The made crude secbutyl alcohol of step (2) is carried out rectifying separation, but the sale of isolated sec-butyl alcohol finished product, and the secondary butyl ester that contains a small amount of ethylene glycol monomethyl ether that obtains carries out the recycle reaction.
Wherein, sec-butyl alcohol-sec-butyl acetate knockout tower: be a diameter 300mm from tower, the packing tower of high 16000mm, interior dress structured packing, number of theoretical plate is 100.Sec-butyl alcohol-sec-butyl acetate mixed solution directly enters the middle and lower part of knockout tower, the tower reactor reboiler provides by outer heat and separates whole energy, trim the top of column is than 5,105～110 ℃ of tower top temperatures, 120～125 ℃ of tower reactor temperature, working pressure is normal pressure, through gas chromatographic analysis, cat head can obtain the sec-butyl alcohol of purity 99.1%, and it is 98% that tower reactor can obtain sec-butyl acetate purity, the mixture of sec-butyl alcohol 2%.
(5) product purity analysis
Product purity adopts vapor-phase chromatography to detect:
Testing conditions is: Agilent 7820A, capillary chromatographic column, fid detector, 300 ℃ of injector temperatures, 325 ℃ of the highest column temperatures, 300 ℃ of detected temperatures, H
2Flow: 30mL/min, air flow quantity: 300mL/min, N
2Flow: 25mL/min.
After testing, the purity of product ethylene glycol monomethyl ether acetate is 97.8%, and the purity of sec-butyl alcohol is: 99.1%.
Embodiment two
(1) preliminary transesterification reaction:
With 185kg (2431mol) ethylene glycol monomethyl ether, 6.5kg (47mol) K
2CO
3And 304kg (2617mol) 2-butyl acetate adds the 1m of band separator column, reflux exchanger, thermometer
3In the stainless steel cauldron, start whipping appts and heating unit, in 3 hours temperature is elevated to 120 ℃, and keep 120 ℃ to react 5h down,, to guarantee the material in reactor temperature in the ester-exchange reaction less than 125 ℃, the top temperature of reflux exchanger reflux column is less than 100 ℃.
(2) break the transesterification reaction chemical equilibrium
This step is similar to a kind of step of embodiment (2), wherein the additional amount of 2-butyl acetate is 1.2 times of its amount of steaming, add in the process of 2-butyl acetate at the whole sec-butyl alcohol that steams, the temperature of material in reactor remains on 120 ℃, the top temperature of reflux column is less than 100 ℃, this process continues 10 hours, adds 2-butyl acetate 208kg (1791mol) altogether.
(3) latter stage, transesterification reaction and product oxalic acid methyl ether acetate were purified
Continue add 2-butyl acetate for the last time in step (2) after to keep 120 ℃ of transesterification reactions 3 hours, in whole process, the top temperature of reflux column is less than 100 ℃.Be oxalic acid methyl ether acetate and a small amount of sec-butyl acetate of not participating in reaction this moment in the flask, and it is carried out rectifying, and rectification temperature is 125～135 ℃, and the top temperature of reflux column can obtain oxalic acid methyl ether acetate product less than 100 ℃, and product advances the finished product jar.
(4) sec-butyl alcohol-2-butyl acetate separates:
With the step in the example one (4);
(5) analysis of product purity:
With the step in the example one (5), after testing, the purity of product glycol methyl ether acetate is 99.3%, and the purity of sec-butyl alcohol is 99.1%.
Example three
(1) preliminary transesterification reaction
1.11 tons of (14.6kmol) ethylene glycol monomethyl ether, 0.006 ton of (0.15kmol) NaOH and 1.8 tons of (15.5kmol) 2-butyl acetates are added the 6m that is with separator column, reflux exchanger, thermometer
3In the stainless steel cauldron, start whipping appts and heating unit, in the 5h temperature is elevated to 100 ℃, and in 100 ℃ of transesterification reactions, reaction times 12h.
(2) break the transesterification reaction chemical equilibrium
This step is similar to a kind of step of embodiment (2), wherein the additional amount of each 2-butyl acetate is 3 times of its amount of steaming, add in the process of 2-butyl acetate at the whole sec-butyl alcohol that steams, the temperature of material in reactor remains on 100 ℃, this process continues 20h, adds 1.2 tons of 2-butyl acetates (10.3kmol) altogether.
(3) latter stage, transesterification reaction and product oxalic acid methyl ether acetate were purified
Continue to keep 100 ℃ of transesterification reaction 6h after in step (2), adding 2-butyl acetate for the last time.Be oxalic acid methyl ether acetate and a small amount of sec-butyl acetate of not participating in reaction this moment in the flask, and it is carried out rectifying, and rectification temperature is 125～135 ℃, can obtain oxalic acid methyl ether acetate product, and product advances the finished product jar.
(4) sec-butyl alcohol and secondary butyl ester separates
With the step among the embodiment one (4).
(5) analysis of product purity
With the step among the embodiment one (5).
Detect through chromatogram, the purity of product glycol methyl ether acetate is 99.4%, and the purity of sec-butyl alcohol is 99.1%.
Embodiment four
(1) preliminary transesterification reaction
With 285g (3.16mol) ethylene glycol ethyl ether, 2.9g (0.043mol) C
2H
5ONa and 522g (4.49mol) 2-butyl acetate adds in the four-hole boiling flask of band separator column, reflux exchanger, thermometer, starts stirring, slowly heats up after half an hour, and temperature is elevated to 130 ℃ of reaction 3h.
(2) break the transesterification reaction chemical equilibrium
This step is similar to a kind of step of embodiment (2), wherein the additional amount of each 2-butyl acetate is 4 times of its amount of steaming, add in the process of 2-butyl acetate at the whole sec-butyl alcohol that steams, the temperature of material in reactor remains on 130 ℃, this process continues 10h, add 2-butyl acetate 197g (1.70mol) altogether, output sec-butyl alcohol mixed solution 372g.
(3) latter stage, transesterification reaction and product oxalic acid methyl ether acetate were purified
Continue to keep 130 ℃ of transesterification reaction 2h after in step (2), adding 2-butyl acetate for the last time.Be oxalic acid methyl ether acetate and a small amount of sec-butyl acetate of not participating in reaction this moment in the flask, and it is carried out rectifying, and rectification temperature is 130～140 ℃, can obtain oxalic acid methyl ether acetate product, and product advances the finished product jar.
(4) sec-butyl alcohol-2-butyl acetate separates:
With the step among the embodiment one (4).
(5) analysis of product purity
With the step among the embodiment one (5), after testing, the purity of product ethylene glycol ether acetate is 96.8%, and the purity of sec-butyl alcohol is 99.1%.
Embodiment five
(1) preliminary transesterification reaction
With 49kg (544mol) ethylene glycol ethyl ether, 1.5kg K
2CO
3(10.8mol) and 60kg (516mol) 2-butyl acetate add the 150L stainless steel cauldron of band separator column, reflux exchanger, thermometer, start stirring, slowly heat up after half an hour, temperature is elevated to 110 ℃ of reaction 4h.
(2) break the transesterification reaction chemical equilibrium
This step is similar to a kind of step of embodiment (2), wherein the additional amount of each 2-butyl acetate is 2 times of its amount of steaming, add in the process of 2-butyl acetate at the whole sec-butyl alcohol that steams, the temperature of material in reactor remains on 110 ℃, this process continues 10h, adds 2-butyl acetate 40kg (344mo1) altogether.
(3) latter stage, transesterification reaction and product oxalic acid methyl ether acetate were purified
Continue after in step (2), adding sec-butyl acetate for the last time under 110 ℃ of temperature, to carry out transesterification reaction 3h.Be oxalic acid methyl ether acetate and a small amount of sec-butyl acetate of not participating in reaction this moment in the flask, and it is carried out rectifying, and rectification temperature is 130～140 ℃, can obtain oxalic acid methyl ether acetate product, and product advances the finished product jar.
(4) sec-butyl alcohol-2-butyl acetate separates
With the step among the embodiment one (4).
(5) analysis of product purity
With the step among the embodiment one (5), after testing, the purity of product ethylene glycol ether acetate is 98.8%, and the purity of sec-butyl alcohol is: 99.1%.
Embodiment six
(1) initial transesterification reaction:
With 1.4 tons of (15.5kmol) ethylene glycol ethyl ethers, 50kg K
2CO
3(0.36kmol) add the 6m that is with separator column, reflux exchanger, thermometer with 1.8 tons of (15.5kmol) 2-butyl acetates
3Stainless steel cauldron starts stirring, slowly heats up after half an hour, temperature is elevated to 115 ℃ reacts 5h.
(2) break the transesterification reaction chemical equilibrium
This step is similar to a kind of step of embodiment (2), wherein the additional amount of each 2-butyl acetate is 2 times of its amount of steaming, add in the process of 2-butyl acetate at the whole sec-butyl alcohol that steams, the temperature of material in reactor remains on 114 ℃, this process continues 14h, adds 2-butyl acetate 1400kg (12kmol) altogether.
(3) latter stage, transesterification reaction and product oxalic acid methyl ether acetate were purified
Change under 120 ℃ of temperature after in step (2), adding sec-butyl acetate for the last time and carry out transesterification reaction 5h.Be oxalic acid methyl ether acetate and a small amount of sec-butyl acetate of not participating in reaction this moment in the flask, and it is carried out rectifying, and rectification temperature is 130～140 ℃, can obtain oxalic acid methyl ether acetate product, and product advances the finished product jar.
(4) sec-butyl alcohol-2-butyl acetate separates:
With the step among the embodiment one (4).
(5) analysis of product purity
With the step among the embodiment one (5), after testing, the purity of product ethylene glycol ether acetate is 99.5%, and the purity of sec-butyl alcohol is: 99.1%.
The equivalence explanation
More than to the clear preparation method's product yield height that ethylene glycol monoalkyl ether acetate of the present invention has been described of specific descriptions of the present invention, speed of response is fast, energy consumption is low, product separates purifies easily, with low cost, technology is simple, product utilization rate advantages of higher.Although specific embodiment here describes in detail, this is only as the explanation of technical solution problem of the present invention, and does not limit claims to the scope of claim of the present invention.Particularly point out, the inventor is through careful consideration, and the replacement that the present invention is different, change do not depart from the defined the connotation and extension of claim of the present invention.
Claims (10)
1. the preparation method of an ethylene glycol monoalkyl ether acetate, it is characterized in that: be raw material with sec-butyl acetate and ethylene glycol monoalkyl ether, in the presence of solid base catalyst, carry out transesterification reaction and be prepared into ethylene glycol monoalkyl ether acetate, specifically may further comprise the steps:
1) preliminary transesterification reaction: under the solid base catalyst existence condition, sec-butyl acetate and ethylene glycol monoalkyl ether carry out initial transesterification reaction, wherein, the mol ratio of solid base catalyst, ethylene glycol monoalkyl ether, sec-butyl acetate is 0.01～0.08: 1: 0.9～1.5, this step reaction response temperature is 90～140 ℃, and the reaction times is 2～15h;
2) break the transesterify chemical reaction equilibrium: finish 1) maintain the temperature at 90～140 ℃ after the step, distill out the sec-butyl alcohol that generates in the step 1), detect the amount of the sec-butyl acetate that contains in the mixture that distills out in batches, and in former reaction system, add sec-butyl acetate, the amount of substance of the sec-butyl acetate of at every turn adding is 1～4 times of the amount of substance of the sec-butyl acetate that at every turn distills out, and the time that this step continues is 7～20h;
3) latter stage transesterification reaction: in step 2) in add for the last time add sec-butyl acetate after, keep 90～140 ℃ of temperature and proceed transesterification reaction 1～6h;
4) separation of glycol product monoalky lether acetic ester is purified: the ethylene glycol monoalkyl ether acetate that the mixture rectification and purification in the reaction vessel is obtained needs.
2. the preparation method of ethylene glycol monoalkyl ether acetate according to claim 1 is characterized in that: further comprising the steps of:
The separation purification of product sec-butyl alcohol: to step 2) mixture that contains sec-butyl alcohol that distills out in carries out rectification and purification and obtains sec-butyl alcohol.
3. the preparation method of ethylene glycol monoalkyl ether acetate according to claim 1, it is characterized in that: described ethylene glycol monoalkyl ether is the glycol monomethyl aliphatic ether.
4. the preparation method of ethylene glycol monoalkyl ether acetate according to claim 3 is characterized in that: described glycol monomethyl aliphatic ether is a kind of in the following compounds: ethylene glycol monomethyl ether, ethylene glycol ethyl ether, butyl glycol ether.
5. the preparation method of ethylene glycol monoalkyl ether acetate according to claim 1, it is characterized in that: described solid base catalyst is KOH, K
2CO
3, NaOH, Na
2CO
3, CH
3ONa, C
2H
5The combination of one or more among the ONa.
6. the preparation method of ethylene glycol monoalkyl ether acetate according to claim 5, it is characterized in that: described solid base catalyst is K
2CO
3
7. the preparation method of ethylene glycol monoalkyl ether acetate according to claim 1, it is characterized in that: the mol ratio of solid base catalyst, ethylene glycol monoalkyl ether, sec-butyl acetate is 0.02: 1: 1.
8. the preparation method of ethylene glycol monoalkyl ether acetate according to claim 1, it is characterized in that: the described preliminary transesterification reaction time is 5～7h, and temperature is 110～120 ℃.
9. the preparation method of ethylene glycol monoalkyl ether acetate according to claim 1, it is characterized in that: describedly break that temperature of reaction is 110～120 ℃ in the transesterify chemical reaction equilibrium step, the amount of substance of the sec-butyl acetate of adding is 2 times of the amount of substances of the sec-butyl acetate that distills out.
10. the preparation method of ethylene glycol monoalkyl ether acetate according to claim 1 is characterized in that: the reaction times of described last transesterification reaction is 2～3h, and temperature of reaction is 110～120 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110459651.3A CN103183611B (en) | 2011-12-31 | 2011-12-31 | Preparation method of ethylene glycol monoalkyl ether acetate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110459651.3A CN103183611B (en) | 2011-12-31 | 2011-12-31 | Preparation method of ethylene glycol monoalkyl ether acetate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103183611A true CN103183611A (en) | 2013-07-03 |
| CN103183611B CN103183611B (en) | 2015-01-07 |
Family
ID=48675090
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201110459651.3A Active CN103183611B (en) | 2011-12-31 | 2011-12-31 | Preparation method of ethylene glycol monoalkyl ether acetate |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103183611B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107445824A (en) * | 2017-06-22 | 2017-12-08 | 江门谦信化工发展有限公司 | A kind of alcohol solvent of ether ester type energy-efficient reaction process and its reaction system |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU734182A1 (en) * | 1977-07-07 | 1980-05-15 | Ярославский политехнический институт | Method of producing secondary butanol |
| CN1197790A (en) * | 1997-04-30 | 1998-11-04 | 石伟 | Preparation of acetate product |
-
2011
- 2011-12-31 CN CN201110459651.3A patent/CN103183611B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU734182A1 (en) * | 1977-07-07 | 1980-05-15 | Ярославский политехнический институт | Method of producing secondary butanol |
| CN1197790A (en) * | 1997-04-30 | 1998-11-04 | 石伟 | Preparation of acetate product |
Non-Patent Citations (1)
| Title |
|---|
| 龚国珍 等: "固体碱K2CO3/Al2O3催化酯交换法合成乙二醇甲醚乙酸酯", 《精细化工》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107445824A (en) * | 2017-06-22 | 2017-12-08 | 江门谦信化工发展有限公司 | A kind of alcohol solvent of ether ester type energy-efficient reaction process and its reaction system |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103183611B (en) | 2015-01-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN110613946B (en) | Backpack reaction rectification equipment for synthesizing diethyl oxalate and process thereof | |
| CN103183611B (en) | Preparation method of ethylene glycol monoalkyl ether acetate | |
| CN106349062A (en) | Method for synthesizing diethyleneglycol diformate by composite catalyst | |
| CN112679346A (en) | Method for catalytically synthesizing p-tert-butyl methyl benzoate based on eutectic solvent | |
| CN208182888U (en) | Reactive distillation-film device coupling production ethyl acetate in high purity device | |
| CN113200853A (en) | Process method for preparing butanediol succinate | |
| CN104892400B (en) | Catalyze and synthesize oxalic acid intermittent reaction and continuous reaction rectification group technology | |
| CN103183609B (en) | Preparation method of ethylene glycol monoacetate and ethylene glycol diacetate | |
| CN103265429A (en) | Technical method for synthesizing methyl acetate | |
| CN106518676A (en) | Method for preparing methyl methoxyacetate by industrial aqueous raw material methylal | |
| CN112592274B (en) | Process for synthesizing methyl p-hydroxyphenylpropionate | |
| CN114105769A (en) | Method for catalytically synthesizing n-propyl cinnamate based on choline chloride eutectic solvent | |
| CN104945255A (en) | Preparation method of cyclohexyl methacrylate | |
| CN103709032B (en) | The preparation method of the ionic liquid-catalyzed carbonate synthesis dibutylester of a kind of proline(Pro) class | |
| CN109810011B (en) | Preparation method of N-isobornyl acrylamide | |
| CN104892557A (en) | Asymmetric syntheses method of chiral dihydrocoumarin derivative | |
| CN107032986B (en) | A kind of method of presence of acidic ionic liquid catalyst synthesis 2- methoxy-1-propanol ether acetate | |
| CN102850270A (en) | Method for preparing hydroxy substituted-3,4-dihydro-2(1H)-quinolinone compound by one-pot method | |
| CN107602516B (en) | Method for synthesizing delta-cyclopentanolide under catalysis of amino acid ionic liquid | |
| CN103232325B (en) | A kind of method being prepared hexalin by tetrahydrobenzene | |
| CN106380398A (en) | A green synthetic method for tert-butyl bromoacetate | |
| CN101693646B (en) | Process for preparing dichloropropanol through glycerol chlorination method | |
| CN110078588B (en) | Preparation method of 1, 3-propylene glycol | |
| CN112691703B (en) | Double-salt ionic liquid catalyst for methyl acetate hydrolysis reaction and application thereof | |
| CN112569620B (en) | Process system for preparing cyclopentyl methyl ether by using bulkhead reaction rectifying tower |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C53 | Correction of patent of invention or patent application | ||
| CB02 | Change of applicant information |
Address after: 518000, Guangdong City, Baoan District province Xin'an Shenzhen street, Xian Xian two road flying Industrial Science and technology plant, B building, nine floor Applicant after: SHENZHEN FEIYANG JUNYAN TECHNOLOGY DEVELOPMENT Co.,Ltd. Applicant after: ZHUHAI FEIYANG NOVEL MATERIALS Corp.,Ltd. Address before: 518101 Guangdong city of Shenzhen province Nanshan District Huaming road Nanyou A District 20 building 402 room Applicant before: SHENZHEN FEIYANG JUNYAN TECHNOLOGY DEVELOPMENT Co.,Ltd. Applicant before: Zhuhai Feiyang Chemical Co.,Ltd. |
|
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C41 | Transfer of patent application or patent right or utility model | ||
| C56 | Change in the name or address of the patentee | ||
| CP03 | Change of name, title or address |
Address after: 518000, Guangdong City, Baoan District province Xin'an Shenzhen street, Xian Xian two road flying Industrial Science and technology plant, B building, nine floor Patentee after: SHENZHEN FEIYANG JUNYAN NEW MATERIAL CO.,LTD. Patentee after: ZHUHAI FEIYANG NOVEL MATERIALS Corp.,Ltd. Address before: Shenzhen City, Guangdong province Baoan District Xin'an street, Xian Xian two road flying industrial technology factory building B, nine floor Patentee before: SHENZHEN FEIYANG JUNYAN TECHNOLOGY DEVELOPMENT Co.,Ltd. Patentee before: ZHUHAI FEIYANG NOVEL MATERIALS Corp.,Ltd. |
|
| TR01 | Transfer of patent right |
Effective date of registration: 20160727 Address after: 519000 Guangdong province Zhuhai Gaolan Port Economic Zone Petrochemical Zone five North Road Feiyang chemical plant Patentee after: ZHUHAI FEIYANG NOVEL MATERIALS Corp.,Ltd. Address before: Shenzhen City, Guangdong province Baoan District Xin'an street, Xian Xian two road flying industrial technology factory building B, nine floor Patentee before: SHENZHEN FEIYANG JUNYAN NEW MATERIAL CO.,LTD. Patentee before: ZHUHAI FEIYANG NOVEL MATERIALS Corp.,Ltd. |