CN103183611B - Preparation method of ethylene glycol monoalkyl ether acetate - Google Patents
Preparation method of ethylene glycol monoalkyl ether acetate Download PDFInfo
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- CN103183611B CN103183611B CN201110459651.3A CN201110459651A CN103183611B CN 103183611 B CN103183611 B CN 103183611B CN 201110459651 A CN201110459651 A CN 201110459651A CN 103183611 B CN103183611 B CN 103183611B
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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 synthesis field of organic compound, particularly relate to a kind of method applied ester-interchange method and prepare ethylene glycol monoalkyl ether acetate.
Background technology
Ethylene glycol monoalkyl ether acetate is the non-optical class non-pollution solvent with aromatic odour that a class is commonly used.Possess ehter bond, carbonyl and alkyl in its molecule simultaneously, this polyfunctional group structures shape it there is 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 performance not available for 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, the performance of coating and ink can be improved, be lowered into film temperature, increase gloss, improve the sticking power of paint film, insulativity and resistance to fastness.
Ethylene glycol monoalkyl ether acetate due to its excellent property, has been widely used since coming out, and existing multiple homologue is succeeded in developing, and wherein a part realizes suitability for industrialized production, and its synthesis technique is updated.At present, the synthetic method of ethylene glycol monoalkyl ether acetate mainly contains direct esterification, one-step synthesis and ester-interchange method three kinds.
Direct esterification is for raw material with acetic acid and ethylene glycol monoalkyl ether, product is obtained as catalyst for making direct esterification reaction using acid (as sulfuric acid) or Zeo-karb etc., 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 azeotrope that a series of boiling point is close, make product separation difficulty, generally need adopt multistage rectification method, make synthesis technique complicated, strengthen production cost, and can in various degree moisture in the product that obtains of rectifying, affect the performance of solvent.One-step synthesis is with oxyethane and methyl acetate for raw material, with ZrCl
4or Zr (OPr)
4for Primary Catalysts, with triethylamine or N-methylpyridone for promotor, the obtained product of reaction.This method raw materials cost is low, and product purity is high, neither generates water in reaction process, also do not generate ethanol, reactant composition is simple, and product is easily separated, but this method by product is many, there is the multiple derivative such as glycol ether and triglycol simultaneously, affect gained end properties.Ester-interchange method is generally for raw material carries out transesterification reaction synthetic product with ethyl acetate and ethylene glycol monoalkyl ether.This method reaction generates ethanol, there are not the problems brought owing to generating water, but product, between raw material and ethanol, also can form the close azeotrope of multiple boiling point, refining spearation difficulty, and the coproduct ethanol of this method is drained pollute the environment as waste liquid, produce waste, if by also little for the separation of ethanol purification meaning of cheapness.
Summary of the invention
The technical problem to be solved in the present invention is: provide that a kind of product yield is high, speed of response is fast, energy consumption is low, and product separation is purified easily, the method for the simple ethylene glycol monoalkyl ether acetate of with low cost, technique.Another kind of product of the present invention is important common solvent sec-butyl alcohol in addition, and make the product of product all required for application in the present invention, product utilization rate is high, and the three wastes are few, environmental protection.
In order to solve the problems of the technologies described above, the technical solution adopted in the present invention is:
A preparation method for ethylene glycol monoalkyl ether acetate, with sec-butyl acetate and ethylene glycol monoalkyl ether for raw material, carries out transesterification reaction and is prepared into ethylene glycol monoalkyl ether acetate, specifically comprise the following steps under solid base catalyst exists:
1) preliminary transesterification reaction: under 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 DEG C, and the reaction times is 2 ~ 15h;
2) transesterify chemical reaction equilibrium is broken: complete 1) maintain the temperature at 90 ~ 140 DEG C after step, distill out step 1) the middle sec-butyl alcohol generated, detect the amount of the sec-butyl acetate contained in the mixture distilled out in batches, and sec-butyl acetate is added in former reaction system, the amount of substance of the sec-butyl acetate at every turn added is the amount of substance 1 ~ 4 times of the sec-butyl acetate at every turn distilled 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 and add sec-butyl acetate after, maintain 90 ~ 140 DEG C and proceed transesterification reaction 1 ~ 6h;
4) separating-purifying of glycol product monoalkyl ether acetate: the mixture rectification and purification in reaction vessel is obtained to the ethylene glycol monoalkyl ether acetate needed;
Preferably, further comprising the steps of: the separating-purifying of product sec-butyl alcohol: to step 2) in distill out carry out rectification and purification containing the mixture of sec-butyl alcohol and obtain sec-butyl alcohol.
Preferably, described ethylene glycol monoalkyl ether is ethylene glycol list aliphatic ether.
Preferably, described ethylene glycol list aliphatic ether is the one in 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
5one or more combination in 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 DEG C.
Preferably, described in break temperature in transesterify chemical reaction equilibrium step be 110 ~ 120 DEG C, the amount of substance of the sec-butyl acetate added is the amount of substance 2 times of the sec-butyl acetate distilled out.
Preferably, the reaction times of described last transesterification reaction is 2 ~ 3h, and temperature of reaction is 110 ~ 120 DEG C.
The invention has the beneficial effects as follows: the present invention adopts sec-butyl acetate and ethylene glycol monoalkyl ether under the effect of solid base catalyst, carry out transesterification reaction and obtains ethylene glycol monoalkyl ether acetate and sec-butyl alcohol, use sec-butyl acetate to replace ethyl acetate in traditional ester-interchange method as raw material.Make the present invention can also obtain another conventional important solvent sec-butyl alcohol except can obtaining ethylene glycol monoalkyl ether acetate, relative to the secondary butyl ester of raw acetic acid and ethylene glycol monoalkyl ether, the value of product is high, the product of product of the present invention all needed for application, make product utilization rate high, combined coefficient is high, and the three wastes are few, environmental protection.The raw material of sec-butyl alcohol and reaction in the present invention and the few azeotropic of glycol product monoalkyl ether acetate, make the separating-purifying of product easy in addition.In synthesis technique of the present invention, by distilling out product sec-butyl alcohol and hand in the chemical equilibrium that reactant sec-butyl acetate breaks transesterification reaction retroactively, make product yield high, and in the present invention temperature of reaction and reaction times control rationally, technique is simple, and speed of response is fast, energy consumption is low.Finally, the cheap and recoverable of catalyzer in synthetic method of the present invention.
Embodiment
Below by concrete embodiment, the invention will be further elaborated.
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 DEG C of reaction 7h, in reaction process, the temperature control of reflux exchanger backflow capital is less than 100 DEG C.
(2) transesterification reaction chemical equilibrium is broken
After previous step has been reacted, maintain the temperature at 110 DEG C, the sec-butyl alcohol of generation is steamed (wherein containing a small amount of sec-butyl acetate and ethylene glycol monomethyl ether acetate), the content of sec-butyl acetate in the mixture steamed by gas chromatographic analysis at interval of 2h, calculate the amount of the sec-butyl acetate steamed in this period of timed interval, and sec-butyl acetate is added in reaction system, the amount of the sec-butyl acetate at every turn added is 2 times of the amount of sec-butyl acetate of steaming.This time distilling out that sec-butyl alcohol adds the process lasts of sec-butyl acetate is 8h, adds altogether sec-butyl acetate 210g (1.80mol), output sec-butyl alcohol mixed solution 555g.
(3) latter stage transesterification reaction and product oxalic acid methyl ether acetate purify
Continue add sec-butyl acetate for the last time in step (2) after to carry out transesterification reaction 2h at 110 DEG C of temperature.Be now oxalic acid methyl ether acetate and the sec-butyl acetate not participating in reaction on a small quantity in flask, carry out rectifying to it, rectification temperature is 125 ~ 135 DEG C, can obtain oxalic acid methyl ether acetate product, and product enters finished pot.
(4) separating-purifying of product sec-butyl alcohol
Step (2) made crude secbutyl alcohol is carried out rectifying separation, and isolated sec-butyl alcohol can be sold by finished product, and the secondary butyl ester containing a small amount of ethylene glycol monomethyl ether obtained carries out recycle reaction.
Wherein, sec-butyl alcohol-sec-butyl acetate knockout tower: be a diameter 300mm from tower, the packing tower of high 16000mm, in-built structured packing, number of theoretical plate is 100 pieces.Sec-butyl alcohol-sec-butyl acetate mixed solution directly enters the middle and lower part of knockout tower, tower reactor reboiler is provided by outer heat and is separated whole energy, trim the top of column is than 5, tower top temperature 105 ~ 110 DEG C, bottom temperature 120 ~ 125 DEG C, working pressure is normal pressure, through gas chromatographic analysis, tower top 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, injector temperature 300 DEG C, the highest column temperature 325 DEG C, detected temperatures 300 DEG C, 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:
By 185kg (2431mol) ethylene glycol monomethyl ether, 6.5kg (47mol) K
2cO
3the 1m of band separator column, reflux exchanger, thermometer is added with 304kg (2617mol) 2-butyl acetate
3in stainless steel cauldron, start whipping appts and heating unit, in 3 hours, temperature is elevated to 120 DEG C, and react 5h at keeping 120 DEG C,, will guarantee in ester-exchange reaction that material in reactor temperature is less than 125 DEG C, the top temperature of reflux exchanger reflux column is less than 100 DEG C.
(2) transesterification reaction chemical equilibrium is broken
This step is similar to a kind of step (2) of embodiment, 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 DEG C, the top temperature of reflux column is less than 100 DEG C, this process lasts 10 hours, adds altogether 2-butyl acetate 208kg (1791mol).
(3) latter stage transesterification reaction and product oxalic acid methyl ether acetate purify
Continue maintenance 120 DEG C of transesterification reactions add 2-butyl acetate for the last time in step (2) after 3 hours, in whole process, the top temperature of reflux column is less than 100 DEG C.Be now oxalic acid methyl ether acetate and the sec-butyl acetate not participating in reaction on a small quantity in flask, carry out rectifying to it, rectification temperature is 125 ~ 135 DEG C, and the top temperature of reflux column is less than 100 DEG C, can obtain oxalic acid methyl ether acetate product, and product enters finished pot.
(4) sec-butyl alcohol-2-butyl acetate is separated:
With the step (4) in example one;
(5) analysis of product purity:
With the step (5) in example one, 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 ton of (15.5kmol) 2-butyl acetate are added the 6m being with separator column, reflux exchanger, thermometer
3in stainless steel cauldron, start whipping appts and heating unit, in 5h, temperature is elevated to 100 DEG C, and in 100 DEG C of transesterification reactions, reaction times 12h.
(2) transesterification reaction chemical equilibrium is broken
This step is similar to a kind of step (2) of embodiment, 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 DEG C, this process lasts 20h, adds altogether 2-butyl acetate 1.2 tons (10.3kmol).
(3) latter stage transesterification reaction and product oxalic acid methyl ether acetate purify
Maintenance 100 DEG C of transesterification reaction 6h are continued add 2-butyl acetate for the last time in step (2) after.Be now oxalic acid methyl ether acetate and the sec-butyl acetate not participating in reaction on a small quantity in flask, carry out rectifying to it, rectification temperature is 125 ~ 135 DEG C, can obtain oxalic acid methyl ether acetate product, and product enters finished pot.
(4) being separated of sec-butyl alcohol and secondary butyl ester
With the step (4) in embodiment one.
(5) analysis of product purity
With the step (5) in embodiment one.
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
By 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, temperature is elevated to 130 DEG C of reaction 3h.
(2) transesterification reaction chemical equilibrium is broken
This step is similar to a kind of step (2) of embodiment, 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 DEG C, this process lasts 10h, add altogether 2-butyl acetate 197g (1.70mol), output sec-butyl alcohol mixed solution 372g.
(3) latter stage transesterification reaction and product oxalic acid methyl ether acetate purify
Maintenance 130 DEG C of transesterification reaction 2h are continued add 2-butyl acetate for the last time in step (2) after.Be now oxalic acid methyl ether acetate and the sec-butyl acetate not participating in reaction on a small quantity in flask, carry out rectifying to it, rectification temperature is 130 ~ 140 DEG C, can obtain oxalic acid methyl ether acetate product, and product enters finished pot.
(4) sec-butyl alcohol-2-butyl acetate is separated:
With the step (4) in embodiment one.
(5) analysis of product purity
With the step (5) in embodiment one, 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
By 49kg (544mol) ethylene glycol ethyl ether, 1.5kg K
2cO
3(10.8mol) add the 150L stainless steel cauldron of band separator column, reflux exchanger, thermometer with 60kg (516mol) 2-butyl acetate, start stirring, slowly heat up after half an hour, temperature is elevated to 110 DEG C of reaction 4h.
(2) transesterification reaction chemical equilibrium is broken
This step is similar to a kind of step (2) of embodiment, 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 DEG C, this process lasts 10h, adds altogether 2-butyl acetate 40kg (344mo1).
(3) latter stage transesterification reaction and product oxalic acid methyl ether acetate purify
Continue add sec-butyl acetate for the last time in step (2) after to carry out transesterification reaction 3h at 110 DEG C of temperature.Be now oxalic acid methyl ether acetate and the sec-butyl acetate not participating in reaction on a small quantity in flask, carry out rectifying to it, rectification temperature is 130 ~ 140 DEG C, can obtain oxalic acid methyl ether acetate product, and product enters finished pot.
(4) sec-butyl alcohol-2-butyl acetate is separated
With the step (4) in embodiment one.
(5) analysis of product purity
With the step (5) in embodiment one, 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:
By 1.4 tons of (15.5kmol) ethylene glycol ethyl ethers, 50kg K
2cO
3(0.36kmol) He 1.8 tons of (15.5kmol) 2-butyl acetates add the 6m of band separator column, reflux exchanger, thermometer
3stainless steel cauldron, starts stirring, slowly heats up after half an hour, temperature is elevated to 115 DEG C and carries out reaction 5h.
(2) transesterification reaction chemical equilibrium is broken
This step is similar to a kind of step (2) of embodiment, 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 DEG C, this process lasts 14h, adds altogether 2-butyl acetate 1400kg (12kmol).
(3) latter stage transesterification reaction and product oxalic acid methyl ether acetate purify
Change into add sec-butyl acetate for the last time in step (2) after and carry out transesterification reaction 5h at 120 DEG C of temperature.Be now oxalic acid methyl ether acetate and the sec-butyl acetate not participating in reaction on a small quantity in flask, carry out rectifying to it, rectification temperature is 130 ~ 140 DEG C, can obtain oxalic acid methyl ether acetate product, and product enters finished pot.
(4) sec-butyl alcohol-2-butyl acetate is separated:
With the step (4) in embodiment one.
(5) analysis of product purity
With the step (5) in embodiment one, after testing, the purity of product ethylene glycol ether acetate is 99.5%, and the purity of sec-butyl alcohol is: 99.1%.
Equivalence explanation
Above high to the clear preparation method's product yield describing ethylene glycol monoalkyl ether acetate of the present invention of specific descriptions of the present invention, speed of response is fast, energy consumption is low, product separation is purified easily, with low cost, technique simple, product utilization rate advantages of higher.Although specific embodiment here describes in detail, this only as the explanation of technical solution problem of the present invention, and does not limit the scope of claims to the claims in the present invention.Particularly point out, inventor is through careful consideration, and the replacement that the present invention is different, change do not depart from the connotation and extension that the claims in the present invention define.
Claims (9)
1. the preparation method of an ethylene glycol monoalkyl ether acetate, it is characterized in that: with sec-butyl acetate and ethylene glycol monoalkyl ether for raw material, under solid base catalyst exist, carry out transesterification reaction be prepared into ethylene glycol monoalkyl ether acetate, specifically comprise the following steps:
1) preliminary transesterification reaction: under 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 DEG C, and the reaction times is 2 ~ 15h;
2) transesterify chemical reaction equilibrium is broken: complete 1) maintain the temperature at 90 ~ 140 DEG C after step, distill out step 1) the middle sec-butyl alcohol generated, detect the amount of the sec-butyl acetate contained in the mixture distilled out in batches, and sec-butyl acetate is added in former reaction system, the amount of substance of the sec-butyl acetate at every turn added is the amount of substance 1 ~ 4 times of the sec-butyl acetate at every turn distilled out, and the time that this step continues is 7 ~ 20h;
3) latter stage transesterification reaction: in step 2) in add sec-butyl acetate for the last time after, maintain 90 ~ 140 DEG C of temperature and proceed transesterification reaction 1 ~ 6h;
4) separating-purifying of glycol product monoalkyl ether acetate: the mixture rectification and purification in reaction vessel is obtained to the ethylene glycol monoalkyl ether acetate needed.
2. the preparation method of ethylene glycol monoalkyl ether acetate according to claim 1, is characterized in that: further comprising the steps of: the separating-purifying of product sec-butyl alcohol: to step 2) in distill out carry out rectification and purification containing the mixture of sec-butyl alcohol and obtain sec-butyl alcohol.
3. the preparation method of ethylene glycol monoalkyl ether acetate according to claim 1, is characterized in that: described ethylene glycol monoalkyl ether is the one in following compounds: ethylene glycol monomethyl ether, ethylene glycol ethyl ether, butyl glycol ether.
4. the preparation method of ethylene glycol monoalkyl ether acetate according to claim 1, is characterized in that: described solid base catalyst is KOH, K
2cO
3, NaOH, Na
2cO
3, CH
3oNa, C
2h
5one or more combination in ONa.
5. the preparation method of ethylene glycol monoalkyl ether acetate according to claim 4, is characterized in that: described solid base catalyst is K
2cO
3.
6. the preparation method of ethylene glycol monoalkyl ether acetate according to claim 1, is characterized in that: the mol ratio of solid base catalyst, ethylene glycol monoalkyl ether, sec-butyl acetate is 0.02: 1: 1.
7. the preparation method of ethylene glycol monoalkyl ether acetate according to claim 1, is characterized in that: the described preliminary transesterification reaction time is 5 ~ 7h, and temperature is 110 ~ 120 DEG C.
8. the preparation method of ethylene glycol monoalkyl ether acetate according to claim 1, it is characterized in that: described in break temperature of reaction in transesterify chemical reaction equilibrium step be 110 ~ 120 DEG C, the amount of substance of the sec-butyl acetate added is the amount of substance 2 times of the sec-butyl acetate distilled out.
9. 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 DEG C.
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| 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 |
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2011
- 2011-12-31 CN CN201110459651.3A patent/CN103183611B/en active Active
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| 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 |
|---|
| 固体碱K2CO3/Al2O3催化酯交换法合成乙二醇甲醚乙酸酯;龚国珍 等;《精细化工》;20081015;第25卷(第10期);第982-984和998页 * |
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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. |
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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. |