CN106083578A - A kind of preparation method of ethylene glycol monomethyl ether acetate - Google Patents
A kind of preparation method of ethylene glycol monomethyl ether acetate Download PDFInfo
- Publication number
- CN106083578A CN106083578A CN201610516080.5A CN201610516080A CN106083578A CN 106083578 A CN106083578 A CN 106083578A CN 201610516080 A CN201610516080 A CN 201610516080A CN 106083578 A CN106083578 A CN 106083578A
- Authority
- CN
- China
- Prior art keywords
- ethylene glycol
- preparation
- monomethyl ether
- glycol monomethyl
- ether acetate
- 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
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 30
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- 238000004821 distillation Methods 0.000 claims abstract description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- 235000021050 feed intake Nutrition 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 abstract description 2
- 230000007423 decrease Effects 0.000 abstract description 2
- 238000010438 heat treatment Methods 0.000 abstract description 2
- 239000012535 impurity Substances 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QACZTJJABFVRAS-UHFFFAOYSA-N acetic acid;2-butoxyethanol Chemical compound CC(O)=O.CCCCOCCO QACZTJJABFVRAS-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000004434 industrial solvent Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- -1 printing and dyeing Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses the preparation method of a kind of ethylene glycol monomethyl ether acetate, with ethylene glycol monobutyl ether and acetic acid as raw material, with toluenesulfonic acid as catalyst, normal propyl alcohol as dehydrant, prepare highly purified ethylene glycol monomethyl ether acetate by post bake backflow.The present invention, compared with conventional art, is improve the purity of finished product, decreases impurity content by distillation of repeatedly heating.
Description
Technical field
The invention belongs to chemical industry synthesis field, be specifically related to the preparation method of a kind of ethylene glycol monomethyl ether acetate.
Background technology
Ethylene glycol monomethyl ether acetate is the industrial solvent that a class is important, and this solvent molecule structure is unique, with in a part
Existing nonpolar part, polarized group again, therefore it all has preferable solvability to polarity and apolar substance, it dissolves
Performance is much higher than common solvent.Owing to ethylene glycol monomethyl ether acetate has solvent nature height, Heat stability is good, viscosity
Little, high-foaming and the feature such as corrosivity is little, be widely used in the industry such as coating, detergent, printing and dyeing, pesticide and pluronic polymer.
Summary of the invention
Goal of the invention: present invention aims to the deficiencies in the prior art, it is provided that a kind of ethylene glycol monobutyl ether acetic acid
The preparation method of ester.
Technical scheme: in order to reach foregoing invention purpose, the present invention is specifically achieved in that a kind of ethylene glycol monobutyl ether
The preparation method of acetate, comprises the following steps:
(1) ethylene glycol monobutyl ether and acetic acid are imported reactor by pan feeding valve respectively, be simultaneously introduced catalyst and dehydrant, limit
Border ring feeds；
(2) feed intake end after to reactor heat up, open reactor atmospheric valve, after backflow, control capacity of returns 1200 ~ 1800L/h,
Still temperature is gradually increased to 150 ~ 180 DEG C by 110 DEG C, and still top temperature controls at 80 ~ 100 DEG C, collects backflow；
(3) after step (2) reaction terminates, close pan feeding valve and atmospheric valve, add step (2) backflow from other feeding mouth
Liquid, and reactor is carried out air-distillation to still temperature 170 DEG C；
(4) continue reactor is heated, and open atmospheric valve and reflux, control capacity of returns 1200 ~ 1800 L/h, work as reactor
When interior pH-value is less than 0.02%, stopped reaction, product in still is proceeded to finished product storage tank.
Wherein, in described step (1), the addition mass ratio of ethylene glycol monobutyl ether and acetic acid is 1:0.5 ~ 0.52.
Wherein, the catalyst in described step (1) is p-methyl benzenesulfonic acid, and addition is the 0.10 of ethylene glycol monobutyl ether quality
~0.15%。
Wherein, described dehydrant is normal propyl alcohol, and addition is the 1 ~ 1.5% of ethylene glycol monobutyl ether quality.
Wherein, the addition manner of described catalyst is often to add to add 0.8 ~ 1.2kg after 800kg ethylene glycol monobutyl ether to first
Benzenesulfonic acid.
Wherein, the determination method that described step (2) reaction terminates is: point water yield is ethylene glycol monobutyl ether and acetic acid gross mass
9 ~ 10%, point water speed is less than 2 ~ 4kg/h, and still temperature is more than 150 DEG C.
Beneficial effect: the present invention, compared with conventional art, is improve the purity of finished product, decreases by distillation of repeatedly heating
Impurity content.
Detailed description of the invention
Embodiment 1:
By pan feeding valve, ethylene glycol monobutyl ether and acetic acid being imported reactor respectively, is simultaneously introduced catalyst and dehydrant, limit is anti-
Limit is answered to feed；Feed intake and after terminating, reactor is heated up, open reactor atmospheric valve, after backflow, control capacity of returns 1200 ~ 1800L/
H, still temperature is gradually increased to 150 ~ 180 DEG C by 110 DEG C, and still top temperature controls at 80 ~ 100 DEG C, collects backflow；Treat that above-mentioned reaction is tied
Shu Hou, closes pan feeding valve and atmospheric valve, adds step (2) backflow from other feeding mouth, and reactor is carried out normal pressure steaming
Evaporating to still temperature 170 DEG C, the determination method that reaction terminates is: point water yield is ethylene glycol monobutyl ether and the 9 ~ 10% of acetic acid gross mass, point
Water speed is less than 2 ~ 4kg/h, and still temperature is more than 150 DEG C；Continue reactor is heated, and open atmospheric valve and reflux, control
Capacity of returns 1200 ~ 1800 L/h, when in reactor, pH-value is less than 0.02%, stopped reaction, product in still is proceeded to finished product storage
Tank.
Wherein, the addition mass ratio of described middle ethylene glycol monobutyl ether and acetic acid is 1:0.5 ~ 0.52；Catalyst is to toluene
Sulfonic acid, addition is the 0.10 ~ 0.15% of ethylene glycol monobutyl ether quality, and addition manner is often to add after 800kg ethylene glycol monobutyl ether
Adding 0.8 ~ 1.2kg p-methyl benzenesulfonic acid, dehydrant is normal propyl alcohol, and addition is the 1 ~ 1.5% of ethylene glycol monobutyl ether quality.
Claims (6)
1. the preparation method of an ethylene glycol monomethyl ether acetate, it is characterised in that comprise the following steps:
(1) ethylene glycol monobutyl ether and acetic acid are imported reactor by pan feeding valve respectively, be simultaneously introduced catalyst and dehydrant, limit
Border ring feeds；
(2) feed intake end after to reactor heat up, open reactor atmospheric valve, after backflow, control capacity of returns 1200 ~ 1800L/h,
Still temperature is gradually increased to 150 ~ 180 DEG C by 110 DEG C, and still top temperature controls at 80 ~ 100 DEG C, collects backflow；
(3) after step (2) reaction terminates, close pan feeding valve and atmospheric valve, add step (2) backflow from other feeding mouth
Liquid, and reactor is carried out air-distillation to still temperature 170 DEG C；
(4) continue reactor is heated, and open atmospheric valve and reflux, control capacity of returns 1200 ~ 1800 L/h, work as reactor
When interior pH-value is less than 0.02%, stopped reaction, product in still is proceeded to finished product storage tank.
The preparation method of ethylene glycol monomethyl ether acetate the most according to claim 1, it is characterised in that described step (1)
The addition mass ratio of middle ethylene glycol monobutyl ether and acetic acid is 1:0.5 ~ 0.52.
The preparation method of ethylene glycol monomethyl ether acetate the most according to claim 1, it is characterised in that described step (1)
In catalyst be p-methyl benzenesulfonic acid, addition is the 0.10 ~ 0.15% of ethylene glycol monobutyl ether quality.
The preparation method of ethylene glycol monomethyl ether acetate the most according to claim 1, it is characterised in that described dehydrant is
Normal propyl alcohol, addition is the 1 ~ 1.5% of ethylene glycol monobutyl ether quality.
The preparation method of ethylene glycol monomethyl ether acetate the most according to claim 1, it is characterised in that described catalyst
Addition manner is often to add addition 0.8 ~ 1.2kg p-methyl benzenesulfonic acid after 800kg ethylene glycol monobutyl ether.
The preparation method of ethylene glycol monomethyl ether acetate the most according to claim 1, it is characterised in that described step (2)
The determination method that reaction terminates is: point water yield is ethylene glycol monobutyl ether and the 9 ~ 10% of acetic acid gross mass, point water speed is less than 2 ~
4kg/h, still temperature is more than 150 DEG C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610516080.5A CN106083578B (en) | 2016-07-04 | 2016-07-04 | A kind of preparation method of ethylene glycol monomethyl ether acetate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610516080.5A CN106083578B (en) | 2016-07-04 | 2016-07-04 | A kind of preparation method of ethylene glycol monomethyl ether acetate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106083578A true CN106083578A (en) | 2016-11-09 |
| CN106083578B CN106083578B (en) | 2019-01-22 |
Family
ID=57211839
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610516080.5A Expired - Fee Related CN106083578B (en) | 2016-07-04 | 2016-07-04 | A kind of preparation method of ethylene glycol monomethyl ether acetate |
Country Status (1)
| Country | Link |
|---|---|
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5659073A (en) * | 1995-07-07 | 1997-08-19 | Qi; Jian Steven | Process for making glycol ether acetates |
| CN1515537A (en) * | 2003-08-29 | 2004-07-28 | 江阴市怡达化工有限公司 | Synthesis method of propylene glyco lmethyl ether acetate |
| CN101337884A (en) * | 2008-08-08 | 2009-01-07 | 德纳（南京）化工有限公司 | Method for preparing 2-Butoxyethyl acetate by continuous esterification reaction |
| CN101475478A (en) * | 2009-01-20 | 2009-07-08 | 江苏怡达化工有限公司 | Method for synthesizing ethylene glycol monobutyl ether acetate |
-
2016
- 2016-07-04 CN CN201610516080.5A patent/CN106083578B/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5659073A (en) * | 1995-07-07 | 1997-08-19 | Qi; Jian Steven | Process for making glycol ether acetates |
| CN1515537A (en) * | 2003-08-29 | 2004-07-28 | 江阴市怡达化工有限公司 | Synthesis method of propylene glyco lmethyl ether acetate |
| CN101337884A (en) * | 2008-08-08 | 2009-01-07 | 德纳（南京）化工有限公司 | Method for preparing 2-Butoxyethyl acetate by continuous esterification reaction |
| CN101475478A (en) * | 2009-01-20 | 2009-07-08 | 江苏怡达化工有限公司 | Method for synthesizing ethylene glycol monobutyl ether acetate |
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| Publication number | Publication date |
|---|---|
| CN106083578B (en) | 2019-01-22 |
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Granted publication date: 20190122 |