JPS60260538A - グリコ−ル酸エステルの製造法 - Google Patents
グリコ−ル酸エステルの製造法Info
- Publication number
- JPS60260538A JPS60260538A JP59117215A JP11721584A JPS60260538A JP S60260538 A JPS60260538 A JP S60260538A JP 59117215 A JP59117215 A JP 59117215A JP 11721584 A JP11721584 A JP 11721584A JP S60260538 A JPS60260538 A JP S60260538A
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- formaldehyde
- reaction
- reaction system
- acid ester
- 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
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Natural products OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 title claims description 12
- -1 glycolic acid ester Chemical class 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical class O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 67
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- 239000003054 catalyst Substances 0.000 claims abstract description 21
- 239000011949 solid catalyst Substances 0.000 claims abstract description 9
- 229920000642 polymer Polymers 0.000 claims abstract description 5
- 239000011347 resin Substances 0.000 claims abstract description 5
- 229920005989 resin Polymers 0.000 claims abstract description 5
- 150000003460 sulfonic acids Chemical class 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 10
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 9
- 229910002090 carbon oxide Inorganic materials 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 10
- 238000006136 alcoholysis reaction Methods 0.000 abstract description 9
- 239000011541 reaction mixture Substances 0.000 abstract description 5
- 238000005260 corrosion Methods 0.000 abstract description 3
- 230000007797 corrosion Effects 0.000 abstract description 3
- 238000001035 drying Methods 0.000 abstract description 3
- 230000008929 regeneration Effects 0.000 abstract description 3
- 238000011069 regeneration method Methods 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 2
- 238000010926 purge Methods 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 235000019256 formaldehyde Nutrition 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- 239000000706 filtrate Substances 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 235000019441 ethanol Nutrition 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 5
- 229910002091 carbon monoxide Inorganic materials 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 3
- DQPDAFDEASYJKB-UHFFFAOYSA-N 2-(2-methoxy-2-oxoethoxy)acetic acid Chemical compound COC(=O)COCC(O)=O DQPDAFDEASYJKB-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 241000860832 Yoda Species 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000013064 chemical raw material Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- VMVNZNXAVJHNDJ-UHFFFAOYSA-N methyl 2,2,2-trifluoroacetate Chemical compound COC(=O)C(F)(F)F VMVNZNXAVJHNDJ-UHFFFAOYSA-N 0.000 description 1
- KUCRTUQUAYLJDC-UHFFFAOYSA-N methyl 2-(2-methoxy-2-oxoethoxy)acetate Chemical compound COC(=O)COCC(=O)OC KUCRTUQUAYLJDC-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000003930 superacid Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59117215A JPS60260538A (ja) | 1984-06-07 | 1984-06-07 | グリコ−ル酸エステルの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59117215A JPS60260538A (ja) | 1984-06-07 | 1984-06-07 | グリコ−ル酸エステルの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60260538A true JPS60260538A (ja) | 1985-12-23 |
| JPH0210140B2 JPH0210140B2 (enrdf_load_stackoverflow) | 1990-03-06 |
Family
ID=14706241
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59117215A Granted JPS60260538A (ja) | 1984-06-07 | 1984-06-07 | グリコ−ル酸エステルの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60260538A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2559641A (en) * | 2016-09-16 | 2018-08-15 | Johnson Matthey Davy Technologies Ltd | Process |
| CN109550507A (zh) * | 2018-12-07 | 2019-04-02 | 徐州伯利恒生物科技有限公司 | 一种乙醇酸丁酯的合成方法 |
| CN109550506A (zh) * | 2018-12-07 | 2019-04-02 | 徐州伯利恒生物科技有限公司 | 一种低腐蚀性催化剂 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51127024A (en) * | 1975-04-23 | 1976-11-05 | Ppg Industries Inc | Method of producing hydroxy carboxylic acid and derivatives |
| JPS5728015A (en) * | 1980-07-28 | 1982-02-15 | Mitsubishi Chem Ind Ltd | Preparation of glycolic acid ether and ester |
-
1984
- 1984-06-07 JP JP59117215A patent/JPS60260538A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51127024A (en) * | 1975-04-23 | 1976-11-05 | Ppg Industries Inc | Method of producing hydroxy carboxylic acid and derivatives |
| JPS5728015A (en) * | 1980-07-28 | 1982-02-15 | Mitsubishi Chem Ind Ltd | Preparation of glycolic acid ether and ester |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2559641A (en) * | 2016-09-16 | 2018-08-15 | Johnson Matthey Davy Technologies Ltd | Process |
| JP2019529422A (ja) * | 2016-09-16 | 2019-10-17 | ジョンソン マッセイ デイヴィー テクノロジーズ リミテッド | グリコール酸を製造するための方法 |
| GB2559641B (en) * | 2016-09-16 | 2019-12-04 | Johnson Matthey Davy Technologies Ltd | Process for the production of glycolic acid |
| US10640443B2 (en) | 2016-09-16 | 2020-05-05 | Johnson Matthey Davy Technologies Limited | Process for the production of glycolic acid |
| US11053186B2 (en) | 2016-09-16 | 2021-07-06 | Johnson Matthey Davy Technologies Limited | Process for the production of glycolic acid |
| CN109550507A (zh) * | 2018-12-07 | 2019-04-02 | 徐州伯利恒生物科技有限公司 | 一种乙醇酸丁酯的合成方法 |
| CN109550506A (zh) * | 2018-12-07 | 2019-04-02 | 徐州伯利恒生物科技有限公司 | 一种低腐蚀性催化剂 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0210140B2 (enrdf_load_stackoverflow) | 1990-03-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |