CA1105486A - Procede industriel d'obtention d'esters d'acide glycolique - Google Patents

Procede industriel d'obtention d'esters d'acide glycolique

Info

Publication number: CA1105486A
Authority: CA; Canada
Prior art keywords: glycolic acid; acid esters; manufacture; acid ester; formic acid
Prior art date: 1976-11-15
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.): Expired

Application number

CA290,707A

Other languages

English (en)

Inventor

Ernst I. Leupold

Hans-Jurgen Arpe

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Hoechst AG

Original Assignee

Hoechst AG

Priority date (The priority date 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 date listed.)

1976-11-15

Filing date

1977-11-14

Publication date

1981-07-21

1977-11-14 Application filed by Hoechst AG filed Critical Hoechst AG

1981-07-21 Application granted granted Critical

1981-07-21 Publication of CA1105486A publication Critical patent/CA1105486A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 17
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 title claims abstract description 11
238000004519 manufacturing process Methods 0.000 title abstract 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 18
-1 formic acid ester Chemical class 0.000 claims abstract description 13
229930040373 Paraformaldehyde Natural products 0.000 claims abstract description 9
235000019253 formic acid Nutrition 0.000 claims abstract description 8
239000007791 liquid phase Substances 0.000 claims abstract description 7
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 4
239000003377 acid catalyst Substances 0.000 claims abstract description 3
239000000203 mixture Substances 0.000 claims abstract description 3
BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 claims abstract 2
238000006243 chemical reaction Methods 0.000 claims description 9
229920002866 paraformaldehyde Polymers 0.000 claims description 6
239000003054 catalyst Substances 0.000 claims description 5
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract description 10
230000002378 acidificating effect Effects 0.000 abstract description 2
KQBSGRWMSNFIPG-UHFFFAOYSA-N trioxane Chemical compound C1COOOC1 KQBSGRWMSNFIPG-UHFFFAOYSA-N 0.000 description 7
150000002148 esters Chemical class 0.000 description 5
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 3
229910002091 carbon monoxide Inorganic materials 0.000 description 3
235000019256 formaldehyde Nutrition 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
241000905957 Channa melasoma Species 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
229940098779 methanesulfonic acid Drugs 0.000 description 2
GSJFXBNYJCXDGI-UHFFFAOYSA-N methyl 2-hydroxyacetate Chemical compound COC(=O)CO GSJFXBNYJCXDGI-UHFFFAOYSA-N 0.000 description 2
TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
239000000020 Nitrocellulose Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 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
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
238000009835 boiling Methods 0.000 description 1
VFGRALUHHHDIQI-UHFFFAOYSA-N butyl 2-hydroxyacetate Chemical compound CCCCOC(=O)CO VFGRALUHHHDIQI-UHFFFAOYSA-N 0.000 description 1
NMJJFJNHVMGPGM-UHFFFAOYSA-N butyl formate Chemical compound CCCCOC=O NMJJFJNHVMGPGM-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
229920003086 cellulose ether Polymers 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
229920005565 cyclic polymer Polymers 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
BTZNPZMHENLISZ-UHFFFAOYSA-N fluoromethanesulfonic acid Chemical compound OS(=O)(=O)CF BTZNPZMHENLISZ-UHFFFAOYSA-N 0.000 description 1
239000011521 glass Substances 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
229920001220 nitrocellulos Polymers 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000036647 reaction Effects 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000002966 varnish Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA290,707A 1976-11-15 1977-11-14 Procede industriel d'obtention d'esters d'acide glycolique Expired CA1105486A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DEP2652072.9		1976-11-15
DE19762652072 DE2652072A1 (de)	1976-11-15	1976-11-15	Verfahren zur herstellung von glykolsaeureestern

Publications (1)

Publication Number	Publication Date
CA1105486A true CA1105486A (fr)	1981-07-21

Family

ID=5993221

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA290,707A Expired CA1105486A (fr)	1976-11-15	1977-11-14	Procede industriel d'obtention d'esters d'acide glycolique

Country Status (8)

Country	Link
JP (1)	JPS5398924A (fr)
BE (1)	BE860878A (fr)
CA (1)	CA1105486A (fr)
DE (1)	DE2652072A1 (fr)
FR (1)	FR2370716A1 (fr)
GB (1)	GB1595231A (fr)
IT (1)	IT1088881B (fr)
NL (1)	NL7712392A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB201615762D0 (en)	2016-09-16	2016-11-02	Johnson Matthey Davy Technologies Ltd	Process

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5128615B2 (fr) *	1972-10-03	1976-08-20

1976
- 1976-11-15 DE DE19762652072 patent/DE2652072A1/de not_active Withdrawn
1977
- 1977-11-10 NL NL7712392A patent/NL7712392A/xx not_active Application Discontinuation
- 1977-11-11 IT IT2961077A patent/IT1088881B/it active
- 1977-11-14 CA CA290,707A patent/CA1105486A/fr not_active Expired
- 1977-11-14 GB GB4728577A patent/GB1595231A/en not_active Expired
- 1977-11-14 JP JP13580177A patent/JPS5398924A/ja active Pending
- 1977-11-15 FR FR7734232A patent/FR2370716A1/fr active Pending
- 1977-11-16 BE BE182662A patent/BE860878A/fr unknown

Also Published As

Publication number	Publication date
BE860878A (fr)	1978-05-16
GB1595231A (en)	1981-08-12
JPS5398924A (en)	1978-08-29
NL7712392A (nl)	1978-05-17
IT1088881B (it)	1985-06-10
DE2652072A1 (de)	1978-05-24
FR2370716A1 (fr)	1978-06-09

Legal Events

Date	Code	Title	Description
1998-07-21	MKEX	Expiry

Publication	Publication Date	Title
US3911003A (en)	1975-10-07	Process for the production of glycolic acid and oxydiacetic acid
IE43223B1 (en)	1981-01-14	Production of dialkyl carbonate
IE50306B1 (en)	1986-04-02	Process for preparing an alpha-cyanoacrylate
EP0891320A1 (fr)	1999-01-20	Procede de production de 1,2-bis(acyloxylates)
US4128575A (en)	1978-12-05	Process for the manufacture of glycolic acid or its esters
US4144401A (en)	1979-03-13	Alcohol production
CA1105486A (fr)	1981-07-21	Procede industriel d'obtention d'esters d'acide glycolique
US4228305A (en)	1980-10-14	Process for preparing acetic acid derivatives
JPS5929180B2 (ja)	1984-07-18	グリコ−ル酸の製造方法
US4189599A (en)	1980-02-19	Preparation of dimethyl adipate by the hydrogenation of dimethyl hex-3-endioate
US4226780A (en)	1980-10-07	Manufacture of propylene oxide
US5075493A (en)	1991-12-24	Process for preparing α, β-unsaturated carboxylic acid ester
EP0299743B1 (fr)	1991-06-12	Récupération d'acide acrylique et/ou d'acrylate d'éthyle de l'acide noir
JPH0581582B2 (fr)	1993-11-15
US3742049A (en)	1973-06-26	Method for producing bis(4-aminocyclohexyl)alkane
US2766259A (en)	1956-10-09	Acetals of 2-formyl-6-alkoxytetrahydropyrans
Zieger et al.	1962	2-Chloro-3-dimethylamino-6-phenylsulfonylphenyllithium
US3888880A (en)	1975-06-10	Synthesis of diether-aldehydes and diether-alcohols
US2967890A (en)	1961-01-10	Process for preparing beta-aliphaticoxy-
US3707546A (en)	1972-12-26	Process for preparing dodecanedinitrile
JP3145821B2 (ja)	2001-03-12	オクタジエニルエーテルの製造方法及び新規化合物３−エチル−３−〔（２，７−オクタジエニルオキシ）メチル〕−オキセタン
JPH03173846A (ja)	1991-07-29	クロルカルボン酸クロリドの製造方法
JPS6022693B2 (ja)	1985-06-03	メタクリル酸エステルの製法
JPS6133180A (ja)	1986-02-17	エポキシ化合物の製造方法
US3355428A (en)	1967-11-28	Polyoxymethylene process