CA1151207A - Esterification d'acides carboxyliques par des alcools - Google Patents

Esterification d'acides carboxyliques par des alcools

Info

Publication number: CA1151207A
Authority: CA; Canada
Prior art keywords: acid; alcohol; ether; carboxylic acid; glycol
Prior art date: 1979-11-13
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

CA000364628A

Other languages

English (en)

Inventor

David J. Schreck

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.)

Union Carbide Corp

Original Assignee

Union Carbide Corp

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.)

1979-11-13

Filing date

1980-11-13

Publication date

1983-08-02

1980-11-13 Application filed by Union Carbide Corp filed Critical Union Carbide Corp

1983-08-02 Application granted granted Critical

1983-08-02 Publication of CA1151207A publication Critical patent/CA1151207A/fr

Status Expired legal-status Critical Current

Links

150000001735 carboxylic acids Chemical class 0.000 title claims abstract description 9
238000005886 esterification reaction Methods 0.000 title abstract description 10
230000032050 esterification Effects 0.000 title abstract description 9
150000001298 alcohols Chemical class 0.000 title abstract description 3
229920005989 resin Polymers 0.000 claims abstract description 11
239000011347 resin Substances 0.000 claims abstract description 11
UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 claims abstract description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
238000000034 method Methods 0.000 claims description 17
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
150000002148 esters Chemical class 0.000 claims description 10
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 8
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 4
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 2
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 2
230000003197 catalytic effect Effects 0.000 claims description 2
229920001577 copolymer Polymers 0.000 claims description 2
OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 claims description 2
BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 2
150000001346 alkyl aryl ethers Chemical class 0.000 claims 4
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims 1
239000003054 catalyst Substances 0.000 description 22
239000002253 acid Substances 0.000 description 13
229920000557 Nafion® Polymers 0.000 description 12
239000000047 product Substances 0.000 description 8
235000019441 ethanol Nutrition 0.000 description 7
229920001429 chelating resin Polymers 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 5
230000035484 reaction time Effects 0.000 description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
-1 hydrocarbon acids Chemical class 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
239000003377 acid catalyst Substances 0.000 description 3
WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
239000003456 ion exchange resin Substances 0.000 description 2
229920003303 ion-exchange polymer Polymers 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000009834 vaporization Methods 0.000 description 2
230000008016 vaporization Effects 0.000 description 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 1
PLLBRTOLHQQAQQ-UHFFFAOYSA-N 8-methylnonan-1-ol Chemical compound CC(C)CCCCCCCO PLLBRTOLHQQAQQ-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
159000000032 aromatic acids Chemical class 0.000 description 1
238000010923 batch production Methods 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
150000007520 diprotic acids Chemical class 0.000 description 1
238000004821 distillation Methods 0.000 description 1
229940093476 ethylene glycol Drugs 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
239000003205 fragrance Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000010297 mechanical methods and process Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000000203 mixture Substances 0.000 description 1
239000000178 monomer Substances 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
239000002699 waste material Substances 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

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)

CA000364628A 1979-11-13 1980-11-13 Esterification d'acides carboxyliques par des alcools Expired CA1151207A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US9358579A	1979-11-13	1979-11-13
US093,585		1979-11-13

Publications (1)

Publication Number	Publication Date
CA1151207A true CA1151207A (fr)	1983-08-02

Family

ID=22239737

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000364628A Expired CA1151207A (fr)	1979-11-13	1980-11-13	Esterification d'acides carboxyliques par des alcools

Country Status (4)

Country	Link
JP (1)	JPS5679637A (fr)
CA (1)	CA1151207A (fr)
DE (1)	DE3042695A1 (fr)
GB (1)	GB2063261B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8408801D0 (en) *	1984-04-05	1984-05-16	Bp Chem Int Ltd	Process for making esters
CN1332924C (zh) *	2005-04-07	2007-08-22	浙江工业大学	一种有机酸酯化方法

1980
- 1980-11-12 JP JP15832980A patent/JPS5679637A/ja active Granted
- 1980-11-12 GB GB8036221A patent/GB2063261B/en not_active Expired
- 1980-11-12 DE DE19803042695 patent/DE3042695A1/de not_active Ceased
- 1980-11-13 CA CA000364628A patent/CA1151207A/fr not_active Expired

Also Published As

Publication number	Publication date
JPS5679637A (en)	1981-06-30
GB2063261B (en)	1984-02-01
DE3042695A1 (de)	1981-05-27
GB2063261A (en)	1981-06-03
JPS6121543B2 (fr)	1986-05-27

Legal Events

Date	Code	Title	Description
2000-08-02	MKEX	Expiry

Publication	Publication Date	Title
EP0552541B1 (fr)	1995-11-02	Procédé d'estérification catalysé
EP0005680B1 (fr)	1982-05-12	Procédé de préparation de l'acétate d'éthyle
US5231222A (en)	1993-07-27	Esterification process
US4283572A (en)	1981-08-11	Conversion of alkyl phenyl ether to alkylphenol
CN1089753C (zh)	2002-08-28	氧化叔胺的制备方法
EP0461975B1 (fr)	1995-02-15	La préparation d'esters d'acides carboxyliques insaturés par (trans)estérification en phase liquide en utilisant des hétéropolyacides comme catalyseurs
US3989740A (en)	1976-11-02	Method of preparing polyalkylene glycol acrylates
KR0174109B1 (ko)	1999-04-01	비아세틸-비함유 메틸 메트아크릴레이트의 제조방법
CA1284655C (fr)	1991-06-04	Procede catalytique pour la production d'esters alkoxyles
EP0119833B1 (fr)	1988-11-17	Préparation d'esters d'acides carboxyliques d'éthers monoalkyliques d'alkylène glycole
US6444842B1 (en)	2002-09-03	Continuous process for the production of carboxylic acid esters of alkylene glycol monoalkyl ethers
US4228305A (en)	1980-10-14	Process for preparing acetic acid derivatives
EP0210907B1 (fr)	1989-09-13	Procédé de préparation d'esters méthacryliques par transestérification
JPH06219991A (ja)	1994-08-09	多官能性（メタ）アクリレートの製造方法
US4458088A (en)	1984-07-03	Continuous process for the extraction and esterification of carboxylic acid
JPS637571B2 (fr)	1988-02-17
JPS58183641A (ja)	1983-10-26	（メタ）アクリル酸メチルの精製法
AU9116891A (en)	1992-06-25	Azeotropic assisted transvinylation technology
JP3986756B2 (ja)	2007-10-03	アルキレングリコールモノアルキルエーテルのカルボン酸エステルを製造するための連続法
GB2063261A (en)	1981-06-03	Esterification of Carboxylic Acids with Alcohols
US3932531A (en)	1976-01-13	Method of manufacturing alkylene oxide adducts of an aliphatic alcohol
EP0989969B1 (fr)	2002-04-10	Procede de production d'acides carboxyliques
JP2686824B2 (ja)	1997-12-08	ジペンタエリスリトールヘキサエステル化合物の製法
EP0385882B1 (fr)	1992-11-19	Procédé d'hydroxylation de phénols et d'éthers de phénols
JP3953133B2 (ja)	2007-08-08	α−ヒドロキシアルキルアクリル酸類の安定化方法