CA1065889A - Extraction des acides carboxyliques en presence dans des solutions aqueuses - Google Patents

Extraction des acides carboxyliques en presence dans des solutions aqueuses

Info

Publication number: CA1065889A
Authority: CA; Canada
Prior art keywords: acid; extractant; aqueous solutions; carboxylic acids; radicals
Prior art date: 1975-10-11
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

CA262,961A

Other languages

English (en)

Inventor

Heinz Hohenschutz

Johannes E. Schmidt

Hans Kiefer

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.)

BASF SE

Original Assignee

BASF SE

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.)

1975-10-11

Filing date

1976-10-07

Publication date

1979-11-06

1976-10-07 Application filed by BASF SE filed Critical BASF SE

1979-11-06 Application granted granted Critical

1979-11-06 Publication of CA1065889A publication Critical patent/CA1065889A/fr

Status Expired legal-status Critical Current

Links

239000007864 aqueous solution Substances 0.000 title claims abstract description 10
150000001735 carboxylic acids Chemical class 0.000 title abstract description 7
238000002955 isolation Methods 0.000 title description 5
239000000203 mixture Substances 0.000 claims abstract description 10
125000003118 aryl group Chemical group 0.000 claims abstract description 6
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 4
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
239000001257 hydrogen Substances 0.000 claims abstract description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 4
229920002554 vinyl polymer Chemical group 0.000 claims abstract description 4
125000000217 alkyl group Chemical group 0.000 claims abstract description 3
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
239000002253 acid Substances 0.000 claims description 34
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 27
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 18
238000000034 method Methods 0.000 claims description 13
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 9
235000019253 formic acid Nutrition 0.000 claims description 9
BVYKEGCGRUJWKS-UHFFFAOYSA-N n-butyl-n-cyclohexylacetamide Chemical compound CCCCN(C(C)=O)C1CCCCC1 BVYKEGCGRUJWKS-UHFFFAOYSA-N 0.000 claims description 3
-1 N-n-butyl-2-ethylhexylacetamide Chemical compound 0.000 claims description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
NZMAJUHVSZBJHL-UHFFFAOYSA-N n,n-dibutylformamide Chemical compound CCCCN(C=O)CCCC NZMAJUHVSZBJHL-UHFFFAOYSA-N 0.000 claims description 2
125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
238000000605 extraction Methods 0.000 abstract description 12
238000004821 distillation Methods 0.000 abstract description 5
150000003334 secondary amides Chemical class 0.000 abstract description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
238000005192 partition Methods 0.000 description 6
239000012071 phase Substances 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
239000000243 solution Substances 0.000 description 4
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
UZADBXPHDWZTHP-UHFFFAOYSA-N n-butyl-n-ethyloctanamide Chemical compound CCCCCCCC(=O)N(CC)CCCC UZADBXPHDWZTHP-UHFFFAOYSA-N 0.000 description 3
238000000926 separation method Methods 0.000 description 3
SPPWGCYEYAMHDT-UHFFFAOYSA-N 1,4-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=C(C(C)C)C=C1 SPPWGCYEYAMHDT-UHFFFAOYSA-N 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000011067 equilibration Methods 0.000 description 2
MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
235000019260 propionic acid Nutrition 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000007056 transamidation reaction Methods 0.000 description 2
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
VUXKVKAHWOVIDN-UHFFFAOYSA-N Cyclohexyl formate Chemical compound O=COC1CCCCC1 VUXKVKAHWOVIDN-UHFFFAOYSA-N 0.000 description 1
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
241000448280 Elates Species 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
229910002091 carbon monoxide Inorganic materials 0.000 description 1
238000001944 continuous distillation Methods 0.000 description 1
230000000875 corresponding effect Effects 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
238000000895 extractive distillation Methods 0.000 description 1
150000003948 formamides Chemical class 0.000 description 1
238000005755 formation reaction Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
229940117955 isoamyl acetate Drugs 0.000 description 1
FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
VXXLEXCQCSPKFI-UHFFFAOYSA-N n-butylcyclohexanamine Chemical compound CCCCNC1CCCCC1 VXXLEXCQCSPKFI-UHFFFAOYSA-N 0.000 description 1
BNTVUXYRPWLPFG-UHFFFAOYSA-N n-cyclohexyl-n-ethylformamide Chemical compound CCN(C=O)C1CCCCC1 BNTVUXYRPWLPFG-UHFFFAOYSA-N 0.000 description 1
GBDYFPAHVXJQEP-UHFFFAOYSA-N n-ethyl-n-phenylformamide Chemical compound CCN(C=O)C1=CC=CC=C1 GBDYFPAHVXJQEP-UHFFFAOYSA-N 0.000 description 1
AGVKXDPPPSLISR-UHFFFAOYSA-N n-ethylcyclohexanamine Chemical compound CCNC1CCCCC1 AGVKXDPPPSLISR-UHFFFAOYSA-N 0.000 description 1
WSTNFGAKGUERTC-UHFFFAOYSA-N n-ethylhexan-1-amine Chemical compound CCCCCCNCC WSTNFGAKGUERTC-UHFFFAOYSA-N 0.000 description 1
LYELEANKTIGQME-UHFFFAOYSA-N n-heptan-2-yl-n-methylformamide Chemical compound CCCCCC(C)N(C)C=O LYELEANKTIGQME-UHFFFAOYSA-N 0.000 description 1
RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
238000012856 packing Methods 0.000 description 1
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
229940080818 propionamide Drugs 0.000 description 1
238000000746 purification Methods 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000001577 simple distillation Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
VSRBKQFNFZQRBM-UHFFFAOYSA-N tuaminoheptane Chemical compound CCCCCC(C)N VSRBKQFNFZQRBM-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Extraction Or Liquid Replacement (AREA)

CA262,961A 1975-10-11 1976-10-07 Extraction des acides carboxyliques en presence dans des solutions aqueuses Expired CA1065889A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2545658A DE2545658C2 (de)	1975-10-11	1975-10-11	Verfahren zur Gewinnung von Carbonsäuren aus ihren wäßrigen Lösungen

Publications (1)

Publication Number	Publication Date
CA1065889A true CA1065889A (fr)	1979-11-06

Family

ID=5958936

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA262,961A Expired CA1065889A (fr)	1975-10-11	1976-10-07	Extraction des acides carboxyliques en presence dans des solutions aqueuses

Country Status (11)

Country	Link
JP (1)	JPS6016410B2 (fr)
BE (1)	BE847154A (fr)
BR (1)	BR7606734A (fr)
CA (1)	CA1065889A (fr)
DE (1)	DE2545658C2 (fr)
ES (1)	ES452288A1 (fr)
FR (1)	FR2327215A1 (fr)
GB (1)	GB1554172A (fr)
IT (1)	IT1068121B (fr)
NL (1)	NL188405C (fr)
NO (1)	NO148068C (fr)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2853991A1 (de) *	1978-12-14	1980-07-03	Basf Ag	Verfahren zur gewinnung von wasserfreier oder weitgehend wasserfreier ameisensaeure
DE2914671A1 (de) *	1979-04-11	1980-10-23	Basf Ag	Verfahren zur gewinnung von wasserfreier oder weitgehend wasserfreier ameisensaeure
NL8103517A (nl) *	1981-07-24	1983-02-16	Badger Bv	Werkwijze voor het scheiden van carbonzuren van mengsels met niet-zuren door een absorptie-stripbehandeling.
DE3411384A1 (de) *	1984-03-28	1985-10-10	Basf Ag, 6700 Ludwigshafen	Verfahren zur gewinnung von wasserfreier oder weitgehend wasserfreier ameisensaeure durch hydrolyse von methylformiat
DE3417790A1 (de) *	1984-05-14	1985-11-14	Basf Ag, 6700 Ludwigshafen	Verfahren zur herstellung von ameisensaeure
DE4023353A1 (de) *	1990-07-23	1992-01-30	Basf Ag	Verfahren zur gewinnung von carbonsaeuren aus ihren waessrigen loesungen
DE4211141A1 (de) *	1992-04-03	1993-10-07	Basf Ag	Verfahren zur Herstellung von Ameisensäure durch thermische Spaltung von quartären Ammoniumformiaten
US5728872A (en) *	1994-06-27	1998-03-17	Lutz Riemenschneider	Stabilized acrylic acid compositions
DE10002793A1 (de) *	2000-01-24	2001-07-26	Basf Ag	Verwendung eines Extraktionsmittels bei der Herstellung von wasserfreier Ameisensäure
DE102008053315A1 (de)	2008-10-27	2010-04-29	Kiefer, Hans, Dr.	Verbessertes Verfahren zur Herstellung von Tetrahydrofuran (THF)
US8901350B2 (en)	2010-06-29	2014-12-02	Basf Se	Process for the preparation of formic acid
SG186264A1 (en)	2010-06-29	2013-01-30	Basf Se	Method for producing formic acid
CA2856959A1 (fr)	2011-12-20	2013-06-27	Basf Se	Procede de preparation d'acide formique
US8889905B2 (en)	2011-12-20	2014-11-18	Basf Se	Process for preparing formic acid
US8835683B2 (en)	2011-12-20	2014-09-16	Basf Se	Process for preparing formic acid
EP2794540A1 (fr)	2011-12-20	2014-10-29	Basf Se	Procédé de production d'acide formique
CN104812731A (zh)	2012-11-27	2015-07-29	巴斯夫欧洲公司	生产甲酸的方法
US9428438B2 (en)	2012-11-27	2016-08-30	Basf Se	Process for preparing formic acid
CN109053421A (zh) *	2018-09-18	2018-12-21	福建师范大学福清分校	一种萃取-分隔壁精馏处理羧酸纤维素中混合酸废水的设备及方法
EP4339183B8 (fr)	2021-05-14	2026-05-20	Crane Inc.	Procédé de collecte d'acide carboxylique
EP4624642A1 (fr)	2022-11-16	2025-10-01	Spiber Inc.	Procédé de production d'un corps façonné contenant une protéine et procédé de récupération d'acide carboxylique

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2408011A1 (de) *	1974-02-20	1975-09-04	Hoechst Ag	Verfahren zur gewinnung von technisch reiner essigsaeure durch extraktivdestillation

1975
- 1975-10-11 DE DE2545658A patent/DE2545658C2/de not_active Expired
1976
- 1976-09-29 IT IT27806/76A patent/IT1068121B/it active
- 1976-10-07 CA CA262,961A patent/CA1065889A/fr not_active Expired
- 1976-10-07 BR BR7606734A patent/BR7606734A/pt unknown
- 1976-10-07 GB GB41693/76A patent/GB1554172A/en not_active Expired
- 1976-10-07 NL NLAANVRAGE7611111,A patent/NL188405C/xx not_active IP Right Cessation
- 1976-10-08 NO NO763447A patent/NO148068C/no unknown
- 1976-10-08 FR FR7630284A patent/FR2327215A1/fr active Granted
- 1976-10-09 ES ES452288A patent/ES452288A1/es not_active Expired
- 1976-10-11 BE BE171402A patent/BE847154A/fr not_active IP Right Cessation
- 1976-10-12 JP JP51121368A patent/JPS6016410B2/ja not_active Expired

Also Published As

Publication number	Publication date
NO148068C (no)	1983-08-03
NL7611111A (nl)	1977-04-13
FR2327215B1 (fr)	1980-05-09
DE2545658C2 (de)	1985-12-19
NO148068B (no)	1983-04-25
GB1554172A (en)	1979-10-17
ES452288A1 (es)	1978-03-01
NL188405C (nl)	1992-06-16
DE2545658A1 (de)	1977-04-21
BE847154A (fr)	1977-04-12
BR7606734A (pt)	1977-11-16
IT1068121B (it)	1985-03-21
JPS6016410B2 (ja)	1985-04-25
JPS5248614A (en)	1977-04-18
FR2327215A1 (fr)	1977-05-06
NO763447L (fr)	1977-04-13

Publication	Publication Date	Title
US4217460A (en)	1980-08-12	Isolation of formic acid from its aqueous solutions
US4349416A (en)	1982-09-14	Process and device for the separation of mixtures which form an azeotrope
US3433831A (en)	1969-03-18	Separation and purification of acrylic acid from acetic acid by solvent extraction and azeotropic distillation with a two component solvent-entrainer system
US4353784A (en)	1982-10-12	Method of recovery of acetic acid
US4040913A (en)	1977-08-09	Recovery of methacrylic acid from the effluent obtained from the condensation of formaldehyde and propionic acid
US4076594A (en)	1978-02-28	Purification of formic acid by extractive distillation
JPS6016410B2 (ja)	1985-04-25	カルボン酸をその水溶液から収得する方法
US4016049A (en)	1977-04-05	Separation of phenol-cyclohexanone azeotrope by extractive distillation with adipic acid diester
NO327831B1 (no)	2009-10-05	Behandling av avlopsvann i en fremgangsmate for fremstilling av vannfri maursyre
CA1238919A (fr)	1988-07-05	Obtention d'acide formique anhydre, ou en grande partie anhydre, par hydrolyse du formiate de methyle
CA1211736A (fr)	1986-09-23	Recuperation de l'acide formique par distillation
GB824595A (en)	1959-12-02	Improved method and means for purifying phenol
US5338411A (en)	1994-08-16	Separation of ethanol from isopropanol by azeotropic distillation
US5358608A (en)	1994-10-25	Separation of 1-propanol from 2-butanol by extractive distillation
US4308112A (en)	1981-12-29	Process for the isolation of pyrocatechol and hydroquinone
US3878058A (en)	1975-04-15	Recovery of alkylvinylether by extractive distillation of a feed containing only trace amounts of water
US5189216A (en)	1993-02-23	Isolation of a carboxylic acid from an aqueous solution thereof
US3391063A (en)	1968-07-02	Plural distillation for purifying propylene oxide contaminated with methyl formate
US5360520A (en)	1994-11-01	Separation of 2-butanol from t-amyl alcohol by extractive distillation
US3478093A (en)	1969-11-11	Separation of methacrylic acid and acrylic acid
JP2924563B2 (ja)	1999-07-26	酢酸エチルの精製方法
GB1038070A (en)	1966-08-03	Process for separating acrylonitrile and hydrocyanic acid from mixtures by distillation
US4718988A (en)	1988-01-12	Separation of 2-butyl acetate from 2-butanol by extractive distillation
US5380405A (en)	1995-01-10	Separation of alpha-phellandrene from 3-carene by azeotropic distillation
US4482433A (en)	1984-11-13	Purification