DE2545658C2 - Verfahren zur Gewinnung von Carbonsäuren aus ihren wäßrigen Lösungen - Google Patents
Verfahren zur Gewinnung von Carbonsäuren aus ihren wäßrigen LösungenInfo
- Publication number
- DE2545658C2 DE2545658C2 DE2545658A DE2545658A DE2545658C2 DE 2545658 C2 DE2545658 C2 DE 2545658C2 DE 2545658 A DE2545658 A DE 2545658A DE 2545658 A DE2545658 A DE 2545658A DE 2545658 C2 DE2545658 C2 DE 2545658C2
- Authority
- DE
- Germany
- Prior art keywords
- acid
- extraction
- aqueous solutions
- water
- general formula
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 11
- 239000007864 aqueous solution Substances 0.000 title claims description 9
- 150000001735 carboxylic acids Chemical class 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 239000002253 acid Substances 0.000 claims description 32
- 238000000605 extraction Methods 0.000 claims description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 24
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 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 11
- 235000019253 formic acid Nutrition 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 238000004821 distillation Methods 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- 235000019260 propionic acid Nutrition 0.000 claims description 3
- 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 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 239000000284 extract Substances 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- 150000003334 secondary amides Chemical class 0.000 claims 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims 1
- 238000005267 amalgamation Methods 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 238000007700 distillative separation Methods 0.000 claims 1
- 229940117955 isoamyl acetate Drugs 0.000 claims 1
- 238000001577 simple distillation Methods 0.000 claims 1
- 239000002689 soil Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 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
- 239000008346 aqueous phase Substances 0.000 description 2
- 230000001427 coherent effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- -1 formic acid Dibutylformamides Chemical class 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- NZMAJUHVSZBJHL-UHFFFAOYSA-N n,n-dibutylformamide Chemical compound CCCCN(C=O)CCCC NZMAJUHVSZBJHL-UHFFFAOYSA-N 0.000 description 2
- BVYKEGCGRUJWKS-UHFFFAOYSA-N n-butyl-n-cyclohexylacetamide Chemical compound CCCCN(C(C)=O)C1CCCCC1 BVYKEGCGRUJWKS-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 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 1
- WGKDJRNKRUOYBM-UHFFFAOYSA-N CCN(C=O)C1CCCCC1.CCN(C=O)C1=CC=CC=C1 Chemical compound CCN(C=O)C1CCCCC1.CCN(C=O)C1=CC=CC=C1 WGKDJRNKRUOYBM-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000001914 calming effect Effects 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 241001233037 catfish Species 0.000 description 1
- 238000001944 continuous distillation Methods 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
- 239000000945 filler Substances 0.000 description 1
- 150000003948 formamides Chemical class 0.000 description 1
- 238000010327 methods by industry Methods 0.000 description 1
- VXXLEXCQCSPKFI-UHFFFAOYSA-N n-butylcyclohexanamine Chemical compound CCCCNC1CCCCC1 VXXLEXCQCSPKFI-UHFFFAOYSA-N 0.000 description 1
- AGVKXDPPPSLISR-UHFFFAOYSA-N n-ethylcyclohexanamine Chemical compound CCNC1CCCCC1 AGVKXDPPPSLISR-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
- BGWFQRDYRSCOCO-UHFFFAOYSA-N n-methylheptan-2-amine Chemical compound CCCCCC(C)NC BGWFQRDYRSCOCO-UHFFFAOYSA-N 0.000 description 1
- PXKCSKRXWAZGFK-UHFFFAOYSA-N n-propylcyclohexanamine Chemical compound CCCNC1CCCCC1 PXKCSKRXWAZGFK-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007056 transamidation reaction Methods 0.000 description 1
- 238000004065 wastewater treatment Methods 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)
Priority Applications (12)
| 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 |
| IT27806/76A IT1068121B (it) | 1975-10-11 | 1976-09-29 | Processo per l ottenimento di acidi carbossilici da loro soluzioni acquose |
| CA262,961A CA1065889A (en) | 1975-10-11 | 1976-10-07 | Isolation of carboxylic acids from their aqueous solutions |
| NLAANVRAGE7611111,A NL188405C (nl) | 1975-10-11 | 1976-10-07 | Werkwijze voor het winnen van carbonzuren uit waterhoudende oplossingen. |
| BR7606734A BR7606734A (pt) | 1975-10-11 | 1976-10-07 | Processo de obtencao de acidos carboxilicos de suas solucoes aquosas |
| GB41693/76A GB1554172A (en) | 1975-10-11 | 1976-10-07 | Isolation of carboxylic acids from their aqueous solutions |
| NO763447A NO148068C (no) | 1975-10-11 | 1976-10-08 | Fremgangsmaate til utvinning av karboksylsyrer fra vandige loesninger derav ved ekstraksjon med sekundaere amider som ekstraksjonsmidler |
| FR7630284A FR2327215A1 (fr) | 1975-10-11 | 1976-10-08 | Procede d'obtention d'acides carboxyliques a partir de leurs solutions aqueuses |
| ES452288A ES452288A1 (es) | 1975-10-11 | 1976-10-09 | Procedimiento para recuperar acidos carboxilicos. |
| BE171402A BE847154A (fr) | 1975-10-11 | 1976-10-11 | Procede d'obtention d'acides carboxyliques a partir de leurs-solutions aqueuses, |
| JP51121368A JPS6016410B2 (ja) | 1975-10-11 | 1976-10-12 | カルボン酸をその水溶液から収得する方法 |
| US05/893,953 US4217460A (en) | 1975-10-11 | 1978-04-06 | Isolation of formic acid from its aqueous solutions |
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 (2)
| Publication Number | Publication Date |
|---|---|
| DE2545658A1 DE2545658A1 (de) | 1977-04-21 |
| DE2545658C2 true DE2545658C2 (de) | 1985-12-19 |
Family
ID=5958936
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2545658A Expired DE2545658C2 (de) | 1975-10-11 | 1975-10-11 | Verfahren zur Gewinnung von Carbonsäuren aus ihren wäßrigen Lösungen |
Country Status (11)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0563831A3 (en) * | 1992-04-03 | 1993-11-18 | Basf Ag | Process for the preparation of formic acid by thermal cracking of quarternary ammonium formates |
Families Citing this family (20)
| 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 |
| 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) |
| BR112012032211A2 (pt) | 2010-06-29 | 2016-11-29 | Basf Se | "processo para obter ácido fórmico". |
| US8901350B2 (en) | 2010-06-29 | 2014-12-02 | Basf Se | Process for the preparation of formic acid |
| WO2013092157A1 (de) | 2011-12-20 | 2013-06-27 | Basf Se | Verfahren zur herstellung von ameisensäure |
| US8835683B2 (en) | 2011-12-20 | 2014-09-16 | Basf Se | Process for preparing formic acid |
| RU2014129625A (ru) | 2011-12-20 | 2016-02-10 | Басф Се | Способ получения муравьиной кислоты |
| US8889905B2 (en) | 2011-12-20 | 2014-11-18 | Basf Se | Process for preparing formic acid |
| US9428438B2 (en) | 2012-11-27 | 2016-08-30 | Basf Se | Process for preparing formic acid |
| WO2014082845A1 (de) | 2012-11-27 | 2014-06-05 | Basf Se | Verfahren zur herstellung von ameisensäure |
| 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 |
| EP4339183A1 (en) | 2021-05-14 | 2024-03-20 | Refine Holdings Co., Ltd. | Method for collecting carboxylic acid |
| JPWO2024106470A1 (enrdf_load_stackoverflow) | 2022-11-16 | 2024-05-23 |
Family Cites Families (1)
| 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 BR BR7606734A patent/BR7606734A/pt unknown
- 1976-10-07 GB GB41693/76A patent/GB1554172A/en not_active Expired
- 1976-10-07 CA CA262,961A patent/CA1065889A/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/xx not_active IP Right Cessation
- 1976-10-12 JP JP51121368A patent/JPS6016410B2/ja not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0563831A3 (en) * | 1992-04-03 | 1993-11-18 | Basf Ag | Process for the preparation of formic acid by thermal cracking of quarternary ammonium formates |
Also Published As
| Publication number | Publication date |
|---|---|
| ES452288A1 (es) | 1978-03-01 |
| FR2327215A1 (fr) | 1977-05-06 |
| BE847154A (fr) | 1977-04-12 |
| CA1065889A (en) | 1979-11-06 |
| JPS5248614A (en) | 1977-04-18 |
| GB1554172A (en) | 1979-10-17 |
| NL188405C (nl) | 1992-06-16 |
| BR7606734A (pt) | 1977-11-16 |
| DE2545658A1 (de) | 1977-04-21 |
| IT1068121B (it) | 1985-03-21 |
| NO763447L (enrdf_load_stackoverflow) | 1977-04-13 |
| FR2327215B1 (enrdf_load_stackoverflow) | 1980-05-09 |
| JPS6016410B2 (ja) | 1985-04-25 |
| NO148068B (no) | 1983-04-25 |
| NL7611111A (nl) | 1977-04-13 |
| NO148068C (no) | 1983-08-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |