CN1031260C - 羧酸的制备方法 - Google Patents

羧酸的制备方法 Download PDF

Info

Publication number: CN1031260C
Authority: CN; China
Prior art keywords: iodide; alkyl; catalyst; carboxylic acid; hydrogen
Prior art date: 1990-05-07
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 - Fee Related

Application number

CN90102635.2A

Other languages

English (en)

Chinese (zh)

Other versions

CN1056300A (zh

Inventor

罗伯特·乔治·比弗

戴维·杰弗里·古利弗

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.)

BP Chemicals Ltd

Original Assignee

BP Chemicals Ltd

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.)

1990-05-07

Filing date

1990-05-07

Publication date

1996-03-13

1990-05-07 Application filed by BP Chemicals Ltd filed Critical BP Chemicals Ltd

1990-05-07 Priority to CN90102635.2A priority Critical patent/CN1031260C/zh

1990-06-19 Priority to DD90341824A priority patent/DD295336A5/de

1991-11-20 Publication of CN1056300A publication Critical patent/CN1056300A/zh

1996-03-13 Application granted granted Critical

1996-03-13 Publication of CN1031260C publication Critical patent/CN1031260C/zh

2005-05-07 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title description 3
150000001735 carboxylic acids Chemical class 0.000 title 1
239000003054 catalyst Substances 0.000 claims abstract description 54
239000010948 rhodium Substances 0.000 claims abstract description 43
238000000034 method Methods 0.000 claims abstract description 38
229910052703 rhodium Inorganic materials 0.000 claims abstract description 36
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims abstract description 35
238000005810 carbonylation reaction Methods 0.000 claims abstract description 31
239000003381 stabilizer Substances 0.000 claims abstract description 29
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 26
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
150000001412 amines Chemical class 0.000 claims abstract description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
238000005956 quaternization reaction Methods 0.000 claims abstract description 4
230000006315 carbonylation Effects 0.000 claims description 28
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 14
229910002091 carbon monoxide Inorganic materials 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 14
125000001453 quaternary ammonium group Chemical group 0.000 claims description 13
229940107816 ammonium iodide Drugs 0.000 claims description 12
229910052799 carbon Inorganic materials 0.000 claims description 12
150000004694 iodide salts Chemical class 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 9
150000002148 esters Chemical class 0.000 claims description 7
XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims description 7
239000012429 reaction media Substances 0.000 claims description 6
239000007788 liquid Substances 0.000 claims description 5
125000002091 cationic group Chemical group 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
150000002500 ions Chemical class 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
229920005862 polyol Polymers 0.000 claims 1
150000003077 polyols Chemical class 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 36
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 12
NURQLCJSMXZBPC-UHFFFAOYSA-N 3,4-dimethylpyridine Chemical compound CC1=CC=NC=C1C NURQLCJSMXZBPC-UHFFFAOYSA-N 0.000 abstract description 5
XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 abstract description 5
YSHMQTRICHYLGF-UHFFFAOYSA-N 4-tert-butylpyridine Chemical compound CC(C)(C)C1=CC=NC=C1 YSHMQTRICHYLGF-UHFFFAOYSA-N 0.000 abstract description 4
239000002253 acid Substances 0.000 abstract description 4
238000006555 catalytic reaction Methods 0.000 abstract description 4
ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 abstract description 2
239000007791 liquid phase Substances 0.000 abstract description 2
FHUHWCJWXNYAMP-UHFFFAOYSA-N 1H-pyridin-2-one hydroiodide Chemical class N1C(C=CC=C1)=O.I FHUHWCJWXNYAMP-UHFFFAOYSA-N 0.000 abstract 1
JBOIAZWJIACNJF-UHFFFAOYSA-N 1h-imidazole;hydroiodide Chemical class [I-].[NH2+]1C=CN=C1 JBOIAZWJIACNJF-UHFFFAOYSA-N 0.000 abstract 1
VJXRKZJMGVSXPX-UHFFFAOYSA-N 4-ethylpyridine Chemical compound CCC1=CC=NC=C1 VJXRKZJMGVSXPX-UHFFFAOYSA-N 0.000 abstract 1
125000000217 alkyl group Chemical group 0.000 abstract 1
150000001875 compounds Chemical class 0.000 abstract 1
BJDYCCHRZIFCGN-UHFFFAOYSA-N pyridin-1-ium;iodide Chemical class I.C1=CC=NC=C1 BJDYCCHRZIFCGN-UHFFFAOYSA-N 0.000 abstract 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 9
239000000203 mixture Substances 0.000 description 9
-1 rhodium (III) compound Chemical class 0.000 description 9
238000001556 precipitation Methods 0.000 description 8
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 7
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 6
HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 6
238000002360 preparation method Methods 0.000 description 5
238000012360 testing method Methods 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 4
239000000047 product Substances 0.000 description 4
238000002474 experimental method Methods 0.000 description 3
150000002460 imidazoles Chemical class 0.000 description 3
MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 2
ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
230000000996 additive effect Effects 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
229910001511 metal iodide Inorganic materials 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 2
PZSJYEAHAINDJI-UHFFFAOYSA-N rhodium(3+) Chemical compound [Rh+3] PZSJYEAHAINDJI-UHFFFAOYSA-N 0.000 description 2
238000005070 sampling Methods 0.000 description 2
MDICIVRGHCTEQJ-UHFFFAOYSA-N 1-methyl-1,2-dihydropyridin-1-ium iodide Chemical compound [I-].C[NH+]1CC=CC=C1 MDICIVRGHCTEQJ-UHFFFAOYSA-N 0.000 description 1
RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-Lutidine Substances CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 1
VFLYBWGSQGMWHP-UHFFFAOYSA-N 3-methyl-1h-imidazol-3-ium;iodide Chemical compound [I-].C[N+]=1C=CNC=1 VFLYBWGSQGMWHP-UHFFFAOYSA-N 0.000 description 1
GCNTZFIIOFTKIY-UHFFFAOYSA-N 4-hydroxypyridine Chemical compound OC1=CC=NC=C1 GCNTZFIIOFTKIY-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
235000008733 Citrus aurantifolia Nutrition 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
235000011941 Tilia x europaea Nutrition 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
150000001339 alkali metal compounds Chemical class 0.000 description 1
229910001619 alkaline earth metal iodide Inorganic materials 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
229910052787 antimony Inorganic materials 0.000 description 1
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
229910052728 basic metal Inorganic materials 0.000 description 1
150000003818 basic metals Chemical group 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
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000007809 chemical reaction catalyst Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
229910052732 germanium Inorganic materials 0.000 description 1
GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000012535 impurity Substances 0.000 description 1
229940006461 iodide ion Drugs 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
239000004571 lime Substances 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
230000033116 oxidation-reduction process Effects 0.000 description 1
235000020004 porter Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003222 pyridines Chemical class 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
239000002994 raw material Substances 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
150000003284 rhodium compounds Chemical class 0.000 description 1
KXAHUXSHRWNTOD-UHFFFAOYSA-K rhodium(3+);triiodide Chemical compound [Rh+3].[I-].[I-].[I-] KXAHUXSHRWNTOD-UHFFFAOYSA-K 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000000926 separation method Methods 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
238000012546 transfer Methods 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CN90102635.2A 1990-05-07 1990-05-07 羧酸的制备方法 Expired - Fee Related CN1031260C (zh)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
CN90102635.2A CN1031260C (zh)	1990-05-07	1990-05-07	羧酸的制备方法
DD90341824A DD295336A5 (de)	1990-05-07	1990-06-19	Verfahren zur herstellung von carbonsaeuren

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CN90102635.2A CN1031260C (zh)	1990-05-07	1990-05-07	羧酸的制备方法
DD90341824A DD295336A5 (de)	1990-05-07	1990-06-19	Verfahren zur herstellung von carbonsaeuren

Publications (2)

Publication Number	Publication Date
CN1056300A CN1056300A (zh)	1991-11-20
CN1031260C true CN1031260C (zh)	1996-03-13

Family

ID=36763176

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CN90102635.2A Expired - Fee Related CN1031260C (zh)	1990-05-07	1990-05-07	羧酸的制备方法

Country Status (2)

Country	Link
CN (1)	CN1031260C (de)
DD (1)	DD295336A5 (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN100484912C (zh) *	2002-01-18	2009-05-06	中国石油化学工业开发股份有限公司	一种制备羧酸的方法
CN100393689C (zh) *	2005-09-06	2008-06-11	西南化工研究设计院	一种甲醇低压羰基合成醋酸的方法
CN101781247B (zh) *	2009-06-26	2013-01-02	上海海事大学	一种合成取代的3-喹啉羧酸及类似物的方法

1990
- 1990-05-07 CN CN90102635.2A patent/CN1031260C/zh not_active Expired - Fee Related
- 1990-06-19 DD DD90341824A patent/DD295336A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
DD295336A5 (de)	1991-10-31
CN1056300A (zh)	1991-11-20

Legal Events

Date	Code	Title
1991-11-20	C06	Publication
1991-11-20	PB01	Publication
1993-08-18	C10	Entry into substantive examination
1993-08-18	SE01	Entry into force of request for substantive examination
1996-03-13	C14	Grant of patent or utility model
1996-03-13	GR01	Patent grant
2002-04-24	C15	Extension of patent right duration from 15 to 20 years for appl. with date before 31.12.1992 and still valid on 11.12.2001 (patent law change 1993)
2002-04-24	OR01	Other related matters
2003-07-02	C19	Lapse of patent right due to non-payment of the annual fee
2003-07-02	CF01	Termination of patent right due to non-payment of annual fee

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