CA2361682A1 - A method of preparing cyclohexanecaraboxylic acid using ¬2+4| diels-alder reaction - Google Patents
A method of preparing cyclohexanecaraboxylic acid using ¬2+4| diels-alder reaction Download PDFInfo
- Publication number
- CA2361682A1 CA2361682A1 CA002361682A CA2361682A CA2361682A1 CA 2361682 A1 CA2361682 A1 CA 2361682A1 CA 002361682 A CA002361682 A CA 002361682A CA 2361682 A CA2361682 A CA 2361682A CA 2361682 A1 CA2361682 A1 CA 2361682A1
- Authority
- CA
- Canada
- Prior art keywords
- reaction
- diels
- carried out
- acid
- cyclohexene
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 42
- 238000005698 Diels-Alder reaction Methods 0.000 title claims abstract description 24
- 239000002253 acid Substances 0.000 title 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 33
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims abstract description 32
- JSSXHAMIXJGYCS-UHFFFAOYSA-N piperazin-4-ium-2-carboxylate Chemical compound OC(=O)C1CNCCN1 JSSXHAMIXJGYCS-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000003054 catalyst Substances 0.000 claims abstract description 21
- 239000002904 solvent Substances 0.000 claims abstract description 20
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 14
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000008096 xylene Substances 0.000 claims abstract description 10
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000003112 inhibitor Substances 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- 239000007810 chemical reaction solvent Substances 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- FPIQZBQZKBKLEI-UHFFFAOYSA-N ethyl 1-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylate Chemical compound ClCCN(N=O)C(=O)NC1(C(=O)OCC)CCCCC1 FPIQZBQZKBKLEI-UHFFFAOYSA-N 0.000 claims description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 4
- XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-UHFFFAOYSA-N 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 abstract description 50
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 abstract description 25
- 238000006243 chemical reaction Methods 0.000 abstract description 24
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract description 13
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract description 4
- 239000012847 fine chemical Substances 0.000 abstract description 4
- 239000006227 byproduct Substances 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 2
- 230000000694 effects Effects 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 239000011369 resultant mixture Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- VUSWCWPCANWBFG-UHFFFAOYSA-N cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC=CC1 VUSWCWPCANWBFG-UHFFFAOYSA-N 0.000 description 2
- 150000005379 cyclohexanecarboxylic acid derivatives Chemical class 0.000 description 2
- -1 ethanol and methanol Chemical compound 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- WMJMABVHDMRMJA-UHFFFAOYSA-M [Cl-].[Mg+]C1CCCCC1 Chemical compound [Cl-].[Mg+]C1CCCCC1 WMJMABVHDMRMJA-UHFFFAOYSA-M 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- QCTBMLYLENLHLA-UHFFFAOYSA-N aminomethylbenzoic acid Chemical compound NCC1=CC=C(C(O)=O)C=C1 QCTBMLYLENLHLA-UHFFFAOYSA-N 0.000 description 1
- 229960003375 aminomethylbenzoic acid Drugs 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000021523 carboxylation Effects 0.000 description 1
- 238000006473 carboxylation reaction Methods 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- AVKNGPAMCBSNSO-UHFFFAOYSA-N cyclohexylmethanamine Chemical compound NCC1CCCCC1 AVKNGPAMCBSNSO-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/36—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by hydrogenation of carbon-to-carbon unsaturated bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR19990004025 | 1999-02-05 | ||
| KR1999/37508 | 1999-09-03 | ||
| KR1019990037508A KR20000056975A (ko) | 1999-02-05 | 1999-09-03 | [2+4] 딜즈-알더 반응을 이용하는 시클로헥산카르복실산의 제조방법 |
| KR1999/4025 | 1999-09-03 | ||
| PCT/KR1999/000739 WO2000046174A1 (en) | 1999-02-05 | 1999-12-04 | A method of preparing cyclohexanecaraboxylic acid using [2+4] diels-alder reaction |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2361682A1 true CA2361682A1 (en) | 2000-08-10 |
Family
ID=26634676
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002361682A Abandoned CA2361682A1 (en) | 1999-02-05 | 1999-12-04 | A method of preparing cyclohexanecaraboxylic acid using ¬2+4| diels-alder reaction |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP1187801A4 (hu) |
| JP (1) | JP2002539083A (hu) |
| KR (1) | KR20000056975A (hu) |
| CN (1) | CN1348437A (hu) |
| AU (1) | AU1513800A (hu) |
| BR (1) | BR9917235A (hu) |
| CA (1) | CA2361682A1 (hu) |
| HU (1) | HUP0200112A3 (hu) |
| PL (1) | PL350029A1 (hu) |
| WO (1) | WO2000046174A1 (hu) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100496763B1 (ko) * | 2002-04-23 | 2005-06-22 | 한국과학기술연구원 | 벤조산의 수용액상 수소화 반응에 의한 사이클로헥산카르복실산의 제조방법 |
| KR20040026964A (ko) * | 2002-09-27 | 2004-04-01 | 금호석유화학 주식회사 | 1,3-부타디엔과 아크릴산으로부터 시클로헥실 페닐 케톤의제조방법 |
| CN101768074B (zh) * | 2009-12-29 | 2017-09-26 | 大连九信精细化工有限公司 | 一种合成4‑羧甲基环己烷羧酸的新方法 |
| DE102010040282A1 (de) * | 2010-09-06 | 2012-03-08 | Evonik Röhm Gmbh | Funktionsmaterialien mit steuerbarer Viskosität bzw. reversibler Vernetzung über Aza-Diels-Alder-Reaktionen mit Bishydrazonen oder konjugierten Bis-Schiff'schen Basen |
| US9115155B1 (en) * | 2014-03-20 | 2015-08-25 | Eastman Chemical Company | Low-pressure synthesis of cyclohexanedimethanol and derivatives |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54157546A (en) * | 1978-05-30 | 1979-12-12 | Mitsui Toatsu Chem Inc | Preparation of 3-cyclohexenecarboxylic acid |
-
1999
- 1999-09-03 KR KR1019990037508A patent/KR20000056975A/ko not_active Application Discontinuation
- 1999-12-04 CA CA002361682A patent/CA2361682A1/en not_active Abandoned
- 1999-12-04 AU AU15138/00A patent/AU1513800A/en not_active Abandoned
- 1999-12-04 JP JP2000597247A patent/JP2002539083A/ja active Pending
- 1999-12-04 CN CN99816019A patent/CN1348437A/zh active Pending
- 1999-12-04 WO PCT/KR1999/000739 patent/WO2000046174A1/en not_active Application Discontinuation
- 1999-12-04 BR BR9917235-6A patent/BR9917235A/pt not_active Application Discontinuation
- 1999-12-04 PL PL99350029A patent/PL350029A1/xx unknown
- 1999-12-04 EP EP99957434A patent/EP1187801A4/en not_active Withdrawn
- 1999-12-04 HU HU0200112A patent/HUP0200112A3/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP1187801A4 (en) | 2002-09-18 |
| BR9917235A (pt) | 2001-11-27 |
| CN1348437A (zh) | 2002-05-08 |
| AU1513800A (en) | 2000-08-25 |
| WO2000046174A1 (en) | 2000-08-10 |
| KR20000056975A (ko) | 2000-09-15 |
| HUP0200112A2 (hu) | 2002-05-29 |
| EP1187801A1 (en) | 2002-03-20 |
| HUP0200112A3 (en) | 2003-02-28 |
| PL350029A1 (en) | 2002-10-21 |
| JP2002539083A (ja) | 2002-11-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |