BR9917235A - Preparation method of cyclohexanecarboxylic acid using the [2 + 4] diels-alder reaction - Google Patents
Preparation method of cyclohexanecarboxylic acid using the [2 + 4] diels-alder reactionInfo
- Publication number
- BR9917235A BR9917235A BR9917235-6A BR9917235A BR9917235A BR 9917235 A BR9917235 A BR 9917235A BR 9917235 A BR9917235 A BR 9917235A BR 9917235 A BR9917235 A BR 9917235A
- Authority
- BR
- Brazil
- Prior art keywords
- diels
- reaction
- alder
- carried out
- acid
- Prior art date
Links
- 238000005698 Diels-Alder reaction Methods 0.000 title abstract 4
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 title abstract 4
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 abstract 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 4
- 238000006243 chemical reaction Methods 0.000 abstract 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- -1 for example Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- JSSXHAMIXJGYCS-UHFFFAOYSA-N piperazin-4-ium-2-carboxylate Chemical compound OC(=O)C1CNCCN1 JSSXHAMIXJGYCS-UHFFFAOYSA-N 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 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)
Abstract
"MéTODO DE PREPARAçãO DE áCIDOCICLOEXANOCARBOXìLICO QUE USA A REAçãO DE [2+4]DIELS-ALDER". no qual é descrito um método de preparação deácido cicloexanocarboxílico, no qual 1,3-butadieno e ácido acrílicosão submetidos à reação de [2+4] Diels-Alder para produzirem oácido 3-cicloexeno-1-carboxílico que então é hidrogenado. Areação de [2+4] Diels-Alder é realizada a uma temperatura detemperatura ambiente de 200<198>C em um solvente dehidrocarboneto aromático, por exemplo, tolueno ou xilênio. Ahidrogenação é realizada a uma temperatura de temperaturaambiente de 150<198>C, sob uma pressão de hidrogênio de 10 psia 150 psi na presença do catalisador de paládio ou de platina. Ométodo descrito é representado, uma vez que permite o uso de1,3-butadieno como matéria-prima para as substâncias químicaspuras, ao contrário dos métodos anteriores. Além disso, o métododescrito é conveniente, porque a reação pode ser realizada deuma maneira relativamente simples e fácil e os produtos derivadosda reação também podem ser convenientemente tratados após areação."METHOD OF PREPARATION OF CYCOCLOEXANOCARBOXYLIC ACID THAT USES THE REACTION OF [2 + 4] DIELS-ALDER". in which a method of preparing cyclohexanecarboxylic acid is described, in which 1,3-butadiene and acrylic acid are subjected to the reaction of [2 + 4] Diels-Alder to produce 3-cyclohexene-1-carboxylic acid which is then hydrogenated. [2 + 4] Diels-Alder sanding is carried out at an ambient temperature of 200 <198> C in an aromatic hydrocarbon solvent, for example, toluene or xylene. Hydrogenation is carried out at an ambient temperature of 150 <198> C, under a hydrogen pressure of 10 psia 150 psi in the presence of the palladium or platinum catalyst. The described method is represented, since it allows the use of 1,3-butadiene as raw material for pure chemical substances, unlike the previous methods. In addition, the method described is convenient, because the reaction can be carried out in a relatively simple and easy way and the products derived from the reaction can also be conveniently treated after sanding.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR19990004025 | 1999-02-05 | ||
| KR1019990037508A KR20000056975A (en) | 1999-02-05 | 1999-09-03 | A method of preparing cyclohexanecarboxlic acid using [2+4] Diels-Alder reaction |
| 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 |
|---|---|
| BR9917235A true BR9917235A (en) | 2001-11-27 |
Family
ID=26634676
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR9917235-6A BR9917235A (en) | 1999-02-05 | 1999-12-04 | Preparation method of cyclohexanecarboxylic acid using the [2 + 4] diels-alder reaction |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP1187801A4 (en) |
| JP (1) | JP2002539083A (en) |
| KR (1) | KR20000056975A (en) |
| CN (1) | CN1348437A (en) |
| AU (1) | AU1513800A (en) |
| BR (1) | BR9917235A (en) |
| CA (1) | CA2361682A1 (en) |
| HU (1) | HUP0200112A3 (en) |
| PL (1) | PL350029A1 (en) |
| WO (1) | WO2000046174A1 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100496763B1 (en) * | 2002-04-23 | 2005-06-22 | 한국과학기술연구원 | Method to produce cyclohexanecarboxylic acid by the hydrogenation of benzoic acid at the aqueous phase |
| KR20040026964A (en) * | 2002-09-27 | 2004-04-01 | 금호석유화학 주식회사 | Synthesis of cyclohexyl phenyl ketone from 1,3-butadiene and acrylic acid |
| CN101768074B (en) * | 2009-12-29 | 2017-09-26 | 大连九信精细化工有限公司 | A kind of new method for synthesizing 4 carboxymethyl cyclohexane-carboxylic acids |
| DE102010040282A1 (en) * | 2010-09-06 | 2012-03-08 | Evonik Röhm Gmbh | Functional materials with controllable viscosity or reversible crosslinking via aza-Diels-Alder reactions with bishydrazones or conjugated bis-Schiff bases |
| 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/en not_active Application Discontinuation
- 1999-12-04 CA CA002361682A patent/CA2361682A1/en not_active Abandoned
- 1999-12-04 PL PL99350029A patent/PL350029A1/en unknown
- 1999-12-04 AU AU15138/00A patent/AU1513800A/en not_active Abandoned
- 1999-12-04 HU HU0200112A patent/HUP0200112A3/en unknown
- 1999-12-04 BR BR9917235-6A patent/BR9917235A/en not_active Application Discontinuation
- 1999-12-04 CN CN99816019A patent/CN1348437A/en active Pending
- 1999-12-04 EP EP99957434A patent/EP1187801A4/en not_active Withdrawn
- 1999-12-04 WO PCT/KR1999/000739 patent/WO2000046174A1/en not_active Application Discontinuation
- 1999-12-04 JP JP2000597247A patent/JP2002539083A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CA2361682A1 (en) | 2000-08-10 |
| EP1187801A1 (en) | 2002-03-20 |
| JP2002539083A (en) | 2002-11-19 |
| PL350029A1 (en) | 2002-10-21 |
| EP1187801A4 (en) | 2002-09-18 |
| CN1348437A (en) | 2002-05-08 |
| AU1513800A (en) | 2000-08-25 |
| WO2000046174A1 (en) | 2000-08-10 |
| HUP0200112A3 (en) | 2003-02-28 |
| KR20000056975A (en) | 2000-09-15 |
| HUP0200112A2 (en) | 2002-05-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA10 | Dismissal: dismissal - article 33 of industrial property law | ||
| B11Y | Definitive dismissal - extension of time limit for request of examination expired [chapter 11.1.1 patent gazette] |