CH627430A5 - Process for preparing alpha -ketocarboxylic acids - Google Patents

Process for preparing alpha -ketocarboxylic acids Download PDF

Info

Publication number: CH627430A5
Authority: CH; Switzerland
Prior art keywords: formula; acid; ketocarboxylic acids; acids; carboxamides
Prior art date: 1977-02-25

Application number

CH690477A

Other languages

German (de)

English (en)

Inventor

Axel Dr Dipl Chem Kleemann

Herbert Dr Dipl Chem Klenk

Werner Dr Dipl Chem Schwarze

Original Assignee

Degussa

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.)

1977-02-25

Filing date

1977-06-03

Publication date

1982-01-15

1977-06-03 Application filed by Degussa filed Critical Degussa

1982-01-15 Publication of CH627430A5 publication Critical patent/CH627430A5/de

Links

239000002253 acid Substances 0.000 title claims description 25
150000007513 acids Chemical class 0.000 title claims description 12
238000004519 manufacturing process Methods 0.000 title description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 17
238000000034 method Methods 0.000 claims description 17
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 12
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
238000007127 saponification reaction Methods 0.000 claims description 8
150000001264 acyl cyanides Chemical class 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 6
150000001408 amides Chemical class 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 4
150000003857 carboxamides Chemical class 0.000 claims description 4
238000005903 acid hydrolysis reaction Methods 0.000 claims description 3
230000002378 acidificating effect Effects 0.000 claims description 3
238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
239000003791 organic solvent mixture Substances 0.000 claims 2
125000000753 cycloalkyl group Chemical group 0.000 claims 1
239000007788 liquid Substances 0.000 claims 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
-1 2,2-dichloro-l-methylcyclopropyl Chemical group 0.000 description 8
239000000203 mixture Substances 0.000 description 8
150000004715 keto acids Chemical class 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000009835 boiling Methods 0.000 description 6
GZTZLYWUGFZVSM-UHFFFAOYSA-N 2-methylpropanoyl cyanide Chemical compound CC(C)C(=O)C#N GZTZLYWUGFZVSM-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
239000007789 gas Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
VGZJMWGPDOEDES-UHFFFAOYSA-N 2-(2,2-dichloro-1,3-dimethylcyclopropyl)-2-oxoacetic acid Chemical class CC1C(Cl)(Cl)C1(C)C(=O)C(O)=O VGZJMWGPDOEDES-UHFFFAOYSA-N 0.000 description 2
UYCTVHPXUZNWSQ-UHFFFAOYSA-N 3-methylbutanoyl cyanide Chemical compound CC(C)CC(=O)C#N UYCTVHPXUZNWSQ-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
XIPUIGPNIDKXJU-UHFFFAOYSA-N [CH]1CC1 Chemical compound [CH]1CC1 XIPUIGPNIDKXJU-UHFFFAOYSA-N 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 2
239000013078 crystal Substances 0.000 description 2
OXFVCMMQMWINHL-UHFFFAOYSA-N cyclopropanecarbonyl cyanide Chemical compound N#CC(=O)C1CC1 OXFVCMMQMWINHL-UHFFFAOYSA-N 0.000 description 2
238000004508 fractional distillation Methods 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
239000002904 solvent Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
CWJGJYVZUJEBFS-UHFFFAOYSA-N 2-cyclopropyl-2-oxoacetamide Chemical compound NC(=O)C(=O)C1CC1 CWJGJYVZUJEBFS-UHFFFAOYSA-N 0.000 description 1
LCSYJVAKMPOJIB-UHFFFAOYSA-N 2-cyclopropyl-2-oxoacetic acid Chemical compound OC(=O)C(=O)C1CC1 LCSYJVAKMPOJIB-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
TYEYBOSBBBHJIV-UHFFFAOYSA-N 2-oxobutanoic acid Chemical compound CCC(=O)C(O)=O TYEYBOSBBBHJIV-UHFFFAOYSA-N 0.000 description 1
QHKABHOOEWYVLI-UHFFFAOYSA-N 3-methyl-2-oxobutanoic acid Chemical compound CC(C)C(=O)C(O)=O QHKABHOOEWYVLI-UHFFFAOYSA-N 0.000 description 1
VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 1
150000001266 acyl halides Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
229940093476 ethylene glycol Drugs 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000011005 laboratory method Methods 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
AHAXISXGFCFQGE-UHFFFAOYSA-N n-oxoformamide Chemical class O=CN=O AHAXISXGFCFQGE-UHFFFAOYSA-N 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
JQLHQBWQAFDAGK-UHFFFAOYSA-N propanoyl cyanide Chemical compound CCC(=O)C#N JQLHQBWQAFDAGK-UHFFFAOYSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000005891 transamination reaction Methods 0.000 description 1
238000010792 warming 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
- C07C51/06—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid amides

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)

CH690477A 1977-02-25 1977-06-03 Process for preparing alpha -ketocarboxylic acids CH627430A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2708185A DE2708185C3 (de)	1977-02-25	1977-02-25	Verfahren zur Herstellung von α-Ketocarbonsäuren

Publications (1)

Publication Number	Publication Date
CH627430A5 true CH627430A5 (en)	1982-01-15

Family

ID=6002153

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH690477A CH627430A5 (en)	1977-02-25	1977-06-03	Process for preparing alpha -ketocarboxylic acids

Country Status (12)

Country	Link
JP (1)	JPS6055497B2 (fr)
AT (1)	AT367014B (fr)
BE (1)	BE855257A (fr)
CH (1)	CH627430A5 (fr)
DD (1)	DD131013A5 (fr)
DE (1)	DE2708185C3 (fr)
FR (1)	FR2381735A1 (fr)
GB (1)	GB1533818A (fr)
IL (1)	IL52239A (fr)
IT (1)	IT1143581B (fr)
NL (1)	NL7706161A (fr)
SU (1)	SU793376A3 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4234739A (en) *	1978-12-05	1980-11-18	Stauffer Chemical Company	Method for preparing glyoxylic acids and derivatives thereof
DE3003541A1 (de) *	1980-01-31	1981-08-06	Bayer Ag, 5090 Leverkusen	Verfahren zur herstellung von 4-amino-6-tert.-butyl-3-methylthio-1,2,4-triazin-5(4h)-on
DE3009043A1 (de) *	1980-03-08	1981-09-24	Bayer Ag, 5090 Leverkusen	Verfahren zur herstellung von 4-amino-6-tert.-butyl-3-methylthio-1,2,4-triazin-5(4h)-on
DE3134230A1 (de) *	1981-08-29	1983-03-10	Bayer Ag, 5090 Leverkusen	Verfahren zur herstellung von 4-methyl-5-oxo-3-thioxo-tetrahydro-1,2,4-(2h,4h)-triazinen
EP0141876B1 (en) *	1983-11-15	1987-03-11	Ethyl Corporation	Preparation of cyclic-keto-acids
CA2484871C (fr) *	2002-08-26	2010-11-30	Ajinomoto Co., Inc.	Nouvelle aldolase et procede de production d'alpha-cetoacides substitues

1977
- 1977-02-25 DE DE2708185A patent/DE2708185C3/de not_active Expired
- 1977-05-31 BE BE6046035A patent/BE855257A/fr not_active IP Right Cessation
- 1977-06-01 IT IT49656/77A patent/IT1143581B/it active
- 1977-06-02 SU SU772489000A patent/SU793376A3/ru active
- 1977-06-02 AT AT0392777A patent/AT367014B/de not_active IP Right Cessation
- 1977-06-03 NL NL7706161A patent/NL7706161A/xx not_active Application Discontinuation
- 1977-06-03 IL IL52239A patent/IL52239A/xx unknown
- 1977-06-03 DD DD7700199296A patent/DD131013A5/xx unknown
- 1977-06-03 CH CH690477A patent/CH627430A5/de not_active IP Right Cessation
- 1977-06-03 FR FR7717128A patent/FR2381735A1/fr active Granted
- 1977-06-03 JP JP52065654A patent/JPS6055497B2/ja not_active Expired
- 1977-06-03 GB GB23669/77A patent/GB1533818A/en not_active Expired

Also Published As

Publication number	Publication date
ATA392777A (de)	1981-10-15
NL7706161A (nl)	1978-08-29
SU793376A3 (ru)	1980-12-30
GB1533818A (en)	1978-11-29
DE2708185C3 (de)	1981-06-04
DE2708185B2 (de)	1978-11-30
IT1143581B (it)	1986-10-22
JPS53105423A (en)	1978-09-13
JPS6055497B2 (ja)	1985-12-05
IL52239A (en)	1980-11-30
DE2708185A1 (de)	1978-08-31
DD131013A5 (de)	1978-05-24
IL52239A0 (en)	1977-08-31
FR2381735B1 (fr)	1980-01-18
FR2381735A1 (fr)	1978-09-22
AT367014B (de)	1982-05-25
BE855257A (fr)	1977-11-30

Legal Events

Date	Code	Title	Description
1992-02-28	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE69513657T2 (de)	2000-04-06	Verfahren zur Herstellung von 1-substituierten 2-Cyanoimidazolen
DE2708185C3 (de)	1981-06-04	Verfahren zur Herstellung von α-Ketocarbonsäuren
EP0132733A2 (fr)	1985-02-13	Fluorures d'acide fluoropivalique et procédé de leur préparation
DE2642140C2 (de)	1982-10-28	Verfahren zur Herstellung von Benzoylcyanid
DE3026094C2 (de)	1983-01-05	Verfahren zur Herstellung von Cyclopropancarbonsäureamiden
CH497367A (de)	1970-10-15	Verfahren zur Herstellung von Zimtsäurederivaten und deren Verwendung
CH619955A5 (fr)	1980-10-31
DE2721265C2 (de)	1982-05-19	Verfahren zur Herstellung von Di- n-propylacetonitril
DE2708184C3 (de)	1980-02-07	Verfahren zur Herstellung von a -Ketocarbonsäureamide!! (A)
CH626332A5 (fr)	1981-11-13
DE2731543C3 (de)	1980-07-31	Verfahren zur Herstellung von Cyclopentadecanolid
EP0046193B1 (fr)	1983-09-28	Hydroxy-1 pyrazole et son procédé de préparation
EP0089485A2 (fr)	1983-09-28	Procédé pour préparer des esters de l'acide 5-chloro-1H-tétrazolo-1-carboxylique, ainsi que procédé pour préparer les esters de l'acide dichloroisonitrile-carboxylique nécessaires
DE2727613A1 (de)	1977-12-29	Cyanosubstituierte cyclopropanderivate und verfahren zu ihrer herstellung
DE2623848A1 (de)	1977-12-08	Verfahren zur herstellung von 2,2- dimethyl-3-(2',2'-dihalogenvinyl)-cyclopropan-1-carbonsaeureester
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AT209325B (de)	1960-05-25	Verfahren zur Herstellung des ß-Hydromuconsäure-Halbnitrils und dessen Ester
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DE2429757C3 (de)	1977-03-10	Verfahren zur Herstellung von 3-Hexin-1-ol
DE2802387C2 (de)	1980-04-03	Verfahren zur Herstellung von Thiazo-üdin-4-on-essigsäure-Derivaten
DE3231815A1 (de)	1984-03-01	Dialkoxymethyl-butyrolactone, verfahren zu ihrer herstellung, zwischenprodukte dafuer und ihre verwendung
DE2526652A1 (de)	1976-12-30	N-(trifluormethylbenzyl)-phthalimide
DE1019302B (de)	1957-11-14	Verfahren zur Herstellung neuer Derivate des 1, 4-Androstadien-3, 11, 17-trions [1 (2)-Dehydroadrenosterons]
WO1998018795A1 (fr)	1998-05-07	Procede de fabrication de composes de naphtyridine et nouveaux produits intermediaires