CA1043352A - Synthese d'acides oxo-5 carboxyliques - Google Patents

Synthese d'acides oxo-5 carboxyliques

Info

Publication number: CA1043352A
Authority: CA; Canada
Prior art keywords: ketone; acrylic acid; reaction; methyl; acid
Prior art date: 1973-09-27
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

Application number

CA209,699A

Other languages

English (en)

Inventor

Werner H. Muller

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.)

Hoechst AG

Original Assignee

Hoechst AG

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.)

1973-09-27

Filing date

1974-09-20

Publication date

1978-11-28

1974-09-20 Application filed by Hoechst AG filed Critical Hoechst AG

1978-11-28 Application granted granted Critical

1978-11-28 Publication of CA1043352A publication Critical patent/CA1043352A/fr

Status Expired legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title abstract description 3
150000002576 ketones Chemical class 0.000 claims abstract description 11
239000003054 catalyst Substances 0.000 claims abstract description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 6
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims abstract description 3
229910021529 ammonia Inorganic materials 0.000 claims abstract description 3
150000003141 primary amines Chemical class 0.000 claims abstract description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 21
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 20
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 20
238000006243 chemical reaction Methods 0.000 claims description 20
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
238000000034 method Methods 0.000 claims description 14
-1 aliphatic amino-alcohols Chemical class 0.000 claims description 8
OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 claims description 4
QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 claims description 4
ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 claims description 4
SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 claims description 4
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 4
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 4
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims description 4
CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 claims description 4
VKCYHJWLYTUGCC-UHFFFAOYSA-N nonan-2-one Chemical compound CCCCCCCC(C)=O VKCYHJWLYTUGCC-UHFFFAOYSA-N 0.000 claims description 4
XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 claims description 4
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims description 4
QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 claims description 4
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 2
WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims description 2
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
229930016911 cinnamic acid Natural products 0.000 claims description 2
235000013985 cinnamic acid Nutrition 0.000 claims description 2
LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims description 2
239000007792 gaseous phase Substances 0.000 claims description 2
239000007791 liquid phase Substances 0.000 claims description 2
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 2
PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 claims description 2
LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims description 2
UIERETOOQGIECD-UHFFFAOYSA-N 2-methylbut-2-enoic acid Chemical compound CC=C(C)C(O)=O UIERETOOQGIECD-UHFFFAOYSA-N 0.000 claims 1
LFSAPCRASZRSKS-UHFFFAOYSA-N 2-methylcyclohexan-1-one Chemical compound CC1CCCCC1=O LFSAPCRASZRSKS-UHFFFAOYSA-N 0.000 claims 1
229940063559 methacrylic acid Drugs 0.000 claims 1
150000001253 acrylic acids Chemical class 0.000 abstract description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
PHADZMIQVBXNAW-UHFFFAOYSA-N 4-propionyl butyric acid Chemical compound CCC(=O)CCCC(O)=O PHADZMIQVBXNAW-UHFFFAOYSA-N 0.000 description 2
MGTZCLMLSSAXLD-UHFFFAOYSA-N 5-oxohexanoic acid Chemical compound CC(=O)CCCC(O)=O MGTZCLMLSSAXLD-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical compound CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 description 2
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
239000002904 solvent Substances 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
RJKCQJNOJDMYEM-UHFFFAOYSA-N 2-methyl-5-oxohexanoic acid Chemical compound OC(=O)C(C)CCC(C)=O RJKCQJNOJDMYEM-UHFFFAOYSA-N 0.000 description 1
IEHMHYAHHVRZIF-UHFFFAOYSA-N 4-methyl-5-oxohexanoic acid Chemical compound CC(=O)C(C)CCC(O)=O IEHMHYAHHVRZIF-UHFFFAOYSA-N 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
150000001414 amino alcohols Chemical class 0.000 description 1
229960002684 aminocaproic acid Drugs 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 1
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
125000002837 carbocyclic group Chemical group 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
125000006165 cyclic alkyl group Chemical group 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
WVRIJHGUJNXDRZ-UHFFFAOYSA-N ethane-1,1-diamine Chemical compound CC(N)N WVRIJHGUJNXDRZ-UHFFFAOYSA-N 0.000 description 1
235000013905 glycine and its sodium salt Nutrition 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
238000010517 secondary reaction Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
239000002351 wastewater Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/185—Saturated compounds having only one carboxyl group and containing keto groups
- 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
- C07C51/373—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in doubly bound form

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA209,699A 1973-09-27 1974-09-20 Synthese d'acides oxo-5 carboxyliques Expired CA1043352A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2348536A DE2348536C3 (de)	1973-09-27	1973-09-27	Verfahren zur Herstellung von 5-Oxocarbonsäuren

Publications (1)

Publication Number	Publication Date
CA1043352A true CA1043352A (fr)	1978-11-28

Family

ID=5893770

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA209,699A Expired CA1043352A (fr)	1973-09-27	1974-09-20	Synthese d'acides oxo-5 carboxyliques

Country Status (11)

Country	Link
JP (1)	JPS5844650B2 (fr)
BE (1)	BE820449A (fr)
BR (1)	BR7407939D0 (fr)
CA (1)	CA1043352A (fr)
CH (1)	CH605558A5 (fr)
DE (1)	DE2348536C3 (fr)
FR (1)	FR2245605B1 (fr)
GB (1)	GB1476153A (fr)
IT (1)	IT1022317B (fr)
NL (1)	NL7412470A (fr)
ZA (1)	ZA745966B (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL7808605A (nl) *	1978-08-19	1980-02-21	Stamicarbon	Werkwijze voor de bereiding van delta-ketozuren en derivaten hiervan.
DE2921430A1 (de) *	1979-05-26	1980-12-04	Haarmann & Reimer Gmbh	3-methyl-5-keto- alpha , omega -alken- dicarbonsaeuren, verfahren zu ihrer herstellung und ihre verwendung zur herstellung makrocyclischer beta -methyl-ketone
JPS60152440A (ja) *	1984-01-21	1985-08-10	Sumitomo Chem Co Ltd	δ−オキソカルボン酸及びその誘導体の製造方法

1973
- 1973-09-27 DE DE2348536A patent/DE2348536C3/de not_active Expired
1974
- 1974-09-20 CA CA209,699A patent/CA1043352A/fr not_active Expired
- 1974-09-20 ZA ZA00745966A patent/ZA745966B/xx unknown
- 1974-09-20 NL NL7412470A patent/NL7412470A/xx not_active Application Discontinuation
- 1974-09-24 CH CH1289374A patent/CH605558A5/xx not_active IP Right Cessation
- 1974-09-25 IT IT27712/74A patent/IT1022317B/it active
- 1974-09-25 BR BR7939/74A patent/BR7407939D0/pt unknown
- 1974-09-26 JP JP49110068A patent/JPS5844650B2/ja not_active Expired
- 1974-09-27 FR FR7432636A patent/FR2245605B1/fr not_active Expired
- 1974-09-27 BE BE148988A patent/BE820449A/fr unknown
- 1974-09-27 GB GB4204474A patent/GB1476153A/en not_active Expired

Also Published As

Publication number	Publication date
BR7407939D0 (pt)	1975-07-29
DE2348536B2 (de)	1978-07-20
ZA745966B (en)	1975-11-26
FR2245605B1 (fr)	1979-02-02
BE820449A (fr)	1975-03-27
GB1476153A (en)	1977-06-10
FR2245605A1 (fr)	1975-04-25
DE2348536A1 (de)	1975-04-03
JPS5059323A (fr)	1975-05-22
CH605558A5 (fr)	1978-09-29
JPS5844650B2 (ja)	1983-10-04
NL7412470A (nl)	1975-04-02
IT1022317B (it)	1978-03-20
DE2348536C3 (de)	1979-03-29

Publication	Publication Date	Title
US2697118A (en)	1954-12-14	Totally hydroxypropylated alkylene diamines
EP0150558A2 (fr)	1985-08-07	Préparation de polyéthylène-polyamines à l'aide de catalyseurs silice-alumine
US3366687A (en)	1968-01-30	Process for preparing primary and secondary amines
US2850519A (en)	1958-09-02	Process for the production of alpha-monocyanethylated ketones
US2513996A (en)	1950-07-04	Reaction of a primary amine with an imine
CN110606834A (zh)	2019-12-24	一种丙烯酰吗啉的制备方法
US2486648A (en)	1949-11-01	Production of diamines
US4642344A (en)	1987-02-10	Polyamines
US4459423A (en)	1984-07-10	Process for producing α-amino acids
US3780082A (en)	1973-12-18	Process for the preparation of 4-oxocapronitrile
US4001294A (en)	1977-01-04	Method of preparing unsaturated dinitriles
CA1076136A (fr)	1980-04-22	Preparation de l'acide 5-oxohexanoique et de ses derives
US2598811A (en)	1952-06-03	Of aigomattc
CA1147750A (fr)	1983-06-07	Methode de preparation d'amides anti-oxydants
US2585230A (en)	1952-02-12	N-fluoroalkyl-n-vinylalkanamides and preparation thereof
US3962270A (en)	1976-06-08	Process for preparing 2-vinyl oxazolines
EP0330205B1 (fr)	1994-06-08	Procédé pour la synthèse de carboxamides
US4644083A (en)	1987-02-17	Process for the production of N-substituted α,β-unsaturated carboxylic acid amides
US2987556A (en)	1961-06-06	1-vinyl-3-cyclohexenol
US5276192A (en)	1994-01-04	Preparation of phenoxyethanamines
DE2348536C3 (de)	1979-03-29	Verfahren zur Herstellung von 5-Oxocarbonsäuren
EP1027327A1 (fr)	2000-08-16	Formation de quinonediimines a partir de phenylenediamines par oxydation catalytique
JPS62167745A (ja)	1987-07-24	Ｎ，ｎ−ジエチルアニリン類の製法
EP0186950B1 (fr)	1990-04-25	1,6-Hexanediamides à partir de 3-pentèneamides
Murakami et al.	1996	Preparation of (Alkaneimidoyl) lanthanides and Their Reactions with Carbonyl Compounds.