JPS5844650B2 - ５−オキソカルボン酸の製法 - Google Patents
５−オキソカルボン酸の製法Info
- Publication number
- JPS5844650B2 JPS5844650B2 JP49110068A JP11006874A JPS5844650B2 JP S5844650 B2 JPS5844650 B2 JP S5844650B2 JP 49110068 A JP49110068 A JP 49110068A JP 11006874 A JP11006874 A JP 11006874A JP S5844650 B2 JPS5844650 B2 JP S5844650B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- reaction
- acrylic acid
- carried out
- methyl
- 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.)
- Expired
Links
- 239000002253 acid Substances 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 18
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 17
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 17
- 150000002576 ketones Chemical class 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- 239000002262 Schiff base Substances 0.000 claims description 4
- 150000004753 Schiff bases Chemical class 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 150000003141 primary amines Chemical class 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- IEHMHYAHHVRZIF-UHFFFAOYSA-N 4-methyl-5-oxohexanoic acid Chemical compound CC(=O)C(C)CCC(O)=O IEHMHYAHHVRZIF-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
- IOWZXZAFYLFVTA-UHFFFAOYSA-N 5-oxo-4-phenylhexanoic acid Chemical compound OC(=O)CCC(C(=O)C)C1=CC=CC=C1 IOWZXZAFYLFVTA-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
- 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
- 150000003863 ammonium salts Chemical class 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
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 description 1
- PHZPKPLQXCKVTF-UHFFFAOYSA-N 2-(2-oxocyclohexyl)propanoic acid Chemical compound OC(=O)C(C)C1CCCCC1=O PHZPKPLQXCKVTF-UHFFFAOYSA-N 0.000 description 1
- JCIZEWRBCTUEFG-UHFFFAOYSA-N 3-(2-oxocyclohexyl)propanoic acid Chemical compound OC(=O)CCC1CCCCC1=O JCIZEWRBCTUEFG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 238000006845 Michael addition reaction Methods 0.000 description 1
- -1 acrylyl Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007127 saponification reaction Methods 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
- 239000002904 solvent Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2348536A DE2348536C3 (de) | 1973-09-27 | 1973-09-27 | Verfahren zur Herstellung von 5-Oxocarbonsäuren |
| DE2348536 | 1973-09-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5059323A JPS5059323A (enrdf_load_stackoverflow) | 1975-05-22 |
| JPS5844650B2 true JPS5844650B2 (ja) | 1983-10-04 |
Family
ID=5893770
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP49110068A Expired JPS5844650B2 (ja) | 1973-09-27 | 1974-09-26 | ５−オキソカルボン酸の製法 |
Country Status (11)
Families Citing this family (3)
| 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 NL NL7412470A patent/NL7412470A/xx not_active Application Discontinuation
- 1974-09-20 ZA ZA00745966A patent/ZA745966B/xx unknown
- 1974-09-20 CA CA209,699A patent/CA1043352A/en not_active Expired
- 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 GB GB4204474A patent/GB1476153A/en not_active Expired
- 1974-09-27 BE BE148988A patent/BE820449A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH605558A5 (enrdf_load_stackoverflow) | 1978-09-29 |
| NL7412470A (nl) | 1975-04-02 |
| DE2348536B2 (de) | 1978-07-20 |
| FR2245605B1 (enrdf_load_stackoverflow) | 1979-02-02 |
| FR2245605A1 (enrdf_load_stackoverflow) | 1975-04-25 |
| ZA745966B (en) | 1975-11-26 |
| DE2348536C3 (de) | 1979-03-29 |
| GB1476153A (en) | 1977-06-10 |
| IT1022317B (it) | 1978-03-20 |
| JPS5059323A (enrdf_load_stackoverflow) | 1975-05-22 |
| BE820449A (fr) | 1975-03-27 |
| DE2348536A1 (de) | 1975-04-03 |
| CA1043352A (en) | 1978-11-28 |
| BR7407939D0 (pt) | 1975-07-29 |
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