JPS6121946B2 - - Google Patents
Info
- Publication number
- JPS6121946B2 JPS6121946B2 JP8901776A JP8901776A JPS6121946B2 JP S6121946 B2 JPS6121946 B2 JP S6121946B2 JP 8901776 A JP8901776 A JP 8901776A JP 8901776 A JP8901776 A JP 8901776A JP S6121946 B2 JPS6121946 B2 JP S6121946B2
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- reaction
- oxo
- hexanoic acid
- acid amide
- 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
- 239000003054 catalyst Substances 0.000 claims description 24
- GGYVTHJIUNGKFZ-UHFFFAOYSA-N 1-methylpiperidin-2-one Chemical class CN1CCCCC1=O GGYVTHJIUNGKFZ-UHFFFAOYSA-N 0.000 claims description 8
- 238000006297 dehydration reaction Methods 0.000 claims description 7
- 230000018044 dehydration Effects 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- MFOXCBPAYMJQPW-UHFFFAOYSA-N 2-oxohexanamide Chemical class CCCCC(=O)C(N)=O MFOXCBPAYMJQPW-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 16
- GHYDKOSNFZOHJJ-UHFFFAOYSA-N 5-oxohexanamide Chemical class CC(=O)CCCC(N)=O GHYDKOSNFZOHJJ-UHFFFAOYSA-N 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 239000007789 gas Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical compound O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000008246 gaseous mixture Substances 0.000 description 2
- ALBYIUDWACNRRB-UHFFFAOYSA-N hexanamide Chemical compound CCCCCC(N)=O ALBYIUDWACNRRB-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- KWRCTXMRVADIJW-UHFFFAOYSA-N 2,4-dimethyl-5-oxohexanamide Chemical compound CC(=O)C(C)CC(C)C(N)=O KWRCTXMRVADIJW-UHFFFAOYSA-N 0.000 description 1
- MVKDNXIKAWKCCS-UHFFFAOYSA-N 3-methyl-1h-pyridin-2-one Chemical compound CC1=CC=CN=C1O MVKDNXIKAWKCCS-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Hydrogenated Pyridines (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8901776A JPS5315384A (en) | 1976-07-28 | 1976-07-28 | Preparation of methylpiperazinones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8901776A JPS5315384A (en) | 1976-07-28 | 1976-07-28 | Preparation of methylpiperazinones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5315384A JPS5315384A (en) | 1978-02-13 |
| JPS6121946B2 true JPS6121946B2 (de) | 1986-05-29 |
Family
ID=13959129
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8901776A Granted JPS5315384A (en) | 1976-07-28 | 1976-07-28 | Preparation of methylpiperazinones |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5315384A (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02244200A (ja) * | 1989-03-17 | 1990-09-28 | Akio Ogiwara | 音声信号処理用ピッチ検出回路 |
| JP2856787B2 (ja) * | 1989-10-27 | 1999-02-10 | 日本電気ホームエレクトロニクス株式会社 | ２値化回路、中間レベル検出回路及びピーク包絡線検出回路 |
-
1976
- 1976-07-28 JP JP8901776A patent/JPS5315384A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5315384A (en) | 1978-02-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS6134414B2 (de) | ||
| US3153044A (en) | Process for the preparation of 2-chloropyridine | |
| JPS6315270B2 (de) | ||
| JPS6121946B2 (de) | ||
| JPH0373535B2 (de) | ||
| WO2018186460A1 (ja) | トリフルオロメチルピリジン類の精製方法 | |
| EP1065198B1 (de) | Verfahren zur Herstellung von Malononitril | |
| JPH053455B2 (de) | ||
| JPS593994B2 (ja) | メチルピリジノン類の製造方法 | |
| JP2517304B2 (ja) | ブロモアセトニトリルの製造方法 | |
| US3766239A (en) | Ammoxidation of chloromethyl compounds | |
| JP2004059553A (ja) | アミド化合物の製造方法 | |
| JPS59225144A (ja) | ピルビン酸エステルの分離方法 | |
| US3020281A (en) | Method of preparing quinoline | |
| JP2003012646A (ja) | ２−（４−ピリジル）エタンチオールの蒸留方法 | |
| JPS63243064A (ja) | ベンゾニトリル類の製法 | |
| JPS5826733B2 (ja) | エンソカアルデヒドノ セイゾウホウホウ | |
| JP4393839B2 (ja) | １，３−ジ−ハロ置換されたベンゼン誘導体の製造 | |
| US3020280A (en) | Quinoline synthesis | |
| SU627756A3 (ru) | Способ получени дибензофурана | |
| JPH05286932A (ja) | インドール類の製造方法 | |
| JPS6313988B2 (de) | ||
| JP3371544B2 (ja) | 芳香族アルデヒドの製造方法 | |
| JPS6124569A (ja) | ２，３，５−コリジン及び／又は２，３，５，６−テトラメチルピリジンの製造法 | |
| JPS6130666B2 (de) |