JPS6056707B2 - ２−ピロリドンの製造方法 - Google Patents
２−ピロリドンの製造方法Info
- Publication number
- JPS6056707B2 JPS6056707B2 JP2204676A JP2204676A JPS6056707B2 JP S6056707 B2 JPS6056707 B2 JP S6056707B2 JP 2204676 A JP2204676 A JP 2204676A JP 2204676 A JP2204676 A JP 2204676A JP S6056707 B2 JPS6056707 B2 JP S6056707B2
- Authority
- JP
- Japan
- Prior art keywords
- hydrogenation
- carried out
- pyrrolidone
- partial pressure
- hydrogen partial
- 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
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 238000005984 hydrogenation reaction Methods 0.000 claims description 17
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 229910021529 ammonia Inorganic materials 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- IAHFWCOBPZCAEA-UHFFFAOYSA-N succinonitrile Chemical compound N#CCCC#N IAHFWCOBPZCAEA-UHFFFAOYSA-N 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 150000003953 γ-lactams Chemical class 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- PIYZBBVETVKTQT-UHFFFAOYSA-N 2-(2-methylpropyl)butanedioic acid Chemical compound CC(C)CC(C(O)=O)CC(O)=O PIYZBBVETVKTQT-UHFFFAOYSA-N 0.000 description 1
- XGYKKVTZDQDYJQ-UHFFFAOYSA-N 4-aminobutanenitrile Chemical compound NCCCC#N XGYKKVTZDQDYJQ-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229920001007 Nylon 4 Polymers 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 210000003746 feather Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D201/00—Preparation, separation, purification or stabilisation of unsubstituted lactams
- C07D201/02—Preparation of lactams
- C07D201/08—Preparation of lactams from carboxylic acids or derivatives thereof, e.g. hydroxy carboxylic acids, lactones or nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7502574A NL184953C (nl) | 1975-03-05 | 1975-03-05 | Werkwijze voor de bereiding van een al of niet gesubstitueerd 2-pyrrolidinon. |
| NL7502574 | 1975-03-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS51110560A JPS51110560A (ja) | 1976-09-30 |
| JPS6056707B2 true JPS6056707B2 (ja) | 1985-12-11 |
Family
ID=19823302
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2204676A Expired JPS6056707B2 (ja) | 1975-03-05 | 1976-03-01 | ２−ピロリドンの製造方法 |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS6056707B2 (enExample) |
| BE (1) | BE839091A (enExample) |
| DE (1) | DE2609209C2 (enExample) |
| FR (1) | FR2303003A1 (enExample) |
| GB (1) | GB1494454A (enExample) |
| IT (1) | IT1057926B (enExample) |
| NL (1) | NL184953C (enExample) |
| SU (1) | SU585809A3 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3966763A (en) * | 1975-06-30 | 1976-06-29 | Standard Oil Company | Process for producing 2-pyrrolidone |
| NL7704179A (nl) * | 1977-04-18 | 1978-10-20 | Stamicarbon | Werkwijze voor de bereiding van n-gesubstitu- eerde 2-pyrrolidonen. |
| US6680331B2 (en) | 2001-07-16 | 2004-01-20 | Board Of Regents, The University Of Texas System | Lactam and thiolactam derivatives as anesthetic and conscious sedation agents |
| GB201709297D0 (en) * | 2017-06-12 | 2017-07-26 | Rheinisch-Westfälische Technische Hochschule (Rwth) Aachen | Method for preparing methylprrolidones |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3095423A (en) * | 1961-02-01 | 1963-06-25 | Minnesota Mining & Mfg | Synthesis of 2-pyrrolidinone |
| DE1923063B2 (de) * | 1968-05-16 | 1974-07-25 | Sumitomo Chemical Co., Ltd., Osaka (Japan) | Verfahren zur Herstellung von alpha-Pyrrolidon |
-
1975
- 1975-03-05 NL NL7502574A patent/NL184953C/xx not_active IP Right Cessation
-
1976
- 1976-02-23 GB GB704576A patent/GB1494454A/en not_active Expired
- 1976-03-01 JP JP2204676A patent/JPS6056707B2/ja not_active Expired
- 1976-03-02 BE BE164771A patent/BE839091A/xx not_active IP Right Cessation
- 1976-03-03 SU SU762328357A patent/SU585809A3/ru active
- 1976-03-03 IT IT4839676A patent/IT1057926B/it active
- 1976-03-03 FR FR7605972A patent/FR2303003A1/fr active Granted
- 1976-03-05 DE DE19762609209 patent/DE2609209C2/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SU585809A3 (ru) | 1977-12-25 |
| DE2609209C2 (de) | 1985-08-08 |
| NL184953B (nl) | 1989-07-17 |
| JPS51110560A (ja) | 1976-09-30 |
| NL184953C (nl) | 1989-12-18 |
| FR2303003A1 (fr) | 1976-10-01 |
| IT1057926B (it) | 1982-03-30 |
| NL7502574A (nl) | 1976-09-07 |
| GB1494454A (en) | 1977-12-07 |
| FR2303003B1 (enExample) | 1980-04-18 |
| DE2609209A1 (de) | 1976-09-16 |
| BE839091A (nl) | 1976-09-02 |
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