CA1101429A - Process for preparing 2-pyrrolidone - Google Patents
Process for preparing 2-pyrrolidoneInfo
- Publication number
- CA1101429A CA1101429A CA319,684A CA319684A CA1101429A CA 1101429 A CA1101429 A CA 1101429A CA 319684 A CA319684 A CA 319684A CA 1101429 A CA1101429 A CA 1101429A
- Authority
- CA
- Canada
- Prior art keywords
- catalyst
- succinonitrile
- hydrogenation
- ammonia
- process according
- 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 abstract description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000003054 catalyst Substances 0.000 claims abstract description 21
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 15
- IAHFWCOBPZCAEA-UHFFFAOYSA-N succinonitrile Chemical compound N#CCCC#N IAHFWCOBPZCAEA-UHFFFAOYSA-N 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 7
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 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
- 238000001816 cooling Methods 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/267—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7800644A NL7800644A (nl) | 1978-01-19 | 1978-01-19 | Werkwijze voor de bereiding van 2-pyrrolidon. |
| NL7800644 | 1978-01-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1101429A true CA1101429A (en) | 1981-05-19 |
Family
ID=19830180
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA319,684A Expired CA1101429A (en) | 1978-01-19 | 1979-01-16 | Process for preparing 2-pyrrolidone |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4193925A (en, 2012) |
| JP (1) | JPS54112858A (en, 2012) |
| BE (1) | BE873470A (en, 2012) |
| CA (1) | CA1101429A (en, 2012) |
| DE (1) | DE2901912A1 (en, 2012) |
| ES (1) | ES476964A1 (en, 2012) |
| FR (1) | FR2415100A1 (en, 2012) |
| GB (1) | GB2012748B (en, 2012) |
| IT (1) | IT1114715B (en, 2012) |
| NL (1) | NL7800644A (en, 2012) |
| SU (1) | SU942591A3 (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7902537A (nl) * | 1979-04-01 | 1980-10-03 | Stamicarbon | Werkwijze voor de bereiding van een eventueel c-gesubstitueerd 2-pyrrolidon en daarbij te gebruiken katalysator. |
| NL7909230A (nl) | 1979-12-21 | 1981-07-16 | Stamicarbon | Werkwijze voor het bereiden van een 2-pyrrolidon. |
| CA2447618A1 (en) * | 2001-05-23 | 2002-11-28 | Tanabe Seiyaku Co., Ltd. | A composition for regenerative treatment of cartilage disease |
| RU2379298C2 (ru) * | 2004-05-17 | 2010-01-20 | Оцука Фармасьютикал Ко., Лтд. | Соединение тиазола и его применение |
| US8728775B2 (en) | 2010-09-30 | 2014-05-20 | Daesang Corporation | Method for preparing 2-pyrrolidone using a microorganism containing glutamate decarboxylase |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4123438A (en) * | 1975-03-05 | 1978-10-31 | Stamicarbon, B.V. | Process for preparing 2-pyrrolidones |
-
1978
- 1978-01-19 NL NL7800644A patent/NL7800644A/xx not_active Application Discontinuation
-
1979
- 1979-01-12 GB GB791179A patent/GB2012748B/en not_active Expired
- 1979-01-15 BE BE0/192889A patent/BE873470A/xx not_active IP Right Cessation
- 1979-01-16 CA CA319,684A patent/CA1101429A/en not_active Expired
- 1979-01-17 IT IT47685/79A patent/IT1114715B/it active
- 1979-01-17 FR FR7901088A patent/FR2415100A1/fr active Granted
- 1979-01-18 JP JP443479A patent/JPS54112858A/ja active Granted
- 1979-01-18 ES ES476964A patent/ES476964A1/es not_active Expired
- 1979-01-18 DE DE19792901912 patent/DE2901912A1/de active Granted
- 1979-01-18 US US06/004,474 patent/US4193925A/en not_active Expired - Lifetime
- 1979-01-19 SU SU792712904A patent/SU942591A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| GB2012748B (en) | 1982-04-28 |
| GB2012748A (en) | 1979-08-01 |
| FR2415100B1 (en, 2012) | 1983-07-22 |
| IT1114715B (it) | 1986-01-27 |
| IT7947685A0 (it) | 1979-01-17 |
| BE873470A (nl) | 1979-07-16 |
| US4193925A (en) | 1980-03-18 |
| ES476964A1 (es) | 1979-06-16 |
| NL7800644A (nl) | 1979-07-23 |
| DE2901912C2 (en, 2012) | 1987-12-10 |
| DE2901912A1 (de) | 1979-07-26 |
| FR2415100A1 (fr) | 1979-08-17 |
| JPS6339586B2 (en, 2012) | 1988-08-05 |
| SU942591A3 (ru) | 1982-07-07 |
| JPS54112858A (en) | 1979-09-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |