DE2200600A1 - Verfahren zum Herstellen von Pyrrolidonen - Google Patents
Verfahren zum Herstellen von PyrrolidonenInfo
- Publication number
- DE2200600A1 DE2200600A1 DE19722200600 DE2200600A DE2200600A1 DE 2200600 A1 DE2200600 A1 DE 2200600A1 DE 19722200600 DE19722200600 DE 19722200600 DE 2200600 A DE2200600 A DE 2200600A DE 2200600 A1 DE2200600 A1 DE 2200600A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- anhydride
- ammonia
- amine
- hours
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 17
- 150000004040 pyrrolidinones Chemical class 0.000 title claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 29
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 15
- 229910021529 ammonia Inorganic materials 0.000 claims description 14
- 150000008064 anhydrides Chemical class 0.000 claims description 14
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 12
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 11
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 11
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 10
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 10
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 7
- 239000011976 maleic acid Substances 0.000 claims description 7
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- 239000001530 fumaric acid Substances 0.000 claims description 5
- 239000001384 succinic acid Substances 0.000 claims description 5
- 239000007858 starting material Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000003245 coal Substances 0.000 claims 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 12
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229940014800 succinic anhydride Drugs 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 240000007049 Juglans regia Species 0.000 description 1
- 235000009496 Juglans regia Nutrition 0.000 description 1
- 241000282376 Panthera tigris Species 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 150000003953 γ-lactams Chemical class 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10837671A | 1971-01-21 | 1971-01-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2200600A1 true DE2200600A1 (de) | 1972-08-10 |
Family
ID=22321862
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722200600 Pending DE2200600A1 (de) | 1971-01-21 | 1972-01-07 | Verfahren zum Herstellen von Pyrrolidonen |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE778261A (enExample) |
| CA (1) | CA943965A (enExample) |
| DE (1) | DE2200600A1 (enExample) |
| FR (1) | FR2122508B1 (enExample) |
| GB (1) | GB1336402A (enExample) |
| IT (1) | IT946461B (enExample) |
| NL (1) | NL7200682A (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0545150A1 (de) * | 1991-11-30 | 1993-06-09 | BASF Aktiengesellschaft | Verfahren zur Herstellung von N-substituierten Lactamen durch reduktive Aminierung von Dicarbonsäure-Derivaten mit gemischen primärer, sekundärer und tertiärer Amine |
| WO1993016042A1 (de) * | 1992-02-07 | 1993-08-19 | Akzo N.V. | Verfahren zur herstellung von pyrrolidon und n-alkylpyrrolidonen |
| EP0745589A1 (de) * | 1995-06-02 | 1996-12-04 | Bayer Ag | Verfahren zur Herstellung von 2-Pyrrolidonen |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2932456A1 (de) * | 1979-08-10 | 1981-02-26 | Chevron Res | Verfahren zur herstellung von 2-pyrrolidon |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1439192A (fr) * | 1965-04-07 | 1966-05-20 | Rhone Poulenc Sa | Procédé de préparation d'alpha-pyrrolidones nu-substituées |
-
1971
- 1971-11-02 CA CA126,666A patent/CA943965A/en not_active Expired
-
1972
- 1972-01-07 DE DE19722200600 patent/DE2200600A1/de active Pending
- 1972-01-11 IT IT1923372A patent/IT946461B/it active
- 1972-01-18 NL NL7200682A patent/NL7200682A/xx unknown
- 1972-01-19 FR FR7201665A patent/FR2122508B1/fr not_active Expired
- 1972-01-20 BE BE778261A patent/BE778261A/xx unknown
- 1972-01-21 GB GB298572A patent/GB1336402A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0545150A1 (de) * | 1991-11-30 | 1993-06-09 | BASF Aktiengesellschaft | Verfahren zur Herstellung von N-substituierten Lactamen durch reduktive Aminierung von Dicarbonsäure-Derivaten mit gemischen primärer, sekundärer und tertiärer Amine |
| US5276165A (en) * | 1991-11-30 | 1994-01-04 | Basf Aktiengesellschaft | Preparation of N-substituted lactams |
| WO1993016042A1 (de) * | 1992-02-07 | 1993-08-19 | Akzo N.V. | Verfahren zur herstellung von pyrrolidon und n-alkylpyrrolidonen |
| US5478950A (en) * | 1992-02-07 | 1995-12-26 | Akzo Nobel N.V. | Process for producing pyrrolidone and N-alkyl pyrrolidones |
| EP0745589A1 (de) * | 1995-06-02 | 1996-12-04 | Bayer Ag | Verfahren zur Herstellung von 2-Pyrrolidonen |
| US5912358A (en) * | 1995-06-02 | 1999-06-15 | Bayer Aktiengesellschaft | Process for preparing 2-pyrrolidones |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2122508B1 (enExample) | 1977-04-01 |
| CA943965A (en) | 1974-03-19 |
| GB1336402A (en) | 1973-11-07 |
| BE778261A (fr) | 1972-07-20 |
| NL7200682A (enExample) | 1972-07-25 |
| FR2122508A1 (enExample) | 1972-09-01 |
| IT946461B (it) | 1973-05-21 |
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