DE1770502A1 - Die Herstellung von epsilon,epsilon'-bis(epsilon-Caprolactam) - Google Patents
Die Herstellung von epsilon,epsilon'-bis(epsilon-Caprolactam)Info
- Publication number
- DE1770502A1 DE1770502A1 DE19681770502 DE1770502A DE1770502A1 DE 1770502 A1 DE1770502 A1 DE 1770502A1 DE 19681770502 DE19681770502 DE 19681770502 DE 1770502 A DE1770502 A DE 1770502A DE 1770502 A1 DE1770502 A1 DE 1770502A1
- Authority
- DE
- Germany
- Prior art keywords
- caprolactam
- peroxide
- epsilon
- bis
- molar ratio
- 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
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 title description 21
- 238000004519 manufacturing process Methods 0.000 title description 4
- 150000002978 peroxides Chemical class 0.000 claims description 19
- -1 hydrocarbon peroxide Chemical class 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 7
- 238000006471 dimerization reaction Methods 0.000 claims description 6
- 150000003951 lactams Chemical class 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- QPJCYJIZFCJYIR-UHFFFAOYSA-N 4-propylazetidin-2-one Chemical compound CCCC1CC(=O)N1 QPJCYJIZFCJYIR-UHFFFAOYSA-N 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- PAOHAQSLJSMLAT-UHFFFAOYSA-N 1-butylperoxybutane Chemical compound CCCCOOCCCC PAOHAQSLJSMLAT-UHFFFAOYSA-N 0.000 description 2
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 2
- FOAUQQDOLGYUFX-UHFFFAOYSA-N 7,8,15,16-tetraoxadispiro[5.2.5^{9}.2^{6}]hexadecane Chemical compound C1CCCCC21OOC1(CCCCC1)OO2 FOAUQQDOLGYUFX-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- SRSFOMHQIATOFV-UHFFFAOYSA-N octanoyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(=O)CCCCCCC SRSFOMHQIATOFV-UHFFFAOYSA-N 0.000 description 2
- BTLSLHNLDQCWKS-UHFFFAOYSA-N oxocan-2-one Chemical compound O=C1CCCCCCO1 BTLSLHNLDQCWKS-UHFFFAOYSA-N 0.000 description 2
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 2
- BIISIZOQPWZPPS-UHFFFAOYSA-N 2-tert-butylperoxypropan-2-ylbenzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC=C1 BIISIZOQPWZPPS-UHFFFAOYSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- ZCMUTXVQMSILSV-UHFFFAOYSA-N 3-diazo-2-methylpropanenitrile Chemical compound N#CC(C)C=[N+]=[N-] ZCMUTXVQMSILSV-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 150000002976 peresters Chemical class 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings 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
- C07D223/08—Oxygen atoms
- C07D223/10—Oxygen atoms attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL6707400A NL6707400A (cg-RX-API-DMAC7.html) | 1967-05-27 | 1967-05-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1770502A1 true DE1770502A1 (de) | 1971-11-11 |
Family
ID=19800243
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681770502 Pending DE1770502A1 (de) | 1967-05-27 | 1968-05-27 | Die Herstellung von epsilon,epsilon'-bis(epsilon-Caprolactam) |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3541081A (cg-RX-API-DMAC7.html) |
| BE (1) | BE715708A (cg-RX-API-DMAC7.html) |
| DE (1) | DE1770502A1 (cg-RX-API-DMAC7.html) |
| FR (1) | FR1573304A (cg-RX-API-DMAC7.html) |
| GB (1) | GB1201514A (cg-RX-API-DMAC7.html) |
| NL (1) | NL6707400A (cg-RX-API-DMAC7.html) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1521938A (fr) * | 1966-05-05 | 1968-04-19 | Stamicarbon | Préparations d'epsilon, epsilon'-bis (epsilon-caprolactame) et de polyamide à partir de celui-ci |
-
1967
- 1967-05-27 NL NL6707400A patent/NL6707400A/xx unknown
-
1968
- 1968-05-27 DE DE19681770502 patent/DE1770502A1/de active Pending
- 1968-05-27 GB GB25354/68A patent/GB1201514A/en not_active Expired
- 1968-05-27 BE BE715708D patent/BE715708A/xx unknown
- 1968-05-27 FR FR1573304D patent/FR1573304A/fr not_active Expired
- 1968-05-27 US US732039A patent/US3541081A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FR1573304A (cg-RX-API-DMAC7.html) | 1969-07-04 |
| BE715708A (cg-RX-API-DMAC7.html) | 1968-11-27 |
| NL6707400A (cg-RX-API-DMAC7.html) | 1968-11-28 |
| US3541081A (en) | 1970-11-17 |
| GB1201514A (en) | 1970-08-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHW | Rejection |