DE2303821A1 - Verfahren zur herstellung von omegalactamen und dazugehoerigen vorprodukten - Google Patents
Verfahren zur herstellung von omegalactamen und dazugehoerigen vorproduktenInfo
- Publication number
- DE2303821A1 DE2303821A1 DE2303821A DE2303821A DE2303821A1 DE 2303821 A1 DE2303821 A1 DE 2303821A1 DE 2303821 A DE2303821 A DE 2303821A DE 2303821 A DE2303821 A DE 2303821A DE 2303821 A1 DE2303821 A1 DE 2303821A1
- Authority
- DE
- Germany
- Prior art keywords
- solution
- cpmk
- adduct
- product
- ketene
- 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 27
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- 230000008569 process Effects 0.000 title claims description 12
- 239000000047 product Substances 0.000 claims description 36
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 11
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 claims description 10
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 claims description 9
- 239000002243 precursor Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 239000006227 byproduct Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 3
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 claims description 3
- 239000013067 intermediate product Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- FPIQZBQZKBKLEI-UHFFFAOYSA-N ethyl 1-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylate Chemical compound ClCCN(N=O)C(=O)NC1(C(=O)OCC)CCCCC1 FPIQZBQZKBKLEI-UHFFFAOYSA-N 0.000 claims 1
- 150000003951 lactams Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 238000007792 addition Methods 0.000 description 9
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 8
- 239000000284 extract Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000007034 nitrosation reaction Methods 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- -1 cyclic nitroso compounds Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000009935 nitrosation Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- NNBFNNNWANBMTI-UHFFFAOYSA-M brilliant green Chemical compound OS([O-])(=O)=O.C1=CC(N(CC)CC)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](CC)CC)C=C1 NNBFNNNWANBMTI-UHFFFAOYSA-M 0.000 description 2
- 238000004320 controlled atmosphere Methods 0.000 description 2
- 239000002826 coolant Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- KBYMQDYGNRTQBR-UHFFFAOYSA-N [S-][N+]=O Chemical compound [S-][N+]=O KBYMQDYGNRTQBR-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- ZWJPCOALBPMBIC-UHFFFAOYSA-N diphenylketene Chemical compound C=1C=CC=CC=1C(=C=O)C1=CC=CC=C1 ZWJPCOALBPMBIC-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- VFNGKCDDZUSWLR-UHFFFAOYSA-N disulfuric acid Chemical compound OS(=O)(=O)OS(O)(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002561 ketenes Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- LOOLOJCDYIZPTQ-UHFFFAOYSA-N nitrosin Natural products CC1C2C(CC3(C)CCCC(=C)C3(O)C2OC1=O)OC(=O)C LOOLOJCDYIZPTQ-UHFFFAOYSA-N 0.000 description 1
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000010792 warming 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
- C07D201/10—Preparation of lactams from cycloaliphatic compounds by simultaneous nitrosylation and rearrangement
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT19882/72A IT954876B (it) | 1972-01-27 | 1972-01-27 | Procedimento per la produzione di omega lattami e relativi pre cursori mediante formazione e ni trosazione dell addotto ciclometi lenchetene s02 e prodotti relativi |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2303821A1 true DE2303821A1 (de) | 1973-08-02 |
Family
ID=11162033
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2303821A Pending DE2303821A1 (de) | 1972-01-27 | 1973-01-26 | Verfahren zur herstellung von omegalactamen und dazugehoerigen vorprodukten |
Country Status (23)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102335573B (zh) * | 2010-07-23 | 2013-09-11 | 中国石油化工股份有限公司 | 一种己内酰胺苛化装置 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3733317A (en) * | 1970-06-30 | 1973-05-15 | Snia Viscosa | Method for the preparation of omega-lactams and their lactamizable precursors |
-
0
- BE BE794509D patent/BE794509A/xx unknown
-
1972
- 1972-01-27 IT IT19882/72A patent/IT954876B/it active
-
1973
- 1973-01-09 ZA ZA730151A patent/ZA73151B/xx unknown
- 1973-01-16 CH CH58073A patent/CH587212A5/xx not_active IP Right Cessation
- 1973-01-22 US US00325563A patent/US3835124A/en not_active Expired - Lifetime
- 1973-01-23 AT AT55273*#A patent/AT329580B/de not_active IP Right Cessation
- 1973-01-24 TR TR17480A patent/TR17480A/xx unknown
- 1973-01-25 IL IL41400A patent/IL41400A/en unknown
- 1973-01-25 IN IN178/CAL/1973A patent/IN140469B/en unknown
- 1973-01-25 GB GB391673A patent/GB1411061A/en not_active Expired
- 1973-01-25 FR FR7302623A patent/FR2169246B1/fr not_active Expired
- 1973-01-25 DK DK41373AA patent/DK139964B/da unknown
- 1973-01-26 NL NL7301166A patent/NL7301166A/xx not_active Application Discontinuation
- 1973-01-26 BR BR73603A patent/BR7300603D0/pt unknown
- 1973-01-26 JP JP48010386A patent/JPS4881884A/ja active Pending
- 1973-01-26 ES ES410999A patent/ES410999A1/es not_active Expired
- 1973-01-26 CA CA162,227A patent/CA1038869A/en not_active Expired
- 1973-01-26 DE DE2303821A patent/DE2303821A1/de active Pending
- 1973-01-26 SU SU731878900A patent/SU604484A3/ru active
- 1973-01-26 DD DD168467A patent/DD105613A1/xx unknown
- 1973-01-26 IE IE133/73A patent/IE37149B1/xx unknown
- 1973-01-29 AR AR246335A patent/AR196751A1/es active
-
1976
- 1976-02-26 SE SE7602498A patent/SE411544B/xx unknown
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |