CA1038869A - Method for the production of omega lactams and their precursors by formation and nitrosation of the cyclomethylene ketene-so2 adduct and products obtained thereby - Google Patents
Method for the production of omega lactams and their precursors by formation and nitrosation of the cyclomethylene ketene-so2 adduct and products obtained therebyInfo
- Publication number
- CA1038869A CA1038869A CA162,227A CA162227A CA1038869A CA 1038869 A CA1038869 A CA 1038869A CA 162227 A CA162227 A CA 162227A CA 1038869 A CA1038869 A CA 1038869A
- Authority
- CA
- Canada
- Prior art keywords
- adduct
- excess
- solution
- cpmk
- liquid
- 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
- 238000000034 method Methods 0.000 title claims abstract description 25
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 21
- 239000002243 precursor Substances 0.000 title claims abstract description 17
- 150000003951 lactams Chemical class 0.000 title claims abstract description 8
- 238000007034 nitrosation reaction Methods 0.000 title claims description 15
- 230000009935 nitrosation Effects 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims abstract description 39
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 claims abstract description 16
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 claims abstract description 12
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims abstract 42
- 239000007788 liquid Substances 0.000 claims description 21
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 11
- 235000011149 sulphuric acid Nutrition 0.000 claims description 11
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000001117 sulphuric acid Substances 0.000 claims description 6
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 4
- 125000000018 nitroso group Chemical group N(=O)* 0.000 claims description 2
- 150000002923 oximes Chemical class 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- 230000001737 promoting effect Effects 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims 1
- 150000002832 nitroso derivatives Chemical class 0.000 claims 1
- TURAMGVWNUTQKH-UHFFFAOYSA-N propa-1,2-dien-1-one Chemical compound C=C=C=O TURAMGVWNUTQKH-UHFFFAOYSA-N 0.000 claims 1
- 230000002226 simultaneous effect Effects 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 8
- 239000006227 byproduct Substances 0.000 abstract description 6
- 239000003795 chemical substances by application Substances 0.000 abstract description 6
- 239000007858 starting material Substances 0.000 abstract description 3
- 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 abstract description 2
- 235000010269 sulphur dioxide Nutrition 0.000 abstract 1
- 239000004291 sulphur dioxide Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 20
- 239000002904 solvent Substances 0.000 description 15
- 238000007792 addition Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000000284 extract Substances 0.000 description 4
- 150000002561 ketenes Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- -1 alicyclic ketenes Chemical class 0.000 description 3
- 239000012670 alkaline solution Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-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 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000002826 coolant Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YBXJZGOTBMPKNO-UHFFFAOYSA-N 2-ethylhex-1-en-1-one Chemical compound CCCCC(CC)=C=O YBXJZGOTBMPKNO-UHFFFAOYSA-N 0.000 description 1
- VDOKWPVSGXHSNP-UHFFFAOYSA-N 2-methylprop-1-en-1-one Chemical compound CC(C)=C=O VDOKWPVSGXHSNP-UHFFFAOYSA-N 0.000 description 1
- 241000579895 Chlorostilbon Species 0.000 description 1
- GEVKLMCYASQZEN-UHFFFAOYSA-N N(=O)C1(CCCCC1)C(=O)O Chemical compound N(=O)C1(CCCCC1)C(=O)O GEVKLMCYASQZEN-UHFFFAOYSA-N 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 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 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000004320 controlled atmosphere Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229910052876 emerald Inorganic materials 0.000 description 1
- 239000010976 emerald Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- 238000012423 maintenance Methods 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
- 239000000178 monomer Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- YNGRGHODNDCZCC-UHFFFAOYSA-N nitro hydrogen sulfate Chemical compound OS(=O)(=O)O[N+]([O-])=O YNGRGHODNDCZCC-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000012546 transfer 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 |
|---|---|
| CA1038869A true CA1038869A (en) | 1978-09-19 |
Family
ID=11162033
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA162,227A Expired CA1038869A (en) | 1972-01-27 | 1973-01-26 | Method for the production of omega lactams and their precursors by formation and nitrosation of the cyclomethylene ketene-so2 adduct and products obtained thereby |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US3835124A (ref) |
| JP (1) | JPS4881884A (ref) |
| AR (1) | AR196751A1 (ref) |
| AT (1) | AT329580B (ref) |
| BE (1) | BE794509A (ref) |
| BR (1) | BR7300603D0 (ref) |
| CA (1) | CA1038869A (ref) |
| CH (1) | CH587212A5 (ref) |
| DD (1) | DD105613A1 (ref) |
| DE (1) | DE2303821A1 (ref) |
| DK (1) | DK139964B (ref) |
| ES (1) | ES410999A1 (ref) |
| FR (1) | FR2169246B1 (ref) |
| GB (1) | GB1411061A (ref) |
| IE (1) | IE37149B1 (ref) |
| IL (1) | IL41400A (ref) |
| IN (1) | IN140469B (ref) |
| IT (1) | IT954876B (ref) |
| NL (1) | NL7301166A (ref) |
| SE (1) | SE411544B (ref) |
| SU (1) | SU604484A3 (ref) |
| TR (1) | TR17480A (ref) |
| ZA (1) | ZA73151B (ref) |
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 DK DK41373AA patent/DK139964B/da unknown
- 1973-01-25 IL IL41400A patent/IL41400A/en unknown
- 1973-01-25 GB GB391673A patent/GB1411061A/en not_active Expired
- 1973-01-25 IN IN178/CAL/1973A patent/IN140469B/en unknown
- 1973-01-25 FR FR7302623A patent/FR2169246B1/fr not_active Expired
- 1973-01-26 DD DD168467A patent/DD105613A1/xx unknown
- 1973-01-26 ES ES410999A patent/ES410999A1/es not_active Expired
- 1973-01-26 IE IE133/73A patent/IE37149B1/xx unknown
- 1973-01-26 SU SU731878900A patent/SU604484A3/ru active
- 1973-01-26 NL NL7301166A patent/NL7301166A/xx not_active Application Discontinuation
- 1973-01-26 JP JP48010386A patent/JPS4881884A/ja active Pending
- 1973-01-26 BR BR73603A patent/BR7300603D0/pt unknown
- 1973-01-26 DE DE2303821A patent/DE2303821A1/de active Pending
- 1973-01-26 CA CA162,227A patent/CA1038869A/en not_active Expired
- 1973-01-29 AR AR246335A patent/AR196751A1/es active
-
1976
- 1976-02-26 SE SE7602498A patent/SE411544B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE411544B (sv) | 1980-01-14 |
| DE2303821A1 (de) | 1973-08-02 |
| CH587212A5 (ref) | 1977-04-29 |
| US3835124A (en) | 1974-09-10 |
| IN140469B (ref) | 1976-11-13 |
| IE37149B1 (en) | 1977-05-11 |
| GB1411061A (en) | 1975-10-22 |
| ATA55273A (de) | 1975-08-15 |
| IL41400A (en) | 1976-02-29 |
| FR2169246B1 (ref) | 1976-05-14 |
| IL41400A0 (en) | 1973-03-30 |
| DK139964B (da) | 1979-05-28 |
| DD105613A1 (ref) | 1974-05-05 |
| IE37149L (en) | 1973-07-27 |
| JPS4881884A (ref) | 1973-11-01 |
| IT954876B (it) | 1973-09-15 |
| BE794509A (fr) | 1973-07-25 |
| SE7602498L (sv) | 1976-02-26 |
| AU5098273A (en) | 1974-07-11 |
| AR196751A1 (es) | 1974-02-19 |
| ZA73151B (en) | 1973-09-26 |
| AT329580B (de) | 1976-05-25 |
| FR2169246A1 (ref) | 1973-09-07 |
| NL7301166A (ref) | 1973-07-31 |
| BR7300603D0 (pt) | 1973-09-13 |
| ES410999A1 (es) | 1975-12-01 |
| DK139964C (ref) | 1979-10-22 |
| SU604484A3 (ru) | 1978-04-25 |
| TR17480A (tr) | 1975-07-23 |
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