DE1230016B - Verfahren zur Herstellung von Alkenylsulfonylisocyanaten - Google Patents
Verfahren zur Herstellung von AlkenylsulfonylisocyanatenInfo
- Publication number
- DE1230016B DE1230016B DEF46161A DEF0046161A DE1230016B DE 1230016 B DE1230016 B DE 1230016B DE F46161 A DEF46161 A DE F46161A DE F0046161 A DEF0046161 A DE F0046161A DE 1230016 B DE1230016 B DE 1230016B
- Authority
- DE
- Germany
- Prior art keywords
- isocyanate
- benzene
- isocyanates
- torr
- reaction
- 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
- 239000012948 isocyanate Substances 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 11
- -1 alkenylsulfonyl isocyanates Chemical class 0.000 title claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 150000002513 isocyanates Chemical class 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000003701 inert diluent Substances 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 69
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 34
- 238000009835 boiling Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical class O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 description 6
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 6
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 4
- GIWHJVQUZDWFDI-UHFFFAOYSA-N 2-chloro-n-(oxomethylidene)ethanesulfonamide Chemical compound ClCCS(=O)(=O)N=C=O GIWHJVQUZDWFDI-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- VDOAVLAIDYVPLI-UHFFFAOYSA-N 2-chloro-n-(oxomethylidene)cyclohexane-1-sulfonamide Chemical compound ClC1CCCCC1S(=O)(=O)N=C=O VDOAVLAIDYVPLI-UHFFFAOYSA-N 0.000 description 2
- YIKXUAYVCQZXMZ-UHFFFAOYSA-N 2-chloro-n-(oxomethylidene)propane-1-sulfonamide Chemical compound CC(Cl)CS(=O)(=O)N=C=O YIKXUAYVCQZXMZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- FLNLIWYPUYNOOA-UHFFFAOYSA-N n-(oxomethylidene)ethenesulfonamide Chemical compound C=CS(=O)(=O)N=C=O FLNLIWYPUYNOOA-UHFFFAOYSA-N 0.000 description 2
- 150000003510 tertiary aliphatic amines Chemical class 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 125000005208 trialkylammonium group Chemical group 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- CTNGXWJRQKOEKH-UHFFFAOYSA-N 2,2-dichloro-n-(oxomethylidene)ethanesulfonamide Chemical compound ClC(Cl)CS(=O)(=O)N=C=O CTNGXWJRQKOEKH-UHFFFAOYSA-N 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- RHBUUZWMQBNLRP-UHFFFAOYSA-N 2-chloro-n-(oxomethylidene)butane-1-sulfonamide Chemical compound CCC(Cl)CS(=O)(=O)N=C=O RHBUUZWMQBNLRP-UHFFFAOYSA-N 0.000 description 1
- HPEPPPFDRRVEBZ-UHFFFAOYSA-N 2-chloro-n-(oxomethylidene)ethenesulfonamide Chemical compound ClC=CS(=O)(=O)N=C=O HPEPPPFDRRVEBZ-UHFFFAOYSA-N 0.000 description 1
- BVOBSNKPLMUHLK-UHFFFAOYSA-N 2-chloro-n-(oxomethylidene)hexane-1-sulfonamide Chemical compound CCCCC(Cl)CS(=O)(=O)N=C=O BVOBSNKPLMUHLK-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- IIFFFBSAXDNJHX-UHFFFAOYSA-N 2-methyl-n,n-bis(2-methylpropyl)propan-1-amine Chemical compound CC(C)CN(CC(C)C)CC(C)C IIFFFBSAXDNJHX-UHFFFAOYSA-N 0.000 description 1
- KVSHEPNCIKHBJZ-UHFFFAOYSA-N 3-chloro-n-(oxomethylidene)butane-2-sulfonamide Chemical compound CC(Cl)C(C)S(=O)(=O)N=C=O KVSHEPNCIKHBJZ-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical group C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005137 alkenylsulfonyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- ZOVDQJQJRGPRCO-UHFFFAOYSA-N n-(oxomethylidene)but-2-ene-2-sulfonamide Chemical compound CC=C(C)S(=O)(=O)N=C=O ZOVDQJQJRGPRCO-UHFFFAOYSA-N 0.000 description 1
- WAVUSALOADVQTJ-UHFFFAOYSA-N n-(oxomethylidene)butane-1-sulfonamide Chemical compound CCCCS(=O)(=O)N=C=O WAVUSALOADVQTJ-UHFFFAOYSA-N 0.000 description 1
- VIZRPNHLISQEMN-UHFFFAOYSA-N n-(oxomethylidene)propane-1-sulfonamide Chemical compound CCCS(=O)(=O)N=C=O VIZRPNHLISQEMN-UHFFFAOYSA-N 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- KLBOFRLEHJAXIU-UHFFFAOYSA-N tributylazanium;chloride Chemical compound Cl.CCCCN(CCCC)CCCC KLBOFRLEHJAXIU-UHFFFAOYSA-N 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyurethanes Or Polyureas (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF46161A DE1230016B (de) | 1965-05-26 | 1965-05-26 | Verfahren zur Herstellung von Alkenylsulfonylisocyanaten |
| NL6606966A NL6606966A (enrdf_load_stackoverflow) | 1965-05-26 | 1966-05-20 | |
| GB2290466A GB1146628A (en) | 1965-05-26 | 1966-05-23 | Alkenyl-sulphonyl isocyanates and process for preparing them |
| CH738266A CH474488A (de) | 1965-05-26 | 1966-05-23 | Verfahren zur Herstellung von gegebenenfalls substituierten Alkenyl- bzw. Cycloalkenyl-sulfonylisocyanaten |
| BE681637D BE681637A (enrdf_load_stackoverflow) | 1965-05-26 | 1966-05-26 | |
| FR63090A FR1481412A (fr) | 1965-05-26 | 1966-05-26 | Nouveaux isocyanates d'alcényl-sulfonyles et leur préparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF46161A DE1230016B (de) | 1965-05-26 | 1965-05-26 | Verfahren zur Herstellung von Alkenylsulfonylisocyanaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1230016B true DE1230016B (de) | 1966-12-08 |
Family
ID=7100877
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF46161A Pending DE1230016B (de) | 1965-05-26 | 1965-05-26 | Verfahren zur Herstellung von Alkenylsulfonylisocyanaten |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE681637A (enrdf_load_stackoverflow) |
| CH (1) | CH474488A (enrdf_load_stackoverflow) |
| DE (1) | DE1230016B (enrdf_load_stackoverflow) |
| GB (1) | GB1146628A (enrdf_load_stackoverflow) |
| NL (1) | NL6606966A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0053331A1 (de) * | 1980-11-28 | 1982-06-09 | Hoechst Aktiengesellschaft | Kontinuierliches Verfahren zur Herstellung von Chloralkylsulfonylisocyanaten |
| EP0073480A1 (de) * | 1981-09-01 | 1983-03-09 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von teilweise neuen 1,2-Dihalogenalkyl- und -cycloalkylsulfonylisocyanaten |
| EP0153646A3 (en) * | 1984-02-23 | 1985-12-11 | Hoechst Aktiengesellschaft | Process for preparing alkenylsulfonyl isocyanates |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4461640A (en) * | 1981-12-07 | 1984-07-24 | E. I. Du Pont De Nemours And Company | Herbicidal alkenyl sulfonamides |
-
1965
- 1965-05-26 DE DEF46161A patent/DE1230016B/de active Pending
-
1966
- 1966-05-20 NL NL6606966A patent/NL6606966A/xx unknown
- 1966-05-23 CH CH738266A patent/CH474488A/de not_active IP Right Cessation
- 1966-05-23 GB GB2290466A patent/GB1146628A/en not_active Expired
- 1966-05-26 BE BE681637D patent/BE681637A/xx unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0053331A1 (de) * | 1980-11-28 | 1982-06-09 | Hoechst Aktiengesellschaft | Kontinuierliches Verfahren zur Herstellung von Chloralkylsulfonylisocyanaten |
| US4375436A (en) | 1980-11-28 | 1983-03-01 | Hoechst Aktiengesellschaft | Continuous process for the production of chloroalkyl-sulfonyl isocyanates |
| EP0073480A1 (de) * | 1981-09-01 | 1983-03-09 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von teilweise neuen 1,2-Dihalogenalkyl- und -cycloalkylsulfonylisocyanaten |
| US4448731A (en) * | 1981-09-01 | 1984-05-15 | Hoechst Aktiengesellschaft | 1,2-Dihalogenoalkylsulfonyl isocyanates and 1,2-di-halogenocycloalkylsulfonyl isocyanates and process for their manufacture |
| EP0153646A3 (en) * | 1984-02-23 | 1985-12-11 | Hoechst Aktiengesellschaft | Process for preparing alkenylsulfonyl isocyanates |
Also Published As
| Publication number | Publication date |
|---|---|
| BE681637A (enrdf_load_stackoverflow) | 1966-11-28 |
| NL6606966A (enrdf_load_stackoverflow) | 1966-11-28 |
| CH474488A (de) | 1969-06-30 |
| GB1146628A (en) | 1969-03-26 |
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