DE1211165B - Verfahren zur Herstellung von Additions-produkten aus Halogensulfonylisocyanaten und Olefinen - Google Patents
Verfahren zur Herstellung von Additions-produkten aus Halogensulfonylisocyanaten und OlefinenInfo
- Publication number
- DE1211165B DE1211165B DEF42218A DEF0042218A DE1211165B DE 1211165 B DE1211165 B DE 1211165B DE F42218 A DEF42218 A DE F42218A DE F0042218 A DEF0042218 A DE F0042218A DE 1211165 B DE1211165 B DE 1211165B
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- isocyanate
- olefins
- halosulfonyl
- isocyanates
- 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 12
- 150000001336 alkenes Chemical class 0.000 title claims description 6
- -1 halogen sulfonyl isocyanates Chemical class 0.000 title description 10
- 238000004519 manufacturing process Methods 0.000 title description 2
- 229910052736 halogen Inorganic materials 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 239000000460 chlorine Substances 0.000 claims description 15
- 239000012948 isocyanate Substances 0.000 claims description 11
- 150000002513 isocyanates Chemical class 0.000 claims description 11
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 10
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 16
- 238000009835 boiling Methods 0.000 description 14
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 11
- 239000005977 Ethylene Substances 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- GIWHJVQUZDWFDI-UHFFFAOYSA-N 2-chloro-n-(oxomethylidene)ethanesulfonamide Chemical compound ClCCS(=O)(=O)N=C=O GIWHJVQUZDWFDI-UHFFFAOYSA-N 0.000 description 7
- UBDFKJIATGGYRZ-UHFFFAOYSA-N 4-chloro-N-(oxomethylidene)butane-1-sulfonamide Chemical compound ClCCCCS(=O)(=O)N=C=O UBDFKJIATGGYRZ-UHFFFAOYSA-N 0.000 description 6
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 5
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000004508 fractional distillation Methods 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- ZOLLIQAKMYWTBR-MOLCZBCNSA-N (1z,5z,9z)-cyclododeca-1,5,9-triene Chemical compound C\1C\C=C/CC\C=C/CC\C=C/1 ZOLLIQAKMYWTBR-MOLCZBCNSA-N 0.000 description 1
- QYCGBAJADAGLLK-UHFFFAOYSA-N 1-(cyclohepten-1-yl)cycloheptene Chemical compound C1CCCCC=C1C1=CCCCCC1 QYCGBAJADAGLLK-UHFFFAOYSA-N 0.000 description 1
- KAJRUHJCBCZULP-UHFFFAOYSA-N 1-cyclohepta-1,3-dien-1-ylcyclohepta-1,3-diene Chemical compound C1CCC=CC=C1C1=CC=CCCC1 KAJRUHJCBCZULP-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- ZZVWTHZHAHOJCC-UHFFFAOYSA-N 2,4-dioxoazetidine-3-sulfonic acid Chemical class S(=O)(=O)(O)C1C(=O)NC1=O ZZVWTHZHAHOJCC-UHFFFAOYSA-N 0.000 description 1
- SQJVNAUBKKVIFI-UHFFFAOYSA-N 3-chloro-n-(oxomethylidene)propane-1-sulfonamide Chemical compound ClCCCS(=O)(=O)N=C=O SQJVNAUBKKVIFI-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 1
- 239000004913 cyclooctene Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- AHAREKHAZNPPMI-UHFFFAOYSA-N hexa-1,3-diene Chemical compound CCC=CC=C AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- WPHGSKGZRAQSGP-UHFFFAOYSA-N methylenecyclohexane Natural products C1CCCC2CC21 WPHGSKGZRAQSGP-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000004753 textile Substances 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
- C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF42218A DE1211165B (de) | 1964-03-06 | 1964-03-06 | Verfahren zur Herstellung von Additions-produkten aus Halogensulfonylisocyanaten und Olefinen |
| US436655A US3266717A (en) | 1964-03-06 | 1965-03-02 | Addition products from halogenosulfonyl-isocyanates and olefins and process for preparing them |
| CH292065A CH470371A (de) | 1964-03-06 | 1965-03-03 | Verfahren zur Herstellung von Additionsprodukten aus Halogensulfonylisocyanaten und Olefinen |
| NL656502822A NL147422B (nl) | 1964-03-06 | 1965-03-05 | Werkwijze voor het bereiden van reactieprodukten uit chloorsulfonylisocyanaat en alkeenverbindingen. |
| GB9513/65A GB1102798A (en) | 1964-03-06 | 1965-03-05 | Addition products from halogenosulphonyl-isocyanates and olefines and a process for their preparation |
| FR8230A FR1427367A (fr) | 1964-03-06 | 1965-03-06 | Produits d'addition d'isocyanates d'halogénosulfonyles et d'oléfines et leur préparation |
| BE660782A BE660782A (OSRAM) | 1964-03-06 | 1965-03-08 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF42218A DE1211165B (de) | 1964-03-06 | 1964-03-06 | Verfahren zur Herstellung von Additions-produkten aus Halogensulfonylisocyanaten und Olefinen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1211165B true DE1211165B (de) | 1966-02-24 |
Family
ID=7098993
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF42218A Pending DE1211165B (de) | 1964-03-06 | 1964-03-06 | Verfahren zur Herstellung von Additions-produkten aus Halogensulfonylisocyanaten und Olefinen |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3266717A (OSRAM) |
| BE (1) | BE660782A (OSRAM) |
| CH (1) | CH470371A (OSRAM) |
| DE (1) | DE1211165B (OSRAM) |
| GB (1) | GB1102798A (OSRAM) |
| NL (1) | NL147422B (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2594543A1 (fr) * | 1986-02-20 | 1987-08-21 | Gaz De France | Procede et dispositif de controle d'une interface entre deux fluides non miscibles et de densites differentes |
-
1964
- 1964-03-06 DE DEF42218A patent/DE1211165B/de active Pending
-
1965
- 1965-03-02 US US436655A patent/US3266717A/en not_active Expired - Lifetime
- 1965-03-03 CH CH292065A patent/CH470371A/de not_active IP Right Cessation
- 1965-03-05 NL NL656502822A patent/NL147422B/xx not_active IP Right Cessation
- 1965-03-05 GB GB9513/65A patent/GB1102798A/en not_active Expired
- 1965-03-08 BE BE660782A patent/BE660782A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2594543A1 (fr) * | 1986-02-20 | 1987-08-21 | Gaz De France | Procede et dispositif de controle d'une interface entre deux fluides non miscibles et de densites differentes |
Also Published As
| Publication number | Publication date |
|---|---|
| BE660782A (OSRAM) | 1965-09-08 |
| GB1102798A (en) | 1968-02-07 |
| CH470371A (de) | 1969-03-31 |
| NL147422B (nl) | 1975-10-15 |
| US3266717A (en) | 1966-08-16 |
| NL6502822A (OSRAM) | 1965-09-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2330087C3 (de) | Verfahren zur Herstellung von 1,2-Diazacyclododecatrienen-(1,5,9) oder l^-Diazacyclododecaenen-d) | |
| DE2417985A1 (de) | Diolefindimerisierungskatalysatoren und verfahren zur katalytischen dimerisierung von diolefinen | |
| DE2512741A1 (de) | Verfahren zur herstellung von tricosen-(9) und heneicosen-(9) | |
| DE1211165B (de) | Verfahren zur Herstellung von Additions-produkten aus Halogensulfonylisocyanaten und Olefinen | |
| DE2131440A1 (de) | Verfahren zur Herstellung von Oxiranverbindungen durch Epoxydieren von Olefinen mit Hydroperoxiden | |
| DE1818048C2 (de) | Verfahren zur Herstellung von 5-Isopropyliden-2-norbornen durch Isomerisieren von 5-Isopropenyl-2-norbornen | |
| DE2613999C3 (de) | Verfahren zur Polymerisation von Cydoolefinen | |
| DE1910566C3 (de) | Verfahren zur Herstellung von 5-Alkenyl-2-norbornenen durch Diels-Alder-Reaktion von Cyclopentadien mit einem 4-Alkyl-13-butadien | |
| DE1493220C3 (de) | Verfahren zur katalytischen Ohgo mensation von 1,3 Diolefinen | |
| DE844442C (de) | Verfahren zur Herstellung von 1, 1-Dihalogen-1, 3-alkadienen | |
| DE2531959C3 (de) | Verfahren zur Herstellung von cis-7,8-Epoxy-2-methyloctadecan | |
| DE1810185B2 (de) | Nickel (0)-katalysatoren, Verfahren zu deren Herstellung und deren Verwendung zur Oligomerisation von Butadien | |
| DE1226565B (de) | Verfahren zur Herstellung von Additions-produkten aus Halogensulfonylisocyanaten undVinylchlorid | |
| DE977093C (de) | Verfahren zur Herstellung von [3, 4-Dihydro-ª‡-pyran(2)]-aethern und deren Derivaten | |
| DE1618401C3 (de) | Verfahren zur Herstellung von 2-Chlor-alkyl-isocyaniddichloriden neben Dichloralkanen | |
| DE2218451A1 (de) | Verfahren zur herstellung von fluoralkyljodidtelomeren der formel c tief n f tief 2n+1 -(cr tief 1 r tief 2) tief m - | |
| DE1618420B2 (de) | Verfahren zur herstellung von beta-brom- und beta-chloralkyl-isocyanaten | |
| DE1179932B (de) | Verfahren zur Herstellung von olefinisch ungesaettigten alicyclischen Polyhalogen-verbindungen | |
| DE1019307B (de) | Verfahren zur Herstellung von Epoxyverbindungen | |
| DE1238908B (de) | Verfahren zur Herstellung von Pentacyclo-(8, 2, 1, 1, 0, 0)-tetradecadien-(5, 11) | |
| DE2039818A1 (de) | Verfahren zur kontinuierlichen Herstellung von Bis(-aminocyclohexyl)-alkanen oder -aethern | |
| US3031464A (en) | Alkoxy-naphthalenes | |
| DE2326196C3 (de) | Verfahren zur Herstellung von reinem Cyclopenten | |
| DE2326836C3 (de) | Verfahren zur Durchführung der Diels-Alder-Reaktion | |
| DE1930329C3 (de) | Verfahren zur Herstellung von beta-Halogenalkyl-lsocyanaten |