FR2467197A1 - Procede de preparation de sulfones insaturees et sulfones obtenues - Google Patents
Procede de preparation de sulfones insaturees et sulfones obtenues Download PDFInfo
- Publication number
- FR2467197A1 FR2467197A1 FR7925319A FR7925319A FR2467197A1 FR 2467197 A1 FR2467197 A1 FR 2467197A1 FR 7925319 A FR7925319 A FR 7925319A FR 7925319 A FR7925319 A FR 7925319A FR 2467197 A1 FR2467197 A1 FR 2467197A1
- Authority
- FR
- France
- Prior art keywords
- sulfones
- radical
- mmol
- palladium
- formula
- 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.)
- Granted
Links
- 150000003457 sulfones Chemical class 0.000 title claims abstract description 39
- 238000000034 method Methods 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title abstract description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 42
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 18
- 239000003054 catalyst Substances 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 34
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical group C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 19
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 13
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Natural products CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 13
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- UAHWPYUMFXYFJY-UHFFFAOYSA-N beta-myrcene Natural products CC(C)=CCCC(=C)C=C UAHWPYUMFXYFJY-UHFFFAOYSA-N 0.000 claims description 9
- 150000001993 dienes Chemical class 0.000 claims description 9
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 9
- DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 claims description 8
- 238000006317 isomerization reaction Methods 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 6
- VYBREYKSZAROCT-UHFFFAOYSA-N alpha-myrcene Natural products CC(=C)CCCC(=C)C=C VYBREYKSZAROCT-UHFFFAOYSA-N 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims 1
- -1 diene compound Chemical class 0.000 abstract description 34
- 239000000543 intermediate Substances 0.000 abstract description 2
- 235000019155 vitamin A Nutrition 0.000 abstract description 2
- 239000011719 vitamin A Substances 0.000 abstract description 2
- 235000019165 vitamin E Nutrition 0.000 abstract description 2
- 239000011709 vitamin E Substances 0.000 abstract description 2
- 238000006277 sulfonation reaction Methods 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 17
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
- 238000005481 NMR spectroscopy Methods 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 9
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- 229910052786 argon Inorganic materials 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000012047 saturated solution Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- KFZUDNZQQCWGKF-UHFFFAOYSA-M sodium;4-methylbenzenesulfinate Chemical compound [Na+].CC1=CC=C(S([O-])=O)C=C1 KFZUDNZQQCWGKF-UHFFFAOYSA-M 0.000 description 5
- 125000001174 sulfone group Chemical group 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000002350 geranyl group Chemical group [H]C([*])([H])/C([H])=C(C([H])([H])[H])/C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 3
- LAGGTOBQMQHXON-GGWOSOGESA-N (2e,6e)-octa-2,6-diene Chemical compound C\C=C\CC\C=C\C LAGGTOBQMQHXON-GGWOSOGESA-N 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 2
- TVIUAEWQBVNREF-UHFFFAOYSA-N 1-methyl-4-(2-methylbut-3-en-2-ylsulfonyl)benzene Chemical compound CC1=CC=C(S(=O)(=O)C(C)(C)C=C)C=C1 TVIUAEWQBVNREF-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- DILXLMRYFWFBGR-UHFFFAOYSA-N 2-formylbenzene-1,4-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(S(O)(=O)=O)C(C=O)=C1 DILXLMRYFWFBGR-UHFFFAOYSA-N 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- JEHKKBHWRAXMCH-UHFFFAOYSA-N benzenesulfinic acid Chemical compound O[S@@](=O)C1=CC=CC=C1 JEHKKBHWRAXMCH-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 150000002940 palladium Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- KHDBMTLGTSGEEG-UHFFFAOYSA-M sodium;2-methylbenzenesulfinate Chemical compound [Na+].CC1=CC=CC=C1S([O-])=O KHDBMTLGTSGEEG-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- PKTUARSWDKPPNE-IWGRKNQJSA-N (2e)-1-[(2e)-3,7-dimethylocta-2,6-dienyl]sulfonyl-3,7-dimethylocta-2,6-diene Chemical compound CC(C)=CCC\C(C)=C\CS(=O)(=O)C\C=C(/C)CCC=C(C)C PKTUARSWDKPPNE-IWGRKNQJSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- UVQPQWMBFCXVTR-UHFFFAOYSA-N 1-methyl-4-(4-methylphenyl)sulfonylsulfonylsulfonylbenzene Chemical class Cc1ccc(cc1)S(=O)(=O)S(=O)(=O)S(=O)(=O)c1ccc(C)cc1 UVQPQWMBFCXVTR-UHFFFAOYSA-N 0.000 description 1
- QTTZZUJXQPUOTF-UHFFFAOYSA-N 1-methyl-4-prop-2-enylsulfonylbenzene Chemical compound CC1=CC=C(S(=O)(=O)CC=C)C=C1 QTTZZUJXQPUOTF-UHFFFAOYSA-N 0.000 description 1
- MZPDTOMKQCMETI-UHFFFAOYSA-N 2,6-dimethylocta-2,6-diene Chemical compound CC=C(C)CCC=C(C)C MZPDTOMKQCMETI-UHFFFAOYSA-N 0.000 description 1
- FBHUMXQAXIGCHH-UHFFFAOYSA-N 3-methyl-1-(3-methylbut-2-enylsulfonyl)but-2-ene Chemical compound CC(C)=CCS(=O)(=O)CC=C(C)C FBHUMXQAXIGCHH-UHFFFAOYSA-N 0.000 description 1
- FXJVNINSOKCNJP-UHFFFAOYSA-M 4-methylbenzenesulfinate Chemical compound CC1=CC=C(S([O-])=O)C=C1 FXJVNINSOKCNJP-UHFFFAOYSA-M 0.000 description 1
- OUKZUIOFTUUCEN-UHFFFAOYSA-N 7$l^{6}-thiabicyclo[4.1.0]hepta-1,3,5-triene 7,7-dioxide Chemical compound C1=CC=C2S(=O)(=O)C2=C1 OUKZUIOFTUUCEN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- XLOPRKKSAJMMEW-SFYZADRCSA-N Chrysanthemic acid Natural products CC(C)=C[C@@H]1[C@@H](C(O)=O)C1(C)C XLOPRKKSAJMMEW-SFYZADRCSA-N 0.000 description 1
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 description 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000005137 alkenylsulfonyl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- JEHKKBHWRAXMCH-UHFFFAOYSA-M benzenesulfinate Chemical compound [O-]S(=O)C1=CC=CC=C1 JEHKKBHWRAXMCH-UHFFFAOYSA-M 0.000 description 1
- NVSONFIVLCXXDH-UHFFFAOYSA-N benzylsulfinic acid Chemical compound O[S@@](=O)CC1=CC=CC=C1 NVSONFIVLCXXDH-UHFFFAOYSA-N 0.000 description 1
- 238000005885 boration reaction Methods 0.000 description 1
- ZXZCCQGNKNBXMW-UHFFFAOYSA-N but-2-enylsulfonylbenzene Chemical compound CC=CCS(=O)(=O)C1=CC=CC=C1 ZXZCCQGNKNBXMW-UHFFFAOYSA-N 0.000 description 1
- NQSMHCACYCRLNI-UHFFFAOYSA-N but-3-en-2-ylsulfonylbenzene Chemical compound C=CC(C)S(=O)(=O)C1=CC=CC=C1 NQSMHCACYCRLNI-UHFFFAOYSA-N 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- XLOPRKKSAJMMEW-UHFFFAOYSA-N chrysanthemic acid Chemical compound CC(C)=CC1C(C(O)=O)C1(C)C XLOPRKKSAJMMEW-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- PRLFFGNMYPVCOW-UHFFFAOYSA-N ethyl 4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate Chemical compound C1CCCC2=C1SC=C2C(=O)OCC PRLFFGNMYPVCOW-UHFFFAOYSA-N 0.000 description 1
- 125000005469 ethylenyl group Chemical group 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229930002839 ionone Natural products 0.000 description 1
- 150000002499 ionone derivatives Chemical class 0.000 description 1
- WPHGSKGZRAQSGP-UHFFFAOYSA-N methylenecyclohexane Natural products C1CCCC2CC21 WPHGSKGZRAQSGP-UHFFFAOYSA-N 0.000 description 1
- ZOUWOGOTHLRRLS-UHFFFAOYSA-N palladium;phosphane Chemical compound P.[Pd] ZOUWOGOTHLRRLS-UHFFFAOYSA-N 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 1
- 150000004807 phenyl sulfones Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 101150035983 str1 gene Proteins 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Steroid Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7925319A FR2467197A1 (fr) | 1979-10-11 | 1979-10-11 | Procede de preparation de sulfones insaturees et sulfones obtenues |
| CA000361694A CA1159472A (fr) | 1979-10-11 | 1980-10-07 | Procede de preparation de sulfones insaturees et sulfones obtenues |
| US06/195,003 US4343952A (en) | 1979-10-11 | 1980-10-08 | Process for the preparation of unsaturated sulphones |
| JP14185080A JPS5686149A (en) | 1979-10-11 | 1980-10-09 | Manufacture of unsaturated sulfone and sulfone obtained thereby |
| AT80401457T ATE2139T1 (de) | 1979-10-11 | 1980-10-10 | Verfahren zur herstellung ungesaettigter sulfone und erhaltene sulfone. |
| DE8080401457T DE3061515D1 (en) | 1979-10-11 | 1980-10-10 | Process for the preparation of unsaturated sulphones, and sulphones obtained |
| EP80401457A EP0027421B1 (fr) | 1979-10-11 | 1980-10-10 | Procédé de préparation de sulfones insaturées et sulfones obtenues |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7925319A FR2467197A1 (fr) | 1979-10-11 | 1979-10-11 | Procede de preparation de sulfones insaturees et sulfones obtenues |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2467197A1 true FR2467197A1 (fr) | 1981-04-17 |
| FR2467197B1 FR2467197B1 (enExample) | 1984-01-27 |
Family
ID=9230579
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7925319A Granted FR2467197A1 (fr) | 1979-10-11 | 1979-10-11 | Procede de preparation de sulfones insaturees et sulfones obtenues |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4343952A (enExample) |
| EP (1) | EP0027421B1 (enExample) |
| JP (1) | JPS5686149A (enExample) |
| AT (1) | ATE2139T1 (enExample) |
| CA (1) | CA1159472A (enExample) |
| DE (1) | DE3061515D1 (enExample) |
| FR (1) | FR2467197A1 (enExample) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1425317A (fr) * | 1963-10-21 | 1966-01-24 | Yeda Res & Dev | Procédés pour la préparation de produits d'addition d'alcènes ou d'alcadiènes et de chlorure de sulfonyle et nouveaux produits ainsi obtenus |
| US3674856A (en) * | 1969-10-02 | 1972-07-04 | Raf Corp | Reaction of 1, 3-butadiene and organic sulfonyl halides |
| US3711516A (en) * | 1970-02-25 | 1973-01-16 | Zoecon Corp | Aliphatic ethers and thio compounds |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2427925A (en) * | 1944-10-10 | 1947-09-23 | Shell Dev | Diolefin production |
| US3267150A (en) * | 1963-08-12 | 1966-08-16 | Shell Oil Co | Sulfone production |
| US3397242A (en) * | 1965-10-15 | 1968-08-13 | Shell Oil Co | Sulfone production |
| BE794873A (fr) * | 1972-02-02 | 1973-08-01 | Rhone Poulenc Sa | Nouvelles sulfones a enchainement dimethyl-1,6 hexadien-1,5 ylene |
| BE794943A (fr) * | 1972-02-04 | 1973-08-02 | Rhone Poulenc Sa | Nouvelles sulfones methyleniques dans la serie des terpenes |
| FR2179499B1 (enExample) * | 1972-04-10 | 1977-08-05 | Rhone Poulenc Ind |
-
1979
- 1979-10-11 FR FR7925319A patent/FR2467197A1/fr active Granted
-
1980
- 1980-10-07 CA CA000361694A patent/CA1159472A/fr not_active Expired
- 1980-10-08 US US06/195,003 patent/US4343952A/en not_active Expired - Lifetime
- 1980-10-09 JP JP14185080A patent/JPS5686149A/ja active Pending
- 1980-10-10 DE DE8080401457T patent/DE3061515D1/de not_active Expired
- 1980-10-10 EP EP80401457A patent/EP0027421B1/fr not_active Expired
- 1980-10-10 AT AT80401457T patent/ATE2139T1/de not_active IP Right Cessation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1425317A (fr) * | 1963-10-21 | 1966-01-24 | Yeda Res & Dev | Procédés pour la préparation de produits d'addition d'alcènes ou d'alcadiènes et de chlorure de sulfonyle et nouveaux produits ainsi obtenus |
| US3674856A (en) * | 1969-10-02 | 1972-07-04 | Raf Corp | Reaction of 1, 3-butadiene and organic sulfonyl halides |
| US3711516A (en) * | 1970-02-25 | 1973-01-16 | Zoecon Corp | Aliphatic ethers and thio compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0027421B1 (fr) | 1982-12-29 |
| FR2467197B1 (enExample) | 1984-01-27 |
| US4343952A (en) | 1982-08-10 |
| JPS5686149A (en) | 1981-07-13 |
| EP0027421A1 (fr) | 1981-04-22 |
| CA1159472A (fr) | 1983-12-27 |
| ATE2139T1 (de) | 1983-01-15 |
| DE3061515D1 (en) | 1983-02-03 |
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