CA1118712A - Process for preparing mercaptans - Google Patents
Process for preparing mercaptansInfo
- Publication number
- CA1118712A CA1118712A CA000329680A CA329680A CA1118712A CA 1118712 A CA1118712 A CA 1118712A CA 000329680 A CA000329680 A CA 000329680A CA 329680 A CA329680 A CA 329680A CA 1118712 A CA1118712 A CA 1118712A
- Authority
- CA
- Canada
- Prior art keywords
- alpha
- reaction
- ethylenically unsaturated
- carbon atoms
- hydrocarbon compound
- 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
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims abstract description 49
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 16
- 239000011541 reaction mixture Substances 0.000 claims abstract description 11
- 150000008062 acetophenones Chemical class 0.000 claims abstract description 9
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 8
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims abstract description 7
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- -1 alpha-propoxy Chemical group 0.000 claims description 13
- 230000005855 radiation Effects 0.000 claims description 12
- 239000000376 reactant Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 7
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 claims description 7
- CRPUJAZIXJMDBK-UHFFFAOYSA-N camphene Chemical compound C1CC2C(=C)C(C)(C)C1C2 CRPUJAZIXJMDBK-UHFFFAOYSA-N 0.000 claims description 6
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 6
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- GRWFGVWFFZKLTI-UHFFFAOYSA-N α-pinene Chemical compound CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- WTARULDDTDQWMU-RKDXNWHRSA-N (+)-β-pinene Chemical compound C1[C@H]2C(C)(C)[C@@H]1CCC2=C WTARULDDTDQWMU-RKDXNWHRSA-N 0.000 claims description 4
- WTARULDDTDQWMU-IUCAKERBSA-N (-)-Nopinene Natural products C1[C@@H]2C(C)(C)[C@H]1CCC2=C WTARULDDTDQWMU-IUCAKERBSA-N 0.000 claims description 4
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 4
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 claims description 4
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical group CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 claims description 4
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical group C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 claims description 4
- BBDKZWKEPDTENS-UHFFFAOYSA-N 4-Vinylcyclohexene Chemical compound C=CC1CCC=CC1 BBDKZWKEPDTENS-UHFFFAOYSA-N 0.000 claims description 4
- WTARULDDTDQWMU-UHFFFAOYSA-N Pseudopinene Natural products C1C2C(C)(C)C1CCC2=C WTARULDDTDQWMU-UHFFFAOYSA-N 0.000 claims description 4
- 229930006722 beta-pinene Natural products 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 claims description 4
- LCWMKIHBLJLORW-UHFFFAOYSA-N gamma-carene Natural products C1CC(=C)CC2C(C)(C)C21 LCWMKIHBLJLORW-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 claims description 4
- FAMJUFMHYAFYNU-JTQLQIEISA-N (4r)-1-methyl-4-propan-2-ylcyclohexene Chemical compound CC(C)[C@@H]1CCC(C)=CC1 FAMJUFMHYAFYNU-JTQLQIEISA-N 0.000 claims description 3
- WUOACPNHFRMFPN-SECBINFHSA-N (S)-(-)-alpha-terpineol Chemical compound CC1=CC[C@@H](C(C)(C)O)CC1 WUOACPNHFRMFPN-SECBINFHSA-N 0.000 claims description 3
- GRWFGVWFFZKLTI-IUCAKERBSA-N 1S,5S-(-)-alpha-Pinene Natural products CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 claims description 3
- PXRCIOIWVGAZEP-UHFFFAOYSA-N Primaeres Camphenhydrat Natural products C1CC2C(O)(C)C(C)(C)C1C2 PXRCIOIWVGAZEP-UHFFFAOYSA-N 0.000 claims description 3
- OVKDFILSBMEKLT-UHFFFAOYSA-N alpha-Terpineol Natural products CC(=C)C1(O)CCC(C)=CC1 OVKDFILSBMEKLT-UHFFFAOYSA-N 0.000 claims description 3
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 claims description 3
- 229940088601 alpha-terpineol Drugs 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 229930006739 camphene Natural products 0.000 claims description 3
- ZYPYEBYNXWUCEA-UHFFFAOYSA-N camphenilone Natural products C1CC2C(=O)C(C)(C)C1C2 ZYPYEBYNXWUCEA-UHFFFAOYSA-N 0.000 claims description 3
- LDLDYFCCDKENPD-UHFFFAOYSA-N ethenylcyclohexane Chemical compound C=CC1CCCCC1 LDLDYFCCDKENPD-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- WVAFEFUPWRPQSY-UHFFFAOYSA-N 1,2,3-tris(ethenyl)benzene Chemical compound C=CC1=CC=CC(C=C)=C1C=C WVAFEFUPWRPQSY-UHFFFAOYSA-N 0.000 claims description 2
- QWQFVUQPHUKAMY-UHFFFAOYSA-N 1,2-diphenyl-2-propoxyethanone Chemical compound C=1C=CC=CC=1C(OCCC)C(=O)C1=CC=CC=C1 QWQFVUQPHUKAMY-UHFFFAOYSA-N 0.000 claims description 2
- DZZAHLOABNWIFA-UHFFFAOYSA-N 2-butoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCCCC)C(=O)C1=CC=CC=C1 DZZAHLOABNWIFA-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims 2
- CTMHWPIWNRWQEG-UHFFFAOYSA-N 1-methylcyclohexene Chemical compound CC1=CCCCC1 CTMHWPIWNRWQEG-UHFFFAOYSA-N 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- OTKCEEWUXHVZQI-UHFFFAOYSA-N 1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)CC1=CC=CC=C1 OTKCEEWUXHVZQI-UHFFFAOYSA-N 0.000 claims 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 claims 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims 1
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 claims 1
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 claims 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 238000011084 recovery Methods 0.000 abstract description 2
- 150000001336 alkenes Chemical class 0.000 description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 6
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
- JMVZGKVGQDHWOI-UHFFFAOYSA-N 2-(2-methylpropoxy)-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC(C)C)C(=O)C1=CC=CC=C1 JMVZGKVGQDHWOI-UHFFFAOYSA-N 0.000 description 3
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000003504 photosensitizing agent Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 235000007586 terpenes Nutrition 0.000 description 2
- 125000000545 (4R)-limonene group Chemical group 0.000 description 1
- UPYPTOCXMIWHSG-UHFFFAOYSA-N 1-dodecylsulfanyldodecane Chemical compound CCCCCCCCCCCCSCCCCCCCCCCCC UPYPTOCXMIWHSG-UHFFFAOYSA-N 0.000 description 1
- GXGACIKXINYLAR-UHFFFAOYSA-N 2,2-dibutoxy-1-phenylethanone Chemical compound CCCCOC(OCCCC)C(=O)C1=CC=CC=C1 GXGACIKXINYLAR-UHFFFAOYSA-N 0.000 description 1
- LNBMZFHIYRDKNS-UHFFFAOYSA-N 2,2-dimethoxy-1-phenylethanone Chemical compound COC(OC)C(=O)C1=CC=CC=C1 LNBMZFHIYRDKNS-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- SUNXFMPZAFGPFW-UHFFFAOYSA-N 2-methyl-5-(1-sulfanylpropan-2-yl)cyclohexane-1-thiol Chemical compound SCC(C)C1CCC(C)C(S)C1 SUNXFMPZAFGPFW-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 238000010471 Markovnikov's rule Methods 0.000 description 1
- GVOIQSXBMLNCLC-UHFFFAOYSA-N OOOS Chemical compound OOOS GVOIQSXBMLNCLC-UHFFFAOYSA-N 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- 239000010453 quartz Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
- C07C319/04—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols by addition of hydrogen sulfide or its salts to unsaturated compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
- C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S204/00—Chemistry: electrical and wave energy
- Y10S204/902—Production of desired compound by wave energy in presence of a chemically designated nonreactant chemical treating agent, excluding water, chloroform, carbon tetrachloride, methylene chloride or benzene
- Y10S204/912—Oxygen treating agent
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/921,693 US4140604A (en) | 1978-07-03 | 1978-07-03 | Process for preparing mercaptans |
| US921,693 | 1978-07-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1118712A true CA1118712A (en) | 1982-02-23 |
Family
ID=25445834
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000329680A Expired CA1118712A (en) | 1978-07-03 | 1979-06-13 | Process for preparing mercaptans |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4140604A (https=) |
| JP (1) | JPS559087A (https=) |
| AR (1) | AR223978A1 (https=) |
| BE (1) | BE877402A (https=) |
| BR (1) | BR7904192A (https=) |
| CA (1) | CA1118712A (https=) |
| DE (1) | DE2926887C2 (https=) |
| ES (1) | ES482114A1 (https=) |
| FR (1) | FR2430417A1 (https=) |
| GB (1) | GB2024819B (https=) |
| IT (1) | IT1120460B (https=) |
| MX (1) | MX151516A (https=) |
| NL (1) | NL7905129A (https=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2608599B1 (fr) * | 1986-12-17 | 1989-03-31 | Elf Aquitaine | Synthese de dithiols |
| FR2627184B1 (fr) * | 1988-02-17 | 1990-07-13 | Elf Aquitaine | Procede de preparation de dithiols |
| FR2823206B1 (fr) * | 2001-04-05 | 2004-02-20 | Atofina | Procede photochimique semi-continu et dispositif pour sa mise en oeuvre |
| FR2866024A1 (fr) * | 2004-02-06 | 2005-08-12 | Arkema | Procede de fabrication de dodecylmercaptans. |
| CN101535245A (zh) * | 2006-10-17 | 2009-09-16 | 巴斯夫欧洲公司 | 将h2s加成到萜烯上以制备用于自由基聚合的新型分子量调节剂的方法 |
| CN101704772B (zh) * | 2009-11-19 | 2013-07-31 | 郑州大学 | 一种异丙硫醇的制备方法 |
| US8461293B2 (en) | 2010-08-03 | 2013-06-11 | Chevron Phillips Chemical Company Lp | Methods of mercaptanizing olefinic hydrocarbons and compositions produced therefrom |
| US20140131618A1 (en) | 2012-11-15 | 2014-05-15 | Chevron Phillips Chemical Company Lp | Methods of Mercaptanizing Unsaturated Compounds and Compositions Produced Therefrom |
| US20140221692A1 (en) * | 2013-02-04 | 2014-08-07 | Chevron Phillips Chemical Company Lp | Flow Reactor Vessels and Reactor Systems |
| US9522975B2 (en) | 2015-01-29 | 2016-12-20 | Chevron Phillips Chemical Company Lp | Mercaptanized vinylnorbornene compositions and methods of making same |
| US9447481B1 (en) | 2015-10-07 | 2016-09-20 | Chevron Phillips Chemical Company Lp | Dipentene dimercaptan compositions and use thereof as a mining chemical collector |
| US10189779B2 (en) | 2016-09-12 | 2019-01-29 | Chevron Phillips Chemical Company, Lp | Methods for producing thiol compounds and sulfide compounds using diphenylamine or a phenol compound |
| EP3992180B1 (en) * | 2020-10-29 | 2024-11-27 | Chevron Phillips Chemical Company LP | Methods for producing thiol compounds and sulfide compounds using a mono-alkyl phenol compound |
| CN119552100A (zh) * | 2025-01-23 | 2025-03-04 | 东营市海科瑞林化工有限公司 | 正十二烷基硫醇的制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2398481A (en) * | 1942-02-23 | 1946-04-16 | Shell Dev | Process for catalyzed abnormal addition reactions |
| US3050452A (en) * | 1960-08-08 | 1962-08-21 | Phillips Petroleum Co | Preparation of organic sulfur compounds |
| US3248315A (en) * | 1964-07-06 | 1966-04-26 | Phillips Petroleum Co | Thiol production |
| US3682804A (en) * | 1969-11-13 | 1972-08-08 | Dow Chemical Co | Method of preparing mercaptans using high energy radiation |
| US4052283A (en) * | 1974-12-23 | 1977-10-04 | Hooker Chemicals & Plastics Corporation | Sensitized production of sulfhydryl compounds using ultraviolet radiation |
| FR2424907A1 (fr) * | 1978-05-05 | 1979-11-30 | Elf Aquitaine | Perfectionnement a la synthese de mercaptans |
-
1978
- 1978-07-03 US US05/921,693 patent/US4140604A/en not_active Expired - Lifetime
-
1979
- 1979-06-13 CA CA000329680A patent/CA1118712A/en not_active Expired
- 1979-06-21 GB GB7921597A patent/GB2024819B/en not_active Expired
- 1979-06-28 IT IT49573/79A patent/IT1120460B/it active
- 1979-06-29 AR AR277126A patent/AR223978A1/es active
- 1979-07-02 BE BE0/196067A patent/BE877402A/xx not_active IP Right Cessation
- 1979-07-02 BR BR7904192A patent/BR7904192A/pt not_active IP Right Cessation
- 1979-07-02 NL NL7905129A patent/NL7905129A/nl not_active Application Discontinuation
- 1979-07-02 ES ES482114A patent/ES482114A1/es not_active Expired
- 1979-07-02 FR FR7917128A patent/FR2430417A1/fr active Granted
- 1979-07-02 MX MX178317A patent/MX151516A/es unknown
- 1979-07-02 JP JP8275979A patent/JPS559087A/ja active Granted
- 1979-07-03 DE DE2926887A patent/DE2926887C2/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| MX151516A (es) | 1984-12-06 |
| GB2024819B (en) | 1982-07-28 |
| IT7949573A0 (it) | 1979-06-28 |
| BE877402A (fr) | 1979-11-05 |
| GB2024819A (en) | 1980-01-16 |
| IT1120460B (it) | 1986-03-26 |
| ES482114A1 (es) | 1980-04-01 |
| US4140604A (en) | 1979-02-20 |
| JPS559087A (en) | 1980-01-22 |
| JPH024589B2 (https=) | 1990-01-29 |
| FR2430417B1 (https=) | 1983-12-09 |
| DE2926887A1 (de) | 1980-01-24 |
| DE2926887C2 (de) | 1988-05-26 |
| NL7905129A (nl) | 1980-01-07 |
| BR7904192A (pt) | 1980-03-25 |
| AR223978A1 (es) | 1981-10-15 |
| FR2430417A1 (fr) | 1980-02-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1118712A (en) | Process for preparing mercaptans | |
| Campbell | Synthesis of thioethers. Amide solvent-promoted nucleophilic displacement of halide by thiolate ion | |
| Trofimov et al. | Divinyl sulfide: Synthesis, properties, and applications | |
| Truce et al. | Addition of sulfonyl iodides to allenes | |
| Kharasch et al. | Carboxylation. 1 I. The Photochemical and Peroxide-catalyzed Reactions of Oxalyl Chloride with Paraffin Hydrocarbons2 | |
| Cristol et al. | Bridged Polycyclic Compounds. XXV. Free-Radical Addition of Benzenesulfonyl Halides to Norbornadiene1 | |
| Kolka et al. | Communications-The ortho-Alkylation of Phenols | |
| US3050452A (en) | Preparation of organic sulfur compounds | |
| JPS6256869B2 (https=) | ||
| EP0194348A2 (en) | Sulfinate-initiated addition of perfluorinated iodides to olefins | |
| Mahoney | Inhibition of Free-Radical Reactions. II. 1 Kinetic Study of the Reaction of Peroxy Radicals with Hydroquinones and Hindered Phenols | |
| Kobayashi et al. | Photolyses of Diaryl α-Disulfones | |
| Angus et al. | 150. Thiocyanogen chloride. Part I. Chemical evidence for the existence of the monomeric compound in solutions in organic solvents | |
| GILMAN et al. | Cleavage studies of some organogermanium compounds | |
| Kice et al. | The Thermal Decomposition of Thiolsulfonates1 | |
| EP1260500A1 (en) | Process for the production of a sulphur-containing organic compound | |
| US2572845A (en) | Alkylthiosulfenyl dithiocarbamates and preparation thereof | |
| US4764297A (en) | Protic solvent in a dehydrohalogenation process, the product obtained therefrom and lubricant compositions containing same | |
| US4040921A (en) | Process for beta-hydroxyalkylsulfoxides | |
| US3574697A (en) | Haloalkylene bisthiocyanates | |
| JPH03176435A (ja) | パーフルオロアルキルブロミドの合成 | |
| Scott et al. | Telomerization by Free Radical Mercaptan Chain Transfer. I. Styrene and Ethanethiol1 | |
| Takeuchi et al. | One-step arylthiolation to aromatic compounds by disulfide radical cations generated from oxidation of diaryl disulfides with aluminium chloride | |
| US2572567A (en) | Organic sulfenyl thiocyanates | |
| US3287417A (en) | Bis-(substituted thiol) dichloromethanes |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |