CA1306466C - Oxidation of thiols, disulfides and thiosulfonates - Google Patents
Oxidation of thiols, disulfides and thiosulfonatesInfo
- Publication number
- CA1306466C CA1306466C CA000580671A CA580671A CA1306466C CA 1306466 C CA1306466 C CA 1306466C CA 000580671 A CA000580671 A CA 000580671A CA 580671 A CA580671 A CA 580671A CA 1306466 C CA1306466 C CA 1306466C
- Authority
- CA
- Canada
- Prior art keywords
- dialkyldisulfide
- moles
- alkanethiol
- hydrogen peroxide
- carbon atoms
- 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 - Lifetime
Links
- 238000007254 oxidation reaction Methods 0.000 title abstract description 13
- 230000003647 oxidation Effects 0.000 title abstract description 12
- 150000003573 thiols Chemical class 0.000 title description 3
- 150000002019 disulfides Chemical class 0.000 title description 2
- GWIKYPMLNBTJHR-UHFFFAOYSA-M thiosulfonate group Chemical group S(=S)(=O)[O-] GWIKYPMLNBTJHR-UHFFFAOYSA-M 0.000 title 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 60
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 54
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 28
- -1 alkanesulfonyl chlorides Chemical class 0.000 claims abstract description 19
- 239000002253 acid Substances 0.000 claims abstract description 14
- 150000007513 acids Chemical class 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 17
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 150000002978 peroxides Chemical class 0.000 claims description 3
- 239000000243 solution Substances 0.000 claims 8
- 239000007864 aqueous solution Substances 0.000 claims 4
- 238000005660 chlorination reaction Methods 0.000 abstract description 10
- 239000006227 byproduct Substances 0.000 abstract description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 239000011541 reaction mixture Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- ALVPFGSHPUPROW-UHFFFAOYSA-N dipropyl disulfide Chemical compound CCCSSCCC ALVPFGSHPUPROW-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CETBSQOFQKLHHZ-UHFFFAOYSA-N Diethyl disulfide Chemical compound CCSSCC CETBSQOFQKLHHZ-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- XYONNSVDNIRXKZ-UHFFFAOYSA-N S-methyl methanethiosulfonate Chemical compound CSS(C)(=O)=O XYONNSVDNIRXKZ-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- IDJPKRIELSFBPE-UHFFFAOYSA-N 1-(decyldisulfanyl)decane Chemical compound CCCCCCCCCCSSCCCCCCCCCC IDJPKRIELSFBPE-UHFFFAOYSA-N 0.000 description 1
- GJPDBURPGLWRPW-UHFFFAOYSA-N 1-(hexyldisulfanyl)hexane Chemical compound CCCCCCSSCCCCCC GJPDBURPGLWRPW-UHFFFAOYSA-N 0.000 description 1
- AROCLDYPZXMJPW-UHFFFAOYSA-N 1-(octyldisulfanyl)octane Chemical compound CCCCCCCCSSCCCCCCCC AROCLDYPZXMJPW-UHFFFAOYSA-N 0.000 description 1
- YSQZSPCQDXHJDJ-UHFFFAOYSA-N 1-(pentyldisulfanyl)pentane Chemical compound CCCCCSSCCCCC YSQZSPCQDXHJDJ-UHFFFAOYSA-N 0.000 description 1
- GPKDGVXBXQTHRY-UHFFFAOYSA-N 3-chloropropane-1-sulfonyl chloride Chemical compound ClCCCS(Cl)(=O)=O GPKDGVXBXQTHRY-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- CUDSBWGCGSUXDB-UHFFFAOYSA-N Dibutyl disulfide Chemical compound CCCCSSCCCC CUDSBWGCGSUXDB-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- LZAZXBXPKRULLB-UHFFFAOYSA-N Diisopropyl disulfide Chemical compound CC(C)SSC(C)C LZAZXBXPKRULLB-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- LOCHFZBWPCLPAN-UHFFFAOYSA-N butane-2-thiol Chemical compound CCC(C)S LOCHFZBWPCLPAN-UHFFFAOYSA-N 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
- 239000012043 crude product Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- KPBSJEBFALFJTO-UHFFFAOYSA-N propane-1-sulfonyl chloride Chemical compound CCCS(Cl)(=O)=O KPBSJEBFALFJTO-UHFFFAOYSA-N 0.000 description 1
- KJRCEJOSASVSRA-UHFFFAOYSA-N propane-2-thiol Chemical compound CC(C)S KJRCEJOSASVSRA-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11264887A | 1987-10-26 | 1987-10-26 | |
| US112,648 | 1987-10-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1306466C true CA1306466C (en) | 1992-08-18 |
Family
ID=22345106
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000580671A Expired - Lifetime CA1306466C (en) | 1987-10-26 | 1988-10-19 | Oxidation of thiols, disulfides and thiosulfonates |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0313939B1 (en, 2012) |
| JP (1) | JPH0272147A (en, 2012) |
| BR (1) | BR8805506A (en, 2012) |
| CA (1) | CA1306466C (en, 2012) |
| DE (1) | DE3874672T2 (en, 2012) |
| DK (1) | DK591788A (en, 2012) |
| ES (1) | ES2034094T3 (en, 2012) |
| IN (1) | IN171002B (en, 2012) |
| MX (1) | MX169407B (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5480993A (en) * | 1993-03-05 | 1996-01-02 | Lucky Ltd. | Process for preparation of sulfonylurea derivatives and intermediates for the process and process for preparing the same |
| JP3981430B2 (ja) * | 1997-01-20 | 2007-09-26 | 株式会社Ａｄｅｋａ | 純粋なアルカンスルホン酸の製造方法 |
| FR2841551B1 (fr) * | 2002-06-28 | 2006-01-13 | Rhodia Chimie Sa | Procede de synthese de derives a radical hydrogenofluoromethylene-sulfonyle |
| US7297813B2 (en) * | 2004-08-05 | 2007-11-20 | Arkema Inc. | Removal of alkyl alkanesulfonate esters from alkanesulfonic acids and other organic media |
| JP6149667B2 (ja) * | 2013-10-07 | 2017-06-21 | 日本軽金属株式会社 | スルホニルクロライド化合物類の製造方法 |
| WO2015086424A1 (en) | 2013-12-11 | 2015-06-18 | Evonik Industries Ag | A catalyst for oxidation reactions, a method for its preparation and the use thereof |
| CN118715202A (zh) | 2022-02-18 | 2024-09-27 | 巴斯夫欧洲公司 | 用于生产烷基磺酸的方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2667507A (en) * | 1950-08-31 | 1954-01-26 | Celanese Corp | Preparation of disulfonic acids |
| US3626004A (en) * | 1967-12-07 | 1971-12-07 | Pennwalt Corp | Method of preparing alkyl sulfonyl chloride |
| GB1524451A (en) * | 1975-02-01 | 1978-09-13 | Degussa | Process for the production of alkane sulphonic acids |
-
1988
- 1988-10-14 DE DE19883874672 patent/DE3874672T2/de not_active Expired - Fee Related
- 1988-10-14 EP EP19880117114 patent/EP0313939B1/en not_active Expired
- 1988-10-14 ES ES88117114T patent/ES2034094T3/es not_active Expired - Lifetime
- 1988-10-17 IN IN864/CAL/88A patent/IN171002B/en unknown
- 1988-10-19 CA CA000580671A patent/CA1306466C/en not_active Expired - Lifetime
- 1988-10-25 DK DK591788A patent/DK591788A/da not_active Application Discontinuation
- 1988-10-25 BR BR8805506A patent/BR8805506A/pt not_active Application Discontinuation
- 1988-10-25 MX MX1355888A patent/MX169407B/es unknown
- 1988-10-25 JP JP26733088A patent/JPH0272147A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ES2034094T3 (es) | 1993-04-01 |
| DE3874672D1 (de) | 1992-10-22 |
| DK591788D0 (da) | 1988-10-25 |
| EP0313939B1 (en) | 1992-09-16 |
| DE3874672T2 (de) | 1993-03-11 |
| MX169407B (es) | 1993-07-01 |
| EP0313939A3 (en) | 1989-07-12 |
| IN171002B (en, 2012) | 1992-06-27 |
| EP0313939A2 (en) | 1989-05-03 |
| DK591788A (da) | 1989-04-27 |
| JPH0272147A (ja) | 1990-03-12 |
| BR8805506A (pt) | 1989-07-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |