DE2450634A1 - Verfahren zur herstellung von organischen sulfoxiden - Google Patents
Verfahren zur herstellung von organischen sulfoxidenInfo
- Publication number
- DE2450634A1 DE2450634A1 DE19742450634 DE2450634A DE2450634A1 DE 2450634 A1 DE2450634 A1 DE 2450634A1 DE 19742450634 DE19742450634 DE 19742450634 DE 2450634 A DE2450634 A DE 2450634A DE 2450634 A1 DE2450634 A1 DE 2450634A1
- Authority
- DE
- Germany
- Prior art keywords
- sulfoxides
- solvent
- sulfoxide
- organic
- heptane
- 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
- 150000003462 sulfoxides Chemical class 0.000 title claims description 46
- 238000000034 method Methods 0.000 title claims description 17
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 claims description 31
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 17
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 13
- -1 preferably however Chemical compound 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000002537 cosmetic Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 230000003647 oxidation Effects 0.000 claims description 7
- 238000007254 oxidation reaction Methods 0.000 claims description 7
- 150000003568 thioethers Chemical class 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 239000006260 foam Substances 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 239000002453 shampoo Substances 0.000 claims description 6
- 239000002562 thickening agent Substances 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 5
- 239000003973 paint Substances 0.000 claims description 4
- 239000012429 reaction media Substances 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 239000006071 cream Substances 0.000 claims description 3
- OWXJKYNZGFSVRC-NSCUHMNNSA-N (e)-1-chloroprop-1-ene Chemical compound C\C=C\Cl OWXJKYNZGFSVRC-NSCUHMNNSA-N 0.000 claims description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims description 2
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims description 2
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims description 2
- 235000013336 milk Nutrition 0.000 claims description 2
- 239000008267 milk Substances 0.000 claims description 2
- 210000004080 milk Anatomy 0.000 claims description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 2
- 229940090181 propyl acetate Drugs 0.000 claims description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 239000002884 skin cream Substances 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 6
- 239000000654 additive Substances 0.000 description 5
- 238000009736 wetting Methods 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 4
- 238000005187 foaming Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- NZJXADCEESMBPW-UHFFFAOYSA-N 1-methylsulfinyldecane Chemical compound CCCCCCCCCCS(C)=O NZJXADCEESMBPW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 230000008719 thickening Effects 0.000 description 3
- CJPDBKNETSCHCH-UHFFFAOYSA-N 1-methylsulfinyldodecane Chemical compound CCCCCCCCCCCCS(C)=O CJPDBKNETSCHCH-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- XHKPPUVICXLDRJ-UHFFFAOYSA-N Thiodiglycol sulphoxide Natural products OCCS(=O)CCO XHKPPUVICXLDRJ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 1
- KELGBPHGJYCRSO-UHFFFAOYSA-N 1-ethylsulfinyldodecane Chemical compound CCCCCCCCCCCCS(=O)CC KELGBPHGJYCRSO-UHFFFAOYSA-N 0.000 description 1
- WCYBVMILLYKJMT-UHFFFAOYSA-N 1-propylsulfinyldodecane Chemical compound CCCCCCCCCCCCS(=O)CCC WCYBVMILLYKJMT-UHFFFAOYSA-N 0.000 description 1
- MFWFLYVQFMEYJO-UHFFFAOYSA-N 2-dodecylsulfinylethanol Chemical compound CCCCCCCCCCCCS(=O)CCO MFWFLYVQFMEYJO-UHFFFAOYSA-N 0.000 description 1
- 241000270725 Caiman Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000008271 cosmetic emulsion Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- SMVRDGHCVNAOIN-UHFFFAOYSA-L disodium;1-dodecoxydodecane;sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O.CCCCCCCCCCCCOCCCCCCCCCCCC SMVRDGHCVNAOIN-UHFFFAOYSA-L 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical class CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005430 electron energy loss spectroscopy Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- LSPBOUZMSSAOCP-UHFFFAOYSA-N methylsulfanylmethane;methylsulfinylmethane Chemical compound CSC.CS(C)=O LSPBOUZMSSAOCP-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- DWTTZBARDOXEAM-UHFFFAOYSA-N zearalenone Chemical compound O=C1OC(C)CCCC(O)CCCCCC2=CC(O)=CC(O)=C21 DWTTZBARDOXEAM-UHFFFAOYSA-N 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/46—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings substituted on the ring sulfur atom
- C07D333/48—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings substituted on the ring sulfur atom by oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing or bathing preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B45/00—Formation or introduction of functional groups containing sulfur
- C07B45/04—Formation or introduction of functional groups containing sulfur of sulfonyl or sulfinyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Dermatology (AREA)
- Detergent Compositions (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7337867A FR2249077B1 (enrdf_load_stackoverflow) | 1973-10-24 | 1973-10-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2450634A1 true DE2450634A1 (de) | 1975-04-30 |
Family
ID=9126844
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742450634 Pending DE2450634A1 (de) | 1973-10-24 | 1974-10-24 | Verfahren zur herstellung von organischen sulfoxiden |
Country Status (11)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3008859A1 (de) * | 1980-03-07 | 1981-09-24 | Mitsui Toatsu Chemicals, Inc., Tokyo | Verfahren zur herstellung von 2,2'-bisphenolsulfoxiden |
| EP0091052A3 (en) * | 1982-04-06 | 1985-04-10 | Nihon Tokushu Noyaku Seizo K.K. | Industrial process for the oxidation of thioethers and thiol-carboxylic-acid derivatives |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU86229A1 (fr) * | 1985-12-27 | 1987-07-24 | Oreal | Compositions cosmetiques pour le traitement de la peau et des cheveux gras,a base de di(beta-hydroxyethyl)sulfoxyde,et leur application |
-
1973
- 1973-10-24 FR FR7337867A patent/FR2249077B1/fr not_active Expired
-
1974
- 1974-10-22 CH CH1408774A patent/CH590831A5/xx not_active IP Right Cessation
- 1974-10-23 IT IT2870474A patent/IT1025131B/it active
- 1974-10-23 GB GB4586374A patent/GB1488818A/en not_active Expired
- 1974-10-24 DE DE19742450634 patent/DE2450634A1/de active Pending
- 1974-10-24 CA CA212,178A patent/CA1047505A/fr not_active Expired
- 1974-10-24 JP JP12297974A patent/JPS5088027A/ja active Pending
- 1974-10-24 NL NL7413925A patent/NL7413925A/xx not_active Application Discontinuation
- 1974-10-24 BE BE1006247A patent/BE821409A/xx unknown
- 1974-10-24 ES ES431319A patent/ES431319A1/es not_active Expired
- 1974-10-25 LU LU71176A patent/LU71176A1/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3008859A1 (de) * | 1980-03-07 | 1981-09-24 | Mitsui Toatsu Chemicals, Inc., Tokyo | Verfahren zur herstellung von 2,2'-bisphenolsulfoxiden |
| EP0091052A3 (en) * | 1982-04-06 | 1985-04-10 | Nihon Tokushu Noyaku Seizo K.K. | Industrial process for the oxidation of thioethers and thiol-carboxylic-acid derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| CA1047505A (fr) | 1979-01-30 |
| NL7413925A (nl) | 1975-04-28 |
| LU71176A1 (enrdf_load_stackoverflow) | 1975-06-24 |
| GB1488818A (en) | 1977-10-12 |
| FR2249077B1 (enrdf_load_stackoverflow) | 1979-06-29 |
| IT1025131B (it) | 1978-08-10 |
| JPS5088027A (enrdf_load_stackoverflow) | 1975-07-15 |
| BE821409A (enrdf_load_stackoverflow) | 1975-04-24 |
| FR2249077A1 (enrdf_load_stackoverflow) | 1975-05-23 |
| ES431319A1 (es) | 1977-10-01 |
| CH590831A5 (enrdf_load_stackoverflow) | 1977-08-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |