GB953834A - Production of alkylmercaptophenols - Google Patents
Production of alkylmercaptophenolsInfo
- Publication number
- GB953834A GB953834A GB103163A GB103163A GB953834A GB 953834 A GB953834 A GB 953834A GB 103163 A GB103163 A GB 103163A GB 103163 A GB103163 A GB 103163A GB 953834 A GB953834 A GB 953834A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenol
- iso
- treated
- disulphides
- catalyst
- 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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 4
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 abstract 4
- 239000003054 catalyst Substances 0.000 abstract 3
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 abstract 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 abstract 2
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 abstract 2
- 150000002989 phenols Chemical class 0.000 abstract 2
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 abstract 2
- SOOARYARZPXNAL-UHFFFAOYSA-N 2-(Methylthio)phenol Chemical compound CSC1=CC=CC=C1O SOOARYARZPXNAL-UHFFFAOYSA-N 0.000 abstract 1
- 229940061334 2-phenylphenol Drugs 0.000 abstract 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 abstract 1
- YYOQJBLGFMMRLJ-UHFFFAOYSA-N 3,5-di(propan-2-yl)phenol Chemical compound CC(C)C1=CC(O)=CC(C(C)C)=C1 YYOQJBLGFMMRLJ-UHFFFAOYSA-N 0.000 abstract 1
- HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- RECUKUPTGUEGMW-UHFFFAOYSA-N carvacrol Chemical compound CC(C)C1=CC=C(C)C(O)=C1 RECUKUPTGUEGMW-UHFFFAOYSA-N 0.000 abstract 1
- HHTWOMMSBMNRKP-UHFFFAOYSA-N carvacrol Natural products CC(=C)C1=CC=C(C)C(O)=C1 HHTWOMMSBMNRKP-UHFFFAOYSA-N 0.000 abstract 1
- AVIJCTKPQJGONY-UHFFFAOYSA-N chloro-(chloromethyldisulfanyl)methane Chemical class ClCSSCCl AVIJCTKPQJGONY-UHFFFAOYSA-N 0.000 abstract 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 229960001867 guaiacol Drugs 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 235000010292 orthophenyl phenol Nutrition 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- OLBCVFGFOZPWHH-UHFFFAOYSA-N propofol Chemical compound CC(C)C1=CC=CC(C(C)C)=C1O OLBCVFGFOZPWHH-UHFFFAOYSA-N 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
4-Alkylmercaptophenols are prepared by reacting phenol, or a substituted phenol having a free 4-position, with a dialkyl disulphide in the presence of a phosphoric acid catalyst. Specified phenols which may be treated are phenol, m-cresol, 3-ethyl-and-3-isopropyl-phenol, 2-tertbutylphenol, 3-methyl-6-isopropylphenol, 3, 5-diisopropylphenol, 2, 6-diisopropylphenol, 2-methyl-5-isopropylphenol, 3, 5-dimethylphenol, 2-phenylphenol, 3-chlorophenol and 2-methoxyphenol. Specified dialkyl disulphides are dimethyl, diethyl, di-n-and di-iso-propyl, di-n-and di-iso-butyl di-n-and di-iso-amyl and di (chloromethyl) disulphides. The catalyst may be ortho-, meta-, pyro- or poly-phosphoric acid. The reaction may be effected under reflux, and the catalyst may be separated from the product and re-used. The alkylmercaptans obtained as by-products may be used as such or oxidized to the corresponding disulphides. Examples are given in which phenol and m-cresol are treated with dimethyl disulphide, minor proportions of 2-methylmercaptophenol being also obtained when phenol is treated.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16966562A | 1962-01-29 | 1962-01-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB953834A true GB953834A (en) | 1964-04-02 |
Family
ID=22616648
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB103163A Expired GB953834A (en) | 1962-01-29 | 1963-01-09 | Production of alkylmercaptophenols |
Country Status (2)
| Country | Link |
|---|---|
| CH (1) | CH442348A (en) |
| GB (1) | GB953834A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1984004092A1 (en) * | 1983-04-12 | 1984-10-25 | Ethyl Corp | (hydrocarbylthio)phenols and their preparation |
| USRE31771E (en) * | 1980-07-28 | 1984-12-18 | Ethyl Corporation | Process for the preparation of ortho-(hydrocarbylthio)-phenols |
| US4533753A (en) * | 1982-09-30 | 1985-08-06 | Ethyl Corporation | (Hydrocarbylthio)phenols and their preparation |
-
1963
- 1963-01-07 CH CH11063A patent/CH442348A/en unknown
- 1963-01-09 GB GB103163A patent/GB953834A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE31771E (en) * | 1980-07-28 | 1984-12-18 | Ethyl Corporation | Process for the preparation of ortho-(hydrocarbylthio)-phenols |
| US4533753A (en) * | 1982-09-30 | 1985-08-06 | Ethyl Corporation | (Hydrocarbylthio)phenols and their preparation |
| WO1984004092A1 (en) * | 1983-04-12 | 1984-10-25 | Ethyl Corp | (hydrocarbylthio)phenols and their preparation |
| US4602113A (en) * | 1983-04-12 | 1986-07-22 | Ethyl Corporation | (Hydrocarbylthio) phenols and their preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| CH442348A (en) | 1967-08-31 |
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