US4014891A
Expired / Lapsed
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Process for making aryl chloromethyl sulfides
Assignee: Dow Chemical Co
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Filing: 1975-01-17
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Granted: 1977-03-29
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Expires: 1995-01-17
Abstract
Abstract The title compounds are prepared in excellent yields by reacting an alkali aromatic mercaptide with bromochloromethane in the presence of a quaternary ammonium salt having ten or more carbon atoms. Normally the chlorobromomethane is used in excess as the liquid reaction medium. Reaction temperatures are normally selected in the range of from about 20° to about 65° C.
Inventors
- 👤 Christian T. Goralski
- 👤 George A. Burk
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 19:53
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/62; C07D213/70; C07C; C07C319/00; C07C319/14; C07D215/00; C07D215/02; C07D215/16; C07D215/36; C07D233/00; C07D233/04; C07D233/28; C07D233/30; C07D233/42; C07D263/00; C07D263/52; C07D263/54; C07D263/58; C07D275/00; C07D275/02; C07D275/03; C07D277/00; C07D277/60; C07D277/62; C07D277/68; C07D277/70; C07D277/74; C07D285/00; C07D285/01; C07D285/02; C07D285/04; C07D285/12; C07D285/125
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
62 words
A process for preparing an aryl chloromethyl sulfide comprising reacting by contacting in liquid phase (a) an alkali metal aryl mercaptide with (b) bromochloromethane in the presence of (c) a small but sufficient amount of a quaternary ammonium salt to catalyze the reaction between (a) and (b); said quaternary ammonium salt having an aggregate carbon content of at least 10 carbon atoms.
Claim 2
Dependent Claim
62 words
A process for preparing an aryl chloromethyl sulfide comprising reacting by contacting in liquid phase (a) an alkali metal aryl mercaptide with (b) bromochloromethane in the presence of (c) a small but sufficient amount of a quaternary ammonium salt to catalyze the reaction between (a) and (b); said quaternary ammonium salt having an aggregate carbon content of at least 10 carbon atoms.
Claim 3
Dependent Claim
27 words
The process defined by claim 1 wherein (c) is a quaternary ammonium salt having an aggregate carbon content of from about 12 to about 31 carbon atoms.
Claim 4
Dependent Claim
19 words
The process defined by claim 2 wherein (c) is a benzyltrimethyl-, a benzyltriethyl-, a tetra-n-butyl- or a tri-n-butylmethylammonium salt.
Claim 5
Dependent Claim
22 words
The process defined by claim 1 wherein (a) is formed in situ by reacting an aromatic mercaptan with an alkali metal hydroxide.
Claim 6
Dependent Claim
16 words
The process defined by claim 4 wherein said alkali metal hydroxide is sodium or potassium hydroxide.
Claim 7
Dependent Claim
13 words
The process defined by claim 5 wherein the reaction medium is liquid bromochloromethane.
Claim 8
Dependent Claim
19 words
The process defined by claim 6 wherein (c) is a benzyltrimethyl-, a benzyltriethyl-, a tetra-n-butyl- or a tri-n-butylmethylammonium salt.
Claim 9
Dependent Claim
26 words
The process defined by claim 1 wherein (a) is a sodium or potassium salt of a benzenethiol bearing fluorine, chlorine, or bromine on the aromatic ring.
Claim 10
Dependent Claim
16 words
The process defined by claim 1 wherein (a) is a sodium or potassium salt of 2,5-dimercapto-1,3,4-thiadiazole.
Claim 11
Dependent Claim
16 words
The process defined by claim 1 wherein (a) is a sodium or potassium salt of 4-cyano-3,5-dimercaptoisothiazole.
Claim 12
Dependent Claim
30 words
The process defined by claim 7 wherein (a) is a sodium or potassium salt of a tri- or tetrahalobenzenethiol, with the provision that said halo-substituents are fluorine, chlorine, or bromine.
Claim 13
Dependent Claim
22 words
The process defined by claim 7 wherein said aromatic mercaptan is a benzenethiol bearing fluorine, chlorine or bromine on the aromatic ring.
Claim 14
Dependent Claim
12 words
The process defined by claim 7 wherein said aromatic mercaptan is 2,5-dimercapto-1,3,4-thiadiazole.
Claim 15
Dependent Claim
12 words
The process defined by claim 7 wherein said aromatic mercaptan is 4-cyano-3,5-dimercaptoisothiazole.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-03-28 | 1980-09-27 | 1981-03-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-03-28 | 1984-09-27 | 1985-03-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-03-28 | 1988-09-27 | 1989-03-29 | $7700.00 | Window Closed / Lapsed |