US4082790A
Expired / Lapsed
US
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Method of preparing mercaptans
Assignee: Dow Silicones Corp
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Filing: 1975-03-10
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Granted: 1978-04-04
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Expires: 1995-03-10
Abstract
Abstract Mercaptans are prepared by reacting an organic chloride or bromide with a mixture of H 2 S and ammonia or an amine at a temperature of 0° to 175° C. under autogenous pressure. The reaction can be carried out in the presence of a polar solvent. For example, 3-chloropropyltrimethoxysilane is mixed with H 2 S and ammonia in methanol and heated in a closed container at 100° C. for 18 hours.
Inventors
- 👤 John L. Speier
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 17:54
CPC Classifications
C; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C07F7/1804; C07F7/1872; C07F7/1892; C07C; C07C319/00; C07C319/02; C07C319/14
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
263 words
A method of producing mercaptans which comprises reacting (A) a halide of the formula RX a with a mixture of (B) ammonia or a hydrocarbyl amine containing one N atom, no more than 6 carbon atoms and being free of aliphatic unsaturation and having a K a of less than 1 × 10 -9 in aqueous solution, and H 2 S, in the mole ratio of at least one mole of H 2 S and one mole of (B) per mole of halogen in (A), at a temperature of from 0° to 175° C. under autogenous pressure whereby a compound of the formula R(sh) a is formed, in which process R is selected from the group consisting of aliphatic, cycloaliphatic or aralkyl hydrocarbon radicals free of aliphatic unsaturation, such hydrocarbon radicals substituted with alkoxy, keto, carboxy, hydroxyl, --COOR 3 or --OOCR 3 radicals in which R 3 is a monovalent hydrocarbon radical free of aliphatic unsaturation, and silylated hydrocarbon radicals of the formula (R"O) y R''' 3-y SiR 4 -- or (O 3-d/2 )R''' d SiR 4 -- in which R" is an alkyl or an alkoxyalkyl radical of 1 to 6 carbon atoms, R''' is a monovalent hydrocarbon radical free of aliphatic unsaturation, a haloaryl radical or R f CH 2 CH 2 -- in which R f is a perfluoroalkyl radical, R 4 is a divalent, trivalent or tetravalent, aliphatic, cycloaliphatic or aralkyl hydrocarbon radical free of aliphatic unsaturation, y is 1 to 3 and d is 0 to 2, X is bromine or chlorine, and a is 1 to 3.
Claim 2
Independent Claim
263 words
A method of producing mercaptans which comprises reacting (A) a halide of the formula RX a with a mixture of (B) ammonia or a hydrocarbyl amine containing one N atom, no more than 6 carbon atoms and being free of aliphatic unsaturation and having a K a of less than 1 × 10 -9 in aqueous solution, and H 2 S, in the mole ratio of at least one mole of H 2 S and one mole of (B) per mole of halogen in (A), at a temperature of from 0° to 175° C. under autogenous pressure whereby a compound of the formula R(sh) a is formed, in which process R is selected from the group consisting of aliphatic, cycloaliphatic or aralkyl hydrocarbon radicals free of aliphatic unsaturation, such hydrocarbon radicals substituted with alkoxy, keto, carboxy, hydroxyl, --COOR 3 or --OOCR 3 radicals in which R 3 is a monovalent hydrocarbon radical free of aliphatic unsaturation, and silylated hydrocarbon radicals of the formula (R"O) y R''' 3-y SiR 4 -- or (O 3-d/2 )R''' d SiR 4 -- in which R" is an alkyl or an alkoxyalkyl radical of 1 to 6 carbon atoms, R''' is a monovalent hydrocarbon radical free of aliphatic unsaturation, a haloaryl radical or R f CH 2 CH 2 -- in which R f is a perfluoroalkyl radical, R 4 is a divalent, trivalent or tetravalent, aliphatic, cycloaliphatic or aralkyl hydrocarbon radical free of aliphatic unsaturation, y is 1 to 3 and d is 0 to 2, X is bromine or chlorine, and a is 1 to 3.
Claim 3
Dependent Claim
14 words
The process of claim 1 which is carried out in a non-acidic, polar solvent.
Claim 4
Dependent Claim
10 words
The process of claim 1 in which (B) is ammonia.
Claim 5
Dependent Claim
28 words
The process of claim 1 in which (A) is (R"O) y R''' 3--y SiR 4 -- or (O 3-d/2 )R" d SiR 4 -- and (B) is ammonia.
Claim 6
Dependent Claim
32 words
The process of claim 1 in which (A) is (CH 3 O) n (CH 3 ) 3-n Si(CH 2 ) 3 Cl where n is 1 to 3 and (B) is ammonia.
Claim 7
Dependent Claim
38 words
The process of claim 2 in which (A) is (CH 3 O) n (CH 3 ) 3-n Si(CH 2 ) 3 Cl in which n is 1 to 3, (B) is ammonia and the polar solvent is methanol.
Claim 8
Dependent Claim
10 words
The process of claim 6 in which n is 3.
Claim 9
Dependent Claim
12 words
The process of claim 2 in which the polar solvent is methanol.
Claim 10
Dependent Claim
28 words
The process of claim 1 in which (A) is a siloxane which also contains units of the formula R''' z SiO.sub.(4-z/2) in which z is 0 to 3.
Claim 11
Dependent Claim
10 words
The process of claim 9 in which (B) is ammonia.
References Cited (Backward Citations)
US3590065A
Cited
US3856842A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-04-03 | 1981-10-03 | 1982-04-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-04-03 | 1985-10-03 | 1986-04-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-04-03 | 1989-10-03 | 1990-04-04 | $7700.00 | Window Closed / Lapsed |