US4868336A
Expired / Lapsed
US
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Manufacture of disulfides
Assignee: Phillips Petroleum Co
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Filing: 1987-11-20
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Granted: 1989-09-19
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Expires: 2007-11-20
Abstract
Abstract A method for preparing disulfides comprising combining at least one mercaptan of the general formula R-SH wherein R is selected from the group consisting of an alkyl, aryl, aralkyl, cycloalkyl, arylcycloalkyl radical, and mixtures thereof; at least one oxidizing agent; at least one aqueous base; at least one oxygen containing water miscible organic compound; and at least one divalent transition metal carboxylic acid salt and/or divalent transition metal sulfate salt.
Inventors
- 👤 Stewart H. Presnall
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 12:45
CPC Classifications
C; C07; C07C; C07C319/00; C07C319/22; C07C319/24
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
149 words
A process for producing a disulfide product comprising combining the following reactants: (a) at least one compound of the formula R-SH containing from about 8 to about 18 carbon atoms wherein R is selected from the group consisting of alkyl, aryl, aralkyl, alkaryl, cycloalkyl, arylcycloalkyl radicals, and mixtures thereof; (b) at least one oxidizing agent in a quantity sufficient to maintain an appropriate reaction temperature and to maintain an appropriate oxidation rate; (c) at least one aqueous metal hydroxide base sufficient to give a pH of about 8 to about 14; (d) at least one normally liquid oxygen containing, water miscible organic compound selected from the group consisting of polyhydric alcohols, and mono- and dialkyl-ethers of alkylene glycols; and (e) at least one compound selected from the group consisting of divalent transition metal carboxylic acid salts, divalent transition metal carboxylic acid derivative salts, and divalent transition metal sulfate salts.
Claim 2
Dependent Claim
149 words
A process for producing a disulfide product comprising combining the following reactants: (a) at least one compound of the formula R-SH containing from about 8 to about 18 carbon atoms wherein R is selected from the group consisting of alkyl, aryl, aralkyl, alkaryl, cycloalkyl, arylcycloalkyl radicals, and mixtures thereof; (b) at least one oxidizing agent in a quantity sufficient to maintain an appropriate reaction temperature and to maintain an appropriate oxidation rate; (c) at least one aqueous metal hydroxide base sufficient to give a pH of about 8 to about 14; (d) at least one normally liquid oxygen containing, water miscible organic compound selected from the group consisting of polyhydric alcohols, and mono- and dialkyl-ethers of alkylene glycols; and (e) at least one compound selected from the group consisting of divalent transition metal carboxylic acid salts, divalent transition metal carboxylic acid derivative salts, and divalent transition metal sulfate salts.
Claim 3
Dependent Claim
20 words
A process according to claim 1 wherein said reactants are combined in a vessel substantially simultaneously and allowed to react.
Claim 4
Dependent Claim
12 words
A process according to claim 1 wherein said R-SH compound is dodecylmercaptan.
Claim 5
Dependent Claim
20 words
A process according to claim 1 wherein said R-SH compound contains about 10 to about 16 carbon atoms per molecule.
Claim 6
Dependent Claim
42 words
A process according to claim 1 wherein said R-SH compound is initially present in a reactor vessel in a concentration in the range of about 50 to about 99 weight percent, based on the contents of all reactants in the reaction vessel.
Claim 7
Dependent Claim
33 words
A process according to claim 1 wherein said oxidizing agent is selected from the group consisting of air, oxygen, a synthetic mixture of oxygen and an inert gas, hydrogen peroxide, and mixtures thereof.
Claim 8
Dependent Claim
35 words
A process according to claim 1 wherein said oxidizing agent is a gas and is added to a reactor vessel at a rate less than or equal to about 50 standard cubic feet per minute
Claim 9
Dependent Claim
20 words
A process according to claim 1 wherein said base of said aqueous metal hydroxide base is an alkali metal hydroxide.
Claim 10
Dependent Claim
29 words
A process according to claim 8 wherein said alkali metal hydroxide is selected from the group consisting of lithium hydroxide, sodium hydroxide, rubidium hydroxide, cesium hydroxide, and mixtures thereof.
Claim 11
Dependent Claim
39 words
A process according to claim 1 wherein said base of said aqueous metal hydroxide base is selected from the group consisting of magnesium hydroxide, calcium hydroxide, barium hydroxide, lithium hydroxide, sodium hydroxide, rubidium hydroxide, cesium hydroxide, and mixtures thereof.
Claim 12
Dependent Claim
43 words
A process according to claim 1 wherein said base of said aqueous metal hydroxide base is initially present in a reactor vessel in a mole ratio of said R-SH compound to said aqueous base in the range of about 40:1 to about 4:1.
Claim 13
Dependent Claim
26 words
A process according to claim 1 wherein said transition metal is selected from the group consisting of copper, iron, cobalt, zinc, silver, chromium, and mixtures thereof.
Claim 14
Dependent Claim
30 words
A process according to claim 1 wherein said divalent metal is initially present in a reactor vessel in a concentration in the range of about 50 to about 1,000 mg/L.
Claim 15
Dependent Claim
21 words
A process according to claim 1 wherein said temperature during said reacting step is maintained less than or about 55° C.
Claim 16
Dependent Claim
19 words
A process according to claim 1 wherein said pressure during said reacting step is maintained at about atmospheric pressure.
Claim 17
Dependent Claim
15 words
A process according to claim 1 further comprising a step of recovering said disulfide product.
Claim 18
Dependent Claim
32 words
A process of producing di-tert-dodecyl disulfide comprising combining the following reactants: (a) tert-dodecylthiol; (b) air; (c) sodium hydroxide dissolved in water; (d) 2-(2-methoxyethoxy)ethanol; and (e) copper sulfate at ambient temperature and pressure.
Claim 19
Dependent Claim
32 words
A process of producing di-tert-dodecyl disulfide comprising combining the following reactants: (a) tert-dodecylthiol; (b) air; (c) sodium hydroxide dissolved in water; (d) 2-(2-methoxyethoxy)ethanol; and (e) copper sulfate at ambient temperature and pressure.
Claim 20
Dependent Claim
15 words
A process according to claim 17 further comprising a step of purifying said disulfide product.
Claim 21
Dependent Claim
16 words
A process according to claim 18 wherein said disulfide product is purified with an acidic solution.
Claim 22
Dependent Claim
17 words
A process according to claim 19 wherein said acidic solution is an aqueous solution of hydrochloric acid.
Claim 23
Dependent Claim
23 words
A process according to claim 20 wherein said aqueous solution of hydrochloric acid is about 3 volume percent of concentrated acid in water.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1992-09-18 | 1993-03-20 | 1993-09-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-09-18 | 1997-03-20 | 1997-09-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-09-18 | 2001-03-20 | 2001-09-19 | $7700.00 | Window Closed / Lapsed |