US5464931A
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Oxidation of dimercaptans to organic disulfide polymers
Assignee: Phillips Petroleum Co
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Filing: 1994-08-15
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Granted: 1995-11-07
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Expires: 2014-08-15
Abstract
Abstract A process for preparing an organic disulfide polymer such as polyethylene disulfide which is used in batteries comprises contacting a dimercaptan such as 1,2-ethanedithiol with elemental sulfur using a mixture of a basic compound such as NaOH and an ethoxylated alcohol such as Union Carbide's TERGITOL® 15-S-7 as catalyst wherein the dimercaptan is present in excess amount to effect the preparation of the disulfide polymer.
Inventors
- 👤 James E. Shaw
- 👤 William E. Sattich
- 👤 Howard F. Efner
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 23:19
CPC Classifications
C; C07; C07C; C07C319/00; C07C319/22; C07C319/24; C08; C08G; C08G75/00; C08G75/14; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/582
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
44 words
A process for producing an organic disulfide polymer comprising contacting a dithiol with elemental sulfur in the presence of a catalyst wherein said catalyst comprises a base and an alkoxylated compound selected from the group consisting of alkoxylated alcohol, alkoxylated mercaptan, and combinations thereof.
Claim 2
Dependent Claim
44 words
A process for producing an organic disulfide polymer comprising contacting a dithiol with elemental sulfur in the presence of a catalyst wherein said catalyst comprises a base and an alkoxylated compound selected from the group consisting of alkoxylated alcohol, alkoxylated mercaptan, and combinations thereof.
Claim 3
Dependent Claim
47 words
A process according to claim 1 wherein said organic disulfide polymer has a formula of HS--R 4 --S--S) q R 4 SH wherein R 4 is a hydrocarbyl radical having 1 to about 20 carbon atoms and q is a number of about 1 to about 1,000.
Claim 4
Dependent Claim
30 words
A process according to claim 2 wherein R 4 is a hydrocarbyl radical having 2 to 15 carbon atoms and q is a number of about 5 to about 500.
Claim 5
Dependent Claim
28 words
A process according to claim 1 wherein said organic disulfide polymer is polyethylene disulfide having the formula of ##STR3## wherein q is a number from 10 to 200.
Claim 6
Dependent Claim
34 words
A process according to claim 1 wherein said dithiol is selected from the group consisting of 1,2-ethanedithiol, 1,2-propanedithiol, 1,3-propanedithiol, 1,10-decanedithiol, dipentene dimercaptan, ethylcyclohexyl dimercaptan, 1,4-benzenedithiol, 1,2-benzenedithiol, 1,3-benzenedithiol, and combinations of two or more thereof.
Claim 7
Dependent Claim
11 words
A process according to claim 1 wherein said dithiol is 1,2-ethanedithiol.
Claim 8
Dependent Claim
65 words
A process according to claim 1 wherein said base is selected from the group consisting of tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetramethylammonium bisulfide, tetraethylammonium bisulfide, lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, magnesium hydroxide, sodium bicarbonate, sodium carbonate, sodium oxide, magnesium oxide, calcium oxide, calcium carbonate, potassium carbonate, sodium phenoxide, sodium bisulfide, sodium sulfide, barium phenoxide, calcium phenoxide, RONa, RSNa, and mixtures thereof.
Claim 9
Dependent Claim
12 words
A process according to claim 1 wherein said base is sodium hydroxide.
Claim 10
Dependent Claim
84 words
A process according to claim 1 wherein said alkoxylated alcohol has a general formula of R 1 O[CH 2 CH(R 2 )O] n H wherein R 1 is a hydrocarbyl radical selected from the group consisting of alkyl radical, alkylaryl radical, aryl radical, cycloalkyl radical and alkenyl radical; R 2 is selected from the group consisting of hydrogen, C 1 -C 16 alkyl radical, C 2 -C 16 alkenyl radical, and combinations thereof; and n is a number of from 1 to about 20.
Claim 11
Dependent Claim
51 words
A process according to claim 1 wherein said alkoxylated alcohol is an ethoxylated alcohol having the formula of R 1 O(CH 2 CH 2 O) 7 H, wherein R 1 is a secondary alkyl radical having 11 to 15 carbon atoms and 7 is an average number of ethylene oxide units.
Claim 12
Dependent Claim
84 words
A process according to claim 1 wherein said alkoxylated mercaptan has a general formula of R 1 S[CH 2 CH(R 2 )O] n H wherein R 1 is a hydrocarbyl radical selected from the group consisting of alkyl radical, alkenyl radical, alkylaryl radical, aryl radical and cycloalkyl radical; R 2 is selected from the group consisting of hydrogen, C 1 -C 6 alkyl radical, C 2 -C 16 alkenyl radical, and combinations thereof; and n is an integer of from 1 to about 20.
Claim 13
Dependent Claim
47 words
A process according to claim 1 wherein said alkoxylated mercaptan is an ethoxylated mercaptan surfactant having the formula of R 1 S(CH 2 CH 2 O) 7 H, wherein R 1 is mainly a tertiary dodecyl radical and 7 is an average number of ethylene oxide units.
Claim 14
Dependent Claim
54 words
A process according to claim 1 wherein said catalyst is prepared by heating sodium hydroxide and an ethoxylated alcohol having the formula of R 1 O(CH 2 CH 2 O) 7 H wherein R 1 is a secondary alkyl radical having 11-15 carbon atoms and 7 is an average number of ethylene oxide units.
Claim 15
Dependent Claim
18 words
A process according to claim 1 wherein said process is carried out in the presence of a solvent.
Claim 16
Dependent Claim
23 words
A process according to claim 14 wherein said solvent is selected from the group consisting of water, alcohols, hydrocarbons, ethers, and mixtures thereof.
Claim 17
Dependent Claim
11 words
A process according to claim 14 wherein said solvent is methanol.
Claim 18
Dependent Claim
25 words
A process according to claim 1 wherein said dithiol is present in excess amount (about 2 moles of said dithiol per mole of elemental sulfur).
Claim 19
Dependent Claim
21 words
A process according to claim 15 wherein unreacted excess dithiol is separated from said organic disulfide polymer for reuse as reactant.
Claim 20
Dependent Claim
25 words
A process according to claim 14 wherein said dithiol is present in excess amount (about 2 moles of said dithiol per mole of elemental sulfur).
Claim 21
Dependent Claim
24 words
A process according to claim 19 further comprising separating a mixture of said solvent, said catalyst, and unreacted dithiol from said organic disulfide polymer.
Claim 22
Dependent Claim
17 words
A process according to claim 20 wherein said mixture is recycled to produce said organic disulfide polymer.
Claim 23
Dependent Claim
92 words
A process for producing polyethylene disulfide comprising contacting 1,2-ethanedithiol with elemental sulfur in the presence of a catalyst at a temperature in the range of from 50° C. to 150° C. for 1 minute to 5 hours to form a product mixture; wherein said catalyst is prepared by heating sodium hydroxide and an ethoxylated alcohol having the formula of R 1 O(CH 2 CH 2 O) 7 H wherein R 1 is a secondary alkyl radical having 11 to 15 carbon atoms and 7 is an average number of ethylene oxide units.
Claim 24
Dependent Claim
92 words
A process for producing polyethylene disulfide comprising contacting 1,2-ethanedithiol with elemental sulfur in the presence of a catalyst at a temperature in the range of from 50° C. to 150° C. for 1 minute to 5 hours to form a product mixture; wherein said catalyst is prepared by heating sodium hydroxide and an ethoxylated alcohol having the formula of R 1 O(CH 2 CH 2 O) 7 H wherein R 1 is a secondary alkyl radical having 11 to 15 carbon atoms and 7 is an average number of ethylene oxide units.
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