GB917921A - Improvements in or relating to a process for the manufacture of mercaptans - Google Patents
Improvements in or relating to a process for the manufacture of mercaptansInfo
- Publication number
- GB917921A GB917921A GB1760758A GB1760758A GB917921A GB 917921 A GB917921 A GB 917921A GB 1760758 A GB1760758 A GB 1760758A GB 1760758 A GB1760758 A GB 1760758A GB 917921 A GB917921 A GB 917921A
- Authority
- GB
- United Kingdom
- Prior art keywords
- mercaptan
- lauryl
- alcohol
- acid
- effected
- 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
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 4
- 238000006317 isomerization reaction Methods 0.000 abstract 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 abstract 2
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 abstract 2
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000011574 phosphorus Substances 0.000 abstract 2
- 229910052698 phosphorus Inorganic materials 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- GAYUSSOCODCSNF-UHFFFAOYSA-N 1-(dodecyldisulfanyl)dodecane Chemical compound CCCCCCCCCCCCSSCCCCCCCCCCCC GAYUSSOCODCSNF-UHFFFAOYSA-N 0.000 abstract 1
- UPYPTOCXMIWHSG-UHFFFAOYSA-N 1-dodecylsulfanyldodecane Chemical compound CCCCCCCCCCCCSCCCCCCCCCCCC UPYPTOCXMIWHSG-UHFFFAOYSA-N 0.000 abstract 1
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 abstract 1
- LSESCEUNBVHCTC-UHFFFAOYSA-N 6-methylheptane-1-thiol Chemical compound CC(C)CCCCCS LSESCEUNBVHCTC-UHFFFAOYSA-N 0.000 abstract 1
- -1 Alkyl mercaptans Chemical class 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 239000002518 antifoaming agent Substances 0.000 abstract 1
- 229960000541 cetyl alcohol Drugs 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- ORTRWBYBJVGVQC-UHFFFAOYSA-N hexadecane-1-thiol Chemical compound CCCCCCCCCCCCCCCCS ORTRWBYBJVGVQC-UHFFFAOYSA-N 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 150000007529 inorganic bases Chemical class 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 229910017053 inorganic salt Inorganic materials 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 239000002798 polar solvent Substances 0.000 abstract 1
- 150000003138 primary alcohols Chemical class 0.000 abstract 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/17—Esters of thiophosphoric acids with hydroxyalkyl compounds without further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Alkyl mercaptans are prepared by heating an inorganic salt of a dialkyl dithiophosphoric acid containing two alkyl-oxygen-phosphorus linkages to effect an isomerisation to produce a salt of a dialkyldithiophosphoric acid containing two alkyl-sulphur-phosphorus linkages, which is thereafter hydrolysed to liberate a free mercaptan. The dialkyldithiophosphoric acid salts used as starting materials are prepared by reacting an alkanol with P2S5, the alcohol preferably being a primary alcohol, and then reacting the resulting dialkyl dithiophosphoric acid with an alkali metal, alkaline earth metal or inorganic base, desirably using sodium sulphide in the presence of an antifoaming agent. The isomerisation is suitably effected in an inert organic polar solvent, e.g. a phenol. The hydrolysis may be effected by heating with aqueous mineral acid. Examples describe the conversion of (1) lauryl alcohol to lauryl mercaptan and a mixture of lauryl thioether and dilauryl disulphide, which mixture is reduced with zinc and acid to yield more lauryl mercaptan; (7) butanol to butyl mercaptan; (8) isooctanol to isooctyl mercaptan and (9) cetyl alcohol to cetyl mercaptan, the isomerisations being effected at temperatures ranging from 138 DEG to 220 DEG C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1760758A GB917921A (en) | 1958-06-02 | 1958-06-02 | Improvements in or relating to a process for the manufacture of mercaptans |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1760758A GB917921A (en) | 1958-06-02 | 1958-06-02 | Improvements in or relating to a process for the manufacture of mercaptans |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB917921A true GB917921A (en) | 1963-02-13 |
Family
ID=10098107
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1760758A Expired GB917921A (en) | 1958-06-02 | 1958-06-02 | Improvements in or relating to a process for the manufacture of mercaptans |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB917921A (en) |
-
1958
- 1958-06-02 GB GB1760758A patent/GB917921A/en not_active Expired
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