GB1278188A - Process for the preparation of dialkyl sulphides - Google Patents
Process for the preparation of dialkyl sulphidesInfo
- Publication number
- GB1278188A GB1278188A GB61039/70A GB6103970A GB1278188A GB 1278188 A GB1278188 A GB 1278188A GB 61039/70 A GB61039/70 A GB 61039/70A GB 6103970 A GB6103970 A GB 6103970A GB 1278188 A GB1278188 A GB 1278188A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- cycloalkyl
- sulphides
- sulphur
- dec
- 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
- 150000003568 thioethers Chemical class 0.000 title abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 4
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 abstract 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 abstract 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 abstract 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 239000005864 Sulphur Substances 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- 101100069231 Caenorhabditis elegans gkow-1 gene Proteins 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000001336 alkenes Chemical class 0.000 abstract 1
- 238000006701 autoxidation reaction Methods 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229940069096 dodecene Drugs 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 abstract 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract 1
- 150000002978 peroxides Chemical class 0.000 abstract 1
- 239000002798 polar solvent Substances 0.000 abstract 1
- 229920001021 polysulfide Polymers 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 abstract 1
- 150000004764 thiosulfuric acid derivatives Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1278188 Organic sulphides SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ NV 23 Dec 1970 [30 Dec 1969] 61039/70 Heading C2C Dialkyl sulphides, the term alkyl including cycloalkyl and hydrocarbyl -substituted alkyl or cycloalkyl, are prepared by reacting one or more olefinic compounds with H 2 S in the presence of catalytic quantities of (a) sulphur and/or a dialkyl disulphide (alkyl being as above), and (b) a C 2-12 hydroxyalkylamine of formula where -A-(OH) n is an alkyl or cycloalkyl group having n hydroxy groups as substituents, n being 1 to 3 and not more than one OH group being bound to the same C atom, and R<SP>1</SP> and R<SP>2</SP> are H, alkyl, cycloalkyl or -A-(OH) n . The sulphur may be added in elemental form or may be prepared in situ e.g. from CoS 3 , MoS 2 , Na 2 S 4 , H 2 S 2 , thiosulphates or organic polysulphides or from the H 2 S reactant in combination with SO 2 or as a result of reaction with peroxides formed by autoxidation of the olefin. A polar solvent may be present, e.g. an alcohol, glycol or sulpholane. The reaction may be operated batchwise or continuously with recycle of catalyst and unreacted starting material. The products are predominantly di-sec-alkyl sulphides with some din-alkyl sulphide. Examples prepare di-2-and-1- octyl sulphide from 1-octene. Other specified starting materials are 1-decene, 1-dodecene and styrene.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL6919534A NL6919534A (en) | 1969-12-30 | 1969-12-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1278188A true GB1278188A (en) | 1972-06-14 |
Family
ID=19808728
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB61039/70A Expired GB1278188A (en) | 1969-12-30 | 1970-12-23 | Process for the preparation of dialkyl sulphides |
Country Status (4)
| Country | Link |
|---|---|
| DE (1) | DE2063919A1 (en) |
| FR (1) | FR2074349A5 (en) |
| GB (1) | GB1278188A (en) |
| NL (1) | NL6919534A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4119550A (en) * | 1975-03-21 | 1978-10-10 | The Lubrizol Corporation | Sulfurized compositions |
| US4119549A (en) * | 1975-03-21 | 1978-10-10 | The Lubrizol Corporation | Sulfurized compositions |
| US4191659A (en) * | 1975-03-21 | 1980-03-04 | The Lubrizol Corporation | Sulfurized compositions |
-
1969
- 1969-12-30 NL NL6919534A patent/NL6919534A/xx unknown
-
1970
- 1970-12-23 GB GB61039/70A patent/GB1278188A/en not_active Expired
- 1970-12-28 DE DE19702063919 patent/DE2063919A1/en active Pending
- 1970-12-28 FR FR7046842A patent/FR2074349A5/fr not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4119550A (en) * | 1975-03-21 | 1978-10-10 | The Lubrizol Corporation | Sulfurized compositions |
| US4119549A (en) * | 1975-03-21 | 1978-10-10 | The Lubrizol Corporation | Sulfurized compositions |
| US4191659A (en) * | 1975-03-21 | 1980-03-04 | The Lubrizol Corporation | Sulfurized compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6919534A (en) | 1970-03-23 |
| DE2063919A1 (en) | 1971-07-01 |
| FR2074349A5 (en) | 1971-10-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |