CA1139259A - Process for preparing 2-alkoxyethyl mercaptans - Google Patents
Process for preparing 2-alkoxyethyl mercaptansInfo
- Publication number
- CA1139259A CA1139259A CA000352868A CA352868A CA1139259A CA 1139259 A CA1139259 A CA 1139259A CA 000352868 A CA000352868 A CA 000352868A CA 352868 A CA352868 A CA 352868A CA 1139259 A CA1139259 A CA 1139259A
- Authority
- CA
- Canada
- Prior art keywords
- vinyl ether
- reaction
- alkoxyethyl
- mercaptan
- mercaptans
- 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
- 238000004519 manufacturing process Methods 0.000 title abstract description 6
- -1 alkyl vinyl ether Chemical compound 0.000 claims abstract description 7
- 239000007791 liquid phase Substances 0.000 claims abstract description 6
- 230000005855 radiation Effects 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 12
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical group COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 claims description 10
- VHXDADVHQVXSKC-UHFFFAOYSA-N 2-methoxyethanethiol Chemical group COCCS VHXDADVHQVXSKC-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- SKYXLDSRLNRAPS-UHFFFAOYSA-N 1,2,4-trifluoro-5-methoxybenzene Chemical group COC1=CC(F)=C(F)C=C1F SKYXLDSRLNRAPS-UHFFFAOYSA-N 0.000 claims description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- JEOQACOXAOEPLX-WCCKRBBISA-N (2s)-2-amino-5-(diaminomethylideneamino)pentanoic acid;1,3-thiazolidine-4-carboxylic acid Chemical compound OC(=O)C1CSCN1.OC(=O)[C@@H](N)CCCN=C(N)N JEOQACOXAOEPLX-WCCKRBBISA-N 0.000 claims 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract description 11
- 229910000037 hydrogen sulfide Inorganic materials 0.000 abstract description 11
- 239000000273 veterinary drug Substances 0.000 abstract description 3
- 239000004615 ingredient Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 9
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- NSBQEXGAGSBJGY-UHFFFAOYSA-N 2-butoxyethanethiol Chemical compound CCCCOCCS NSBQEXGAGSBJGY-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 239000012808 vapor phase Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LAYAKLSFVAPMEL-UHFFFAOYSA-N 1-ethenoxydodecane Chemical compound CCCCCCCCCCCCOC=C LAYAKLSFVAPMEL-UHFFFAOYSA-N 0.000 description 1
- XXCVIFJHBFNFBO-UHFFFAOYSA-N 1-ethenoxyoctane Chemical compound CCCCCCCCOC=C XXCVIFJHBFNFBO-UHFFFAOYSA-N 0.000 description 1
- UNBYWYATNFOIAZ-UHFFFAOYSA-N 2-dodecoxyethanethiol Chemical compound CCCCCCCCCCCCOCCS UNBYWYATNFOIAZ-UHFFFAOYSA-N 0.000 description 1
- RRZWEKHXRJYDRV-UHFFFAOYSA-N 2-octadecoxyethanethiol Chemical compound CCCCCCCCCCCCCCCCCCOCCS RRZWEKHXRJYDRV-UHFFFAOYSA-N 0.000 description 1
- PIFZZFPFFSPLLJ-UHFFFAOYSA-N 2-octoxyethanethiol Chemical compound CCCCCCCCOCCS PIFZZFPFFSPLLJ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical class CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
Classifications
-
- 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
- C07C319/04—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols by addition of hydrogen sulfide or its salts to unsaturated compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4349779A | 1979-05-29 | 1979-05-29 | |
| US043,497 | 1979-05-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1139259A true CA1139259A (en) | 1983-01-11 |
Family
ID=21927460
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000352868A Expired CA1139259A (en) | 1979-05-29 | 1980-05-28 | Process for preparing 2-alkoxyethyl mercaptans |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5632451A (OSRAM) |
| BE (1) | BE883505A (OSRAM) |
| CA (1) | CA1139259A (OSRAM) |
| DE (1) | DE3020488A1 (OSRAM) |
| FR (1) | FR2457856A1 (OSRAM) |
| GB (1) | GB2049669B (OSRAM) |
| IT (1) | IT1144063B (OSRAM) |
| NL (1) | NL8002178A (OSRAM) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4942848A (en) * | 1987-04-30 | 1990-07-24 | Nissan Motor Co., Ltd. | Air-fuel ratio control system for automotive internal combustion engine or the like with fuel type discrimination capabilities |
| US7404928B2 (en) * | 2002-07-29 | 2008-07-29 | The United States Of America As Represented By The Secretary Of The Navy | Thiol terminated monodisperse ethylene oxide oligomer capped gold nanoclusters |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL34486A (en) * | 1969-06-04 | 1973-10-25 | Stauffer Chemical Co | The preparation of mercaptans |
-
1980
- 1980-03-28 GB GB8010627A patent/GB2049669B/en not_active Expired
- 1980-04-15 NL NL8002178A patent/NL8002178A/nl not_active Application Discontinuation
- 1980-05-12 IT IT48653/80A patent/IT1144063B/it active
- 1980-05-28 FR FR8011823A patent/FR2457856A1/fr active Granted
- 1980-05-28 CA CA000352868A patent/CA1139259A/en not_active Expired
- 1980-05-28 BE BE0/200784A patent/BE883505A/fr not_active IP Right Cessation
- 1980-05-28 JP JP7023880A patent/JPS5632451A/ja active Pending
- 1980-05-29 DE DE19803020488 patent/DE3020488A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| GB2049669B (en) | 1983-09-07 |
| BE883505A (fr) | 1980-09-15 |
| IT1144063B (it) | 1986-10-29 |
| IT8048653A0 (it) | 1980-05-12 |
| FR2457856A1 (fr) | 1980-12-26 |
| JPS5632451A (en) | 1981-04-01 |
| DE3020488A1 (de) | 1980-12-11 |
| NL8002178A (nl) | 1980-12-02 |
| FR2457856B1 (OSRAM) | 1985-04-26 |
| GB2049669A (en) | 1980-12-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |