GB558790A - Preparation of organic sulphur compounds - Google Patents
Preparation of organic sulphur compoundsInfo
- Publication number
- GB558790A GB558790A GB3515/42A GB351542A GB558790A GB 558790 A GB558790 A GB 558790A GB 3515/42 A GB3515/42 A GB 3515/42A GB 351542 A GB351542 A GB 351542A GB 558790 A GB558790 A GB 558790A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrogen sulphide
- butene
- march
- reacted
- quartz
- 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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical class [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title abstract 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 6
- 239000010453 quartz Substances 0.000 abstract 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 abstract 2
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 abstract 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 abstract 2
- -1 amylenes Chemical compound 0.000 abstract 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 abstract 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 abstract 2
- ILLHQJIJCRNRCJ-UHFFFAOYSA-N dec-1-yne Chemical group CCCCCCCCC#C ILLHQJIJCRNRCJ-UHFFFAOYSA-N 0.000 abstract 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 abstract 2
- 229910052753 mercury Inorganic materials 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- 150000003568 thioethers Chemical class 0.000 abstract 2
- DUKJZYZDOKKAMU-UHFFFAOYSA-N 1-chloronaphthalene-2-carbaldehyde Chemical compound C1=CC=C2C(Cl)=C(C=O)C=CC2=C1 DUKJZYZDOKKAMU-UHFFFAOYSA-N 0.000 abstract 1
- RDGFNMCPRYSKTF-UHFFFAOYSA-N 3-chlorobutane-2-thiol Chemical compound CC(S)C(C)Cl RDGFNMCPRYSKTF-UHFFFAOYSA-N 0.000 abstract 1
- UZPWKTCMUADILM-UHFFFAOYSA-N 3-methylcyclohexene Chemical compound CC1CCCC=C1 UZPWKTCMUADILM-UHFFFAOYSA-N 0.000 abstract 1
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 abstract 1
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- ZERULLAPCVRMCO-UHFFFAOYSA-N Dipropyl sulfide Chemical compound CCCSCCC ZERULLAPCVRMCO-UHFFFAOYSA-N 0.000 abstract 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 abstract 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 abstract 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 229940052303 ethers for general anesthesia Drugs 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 230000000855 fungicidal effect Effects 0.000 abstract 1
- 230000002070 germicidal effect Effects 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- CNFQJGLKUZBUBD-TXHUMJEOSA-N hexa-1,5-diene;(3e)-hexa-1,3-diene;(4e)-hexa-1,4-diene Chemical class CC\C=C\C=C.C\C=C\CC=C.C=CCCC=C CNFQJGLKUZBUBD-TXHUMJEOSA-N 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 230000000749 insecticidal effect Effects 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 239000007791 liquid phase Substances 0.000 abstract 1
- 150000002894 organic compounds Chemical class 0.000 abstract 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N pentadiene group Chemical class C=CC=CC PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 229920000098 polyolefin Polymers 0.000 abstract 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 abstract 1
- 230000005855 radiation Effects 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 229960000834 vinyl ether Drugs 0.000 abstract 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/16—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides 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)
Abstract
558,790. Sulphur derivatives. SHELL DEVELOPMENT CO. March 17, 1942, Nos. 3515 and 3516. Convention dates, March 28, 1941 and March 29. 1941. [Class 2 (iii)] Mercaptans and thioethers are produced by treating organic compounds containing an unsaturated linkage of aliphatic character with hydrogen sulphide under the influence of ultra violet radiations. In examples : (1) butene-1 is reacted with hydrogen sulphide in a quartz reactor while irradiated with rays from a quartz mercury arc lamp at temperatures above and below 0‹C. ; (2) propylene is reacted with hydrogen sulphide to give a mixture of npropyl mercaptan and di-n-propylthioether and methyl acrylate similarly treated gives #-thiolpropionic acid and its thioether; (3) hydrogen sulphide is reacted with vinyl chloride at 0‹C. and below, in an air free quartz reactor, in the liquid phase while irradiated with a quartz mercury arc lamp; a mixture of ethylenethiochlorhydrin and mustard gas is obtained ; (4) 2-chlor-3-mercaptobutane is produced by treating 2-chlorbutane-2 with hydrogen sulphide under similar conditions. The products are stated to have insecticidal, germicidal, fungicidal, vesicatory, sternutatory and lachrymal properties. The unsaturated starting materials may be olefines, polyolefines or olefine polymers obtained from petroleum and halides, alcohols, ethers and esters having at least one olefinic linkage. Starting materials mentioned include : ethylene, isobutylene, amylenes, 4-methylpentene-1, cetene-1, styrene, cyclohexene, 3-methylcyclohexene, 1:4-diphenyl butene-2, butadiene-1:3, pentadienes, hexadienes, acetylene, propyne, cetyne, octylacetylene and phenylacetylene. These hydrocarbons may contain as substituents : chlorine, bromine, iodine and fluorine and alkoxy, aralkoxy and alkylimido groups. Further specified compounds are : allylhalides, isocrotylhalides, 4-halogenbutene-1, monohalogenated acetylenes, propargylhalides, 1:1-dihaloethylene, trihalogenethylene, 3-halopentene- 1, 3 - halocyclohexene, 2 - halo - 1:4 - diphenyl - butene - 2, 3 - halopentadiene - 1:4, divinyl - ether, diallylether, dimethallylether and allylalcohol.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US558790XA | 1956-06-29 | 1956-06-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB558790A true GB558790A (en) | 1944-01-21 |
Family
ID=22000768
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3515/42A Expired GB558790A (en) | 1941-03-28 | 1942-03-17 | Preparation of organic sulphur compounds |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE558790A (en) |
| GB (1) | GB558790A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2497100A (en) * | 1947-05-09 | 1950-02-14 | Phillips Petroleum Co | Mercapto-alkoxy thio-ethers |
| US2497422A (en) * | 1947-05-09 | 1950-02-14 | Phillips Petroleum Co | Production of alkoxy thiols |
| US2562145A (en) * | 1947-07-29 | 1951-07-24 | Shell Dev | Preparation of saturated sulfurcontaining heterocyclic compounds |
| EP0801056A2 (en) * | 1996-04-10 | 1997-10-15 | Elf Atochem North America, Inc. | Preparation of primary mercaptans |
| RU2781096C1 (en) * | 2021-09-07 | 2022-10-05 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Башкирский государственный университет" | Piperylene processing method |
-
1942
- 1942-03-17 GB GB3515/42A patent/GB558790A/en not_active Expired
-
1957
- 1957-06-28 BE BE558790A patent/BE558790A/en unknown
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2497100A (en) * | 1947-05-09 | 1950-02-14 | Phillips Petroleum Co | Mercapto-alkoxy thio-ethers |
| US2497422A (en) * | 1947-05-09 | 1950-02-14 | Phillips Petroleum Co | Production of alkoxy thiols |
| US2562145A (en) * | 1947-07-29 | 1951-07-24 | Shell Dev | Preparation of saturated sulfurcontaining heterocyclic compounds |
| EP0801056A2 (en) * | 1996-04-10 | 1997-10-15 | Elf Atochem North America, Inc. | Preparation of primary mercaptans |
| EP0801056A3 (en) * | 1996-04-10 | 1998-08-12 | Elf Atochem North America, Inc. | Preparation of primary mercaptans |
| RU2781096C1 (en) * | 2021-09-07 | 2022-10-05 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Башкирский государственный университет" | Piperylene processing method |
Also Published As
| Publication number | Publication date |
|---|---|
| BE558790A (en) | 1960-04-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2212786A (en) | Production of sulphonyl chlorides of olefin polymers | |
| US2392294A (en) | Photochemical preparation of thio-ethers | |
| Oswald et al. | Organic sulfur compounds. VIII. Addition of thiols to conjugated diolefins | |
| US2398479A (en) | Preparation of organic sulphur compounds | |
| Cristol et al. | Bridged Polycyclic Compounds. XXV. Free-Radical Addition of Benzenesulfonyl Halides to Norbornadiene1 | |
| GB558790A (en) | Preparation of organic sulphur compounds | |
| GB627773A (en) | Improvements in or relating to the production of organic fluorine compounds | |
| CA1118712A (en) | Process for preparing mercaptans | |
| US2522590A (en) | Photochemical reaction of unsaturated ethers with aliphatic mercaptans | |
| Walling et al. | The Peroxide Effect in the Addition of Reagents to Unsaturated Substances. XXII. The Addition of Hydrogen Bromide to Trimethylethylene, Styrene, Crotonic Acid, and Ethyl Crotonate | |
| US2446124A (en) | Reaction of hydrogen halides with compounds having aliphatic unsaturation | |
| GB842416A (en) | Manufacture of halogen-containing polyolefines | |
| Poutsma et al. | Chlorination studies of unsaturated materials in nonpolar media—VI: Photochlorination of 1-butyne | |
| Priest et al. | Colored Complexes of Tungsten Hexafluoride with Organic Compounds | |
| US3085955A (en) | Production of sulfur compounds | |
| US2383091A (en) | Method of making halogenated ethers | |
| GB682771A (en) | Improvements in or relating to the copolymerization of aromatic divinyl compounds and isobutylene | |
| GB593036A (en) | Modified olefinic polymers | |
| US3019267A (en) | Thiols of bicyclo [2. 2. 1] hepta-2, 5-diene and method of preparation | |
| US2503253A (en) | Azo catalysts in preparation of sulfonyl chlorides | |
| GB567524A (en) | Process for effecting abnormal addition of hydrogen halide, hydrogen sulfide and mercaptans | |
| Van Langhout et al. | The addition of hydrogen sulphide to alkenes | |
| GB843234A (en) | Production of hydrobrominated derivatives of olefinically unsaturated compounds | |
| GB855714A (en) | Halogenated and/or sulphohalogenated copolymers of lower olefines and process for their manufacture | |
| GB610703A (en) | Improvements in the processing of hydrocarbons |