GB1425278A - Process for producing mercaptophenols engine exhaust brake unit for vehicles with combustible gas- operated ottocycle internal combustion engines - Google Patents
Process for producing mercaptophenols engine exhaust brake unit for vehicles with combustible gas- operated ottocycle internal combustion enginesInfo
- Publication number
- GB1425278A GB1425278A GB1049874A GB1049874A GB1425278A GB 1425278 A GB1425278 A GB 1425278A GB 1049874 A GB1049874 A GB 1049874A GB 1049874 A GB1049874 A GB 1049874A GB 1425278 A GB1425278 A GB 1425278A
- Authority
- GB
- United Kingdom
- Prior art keywords
- mercaptophenols
- dimethylphenol
- mercapto
- ottocycle
- vehicles
- 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
- VMKYTRPNOVFCGZ-UHFFFAOYSA-N 2-sulfanylphenol Chemical class OC1=CC=CC=C1S VMKYTRPNOVFCGZ-UHFFFAOYSA-N 0.000 title abstract 5
- 238000002485 combustion reaction Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 abstract 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 150000002989 phenols Chemical class 0.000 abstract 2
- 239000002798 polar solvent Substances 0.000 abstract 2
- 239000011541 reaction mixture Substances 0.000 abstract 2
- LPBKQTBJECPETB-UHFFFAOYSA-N 2,4-dimethyl-6-sulfanylphenol Chemical compound CC1=CC(C)=C(O)C(S)=C1 LPBKQTBJECPETB-UHFFFAOYSA-N 0.000 abstract 1
- KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 abstract 1
- IEQAUACQFUWVAH-UHFFFAOYSA-N 2,6-dimethyl-4-sulfanylphenol Chemical compound CC1=CC(S)=CC(C)=C1O IEQAUACQFUWVAH-UHFFFAOYSA-N 0.000 abstract 1
- NIFAOMSJMGEFTQ-UHFFFAOYSA-N 4-methoxybenzenethiol Chemical compound COC1=CC=C(S)C=C1 NIFAOMSJMGEFTQ-UHFFFAOYSA-N 0.000 abstract 1
- MNVMYTVDDOXZLS-UHFFFAOYSA-N 4-methoxyguaiacol Natural products COC1=CC=C(O)C(OC)=C1 MNVMYTVDDOXZLS-UHFFFAOYSA-N 0.000 abstract 1
- HTNBBGMFIFDMFW-UHFFFAOYSA-N 4-sulfanylbenzene-1,2-diol Chemical compound OC1=CC=C(S)C=C1O HTNBBGMFIFDMFW-UHFFFAOYSA-N 0.000 abstract 1
- BXAVKNRWVKUTLY-UHFFFAOYSA-N 4-sulfanylphenol Chemical compound OC1=CC=C(S)C=C1 BXAVKNRWVKUTLY-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 abstract 1
- 229920001021 polysulfide Polymers 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 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
- C07C319/06—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols from sulfides, hydropolysulfides or polysulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/22—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides
- C07C319/24—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides by reactions involving the formation of sulfur-to-sulfur bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1425278 Mercaptophenols CROWN ZEL LERBACH CORP 8 March 1974 [12 March 1973] 10498/74 Heading C2C Mercaptophenols are produced from phenols by contacting at least one phenol having the Formula (I): in which R is hydrogen or an alkyl, cycloalkyl or haloalkyl group containing up to 10 carbon atoms, and -R<SP>1</SP> n represents up to 4 optional substituents, each being halogen or a hydroxy group or an alkyl, alkoxy, aryl or cycloalkyl group each containing up to 20 carbon atoms, provided at least one position ortho or para to the OR group is occupied by a hydrogen atom, with a sulphur chloride in a polar solvent having a "water solubility" of at least 2À0, the phenols comprising up to 25% by weight of the reaction mixture; reducing the resulting polysulphides to mercaptophenols; and isolating the mercaptophenols from the reaction mixture. The polar solvent is defined as one which has a solubility in water of at least 2À0 based on grams of solvent dissolved per 100 gms. of water at a temperature of approximately 25‹ C. If desired, hydrogen chloride may be used as a promoter. Examples describe the conversion of (a) phenol to 4-mercaptophenol; (b) 2,4-dimethylphenol to 6- mercapto - 2,4 - dimethylphenol; (c) 2,6-dimethylphenol to 4 - mercapto - 2,6 - dimethylphenol; (c) anisole to 4-mercapto-anisole; and (d) catechol to 4-mercaptocatechol.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34062773A | 1973-03-12 | 1973-03-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1425278A true GB1425278A (en) | 1976-02-18 |
Family
ID=23334251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1049874A Expired GB1425278A (en) | 1973-03-12 | 1974-03-08 | Process for producing mercaptophenols engine exhaust brake unit for vehicles with combustible gas- operated ottocycle internal combustion engines |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5024233A (en) |
| CA (1) | CA1024532A (en) |
| CH (1) | CH585707A5 (en) |
| DE (1) | DE2411826A1 (en) |
| FR (1) | FR2221445B1 (en) |
| GB (1) | GB1425278A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0200212A2 (en) * | 1985-04-30 | 1986-11-05 | Sumitomo Seika Chemicals Co., Ltd. | Process for producing polythiobisphenols and process for producing mercaptophenols by the hydrogenolysis of the same |
| US4734527A (en) * | 1986-10-17 | 1988-03-29 | Merrell Dow Pharmaceuticals Inc. | Process for preparing 2,6-di-tertiarybutyl-4-mercaptophenol |
| US4772363A (en) * | 1987-01-14 | 1988-09-20 | Merrell Dow Pharmaceuticals Inc. | Process for preparing 2,6-di-tertiarybutyl-4-mercaptophenol by electrocatalysis |
| US5401883A (en) * | 1987-01-20 | 1995-03-28 | Merrell Dow Pharmaceuticals Inc. | Process for preparing 2,6-di-tertiarybutyl-4-mercaptophenol and 4,4'-isopropylidenedithio-bis-(2,6-di-tertiarybutylphenol) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4056568A (en) * | 1975-03-24 | 1977-11-01 | Crown Zellerbach Corporation | 2,6-Dialkyl-4-hydroxysulfenyl chlorides |
| GB2031422B (en) * | 1978-09-14 | 1983-05-11 | Mitsui Toatsu Chemicals | Preparation of 2,2'-bis(4-substituted-phenol sulfides |
| US4672138A (en) * | 1980-10-20 | 1987-06-09 | Hoechst Roussel Pharmaceuticals Inc. | Phenyl substituted carbamothioic acid esters |
| US4436748A (en) * | 1980-10-20 | 1984-03-13 | Hoechst-Roussel Pharmaceuticals Inc. | Benzo[b]thiophenes |
| JPH0813797B2 (en) * | 1987-01-24 | 1996-02-14 | 住友精化株式会社 | Process for producing 4-methyl-1,2-benzenedithiol |
| US4946610A (en) * | 1989-08-03 | 1990-08-07 | Ethyl Petroleum Additives, Inc. | Sulfur-bridged phenolic antioxidants |
-
1974
- 1974-03-08 GB GB1049874A patent/GB1425278A/en not_active Expired
- 1974-03-08 FR FR7408793A patent/FR2221445B1/fr not_active Expired
- 1974-03-12 CA CA194,736A patent/CA1024532A/en not_active Expired
- 1974-03-12 JP JP2845874A patent/JPS5024233A/ja active Pending
- 1974-03-12 DE DE19742411826 patent/DE2411826A1/en not_active Withdrawn
- 1974-03-12 CH CH341474A patent/CH585707A5/xx not_active IP Right Cessation
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0200212A2 (en) * | 1985-04-30 | 1986-11-05 | Sumitomo Seika Chemicals Co., Ltd. | Process for producing polythiobisphenols and process for producing mercaptophenols by the hydrogenolysis of the same |
| EP0200212A3 (en) * | 1985-04-30 | 1988-08-24 | Seitetsu Kagaku Co., Ltd. | Process for producing polythiobisphenols and process for producing mercaptophenols by the hydrogenolysis of the same |
| EP0474259A2 (en) * | 1985-04-30 | 1992-03-11 | Sumitomo Seika Chemicals Co., Ltd. | Process for producing mercaptophenols by the hydrogenolysis of polythiobisphenols |
| EP0474259A3 (en) * | 1985-04-30 | 1992-04-22 | Seitetsu Kagaku Co. Ltd. | Process for producing mercaptophenols by the hydrogenolysis of polythiobisphenols |
| US4734527A (en) * | 1986-10-17 | 1988-03-29 | Merrell Dow Pharmaceuticals Inc. | Process for preparing 2,6-di-tertiarybutyl-4-mercaptophenol |
| US4772363A (en) * | 1987-01-14 | 1988-09-20 | Merrell Dow Pharmaceuticals Inc. | Process for preparing 2,6-di-tertiarybutyl-4-mercaptophenol by electrocatalysis |
| US5401883A (en) * | 1987-01-20 | 1995-03-28 | Merrell Dow Pharmaceuticals Inc. | Process for preparing 2,6-di-tertiarybutyl-4-mercaptophenol and 4,4'-isopropylidenedithio-bis-(2,6-di-tertiarybutylphenol) |
Also Published As
| Publication number | Publication date |
|---|---|
| CH585707A5 (en) | 1977-03-15 |
| CA1024532A (en) | 1978-01-17 |
| FR2221445B1 (en) | 1979-04-20 |
| JPS5024233A (en) | 1975-03-15 |
| FR2221445A1 (en) | 1974-10-11 |
| DE2411826A1 (en) | 1974-09-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |