GB858890A - Process of producing crystalline ortho, ortho-bis(para-1,1,3,3-tetramethylbutylphenol) monosulphide and nickel derivatives thereof - Google Patents
Process of producing crystalline ortho, ortho-bis(para-1,1,3,3-tetramethylbutylphenol) monosulphide and nickel derivatives thereofInfo
- Publication number
- GB858890A GB858890A GB1897059A GB1897059A GB858890A GB 858890 A GB858890 A GB 858890A GB 1897059 A GB1897059 A GB 1897059A GB 1897059 A GB1897059 A GB 1897059A GB 858890 A GB858890 A GB 858890A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tetramethylbutylphenol
- ortho
- monosulphide
- bis
- crystalline
- 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
- 150000002815 nickel Chemical class 0.000 title abstract 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 6
- FZCXLIJHQIVORT-UHFFFAOYSA-N 3-(2,3,3-trimethylpentan-2-yl)phenol Chemical compound CCC(C)(C)C(C)(C)C1=CC=CC(O)=C1 FZCXLIJHQIVORT-UHFFFAOYSA-N 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 3
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 2
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000007791 liquid phase Substances 0.000 abstract 1
- 229940078487 nickel acetate tetrahydrate Drugs 0.000 abstract 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 abstract 1
- OINIXPNQKAZCRL-UHFFFAOYSA-L nickel(2+);diacetate;tetrahydrate Chemical compound O.O.O.O.[Ni+2].CC([O-])=O.CC([O-])=O OINIXPNQKAZCRL-UHFFFAOYSA-L 0.000 abstract 1
- 239000012188 paraffin wax Substances 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/04—Nickel compounds
- C07F15/045—Nickel compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/375—Thiols containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Crystalline o : o1-bis (p-1 : 1 : 3 : 3-tetramethylbutylphenol)-monosulphide is prepared by reacting a solution of crystalline p-1 : 1 : 3 : 3-tetramethylbutylphenol with sulphur dichloride until evolution of hydrogen chloride closes and recovering the product by removal of the liquid phase. In Examples: (1) p-1 : 1 : 3 : 3-tetramethylbutylphenol is dissolved in a paraffin solvent with heating, sulphur dichloride is added, the mixture heated to drive off hydrogen chloride, cooled and the crystalline o : o1-bis (p-1 : 1 : 3 : 3-tetramethylbutyl)monosulphide filtered off; (2) p-1 : 1 : 3 : 3-tetramethylbutylphenol is dissolved in carbon tetrachloride, the mixture is cooled and agitated, a solution of sulphur dichloride in carbon tetrachloride is added, the mixture is stood overnight, washed with water, boiled to remove the carbon tetrachloride, cooled, diluted with petroleum ether, and the sulphide filtered off. The nickel salts may be prepared by reacting the sulphide first with sodium ethoxide and then with nickel chloride, or directly with nickel acetate tetrahydrate.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US789908A US2971968A (en) | 1959-01-29 | 1959-01-29 | Ortho, ortho'-bis (para-1, 1, 3, 3-tetramethyl-butylphenol) monosulphide |
| US813459A US2971941A (en) | 1959-05-15 | 1959-05-15 | Nickel bis-(p-octylphenol) monosulphide stabilized polyethylene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB858890A true GB858890A (en) | 1961-01-18 |
Family
ID=27120969
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1897059A Expired GB858890A (en) | 1959-01-29 | 1959-06-03 | Process of producing crystalline ortho, ortho-bis(para-1,1,3,3-tetramethylbutylphenol) monosulphide and nickel derivatives thereof |
| GB1896959A Expired GB914336A (en) | 1959-01-29 | 1959-06-03 | Improvements relating to the stabilization of polyethylene |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1896959A Expired GB914336A (en) | 1959-01-29 | 1959-06-03 | Improvements relating to the stabilization of polyethylene |
Country Status (3)
| Country | Link |
|---|---|
| DE (2) | DE1141785B (en) |
| FR (2) | FR1235590A (en) |
| GB (2) | GB858890A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0001911A1 (en) * | 1977-10-28 | 1979-05-16 | Mobil Oil Corporation | Reaction product of nickel thiobis(alkylphenolate) and thiobisphenol or thiobis(alkylphenol) and organic compositions containing the same |
| FR2435468A1 (en) * | 1978-09-07 | 1980-04-04 | Mitsui Toatsu Chemicals | PROCESS FOR THE PREPARATION OF SULFIDE OF 2,2'-BIS (4- (1,1,3,3-TETRAMETHYLBUTYL) PHENOL) |
| EP0072489A1 (en) * | 1981-08-17 | 1983-02-23 | Agfa-Gevaert AG | Photographic material with a layer dyeable by organic dyestuffs |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108623640B (en) * | 2018-07-03 | 2021-03-02 | 乐凯化学材料有限公司 | Preparation method of 2, 2' -thiobis (4-tert-octylphenol) n-butylamine nickel |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR824600A (en) * | 1936-08-01 | 1938-02-11 | Standard Oil Dev Co | Anti-oxidants for lubricating oils |
| DE753626C (en) * | 1939-01-04 | 1953-04-09 | Ig Farbenindustrie Ag | Process for improving the antioxidant effect of alkylphenol sulfides |
| US2362293A (en) * | 1939-12-27 | 1944-11-07 | Standard Oil Dev Co | Lubricant |
| US2340938A (en) * | 1940-11-30 | 1944-02-08 | Standard Oil Dev Co | Stabilized high molecular weight hydrocarbon polymer |
| US2370756A (en) * | 1942-06-09 | 1945-03-06 | Monsanto Chemicals | Sulphides of dialkyl phenols |
| GB780289A (en) * | 1954-09-30 | 1957-07-31 | Du Pont | Improvements in or relating to polyethyleí¡ extrusion compositions |
| GB772938A (en) * | 1954-10-28 | 1957-04-17 | Union Carbide & Carbon Corp | Stabilization of polyethylene |
-
1959
- 1959-06-03 GB GB1897059A patent/GB858890A/en not_active Expired
- 1959-06-03 GB GB1896959A patent/GB914336A/en not_active Expired
- 1959-06-11 FR FR797259A patent/FR1235590A/en not_active Expired
- 1959-06-18 DE DEF28719A patent/DE1141785B/en active Pending
- 1959-06-18 DE DEF28720A patent/DE1275067B/en active Pending
-
1960
- 1960-01-28 FR FR816980A patent/FR1247084A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0001911A1 (en) * | 1977-10-28 | 1979-05-16 | Mobil Oil Corporation | Reaction product of nickel thiobis(alkylphenolate) and thiobisphenol or thiobis(alkylphenol) and organic compositions containing the same |
| FR2435468A1 (en) * | 1978-09-07 | 1980-04-04 | Mitsui Toatsu Chemicals | PROCESS FOR THE PREPARATION OF SULFIDE OF 2,2'-BIS (4- (1,1,3,3-TETRAMETHYLBUTYL) PHENOL) |
| EP0072489A1 (en) * | 1981-08-17 | 1983-02-23 | Agfa-Gevaert AG | Photographic material with a layer dyeable by organic dyestuffs |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1275067B (en) | 1968-08-14 |
| DE1141785B (en) | 1962-12-27 |
| FR1247084A (en) | 1960-11-25 |
| GB914336A (en) | 1963-01-02 |
| FR1235590A (en) | 1960-07-08 |
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