GB591283A - Process for the preparation of sulfides of alkylated phenols - Google Patents
Process for the preparation of sulfides of alkylated phenolsInfo
- Publication number
- GB591283A GB591283A GB119345A GB119345A GB591283A GB 591283 A GB591283 A GB 591283A GB 119345 A GB119345 A GB 119345A GB 119345 A GB119345 A GB 119345A GB 591283 A GB591283 A GB 591283A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenol
- phenols
- chlorinated
- catalyst
- boron
- 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
- 150000002989 phenols Chemical class 0.000 title abstract 3
- 150000003568 thioethers Chemical class 0.000 title 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 9
- WTEOIRVLGSZEPR-UHFFFAOYSA-N Boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 abstract 4
- 239000003054 catalyst Substances 0.000 abstract 4
- -1 boron halide Chemical class 0.000 abstract 3
- 239000003208 petroleum Substances 0.000 abstract 3
- FWMUJAIKEJWSSY-UHFFFAOYSA-N Sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 abstract 2
- 229910052796 boron Inorganic materials 0.000 abstract 2
- 239000007789 gas Substances 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 235000019271 petrolatum Nutrition 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- HPSUPGAVFFFPMQ-UHFFFAOYSA-N 1,2,3,4,6,7,10-heptachlorododecane Chemical compound CCC(Cl)CCC(Cl)C(Cl)CC(Cl)C(Cl)C(Cl)CCl HPSUPGAVFFFPMQ-UHFFFAOYSA-N 0.000 abstract 1
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 abstract 1
- LZSAGXFRFKMHFS-UHFFFAOYSA-N OC1=CC2C(C=C1)(O)S2 Chemical class OC1=CC2C(C=C1)(O)S2 LZSAGXFRFKMHFS-UHFFFAOYSA-N 0.000 abstract 1
- 229940066842 Petrolatum Drugs 0.000 abstract 1
- 239000004264 Petrolatum Substances 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 230000002152 alkylating Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N benzohydroquinone Chemical class OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 238000005755 formation reaction Methods 0.000 abstract 1
- 239000003350 kerosene Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000012188 paraffin wax Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 238000007670 refining Methods 0.000 abstract 1
- 239000010802 sludge Substances 0.000 abstract 1
- 239000007858 starting material 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
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/086—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing sulfur atoms bound to carbon atoms of six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Alkylated monohydroxy phenol sulphides are prepared by alkylating a phenol with an olefine in the presence of a boron halide catalyst, dissolving the reaction product containing the catalyst in an organic solvent and treating the solution with a sulphur halide. In addition to the monohydroxy phenols as starting materials there may also be used high molecular weight alkylated phenols prepared by condensing phenols with chlorinated petrolatum or chlorinated paraffin wax or with a chlorinated kerosene or gas oil. The alkylation is preferably carried out by first adding the boron halide catalyst to the phenol and then introducing the olefine. This is stated to avoid sludge formation. As olefines there may be used individual olefines or mixtures derived from petroleum and refining gases. The preferred catalysts are boron trifluoride and combinations of boron trifluoride with water and with phosphoric acid. For the sulphurization the preferred reagents are sulphur chloride in a petroleum naphtha solvent. An example is included in which tertiaryoctyl phenol is produced by the reaction of diisobutylene on phenol and the product sulphurized with sulphur chloride in a petroleum naphtha solvent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US541299A US2398253A (en) | 1944-06-20 | 1944-06-20 | Sulphides of alkylated phenols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB591283A true GB591283A (en) | 1947-08-13 |
Family
ID=1626710
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB119345A Expired GB591283A (en) | 1944-06-20 | 1945-01-15 | Process for the preparation of sulfides of alkylated phenols |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB591283A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2936288A1 (en) * | 1978-09-07 | 1980-03-20 | Mitsui Toatsu Chemicals | METHOD FOR PRODUCING 2,2'-SQUARE BRACE TO 4-(1,1,3,3-TETRAMETHYLBUTYL)-PHENOL SQUARE BRACE TO SULFIDE |
| DE2937294A1 (en) * | 1978-09-14 | 1980-04-03 | Mitsui Toatsu Chemicals | METHOD FOR PRODUCING 2,2'-BIS (4-SUBSTITUTED PHENOL) SULFIDES |
| US5330667A (en) * | 1992-04-15 | 1994-07-19 | Exxon Chemical Patents Inc. | Two-cycle oil additive |
-
1945
- 1945-01-15 GB GB119345A patent/GB591283A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2936288A1 (en) * | 1978-09-07 | 1980-03-20 | Mitsui Toatsu Chemicals | METHOD FOR PRODUCING 2,2'-SQUARE BRACE TO 4-(1,1,3,3-TETRAMETHYLBUTYL)-PHENOL SQUARE BRACE TO SULFIDE |
| DE2937294A1 (en) * | 1978-09-14 | 1980-04-03 | Mitsui Toatsu Chemicals | METHOD FOR PRODUCING 2,2'-BIS (4-SUBSTITUTED PHENOL) SULFIDES |
| FR2436137A1 (en) * | 1978-09-14 | 1980-04-11 | Mitsui Toatsu Chemicals | PROCESS FOR THE PREPARATION OF SULPHIDES OF 2,2'-BIS (PHENOL SUBSTITUTED IN 4) |
| US5330667A (en) * | 1992-04-15 | 1994-07-19 | Exxon Chemical Patents Inc. | Two-cycle oil additive |
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