GB838928A - Oxyalkylated phosphosulphurised hydrocarbons and lubricating compositions therefrom - Google Patents
Oxyalkylated phosphosulphurised hydrocarbons and lubricating compositions therefromInfo
- Publication number
- GB838928A GB838928A GB34092/58A GB3409258A GB838928A GB 838928 A GB838928 A GB 838928A GB 34092/58 A GB34092/58 A GB 34092/58A GB 3409258 A GB3409258 A GB 3409258A GB 838928 A GB838928 A GB 838928A
- Authority
- GB
- United Kingdom
- Prior art keywords
- product
- steam
- oils
- stripping
- stripped
- 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
- 229930195733 hydrocarbon Natural products 0.000 title abstract 8
- 150000002430 hydrocarbons Chemical class 0.000 title abstract 7
- 239000000203 mixture Substances 0.000 title abstract 3
- 230000001050 lubricating effect Effects 0.000 title 1
- 239000000047 product Substances 0.000 abstract 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical class [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 4
- 239000005864 Sulphur Substances 0.000 abstract 4
- 239000000654 additive Substances 0.000 abstract 4
- 125000002947 alkylene group Chemical group 0.000 abstract 4
- 239000002480 mineral oil Substances 0.000 abstract 4
- 235000010446 mineral oil Nutrition 0.000 abstract 4
- 239000004215 Carbon black (E152) Substances 0.000 abstract 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 3
- 229920002367 Polyisobutene Polymers 0.000 abstract 3
- VKCLPVFDVVKEKU-UHFFFAOYSA-N S=[P] Chemical class S=[P] VKCLPVFDVVKEKU-UHFFFAOYSA-N 0.000 abstract 3
- 229920000642 polymer Polymers 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 2
- -1 alicyclic hydrocarbons Chemical class 0.000 abstract 2
- 239000006227 byproduct Substances 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 239000010687 lubricating oil Substances 0.000 abstract 2
- 239000010688 mineral lubricating oil Substances 0.000 abstract 2
- 239000003921 oil Substances 0.000 abstract 2
- 239000011574 phosphorus Substances 0.000 abstract 2
- 229910052698 phosphorus Inorganic materials 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 1
- 239000010694 animal lubricating oil Substances 0.000 abstract 1
- 230000003064 anti-oxidating effect Effects 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000010730 cutting oil Substances 0.000 abstract 1
- 239000003599 detergent Substances 0.000 abstract 1
- 238000007865 diluting Methods 0.000 abstract 1
- 239000002270 dispersing agent Substances 0.000 abstract 1
- 125000005677 ethinylene group Chemical class [*:2]C#C[*:1] 0.000 abstract 1
- 239000012208 gear oil Substances 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- 239000004094 surface-active agent Substances 0.000 abstract 1
- 239000010689 synthetic lubricating oil Substances 0.000 abstract 1
- 239000010723 turbine oil Substances 0.000 abstract 1
- 239000010693 vegetable lubricating oil Substances 0.000 abstract 1
- 235000013311 vegetables Nutrition 0.000 abstract 1
Classifications
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- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/04—Reaction products of phosphorus sulfur compounds with hydrocarbons
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- 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
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- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/40—Fatty vegetable or animal oils
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/40—Fatty vegetable or animal oils
- C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
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- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/12—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
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- C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2225/04—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of macromolecualr compounds not containing phosphorus in the monomers
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- C10M2225/041—Hydrocarbon polymers
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- C10N2040/175—Pantographs, i.e. printing devices
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- C10N2040/18—Electric or magnetic purposes in connection with recordings on magnetic tape or disc
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- Lubricants (AREA)
Abstract
Oxy-alkylated phosphosulphurized hydrocarbons, prepared by phosphosulphurizing a hydrocarbon, steam-stripping the product and then reacting it with a C2-C6 alkylene oxide (see Group IV (b)), may be used as extreme pressure or detergent additives in amounts from 0.001 to 30% by weight in mineral, animal, vegetable and synthetic lubricating oils, if desired in conjunction with the usual additives. The compounds may also be used as antioxidizing agents in cutting oils, rinsing oils, turbine oils, gear oils, transformer oils and mineral oil greases. Engine tests are described using a mineral lubricating oil containing 6% of a product obtained by phosphosulphurizing a polyisobutene (M.W. 1100), diluting with a mineral oil and steam-stripping the product and reacting it with 3-8% of ethylene oxide.ALSO:Oxy-alkylated phospho-sulphurized hydrocarbons are prepared by phospho-sulphurizing a hydrocarbon, steam-stripping the product thus obtained for a period of time sufficient to remove odours due to volatile by-product sulphur compounds and reacting the steam-stripped product with a C2-C6 alkylene oxide. The hydrocarbons, which may be paraffins, olefines, diolefines, olefine polymers, acetylenes, or aromatic, alkyl aromatic or alicyclic hydrocarbons including various petroleum fractions and cracked or condensed products therefrom, may be phospho-sulphurized with one or more phosphorus sulphides or a mixture of phosphorus and sulphur, suitably at 90-320 DEG C., generally using 1-10 mols. of hydrocarbon per mol. of phosphorus sulphide, in an inert atmosphere. The steam stripping is preferably effected at 100-200 DEG C. and continued until the acid number is at least 25 and the sulphur content is below 1.5% by weight. The steam-stripped product is preferably condensed with 1-10 mols. of alkylene oxide. The products may be used as lubricating oil additives (see Group III) or as surface-active agents, dispersing agents and vulcanizing accelerators. In an example, a polyisobutylene, M.W. about 1100, is reacted with P2S5, the product is diluted with mineral oil, steam-stripped at 120 DEG C. and then reacted with 3-8% ethylene oxide using BF3/ether or NaOH as catalyst.ALSO:Oxy-alkylated phospho-sulphurized olefine polymers are prepared by phosphosulphurizing the polymer, for example with a phosphorus sulphide or a mixture of phosphorus and sulphur, steam-stripping the product for a period of time sufficient to remove odours due to volatile by-product sulphur compound and reacting the stripped product with a C2-6 alkylene oxide, for example with 1-10 mols. of the oxide. The products are lubricating oil additives (see Group III). In an example, a polyisobutylene (M.W. 1100) is reacted with P2S5, the product diluted with mineral oil, then steam-stripped and finally reacted with 3-8% of ethylene oxide using BF3 or NaOH as catalyst.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1131205T | 1955-09-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB838928A true GB838928A (en) | 1960-06-22 |
Family
ID=9637745
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB21001/56A Expired GB792553A (en) | 1955-09-08 | 1956-07-06 | Improved additives suitable for lubricating oil compositions |
| GB34092/58A Expired GB838928A (en) | 1955-09-08 | 1958-10-24 | Oxyalkylated phosphosulphurised hydrocarbons and lubricating compositions therefrom |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB21001/56A Expired GB792553A (en) | 1955-09-08 | 1956-07-06 | Improved additives suitable for lubricating oil compositions |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR1131205A (en) |
| GB (2) | GB792553A (en) |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3087956A (en) * | 1960-09-30 | 1963-04-30 | Texaco Inc | Alkylene oxide reaction products |
| US3201438A (en) * | 1962-08-09 | 1965-08-17 | Texaco Inc | Method of producing a monoester of a hydrocarbyl thiophosphonic acid and a polyalkylene glycol |
| US3223495A (en) * | 1961-09-11 | 1965-12-14 | Exxon Research Engineering Co | Motor fuel composition |
| US3227532A (en) * | 1961-08-14 | 1966-01-04 | Exxon Research Engineering Co | Polymer-containing motor fuel composition |
| US3256189A (en) * | 1962-10-18 | 1966-06-14 | Texaco Inc | Hydrocarbyl ether reaction products |
| US3256191A (en) * | 1962-10-18 | 1966-06-14 | Texaco Inc | Alkenoate derivatives |
| US3256194A (en) * | 1962-10-18 | 1966-06-14 | Texaco Inc | Haloalkylene reaction products |
| US3256193A (en) * | 1962-10-18 | 1966-06-14 | Texaco Inc | Polyhydroxyoxaalkyl esters |
| US3256192A (en) * | 1962-10-18 | 1966-06-14 | Texaco Inc | Reaction products of glycidols |
| US3256190A (en) * | 1962-10-18 | 1966-06-14 | Texaco Inc | Thiophosphonoxyalkanes |
| US3257318A (en) * | 1960-09-15 | 1966-06-21 | Exxon Research Engineering Co | Lubricating compositions containing a synergistic mixture of additives |
| US3272744A (en) * | 1964-10-27 | 1966-09-13 | Texaco Inc | Lubricants containing alkylene oxide reaction products |
| US3281359A (en) * | 1964-08-27 | 1966-10-25 | Texaco Inc | Neopentyl polyol derivatives and lubricating compositions |
| US3285853A (en) * | 1963-10-09 | 1966-11-15 | Texaco Inc | Hydrocarbonthiophosphonates and lubricant compositions thereof |
| US3307928A (en) * | 1963-01-30 | 1967-03-07 | Exxon Research Engineering Co | Gasoline additives for enhancing engine cleanliness |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3001980A (en) * | 1956-08-04 | 1961-09-26 | Exxon Standard Sa | Lubricating oils |
| EP2132281B1 (en) | 2007-03-30 | 2019-06-12 | Dorf Ketal Chemicals (I) Private Limited | High temperature naphthenic acid corrosion inhibition using organophosphorous sulphur compounds and combinations thereof |
| CN101688118B (en) | 2007-04-04 | 2014-10-29 | 多尔夫凯塔尔化学制品（I）私人有限公司 | Naphthenic acid corrosion inhibition using new synergetic combination of phosphorus compounds |
| US9115319B2 (en) | 2007-09-14 | 2015-08-25 | Dorf Ketal Chemicals (I) Private Limited | Additive for naphthenic acid corrosion inhibition and method of using the same |
| KR101374609B1 (en) | 2008-08-26 | 2014-03-17 | 도르프 케탈 케미칼즈 (인디아) 프라이비트 리미티드 | A New Additive for Inhibiting Acid Corrosion and Method of Using the New Additive |
| AU2009286326B2 (en) | 2008-08-26 | 2013-05-02 | Dorf Ketal Chemicals (I) Private Limited | An effective novel polymeric additive for inhibiting napthenic acid corrosion and method of using the same |
-
1955
- 1955-09-08 FR FR1131205D patent/FR1131205A/en not_active Expired
-
1956
- 1956-07-06 GB GB21001/56A patent/GB792553A/en not_active Expired
-
1958
- 1958-10-24 GB GB34092/58A patent/GB838928A/en not_active Expired
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3257318A (en) * | 1960-09-15 | 1966-06-21 | Exxon Research Engineering Co | Lubricating compositions containing a synergistic mixture of additives |
| US3087956A (en) * | 1960-09-30 | 1963-04-30 | Texaco Inc | Alkylene oxide reaction products |
| US3227532A (en) * | 1961-08-14 | 1966-01-04 | Exxon Research Engineering Co | Polymer-containing motor fuel composition |
| US3223495A (en) * | 1961-09-11 | 1965-12-14 | Exxon Research Engineering Co | Motor fuel composition |
| US3201438A (en) * | 1962-08-09 | 1965-08-17 | Texaco Inc | Method of producing a monoester of a hydrocarbyl thiophosphonic acid and a polyalkylene glycol |
| US3256194A (en) * | 1962-10-18 | 1966-06-14 | Texaco Inc | Haloalkylene reaction products |
| US3256191A (en) * | 1962-10-18 | 1966-06-14 | Texaco Inc | Alkenoate derivatives |
| US3256193A (en) * | 1962-10-18 | 1966-06-14 | Texaco Inc | Polyhydroxyoxaalkyl esters |
| US3256192A (en) * | 1962-10-18 | 1966-06-14 | Texaco Inc | Reaction products of glycidols |
| US3256190A (en) * | 1962-10-18 | 1966-06-14 | Texaco Inc | Thiophosphonoxyalkanes |
| US3256189A (en) * | 1962-10-18 | 1966-06-14 | Texaco Inc | Hydrocarbyl ether reaction products |
| US3307928A (en) * | 1963-01-30 | 1967-03-07 | Exxon Research Engineering Co | Gasoline additives for enhancing engine cleanliness |
| US3285853A (en) * | 1963-10-09 | 1966-11-15 | Texaco Inc | Hydrocarbonthiophosphonates and lubricant compositions thereof |
| US3281359A (en) * | 1964-08-27 | 1966-10-25 | Texaco Inc | Neopentyl polyol derivatives and lubricating compositions |
| US3272744A (en) * | 1964-10-27 | 1966-09-13 | Texaco Inc | Lubricants containing alkylene oxide reaction products |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1131205A (en) | 1957-02-19 |
| GB792553A (en) | 1958-03-26 |
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