GB1112976A - Process for the production of organo-phosphorus compounds - Google Patents
Process for the production of organo-phosphorus compoundsInfo
- Publication number
- GB1112976A GB1112976A GB25556/65A GB2555665A GB1112976A GB 1112976 A GB1112976 A GB 1112976A GB 25556/65 A GB25556/65 A GB 25556/65A GB 2555665 A GB2555665 A GB 2555665A GB 1112976 A GB1112976 A GB 1112976A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phosphorus
- compound containing
- hydrocarbon compound
- hydroxyl group
- compounds
- 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
- 150000002903 organophosphorus compounds Chemical class 0.000 title abstract 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 8
- 150000002430 hydrocarbons Chemical class 0.000 abstract 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 6
- 229910052698 phosphorus Inorganic materials 0.000 abstract 6
- 239000011574 phosphorus Substances 0.000 abstract 6
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 abstract 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 5
- BDFAOUQQXJIZDG-UHFFFAOYSA-N 2-methylpropane-1-thiol Chemical compound CC(C)CS BDFAOUQQXJIZDG-UHFFFAOYSA-N 0.000 abstract 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- 239000001301 oxygen Substances 0.000 abstract 3
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 abstract 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 2
- 239000000654 additive Substances 0.000 abstract 2
- 230000001476 alcoholic effect Effects 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 229930003836 cresol Natural products 0.000 abstract 2
- VTXVGVNLYGSIAR-UHFFFAOYSA-N decane-1-thiol Chemical compound CCCCCCCCCCS VTXVGVNLYGSIAR-UHFFFAOYSA-N 0.000 abstract 2
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- TXGJTWACJNYNOJ-UHFFFAOYSA-N hexane-2,4-diol Chemical compound CCC(O)CC(C)O TXGJTWACJNYNOJ-UHFFFAOYSA-N 0.000 abstract 2
- 239000010687 lubricating oil Substances 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- 229920001223 polyethylene glycol Polymers 0.000 abstract 2
- 235000000346 sugar Nutrition 0.000 abstract 2
- 150000008163 sugars Chemical class 0.000 abstract 2
- WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 abstract 2
- 125000003396 thiol group Chemical group [H]S* 0.000 abstract 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-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
- 239000012431 aqueous reaction media Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000000446 fuel Substances 0.000 abstract 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 abstract 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000003973 paint Substances 0.000 abstract 1
- 239000004033 plastic Substances 0.000 abstract 1
- 229920003023 plastic Polymers 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
-
- 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
- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
- C10M159/123—Reaction products obtained by phosphorus or phosphorus-containing compounds, e.g. P x S x with organic compounds
-
- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
-
- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/042—Metal salts thereof
-
- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/047—Thioderivatives not containing metallic elements
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/015—Dispersions of solid lubricants
- C10N2050/02—Dispersions of solid lubricants dissolved or suspended in a carrier which subsequently evaporates to leave a lubricant coating
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Lubricants (AREA)
Abstract
Additives for lubricating oils comprise compounds prepared by reacting white phosphorus oxygen, and a hydrocarbon compound containing at least one phenolic hydroxyl group, or a hydrocarbon compound containing more than one alcoholic hydroxyl group, or a hydrocarbon compound containing at least one thiol group, in a non-aqueous reaction medium at a temperature of up to about 60 DEG C. until substantially all the elementary phosphorus has been converted into esters of oxyacids of phosphorus in which the average overall oxidation state is substantially 4. Specified substituted hydrocarbon compounds are phenol, cresol, hydroquinone, ethylene glycol, polyethylene glycols, glycerol, sugars, chlorinated propylene glycol, 1,4-butane diol, 1-methyl-1,3-pentane diol, decane-thiol, dodecanethiol, t-butylmercaptan, isobutylmercaptan and thiophenol.ALSO:Organo-phosphorus compounds are prepared by reacting white phosphorus, oxygen (preferably provided as a stream of air), and a hydrocarbon compound containing at least one phenolic hydroxyl group, or a hydrocarbon compound containing more than one alcoholic hydroxyl group, or a hydrocarbon compound containing a thiol group, in a non-aqueous reaction system at a temperature of up to about 60 DEG C., until substantially all the elementary phosphorus present has been converted into esters of oxyacids of phosphorus in which the average overall oxidation state of the phosphorus is substantially 4. The reaction is preferably effected in the presence of an inert organic solvent, e.g. ethyl acetate or butyl acetate, in which the reactants and products are both soluble, and in which the phosphorus and oxygen are at least slightly soluble. Suitable starting materials are phenol, cresol, hydroquinone, ethylene, glycol, polyethylene glycols, glycerol, sugars, chlorinated propylene glycol, 1,4-butane diol, 1-methyl-1,3-pentane diol, decanethiol, dodecanethiol, t-butylmercaptan, isobutylmercaptan and thiophenol. The products may be used as additives for motor fuels, lubricating oils, plastics and paint, as flame-proofing agents, and as intermediates for the production of organophosphorus compounds.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB25556/65A GB1112976A (en) | 1965-06-16 | 1965-06-16 | Process for the production of organo-phosphorus compounds |
| IL25897A IL25897A (en) | 1965-06-16 | 1966-06-01 | Production of organo phosphorus compounds |
| DE19661568292 DE1568292A1 (en) | 1965-06-16 | 1966-06-08 | Process for the preparation of organophosphorus compounds |
| FR65586A FR1495493A (en) | 1965-06-16 | 1966-06-15 | Process for the production of organo-phosphorus products and new products thus obtained |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2555965 | 1965-06-16 | ||
| GB25556/65A GB1112976A (en) | 1965-06-16 | 1965-06-16 | Process for the production of organo-phosphorus compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1112976A true GB1112976A (en) | 1968-05-08 |
Family
ID=26257749
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB25556/65A Expired GB1112976A (en) | 1965-06-16 | 1965-06-16 | Process for the production of organo-phosphorus compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1112976A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1008552A1 (en) * | 1998-12-10 | 2000-06-14 | Monsanto Company | Process for producing phosphorus acid |
| WO2001051416A1 (en) * | 2000-01-14 | 2001-07-19 | Basf Aktiengesellschaft | Synthesis of phosphorous(iii) compounds starting from white phosphorous |
-
1965
- 1965-06-16 GB GB25556/65A patent/GB1112976A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1008552A1 (en) * | 1998-12-10 | 2000-06-14 | Monsanto Company | Process for producing phosphorus acid |
| US6194604B1 (en) | 1998-12-10 | 2001-02-27 | Monsanto Company | Process for producing phosphorous acid |
| WO2001051416A1 (en) * | 2000-01-14 | 2001-07-19 | Basf Aktiengesellschaft | Synthesis of phosphorous(iii) compounds starting from white phosphorous |
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