GB837679A - Mixtures of triaryl phosphates - Google Patents
Mixtures of triaryl phosphatesInfo
- Publication number
- GB837679A GB837679A GB33999/56A GB3399956A GB837679A GB 837679 A GB837679 A GB 837679A GB 33999/56 A GB33999/56 A GB 33999/56A GB 3399956 A GB3399956 A GB 3399956A GB 837679 A GB837679 A GB 837679A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenol
- mixture
- xylenols
- triaryl phosphate
- cresol
- 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
- 239000000203 mixture Substances 0.000 title abstract 16
- 229910019142 PO4 Inorganic materials 0.000 title abstract 8
- 235000021317 phosphate Nutrition 0.000 title 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 title 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 12
- -1 alkyl monohydric phenols Chemical class 0.000 abstract 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 7
- 239000010452 phosphate Substances 0.000 abstract 7
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 abstract 6
- 150000003739 xylenols Chemical class 0.000 abstract 6
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 4
- OCKYMBMCPOAFLL-UHFFFAOYSA-N 2-ethyl-3-methylphenol Chemical compound CCC1=C(C)C=CC=C1O OCKYMBMCPOAFLL-UHFFFAOYSA-N 0.000 abstract 3
- LCHYEKKJCUJAKN-UHFFFAOYSA-N 2-propylphenol Chemical compound CCCC1=CC=CC=C1O LCHYEKKJCUJAKN-UHFFFAOYSA-N 0.000 abstract 3
- 150000001896 cresols Chemical class 0.000 abstract 3
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 abstract 3
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 abstract 3
- 150000003016 phosphoric acids Chemical class 0.000 abstract 3
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 239000012530 fluid Substances 0.000 abstract 2
- 239000000314 lubricant Substances 0.000 abstract 2
- 239000004800 polyvinyl chloride Substances 0.000 abstract 2
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 2
- 239000012815 thermoplastic material Substances 0.000 abstract 2
- 239000001856 Ethyl cellulose Substances 0.000 abstract 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 abstract 1
- 229920001074 Tenite Polymers 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 229920002678 cellulose Polymers 0.000 abstract 1
- 229920003086 cellulose ether Polymers 0.000 abstract 1
- 229920001249 ethyl cellulose Polymers 0.000 abstract 1
- 235000019325 ethyl cellulose Nutrition 0.000 abstract 1
- ONUFRYFLRFLSOM-UHFFFAOYSA-N lead;octadecanoic acid Chemical compound [Pb].CCCCCCCCCCCCCCCCCC(O)=O ONUFRYFLRFLSOM-UHFFFAOYSA-N 0.000 abstract 1
- 229910001629 magnesium chloride Inorganic materials 0.000 abstract 1
- 229910001507 metal halide Inorganic materials 0.000 abstract 1
- 150000005309 metal halides Chemical class 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- 239000004014 plasticizer Substances 0.000 abstract 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
- C08K5/523—Esters of phosphoric acids, e.g. of H3PO4 with hydroxyaryl compounds
-
- 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
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl 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
- C10M2223/041—Triaryl phosphates
-
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Lubricants (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Hydraulic systems contain as the operative fluid a triaryl phosphate mixture obtainable by reacting an ester-forming derivative of phosphoric acid with a mixture of phenol, cresols, xylenols, and higher alkyl monohydric phenols in which the alkyl group or groups of each phenol contain a total of 3 to 6 carbon atoms in such proportions as to give a product having a viscosity of 140 to 160 S.U.S. at 100 DEG F. (see Group IV (b)). The triaryl phosphate mixture is also useful as a lubricant. Suitable phenol mixtures are those comprising by weight 6 to 10% phenol, 35 to 45% of meta- and para-cresol, 10 to 14% of ortho cresol, 25 to 35% of xylenols and 8 to 12% of the higher alkyl phenols, e.g. propyl phenol, methyl ethyl phenol and butyl phenol.ALSO:A triaryl phosphate mixture is obtained by reacting an ester-forming derivative of phosphoric acid with a mixture of phenol, cresols, xylenols and higher alkyl monohydric phenols in which the alkyl group or groups of each phenol contain a total of 3 to 6 carbon atoms in such proportions as to give a product having a viscosity of 140 to 160 S.U.S. at 100 DEG F. The invention also includes triaryl phosphate mixtures obtainable by such process. Specified ester-forming phosphoric acid drivatives are phosphorus-oxychloride, -pentoxide and -pentachloride. It is preferred to use mixtures containing by weight 6 to 10% (preferably 8%) of phenol, 35 to 45% (preferably 40%) of meta-and para-cresol, 10 to 14% (preferably 12%) of ortho-cresol, 25 to 35% (preferably 30%) of xylenols and 8 to 12% (preferably 10%) of the higher alkyl phenols, e.g. propyl phenol, methyl ethyl phenol, and butyl phenol and an excess of 5 to 8% by weight of phenols is generally used. A metal halide catalyst, e.g. aluminium chloride or magnesium chloride may be present. The triaryl phosphate mixtures are useful as lubricants, as working fluids in hydraulic systems (see Group III) and as plasticizers for various thermoplastic materials (see Group IV (a)).ALSO:A thermoplastic material, e.g. polyvinyl chloride or a cellulosic thermoplastic such as a cellulose ester of a saturated aliphatic monocarboxylic acid containing 2 to 4 carbon atoms or a cellulose ether, e.g. ethyl cellulose, is plasticized with a triaryl phosphate mixture obtainable by reacting an ester-forming derivative of phosphoric acid with a mixture of phenol, cresols, xylenols and higher alkyl monohydric phenols in which the alkyl group or groups of each phenol contain a total of 3 to 6 carbon atoms in such proportions as to give a product having a viscosity of 140 to 160 SUS at 100 DEG F. (see Group IV (b)). Suitable phenol mixtures are those comprising by weight 6 to 10% (preferably 8%) of phenol, 35 to 45% (preferably 40%) of meta- and para-cresol, 10 to 14% (preferably 12%) of ortho cresol, 25 to 35% (preferably 30%) of xylenols and 8 to 12% (preferably 10%) of the higher alkyl phenols, e.g. propyl phenol, methyl ethyl phenol, and butyl phenol. In an example, 40 parts of a triaryl phosphate mixture obtained by reacting a phenol mixture of the preferred composition given above with phosphorus oxychloride is blended with 60 parts of polyvinyl chloride and 1.0 part of lead stearate is added, all parts being by weight.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US837679XA | 1955-11-08 | 1955-11-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB837679A true GB837679A (en) | 1960-06-15 |
Family
ID=22180569
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB33999/56A Expired GB837679A (en) | 1955-11-08 | 1956-11-07 | Mixtures of triaryl phosphates |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB837679A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4139487A (en) | 1965-12-01 | 1979-02-13 | Albright & Wilson Limited | Mixed tri-aryl (phenyl and alkylphenyl) phosphate esters |
-
1956
- 1956-11-07 GB GB33999/56A patent/GB837679A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4139487A (en) | 1965-12-01 | 1979-02-13 | Albright & Wilson Limited | Mixed tri-aryl (phenyl and alkylphenyl) phosphate esters |
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