GB656471A - Improvements in or relating to the preparation of organic phosphates - Google Patents
Improvements in or relating to the preparation of organic phosphatesInfo
- Publication number
- GB656471A GB656471A GB2825/48A GB282548A GB656471A GB 656471 A GB656471 A GB 656471A GB 2825/48 A GB2825/48 A GB 2825/48A GB 282548 A GB282548 A GB 282548A GB 656471 A GB656471 A GB 656471A
- Authority
- GB
- United Kingdom
- Prior art keywords
- diphenyl
- alkyl
- phosphate
- dicresyl
- carbon atoms
- 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
- 229910019142 PO4 Inorganic materials 0.000 title abstract 7
- 235000021317 phosphate Nutrition 0.000 title abstract 7
- 150000003013 phosphoric acid derivatives Chemical class 0.000 title abstract 5
- 238000002360 preparation method Methods 0.000 title abstract 2
- -1 diaryl phosphate esters Chemical class 0.000 abstract 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 6
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 4
- 235000010290 biphenyl Nutrition 0.000 abstract 4
- 239000004305 biphenyl Substances 0.000 abstract 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 4
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 2
- 239000010452 phosphate Substances 0.000 abstract 2
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 abstract 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 1
- GANMEIBMNORMAX-UHFFFAOYSA-N 2-butoxyethyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OCCOCCCC)OC1=CC=CC=C1 GANMEIBMNORMAX-UHFFFAOYSA-N 0.000 abstract 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 abstract 1
- 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 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- CGSLYBDCEGBZCG-UHFFFAOYSA-N Octicizer Chemical compound C=1C=CC=CC=1OP(=O)(OCC(CC)CCCC)OC1=CC=CC=C1 CGSLYBDCEGBZCG-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000004848 alkoxyethyl group Chemical group 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 125000006267 biphenyl group Chemical group 0.000 abstract 1
- 235000019864 coconut oil Nutrition 0.000 abstract 1
- 239000003240 coconut oil Substances 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- 229930003836 cresol Natural products 0.000 abstract 1
- 125000000853 cresyl group Chemical group C1(=CC=C(C=C1)C)* 0.000 abstract 1
- 229940051043 cresylate Drugs 0.000 abstract 1
- UZJUEEROTUVKNS-UHFFFAOYSA-N decyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OCCCCCCCCCC)OC1=CC=CC=C1 UZJUEEROTUVKNS-UHFFFAOYSA-N 0.000 abstract 1
- DLZXXNAEQGRWPX-UHFFFAOYSA-N dodecyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OCCCCCCCCCCCC)OC1=CC=CC=C1 DLZXXNAEQGRWPX-UHFFFAOYSA-N 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 1
- 238000007689 inspection Methods 0.000 abstract 1
- 229940031826 phenolate Drugs 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 239000004014 plasticizer Substances 0.000 abstract 1
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 1
- 239000004800 polyvinyl chloride Substances 0.000 abstract 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 abstract 1
- 238000003756 stirring Methods 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Abstract
Monoalkyl and monoalkoxyethyl diaryl phosphate esters having the general formula <FORM:0656471/IV (b)/1> in which R is a phenyl or cresyl residue and R1 is an alkyl radical containing at least 6 but not more than 12 carbon atoms or an alkoxyethyl group in which the alkyl substituent has at least 4 but not more than 12 carbon atoms, are prepared by reacting one molecular proportion of phosphorus oxychloride with substantially one molecular proportion of an aliphatic alcohol having at least 6 but not more than 12 carbon atoms or an alkoxyethylene glycol in which the alkyl substituent has at least 4 but not more than 12 carbon atoms and reacting the alkyl or alkoxyethyl phosphoryl dichloride thus produced with an alkali metal salt of phenol or a cresol. The products are plasticizers for polyvinyl chloride and vinyl chloride copolymers, in connection with which reference is made to Specification 656,510, [Group IV (a)]. In examples: (1) 2-ethyl hexyl diphenyl phosphate is prepared by adding ethyl-hexanol to cooled phosphorus oxychloride with stirring, evolved hydrogen chloride being removed continuously by vacuum applied to the reaction vessel and the resulting ethyl-hexyl phosphoryl dichloride is added to an aqueous solution of sodium phenate; in like manner (2) 2-ethyl hexyl dicresyl phosphate, (3) lauryl diphenyl phosphate and (4) 2-methyl pentoxyethyl dicresyl phosphate are prepared. Other esters mentioned include n-hexyl diphenyl and dicresyl phosphates, n-octyl diphenyl and dicresyl phosphates, n-decyl diphenyl phosphate, n-butoxyethyl diphenyl phosphate, lauroxyethyl diphenyl and dicresyl phosphates and a mixture of alkyl diphenyl or dicresyl phosphates in which the alkyl residues are obtained from a mixture of aliphatic alcohols derived from coconut oil of which substantially 60 per cent of the alkyl radicals contain at least 8 and not more than 12 carbon atoms. The Specification as open to inspection under Sect. 91 describes a preparation of the above-mentioned esters which comprises reacting phosphorus oxychloride with the alcohol or alkoxy ethylene glycol and an alkali metal phenolate or cresylate. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US656471XA | 1947-01-04 | 1947-01-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB656471A true GB656471A (en) | 1951-08-22 |
Family
ID=22064159
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2825/48A Expired GB656471A (en) | 1947-01-04 | 1948-01-30 | Improvements in or relating to the preparation of organic phosphates |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB656471A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113999260A (en) * | 2021-07-19 | 2022-02-01 | 太仓市茜泾化工有限公司 | Alkyl diphenyl phosphate |
-
1948
- 1948-01-30 GB GB2825/48A patent/GB656471A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113999260A (en) * | 2021-07-19 | 2022-02-01 | 太仓市茜泾化工有限公司 | Alkyl diphenyl phosphate |
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