GB890642A - Improvements in or relating to aryl phosphates - Google Patents
Improvements in or relating to aryl phosphatesInfo
- Publication number
- GB890642A GB890642A GB852957A GB852957A GB890642A GB 890642 A GB890642 A GB 890642A GB 852957 A GB852957 A GB 852957A GB 852957 A GB852957 A GB 852957A GB 890642 A GB890642 A GB 890642A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phosphates
- mixture
- free
- ortho
- ethylphenol
- 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 20
- 235000021317 phosphate Nutrition 0.000 title abstract 20
- -1 aryl phosphates Chemical class 0.000 title abstract 5
- 150000003013 phosphoric acid derivatives Chemical class 0.000 abstract 16
- 239000000203 mixture Substances 0.000 abstract 14
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 abstract 8
- HMNKTRSOROOSPP-UHFFFAOYSA-N 3-Ethylphenol Chemical compound CCC1=CC=CC(O)=C1 HMNKTRSOROOSPP-UHFFFAOYSA-N 0.000 abstract 6
- QDQMEHXIUFCIGR-UHFFFAOYSA-N 4-ethyl-2-methylphenol Chemical compound CCC1=CC=C(O)C(C)=C1 QDQMEHXIUFCIGR-UHFFFAOYSA-N 0.000 abstract 6
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 abstract 6
- 150000003254 radicals Chemical class 0.000 abstract 5
- IXQGCWUGDFDQMF-UHFFFAOYSA-N 2-Ethylphenol Chemical compound CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 abstract 4
- YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 abstract 4
- 231100000252 nontoxic Toxicity 0.000 abstract 4
- 230000003000 nontoxic effect Effects 0.000 abstract 4
- 238000004519 manufacturing process Methods 0.000 abstract 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 3
- 239000010452 phosphate Substances 0.000 abstract 3
- 239000004014 plasticizer Substances 0.000 abstract 3
- 229920003002 synthetic resin Polymers 0.000 abstract 3
- 239000000057 synthetic resin Substances 0.000 abstract 3
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 abstract 2
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 abstract 2
- 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
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 abstract 2
- AYGDIAGADYTJRY-UHFFFAOYSA-N 5-ethyl-2-methylphenol Chemical compound CCC1=CC=C(C)C(O)=C1 AYGDIAGADYTJRY-UHFFFAOYSA-N 0.000 abstract 2
- 238000009835 boiling Methods 0.000 abstract 2
- 229930003836 cresol Natural products 0.000 abstract 2
- 125000000486 o-cresyl group Chemical group [H]C1=C([H])C(O*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 abstract 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 abstract 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 2
- 150000002989 phenols Chemical class 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 2
- 239000004800 polyvinyl chloride Substances 0.000 abstract 2
- 239000011289 tar acid Substances 0.000 abstract 2
- KOWVWXQNQNCRRS-UHFFFAOYSA-N tris(2,4-dimethylphenyl) phosphate Chemical compound CC1=CC(C)=CC=C1OP(=O)(OC=1C(=CC(C)=CC=1)C)OC1=CC=C(C)C=C1C KOWVWXQNQNCRRS-UHFFFAOYSA-N 0.000 abstract 2
- 150000003739 xylenols Chemical class 0.000 abstract 2
- BPRYUXCVCCNUFE-UHFFFAOYSA-N 2,4,6-trimethylphenol Chemical compound CC1=CC(C)=C(O)C(C)=C1 BPRYUXCVCCNUFE-UHFFFAOYSA-N 0.000 abstract 1
- LCHYEKKJCUJAKN-UHFFFAOYSA-N 2-propylphenol Chemical compound CCCC1=CC=CC=C1O LCHYEKKJCUJAKN-UHFFFAOYSA-N 0.000 abstract 1
- OSDLLIBGSJNGJE-UHFFFAOYSA-N 4-chloro-3,5-dimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1Cl OSDLLIBGSJNGJE-UHFFFAOYSA-N 0.000 abstract 1
- ZVEWFTICTSQBDM-UHFFFAOYSA-N 4-methylphenol Chemical compound [CH2]C1=CC=C(O)C=C1 ZVEWFTICTSQBDM-UHFFFAOYSA-N 0.000 abstract 1
- 241000287828 Gallus gallus Species 0.000 abstract 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 235000013330 chicken meat Nutrition 0.000 abstract 1
- 239000011280 coal tar Substances 0.000 abstract 1
- 235000013305 food Nutrition 0.000 abstract 1
- 238000005194 fractionation Methods 0.000 abstract 1
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 abstract 1
- 229940100630 metacresol Drugs 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 231100000820 toxicity test Toxicity 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)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The invention comprises a synthetic resin, e.g. polyvinyl chloride, containing as a plasticizer therefore a mixture of trialkaryl phosphates free from phosphates containing one or more orthomonoalkylphenyl radicals (see Group IV(b) ). The phosphate mixture is non-toxic and is preferably a mixture of tritolyl phosphates free from phosphates containing one or more o-cresyl and o-ethylphenyl radicals or a mixture of trixylenyl phosphates free from phosphates containing one or more o-cresyl, o-ethylphenyl and o-propylphenyl radicals. The plasticized synthetic resin may be used in the manufacture of food wrappings and articles which come in contact with the human body, e.g. pants for babies. Specification 890,643 is referred to.ALSO:The invention comprises a mixture of trialkaryl phosphates suitable for use as a nontoxic plasticiser which mixture is free from phosphates containing one or more ortho-monoalkylphenyl radicals, and particularly a mixture of tritolyl phosphates free from phosphates containing one or more ortho-cresyl and orthoethylphenyl radicals and a mixture of trixylenyl phosphates free from phosphates containing one or more ortho-cresyl, ortho-ethylphenyl and ortho-propylphenyl radicals. The content of tri-2 : 4/2 : 5-dimethylphenyl phosphates and of phosphates containing one or two 2 : 4/2 : 5-dimethylphenyl radicals in the mixture of trixylenyl phosphates should preferably be below 10% by weight but the mixture may contain phosphates of meta- and para-ethylphenol and of 2-methyl-4-ethyl-phenol. The phosphate mixture may be obtained by reacting a phenolic fraction free from o-monoalkyl phenols, e.g. a cresol fraction free from o-cresol and o-ethyl-phenol and/or a xylenol free from ortho-cresol, ortho-ethyl phenol and ortho-propyl phenol, with a phosphating agent, preferably phosphorus oxychloride. Examples are given for the production of (1) a non-toxic tritolyl phosphate mixture from a tar acid cresol fraction comprising meta-cresol (48%), para-cresol (35%) and 2 : 4/2 : 5-dimethylphenol (17%), and (2) a trixylenyl phosphate mixture from a tar acid fraction having a boiling range of 220 DEG C.-232.5 DEG C. and comprising 3 : 5-xylenyl (31%), meta/para-ethylphenol (16%), 3,4-xylenol (18%), 2-methyl-4-ethylphenol and 2-methyl-5-ethylphenol (30%) and 5% of other phenols, the fraction being free from o-cresol, o-ethylphenol and o-n-propylphenol. The phenolic fractions are obtained by careful fractionation of a coal tar fraction by the procedure described in Specification 890,643. Toxicity tests of the phosphate products on chickens aged between 3 and 12 months show the products to be completely non-toxic. The products are useful as plasticisers for synthetic resins, e.g. polyvinyl chloride (see Group IV (a)). The first Provisional Specification also discloses the production of a trixylenyl phosphate from a xylenol fraction having an Engler boiling range of 217 DEG C.-225 DEG C. and having the following composition by volume: 2,4/2,5 -dimethyl-phenol (5%) meta- and para-ethylphenol (40%), 2,3-dimethylphenol (10%) mesitol (5%), 3,5-dimethylphenol (20%), 2-methyl-4-ethylphenol (10%) and 3,4-dimethylphenol (10%).
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB852957A GB890642A (en) | 1957-03-14 | 1957-03-14 | Improvements in or relating to aryl phosphates |
| GB3493461A GB890643A (en) | 1957-03-14 | 1957-03-14 | Tar acid fractions |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB852957A GB890642A (en) | 1957-03-14 | 1957-03-14 | Improvements in or relating to aryl phosphates |
| GB2268957 | 1957-07-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB890642A true GB890642A (en) | 1962-03-07 |
Family
ID=26242231
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB852957A Expired GB890642A (en) | 1957-03-14 | 1957-03-14 | Improvements in or relating to aryl phosphates |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB890642A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4069189A (en) | 1966-06-18 | 1978-01-17 | Ciba-Geigy Ag | Chemical process and products |
| USRE29540E (en) | 1966-06-18 | 1978-02-14 | Ciba-Geigy Ag | Phosphorylated alkylphenol/phenol ester mixtures |
| US4139487A (en) | 1965-12-01 | 1979-02-13 | Albright & Wilson Limited | Mixed tri-aryl (phenyl and alkylphenyl) phosphate esters |
-
1957
- 1957-03-14 GB GB852957A patent/GB890642A/en not_active Expired
Cited By (3)
| 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 |
| US4069189A (en) | 1966-06-18 | 1978-01-17 | Ciba-Geigy Ag | Chemical process and products |
| USRE29540E (en) | 1966-06-18 | 1978-02-14 | Ciba-Geigy Ag | Phosphorylated alkylphenol/phenol ester mixtures |
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