GB734783A - New neutral orthophosphate esters - Google Patents
New neutral orthophosphate estersInfo
- Publication number
- GB734783A GB734783A GB2040552A GB2040552A GB734783A GB 734783 A GB734783 A GB 734783A GB 2040552 A GB2040552 A GB 2040552A GB 2040552 A GB2040552 A GB 2040552A GB 734783 A GB734783 A GB 734783A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenyl
- substituted
- carbon atoms
- phosphoryl chloride
- group
- 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
- 230000007935 neutral effect Effects 0.000 title abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical class [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 title abstract 2
- BHIIGRBMZRSDRI-UHFFFAOYSA-N [chloro(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(Cl)OC1=CC=CC=C1 BHIIGRBMZRSDRI-UHFFFAOYSA-N 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 abstract 2
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- XKGDWZQXVZSXAO-ADYSOMBNSA-N Ricinoleic Acid methyl ester Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OC XKGDWZQXVZSXAO-ADYSOMBNSA-N 0.000 abstract 2
- XKGDWZQXVZSXAO-SFHVURJKSA-N Ricinolsaeure-methylester Natural products CCCCCC[C@H](O)CC=CCCCCCCCC(=O)OC XKGDWZQXVZSXAO-SFHVURJKSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000000853 cresyl group Chemical group C1(=CC=C(C=C1)C)* 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 239000004014 plasticizer Substances 0.000 abstract 2
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 2
- 239000004800 polyvinyl chloride Substances 0.000 abstract 2
- XKGDWZQXVZSXAO-UHFFFAOYSA-N ricinoleic acid methyl ester Natural products CCCCCCC(O)CC=CCCCCCCCC(=O)OC XKGDWZQXVZSXAO-UHFFFAOYSA-N 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 125000005023 xylyl group Chemical group 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 239000003377 acid catalyst Substances 0.000 abstract 1
- 125000005037 alkyl phenyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- -1 di-substituted phosphoryl chloride Chemical class 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 abstract 1
- FGHQZRHPPSYGDL-UHFFFAOYSA-N octan-2-yl diphenyl phosphate Chemical compound CCCCCCC(C)OP(=O)(OC1=CC=CC=C1)OC1=CC=CC=C1 FGHQZRHPPSYGDL-UHFFFAOYSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 150000003333 secondary alcohols Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 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
- 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)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Abstract
Plasticizers for polyvinyl chloride comprise compounds of the general formula <FORM:0734783/IV (a)/1> where R1 and R2, which may be alike or different each represents a chlorinated or unchlorinated phenyl, cresyl, xylyl or alkyl-phenyl radical, the last-mentioned having at least one branched side chain and containing a total of from 4 to 9 carbon atoms in the side-chain or chains, R3 and R4 each represent alkyl radicals, one of which may be substituted by a carbalkoxy or alkoxy group, R3 and R4 together (including any substituent) containing from 3 to 20 carbon atoms. The preparation of such compounds, and in particular those in which R1 and R2 represent the phenyl radical and the group <FORM:0734783/IV (a)/2> is derived from octon-2-ol, 1-n-butoxy-propane-2-ol, methyl isobutyl carbinol, and methyl ricinoleate are described (see Group IV (b)). Specifications 734,764, 734,765 and 734,768 [Group IV (b)], are referred to.ALSO:The invention comprises neutral orthophosphate esters of the general formula <FORM:0734783/IV (b)/1> where R1 and R2, which may be alike or different, each represents a chlorinated or unchlorinated phenyl, cresyl, xylyl or alkylphenyl radical, the last-mentioned having at least one branched side-chain and containing a total of from 4 to 9 carbon atoms in the sidechain or chains, R3 and R4 represent alkyl radicals, one of which may be substituted by a carbalkoxy or alkoxy group, R3 and R4 together (including any substituent) containing from 3 to 20 carbon atoms. Such esters are obtained by adding a di-substituted phosphoryl chloride of the formula <FORM:0734783/IV (b)/2> progressively in proportion as it is used up in the reaction to a refluxing mixture of a hydrocarbon solvent and one equivalent of a substituted or unsubstituted secondary alcohol of the general formula R3.CH(OH).R4 or to one equivalent of the alcohol heated alone in vacuo to a temperature not exceeding 100 DEG C., in the presence of a catalytic quantity of a tertiary amine or its hydrogen chloride salt. In examples there are reacted together in the above manner in the presence of pyridine (1) octan-2-ol and diphenyl phosphoryl chloride to give di-phenyl 1-methylheptyl phosphate. In a comparison experiment the amine is omitted; (2) 1-n-butoxy-propane-2-ol (obtained by condensing normal butanol with propylene oxide in the presence of acid catalysts) and diphenyl phosphoryl chloride; (3) methyl isobutyl carbinol and diphenyl phosphoryl chloride; (4) methyl ricinoleate and diphenyl phosphoryl chloride. The products can be used as plasticizers for polyvinyl chloride. Specifications 734,764, 734,765 and 734,768 are referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2040552A GB734783A (en) | 1952-08-13 | 1952-08-13 | New neutral orthophosphate esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2040552A GB734783A (en) | 1952-08-13 | 1952-08-13 | New neutral orthophosphate esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB734783A true GB734783A (en) | 1955-08-10 |
Family
ID=10145428
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2040552A Expired GB734783A (en) | 1952-08-13 | 1952-08-13 | New neutral orthophosphate esters |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB734783A (en) |
-
1952
- 1952-08-13 GB GB2040552A patent/GB734783A/en not_active Expired
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