GB1098637A - Preparation of phosphorus esters - Google Patents
Preparation of phosphorus estersInfo
- Publication number
- GB1098637A GB1098637A GB3475065A GB3475065A GB1098637A GB 1098637 A GB1098637 A GB 1098637A GB 3475065 A GB3475065 A GB 3475065A GB 3475065 A GB3475065 A GB 3475065A GB 1098637 A GB1098637 A GB 1098637A
- Authority
- GB
- United Kingdom
- Prior art keywords
- reaction
- reaction mixture
- prepared
- halo
- alcohols
- 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
- 150000003017 phosphorus Chemical class 0.000 title 1
- 239000003054 catalyst Substances 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 3
- 239000011541 reaction mixture Substances 0.000 abstract 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- 150000001298 alcohols Chemical class 0.000 abstract 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 abstract 2
- 229910052698 phosphorus Inorganic materials 0.000 abstract 2
- RZUXIYDMQGCCDD-UHFFFAOYSA-N 2,3-dibromobutan-1-ol Chemical compound CC(Br)C(Br)CO RZUXIYDMQGCCDD-UHFFFAOYSA-N 0.000 abstract 1
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 abstract 1
- DBTWOTKWIVISQR-UHFFFAOYSA-N 2-bromopropan-1-ol Chemical compound CC(Br)CO DBTWOTKWIVISQR-UHFFFAOYSA-N 0.000 abstract 1
- XYFMKXAUKVXBTM-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl.OCCCl XYFMKXAUKVXBTM-UHFFFAOYSA-N 0.000 abstract 1
- 229910015900 BF3 Inorganic materials 0.000 abstract 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- 229910019142 PO4 Inorganic materials 0.000 abstract 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- 101100313649 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) POT1 gene Proteins 0.000 abstract 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 abstract 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 abstract 1
- 101100161758 Yarrowia lipolytica (strain CLIB 122 / E 150) POX3 gene Proteins 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- 230000007812 deficiency Effects 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 150000003944 halohydrins Chemical class 0.000 abstract 1
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract 1
- 239000012433 hydrogen halide Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 239000003701 inert diluent Substances 0.000 abstract 1
- 239000011261 inert gas Substances 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 239000010452 phosphate Substances 0.000 abstract 1
- 150000008301 phosphite esters Chemical class 0.000 abstract 1
- 125000004437 phosphorous atom Chemical group 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- 150000003138 primary alcohols Chemical class 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 239000011135 tin Substances 0.000 abstract 1
- 229910052718 tin Inorganic materials 0.000 abstract 1
- 239000010936 titanium Substances 0.000 abstract 1
- 229910052719 titanium Inorganic materials 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
- 239000011701 zinc 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
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- 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
- C07F9/141—Esters of phosphorous acids
- C07F9/1411—Esters of phosphorous acids with hydroxyalkyl compounds with further substituents on alkyl
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
b -Halo-alkyl phosphate or phosphite esters are prepared by reacting a phosphorus trihalide of the formula POX3 or PX3 respectively, where X represents a halogen atom with a b -haloalcohol in the presence of a Friedel-Crafts catalyst. The preferred alcohols are primary alcohols containing at least one halogen atom in the b -position to the hydroxy group. The catalysts include the halides of aluminium, tin, titanium, iron, zinc and magnesium, and boron trifluoride, and are preferably freshly prepared. They may be added as such to the reaction mixture or prepared in situ by adding the appropriate metal to the reaction mixture. The reaction may be effected by mixing the reactants in the presence of the catalyst, or an inert solvent or diluent may be used. The reaction may be carried out at room temperature, or at temperatures of from -10 DEG to 100 DEG C. It may be carried out under reflux or under reduced pressure, or an inert gas may be passed through the reaction mixture to remove hydrogen halide formed in the reaction. Esters containing residual halogen atoms on the phosphorus atom are produced by using a stoichiometric deficiency of the halo-alcohol. Specified alcohols are 2,3-dibromo-, 2,3-dichloro-, 2,3-di-iodo-, 2,3-difluoro-, and 2-bromopropanol, 2-chloro-, and 2-bromoethanol, and 2,3-dibromobutanol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3475065A GB1098637A (en) | 1965-08-13 | 1965-08-13 | Preparation of phosphorus esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3475065A GB1098637A (en) | 1965-08-13 | 1965-08-13 | Preparation of phosphorus esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1098637A true GB1098637A (en) | 1968-01-10 |
Family
ID=10369515
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3475065A Expired GB1098637A (en) | 1965-08-13 | 1965-08-13 | Preparation of phosphorus esters |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1098637A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4714771A (en) * | 1985-11-27 | 1987-12-22 | The Dow Chemical Company | Process for preparing halogenated trialkyl phosphate esters |
-
1965
- 1965-08-13 GB GB3475065A patent/GB1098637A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4714771A (en) * | 1985-11-27 | 1987-12-22 | The Dow Chemical Company | Process for preparing halogenated trialkyl phosphate esters |
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