GB601210A - A process for the preparation of esters of fluorophosphonic acids and chlorophosphonic esters - Google Patents
A process for the preparation of esters of fluorophosphonic acids and chlorophosphonic estersInfo
- Publication number
- GB601210A GB601210A GB1516043A GB1516043A GB601210A GB 601210 A GB601210 A GB 601210A GB 1516043 A GB1516043 A GB 1516043A GB 1516043 A GB1516043 A GB 1516043A GB 601210 A GB601210 A GB 601210A
- Authority
- GB
- United Kingdom
- Prior art keywords
- butyl
- hydrogen phosphite
- sec
- isopropyl
- carbon tetrachloride
- 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
- 150000002148 esters Chemical class 0.000 title abstract 3
- DWYMPOCYEZONEA-UHFFFAOYSA-N fluorophosphoric acid Chemical class OP(O)(F)=O DWYMPOCYEZONEA-UHFFFAOYSA-N 0.000 title abstract 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 6
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 abstract 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- GBHRVZIGDIUCJB-UHFFFAOYSA-N hydrogenphosphite Chemical compound OP([O-])[O-] GBHRVZIGDIUCJB-UHFFFAOYSA-N 0.000 abstract 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- ITVPBBDAZKBMRP-UHFFFAOYSA-N chloro-dioxido-oxo-$l^{5}-phosphane;hydron Chemical compound OP(O)(Cl)=O ITVPBBDAZKBMRP-UHFFFAOYSA-N 0.000 abstract 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 abstract 2
- 229910001506 inorganic fluoride Inorganic materials 0.000 abstract 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- WREDNUONGSTUAU-UHFFFAOYSA-N 1-[chloro(3-methylbutoxy)phosphoryl]oxy-3-methylbutane Chemical compound CC(C)CCOP(Cl)(=O)OCCC(C)C WREDNUONGSTUAU-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- UURIHCKMZRIKSJ-UHFFFAOYSA-N dibutan-2-yl hydrogen phosphite Chemical compound CCC(C)OP(O)OC(C)CC UURIHCKMZRIKSJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- MUCZHBLJLSDCSD-UHFFFAOYSA-N diisopropyl fluorophosphate Chemical compound CC(C)OP(F)(=O)OC(C)C MUCZHBLJLSDCSD-UHFFFAOYSA-N 0.000 abstract 1
- NFORZJQPTUSMRL-UHFFFAOYSA-N dipropan-2-yl hydrogen phosphite Chemical compound CC(C)OP(O)OC(C)C NFORZJQPTUSMRL-UHFFFAOYSA-N 0.000 abstract 1
- OXZZGSHHVGIAGR-UHFFFAOYSA-N ethyl 2-[(1-ethoxy-1-oxopropan-2-yl)oxy-hydroxyphosphanyl]oxypropanoate Chemical compound P(OC(C)C(=O)OCC)(OC(C)C(=O)OCC)O OXZZGSHHVGIAGR-UHFFFAOYSA-N 0.000 abstract 1
- 229940116333 ethyl lactate Drugs 0.000 abstract 1
- 235000013024 sodium fluoride Nutrition 0.000 abstract 1
- 239000011775 sodium fluoride Substances 0.000 abstract 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical class OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 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
- C07F9/14—Esters of phosphoric acids containing P(=O)-halide groups
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
Fluorophosphonic acid esters are obtained by reacting a chlorophosphonic ester of the formula <FORM:0601210/IV(b)/1> where R is an aliphatic radical, with an inorganic fluoride. The chlorosulphonic acid esters are obtained by treating an organic hydrogen phosphite of the formula <FORM:0601210/IV(b)/2> (obtained by adding phosphorous trichloride to an alcohol preferably using a solvent, e.g. carbon tetrachloride) with chlorine. It is not necessary to isolate either the hydrogen phosphite or the chlorophosphonic acid so that the whole of the reactions may be carried out in a single vessel. In examples (1) to (4) chlorine is passed into the hydrogen phosphite to produce di-isopropyl, diethyl, di-sec.-butyl and di-isoamyl chlorophosphonate; (5) to (11) the chlorophosphonate is gently heated with an inorganic fluoride to produce di-isopropyl, di-ethyl di-sec.-butyl, di-isoamyl, di-(1 : 3-dimethyl-n-butyl), di-(1-carbethoxyethyl) and di-(1 : 3-dichloroisopropyl) fluorophosphonate; (12) phosphorus trichloride is added to isopropyl alcohol in carbon tetrachloride, which chlorinated and treated with sodium fluoride to produce di-isopropylfluorophosphonate; (13) di-sec.-butyl fluorophosphonate is produced as in (12). Di-isopropyl hydrogen phosphite is obtained from isopropyl alcohol and phosphorus trichloride using ether or carbon tetrachloride as solvent or by direct treatment. Di-(1-carbethoxyethyl) hydrogen phosphite is obtained from ethyl lactate in carbon tetrachloride and phosphorous trichloride. Di-sec-butyl hydrogen phosphite is obtained from sec.-butyl alcohol in ether and phosphorus trichloride.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB601210A true GB601210A (en) | 1948-04-30 |
Family
ID=1731302
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1516043A Expired GB601210A (en) | 1943-09-15 | A process for the preparation of esters of fluorophosphonic acids and chlorophosphonic esters |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB601210A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2692890A (en) * | 1949-10-20 | 1954-10-26 | Monsanto Chemicals | Process for producing dialkyl phosphites |
| US2794820A (en) * | 1952-09-24 | 1957-06-04 | Monsanto Chemicals | Method of producing dialkyl and dicycloalkyl phosphites |
-
1943
- 1943-09-15 GB GB1516043A patent/GB601210A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2692890A (en) * | 1949-10-20 | 1954-10-26 | Monsanto Chemicals | Process for producing dialkyl phosphites |
| US2794820A (en) * | 1952-09-24 | 1957-06-04 | Monsanto Chemicals | Method of producing dialkyl and dicycloalkyl phosphites |
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