GB707961A - Improvements in or relating to the production of organic phosphorus compounds - Google Patents
Improvements in or relating to the production of organic phosphorus compoundsInfo
- Publication number
- GB707961A GB707961A GB1195648A GB1195648A GB707961A GB 707961 A GB707961 A GB 707961A GB 1195648 A GB1195648 A GB 1195648A GB 1195648 A GB1195648 A GB 1195648A GB 707961 A GB707961 A GB 707961A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chloride
- dichloride
- yield
- phosphonyl
- aluminium
- 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
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 150000002903 organophosphorus compounds Chemical class 0.000 title 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 15
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 abstract 9
- 150000001875 compounds Chemical class 0.000 abstract 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 5
- 230000007062 hydrolysis Effects 0.000 abstract 5
- 238000006460 hydrolysis reaction Methods 0.000 abstract 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 4
- 238000006243 chemical reaction Methods 0.000 abstract 4
- 238000000034 method Methods 0.000 abstract 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 239000004411 aluminium Substances 0.000 abstract 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 3
- 229910052782 aluminium Inorganic materials 0.000 abstract 3
- SWRNIYAQKATHDJ-UHFFFAOYSA-N dichloro(dichlorophosphanyl)phosphane Chemical compound ClP(Cl)P(Cl)Cl SWRNIYAQKATHDJ-UHFFFAOYSA-N 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- 239000012188 paraffin wax Substances 0.000 abstract 3
- CLWAXFZCVYJLLM-UHFFFAOYSA-N 1-chlorohexadecane Chemical compound CCCCCCCCCCCCCCCCCl CLWAXFZCVYJLLM-UHFFFAOYSA-N 0.000 abstract 2
- OWGJXSYVHQEVHS-UHFFFAOYSA-N 1-dichlorophosphorylethane Chemical compound CCP(Cl)(Cl)=O OWGJXSYVHQEVHS-UHFFFAOYSA-N 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 abstract 2
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 abstract 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 abstract 2
- 238000000354 decomposition reaction Methods 0.000 abstract 2
- 235000019441 ethanol Nutrition 0.000 abstract 2
- 229960003750 ethyl chloride Drugs 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 239000012442 inert solvent Substances 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- 125000005499 phosphonyl group Chemical group 0.000 abstract 2
- 229910052698 phosphorus Inorganic materials 0.000 abstract 2
- 239000011574 phosphorus Substances 0.000 abstract 2
- 239000000376 reactant Substances 0.000 abstract 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 abstract 1
- AATNZNJRDOVKDD-UHFFFAOYSA-N 1-[ethoxy(ethyl)phosphoryl]oxyethane Chemical compound CCOP(=O)(CC)OCC AATNZNJRDOVKDD-UHFFFAOYSA-N 0.000 abstract 1
- QKUNKVYPGIOQNP-UHFFFAOYSA-N 4,8,11,14,17,21-hexachlorotetracosane Chemical compound CCCC(Cl)CCCC(Cl)CCC(Cl)CCC(Cl)CCC(Cl)CCCC(Cl)CCC QKUNKVYPGIOQNP-UHFFFAOYSA-N 0.000 abstract 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 abstract 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 abstract 1
- 229940073608 benzyl chloride Drugs 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 150000001805 chlorine compounds Chemical class 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- FZXSSJIKXCFPDP-UHFFFAOYSA-N chloro(dichlorophosphoryl)methane Chemical compound ClCP(Cl)(Cl)=O FZXSSJIKXCFPDP-UHFFFAOYSA-N 0.000 abstract 1
- 125000004965 chloroalkyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 150000001983 dialkylethers Chemical class 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- QTBFPMKWQKYFLR-UHFFFAOYSA-N isobutyl chloride Chemical compound CC(C)CCl QTBFPMKWQKYFLR-UHFFFAOYSA-N 0.000 abstract 1
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 229940050176 methyl chloride Drugs 0.000 abstract 1
- SCLFRABIDYGTAZ-UHFFFAOYSA-N methylphosphonic acid dichloride Chemical compound CP(Cl)(Cl)=O SCLFRABIDYGTAZ-UHFFFAOYSA-N 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- UNFUYWDGSFDHCW-UHFFFAOYSA-N monochlorocyclohexane Chemical compound ClC1CCCCC1 UNFUYWDGSFDHCW-UHFFFAOYSA-N 0.000 abstract 1
- 125000006682 monohaloalkyl group Chemical group 0.000 abstract 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 abstract 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 abstract 1
- 150000003017 phosphorus Chemical class 0.000 abstract 1
- 125000006684 polyhaloalkyl group Chemical group 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/42—Halides thereof
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/28—Titanium 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have 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)
Abstract
Organic phosphonyl dichlorides are obtained by additively combining an organic chloride of the formula RCl in which R is an alkyl, cycloalkyl or aralkyl radical, or an alkenyl radical containing at least three carbon atoms, or a chloroalkyl radical, with phosphorus trichloride or a monoalkoxy phosphorus dichloride in the presence of anhydrous aluminium trichloride, and subjecting the resulting aluminium complex compound to decomposition by controlled hydrolysis. The process may be carried out in a modified form by first forming an organic chloride RCl in which R is an alkyl or chloroalkyl radical and a monoalkoxy or monochloroalkoxy phosphorus dichloride by reacting phosphorus trichloride and a dialkyl ether (or a sym.-dichlorodialkyl ether) in the presence of anhydrous aluminium chloride and then allowing the reaction to proceed to form the aluminium complex compound which is then subjected to decomposition by controlled hydrolysis. In another modification adapted for the production of an ester of a phosphonic acid the aluminium complex compound formed by reacting the organic chloride RCl with phosphorus trichloride or a monoalkoxy phosphorus dichloride in the presence of anhydrous aluminium chloride is treated with an alcohol, e.g. by the addition of an excess of ethyl alcohol, and the product then decomposed with water. The radical R in the first-mentioned formula RCl may be methyl, ethyl, n-propyl, isopropyl, n-, iso-, secondary- and tertiary-butyl, cetyl (hexadecyl), phenymethyl, and cyclohexyl. R also includes higher alkane radicals, thus the compound RCl may be a chlorinated paraffin hydrocarbon of an indefinite composition such as chlorinated white spirit or chlorinated paraffin wax. The term "chloroalkyl" includes polychlorinated methyl radicals but only includes higher radicals than methyl containing one chlorine atom. The process may be carried out by using the compound RCl and phosphorus trichloride in substantially equimolecular proportions a slight excess of the compound RCl being preferably used in the presence of at least one molecular proportion of aluminium chloride, but it is preferred to use two molecular proportions of aluminium chloride. The preparation of the complex is preferably carried out at room temperature although heating may be necessary to complete the reaction. When one or both of the reactants have a relatively high vapour pressure at room temperature the process may be carried out under pressure. The hydrolysis is carried out in a controlled manner advantageously at low temperature, e.g. in the neighbourhood of 0 DEG C. or somewhat lower, the complex as such or dissolved or suspended in a suitable solvent such as methylene chloride being decomposed by the addition of water which may, if desired, be in the form of ice or an emulsion or solution in an inert solvent. In an alternative method of hydrolysis the reaction conditions are selected so that the complex is in liquid form and is then hydrolysed by passing it through an aqueous zone, e.g. a layer of crushed ice, accompanied by a stream of heavy inert solvent which dissolves the hydrolysis product. It is stated that further hydrolysing of the product may result in the formation of a phosphinic acid and finally of a phosphonic acid. In examples: (1) to (15) phosphorus trichloride is used with the following organic chlorides: (1) and (4) ethyl chloride to yield ethyl phosphonyl dichloride; (2) isopropyl chloride to yield isopropylphosphonyl dichloride; (3) and (5) methyl chloride to yield methylphosphonyl dichloride; (6) isobutyl chloride to yield tert.-butyl phosphonyl dichloride; (7) cetyl chloride (n-hexadecyl chloride) to yield sec.-hexadecyl phosphonyl dichloride; (8) chlorocyclohexane to yield cyclohexylphosphonyl dichloride; (9) benzyl chloride to yield phenylmethyl - phosphonyl dichloride; (10) allyl chloride to yield allyl phosphonyl dichloride; (11) chlorinated white spirit which yields longchain hydrocarbon phosphonyl dichlorides mixed with a small proportion of partially chlorinated hydrocarbon phosphonyl dichlorides; in a similar manner chlorcosane (a chlorinated paraffin wax) yields a viscous mixture of phosphonyl dichloride derivatives; (12) methylene chloride, to yield chloromethyl phosphonyl dichloride; (13) chloroform to yield dichloromethylphosphonyl dichloride; (14) carbon tetrachloride to yield trichloromethylphosphonyl dichloride; (15) ethylene dichloride to yield 1 chloroethyl-2-phosphonyl-dichloride. In additional examples: (16) phosphorus ethoxy dichloride, aluminium chloride and n-propyl chloride are mixed at 0 DEG C. and the mixture finally heated to 70-80 DEG C. for one hour, and the product dissolved in methylene chloride and hydrolysed to isopropyl phosphonyl dichloride; (17) phosphorus isopropoxy dichloride, aluminium chloride, and tert-butyl chloride are warmed together at 60-70 DEG C. for thirty minutes and the product dissolved in methylene chloride and hydrolysed with water to yield tert.-butyl phosphonyl dichloride: (18) diethyl ether, aluminium chloride and phosphorus trichloride are heated together for six hours at 70-80 DEG C. and the product hydrolysed to give ethylphosphonyl dichloride; (19) di-(n-butyl ether), aluminium chloride and phosphorus trichloride are heated to 70-80 DEG C. for thirty minutes and the product hydrolysed to sec.-butyl phosphonyl dichloride; (20) sym.-dichlorodiethyl ether is refluxed with phosphorus trichloride and aluminium chloride and the product hydrolysed to form 1-chloroethyl-2-phosphonyl dichloride; (21) the complex derived from ethyl chloride, aluminium chloride and phosphorus trichloride is dissolved in methylene chloride; cooled and then treated with absolute ethyl alcohol until reaction ceases and the solution then treated with a small amount of water to yield diethyl-ethyl-phosphonate. According to the Provisional Specification any halide R.Hal, wherein R is an alkyl or mono- or poly-halo alkyl radical or other suitable radical, may be used and combined with a trivalent phosphorus derivative of the formula P.R1R11Hal, wherein R1 and R11 denote halogen or any suitable aliphatic radical in the presence of any agent which will form a molecular complex with the reactants, anhydrous aluminium bromide being specified as well as anhydrous aluminium chloride. It is also stated that the complex compound may be treated with an excess of water to yield a phosphonic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1195648A GB707961A (en) | 1948-04-30 | 1948-04-30 | Improvements in or relating to the production of organic phosphorus compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1195648A GB707961A (en) | 1948-04-30 | 1948-04-30 | Improvements in or relating to the production of organic phosphorus compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB707961A true GB707961A (en) | 1954-04-28 |
Family
ID=9995732
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1195648A Expired GB707961A (en) | 1948-04-30 | 1948-04-30 | Improvements in or relating to the production of organic phosphorus compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB707961A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3534127A (en) * | 1967-01-30 | 1970-10-13 | Geigy Chem Corp | Process for the preparation of phosphoryl compounds |
| CN106046052A (en) * | 2016-06-27 | 2016-10-26 | 安徽国星生物化学有限公司 | Synthesis method of glufosinate-ammonium intermediate methylphosphorus dichloride |
| CN112979702A (en) * | 2019-12-16 | 2021-06-18 | 常州诺法新材料科技有限公司 | Preparation method of organic phosphine compound |
-
1948
- 1948-04-30 GB GB1195648A patent/GB707961A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3534127A (en) * | 1967-01-30 | 1970-10-13 | Geigy Chem Corp | Process for the preparation of phosphoryl compounds |
| CN106046052A (en) * | 2016-06-27 | 2016-10-26 | 安徽国星生物化学有限公司 | Synthesis method of glufosinate-ammonium intermediate methylphosphorus dichloride |
| CN112979702A (en) * | 2019-12-16 | 2021-06-18 | 常州诺法新材料科技有限公司 | Preparation method of organic phosphine compound |
| CN112979702B (en) * | 2019-12-16 | 2024-02-20 | 常州诺法新材料科技有限公司 | Preparation method of organic phosphine compound |
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