US2880223A - Manufacture of dialkyl alkanephosphonates - Google Patents
Manufacture of dialkyl alkanephosphonates Download PDFInfo
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- US2880223A US2880223A US308726A US30872652A US2880223A US 2880223 A US2880223 A US 2880223A US 308726 A US308726 A US 308726A US 30872652 A US30872652 A US 30872652A US 2880223 A US2880223 A US 2880223A
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- complex
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- dialkyl
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- 238000004519 manufacturing process Methods 0.000 title description 5
- 238000000034 method Methods 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 15
- 239000007788 liquid Substances 0.000 claims description 13
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 12
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 12
- 238000009835 boiling Methods 0.000 claims description 7
- 150000004820 halides Chemical class 0.000 claims description 7
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 7
- 239000000725 suspension Substances 0.000 claims description 7
- 229940045803 cuprous chloride Drugs 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 239000012442 inert solvent Substances 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- 150000002430 hydrocarbons Chemical group 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 238000005979 thermal decomposition reaction Methods 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- ATLPLEZDTSBZQG-UHFFFAOYSA-L dioxido-oxo-propan-2-yl-$l^{5}-phosphane Chemical compound CC(C)P([O-])([O-])=O ATLPLEZDTSBZQG-UHFFFAOYSA-L 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 150000001350 alkyl halides Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 3
- -1 sodium alkoxide Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- GBHRVZIGDIUCJB-UHFFFAOYSA-N hydrogenphosphite Chemical compound OP([O-])[O-] GBHRVZIGDIUCJB-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- NCPXQVVMIXIKTN-UHFFFAOYSA-N trisodium;phosphite Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])[O-] NCPXQVVMIXIKTN-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
-
- 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
- C07F9/142—Esters of phosphorous acids with hydroxyalkyl compounds without 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
- C07F9/28—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
-
- 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
Definitions
- This invention relates a improvements inth'e maufracture of dialkyl alkanephosphonates.
- This method of preparing the dialkyl alkanephosphona-tes suffers from marked disadvantages because, on the one hand, the trialkyl phosphites are compounds which are diflicultly accessible on a commercial .
- This method is greatly superior to that in Equation No. 1 where dialkyl alkanephosphonates are to be prepared in whichR and R' represent different alkyl groups.
- This method also has the marked disadvantage that it involves the use of metallic sodium on a large scale in connection with the manufacture of sodium alkoxide or of powdered sodium for the conversion of the dialkyl hydrogen phosphite to the desired dialkyl sodium phosphite and the hazards involved in the use of metallic sodium on a large scale are obvious.
- dialkyl alkanephosphonates conveniently by processes which avoid the use of trialkyl phosphites (which are themselves somewhat sensitive to traces of moisture, particularly in the case of trimethyl phosphite) and which also overcome the disadvantage of the use of metallic sodium by the second above-mentioned method.
- the present invention is based upon the discovery that a cuprous halide addition compound or complex with a trialkyl phosphite undergoes thermal decomposition, yielding as a reaction product the desired dialkyl alkanephosphonate.
- the invention also provides a process for the manufacture of dialkyl alkanephosphonates which comprises reacting a cuprous halide with a phosphorus t'rihalide and with an alkanol in the'cold and thereafter subjecting the cuprous halide-alkyl phosphite addition compound or complex therebyproduced to thermal decomposition.
- cuprous halide compound which is most convenient is cuprous chloride and "the phosphorus trihalide which is "most convenient is' phosphorus trichloride.
- the decomposition of the cuprous halide addition compound or complex which ma he represented by the decomposition in this way produces yields a which are somewhat low, which may be iln the neighbourhood of 20%
- the invention therefore consists in that the thermal decomposition of the cuprous halidjealkyl phosphite addition compound or complex is elfected by heating the, said additioncompound or complex in suspension in a medium whichis an inert and stable liquid at the temperature of the thermal decomposition.
- the reaction may, for example, be carried out in a high boiling solvent such as diphenyl or diphenyl ether.
- the present invention is not confined to the .PrQ uction of dialkyl alkan'ephosp'honates in which all of the talk-y ⁇ groups are identical but includes the case where the cuproufs halide and phos- "phorus trihalide are reactedtogether with a :mixture of aliphatic alcohols.
- Example solid product (CH O) P.CuCl was filtered 01f, washed with dry petrol (200 ml.) and dried in a vacuum' desiccator. The yield was of the theoretical amount.
- a process of preparing -a complex of the formula (RO) P.CuX wherein R is a lower aliphatic hydrocarbon group and X is selected from the class consisting of chlorine, bromine and iodine which comprises forming a mixture consisting essentially of at least one lower unsubstituted alkanol, a cuprous halide and an inert solvent, and adding phosphorus trichloride to said mixture at a temperature of the order of -5 C. while agitating said mixture.
- a process 'of preparing a lower unsubstituted dialkyl alkanephosphonate which comprises suspending in a high fboiling liquid a complex of the formula (RO) P.CuCl, wherein R represents an unsubstituted lower alkyl group,
- a method of preparing a lower dialkyl alkanephosphonate which comprises reacting a lower unsubstituted alkanol with cuprouswchloride-and phosphorus trichloride to form the complex (KO) P.CuCl, where R is a lower unsubstituted alkylgroup, and then suspendingsaid complex in a high boiling liquid and heatingthe'resulting suspension at a temperature of substantially 200 C. and a pressure of the order of, but not below, normal atmospheric pressure to thereby decompose said complex and produce said lower dialkyl methanephosphonate, said liquid being one which is inert and-stable at said temperature and pressure.
- a method of producing a lower dialkyl alkanephosphonate which comprises forming a mixtureco'nsisting essentially of at least one unsubstituted lower alkanol,
- cuprous chloride and an inert solvent adding phosphorus 7.
- a process as defined in claim 6 wherein said high boiling'liquid is selected from the group consistingof d p e yl n iphcny ltsi't Davis 'et"al.:
- a process of producing dimethyl methanephosphonate which comprises forming a mixture of methanol, cuprous chloride, and an inert solvent, adding phosphorus trichloride to said mixture at a temperature of the order of --5 C. while stirring said mixture, thereby forming a complex of the formula (CH O) P.CuCl, suspending said'complex in a'high-boiling liquid and decomposing said complex by heating the suspension thus formed at a temperature of substantially 200 C. and a pressure of the order of, but not less than, ordinary atmospheric pressure, said high boilingliquid being one which'is inert and stable at said temperature and pressure.
- a process as defined in claim 8 wherein said high boiling liquid. is selected from the group consisting of :liphenyl diphenylether..
- a process of preparing dimethyl methanephosphonate which comprisesislowly adding phosphorus trichloride to a mixture of'cuprous chloride and methanol in toluene with stirringata temperature of substantially 5 C., thereby forming the complex (CH O) P.CuCl, removing said omple x from said toluene,- suspending said complex in. diphenylether, decomposing said com- .plex by heating the suspension thus formed substantially to 200 C. with stirring, at atmospheric pressure thereby forming dimethyl methanephosphonate,
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
Description
tates No Drawing. Application Septemher 9, 1952 Serial No. 308,726
lilaiil sfpriority, applicationiGreatBritai "Sl mmb r 9 10 Claims. {CL 16091-138) This invention relates a improvements inth'e maufracture of dialkyl alkanephosphonates.
There are already available methods described in the chemical literature for the preparation of dialkyl alkanephosphonates of which the two principal methods are as follows. First, a trialkyl phosphite is reacted with an alkyl halide, preferably the bromide oriodi'de, "in accordance with the well-known Ar'busov reaction which proceeds in accordance with the following equation- Ii -this equation Rand R' indicate alkyl groups and X indicates a halogen atom. In this process whe'reR and .R' are the same it is only necessary to use verysmall quantities of the alkyl halide since, as will be seen from the above Equation 1 the alkyl halide is regenerated.
This method of preparing the dialkyl alkanephosphona-tes, however, suffers from marked disadvantages because, on the one hand, the trialkyl phosphites are compounds which are diflicultly accessible on a commercial .This method is greatly superior to that in Equation No. 1 where dialkyl alkanephosphonates are to be prepared in whichR and R' represent different alkyl groups. This method, however, also has the marked disadvantage that it involves the use of metallic sodium on a large scale in connection with the manufacture of sodium alkoxide or of powdered sodium for the conversion of the dialkyl hydrogen phosphite to the desired dialkyl sodium phosphite and the hazards involved in the use of metallic sodium on a large scale are obvious.
We have now found that we can produce dialkyl alkanephosphonates conveniently by processes which avoid the use of trialkyl phosphites (which are themselves somewhat sensitive to traces of moisture, particularly in the case of trimethyl phosphite) and which also overcome the disadvantage of the use of metallic sodium by the second above-mentioned method.
The present invention is based upon the discovery that a cuprous halide addition compound or complex with a trialkyl phosphite undergoes thermal decomposition, yielding as a reaction product the desired dialkyl alkanephosphonate.
According to the present invention therefore there is formula 2,880,223 Patented J Mar. 31, 1959 ice 2 provided a process lf or the "manufacture of, dialkyl aligneph'osphonates which comprisessubje'eting a cuprous halide addition compound or complex with 'atrialkylphosphite "to thermal decomposition.
The inventionalso provides a process for the manufacture of dialkyl alkanephosphonates which comprises reacting a cuprous halide with a phosphorus t'rihalide and with an alkanol in the'cold and thereafter subjecting the cuprous halide-alkyl phosphite addition compound or complex therebyproduced to thermal decomposition.
The cuprous halide compound which is most convenient is cuprous chloride and "the phosphorus trihalide which is "most convenient is' phosphorus trichloride.
The decomposition of the cuprous halide addition compound or complex which ma he represented by the decomposition in this way, however, produces yields a which are somewhat low, which may be iln the neighbourhood of 20% A feature of .the invention therefore consists in that the thermal decomposition of the cuprous halidjealkyl phosphite addition compound or complex is elfected by heating the, said additioncompound or complex in suspension in a medium whichis an inert and stable liquid at the temperature of the thermal decomposition. The reaction may, for example, be carried out in a high boiling solvent such as diphenyl or diphenyl ether.
It will be appreciated that the present invention is not confined to the .PrQ uction of dialkyl alkan'ephosp'honates in which all of the talk-y} groups are identical but includes the case where the cuproufs halide and phos- "phorus trihalide are reactedtogether with a :mixture of aliphatic alcohols.
In our copending application, S.;N. 308.72 7, we have disclosed the production of other'compounds by decomposition of this complex.
The following example will serve toillust'rate'the manner in which the present inventioil ma'y 'be carried into effect.
Example solid product (CH O) P.CuCl was filtered 01f, washed with dry petrol (200 ml.) and dried in a vacuum' desiccator. The yield was of the theoretical amount.
A portion of the white solid thus prepared was rapidly suspended in diphenyl ether and the mixture heated with stirring to 200 C. When decomposition was complete the dimethyl methanephosphonate was distilled out from the diphenyl ether under vacuum (12 mm.). The yield was approximately 70% of the theoretical amount.
We claim:
1. A process of preparing -a complex of the formula (RO) P.CuX wherein R is a lower aliphatic hydrocarbon group and X is selected from the class consisting of chlorine, bromine and iodine which comprises forming a mixture consisting essentially of at least one lower unsubstituted alkanol, a cuprous halide and an inert solvent, and adding phosphorus trichloride to said mixture at a temperature of the order of -5 C. while agitating said mixture.
2; A 'pro'cess 'br' isrefisiiag '(CH O) P.CuCl whic'hcomprises forming a mixture conagitating said mixture.
a complex of the formula sisting essentially of methanol, cuprous chloride and an inert solvent and adding phosphorus. trichloride to said mixture at a temperature of the order of 5 C. while 3. A process 'of preparing a lower unsubstituted dialkyl alkanephosphonate which comprises suspending in a high fboiling liquid a complex of the formula (RO) P.CuCl, wherein R represents an unsubstituted lower alkyl group,
heating said suspension to a temperature of substantially 200, C. at a pressure of the order of, but not below, normal atmospheric pressure, said liquid being one which is inert and stable. at. said .temperature'and pressure.
4. A method as defined in cla'im3 wherein said liquid is selected from the group consisting of diphenylether and diphenyl. 7 1 j e r 5. A method of preparing a lower dialkyl alkanephosphonate which comprises reacting a lower unsubstituted alkanol with cuprouswchloride-and phosphorus trichloride to form the complex (KO) P.CuCl, where R is a lower unsubstituted alkylgroup, and then suspendingsaid complex in a high boiling liquid and heatingthe'resulting suspension at a temperature of substantially 200 C. and a pressure of the order of, but not below, normal atmospheric pressure to thereby decompose said complex and produce said lower dialkyl methanephosphonate, said liquid being one which is inert and-stable at said temperature and pressure.
6. A method of producing a lower dialkyl alkanephosphonate which comprises forming a mixtureco'nsisting essentially of at least one unsubstituted lower alkanol,
cuprous chloride and an inert solvent, adding phosphorus 7. A process as defined in claim 6 wherein said high boiling'liquid is selected from the group consistingof d p e yl n iphcny ltsi't Davis 'et"al.:
8. A process of producing dimethyl methanephosphonate which comprises forming a mixture of methanol, cuprous chloride, and an inert solvent, adding phosphorus trichloride to said mixture at a temperature of the order of --5 C. while stirring said mixture, thereby forming a complex of the formula (CH O) P.CuCl, suspending said'complex in a'high-boiling liquid and decomposing said complex by heating the suspension thus formed at a temperature of substantially 200 C. and a pressure of the order of, but not less than, ordinary atmospheric pressure, said high boilingliquid being one which'is inert and stable at said temperature and pressure.
9. A process as defined in claim 8 wherein said high boiling liquid. is selected from the group consisting of :liphenyl diphenylether..
10. A process of preparing dimethyl methanephosphonate which comprisesislowly adding phosphorus trichloride to a mixture of'cuprous chloride and methanol in toluene with stirringata temperature of substantially 5 C., thereby forming the complex (CH O) P.CuCl, removing said omple x from said toluene,- suspending said complex in. diphenylether, decomposing said com- .plex by heating the suspension thus formed substantially to 200 C. with stirring, at atmospheric pressure thereby forming dimethyl methanephosphonate,
Referenees Citedfin the file of this patent UNITED STATES PATENTS -Woodstoek Nov. 22, 1938, OTHER REFERENCES ArbusOff: Berichte der Deu. Chen 1., vol. 38 (1905),
35 I Lindet: Annales de Chemie et de Physique 6, 11, pp.
Beilstein: Band I (Bis 1 Jan. 1910), p. 285, line 16 -J. Am. Chem. Soc. 58, 2151-2153 'Arbuzov et al.: Chem. Abstracts, vol. 29 (1935), p.
2146. (Abstract of Jour. Gen. Chem. USSR, vol. 4
Claims (3)
1. A PROCESS OF PREPARING A COMPLEX OF THE FORMULA (RO)3P.CUX WHERIN R IS A LOWER ALPHATIC HYDROCARBON GROUP AND X IS SELECTED FROM THE CLASS CONSISTING OF CHLORINE, BROMINE AND IODINE WHICH COMPRISES FORMING A MIXTURE CONSISTING ESSENTIALLY OF AT LEAST ONE LOWER UNSUBSTITUDE ALKANOL, A CUPROUS HALIDE AND AN INERT SOLVENT, AND ADDING PHOSPHOROUS TRICHLORIDE TO SAID MIXTURE AT A TEMPERATURE OF THE ORDER OF -5*C. WHILE AGITATING SAID MIXTURE
3. A PROCESS OF PREPARING A LOWER UNSUBSTITUTED DIALKYL ALKANEPHOSPHONATE WHICH COMPRISES USPENDING IN A HIGH BOILING LIQUID A COMPLEX OF THE FORMULA (RO)3P.CUCL, WHEREIN R REPRESENTS AN UNSUBSTITUTED LOWER ALKYL GROUP, HEATING SAID SUSPENSION TO A TEMPERATURE OF SUBSTANTIALLY 200*C. AT A PRESSURE OF THE ORDER OF, BUT NOT BELOW, NORMAL ATMOSPHERIC PRESSURE, SAID LIQUID BEING ONE WHICH IS INERT AND STABLE AT SAID TEMPERATURE AND PRESSURE.
5. A METHOD OF PREPEARING A LOWER DIALKYL ALKANEPHOSPHONATE WHICH COMPRISES REACTING A LOWER UNSUBSTITUTED ALKANOL WITH CUPROUS CHLORIDE AND PHOSPHOROUS TRICHLORIDE TO FORM THE COMPLEX (RO)3P.CUCL, WHERE R IS A LOWER UNSUBSTITUTED ALKYL GROUP, AND THEN SUSPENDING SAID COMPLEX IN A HIGH BOILING LIQUID AND HEATING THE RESULTING SUSPENSION AT A TEMPERATURE OF SUBSTANTIALLY 200*C. AND A PRESSURE OF THE ORDER OF, BUT NOT BELOW, NORMAL ATMOSPHERIC PRESSURE TO THEREBY DECOMPOSED SAID COMPLEX AND PRODUCE SAID LOWER DIALKYL METHANEPHOSPHONATE, SAID LIQUID BEING ONE WHICH IS INERT AND STABLE AT AID TEMPER
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2880223X | 1951-09-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2880223A true US2880223A (en) | 1959-03-31 |
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ID=10917049
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US308726A Expired - Lifetime US2880223A (en) | 1951-09-13 | 1952-09-09 | Manufacture of dialkyl alkanephosphonates |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2880223A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3064025A (en) * | 1959-08-14 | 1962-11-13 | Phillips Petroleum Co | Alkyl thioether and dithioether-heavy metal cyanide addition compounds |
| US3294870A (en) * | 1964-03-24 | 1966-12-27 | American Cyanamid Co | Organophosphorus-copper complex compounds and their use for producing fire retardant plastics |
| US3884997A (en) * | 1973-05-02 | 1975-05-20 | Du Pont | Process for preparation of aromatic phosphorus compounds |
| US3933878A (en) * | 1972-06-02 | 1976-01-20 | Exxon Research And Engineering Company | Ligand complexes of cu(1)salts |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2137792A (en) * | 1936-09-12 | 1938-11-22 | Victor Chemical Works | Organic phosphorus-containing compounds |
-
1952
- 1952-09-09 US US308726A patent/US2880223A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2137792A (en) * | 1936-09-12 | 1938-11-22 | Victor Chemical Works | Organic phosphorus-containing compounds |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3064025A (en) * | 1959-08-14 | 1962-11-13 | Phillips Petroleum Co | Alkyl thioether and dithioether-heavy metal cyanide addition compounds |
| US3294870A (en) * | 1964-03-24 | 1966-12-27 | American Cyanamid Co | Organophosphorus-copper complex compounds and their use for producing fire retardant plastics |
| US3933878A (en) * | 1972-06-02 | 1976-01-20 | Exxon Research And Engineering Company | Ligand complexes of cu(1)salts |
| US3884997A (en) * | 1973-05-02 | 1975-05-20 | Du Pont | Process for preparation of aromatic phosphorus compounds |
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