US2908708A - Process for preparing phosphonates - Google Patents
Process for preparing phosphonates Download PDFInfo
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- US2908708A US2908708A US436731A US43673154A US2908708A US 2908708 A US2908708 A US 2908708A US 436731 A US436731 A US 436731A US 43673154 A US43673154 A US 43673154A US 2908708 A US2908708 A US 2908708A
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- US
- United States
- Prior art keywords
- methyl
- phosphite
- phosphate
- acid
- reaction
- 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 - Lifetime
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- 238000004519 manufacturing process Methods 0.000 title claims description 10
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 title description 8
- 150000004702 methyl esters Chemical class 0.000 claims description 18
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 16
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims description 11
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 8
- 150000003018 phosphorus compounds Chemical class 0.000 claims description 3
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 18
- 239000000047 product Substances 0.000 description 14
- 238000000197 pyrolysis Methods 0.000 description 12
- MXBDBLBKBBAYGD-UHFFFAOYSA-N P(O)(O)=O.C Chemical class P(O)(O)=O.C MXBDBLBKBBAYGD-UHFFFAOYSA-N 0.000 description 11
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 10
- XAKRTGZVYPZHCO-UHFFFAOYSA-O hydroxy-methoxy-oxophosphanium Chemical compound CO[P+](O)=O XAKRTGZVYPZHCO-UHFFFAOYSA-O 0.000 description 9
- CAAULPUQFIIOTL-UHFFFAOYSA-N methyl dihydrogen phosphate Chemical class COP(O)(O)=O CAAULPUQFIIOTL-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- YLFBFPXKTIQSSY-UHFFFAOYSA-N dimethoxy(oxo)phosphanium Chemical compound CO[P+](=O)OC YLFBFPXKTIQSSY-UHFFFAOYSA-N 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- KKUKTXOBAWVSHC-UHFFFAOYSA-N Dimethylphosphate Chemical class COP(O)(=O)OC KKUKTXOBAWVSHC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- CZHYKKAKFWLGJO-UHFFFAOYSA-N dimethyl phosphite Chemical compound COP([O-])OC CZHYKKAKFWLGJO-UHFFFAOYSA-N 0.000 description 6
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 6
- 229910019142 PO4 Inorganic materials 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 235000021317 phosphate Nutrition 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 3
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 229940042400 direct acting antivirals phosphonic acid derivative Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- -1 methane phosphonates Chemical compound 0.000 description 1
- FISRGBICZQXBOD-UHFFFAOYSA-N methane phosphoric acid Chemical compound C.C.OP(O)(O)=O FISRGBICZQXBOD-UHFFFAOYSA-N 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical class C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- DGVNWNYQSOYWKZ-UHFFFAOYSA-N methyl dihydrogen phosphite Chemical class COP(O)O DGVNWNYQSOYWKZ-UHFFFAOYSA-N 0.000 description 1
- 239000012022 methylating agents Substances 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- ZOGYOOUMDVKYLM-UHFFFAOYSA-N phosphane phosphorous acid Chemical compound P.OP(O)O ZOGYOOUMDVKYLM-UHFFFAOYSA-N 0.000 description 1
- IBIRZFNPWYRWOG-UHFFFAOYSA-N phosphane;phosphoric acid Chemical compound P.OP(O)(O)=O IBIRZFNPWYRWOG-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- 150000003007 phosphonic acid derivatives Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 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)]
- C07F9/3895—Pyrophosphonic acids; phosphonic acid anhydrides
Definitions
- This invention relates to a method for converting a phosphorous compound, e,g. phosphite or a phosphorous acid, to a phosphonate, particularly methane phosphonates, by reaction with an ester of a phosphoric acid, particularly selected from the methyl esters.
- a phosphorous compound e.g. phosphite or a phosphorous acid
- a phosphonate particularly methane phosphonates
- Methane phosphonic acid derivatives have been made by pyrolysis of dimethyl phosphite ,alone but not by reaction of the phosphite ester or of phosphorous acid with an ester of another oxy-acid, particularly such as a phosphoric acid.
- the desired methane phosphonic acid derivatives are represented by the following general formula:
- the reaction product was cooled and Weighed, then analyzed for P and P methane phosphoric acid, and total phosphorus content.
- reaction products are clear, Colorless liquids with densities above 1.0.
- the products On extended cooling at temperatures below 100' C., the products become solidi fied.
- the products On reheating the products are reliquefied.
- the products are water-soluble.
- Sample A and Sample E contained by analysis of their aqueous solutions about 82 mole percent total phosphites including 52 mole percent monomethyl phosphite, 30% H PO and 1% dimethyl phosphite. These mixtures were obtained as bottoms in the distillation of crude dimethyl phosphite (DMHP).
- DMHP crude dimethyl phosphite
- DMHP dimethyl hydrogen phosphite
- the present invention contemplates the production of dimethyl phosphate along with dimethyl phosphite by judicious addition of POCl to the PC1 feed to methanol to form such a mixture.
- Another embodiment of this invention involves the addition of trimethyl phosphate or similar ester to the reaction mixture in the pyrolysis of dimethyl hydrogen phosphite at the proper time for obtaining maximum yield.
- this invention envisions the addition of the methyl ester to a point near the end of the pyrolysis.
- the ester is added to the effluent before or during addition of the efiluent to a final pyrolysis state.
- methyl esters such as trimethyl phosphate does not exclude the use of BF or other such catalysts.
- BF may also have been added.
- One attractive process involves the use of BF;, to catalyze the desired reactions at the beginning and the addition of methyl phosphates to give better yields during the last half of the reaction when large amounts of unconverted phosphites such as monomethyl phosphite and H PO are present.
- staged pyrolysis such as that above it is advantageous to use methyl phosphates in the higher temperature, second stage. B1 is especially beneficial at lower temperature early stages. 7
- trimethyl phosphate is a more desirable methylating agent, it costs more than dior monomethyl phosphate. On the basis of equal methyl content it may be no more desirable.
- the last methyl i.e., the one visualized as held by the weakly acid POH, is the reactive one.
- the trimethyl phosphate has two methyls in reserve but the active methyl is the same as or similar in activity to that in mono- 4 methyl phosphate. This concept is not to be construed as limiting the invention.
- the temperature required for the above-discussed methylations ranges between an upper limit of about 350 C. and a lower limit determined by that resulting from spontaneous reaction of the cold reagents. It is believed that C. to 275 C. is a preferred operating range.
- the amounts of methylating agents used is of course influenced by many considerations including the feed composition, catalyst, temperature and the economics of the particular reaction. Excess trimethyl phosphate of course would give the maximum yield and fastest reaction according to the present interpretation of the data.
- Phosphates are desirable agents since present processes for phosphite pyrolysis include systems for handling these pyrolytic products. Borates are attractive because of the possibility that they might be regenerable with methanol treat to give volatile trimethyl borate.
- Products of this invention may be employed in preparing fuel, lubricating oil, and grease additives, detergents, fire retardants, insecticides, and plasticizers.
- the methane phosphonic acids undergo reaction with alcohols, esters, salts, bases, as well as with halogens and nonmetallic halides.
- Process for preparing a methane phosphonate which comprises reacting a phosphorous compound selected from the group consisting of phosphorous acid and methyl esters thereof with a methyl ester of a phosphoric acid.
- Process for preparing a methane phosphonic acid and methyl esters thereof which comprises reacting a phosphite with a methyl ester of a phosphoric acid.
- Process for preparing a methane phosphonic acid and a methyl ester thereof which comprises reacting a phosphorous acid with a methyl ester of a phosphoric acid.
- Process for preparing methane phosphonic acid and a methyl ester thereof which comprises heating a mixture containing phosphorous acid and mono-methyl phosphite with a mixture containing monoand dimethyl phosphate to temperatures in the range of 100 to 350 C.
- Process for preparing a methane phosphonic acid and methyl esters thereof which comprises heating a mixture containing phosphorous acid and mono-methyl phosphite with trimethyl phosphate to temperatures in the range of 100 to 350 C.
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- 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)
Description
United States Patent No Drawing. Application June 14,1954
Serial No. 436,731
6 Claims. (Cl. 260-461) This invention relates to a method for converting a phosphorous compound, e,g. phosphite or a phosphorous acid, to a phosphonate, particularly methane phosphonates, by reaction with an ester of a phosphoric acid, particularly selected from the methyl esters.
Methane phosphonic acid derivatives have been made by pyrolysis of dimethyl phosphite ,alone but not by reaction of the phosphite ester or of phosphorous acid with an ester of another oxy-acid, particularly such as a phosphoric acid.
For the present invention, it was found that "(the methane'phosphonic acid derivatives can be obtained by reaction of phosphorous acid or methyl phosphites with methyl esters of phosphoric acid, and the yields of desired product are better than in the absence of the methyl phosphate esters. p
The desired methane phosphonic acid derivatives are represented by the following general formula:
0 CH;-'P0R1 .O-Rz wherein R and R stand for hydrogen, methyl, or. a phosphorus-containing radical. Specific .examples of these derivatives are:
V OH3POH (Em-$ 0011.
OH .OH Methane phosphonic Mono methyl methane acid phosphonic acid iPyro methane phosphonic acid CHa-P "Trimeric methane phosphonic acid ,anhydride EXAMPLES was stopped after a period of from 10 minutes to about 60 minutes. The trimethyl phosphate gave the quickest V H P 0 =Phosphorous acid 2,908,708 Patented Oct. 13, 1959 reaction for same extent of conversion at a given temperature.
The reaction product was cooled and Weighed, then analyzed for P and P methane phosphoric acid, and total phosphorus content.
In general, the reaction products are clear, Colorless liquids with densities above 1.0. On extended cooling at temperatures below 100' C., the products become solidi fied. On reheating the products are reliquefied. The products are water-soluble.
The product obtained and described is useful as such, without further purification.
Other specific examples of the desired derivatives of the methane phosphonic acids shown are the dimethyl ester derivatives.
Improvements in yields of the desired methane phosphonic acid derivatives obtained by using the process of the present invention are shown in the following Table I.
Table I [All samples heated slowly in pairs to reaction temperature, 270 0.]
MMHP=Monomethyl phosphite DMHP=Dimethyl phosphite MP=Mixed monoand di-methyl phosphates Me l 0 =Trimethy1 phosphate P Phosphite phosphorus P =gndzcsired phosphate phosphorus of phosphate and phosphine pro uc s.
The summarized data in Table I shows in the duplicate experiments C and D that the presence of an equal amount of trimethyl phosphate did not affect the percentage of I I PO decomposed but changed the course of this decomp'osition from 100% undesired products to 97% desired products methane phosphonic acid derivatives,
In the pair of experiments G and H, mixed monoand di-methyl phosphates caused H PO to yield selectively 62% of the desired methane phosphonic acid derivatives instead of giving 100% conversion to undesired products.
The mixture of monomethyl phosphite and phosphorus acid referred to in the Table I as Sample A and Sample E contained by analysis of their aqueous solutions about 82 mole percent total phosphites including 52 mole percent monomethyl phosphite, 30% H PO and 1% dimethyl phosphite. These mixtures were obtained as bottoms in the distillation of crude dimethyl phosphite (DMHP).
In the absence of the added methyl phosphates or V similarly reacting esters, there is a low yield of only 20% of the desired products per pass or per fresh batch. In the duplicate experiment B, the added trimethyl phosphate raised the conversion to from 37% and :changed the yield to 82% of desired products per pass, which is a considerable advantage. Similarly, in the experimentsE and F the mixed added methyl phosphates enhanced the yield of desired products although under these conditions they did not change the total phosphite conversion level very much.
It has been found that dimethyl hydrogen phosphite (DMHP) when pyrolyzed initially forms no appreciable amount of phosphates. As the pyrolysis reaction proceeds, substantial amounts of material which analyzes in aqueous solutions as monomethyl phosphite (MMHP) and H PO form. Consequently as the pyrolysis is continued these are converted into more undesired products, phosphates and phosphines. Accordingly, it is beneficial to add methyl phosphate esters at some stage of the pyrolysis for conversion of phosphites to the desired phosphonate derivatives.
In the examples given in the Table I, extraneous phosphate esters were added to the phosphite pyrolysis feeds to ascertain the specific ajfects of the phosphate esters. In an improved embodiment, the present invention contemplates the production of dimethyl phosphate along with dimethyl phosphite by judicious addition of POCl to the PC1 feed to methanol to form such a mixture.
Another embodiment of this invention involves the addition of trimethyl phosphate or similar ester to the reaction mixture in the pyrolysis of dimethyl hydrogen phosphite at the proper time for obtaining maximum yield.
In the staged recirculating pyrolysis of DMHP this invention envisions the addition of the methyl ester to a point near the end of the pyrolysis. For example in an apparatus containing two circulating units the ester is added to the effluent before or during addition of the efiluent to a final pyrolysis state.
The use of methyl esters such as trimethyl phosphate does not exclude the use of BF or other such catalysts. In fact where trimethyl or dimethyl phosphate is added to DMHP in a pyrolysis reaction, BF may also have been added. One attractive process involves the use of BF;, to catalyze the desired reactions at the beginning and the addition of methyl phosphates to give better yields during the last half of the reaction when large amounts of unconverted phosphites such as monomethyl phosphite and H PO are present.
In staged pyrolysis such as that above it is advantageous to use methyl phosphates in the higher temperature, second stage. B1 is especially beneficial at lower temperature early stages. 7
Study of the action of trior dimethyl phosphate on phosphorous acid indicates that ester interchange may occur. This concept does not limit the invention, however, and is not meant to indicate that monoor dimethyl phosphite is essential to the production of methane phosphonic acid derivatives.
While trimethyl phosphate is a more desirable methylating agent, it costs more than dior monomethyl phosphate. On the basis of equal methyl content it may be no more desirable. One view holds that the last methyl, i.e., the one visualized as held by the weakly acid POH, is the reactive one. On this basis the trimethyl phosphate has two methyls in reserve but the active methyl is the same as or similar in activity to that in mono- 4 methyl phosphate. This concept is not to be construed as limiting the invention.
The temperature required for the above-discussed methylations ranges between an upper limit of about 350 C. and a lower limit determined by that resulting from spontaneous reaction of the cold reagents. It is believed that C. to 275 C. is a preferred operating range. The amounts of methylating agents used is of course influenced by many considerations including the feed composition, catalyst, temperature and the economics of the particular reaction. Excess trimethyl phosphate of course would give the maximum yield and fastest reaction according to the present interpretation of the data.
Phosphates are desirable agents since present processes for phosphite pyrolysis include systems for handling these pyrolytic products. Borates are attractive because of the possibility that they might be regenerable with methanol treat to give volatile trimethyl borate.
In special cases other methyl esters might be more desirable.
It is envisioned that mixtures of methyl esters might be especially interesting. Methyl chloride in methyl phosphate or borate is suggested.
Products of this invention may be employed in preparing fuel, lubricating oil, and grease additives, detergents, fire retardants, insecticides, and plasticizers. The methane phosphonic acids undergo reaction with alcohols, esters, salts, bases, as well as with halogens and nonmetallic halides.
In addition to the preceding ideas many others will now be obvious to those skilled in the art.
The invention described is claimed as follows:
1. Process for preparing a methane phosphonate which comprises reacting a phosphorous compound selected from the group consisting of phosphorous acid and methyl esters thereof with a methyl ester of a phosphoric acid.
2. Process for preparing a methane phosphonate by reacting a phosphorous acid and a methyl ester thereof with a methyl ester of a phosphoric acid.
3. Process for preparing a methane phosphonic acid and methyl esters thereof which comprises reacting a phosphite with a methyl ester of a phosphoric acid.
4. Process for preparing a methane phosphonic acid and a methyl ester thereof which comprises reacting a phosphorous acid with a methyl ester of a phosphoric acid.
5. Process for preparing methane phosphonic acid and a methyl ester thereof which comprises heating a mixture containing phosphorous acid and mono-methyl phosphite with a mixture containing monoand dimethyl phosphate to temperatures in the range of 100 to 350 C.
6. Process for preparing a methane phosphonic acid and methyl esters thereof which comprises heating a mixture containing phosphorous acid and mono-methyl phosphite with trimethyl phosphate to temperatures in the range of 100 to 350 C.
No references cited.
Claims (1)
1. PROCESS FOR PREPARING A METHOANE PHOSPHONATE WHICH COMPRISES REACTING A PHOSPHOROUS COMPOUND SELECTED FROM THE GROUP CONSISTING OF PHOSPHOROUS ACID AND METHYL ESTERS THEREOF WITH A METHYL ESTER OF A PHOSPHORIC ACID.
Priority Applications (1)
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US436731A US2908708A (en) | 1954-06-14 | 1954-06-14 | Process for preparing phosphonates |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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US436731A US2908708A (en) | 1954-06-14 | 1954-06-14 | Process for preparing phosphonates |
Publications (1)
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US2908708A true US2908708A (en) | 1959-10-13 |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3064031A (en) * | 1962-02-05 | 1962-11-13 | Procter & Gamble | Process for preparing dialkyl alkyl phosphonates |
US3620672A (en) * | 1968-08-19 | 1971-11-16 | Armstrong Cork Co | Method of preparing anhydrous phosphorus acid |
US4041111A (en) * | 1975-03-04 | 1977-08-09 | Purdue Research Foundation | Phosphonate monoesters and method of preparation |
US6545073B1 (en) * | 2000-08-24 | 2003-04-08 | David H. Blount | Organic phosphorus-inorganic phosphorus oxyacids compounds and compositions |
-
1954
- 1954-06-14 US US436731A patent/US2908708A/en not_active Expired - Lifetime
Non-Patent Citations (1)
Title |
---|
None * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3064031A (en) * | 1962-02-05 | 1962-11-13 | Procter & Gamble | Process for preparing dialkyl alkyl phosphonates |
US3620672A (en) * | 1968-08-19 | 1971-11-16 | Armstrong Cork Co | Method of preparing anhydrous phosphorus acid |
US4041111A (en) * | 1975-03-04 | 1977-08-09 | Purdue Research Foundation | Phosphonate monoesters and method of preparation |
US6545073B1 (en) * | 2000-08-24 | 2003-04-08 | David H. Blount | Organic phosphorus-inorganic phosphorus oxyacids compounds and compositions |
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