GB934090A - Chloromethylphosphinic acid, salts thereof, and method of preparation - Google Patents
Chloromethylphosphinic acid, salts thereof, and method of preparationInfo
- Publication number
- GB934090A GB934090A GB3791061A GB3791061A GB934090A GB 934090 A GB934090 A GB 934090A GB 3791061 A GB3791061 A GB 3791061A GB 3791061 A GB3791061 A GB 3791061A GB 934090 A GB934090 A GB 934090A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- salts
- chlormethyl
- dichloride
- ammonium
- 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
- AOASVTBKGBXGTN-UHFFFAOYSA-N OP(=O)CCl Chemical compound OP(=O)CCl AOASVTBKGBXGTN-UHFFFAOYSA-N 0.000 title abstract 6
- 150000003839 salts Chemical class 0.000 title abstract 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 150000001340 alkali metals Chemical group 0.000 abstract 2
- 150000003863 ammonium salts Chemical class 0.000 abstract 2
- 239000007864 aqueous solution Substances 0.000 abstract 2
- JLUMKVGIQTWWKK-UHFFFAOYSA-N dichloro(chloromethyl)phosphane Chemical compound ClCP(Cl)Cl JLUMKVGIQTWWKK-UHFFFAOYSA-N 0.000 abstract 2
- 229910001447 ferric ion Inorganic materials 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 239000011541 reaction mixture Substances 0.000 abstract 2
- 238000010992 reflux Methods 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 abstract 1
- 229910006124 SOCl2 Inorganic materials 0.000 abstract 1
- DYAHQFWOVKZOOW-UHFFFAOYSA-N Sarin Chemical compound CC(C)OP(C)(F)=O DYAHQFWOVKZOOW-UHFFFAOYSA-N 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 239000000908 ammonium hydroxide Substances 0.000 abstract 1
- 239000003963 antioxidant agent Substances 0.000 abstract 1
- 230000003078 antioxidant effect Effects 0.000 abstract 1
- 239000002738 chelating agent Substances 0.000 abstract 1
- MOFCYHDQWIZKMY-UHFFFAOYSA-N chloromethylphosphonic acid Chemical compound OP(O)(=O)CCl MOFCYHDQWIZKMY-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- IMDXZWRLUZPMDH-UHFFFAOYSA-N dichlorophenylphosphine Chemical compound ClP(Cl)C1=CC=CC=C1 IMDXZWRLUZPMDH-UHFFFAOYSA-N 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 150000007529 inorganic bases Chemical class 0.000 abstract 1
- 229960002523 mercuric chloride Drugs 0.000 abstract 1
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- BCDIWLCKOCHCIH-UHFFFAOYSA-N methylphosphinic acid Chemical class CP(O)=O BCDIWLCKOCHCIH-UHFFFAOYSA-N 0.000 abstract 1
- SCLFRABIDYGTAZ-UHFFFAOYSA-N methylphosphonic acid dichloride Chemical compound CP(Cl)(Cl)=O SCLFRABIDYGTAZ-UHFFFAOYSA-N 0.000 abstract 1
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical compound CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 239000003209 petroleum derivative Substances 0.000 abstract 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000003381 stabilizer Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/26—Organic compounds containing phosphorus
- C10L1/2608—Organic compounds containing phosphorus containing a phosphorus-carbon bond
-
- 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
- C07F9/48—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof
- C07F9/4808—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof the acid moiety containing a substituent or structure which is considered as characteristic
- C07F9/4816—Acyclic saturated acids or derivatices which can have 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
- C07F9/50—Organo-phosphines
- C07F9/52—Halophosphines
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)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
Abstract
The invention comprises chlormethyl phosphinic acid and its salts of the general formula ClCH2.P(O)(H)(OY) wherein Y is a hydrogen atom, an alkali metal atom, e.g. sodium, or an ammonium radical. Chlormethylphosphinic acid may be prepared by the hydrolysis of chlormethylphosphonous dichloride ClCH2PCl2 in neutral to acidic aqueous solution, the reaction being preferably carried out in a non-oxidising atmosphere, e.g. of nitrogen. It is preferred to use at least two moles of water for each mole of the dichloride and to use water containing hydrochloric acid as the hydrolysing medium. Preferred reaction temperatures are between 20 DEG and 40 DEG C. and any excess water and the hydrochloric acid formed may be removed from the reaction mixture by volatilisation at about 40 DEG C. and a pressure of 1 to 2 mm. Hg. The acid may be neutralised with various inorganic bases to form the salts, e.g. the acid may be dissolved in ethanol and neutralised with a strong sodium hydroxide solution to form the sodium salt. Under strongly alkaline conditions the chlormethyl phosphonic acid may be hydrolysed to the metal salts of methyl phosphinic acid which may be chlorinated with SOCl2 to form methyl phosphonic dichloride which may then be reacted with methylphosphonic difluoride and isopropyl alcohol to form an isopropyl methylphosphonofluoridate. Chlormethyl phosphinic acid reacts with an excess of ammonium hydroxide under reflux conditions to yield the ammonium salt of amidomethyl phosphinic acid and on treating the reaction mixture with an excess of sodium hydroxide and 2 molecular proportions of chlormethylphosphinic acid and then acidifying with HCl a trismethylenephosphinic acid amine product N[CH2P(O)(H)(OH)]3 is obtained which is an effective chelating agent for ferric ions in aqueous solution at pH 9,0 to 11,0. The latter compound may be oxidised with air in the presence of mercuric chloride to yield the corresponding phosphonic acid which has a greatly enhanced chelating power for ferric ions. The chlormethyl phosphinic acid and its alkali metal and ammonium salts are stated to be useful as antioxidant stabilizers for petroleum products. Chlormethylphosphonous dichloride is obtained by reacting ClCH2P(S)Cl2 with C6H5PCl2. Reaction may be effected under reflux in an atmosphere of nitrogen at 165-175 DEG C.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6501860A | 1960-10-26 | 1960-10-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB934090A true GB934090A (en) | 1963-08-14 |
Family
ID=22059796
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3791061A Expired GB934090A (en) | 1960-10-26 | 1961-10-23 | Chloromethylphosphinic acid, salts thereof, and method of preparation |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB934090A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3366678A (en) * | 1963-08-21 | 1968-01-30 | Armour & Co | Para xylylene bis(phosphonous acid) bis (anilino) compounds useful as anti-bacterialagents |
| US3394083A (en) * | 1963-08-15 | 1968-07-23 | Monsanto Co | Effervescent builder compositions and detergent compositions containing the same |
| US3432547A (en) * | 1963-08-21 | 1969-03-11 | Armour & Co | Bis-aminophosphinic acids useful as anti-bacterial agents |
| US3816518A (en) * | 1970-04-13 | 1974-06-11 | Monsanto Co | Preparation of ethane diphosphonic acids substituted with both amine and hydroxy groups |
-
1961
- 1961-10-23 GB GB3791061A patent/GB934090A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3394083A (en) * | 1963-08-15 | 1968-07-23 | Monsanto Co | Effervescent builder compositions and detergent compositions containing the same |
| US3366678A (en) * | 1963-08-21 | 1968-01-30 | Armour & Co | Para xylylene bis(phosphonous acid) bis (anilino) compounds useful as anti-bacterialagents |
| US3432547A (en) * | 1963-08-21 | 1969-03-11 | Armour & Co | Bis-aminophosphinic acids useful as anti-bacterial agents |
| US3816518A (en) * | 1970-04-13 | 1974-06-11 | Monsanto Co | Preparation of ethane diphosphonic acids substituted with both amine and hydroxy groups |
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