GB1012796A - Substituted aminophosphonium compounds - Google Patents
Substituted aminophosphonium compoundsInfo
- Publication number
- GB1012796A GB1012796A GB2354762A GB2354762A GB1012796A GB 1012796 A GB1012796 A GB 1012796A GB 2354762 A GB2354762 A GB 2354762A GB 2354762 A GB2354762 A GB 2354762A GB 1012796 A GB1012796 A GB 1012796A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- alkylene
- anion
- hydrogen
- picrate
- 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
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 System
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids R2P(=O)(OH); Thiophosphinic acids, i.e. R2P(=X)(XH) (X = S, Se)
- C07F9/36—Amides 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 System
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5463—Compounds of the type "quasi-phosphonium", e.g. (C)a-P-(Y)b wherein a+b=4, b>=1 and Y=heteroatom, generally N or O
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
- C10M2223/061—Metal salts
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/04—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having a silicon-to-carbon bond, e.g. organo-silanes
Abstract
Petrol and lubricating oils contain as additives useful as lead scavengers and antioxidants aminophosphonium compounds of the general formula <FORM:1012796/C4-C5/1> wherein n is 1 or 2, R1 and R11 are the same or different and are hydrogen, alkyl, alkenyl, aryl, alkylaryl or cycloalkyl (provided that R1 and R11 are not both hydrogen) or R1 and R11 taken together represent alkylene or a dialkylene ether radical, R111 is alkyl, alkanyl, phenyl, halophenyl, alkylphenyl or halophenyl alkyl, R when n is 1 is alkyl, phenylalkyl, diphenyl alkyl, or mono- or di-halogenated phenylalkyl, phenyldiazonium or halotriazinyl, or when n is 2 R is alkylene, alkenylene, alkylene-aralkylene, alkylenetetraalkyldisiloxanyl alkylene or a dialkylene ether radical and A- is an anion, provided that where A- is iodine and n is 1 not more than three of R1, R11, R111 and R are methyl (see Division C2). The anion A-may be Cl, Br, I, F, borohydride, picrate or hexafluorophosphate.ALSO:The invention comprises inter alia substituted amino phosphonium compounds of the general formula <FORM:1012796/C3/1> wherein n is 2, R1 and R11 are the same or different and are hydrogen, alkyl, alkenyl, aryl, alkylaryl or cycloalkyl (provided that R1 and R11 are not both hydrogen) or R1 and R11 taken together represent alkylene or a dialkylene ether radical, R111 is alkyl, alkenyl, phenyl, halophenyl, alkylphenyl, or halophenylalkyl, R is alkylenetetralkyl disiloxanylalkylene, and A- is an anion, e.g. Cl, Br, I, F, borohydride, picrate or hexafluorophosphate. The products wherein A is halogen may be obtained by reacting an organic halide RXn with an aminophosphine of the formula <FORM:1012796/C3/2> wherein X is halogen and the other symbols are as defined above. The reaction is preferably carried out in the presence of an inert solvent, e.g. dimethylformamide, benzene, toluene, xylene or diethyl ether and preferred reaction temperatures are from 35 DEG to 200 DEG C. The halide anion X may be replaced by other anions such as borohydride, picrate or hexafluorophosphate by adding a solution of the aminophosphonium halide to a saturated solution of a salt containing the desired anion. An example is given for the production of the compound of the formula <FORM:1012796/C3/3> The products are useful as lead scavengers and antioxidants for petrol and lubricating oils and as plant growth retardants, nematocides, and intermediates for polymers.ALSO:The invention comprises substituted amino-phosphonium compounds of the general formula:- <FORM:1012796/C2/1> wherein n is 1 or 2, R1 and R11 are the same or different and are hydrogen, alkyl, alkenyl, aryl, alkylaryl or cycloalkyl (provided that R1 and R11 are not both hydrogen) or R1 and R11 taken together represent alkylene or a dialkylene ether radical, R111 is alkyl, alkenyl, phenyl, halophenyl, alkylphenyl or halophenyl-alkyl; R, where n is 1, is alkyl, phenylalkyl, diphenylalkyl, mono- or di-halophenylalkyl, phenyl-diazonium or halotriazinyl, or where n is 2 R is alkylene, alkenylene, alkylene - aralkylene, alkylenetetraalkyldisiloxanylalkylene or a dialkylene ether radical and A- is an anion provided that when A- is iodine and n is 1 not more than three of R1, R11, R111 and R are methyl. The anion A- may be Cl, Br, I, F, borohydride, picrate or hexafluorophosphate. Preferred compounds are those in which R1 is hydrogen or an alkyl radical of up to 4 C atoms, R11 is an alkyl group of up to 4 C atoms, especially t.-butyl, R111 is phenyl and when n is 1 R is alkyl of up to 4 C atoms, benzyl, halobenzyl, or halotriazinyl or when n is 2, R is alkylene or alkenylene of up to 4 carbon atoms, xylylene, alkyl-substituted xylylene (e.g. tetramethyl-p-xylylene), di-alkylene ether having alkylene substituents of 2 to 4 carbon atoms, 9,10-anthracenylene-dimethylene or alkylene-tetraalkyldisiloxanyl alkylene wherein the alkyl and alkylene groups have 1 to 4 carbon atoms. The products wherein A- is halogen may be obtained by reacting an organic halide RXn with an aminophosphine of the formula <FORM:1012796/C2/2> wherein X is halogen and the other symbols are as defined above. The reaction is preferably carried out in the presence of an inert solvent, e.g. dimethylformamide, benzene, toluene, xylene or diethyl ether, and preferred reaction temperatures are from 35 DEG to 200 DEG C. The halide anion X may be replaced by other anions such as borohydride, picrate or hexafluorophosphate by adding a solution of the amino-phosphonium halide to a saturated solution of a salt containing the desired anion. Several examples are given and the products are useful as lead scavengers and antioxidants for petrol and lubricating oils and as plant growth retardants, nematocides and intermediates for polymers.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11875961A | 1961-06-22 | 1961-06-22 | |
US172088A US3131204A (en) | 1962-02-09 | 1962-02-09 | Novel diquaternary aminophosphonium compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1012796A true GB1012796A (en) | 1965-12-08 |
Family
ID=26816717
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2354762A Expired GB1012796A (en) | 1961-06-22 | 1962-06-19 | Substituted aminophosphonium compounds |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB1012796A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1956026A1 (en) * | 2005-12-02 | 2008-08-13 | Kanto Denka Kogyo CO., LTD. | Ionic liquid containing phosphonium cation having p-n bond and method for producing same |
WO2012113889A1 (en) * | 2011-02-23 | 2012-08-30 | University College Dublin | Processes for the stereoselective preparation of p-chiral four -coordinated phosphorus borane compounds and p-chiral three-coordinated phosphorus compounds |
-
1962
- 1962-06-19 GB GB2354762A patent/GB1012796A/en not_active Expired
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1956026A1 (en) * | 2005-12-02 | 2008-08-13 | Kanto Denka Kogyo CO., LTD. | Ionic liquid containing phosphonium cation having p-n bond and method for producing same |
EP1956026A4 (en) * | 2005-12-02 | 2009-02-25 | Kanto Denka Kogyo Kk | Ionic liquid containing phosphonium cation having p-n bond and method for producing same |
JP5265197B2 (en) * | 2005-12-02 | 2013-08-14 | 関東電化工業株式会社 | Ionic liquid having phosphonium cation containing PN bond and method for producing the same |
US8871974B2 (en) | 2005-12-02 | 2014-10-28 | Kanto Denka Kogyo Co., Ltd. | Ionic liquid containing phosphonium cation having P—N bond and method for producing same |
WO2012113889A1 (en) * | 2011-02-23 | 2012-08-30 | University College Dublin | Processes for the stereoselective preparation of p-chiral four -coordinated phosphorus borane compounds and p-chiral three-coordinated phosphorus compounds |
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