GB1121462A - Synthesis of phosphinic and thiophosphinic esters - Google Patents
Synthesis of phosphinic and thiophosphinic estersInfo
- Publication number
- GB1121462A GB1121462A GB32271/65A GB3227165A GB1121462A GB 1121462 A GB1121462 A GB 1121462A GB 32271/65 A GB32271/65 A GB 32271/65A GB 3227165 A GB3227165 A GB 3227165A GB 1121462 A GB1121462 A GB 1121462A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phosphorochloridate
- alkoxyaryl
- alkaryl
- aryl
- alkyl
- 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
- 150000002148 esters Chemical class 0.000 title abstract 2
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 125000004171 alkoxy aryl group Chemical group 0.000 abstract 4
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000003118 aryl group Chemical group 0.000 abstract 4
- 125000005325 aryloxy aryl group Chemical group 0.000 abstract 4
- ITVPBBDAZKBMRP-UHFFFAOYSA-N chloro-dioxido-oxo-$l^{5}-phosphane;hydron Chemical compound OP(O)(Cl)=O ITVPBBDAZKBMRP-UHFFFAOYSA-N 0.000 abstract 4
- 150000002902 organometallic compounds Chemical class 0.000 abstract 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 3
- 239000012530 fluid Substances 0.000 abstract 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 239000005864 Sulphur Substances 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- -1 aliphatic ethers Chemical class 0.000 abstract 2
- 239000004411 aluminium Chemical group 0.000 abstract 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 2
- 229910052782 aluminium Inorganic materials 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 229910052744 lithium Chemical group 0.000 abstract 2
- 239000011777 magnesium Chemical group 0.000 abstract 2
- 229910052749 magnesium Inorganic materials 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- 239000011734 sodium Substances 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 150000004292 cyclic ethers Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 230000002363 herbicidal effect Effects 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 230000000749 insecticidal effect Effects 0.000 abstract 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
- C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
-
- 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
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
-
- 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
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/015—Dispersions of solid lubricants
- C10N2050/02—Dispersions of solid lubricants dissolved or suspended in a carrier which subsequently evaporates to leave a lubricant coating
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Semi-solids; greasy
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)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Phosphinic acid esters, obtainable by reacting a phosphorochloridate of the formula <FORM:1121462/C4-C5/1> where R1 is an alkyl, aryl, alkaryl, alkoxyaryl or aryloxyaryl group, Y and Z are each oxygen or sulphur, m and n are each 1 or 2 and m + n = 3, with at least one organometallic compound of the formula (R2)xM(X)y where R2 is an alkyl, aryl, alkaryl, alkoxyaryl or aryloxyaryl group, M is sodium, magnesium, aluminium or lithium, X is halogen, x is 1, 2 or 3, y is 0, 1 or 2 and the sum of x and y is the valency of M (see Division C2), are stated to be useful as functional fluids, particularly hydraulic fluids.ALSO:Phosphinic or thiophosphinic acid esters are obtained by reacting a phosphorochloridate of the formula <FORM:1121462/C2/1> wherein R1 is an alkyl, aryl, alkaryl, alkoxyaryl or aryloxyaryl group, Y and Z are each oxygen or sulphur, m and n are each 1 or 2 and m + n = 3, with at least one organometallic compound of the formula (R2)xM(X)y where R2 is an alkyl, aryl, alkaryl, alkoxyaryl or aryloxyaryl group, M is sodium, magnesium, aluminium or lithium, X is a halogen atom, x is 1, 2 or 3, y is 0, 1 or 2 and the sum of x and y is the valency of M, by adding a solution of the said organometallic compound to the said phosphorochloridate. The solution of the organometallic compound is preferably added dropwise to the phosphorochloridate at reflux temperature, and preferred solvents are aliphatic ethers such as diethyl ether, cyclic ethers such as tetrahydrofuran, and inert hydrocarbons. The products have herbicidal, insecticidal and biocidal properties and are also useful as functional fluids.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38607764A | 1964-07-29 | 1964-07-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1121462A true GB1121462A (en) | 1968-07-31 |
Family
ID=23524061
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB32271/65A Expired GB1121462A (en) | 1964-07-29 | 1965-07-28 | Synthesis of phosphinic and thiophosphinic esters |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1252680B (en) |
| GB (1) | GB1121462A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015025904A1 (en) * | 2013-08-22 | 2015-02-26 | 株式会社Adeka | Phosphorus-containing compound, and curable epoxy resin composition containing same |
| WO2016121750A1 (en) * | 2015-01-29 | 2016-08-04 | 株式会社Adeka | Flame-retardant epoxy resin composition, prepreg formed using this, and laminate plate |
-
0
- DE DENDAT1252680D patent/DE1252680B/en active Pending
-
1965
- 1965-07-28 GB GB32271/65A patent/GB1121462A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015025904A1 (en) * | 2013-08-22 | 2015-02-26 | 株式会社Adeka | Phosphorus-containing compound, and curable epoxy resin composition containing same |
| CN105452263A (en) * | 2013-08-22 | 2016-03-30 | 株式会社艾迪科 | Phosphorus-containing compound, and curable epoxy resin composition containing same |
| JPWO2015025904A1 (en) * | 2013-08-22 | 2017-04-27 | 株式会社Adeka | Phosphorus-containing compound and curable epoxy resin composition containing the same |
| US10562924B2 (en) | 2013-08-22 | 2020-02-18 | Adeka Corporation | Phosphorus-containing compound, and curable epoxy resin composition containing same |
| WO2016121750A1 (en) * | 2015-01-29 | 2016-08-04 | 株式会社Adeka | Flame-retardant epoxy resin composition, prepreg formed using this, and laminate plate |
| US10421261B2 (en) | 2015-01-29 | 2019-09-24 | Adeka Corporation | Flame-retardant epoxy resin composition, prepreg and laminated plate using the same |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1252680B (en) | 1967-10-26 |
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