GB801523A - New phosphoric and acid thionophosphoric acid esters and a process for their production - Google Patents
New phosphoric and acid thionophosphoric acid esters and a process for their productionInfo
- Publication number
- GB801523A GB801523A GB23192/55A GB2319255A GB801523A GB 801523 A GB801523 A GB 801523A GB 23192/55 A GB23192/55 A GB 23192/55A GB 2319255 A GB2319255 A GB 2319255A GB 801523 A GB801523 A GB 801523A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oximide
- diethyl
- acid
- thionophosphate
- reacting
- 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
- 239000002253 acid Substances 0.000 title abstract 4
- 150000002148 esters Chemical class 0.000 title abstract 2
- MEVHTHLQPUQANE-UHFFFAOYSA-N aziridine-2,3-dione Chemical compound O=C1NC1=O MEVHTHLQPUQANE-UHFFFAOYSA-N 0.000 abstract 18
- -1 alkyl radicals Chemical class 0.000 abstract 7
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 abstract 6
- 125000004122 cyclic group Chemical group 0.000 abstract 4
- 229910052760 oxygen Inorganic materials 0.000 abstract 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 abstract 2
- XSCRWBSKSVOZOK-UHFFFAOYSA-N 2,3-dichlorobutanedioic acid Chemical compound OC(=O)C(Cl)C(Cl)C(O)=O XSCRWBSKSVOZOK-UHFFFAOYSA-N 0.000 abstract 1
- VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 abstract 1
- 241001465754 Metazoa Species 0.000 abstract 1
- 229910019142 PO4 Inorganic materials 0.000 abstract 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 abstract 1
- 150000008041 alkali metal carbonates Chemical class 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract 1
- HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 230000000361 pesticidal effect Effects 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 1
- 239000010452 phosphate Substances 0.000 abstract 1
- 125000001557 phthalyl group Chemical group C(=O)(O)C1=C(C(=O)*)C=CC=C1 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000001384 succinic acid Substances 0.000 abstract 1
- 231100000331 toxic Toxicity 0.000 abstract 1
- 230000002588 toxic effect Effects 0.000 abstract 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/5537—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom the heteroring containing the structure -C(=O)-N-C(=O)- (both carbon atoms belong to the heteroring)
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)
Abstract
The invention comprises phosphoric and thionophosphoric acid esters of the general formula: <FORM:0801523/IV (b)/1> in which: <FORM:0801523/IV (b)/2> represents the residue of a cyclic dicarboxylic acid oximide, X is an oxygen or sulphur atom and R1 and R2 are alkyl radicals containing no more than 4 carbon atoms. They may be obtained by reacting a cyclic dicarboxylic acid oximide with a dialkyl phosphoric or thiophosphoric acid monohalide in the presence of an acid binding agent, e.g. an alkali metal carbonate or tertiary base or by reacting an alkali metal salt of a cyclic dicarboxylic acid oximide in the presence of a solvent with a dialkyl phosphoric or thiophosphoric acid monohalide. Specified solvents are methyl ethyl ketone, acetone and dimethyl formamide. Suitable reaction temperatures are between 0 DEG and 150 DEG C., e.g. between 20 DEG and 70 DEG C. Examples are given for the production of O,O-dimethyl-, O-O-diethyl-, ethyl n-propyl-, ethyl-isopropyl-and ethyl n-butyl-, phthalyl oximide thionophosphates; O,O-diethyl tetrachlorophthalyl oximide thionophosphate; O,O-diethyl phthalyl oximide phosphate; O,O-diethyl-D 4-tetrahydrophthalyl oximide thionophosphate; O,O-diethyl hexahydrophthalyl oximide thionophosphate; O,O - diethyl hexahydrophthalyl oximide thionophosphate; O,O - diethyl - 3,6-endomethylene - D 4 - tetrahydrophthalyl oximide thionophosphate; O,O - diethyl - 3,6-endomethylene - hexahydrophthalyl oximide thionophosphate; 1,2,3,4 - tetrahydronaphthalene - 1,4 - endo - oxy ethylene - 2,3 - dicarboxylic acid oximide thionophosphoric acid diethyl ester; O,O-diethyl naphthalic acid oximide thionophosphate and O,O-diethyl succinic acid oximide thionophosphate. Other cyclic oximide starting materials specified are dichlorophthalyl oximide; D 4-tetrahydronaphthyl oximide, and dichlorosuccinic acid oximide. The products are stated to have a low toxic effect against warm-blooded animals and to have pesticidal properties. Phthalyl oximide may be obtained by reacting hydroxylamine with phthalic anhydride and 1,2,3,4-tetrahydronaphthalene - 1,4 - endo - oxyethylene - 2,3-dicarboxylic acid oximide may be obtained by reacting b -naphthol and maleic anhydride to form 1,2,3,4 - tetrahydronaphthalene - 1,4-endo-oxyethylene-2,3-carboxylic acid anhydride which is then reacted with hydroxylamine to yield the oximide.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE336397X | 1954-08-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB801523A true GB801523A (en) | 1958-09-17 |
Family
ID=6220316
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB23192/55A Expired GB801523A (en) | 1954-08-16 | 1955-08-11 | New phosphoric and acid thionophosphoric acid esters and a process for their production |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH336397A (en) |
| FR (1) | FR1129793A (en) |
| GB (1) | GB801523A (en) |
| NL (2) | NL91287C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016042040A1 (en) * | 2014-09-18 | 2016-03-24 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Use of phosphorous-containing organic oxyimides as flame retardants and/or as stabilizers for plastics, flame-retardant and/or stabilized plastic compositions, method for the production thereof, moulded part, paint and coatings |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3122560A (en) * | 1962-06-20 | 1964-02-25 | Dow Chemical Co | N-hydroxydicarboximides |
| US3228960A (en) * | 1962-06-20 | 1966-01-11 | Dow Chemical Co | 7-oxabicyclo-(2.2.1) heptane-2, 3-dicarboximido and 7-oxabicyclo (2.2.1) hept-5-ene-2, 3-dicarboximido phosphates |
| US3268554A (en) * | 1964-12-17 | 1966-08-23 | Rexall Drug Chemical | Substituted endo-perhydro-4, 7-methanoisoindoles and intermediates therein |
| US4042691A (en) * | 1973-12-05 | 1977-08-16 | Basf Aktiengesellschaft | Succinic acid oximidophosphoric ester insecticides |
| DE2360493A1 (en) * | 1973-12-05 | 1975-06-12 | Basf Ag | AMBER ACID OXIMIDE PHOSPHORIC ACID ESTER |
-
0
- NL NL205909D patent/NL205909A/xx unknown
- NL NL91287D patent/NL91287C/xx active
-
1955
- 1955-07-14 CH CH336397D patent/CH336397A/en unknown
- 1955-08-11 GB GB23192/55A patent/GB801523A/en not_active Expired
- 1955-08-16 FR FR1129793D patent/FR1129793A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016042040A1 (en) * | 2014-09-18 | 2016-03-24 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Use of phosphorous-containing organic oxyimides as flame retardants and/or as stabilizers for plastics, flame-retardant and/or stabilized plastic compositions, method for the production thereof, moulded part, paint and coatings |
| CN107001698A (en) * | 2014-09-18 | 2017-08-01 | 弗劳恩霍弗应用研究促进协会 | Phosphorous organic epoxide acid imide is used as flame retardant of plastic agent and/or the purposes of stabilizer, fire-retardant and/or stable plastics composite, its preparation method, molded item, paint and coating |
| US10544284B2 (en) | 2014-09-18 | 2020-01-28 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Use of phosphorous-containing organic oxyimides as flame retardants and/or as stabilizers for plastics, flame-retardant and/or stabilized plastic compositions, method for the production thereof, moulded part, paint and coatings |
Also Published As
| Publication number | Publication date |
|---|---|
| NL91287C (en) | |
| CH336397A (en) | 1959-02-28 |
| NL205909A (en) | |
| FR1129793A (en) | 1957-01-25 |
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