SU116882A1 - Method for producing dialkyl esters of vinylphosphonic acid and substituted diamides - Google Patents
Method for producing dialkyl esters of vinylphosphonic acid and substituted diamidesInfo
- Publication number
- SU116882A1 SU116882A1 SU593761A SU593761A SU116882A1 SU 116882 A1 SU116882 A1 SU 116882A1 SU 593761 A SU593761 A SU 593761A SU 593761 A SU593761 A SU 593761A SU 116882 A1 SU116882 A1 SU 116882A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- vinylphosphonic acid
- dialkyl esters
- producing dialkyl
- diamides
- substituted
- Prior art date
Links
- 150000001470 diamides Chemical class 0.000 title description 5
- 150000002148 esters Chemical class 0.000 title description 4
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- MLSZIADXWDYFKM-UHFFFAOYSA-N 1-dichlorophosphorylethene Chemical compound ClP(Cl)(=O)C=C MLSZIADXWDYFKM-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 3
- 229910001626 barium chloride Inorganic materials 0.000 description 3
- 239000008262 pumice Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- MQIGTIFMSSGUBS-UHFFFAOYSA-N ethenylphosphinic acid Chemical compound OP(=O)C=C MQIGTIFMSSGUBS-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- LOUZURPQCYZSJH-UHFFFAOYSA-N 1-chloro-2-dichlorophosphorylethane Chemical compound ClCCP(Cl)(Cl)=O LOUZURPQCYZSJH-UHFFFAOYSA-N 0.000 description 1
- RLEDXRUOCJHVLB-UHFFFAOYSA-N ClP(=O)C=C Chemical compound ClP(=O)C=C RLEDXRUOCJHVLB-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- ZOSLXSXTWULQTE-UHFFFAOYSA-N ethenyl(ethoxy)phosphinic acid Chemical compound CCOP(O)(=O)C=C ZOSLXSXTWULQTE-UHFFFAOYSA-N 0.000 description 1
- XHDNNRGTROLZCF-UHFFFAOYSA-N ethenyl(methoxy)phosphinic acid Chemical compound COP(O)(=O)C=C XHDNNRGTROLZCF-UHFFFAOYSA-N 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- BCDIWLCKOCHCIH-UHFFFAOYSA-N methylphosphinic acid Chemical compound CP(O)=O BCDIWLCKOCHCIH-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
Description
Предлагаемое изобретение позвол ет получать диалкиловые эфиры ВИНИЛФОСФИНОВОЙ кислоты и ее замещенные диамиды, могущие найти применение в приготовлении пластических масс, инсектицидов и других практически важных продуктов.The present invention allows to obtain dialkyl esters of VINYLPHOSPHINOIC acid and its substituted diamides, which can be used in the preparation of plastics, insecticides and other practically important products.
Осуществление способа достигаетс дегидрохлорированием хлорангидрида р-хлорэтилфосфиновой кислоты над хлористым барием, нанесенным на пемзу, при 330-340° в хлорангидрид винилфосфиновой кислоты , который затем подвергают действию спирта в присутствии третичных аминов. Дл получени замещенных диамидов на хлорангидрид вииилфосфиновой кислоты действуют вторичным амином.The process is accomplished by dehydrochlorinating p-chloroethylphosphonic acid chloride over barium chloride deposited on pumice at 330-340 ° in vinylphosphinic acid chloride, which is then exposed to alcohol in the presence of tertiary amines. To obtain substituted diamides, viiylphosphinic acid chloride acts as a secondary amine.
Пример 1. Получение хлорангидрида винилфосфиновой кислоты.Example 1. Obtaining the acid chloride vinylphosphonic acid.
Хлорангидрид р-хлорэтилфосфиновой кислоты по капл м пропускают через трубку, наполненную безводным хлористым барием, нанесенным на пемзу, и нагретую до 330-340° при одновременном пропугскании слабого тока азота. После фракционированной разгонки продуктов релкции получают хлорангидрид винилфосфиновой кислоты свыходом 70% теоретического. Т. кип. 67-69° при 21 мм рт. ст.; - 1,4808;The p-chloroethylphosphinic acid chloride dropwise is passed through a tube filled with anhydrous barium chloride deposited on pumice stone and heated to 330-340 ° while simultaneously fading a weak stream of nitrogen. After fractionated distillation of the products of the reaction, vinylphosphonic acid chloride is obtained with a yield of 70% of the theoretical. T. Kip. 67-69 ° with 21 mm Hg. v .; - 1.4808;
d42° - 1,4092.d42 ° - 1.4092.
Пример 2. Получение метилового эфира винилфосфиновой кислоты .Example 2. Obtaining methyl ester of vinylphosphinic acid.
1 моль хлорангидрида винилфосфиновой кислоты добавл ют постепенно к раствору 2 молей метанола и 2 молей триэтиламина в эфире, бензоле или другом растворителе при перемешивании и температуре минус 5-0°, и оставл ют на несколько часов при комнатной температуре. Выпавший осадок отфильтровывают, а фильтрат сначала освобождают от растворител путем отгонки, затем остаток фракционируют. Получают метиловый эфир винилфосфиновой кислоты с выходом 45-55% теоретического. Т. кип. 72-73° при 10 мм рт. ст.; п - 1,4330;1 mol of vinylphosphonic acid chloride is gradually added to a solution of 2 moles of methanol and 2 moles of triethylamine in ether, benzene or another solvent with stirring and at a temperature of minus 5-0, and left for several hours at room temperature. The precipitate formed is filtered off and the filtrate is first freed from the solvent by distillation, then the residue is fractionated. Vinylphosphonic acid methyl ester is obtained with a yield of 45-55% of the theoretical. T. Kip. 72-73 ° with 10 mm Hg. v .; p - 1.4330;
d42o - 1,1405.d42o - 1.1405.
№ 116882- 2 -No. 116882-2 -
Таким же путем получен этиловый эфир винилфосфиновой кислоты с выходом 45-50% теоретического. Т. кип. 62° при 3 мм рт. ст.; п -In the same way, vinylphosphonic acid ethyl ester was obtained with a yield of 45-50% of the theoretical. T. Kip. 62 ° at 3 mm Hg. v .; P -
1,4338; d42° - 1,0550.1.4338; d42 ° - 1.0550.
П р и м е р 3. Ползчение ди(дидМетиламино) амида метилфосфиновой кислоты.PRI me R 3. The creep of di (didmetilamino) amide methylphosphinic acid.
К 1 молю хлорангидрида винилфосфиновой кислоты в растворе бензола или эфира добавл ют постепенно 4 мол диметиламина при температуре минус 5-0° при перемешивании. После отделени осадка и отгонки растворител остаток фракционируют. Получают диамид с выходом 50-55% теоретического. Т. кип. 82 при 3 мм рт. ст.; п -To 1 mol of vinylphosphonic acid chloride in a solution of benzene or ether, 4 moles of dimethylamine are gradually added at a temperature of minus 5-0 with stirring. After separating the precipitate and distilling off the solvent, the residue is fractionated. Diamide is obtained with a yield of 50-55% of the theoretical. T. Kip. 82 at 3 mmHg. v .; P -
1,4732; d42° - 1,0257.1.4732; d42 ° - 1.0257.
Предмет изобретени Subject invention
Способ получени диалкиловых эфиров винилфосфиновой кислоты и; замещенных диамидов, о тл и ч а ю щи и с/ .тем, что хлоран1гидрид хлорэтилфосфиновой кислоты дегидрохлорируют пропусканием над хлористым барием, нанесенным на пемзу, при 330-340°, в хлорангидрид винилфосфиновой кислоты, последний ввод т во взаимодействие со спиртами дл получени диалкиловых эфиров или с вторичными аминами дл получени замещенных диамидов.A process for the preparation of vinylphosphonic acid dialkyl esters and; substituted diamides, oh t and h and y with. The fact that chloroethylphosphonic acid chloride is dehydrochlorinated by passing over barium chloride deposited on pumice at 330–340 °, into vinylphosphonic acid chloride, the latter is reacted with alcohols to obtain dialkyl esters or with secondary amines to produce substituted diamides.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU593761A SU116882A1 (en) | 1958-03-01 | 1958-03-01 | Method for producing dialkyl esters of vinylphosphonic acid and substituted diamides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU593761A SU116882A1 (en) | 1958-03-01 | 1958-03-01 | Method for producing dialkyl esters of vinylphosphonic acid and substituted diamides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU116882A1 true SU116882A1 (en) | 1958-11-30 |
Family
ID=48389075
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU593761A SU116882A1 (en) | 1958-03-01 | 1958-03-01 | Method for producing dialkyl esters of vinylphosphonic acid and substituted diamides |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU116882A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1138770B (en) * | 1959-06-20 | 1962-10-31 | Hoechst Ag | Process for the production of unsaturated phosphonic acid dichlorides |
| DE1158509B (en) * | 1958-12-27 | 1963-12-05 | Bayer Ag | Process for the production of vinylphosphonic acid or vinylthionophosphonic acid dichloride |
-
1958
- 1958-03-01 SU SU593761A patent/SU116882A1/en active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1158509B (en) * | 1958-12-27 | 1963-12-05 | Bayer Ag | Process for the production of vinylphosphonic acid or vinylthionophosphonic acid dichloride |
| DE1138770B (en) * | 1959-06-20 | 1962-10-31 | Hoechst Ag | Process for the production of unsaturated phosphonic acid dichlorides |
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