SU319604A1 - METHOD OF OBTAINING FUNCTIONAL SUBSTITUTE DIALKYLPHOSPHATES - Google Patents
METHOD OF OBTAINING FUNCTIONAL SUBSTITUTE DIALKYLPHOSPHATESInfo
- Publication number
- SU319604A1 SU319604A1 SU1347815A SU1347815A SU319604A1 SU 319604 A1 SU319604 A1 SU 319604A1 SU 1347815 A SU1347815 A SU 1347815A SU 1347815 A SU1347815 A SU 1347815A SU 319604 A1 SU319604 A1 SU 319604A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- dialkylphosphates
- obtaining functional
- functional substitute
- dialkyl phosphates
- carbon tetrachloride
- Prior art date
Links
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 10
- 235000021317 phosphate Nutrition 0.000 claims description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 8
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 7
- GQZXNSPRSGFJLY-UHFFFAOYSA-N Hypophosphorous acid Chemical compound OP=O GQZXNSPRSGFJLY-UHFFFAOYSA-N 0.000 claims description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims 1
- 239000001913 cellulose Substances 0.000 description 5
- XHXFXVLFKHQFAL-UHFFFAOYSA-N Phosphoryl chloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 235000010980 cellulose Nutrition 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 229920005610 lignin Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K [O-]P([O-])([O-])=O Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- FKNYTRBBGNUNOX-UHFFFAOYSA-N N,N-diethyl-2-(4-methylphenoxy)ethanamine Chemical compound CCN(CC)CCOC1=CC=C(C)C=C1 FKNYTRBBGNUNOX-UHFFFAOYSA-N 0.000 description 1
- FXZWPZMCZNJILD-UHFFFAOYSA-N N-[(6-bromopyridin-3-yl)methyl]ethanamine;hydrochloride Chemical compound Cl.CCNCC1=CC=C(Br)N=C1 FXZWPZMCZNJILD-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N Tetrahydro-2-furanmethanol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- -1 for example Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- UICJTXWOLHIBBO-UHFFFAOYSA-L oxolan-2-ylmethyl phosphate Chemical compound [O-]P([O-])(=O)OCC1CCCO1 UICJTXWOLHIBBO-UHFFFAOYSA-L 0.000 description 1
- 235000019814 powdered cellulose Nutrition 0.000 description 1
- 229920003124 powdered cellulose Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
Изобретение относитс к области фосфорорганических соединений, а именно к новому способу получени функциональнозамещенных диалкилфосфатов общей формулыThe invention relates to the field of organophosphorus compounds, namely, to a new method for producing functionally substituted dialkyl phosphates of the general formula
(RO).P{ он(RO) .P {he
где R - функциональнозамещенный углеводородный радикал.where R is a functionally substituted hydrocarbon radical.
Известен способ получени функциональнозамещенных диалкилфосфатов обработкой хлорокиси фосфора водой при мол рном соотношении реагентов 1:1 с последующим удалением хлористого водорода и обработкой гидролизата высшим спиртом при мол рном соотношении последнего к хлорокиси фосфора, равном 2: 1.A known method of producing functionally substituted dialkyl phosphates is treated by treating phosphorus oxychloride with water at a 1: 1 molar ratio of reagents, followed by removing hydrogen chloride and treating the hydrolyzate with a higher alcohol at a molar ratio of phosphorus oxychloride of 2: 1.
Однако функциональнозамещенные диалкилфосфаты , такие, например, как дитетрагидрофурфурилфосфат получаютс с низким выходом или вовсе не получаютс , как, например , фосфорсодержащие полимеры на основе целлюлозы и лигнина.However, functionally substituted dialkyl phosphates, such as, for example, diterahydrofurfuryl phosphate, are obtained with low yield or are not obtained at all, such as, for example, cellulose-based phosphorus-containing polymers of lignin.
С целью расширени сырьевой базы и ассортимента диалкилфосфатов предлагаетс новый способ получени функциональнозамещенных диалкилфосфатов, который заключаетс в том, что фосфорноватистую кислоту подвергают взаимодействию со спиртом, четыреххлористым углеродом и основанием, например триэтиламином.In order to expand the raw material base and range of dialkyl phosphates, a new method is proposed for the preparation of functional substituted dialkyl phosphates, which consists in the fact that hypophosphorous acid is reacted with alcohol, carbon tetrachloride and a base, such as triethylamine.
Процесс может быть проведен при нагревании до 100-125°С в среде инертного органического растворител , например эфира или диоксана.The process can be carried out by heating to 100-125 ° C in an inert organic solvent, such as ether or dioxane.
Предлагаемый способ позвол ет получать с большим выходом функциональнозамещенные диалкилфосфаты, например, дитетрагидрофурфурилфосфат или такие сложные производные , как фосфорсодержащие полимеры на основе целлюлозы и лигнина, содерн ащиеThe proposed method allows to obtain functionally substituted dialkyl phosphates, for example, ditetrahydrofurfuryl phosphate or such complex derivatives as cellulose-based phosphorus-containing polymers, with a high yield.
монотонные кислофосфатные фрагменты.monotone acid-phosphate fragments.
Все эти вещества представл ют интерес какAll of these substances are of interest as
комплексообразователи. Пример 1.complexing agents. Example 1
а) В колбу с обратным холодильником и мешалкой помещают 16,2 г порошкообразной целлюлозы, 150 мл диоксана, 33 г триэтиламина , 6,6 г фосфорноватистой кислоты и 30 г четыреххлористого углерода. Затем смесь нагревают в течение 3 час при 100°С. После охлаждени реакционную смесь фильтруют, осадок промывают 30 мл теплого хлороформа,a) In a flask with a reflux condenser and a stirrer, 16.2 g of powdered cellulose, 150 ml of dioxane, 33 g of triethylamine, 6.6 g of hypophosphorous acid and 30 g of carbon tetrachloride are placed. Then the mixture is heated for 3 hours at 100 ° C. After cooling, the reaction mixture is filtered, the precipitate is washed with 30 ml of warm chloroform,
30 лы холодного хлороформа и два раза по 30 мл метанола (после промывани вещество не должно содержать хлоргидрата амина). Далее продукт выдерживают в вакуумном эксикаторе до посто нного веса. Выход 15,5 г.30 liters of cold chloroform and two times 30 ml of methanol (after washing, the substance should not contain amine hydrochloride). Next, the product is kept in a vacuum desiccator until constant weight. Output 15.5 g
б) Аналогично описанному выше, но с целлюлозной ватой, получен продукт. Выход 15,9 г; содержание фосфора 5,4%.b) In the same way as described above, but with cellulose wadding, a product is obtained. Yield 15.9 g; phosphorus content of 5.4%.
Пример 2. Аналогично методике получени фосфорилированной целлюлозы получают тетрагидрофурфурилофосфат из 10,2 г тетрагидрофурфурилового спирта, 50 г четыреххлористого углерода, 3,3 г фосфорноватистой кислоты и 16 2 триэтиламина в 80 мл эфира. Выход продукта 7,6 г (53%). Эквивалент титровани 301,303 (вычисленна величина 298).Example 2. Analogously to the method of obtaining phosphorylated cellulose, tetrahydrofurfuryl phosphate is prepared from 10.2 g of tetrahydrofurfuryl alcohol, 50 g of carbon tetrachloride, 3.3 g of hypophosphorous acid and 16 2 triethylamine in 80 ml of ether. The product yield of 7.6 g (53%). Equivalent to the titration of 301,303 (calculated value 298).
Пример 3. Аналогично методике примера 1 из 15 г гидролизного лигнина Саратовского завода, 120 мл диоксана, 30 мл триэтиламина, 30 г четыреххлористого углерода и 6,5 г фосфорноватистой кислоты получают 15,1 г фосфорилироваццого Example 3. Similarly to the method of example 1, 15.1 g of phosphorylated hydrochloride is obtained from 15 g of hydrolysis lignin of the Saratov plant, 120 ml of dioxane, 30 ml of triethylamine, 30 g of carbon tetrachloride and 6.5 g of hypophosphorous acid
лигнина с содерл анием фосфора 6,7%.lignin with phosphorus content of 6.7%.
Предмет изобретени Subject invention
Claims (3)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU319604A1 true SU319604A1 (en) |
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