SU218140A1 - METHOD OF OBTAINING ETHYL-p-NAFTIL-p, p-DICHLOROVINYL-PHOSPHATE - Google Patents
METHOD OF OBTAINING ETHYL-p-NAFTIL-p, p-DICHLOROVINYL-PHOSPHATEInfo
- Publication number
- SU218140A1 SU218140A1 SU1157494A SU1157494A SU218140A1 SU 218140 A1 SU218140 A1 SU 218140A1 SU 1157494 A SU1157494 A SU 1157494A SU 1157494 A SU1157494 A SU 1157494A SU 218140 A1 SU218140 A1 SU 218140A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- dichlorovinyl
- phosphate
- naftil
- obtaining ethyl
- ether
- Prior art date
Links
- 239000010452 phosphate Substances 0.000 title description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- HFFLGKNGCAIQMO-UHFFFAOYSA-N Chloral Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K [O-]P([O-])([O-])=O Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- FBAMIUQPWRXPFT-UHFFFAOYSA-N naphthalen-2-yl phosphite Chemical compound C1=CC=CC2=CC(OP([O-])[O-])=CC=C21 FBAMIUQPWRXPFT-UHFFFAOYSA-N 0.000 description 1
- RYBBIOGLGIGEOB-UHFFFAOYSA-N naphthalen-2-ylphosphonous acid Chemical compound C1=CC=CC2=CC(P(O)O)=CC=C21 RYBBIOGLGIGEOB-UHFFFAOYSA-N 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
Изобретение касаетс способа получени этил-р-нафтил-р,р-дихлорвинилфосфата общей формулыThe invention relates to a process for the preparation of ethyl p-naphthyl-p, p-dichlorovinyl phosphate of the general formula
р R
о about
Соединение может быть использовано в Сельском хоз йстве.The compound can be used in agriculture.
Предлагаемый способ получени основан на взаимодействии дихлорангидрида р-нафтилфосфористой кислоты с этанолом в присутствии пиридина с последующей обработкой хлоралем при охлаждении в эфире.The proposed method of preparation is based on the interaction of p-naphthylphosphorous acid dichlorohydride with ethanol in the presence of pyridine, followed by treatment with chloral while cooling in ether.
Пример. В трехгорлую колбу, снабженную мешалкой, обратным холодильником и капельной воронкой, помещают 73,6 г (0,3 моль) хлорангидрида р-нафтилфосфориотой кислоты, растворенного в 800 мл абсолютированного эфира.Example. In a three-necked flask equipped with a stirrer, a reflux condenser and a dropping funnel, 73.6 g (0.3 mol) of p-naphthylphosphorylate acid chloride dissolved in 800 ml of an absolute ether are placed.
К эфирному раствору хлорангидрида при непрерывном перемешивании и наружном охлаждении (до - 5-0°С) добавл ют по капл м смесь 27,7 г (0,6 моль) абсолютированного этанола и 47,7 г (0,6 моль) пиридина.Under continuous stirring and external cooling (up to –5–0 ° C), a mixture of 27.7 g (0.6 mol) of absolute ethanol and 47.7 g (0.6 mol) of pyridine is added dropwise to the ether solution of the acid chloride.
должают еще 30 мин при комнатной температуре , затем отдел ют образовавшуюс хлористоводородную соль пиридина. Из фильтрата отгон ют растворитель (эфир), оставшуюс Лсидкость дважды перегон ют в вакууме.continue for another 30 minutes at room temperature, then the resulting pyridine hydrochloride salt is separated. The solvent (ether) was distilled off from the filtrate, the remaining Liquidity was twice distilled in vacuo.
Температура кипени диэтил-|3-нафтилфосфита 145-147°С (2 мм рт. ст.); выход 66,5 г (84% от теоретического).The boiling point of diethyl | 3-naphthylphosphite is 145-147 ° C (2 mmHg); yield of 66.5 g (84% of theoretical).
К эфирному раствору 66,5 г (0,25 моль) диэтил-р-нафтилфосфита при непрерывном перемещивании и охлаждении до 5°С постепенно добавл ют 37,1 г (0,25 моль) хлорал , разбавленного равным объемом эфира. После прибавлени всего количества хлорал перемешивание реакционной смеси продол/кают еще в течение 1 час при комнатной температуре , затем отгон ют эфир и продукт реакции ДБал{ды перегон ют в вакууме.To the ethereal solution of 66.5 g (0.25 mol) of diethyl-p-naphthyl phosphite, while continuously moving and cooling to 5 ° C, 37.1 g (0.25 mol) of chloral, diluted with an equal volume of ether, is gradually added. After adding the total amount of chloral, stirring the reaction mixture for a further 1 hour at room temperature, then the ether is distilled off and the reaction product Dbal {dy is distilled in vacuum.
Выход 64 г (73,3% от теоретического).Output 64 g (73.3% of theoretical).
Этил-р-нафтил-р,р-дихлорвинилфосфат представл ет собой бесцветную жидкость со слабым запахом, т. кип. 161 - 163°С (0,1 ммEthyl p-naphthyl-p, p-dichlorovinyl phosphate is a colorless liquid with a faint odor, i.e. bale. 161 - 163 ° С (0.1 mm
ппpp
, ,20, ,20
1,3395; По 1,5630; MRo найдено 1.3395; 1.5630 each; MRo found
рт. ст.); 04Hg Art.); 04
84,38; MR вычислено 84,25.84.38; MR calculated 84.25.
Найдено, %: С1 20,12; 20,18; Р 8,68; 8,83.Found,%: C1 20,12; 20.18; P 8.68; 8.83.
Cl4Hi3Cl2O4P. 3 других органических растворител х, но нерастворим в воде. Предмет изобретени 1. Способ получени этил-р-нафтил-р,|3-дихлорвинилфосфата , отличающийс тем, что 4 дихлорангидрид |3-нафтилфосфористой кислоты подвергают взаимодействию с этанолом в присутствии пиридина с последуюш;ей обработкой хлоралем при охлаждении в среде ор5ганического растворител . 2. Способ по п. 1, отличающийс тем, что охлаждение ведут до О-5°С.Cl4Hi3Cl2O4P. 3 other organic solvents, but insoluble in water. Subject of the invention 1. A method for producing ethyl p-naphthyl-p, 3-dichlorovinyl phosphate, characterized in that 4 (3-naphthyl phosphonous acid) dichlorohydride is reacted with ethanol in the presence of pyridine followed by treatment with chloral while cooling in an organic solvent. 2. A method according to claim 1, characterized in that the cooling is carried out to about -5 ° C.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU218140A1 true SU218140A1 (en) |
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