SU345123A1 - METHOD OF OBTAINING CHLOROMETHYL ALCOHOL ETHERS - Google Patents
METHOD OF OBTAINING CHLOROMETHYL ALCOHOL ETHERSInfo
- Publication number
- SU345123A1 SU345123A1 SU1485752A SU1485752A SU345123A1 SU 345123 A1 SU345123 A1 SU 345123A1 SU 1485752 A SU1485752 A SU 1485752A SU 1485752 A SU1485752 A SU 1485752A SU 345123 A1 SU345123 A1 SU 345123A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- alcohol ethers
- alcohol
- alcohols
- paraform
- obtaining
- Prior art date
Links
- -1 CHLOROMETHYL ALCOHOL ETHERS Chemical class 0.000 title description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 5
- 229920002866 paraformaldehyde Polymers 0.000 claims description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 235000005074 zinc chloride Nutrition 0.000 claims description 3
- 239000011592 zinc chloride Substances 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 2
- 239000012320 chlorinating reagent Substances 0.000 claims 2
- 230000003993 interaction Effects 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- NUXORHITUOSOCO-UHFFFAOYSA-N 1,1-dinitropropan-1-ol Chemical compound CCC(O)([N+]([O-])=O)[N+]([O-])=O NUXORHITUOSOCO-UHFFFAOYSA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- HRQGCQVOJVTVLU-UHFFFAOYSA-N Bis(chloromethyl) ether Chemical class ClCOCCl HRQGCQVOJVTVLU-UHFFFAOYSA-N 0.000 description 1
- UCFFGYASXIPWPD-UHFFFAOYSA-N Methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Description
Изобретение относитс к способу получени хлорметиловых эфиров спиртов, которые могут найти широкое применение в качестве промежуточных продуктов в технологии органического синтеза.This invention relates to a process for the preparation of chloromethyl ethers of alcohols, which can be widely used as intermediates in organic synthesis technology.
Известен способ получени хлорметиловых эфиров спиртов путем взаимодействи спиртов с параформом и хлористым водородом. Недостатком такого способа вл етс использование большого избытка хлористого водорода при продолжительности процесса 4-6 час. Выход целевых продуктов при этом не превышает 75%.A method of producing chloromethyl esters of alcohols by reacting alcohols with paraform and hydrogen chloride is known. The disadvantage of this method is the use of a large excess of hydrogen chloride with a process time of 4-6 hours. The yield of the target products does not exceed 75%.
С целью увеличени выхода целевого продукта и расширени ассортимента готового продукта предложено спирты и параформ подвергать взаимодействию с хлористым тионилом в присутствии катализаторов протонного или апротонного типа, например серной кислоты, хлористого цинка.In order to increase the yield of the target product and expand the range of the finished product, it was proposed to alcohols and paraforms to react with thionyl chloride in the presence of proton or aprotic catalysts such as sulfuric acid, zinc chloride.
Процесс можно вести как в среде растворител , так и без него.The process can be conducted both in the medium of solvent and without it.
В качестве спирта целесообразно примен ть нитроспирт.It is advisable to use nitro alcohol as an alcohol.
Предлагаемый способ прост в техническом оформлении. При использовании в этом способе динитропропанола был получен хлорметиловый эфир, не описанный в литературе. Выход целевых продуктов по предлагаемому способу 85-98%.The proposed method is simple in technical design. When dinitropropanol was used in this process, chloromethyl ether not described in the literature was obtained. The yield of the target products by the proposed method 85-98%.
Пример 1. а) Хлорметиловый эфир динитропропанола .Example 1. a) Dinitropropanol chloromethyl ester.
Смесь 6,0 г динитропропанола, 1,5 г параформа , 0,08 г хлористого цинка и 5,8 г хлористого тионила в 15 мл дихлорэтана при перемешивании нагревают при в течение 2 час. После отгонки легколетучих остаток разгон ют. Получают 7,5 г (94,5%) веш .ества, т. кип. 93-95°С/1,5 мм рт. ст. 1.4630, df 1,3925.A mixture of 6.0 g of dinitropropanol, 1.5 g of paraform, 0.08 g of zinc chloride and 5.8 g of thionyl chloride in 15 ml of dichloroethane are heated under stirring for 2 hours. After distillation, the volatile residue is distilled. Obtain 7.5 g (94.5%) of oil, t. Kip. 93-95 ° C / 1.5 mm Hg. Art. 1.4630, df 1.3925.
Найдено, %: С 23,82; Found,%: C 23.82;
Н 3,36; N 14,23; С1 17,75.H 3.36; N 14.23; C1 17.75.
C4H705N2C1.C4H705N2C1.
Вычислено, %: Calculated,%:
С 24,18; Н 3,53; N 14,10; С1 17,86.C 24.18; H 3.53; N 14.10; C1 17.86.
б) К смеси 10 г конц. H2SO4, 1,5 г параформа и 5,8 г SOCla при 20-23°С приливают раствор 6,0 г динитропропанола в 10 мл дихлорэтана и выдерлсивают при этой температуре 1,5 час. После отгонки легколетучих и фракционировани получают 6,9 г (87,3%) хлорметилового эфира динитропропанола, т. кип. 83-85°С/1 Л1М рт. ст., По 1,4614.b) To a mixture of 10 g of conc. H2SO4, 1.5 g of paraform and 5.8 g of SOCla at 20–23 ° C, a solution of 6.0 g of dinitropropanol in 10 ml of dichloroethane is poured and pulled at this temperature for 1.5 hours. After distilling off volatile materials and fractionating, 6.9 g (87.3%) of dinitropropanol chloromethyl ester are obtained, m.p. 83-85 ° С / 1 Л1М рт. Art., According to 1.4614.
Найдено, %: С1 17,96.Found%: C1 17.96.
Вычислено, %: С1 17,86.Calculated,%: C1 17.86.
Пример 2. Хлорметиловый эфир этиленхлоргидрина .Example 2. Ethylene chlorohydrin chloromethyl ester.
ленхлоргидрина (т. кип. 128-130°С) и выдерживают ее 1 час при 30-40°С. После фракционировани получают 22,0 г (85%) целевого продукта, т. кип. 48°С/10 мм рт. ст., п 1,4570.lenchlorohydrin (t. Kip. 128-130 ° C) and maintain it for 1 hour at 30-40 ° C. After fractionation, 22.0 g (85%) of the desired product are obtained, t. 48 ° C / 10 mmHg Art., p 1.4570.
Предмет изобретени Subject invention
Claims (3)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU345123A1 true SU345123A1 (en) |
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