SU182710A1 - METHOD OF OBTAINING COUPPED NITRODIENES - Google Patents
METHOD OF OBTAINING COUPPED NITRODIENESInfo
- Publication number
- SU182710A1 SU182710A1 SU908259A SU908259A SU182710A1 SU 182710 A1 SU182710 A1 SU 182710A1 SU 908259 A SU908259 A SU 908259A SU 908259 A SU908259 A SU 908259A SU 182710 A1 SU182710 A1 SU 182710A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- nitrodienes
- coupped
- obtaining
- sodium
- mol
- Prior art date
Links
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N benzohydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000001187 sodium carbonate Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Description
Известно получение 1-нитро-1,4-дифенилбутадиена-1 ,3 путем взаимодействи 1,4-динитро-1 ,4-дифепилбутадиена-2 с водным аммиаком .It is known to prepare 1-nitro-1,4-diphenylbutadiene-1, 3 by reacting 1,4-dinitro-1, 4-dipepylbutadiene-2 with aqueous ammonia.
С целью увеличени выхода продукта и расширени ассортимента, предложен способ, состо щий во взаимодействии 1,4-динитробутенов-2 с метилатом натри или карбонатом натри при температуре 35°С.In order to increase product yield and expand the range, a method has been proposed which consists in the interaction of 1,4-dinitrobutenes-2 with sodium methoxide or sodium carbonate at a temperature of 35 ° C.
Пример 1. 1-Н ит р о б у т а д и е н-1,3. К суспензии 5.8 г (0,04 моль) 1,4-динитробутена-2 в 80 мл бензола при 35°С в присутствии гидрохинона в течение 1,5 час прибавл ют по капл м 4%-ный раствор карбоната натри (0,02 моль) до по влени слабощелочной среды. Реакционную массу охлаждают до 0°С и подкисл ют 1 н. сол ной кислотой до слабокислой реакции. После удалени твердого остатка и разделени слоев бензольный раствор промывают водой и сушат безводным сульфатом магни . 1-Нитробутадиен-1,3 отгон ют в виде желтого масла со свойствами лакриматора с т. кип. 59°С (12 мм рт. ст.);Example 1. 1-H it p about b and t and d and e n-1,3. To a suspension of 5.8 g (0.04 mol) of 1,4-dinitrobutene-2 in 80 ml of benzene at 35 ° C in the presence of hydroquinone, a 4% solution of sodium carbonate (0.02 mole) until the appearance of a weak alkaline medium. The reaction mass is cooled to 0 ° C and acidified with 1N. hydrochloric acid to weakly acidic reaction. After removing the solid residue and separating the layers, the benzene solution is washed with water and dried with anhydrous magnesium sulfate. 1-Nitrobutadiene-1,3 is distilled off as a yellow oil with lacrimator properties with m.p. 59 ° С (12 mm of mercury);
-,18-,18
1,5390.1.5390.
Найдено N 13,87; 14,22%.Found N, 13.87; 14.22%.
ГО эфира в присутствии гидрохинона при 35°С пр11бавл ют по капл м 0,9 г (0,025 моль натри в 18 мл сухого метилового спирта. После выдержки и охлаждени в течение 2 час отфильтровывают 3,4 г соли исходного динитробутена-2 , а фильтрат концентрируют под вакуумом , затем раствор ют в эфире, промывают водой, сушат безводным сульфатом магни . 1-Нитро-2,3-диметилбутадиен-1,3 отгон ют в виде светло-желтого масла с т. кип. 73°С (7 мм рт. ст.); Пр 1,5230, вл ющегос THd ether in the presence of hydroquinone at 35 ° C was added dropwise 0.9 g (0.025 mol of sodium in 18 ml of dry methyl alcohol. After aging and cooling for 2 hours, 3.4 g of salt of the starting dinitrobutene-2 was filtered and the filtrate concentrated under vacuum, then dissolved in ether, washed with water, dried with anhydrous magnesium sulphate. 1-Nitro-2,3-dimethyl-butadiene-1,3 is distilled off as a light yellow oil with bp 73 ° C (7 mm Hg. Art.); Pr 1,5230, which is
лакриматором (выход 60%).lacrimator (yield 60%).
Пайдепо N 11,40; 11,05о/о.Paidepo N 11.40; 11.05 o.
CeHaNOo.CeHaNOo.
Вычислено N ll,02VoП р и м ер 3. 1-Н и т р о-2,3-д и ф е н н л б утадиен-1 ,3. К суспензии 0,3 г (0,01 моль) 1,4-Д1Шитро-2,3-дифенилбутена-2 в 3 мл сухого метанола при 30°С и перемешивании прибавл ют 0,03 г (0,0013 моль) метилата натри в 3 мл спирта, причем исходный продукт сразу раствор етс . После выдерл ки в течение 5 мин в охлажденный раствор добавл ют кусочки льда (5 г), при этол выпадает 0,15 г мононитродиена (выход 60%), который после) перекристаллизации из водного метилового спирта имеет т. пл. 69°С. 34Calculated N ll, 02VoP r and world 3. 1-H and t r about-2,3-d and f en nn b utadiene-1, 3. To a suspension of 0.3 g (0.01 mol) of 1,4-D1 Shitro-2,3-diphenylbutene-2 in 3 ml of dry methanol at 30 ° C and 0.03 g (0.0013 mol) of sodium methoxide were added with stirring. in 3 ml of alcohol, the starting product immediately dissolving. After extracting ice for 5 minutes, pieces of ice (5 g) are added to the cooled solution, and ethanol gives 0.15 g of mononitrodiene (60% yield), which after recrystallization from aqueous methyl alcohol has an mp. 69 ° C. 34
тем, что, с целью увеличени выхода целевого вию с метилатом натри или карбонатом натпродукта , последние подвергают взаимодейст- ри при температуре 35°С.By the fact that, in order to increase the yield of the target with sodium methoxide or sodium by-product carbonate, the latter interact at a temperature of 35 ° C.
182710 182710
Publications (1)
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SU182710A1 true SU182710A1 (en) |
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