SU164251A1 - ELECTROCHEMICAL METHOD FOR OBTAINING DIETHRONS OF HIGHER UNSATURATED DICARBONIC ACIDS - Google Patents
ELECTROCHEMICAL METHOD FOR OBTAINING DIETHRONS OF HIGHER UNSATURATED DICARBONIC ACIDSInfo
- Publication number
- SU164251A1 SU164251A1 SU842955A SU842955A SU164251A1 SU 164251 A1 SU164251 A1 SU 164251A1 SU 842955 A SU842955 A SU 842955A SU 842955 A SU842955 A SU 842955A SU 164251 A1 SU164251 A1 SU 164251A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- diethrons
- obtaining
- higher unsaturated
- electrochemical method
- dicarbonic acids
- Prior art date
Links
- 239000002253 acid Substances 0.000 title description 6
- 150000007513 acids Chemical class 0.000 title description 4
- 238000002848 electrochemical method Methods 0.000 title description 3
- 238000005868 electrolysis reaction Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 5
- 150000001991 dicarboxylic acids Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000003792 electrolyte Substances 0.000 description 3
- 229910002804 graphite Inorganic materials 0.000 description 3
- 239000010439 graphite Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N Sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- -1 dimethyl ester Chemical class 0.000 description 2
- 230000001264 neutralization Effects 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- CWOVOJUKEQPFBA-UHFFFAOYSA-N 6-O-ethyl 1-O-methyl hexanedioate Chemical compound CCOC(=O)CCCCC(=O)OC CWOVOJUKEQPFBA-UHFFFAOYSA-N 0.000 description 1
- UOBSVARXACCLLH-UHFFFAOYSA-M 6-methoxy-6-oxohexanoate Chemical compound COC(=O)CCCCC([O-])=O UOBSVARXACCLLH-UHFFFAOYSA-M 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 101700084542 TCIM Proteins 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N Tetrafluoroethylene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- ALOUNLDAKADEEB-UHFFFAOYSA-N dimethyl decanedioate Chemical compound COC(=O)CCCCCCCCC(=O)OC ALOUNLDAKADEEB-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N dimethyl ether Chemical class COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 150000005218 dimethyl ethers Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 239000008079 hexane Substances 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- AGZBSGLJZHUFPS-UHFFFAOYSA-N tetradec-7-enedioic acid Chemical compound OC(=O)CCCCCC=CCCCCCC(O)=O AGZBSGLJZHUFPS-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
Диэфиры высших ненасыщенных дикарбоиовых кислот могут быть использованы дл получени синтетических смол, с.мазочных материалов и других важных продуктов.Diesters of higher unsaturated dicarboic acids can be used to make synthetic resins, s. Lubricants and other important products.
Известен электрохимический способ получени диэфиров высших ненасыщенных дикарбоновых кислот электролизом .метанольных растворов солен моноэфира низщих дикарбоновых кислот в присутствии 1,3-бутадиена на платиновом аноде. Выход диметилового эфира 6,10-гександекадиен-1,16-дикарбоновой кислоты 49%.A known electrochemical method for the preparation of diesters of higher unsaturated dicarboxylic acids by the electrolysis of methanol solutions of the salts of the monoester of the lower dicarboxylic acids in the presence of 1,3-butadiene on a platinum anode. The yield of dimethyl ester of 6,10-hexane decadiene-1,16-dicarboxylic acid is 49%.
Предлагаемый электрохи.мический способ получени диэфиров высших ненасыщенных дикарбоновых кислот отличаетс от известного тем, что электролиз ведут на графитовом аноде под давление1М 1,3-бутадиена около 50 атм. Это позвол ет направить реакцию в сторону образовани диэфира кислоты с двум двойными св з ми, а также повысить выход целевого продукта до 67%.The proposed electrochemical method for the preparation of diesters of higher unsaturated dicarboxylic acids differs from the well-known fact that electrolysis is carried out on a graphite anode under a pressure of 1M 1,3-butadiene of about 50 atm. This makes it possible to direct the reaction towards the formation of a double-diester acid, as well as to increase the yield of the target product to 67%.
Пример. В стальной электролизер-автоклав емкостью 260 мл помещают электродчый комплект, состо щий из графитового анода с пониженной пористостью, выполненного в виде стержн , и перфорированного цилиндра из никелевой фольгн, служащего катодом. Минимальное рассто ние между электродами (3 мм) фиксируют при помощи изол торов, изготовленных в виде колец из фторопласта-4.Example. In a steel electrolyzer-autoclave with a capacity of 260 ml is placed an electrode set consisting of a graphite anode with a reduced porosity, made in the form of a rod, and a perforated cylinder of nickel foil serving as a cathode. The minimum distance between the electrodes (3 mm) is fixed using insulators made in the form of fluoroplast-4 rings.
В электролизер заливают электролит, состо щий из 32 г Jмoнoмeтилaдипинaтa, 2,8 г едкого кали, 44 г 1,3-бутадиена и 128 мл метанола. Электролиз провод т при анодной плотности тока 200 а/м- и температуре . Конечное давление в электролизере 47 атм.The electrolyte is filled with an electrolyte consisting of 32 g of mono methyl ethyl adipate, 2.8 g of potassium hydroxide, 44 g of 1,3-butadiene and 128 ml of methanol. The electrolysis is carried out at an anode current density of 200 a / m and temperature. The final pressure in the electrolyzer is 47 atm.
После окончани электролиза от элекгролита отгон ют непрореагировавщий 1,3-бутадиен , раствор разбавл ют 2-3-кратным избытком воды и из образовавшегос водно-спиртового раствора серным эфиром экстрагируют нейтральный продукт реакции п непрореагировавщий монометиладипинат. После высущивани экстракта и отгонки сериого эфираAfter the end of electrolysis, unreacted 1,3-butadiene is distilled off from the electrolyte, the solution is diluted with a 2–3-fold excess of water and the neutral reaction product p unreacted monomethyl adipate is extracted from the resulting aqueous-alcoholic solution. After drying the extract and distilling the ether.
продукт обрабатывают 12%-ным раствором бикарбоната натри дл отделени кислого моноэфира. Полученный нейтральный продукт электролиза, состо щий из смеси диметиловых эфиров высших ненасыщенных кислот и себациновой кислоты, разгон ют под вакуумом (2 мм рт. ст.). Выход диметилового эфира 6,10-гексадекадиен-1,16-дикарбоиовой кислоты по веществу и по току 67%, выход 6-додецен1 ,12-дикарбоновой кислоты - 22,3%, выходthe product is treated with a 12% sodium bicarbonate solution to separate the acidic monoester. The obtained neutral electrolysis product, consisting of a mixture of dimethyl ethers of higher unsaturated acids and sebacic acid, is dispersed under vacuum (2 mm Hg). The output of dimethyl ether 6,10-hexadecadiene-1,16-dicarboic acid by substance and current 67%, the yield of 6-dodecen1, 12-dicarboxylic acid - 22.3%, yield
диметилсебацпната -dimethyl sebacate -
Предмет изобретени 3 кислот путем электролиза метанольиых растворов солей монометиловых эфиров низших ненасыщенных дикарбоновых кислот в присутствии 1,3-бутадиена, отличающийс 4 TCiM, что, с целью повышени выхода диэфира кислоты с двум двойными св з ми, процесс электролиза ведут на графитовом аноде под давлением около 50 атм.The subject matter of the invention is 3 acids by electrolysis of methanol solutions of the salts of monomethyl ethers of lower unsaturated dicarboxylic acids in the presence of 1,3-butadiene, characterized by 4 TCiM, which, in order to increase the yield of the acid diester with two double bonds, the electrolysis process is carried out on a graphite anode under pressure about 50 atm.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU164251A1 true SU164251A1 (en) |
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