SU1397435A1 - Method of producing diethyldithiodiethyl ether of succinic acid - Google Patents
Method of producing diethyldithiodiethyl ether of succinic acid Download PDFInfo
- Publication number
- SU1397435A1 SU1397435A1 SU864045853A SU4045853A SU1397435A1 SU 1397435 A1 SU1397435 A1 SU 1397435A1 SU 864045853 A SU864045853 A SU 864045853A SU 4045853 A SU4045853 A SU 4045853A SU 1397435 A1 SU1397435 A1 SU 1397435A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- succinic acid
- diethyl
- producing
- diethyldithiodiethyl
- ether
- Prior art date
Links
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 238000000034 method Methods 0.000 title claims description 10
- 239000001384 succinic acid Substances 0.000 title claims description 3
- JDFNCKFUPBFDLW-UHFFFAOYSA-N 3,3-diethyl-1,4,5-oxadithiepane Chemical compound C(C)C1(COCCSS1)CC JDFNCKFUPBFDLW-UHFFFAOYSA-N 0.000 title 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract description 6
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 claims abstract 2
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 claims abstract 2
- CETBSQOFQKLHHZ-UHFFFAOYSA-N Diethyl disulfide Chemical compound CCSSCC CETBSQOFQKLHHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 3
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 abstract description 6
- 230000002378 acidificating effect Effects 0.000 abstract description 3
- -1 diethyl dithio diethyl Chemical group 0.000 abstract description 3
- 239000003345 natural gas Substances 0.000 abstract description 3
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 239000003463 adsorbent Substances 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 150000007970 thio esters Chemical class 0.000 abstract 1
- 238000005292 vacuum distillation Methods 0.000 description 6
- 239000012429 reaction media Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical group CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 1
- CGBYBGVMDAPUIH-UHFFFAOYSA-N acide dimethylmaleique Natural products OC(=O)C(C)=C(C)C(O)=O CGBYBGVMDAPUIH-UHFFFAOYSA-N 0.000 description 1
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Изобретение касаетс тиоэфиров кислот, в частности получени ди- этилдитиодиэтиловрго эфира нтарной кислоты, который может быть использован как адсорбент Дл очистки кислых компонентов природного газа. Синтез ведут реакцией диэтилового эфира ма- леиновой кислоты с диэтилсульфидом при мол рном соотношении 1-2:1 при температуре 80-130 С в присутствии пиперидина. Выход 66,6%, т.кип. 180- 181 С при 1 мм рт.ст.The invention relates to thioesters of acids, in particular to the preparation of diethyl dithio diethyl ester of succinic acid, which can be used as an adsorbent for purifying the acidic components of natural gas. Synthesis is carried out by reacting maleic acid diethyl ester with diethyl sulfide at a molar ratio of 1-2: 1 at a temperature of 80-130 ° C in the presence of piperidine. Yield 66.6%, bk. 180-181 C at 1 mm Hg.
Description
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И-зобретение относитс к новому способу получени нового соединени . иэтилдитиoдиэтилoвoгo эфира нтарной кислоты формулыThe invention relates to a new method of obtaining a new compound. Ethyldithio diethyl ester of succinic acid of the formula
CjHs-S-CH-COOCjHg C2H5-S-CH-COOC2H5CjHs-S-CH-COOCjHg C2H5-S-CH-COOC2H5
к0торый может быть использован в качестве абсорбента дл очистки кислых крмпонентов природного газа.the latter can be used as an absorbent for the purification of acidic components of natural gas.
Целью изобретени вл етс разра- бЬтка нового способа получени ново- rjo соед1даени I, обладающего ценными свойствами, что достигаетс взаимодействием дизтилового эфира малеино- врй кислоты с диэтршдисульфидом в присутствии пиридина в качестве ката л|изатора при 80-130 С.The aim of the invention is to develop a new method of producing Novo Compound I, which possesses valuable properties, which is achieved by reacting dimethyl maleic acid ester with diethyl disulfide in the presence of pyridine as catalysts at 80-130 C.
I П р и м е р 1. В четырехгорлую кЬлбу, снабженную eшaлкoй, обратным л}олодилышком, термометром и капельной воронкой, помещают 25,8 г (0,15 моль) дизтилового эфира малеи- новой кислоты (ДЭЭМК) и 12,2 г (О,1 моль) диэтютдисульфида (ДЭДС). Ери перемешивании добавл ют 3-4 капли пиперидина в качестве катализатора . Реакци протекает при 80°С, про- Л0лжительность реакции 8 ч. Полученна реакционна смесь подвергаетс вакуумной перегонке;. В результате по ручаетс 19,6 г маслообразной, свет- ло-коричневой жидкости, имеющей т.ки 180-131 С/ мм рт.ст.I Example 1. In a four-necked club, equipped with an e-shake, inverse, a young girl, a thermometer, and an addition funnel, 25.8 g (0.15 mol) of maleic acid dimethyl ester (DEEM) and 12.2 g (O, 1 mol) of diethyl disulfide (DEDS). 3-4 drops of piperidine as a catalyst are added with stirring. The reaction proceeds at 80 ° C, the reaction time is 8 hours. The resulting reaction mixture is subjected to vacuum distillation ;. As a result, 19.6 g of an oily, light brown liquid with a content of 180-131 C / mmHg was obtained.
,1О, 1O
1,4650, d. - 1,0687, MRj, вычислено 76,20/найдено 76,15 Найдено, %: С 57,5;; Н 9,81; 21,5; О 11,2.1.4650, d. - 1.0687, MRj, calculated 76.20 / found 76.15 Found,%: C 57.5 ;; H 9.81; 21.5; About 11.2.
Вычислено, %: С 57,32;; Н 9,5; $ 21,67; О 11,51.Calculated,%: C 57.32 ;; H 9.5; $ 21.67; About 11.51.
При этом выход составл ет 66,6% (J5T теоретического.The yield is 66.6% (J5T theoretical.
Пример 2. Процесс проводит- С аналогично примеру 1, измен етс Только теьтература. В реакционной Среде температура поддерживаетс 90°С в течение 8 ч. После вакуумной Перегонки получают 22,5 г целевогоExample 2. The process is carried out - With analogy to Example 1, only the temperature change is changed. In the reaction medium, the temperature is maintained at 90 ° C for 8 hours. After vacuum distillation, 22.5 g of the desired product is obtained.
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продукта. При этом выход, составл ет 76,53% от теоретического.product. In this case, the yield is 76.53% of the theoretical.
Пример 3. Процесс провод т аналогично примеру 1. Температура реакционной среды поддерживаетс в течение 8 ч. После вакуумной перегонки получают 24,84 г целевого продукта. При этом выход составл ет 84,51% От теоретического.Example 3. The process is carried out analogously to example 1. The temperature of the reaction medium is maintained for 8 hours. After vacuum distillation, 24.84 g of the expected product is obtained. The yield is 84.51% of theoretical.
Пример 4. Процесс провод т аналогично примеру 1. Температура в реакционной среде 110 С. После вакуумной перегонки получают 27,2 г ди- этилдитиодиэтилового эфира нтарной кислоты, выход которого при этом составл ет 92,58% от теоретического.Example 4. The process is carried out analogously to example 1. The temperature in the reaction medium is 110 ° C. After vacuum distillation, 27.2 g of succinic acid diethyl dithiodiethyl ester are obtained, the yield of which is 92.58% of the theoretical value.
Пример 5. Процесс провод т аналогично примеру 1. Температура в реакционной среде )20 С.Example 5. The process is carried out analogously to example 1. The temperature in the reaction medium) 20 C.
После вакуумной перегонки получают 27,87 г целевого продукта. При этом выход составл ет 94,81% от теоретического .After vacuum distillation, 27.87 g of the expected product are obtained. In this case, the yield is 94.81% of the theoretical.
Пример 6. Процесс провод т аналогично примеру 1, Температура в реакционной зоне 30°С, После вакуумной перегонки получают 28,0 г продукта , выход которого при этом составл ет 95,35% от теоретического.Example 6. The process is carried out analogously to example 1, the temperature in the reaction zone is 30 ° C. After vacuum distillation, 28.0 g of product are obtained, the yield of which is 95.35% of theoretical.
Таким образом, предлагаемый способ позвол ет получить новое соединение , которое может быть использовано в качестве абсорбента дл очистки кислых компонентов природного газа.Thus, the proposed method allows to obtain a new compound that can be used as an absorbent for the purification of the acidic components of natural gas.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU864045853A SU1397435A1 (en) | 1986-03-04 | 1986-03-04 | Method of producing diethyldithiodiethyl ether of succinic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU864045853A SU1397435A1 (en) | 1986-03-04 | 1986-03-04 | Method of producing diethyldithiodiethyl ether of succinic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1397435A1 true SU1397435A1 (en) | 1988-05-23 |
Family
ID=21229686
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU864045853A SU1397435A1 (en) | 1986-03-04 | 1986-03-04 | Method of producing diethyldithiodiethyl ether of succinic acid |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU1397435A1 (en) |
-
1986
- 1986-03-04 SU SU864045853A patent/SU1397435A1/en active
Non-Patent Citations (1)
| Title |
|---|
| Авторское свидетельство СССР- № 154262, кл. С 07 С 153/00, 1963. * |
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