SU285924A1 - METHOD OF OBTAINING 2- (TRIALKILSILIL) ETHYL-2'-PHENYLVINYLSULFIDES - Google Patents
METHOD OF OBTAINING 2- (TRIALKILSILIL) ETHYL-2'-PHENYLVINYLSULFIDESInfo
- Publication number
- SU285924A1 SU285924A1 SU1334309A SU1334309A SU285924A1 SU 285924 A1 SU285924 A1 SU 285924A1 SU 1334309 A SU1334309 A SU 1334309A SU 1334309 A SU1334309 A SU 1334309A SU 285924 A1 SU285924 A1 SU 285924A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- phenylvinylsulfides
- phenylacetylene
- trialkilsilil
- ethyl
- obtaining
- Prior art date
Links
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Phenylacetylene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 claims description 7
- -1 ethyl2-phenylvinylsulfides Chemical class 0.000 claims description 7
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 239000010703 silicon Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 4
- DUYAAUVXQSMXQP-UHFFFAOYSA-M thioacetate Chemical class CC([S-])=O DUYAAUVXQSMXQP-UHFFFAOYSA-M 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- BDAWXSQJJCIFIK-UHFFFAOYSA-N Potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims 1
- 239000003518 caustics Substances 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000004665 trialkylsilyl group Chemical group 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 235000011118 potassium hydroxide Nutrition 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- QTFRQLVOEAETJY-UHFFFAOYSA-N 3-methoxy-2-(3-methoxyprop-1-en-2-ylsulfanyl)prop-1-ene Chemical compound COCC(=C)SC(=C)COC QTFRQLVOEAETJY-UHFFFAOYSA-N 0.000 description 1
- RVDSIVMDHHJMIS-UHFFFAOYSA-N S[SiH2]CC Chemical compound S[SiH2]CC RVDSIVMDHHJMIS-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000000111 anti-oxidant Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
Изобретение относитс к синтезу новых непредельных кремнийорганических соединений, содержащих серу общей формулыThis invention relates to the synthesis of new unsaturated organosilicon compounds containing sulfur of the general formula
Кз51С2Н45СН СНСбН5,Кз51С2Н45СН СНСбН5,
где R - алкил.where R is alkyl.
Полученные соединени могут представить интерес как потенциальные мономеры, реакционноспособные полупродукты, присадки к маслам, антиоксиданты.The resulting compounds may be of interest as potential monomers, reactive intermediates, oil additives, antioxidants.
Реакци присоединени кремнийорганических тиолов к ацетиленовым соединени м в присутствии едкого кали в среде органического растворител известна. Однако фенилацетилен в данной реакции не примен лс и присоединение кремнийсодержащих тиоацетатов к фенилацетилену неизвестно.The reaction of attaching the silicone thiols to acetylenic compounds in the presence of caustic potash in an organic solvent medium is known. However, phenylacetylene was not used in this reaction and the addition of silicon-containing thioacetates to phenylacetylene is unknown.
Предлагаемый способ состоит в том, что р-кремнийсодержащие меркаптаны или р-кремнийсодержащие тиоацетаты подвергают взаимодействию с феиилацетиленом в присутствии едкого кали или метилата натри в среде органического растворител , например метанола . Процесс желательно вести при нагревании до 60-70°С.The proposed method consists in the fact that p-silicon-containing mercaptans or p-silicon-containing thioacetates are reacted with feiyl acetylene in the presence of caustic potash or sodium methylate in an organic solvent medium, for example methanol. The process is preferably carried out when heated to 60-70 ° C.
этилсилнлэтилмеркаптана и через некоторое врем (10-20 мин) добавл ют 8 г фенилацетилена . Смесь греют 4-5 час ири 65-70С. По окончании реакции реакционную массу, предварительно разбавленную эфиром, несколько раз промывают подкисленной водой, а эфирный раствор сушат над NaoSO.i. В результате перегонки в вакууме выдел ют 14,6 г (66,6%) вещества с т. кип.178-179°С/4-5 мм ethylsilylmercaptan and after some time (10-20 minutes) 8 g of phenylacetylene are added. The mixture is heated for 4-5 hours iri 65-70С. At the end of the reaction, the reaction mass, previously diluted with ether, is washed several times with acidified water, and the ether solution is dried over NaSO2. As a result of the distillation in vacuum, 14.6 g (66.6%) of the substance with m.p. 178-179 ° C / 4-5 mm was isolated.
рг. ст., 1,5630, df 0,9690.Pr. Art., 1.5630, df 0.9690.
Найдено, %: С 68,99; II 9,41; S 11,51; Si 10,08.Found,%: C 68.99; II 9.41; S 11.51; Si 10.08.
1бП2бЬо1.1bP2bo1.
Вычислено, %: С 68,98; П 9,54; S 11,89; Si 9,87.Calculated,%: C 68.98; P 9.54; S 11.89; Si 9.87.
б) К раствору метилата Na, полученному из 0,05 г Na в 4 мл метанола, приливают 5 г (0,03 г-моль} меркаптана п через некоторое врем 2,4 г (0,023 г-.юль) фепилацетилепа. Реакциоппую массу нагревают 4-5 час приb) To a solution of Na methylate obtained from 0.05 g of Na in 4 ml of methanol, 5 g (0.03 g-mol} of mercaptan n are added; after some time 2.4 g (0.023 g -...yul) of fepyl-acetylpe. Reactant mass heat 4-5 hours at
65-70°С. Получают 4 г (63,5%) 65-70 ° C. Receive 4 g (63.5%)
2-триэтплсил ил-2-фенилэти л винил сульфида с т. киа. 206-207°С10 ммрт. ст., lA 1,5644, df 0,9667.2-triethyl il-2-phenylethyl l vinyl sulfide with m. Kia. 206-207 ° С10 mmrt. Art., lA 1,5644, df 0,9667.
в) К раствору 2,7 г (0,048 г-моль) КОН в 10 мл .метанола при нагревании и перемешивании прибавл ют эквимол рные количества триэтилсилилэтилтиоацетата 8,4 г (0,038 г-моль) и 3,8 г (0.038 г-моль) фенилацетилена . Врем нагревани 5-6 час, температура 70°С.c) To a solution of 2.7 g (0.048 g-mol) KOH in 10 ml of methanol, with heating and stirring, equimolar amounts of triethylsilyl ethylthio-acetate 8.4 g (0.038 g-mol) and 3.8 g (0.038 g-mol a) phenylacetylene. The heating time is 5-6 hours, the temperature is 70 ° C.
После обычной дл данных синтезов обработки выдел ют 5,2 г (50%) 2-триэтилсилил2-фенилэтилвинилсульфида с т. кип. 269-170°С/3-4 мм рт. ст., 1,5620,After the usual treatment for these syntheses, 5.2 g (50%) of 2-triethylsilyl-2-phenylethylvinyl sulfide with m.p. 269-170 ° С / 3-4 mm Hg. Art., 1.5620,
df 0,9683.df 0.9683.
Пример 2. 2-Триметилсилил-2-фенилэтилвииплсульфид .Example 2. 2-Trimethylsilyl-2-phenylethylphosphine.
Получают по методике «б из 0,1 г Na в 7 мл метанола, 7,4 г (0,055 г-моль) триметилсилилэтилмеркапта}1а и 4,4 г (0,043 г-моль фенилацетилена. Выдел ют 5 г (49%) 2-триметилсилил - 2 - фенилэтилвинилсульфида с т. кип. 137-138 0/2-3 мм рт. ст., ng 1,5675,Prepared according to Method B from 0.1 g of Na in 7 ml of methanol, 7.4 g (0.055 g-mol) of trimethylsilylethyl mercapt} 1a and 4.4 g (0.043 g-mol of phenylacetylene. 5 g (49%) are isolated trimethylsilyl-2-phenylethylvinyl sulfide with a bale of 137-138 0 / 2-3 mm Hg, ng 1.5675,
df 0,9725.df 0.9725.
Найдено, %: С 65,70; Н 8,28; S 13,14; Si 12,28.Found,%: C 65.70; H 8.28; S 13.14; Si 12.28.
Ci3H2oSSi.Ci3H2oSSi.
Вычислено, %: С 66,03; П 8,52; S 13,36; Si 11,88.Calculated,%: C 66.03; P 8.52; S 13.36; Si 11.88.
Пример 3. 2-Трипропилсилил-2-фенилэтилвинилсульфид .Example 3. 2-Tripropylsilyl-2-phenylethylvinyl sulfide.
Получают по методу «в из 2,2 г (0,04 г-моль) КОП в 15 мл метанола, 8,2 гReceive by the method of 2.2 g (0.04 g-mol) KOP in 15 ml of methanol, 8.2 g
трипропилсилилэтилтиоацетата, 2,5 г фенилацетилена . Выдел ют 5 г (53.8), продукта с т. кии. 158-159,5°С/4-10-2 мм рт. ст., -пtripropylsilylethylthioacetate, 2.5 g of phenylacetylene. 5 g (53.8) of the product with rms was isolated. 158-159.5 ° C / 4-10-2 mm Hg. Art., -p
1,5425, df 0,9431. 1.5425, df 0.9431.
Пайдено, %: С 70,82; П 10,03; S 10,48; Si 8,85. CigHaaSSi.Paydeno,%: C, 70.82; P 10.03; S 10.48; Si 8.85. CigHaaSSi.
Вычислено, %: С 71,13; И 10,05; S 9,9); Si 8,75.Calculated,%: C 71.13; And 10.05; S 9.9); Si 8.75.
Предмет изобретени Subject invention
Claims (3)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU285924A1 true SU285924A1 (en) |
Family
ID=
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SU1230465A3 (en) | Method of producing organic sulfides | |
| SU285924A1 (en) | METHOD OF OBTAINING 2- (TRIALKILSILIL) ETHYL-2'-PHENYLVINYLSULFIDES | |
| JP6866316B2 (en) | Substituted imidazolium sulfuran and their use | |
| SU191559A1 (en) | METHOD FOR PRODUCING SILICON ORGANIC ETHINYLVINYL SULPHIDES | |
| EP0430808B1 (en) | Dihydropyran derivatives, their processes of preparation and their use | |
| SU362839A1 (en) | USSR Academy of Sciences | |
| SU415258A1 (en) | METHOD OF OBTAINING DIVINYLSULFIDES | |
| SU256751A1 (en) | METHOD OF OBTAINING DIETHYL ETHER OF p-CHLORETETRAHYDROFURYL-p-CHLOROLLYMALONIC ACID | |
| SU255265A1 (en) | METHOD OF OBTAINING 1,4-PHENYLENE-BIS- [ALKYL (ARYL) CHLOR- | |
| SU203664A1 (en) | Method of producing monovinyl aceticene ethers containing two atom of oxygen in the molecule | |
| JP3174576B2 (en) | Method for producing 3- (S) -furan derivative | |
| SU170967A1 (en) | METHOD OF OBTAINING TRICHLOROMETHYL-2-CHLORALKYL DISISLIPIDES | |
| SU250122A1 (en) | METHOD FOR OBTAINING COMPLEX BRANCHED ALKYLARYL ETHYL ETHYLENE GLYCOL | |
| FR2720395A1 (en) | New compounds from the benzoheterocycles family. | |
| Braga et al. | Synthesis of Dibromo-Vinyl Chalcogenides | |
| SU275063A1 (en) | WAY OF OBTAINING a-BROMACRYLONITRILE | |
| SU891655A1 (en) | Method of preparing bis-(alkoxymethyl)-selenides | |
| SU191543A1 (en) | METHOD OF OBTAINING p-ARILTHIOETHYLMERCAPTANS | |
| SU187014A1 (en) | METHOD FOR OBTAINING PHENOXYBICYCLO ESTERS | |
| SU469691A1 (en) | Method for producing alkylthioalkylmalonic esters | |
| SU423802A1 (en) | METHOD OF OBTAINING 0,0-DIALKYL-5-p-BROMETYL DYTHIOPHOSPHATES | |
| SU292982A1 (en) | USSR Academy of Sciences | |
| RU2284320C1 (en) | Method for preparing vinyl sulfides | |
| SU289086A1 (en) | METHOD OF OBTAINING DIARYLESULFIDES | |
| US3897473A (en) | Mercapto and sulfide containing dienoic thioacid esters |