SU323006A1 - METHOD OF OBTAINING p-AMINOETHILSILANES WITH FUNCTIONAL AMINOGROUNDS AT ATOMACRUMINIA - Google Patents
METHOD OF OBTAINING p-AMINOETHILSILANES WITH FUNCTIONAL AMINOGROUNDS AT ATOMACRUMINIAInfo
- Publication number
- SU323006A1 SU323006A1 SU1430195A SU1430195A SU323006A1 SU 323006 A1 SU323006 A1 SU 323006A1 SU 1430195 A SU1430195 A SU 1430195A SU 1430195 A SU1430195 A SU 1430195A SU 323006 A1 SU323006 A1 SU 323006A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- functional
- mol
- atomacruminia
- aminogrounds
- aminoethilsilanes
- Prior art date
Links
- 125000003277 amino group Chemical group 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- UKRDPEFKFJNXQM-UHFFFAOYSA-N Vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000003857 carboxamides Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000002194 synthesizing Effects 0.000 description 2
- OCTHFCZOQHUXHH-UHFFFAOYSA-N C(C)N(CC)[SiH2]C=C(C)C Chemical compound C(C)N(CC)[SiH2]C=C(C)C OCTHFCZOQHUXHH-UHFFFAOYSA-N 0.000 description 1
- YYUHOKNMHJLNPZ-UHFFFAOYSA-N C(C)[SiH2]NCCC Chemical compound C(C)[SiH2]NCCC YYUHOKNMHJLNPZ-UHFFFAOYSA-N 0.000 description 1
- HCZXSTHBEIEIOY-UHFFFAOYSA-N CC[SiH2]N(CC)CC Chemical compound CC[SiH2]N(CC)CC HCZXSTHBEIEIOY-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N Diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- DYEJUGFQWAGGDF-UHFFFAOYSA-N N-(diethylamino-ethenyl-methylsilyl)-N-ethylethanamine Chemical compound CCN(CC)[Si](C)(C=C)N(CC)CC DYEJUGFQWAGGDF-UHFFFAOYSA-N 0.000 description 1
- LXXSWZYRKAQQDI-UHFFFAOYSA-N N-ethyl-N-silylethanamine Chemical compound CCN([SiH3])CC LXXSWZYRKAQQDI-UHFFFAOYSA-N 0.000 description 1
- VHGQQWYZFYJXFB-UHFFFAOYSA-N NC=C[SiH3] Chemical compound NC=C[SiH3] VHGQQWYZFYJXFB-UHFFFAOYSA-N 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N Propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N Sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- -1 aliphatic amines Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical class 0.000 description 1
- 238000007098 aminolysis reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Description
Изобретение относитс к области органической химии, а именно к химии кремнийорганических соединений.This invention relates to the field of organic chemistry, namely the chemistry of organosilicon compounds.
р-аминоэтилсиланы с функциональными аминогруппами у атома кремни общей формулыp-aminoethylsilanes with functional amino groups at the silicon atom of the general formula
/ /
OnRs-nSiCHaCHzNOnRs-nSiCHaCHzN
г/g /
где Ф -NV . R - алкил, представл ют собой вещества, которые до сих пор не описаны.where f is -NV. R-alkyl, are substances that have not yet been described.
Известен способ получени р-аминоэтилсиланов по Проберу реакцией присоединени аминов к алкоксивинилсиланам в присутствии амида натри , который не ведет к однозначному образованию алкоксиаминоэтилсиланов за счет одновременного протекани реакции замещени алкоксигрупп на аминогруппу.A known method for producing p-aminoethylsilanes by Probe by the reaction of adding amines to alkoxyvinylsilanes in the presence of sodium amide, which does not lead to the unambiguous formation of alkoxyaminoethylsilanes due to the simultaneous reaction of the substitution of alkoxy groups for the amino group.
Цель изобретени - разработка способа получени р-аминоэтилсиланов с функциональными аминогруппами у атома кремни .The purpose of the invention is to develop a method for producing p-aminoethylsilanes with functional amino groups on a silicon atom.
Предлагаемые соединени получают реакцией присоединени алифатических аминов (первичных и вторичных) к винилсиланам общей формулыThe compounds according to the invention are prepared by the addition of aliphatic amines (primary and secondary) to vinyl silanes of the general formula
R// R //
алкил, O -N; Ralkyl, O —N; R
алкилы, n l-3.alkyls, n l-3.
Катализаторами реакции вл ютс органические амиды, которые могут быть получены реакцией аминолиза аминов литийалкилами. Проведение реакции в пол рных растворител х позвол ет сократить врем реакции иThe catalysts for the reaction are organic amides, which can be obtained by reacting the aminolysis of amines with lithium alkyls. Carrying out the reaction in polar solvents can shorten the reaction time and
увеличить выходы продуктов присоединени . Реакци присоединени проводитс в интервале температур 20-100°С, соотношени реагентов винилсилан : амин :бутиллитий 1 : 1,2 : : 0,15- 1:2: 0,3. Максимальные выходы продуктов присоединени (первичные амины 20-40%, вторичные амины 60-80% получены при соотношении реагентов 1 : 2 :0,3).increase yields of accession products. The addition reaction is carried out in the temperature range of 20-100 ° C, the ratio of reactants is vinyl silane: amine: butyl lithium 1: 1.2:: 0.15-1: 2: 0.3. Maximum yields of addition products (primary amines 20–40%, secondary amines 60–80% obtained with a reagent ratio of 1: 2: 0.3).
Благодар присутствию функциональных аминогрупп возможно получение разнообразных производных р-аминоэтилсиланов, различие в реакционной способности этих функциональных групп у атома кремни и в углеводородном радикале открывает возможность проведени селективных реакций по одному изDue to the presence of functional amino groups, it is possible to obtain various derivatives of p-aminoethylsilanes, the difference in the reactivity of these functional groups at the silicon atom and in the hydrocarbon radical opens up the possibility of conducting selective reactions in one of
реакционных центров и, несомненно, иметь практическое значение.reactionary centers and undoubtedly have practical significance.
(0,0242 моль) литийбутила концентрацией 7,5 моль/мл в токе инертного газа при температуре -30°С. После получасового кип чени дл образовани органического амида смесь вновь охлаждают и прибавл ют 19,1 г (0,089 моль) метилвинил-бис(диэтиламино )силана.(0.0242 mol) lithium butyl concentration of 7.5 mol / ml in a stream of inert gas at -30 ° C. After boiling for half an hour to form the organic amide, the mixture is cooled again and 19.1 g (0.089 mol) of methyl vinyl bis (diethylamino) silane is added.
Реакционную смесь кип т т 30 час, затем фильт)уют и фракционируют.The reaction mixture was boiled for 30 hours, then filtered and cozy and fractionated.
При разгонке выдел ют 10,2 г (42%) фракцип с т. кип. 105-106°С/2 мм; п 1,4557; df 0,8443; Si 9,42%; N 15,47%, 15,72%.During the distillation, 10.2 g (42%) of the fraction with m.p. 105-106 ° C / 2 mm; P 1,4557; df 0.8443; Si 9.42%; N 15.47%, 15.72%.
Пример 2. Синтез диэтилдиэтиламино-р (пропиламино) этилсилана.Example 2. Synthesis of diethyldiethylamino-p (propylamino) ethylsilane.
В услови х, аналогичных примеру 1, изUnder conditions similar to Example 1, from
5.3г (0,865 моль) пропиламина и И г (0,0595 моль) диэтилБинилдиэтиламиносилана в присутствии 10 мл (0,015 моль) литийбутила концентрацией 15-10 моль/мл получают 5.3 g (0.865 mol) of propylamine and And g (0.0595 mol) of diethylbenyl diethylaminosilane in the presence of 10 ml (0.015 mol) of lithium butyl with a concentration of 15-10 mol / ml is obtained
5.4г (37%) фракции с т. кип. 105- 107°С/4 мм; п 1.4516; df 0,8415; Si 11,66%; N 10,7%.5.4g (37%) fraction with m. Kip. 105 - 107 ° C / 4 mm; P 1.4516; df 0.8415; Si 11.66%; N 10.7%.
Пример 3. Синтез диметилдиэтиламино-р (диэтиламино)-этилсилана.Example 3. Synthesis of dimethyldiethylamino-p (diethylamino) ethylsilane.
В услови х, аналогичных описанным в примере 1, из 10,7 г (0,147 моль) диэтиламина и 11,5 S (0,0735 моль) диметилвинилдиэтиламиносилана в присутствии 29,4 мл (0,0205 моль) литийбутила концентрацией 7,5-10- моль/мл получают 12,9 г (77%) фракции с т. кип.Under conditions similar to those described in example 1, from 10.7 g (0.147 mol) of diethylamine and 11.5 S (0.0735 mol) of dimethylvinyl diethylaminosilane in the presence of 29.4 ml (0.0205 mol) of lithium butyl in a concentration of 7.5- 10 mol / ml gives 12.9 g (77%) of the fraction with m.p.
rf° 1,4454; df 0,8322:rf ° 1,4454; df 0.8322:
118-120° С/20 мм; Si 12,33%; N 12,13%.118-120 ° C / 20 mm; Si 12.33%; N 12.13%.
Предмет изобретени Subject invention
Способ получени р-аминоэтилсиланов с функциональными аминогруппами у атома кремни , отличающийс тем, что аминовинилсилан подвергают взаимодействию с первичным или вторичным амином в присутствии в качестве катализатора продукта взаимодейству буткллити с исходным амином.A process for the preparation of p-aminoethylsilanes with functional amino groups at the silicon atom, characterized in that the aminovinylsilane is reacted with a primary or secondary amine in the presence of a product as a catalyst and interacts with butclity with the starting amine.
Publications (1)
Publication Number | Publication Date |
---|---|
SU323006A1 true SU323006A1 (en) |
Family
ID=
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
RU2705401C2 (en) * | 2015-02-18 | 2019-11-07 | ТРИНСЕО ЮРОП ГмбХ | Multivinylaminosilanes as branching agents for functionalised elastomeric polymers |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
RU2705401C2 (en) * | 2015-02-18 | 2019-11-07 | ТРИНСЕО ЮРОП ГмбХ | Multivinylaminosilanes as branching agents for functionalised elastomeric polymers |
US10858377B2 (en) | 2015-02-18 | 2020-12-08 | Trinseo Europe Gmbh | Multivinylaminosilanes as branching agents for functionalized elastomeric polymers |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CA1218996A (en) | Maleated siloxane derivatives | |
Speier et al. | Syntheses of (3-aminoalkyl) silicon compounds | |
JP5236731B2 (en) | Method for producing aminoorganosilane | |
JP4560053B2 (en) | Prescribed method for producing a silicon compound having a fluoroalkyl group by hydrosilylation | |
TW201602124A (en) | Preparation of silazane compound | |
KR101152249B1 (en) | Method for producing trimethylsilyl azide | |
SU323006A1 (en) | METHOD OF OBTAINING p-AMINOETHILSILANES WITH FUNCTIONAL AMINOGROUNDS AT ATOMACRUMINIA | |
US9181284B2 (en) | Method for producing aminoalkylalkoxysilanes | |
JP5519006B2 (en) | Method for producing aminoorganosilane | |
CA2113768C (en) | Preparation of trialkylsilyl nitrile | |
JPH03197486A (en) | Production of organosiloxane having alkoxysilyl group | |
JP6947084B2 (en) | Method for Producing Imine Structure-Containing Organoxysilane Compound | |
Kitamura et al. | Synthesis of α-arylcarboxylic acid amides from silyl enol ether via migratory amidation with 2-Azido-1, 3-dimethylimidazolinium hexafluorophosphate | |
JP6866316B2 (en) | Substituted imidazolium sulfuran and their use | |
SU319601A1 (en) | UNIONAL METHOD OF OBTAINING p-AMINOETHILSILANOV 1 "- ^ '^^^ THO-TYNESYAD? S | |
JP4257515B2 (en) | Process for producing 1,3-bis (3-aminopropyl) -1,1,3,3-tetramethyldisiloxane | |
RU2724877C1 (en) | Method of producing tetraalkynylsilanes | |
KR101242397B1 (en) | Preparation of an aminoaryl-containing organosilicon compound and methods of preparaing intermediates used in its preparation | |
Schmohl et al. | Head‐to‐Head versus Head‐to‐Tail Dimerizations of Transient Silenes–The Solvent‐Dependent Regiospecifity of the Dimerization of 2‐(2‐Methoxyphenyl)‐1, 1‐bis (trimethylsilyl) silene | |
SU237893A1 (en) | METHOD OF OBTAINING BIS- (ALKOXISYLIL) CARBORANES | |
US6291716B1 (en) | Ortho-alkylation method of aromatic ketones | |
Шатирова et al. | SYNTHESIS AND PROPERTIES OF CYCLOHEXYL AMINES OF PROPARGYL SERIES | |
SU280480A1 (en) | Method of producing alkyl (aryl) aminosilanes with a cyclopentadienyl radical in atomic silicon | |
SU288701A1 (en) | METHOD FOR OBTAINING ORGANO-SILO ACYANALKYL COMPOUNDS | |
SU158879A1 (en) |