SU311919A1 - METHOD FOR OBTAINING SILICON ORGANIC BICYCLIC MONOMERS - Google Patents
METHOD FOR OBTAINING SILICON ORGANIC BICYCLIC MONOMERSInfo
- Publication number
- SU311919A1 SU311919A1 SU1353689A SU1353689A SU311919A1 SU 311919 A1 SU311919 A1 SU 311919A1 SU 1353689 A SU1353689 A SU 1353689A SU 1353689 A SU1353689 A SU 1353689A SU 311919 A1 SU311919 A1 SU 311919A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- silicon organic
- obtaining silicon
- mol
- bicyclic monomers
- organic bicyclic
- Prior art date
Links
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title 1
- 229910052710 silicon Inorganic materials 0.000 title 1
- 239000010703 silicon Substances 0.000 title 1
- 239000007788 liquid Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 2
- -1 bicyclic organosilicon compounds Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N 2-methyl-2-propenoic acid methyl ester Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- RPXRWIYUJNMJOZ-UHFFFAOYSA-N C1(C=CC=C1)C[SiH](Cl)Cl Chemical compound C1(C=CC=C1)C[SiH](Cl)Cl RPXRWIYUJNMJOZ-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- AIRILDQHJRAOBJ-UHFFFAOYSA-N cyclopenta-2,4-dien-1-ylsilane Chemical class [SiH3]C1C=CC=C1 AIRILDQHJRAOBJ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229910052736 halogen Chemical group 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 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
- 239000003960 organic solvent Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- NMGNJWORLGLLHQ-UHFFFAOYSA-M sulcofuron-sodium Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1NC(=O)NC1=CC=C(Cl)C(Cl)=C1 NMGNJWORLGLLHQ-UHFFFAOYSA-M 0.000 description 1
- MQFRTBNPKINELL-UHFFFAOYSA-N trichloro(cyclopenta-2,4-dien-1-yl)silane Chemical compound Cl[Si](Cl)(Cl)C1C=CC=C1 MQFRTBNPKINELL-UHFFFAOYSA-N 0.000 description 1
Description
Изобретение относитс к получению карбофункциональных бициклических кремнийорганических соединений, которые могут быть использованы дл синтеза кремнийсодержащих полимеров.This invention relates to the production of carbo-functional bicyclic organosilicon compounds that can be used to synthesize silicon-containing polymers.
В основном авт. св. № 159520 описан способ полученн кре.мнийорганических бицнклических мономеров конденсацией замещенных циклопентадиенилсиланов общей формулыBasically auth. St. No. 159520 describes a process for preparing organo-organic bicenclic monomers by condensing substituted cyclopentadienylsilanes of the general formula
CoHsSiXsCoHsSiXs
где X - алкил, арил или галоид, с непредельными соединени ми тинаwhere X is alkyl, aryl or halogen, with unsaturated compounds mitin
CH2 CRRCH2 CRR
где R - CN, COOAlK, СОА1к, Hal, NOs и др., R - водород, алкил или галоид.where R is CN, COOAlK, COA1k, Hal, NOs, etc., R is hydrogen, alkyl or halo.
Целью изобретени вл етс упрощение процесса. Это достигаетс проведением процесса при постепенном повыщении температуры реакционной смеси от 80 до 140°С и при атмосферном давлении. По сравнению с известным снособом в несколько раз сокращаетс продолжительность процесса и значительно упрощаетс технологическое офор.мление.The aim of the invention is to simplify the process. This is achieved by carrying out the process with a gradual increase in the temperature of the reaction mixture from 80 to 140 ° C and at atmospheric pressure. In comparison with the known method, the duration of the process is shortened several times and the technological arrangement is greatly simplified.
Конденсацию можно проводить как в среде инертных органических растворителей, например толуола, ксилола, так и без них. Выход целевых продуктов до 85%.Condensation can be carried out both in inert organic solvents, for example toluene, xylene, and without them. The yield of target products is up to 85%.
Пример 1. 2-Цпано-4-трихлорсилилбицикло- (2,2,1) -гептеп-5.Example 1. 2-Cpano-4-trichlorosilylbicyclo- (2,2,1) -teptep-5.
В колбу, снабженную обратным холодильником , помещают смесь, состо щую из 159,6 г (0,8 моль) свежеперегнанного циклопентадиенилтрихлорсилана и 46,6 г (0,88 моль акрнлонитрила . Смесь нагревают до 80°С, затем температуру реакционной смеси повыщают до 140°С равномерно в 3 час. Целевой продукт выдел ют разгонкой в вакууме . Получают 175,3 г (85% от теоретического ) бесцветной жидкости с т. кип. 130- 131 °С (6 мм рт. ст.); ng 1,5075; df 1,3239;In a flask equipped with a reflux condenser, a mixture of 159.6 g (0.8 mol) of freshly distilled cyclopentadienyltrichlorosilane and 46.6 g (0.88 mol of acrnlonitrile) is placed. The mixture is heated to 80 ° C, then the temperature of the reaction mixture is raised to 140 ° C evenly at 3 o'clock The target product is isolated by distillation in vacuum to give 175.3 g (85% of theoretical) of a colorless liquid with a boil of 130-131 ° C (6 mmHg); ng 1 , 5075; df 1,3239;
MRo 56,82.MRo 56.82.
Пайдено, %: Cl 41,92; Si 11.31; N 5,60.Paideno,%: Cl 41.92; Si 11.31; N 5.60.
CsHsClaNSi.CsHsClaNSi.
Вычислено, %: Cl 42,10; Si 11,12; N 5,45. -MRo 56,43.Calculated,%: Cl 42.10; Si 11.12; N 5.45. -MRo 56,43.
П p и M e p 2. 2-Л1етилкарбокси-4-этилдихлорсилилбицикло- (2,2,1) -гептен-5.P p and M e p 2. 2-L1-methylcarboxy-4-ethyldichlorosilyl-bicyclo- (2,2,1) -hepten-5.
В услови х примера 1 из 96,5 г (0,5 моль) циклопентадиенмлэтилдихлорсплана и 47,3 г (0,55 моль) мегплакрилата получают 113 г (81% от теоретического) желтоватой жидкости с т. кип. 134-135°С (7 мм рт. ст.); Under the conditions of example 1, out of 96.5 g (0.5 mol) of cyclopentadiene-methyl dichloroplane and 47.3 g (0.55 mol) of megaplacrylate, 113 g (81% of the theoretical) of a yellowish liquid with m.p. 134-135 ° C (7 mm Hg. Art.);
2020
n 1,4912; d 1,1800; MRo 68,55. Пайдено, Cl 25,10; Si 10,19. CiinieOaCbSi. Вычислено, %: Cl 25,40; Si 10,06. MRn 67,99.n 1.4912; d 1.1800; MRo 68.55. Paideno, Cl 25.10; Si 10.19. CiinieOaCbSi. Calculated,%: Cl 25.40; Si 10.06. MRn 67.99.
Пример 3. 2-Метил-2-меткарбокси-4метилдихлорсилилбицикло- (2,2,1) -гептен-5.Example 3. 2-Methyl-2-metcarboxy-4methyldichlorosilyl-bicyclo- (2,2,1) -hepten-5.
В услови х примера 1 из 179,2 г (1 моль циклопентадиенилметилдихлорсилана и 105 г (1,05 моль) метилметакрилата получают 226 г (81% от теоретического) желтоватой жидкости с т. кип. 137-138°С (13 мм рт. ст.}; 1,4880; df 1,1758; MRo 68,43.Under the conditions of example 1, out of 179.2 g (1 mol of cyclopentadienylmethyldichlorosilane and 105 g (1.05 mol) of methyl methacrylate, 226 g (81% of theoretical) of a yellowish liquid with a boil. 137-138 ° C (13 mm Hg) are obtained. }; 1.4880; df 1.1758; MRo 68.43.
Найдено, %: С1 25,20; Si 10,29. CiiHieO2Cl2Si.Found,%: C1 25.20; Si 10.29. CiiHieO2Cl2Si.
Вычислено, %: С1 25,39; Si 10,06. MRr 68,19.Calculated,%: C1 25.39; Si 10.06. MRr 68.19.
Пример 4. 2-Циано-4-пропилдихлорсилилбицикло- (2,2,1) -гептен-5.Example 4. 2-Cyano-4-propyldichlorosilyl-bicyclo- (2,2,1) -hepten-5.
Смесь 62,1 г (0,3 моль циклопентадиенилпропилдихлорсилана , 17,5 з (0,33 моль акрилонитрила и 50 мл ксилола кип т т в колбе с обратным холодильником в течение 3 час.A mixture of 62.1 g (0.3 mol of cyclopentadienyl propyl dichlorosilane, 17.5 s (0.33 mol of acrylonitrile and 50 ml of xylene) is refluxed for 3 hours.
Ксилол отгон ют, а остаток разгон ют в вакууме . Получают 65,5 г (84%) бесцветной жидкости с т. кип. 145-146°С (4 мм рт. ст.}; п|о 1,5000; df 1,1485; MRn 66,12The xylene is distilled off and the residue is distilled in vacuo. Get 65.5 g (84%) of a colorless liquid with m. Kip. 145-146 ° С (4 mm of mercury); n | about 1,5000; df 1,1485; MRn 66,12
Найдено, %: С1 26,89; Si 10,98; N 5,24. CiiHi5Cl2Si.Found,%: C1 26.89; Si 10.98; N 5.24. CiiHi5Cl2Si.
Вычислено, %: С 27,25; Si 10,79; N 5,37. MRo 66,15.Calculated,%: C 27.25; Si 10.79; N 5.37. MRo 66.15.
Предмет изобретени Subject invention
Способ получени кремнийорганических бициклических мономеров по авт. св. № 159520, отличающийс тем, что, с целью упрощени процесса, его провод т при постепенном повышении температуры реакционной среды от 80 до 140°С и при атмосферном давлении.The method of obtaining silicone bicyclic monomers according to ed. St. No. 159520, characterized in that, in order to simplify the process, it is carried out with a gradual increase in the temperature of the reaction medium from 80 to 140 ° C and at atmospheric pressure.
Publications (1)
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| SU311919A1 true SU311919A1 (en) |
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