New process gives good yields of anilinosilane compounds that can be readily isolated in a high state of purity. S-collidine is used as an HCl acceptor. Silane compounds can be melt-condensed with aromatic diols to provide high molecular weight polyaryloxysilane materials that are of importance in polymer technology

Dunnavant, W. R.

Markle, R. A.

English

NASA Technical Reports Server

NASA TECH BRIEF 
F-1
April 1970	 Brief 70-10105 
NASA Tech Briefs announce new technology derived from the U.S. space program. They are issued to encourage commercial 
application. Tech-Briefs are available on a subscription basis from the Clearinghouse for Federal Scientific and Technical 
Information, Springfield, Virginia 22151. Requests for individual copies or questions relating to the Tech Brief program may 
be directed to the Technology Utilization Division, NASA, Code UT, Washington, D.C. 20546. 
Improved Process for Synthesizing Anilinosilane Compounds 
.
A new process has been developed for pro .ducing 
good yields of anilinosilane compounds that can be 
readily isolated in a high state of purity. A variety of 
di- and tri-anilinosilanes, including diphenyl-, 
dimethyl-, methyiphenyl-, methylvinyl-,. phenylvinyl-, 
and methylallyl-dianilinosilanes and trianilinophenyl-
silane, were successfully prepared by this process. 
The key to the process is the use of s-collidine (2,4,6-
trimethylpyridirie) as an HCI acceptor. The silane 
compounds are of interest in that they can be melt-
condensed with aromatic diols to provide a wide 
variety of high molecular weight polyaryloxysilane 
materials that are of potential importance in polymer 
technology. 
Previously . reported syntheses of anilinosilanes 
require the condensation of the corresponding chloro-
silane with excess aniline, which functions as an HCI 
acceptor. These reactions are reversible and provide 
generally low, nonreproducible product yields which 
are difficult or impossible to isolate in the pure state. 
In the new process, it is believed that s-collidine plays 
a unique role as an HCI acceptor in that it is a stronger 
base than the aniline, with which it competes, and 
because it apparently forms sterically hindered HCl 
salts that cannot reversibly interact with the anilino-
silanes. As a result, the reaction mixtures are rela-
tively free from side products, greatly facilitating 
isolation of highly pure anilinosilanes by crystalliza-
tion and/or vacuum distillation. These compounds
have been prepared in yields ranging from 50 to 90 
percent and in a high state of purity as determined 
from their melting and boiling points and elemental 
analysis. 
The new process is carried out by condensing 
stoichiometric amounts of aniline with the appropriate 
chlorosilane in tetrahydrofuran in the presence of 
s-collidine. The insoluble s-collidine hydrochloride 
salts are removed from the reaction mixture by filtra-
tion, the filtrates are concentrated, and the pure 
anilinosilanes are isolated from the concentrates by 
either crystallization or vacuum distillation. 
Note: 
No further documentation is available. Inquiries may 
be directed to: 
Technology Utilization Officer 
Marshall Space Flight Center 
Huntsville, Alabama 35812 
Reference: B70-10105 
Patent status: 
Inquiries about obtaining rights for the commercial 
use of this invention may be made to NASA, Code 
GP, Washington, D.C. 20546. 
Source: W. R. Dunnavant and R. A. Markle of

Battelle Memorial Institute

under contract to

Marshall Space Flight Center

(MFS-14948) 
Category 04 
This document was prepared under the sponsorship of the National 
Aeronautics and Space Administration. Neither the United States 
Government nor any person acting on behalf of.the United States
Government assumes any liability resulting from the use of the 
information contained in this document, or warrants that such use 
will be free from privately owned-rights.
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Improved process for synthesizing anilinosilane compounds

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