By Eugene. Rochow

An creation to the CHEMISTRY of the SILICONES via EUGENE G. ROCHOW study Laboratory, common electrical corporation long island JOHN WILEY SONS, INC. LONDON CHAPMAN corridor, constrained COPYRIGHT, 1946 by way of EUGENE G. ROCHOW AU Rights Reserved This publication or any half thereof must never be reproduced in any shape with no the written permission of the writer. moment PRINTING, MARCH, 1947 published within the united states To P. G. F. PREFACE The natural compounds of silicon, that have been the topic of many scholarly researches in past times eighty years, eventually convey promise of rising from the laboratory and discovering a spot in undefined. An knowing of the habit of organosilicon fabrics is critical to their clever use and, inasmuch because the chemistry of those components often isn't really taken care of in our textbooks, it's attainable compact but accomplished survey of our current wisdom during this box will be of provider to chemists, engineers, and business designers. This quantity has simply the sort of goal. the 1st few chapters assessment the silanes and their derivatives in a few aspect, which will supply an figuring out of the basic chemistry of the nonsilicate com kilos of silicon. The later chapters emphasize the silicone polymers that have completed advertisement value and care for the tools for his or her education, their chemical and actual homes, and their attainable usas. The strategies on hand for large-scale creation are taken care of individually, and a overview of tools of study is incorporated. so as to not burden the textual content with definitions and reasons of nomenclature which would already be universal to a few readers, an intensive thesaurus of phrases is appended. An exhaustive assessment of the literature on natural compounds of sili con can't rather well be integrated in a quantity meant for the non expert. even though, many references are supplied, and tables of many of the recognized compounds and their houses are incorporated within the acceptable chapters. The reader will locate accomplished studies of guides in neighbors Textbook of Inorganic Chemistry, quantity eleven, half 2 Krause and von Grossed Chemie der Metallorgamschen Ver bindungen, Dolgows Chemistry of the Silica-Organic Compounds, and Bygdens Silizium als Vertreter des Kohlenstoffs organischen Verbindun gen. a newer and extra entire compilation of the literature on natural compounds of silicon will be welcomed by way of each investigator within the box. considering this paintings provides some extent of view instead of an uncritical compilation of released truth, the writer needs to suppose whole responsi bility for the reviews expressed. even though, he's significantly indebted to his coworkers iu the learn laboratory of the final Electriq Com vii viii PREFACE pany for precious recommendation and criticisms. In a bigger feel this paintings is the results of a long time of universal activity in a best box of analysis. CONTENTS bankruptcy web page 1. the straightforward COVALENT COMPOUNDS OF SILICON 1 advent 1 Chemical habit of the point three The Hydrides four The Halides nine The Esters or Ethers 12 Index of consultant Compounds sixteen 2. THE ORGANOSILICON MONOMERS 18 equipment for Carbon-Silicon Bonds 19 The Alkyls 30 The Alkylsilanes 32 The Alkylhalosilanes 33 The Alkylalkoxysilanes 37 Index of consultant Compounds 39 three. sorts of ORGANOSI LICON POLYMERS forty five Silicon Chains forty five Silicon-Carbon Chains forty six Siloxane Chains forty nine Siloxane Networks fifty three Index of consultant Compounds fifty eight four. houses OF the explicit SILICONS POLYMERS 60 Alkyl Silicones sixty two Methyl Silicone Oil sixty four Methyl Silicone Resins 70 Silicone Rubber seventy two Ethyl Silicone Resins seventy three different Alkyl Silicone Resins seventy four Aryl Silicones seventy seven Alkyl-Aryl Silicones eighty five. WATER-REPELLENT movies FROM ORGANOSILICON fabrics eighty three response of Methylchlorosilanes eighty three makes use of eighty five 6. TECHNICAL points OF SILICONES 89 The Intermediates ninety The Grignard approach ninety one The Direct strategy ninety six Processing one hundred and one Toxicity 103 destiny enlargement 104 ix CONTENTS bankruptcy 7...

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The use of a separately prepared sodium alkyl in this way provides the same degree of control as in a Grignard synthesis, and the reactions indeed action ensues. are very similar. in the same way. Organolithium compounds probably could be used When Victhe the of separate preparation Grignard developed organomagnesium halides as reagents, he not only opened a wide field of 3. SUBSTITUTION BY ORGANOMAGNESIUM COMPOUNDS. tor first synthesis in organic chemistry but also gave a great impetus to organosilicon chemistry.

Patent 2 238 669 to R. H. Wiley. ^Soshestvenskaya, J. Gen. Chem. USSR 8, 294 (1938); ibid. 10, 1689 (1940); Manulkin and Yakubova, J. Gen. Chem. USSR 10, 1300 (1940). 31 Kipping and Blackburn, /. Chem. Soc. 1932, 2200. 82 Polis, Ber. 18, 1540 (1885). 33 Kipping and Lloyd, /. Chem. Soc. 79, 449 (1901). 34 Smith and Kipping, J. Chem. Soc. 101, 2553 (1912). ; THE ORGANOSILICON MONOMEK8 32 (as in the preparation of tripropylallylsilane from silicon tetrapropyl), but most have been made by the successive replacement of the chlorine in silicon tetrachloride with different radicals supplied by Grignard reagents, as in these examples: + C 6H 5 MgBr = C 6H 5SiCl3 + MgBrCl C 6H 5SiCl3 + C 2 H 5 MgBr = (C 6 H 5 (C 2 H 6 )SiCl 2 + MgBrCl (C 6H 5 )(C 2H 5 )SiCl 2 + C 3 H 7 MgBr = (C 6H 5 )(C 2 H 6 )(C 3 H 7 )SiCl + MgBrCl (C 6H 5 )(C 2 H 5 )(C 3 H 7 )SiCl + CH 3 MgBr = (C 6H 5 )(C 2 H 5 )(C 3 H 7 )(CH 3 )Si + MgBrCl SiCU ) A mixed alkyls, together with their physical propmethods of preparation, and literature references, is given in 35 Those with four different groups represent Krause and von Grpsse.

16 Hyde and DeLong, J. Am. Chem. Soc. 63, 1194 (1941). "Kipping, /. Chem. Soc. 101, 2125 (1912). * See Chapter 1. SILOXANE NETWORKS 53 SILOXANE NETWORKS Whether in cyclic form or in straight chains terminated by hydroxyl or trimethylsilyl groups, the organosiloxane polymers so far considered have consisted principally of repetitions of the unit SiO R2 Now necessary to consider another concept, that of the cross linking of siloxane chains and rings. Cross linking is a means of further increasthe molecular average ing weight of the polymer, and at the same time it is it also serves to establish a three-dimeasional rigidity and decreased One way network of increased solubility.

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