cas 541-02-6, Decamethylcyclopentasiloxane

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Tris(pentafluorophenyl)borane-Catalyzed Reactions of Siloxanes: A Combined Experimental and Computational Study
The reaction of 1,1,3,3-tetramethyldisiloxane with 1-octene as a model reaction of silicone curing catalyzed by B(C6F5)3 resulted in the redistribution of the disiloxane into dimethylsilane and cyclic oligosiloxanes, and the subsequent hydrosilylation reaction of dimethylsilane afforded dimethyldioctylsilane. To obtain insights into the reaction mechanism and possibility alter the reaction pathway to favor the hydrosilylation over the redistribution, mechanistic analysis of the reaction between a hydrosiloxane (1,1,3,3-tetramethyldisiloxane, silox-H) and a vinylsiloxane (1,1,3,3-tetramethyl-1,3-divinyldisiloxane, silox-vin) in the presence of B(C6F5)3 was performed through density functional theory calculations. The results of the calculations indicate that the activation of a Si–H bond in silox-H by B(C6F5)3 initiates the reaction to form the B(C6F5)3–silox-H complex with a Lewis acidic silicon atom and a hydridic hydrogen atom. The B(C6F5)3–silox-H complex can undergo two different reaction pathways, that is, trisiloxane formation and the hydrosilylation of silox-vin by silox-H. The trisiloxane formation involves trisilyloxonium ions as intermediates and can lead to either the homotrisiloxane of silox-H or a mixed trisiloxane of silox-H and silox-vin. The energetics of the reaction pathways predict the preference of trisiloxane formation over hydrosilylation, and the fine tuning of the steric and electronic natures of the substrates could alter the thermodynamic and kinetic favorability.
Mathew, Jomon,Eguchi, Katsuya,Nakajima, Yumiko,Sato, Kazuhiko,Shimada, Shigeru,Choe, Yoong-Kee
p. 4922 - 4927
(2017)
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Unusual Competition of Intermolecular vs. Intramolecular Reactions. Kinetics of the Condensation of Decamethylpentasiloxane-1,9-diol
The assistance of a third functional group in the condensation of a bifunctional species may lead to the situation in which the competition of intramolecular vs. intermolecular reactions is not affected by the dilution of the system.
Chojnowski, Julian,Rubinsztajn, Slawomir,Wilczek, Lech
p. 69 - 71
(1984)
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Hydrogenolysis of Polysilanes Catalyzed by Low-Valent Nickel Complexes
The dehydrogenation of organosilanes (RxSiH4?x) under the formation of Si?Si bonds is an intensively investigated process leading to oligo- or polysilanes. The reverse reaction is little studied. To date, the hydrogenolysis of Si?Si bonds requires very harsh conditions and is very unselective, leading to multiple side products. Herein, we describe a new catalytic hydrogenation of oligo- and polysilanes that is highly selective and proceeds under mild conditions. New low-valent nickel hydride complexes are used as catalysts and secondary silanes, RR′SiH2, are obtained as products in high purity.
Comas-Vives, Aleix,Eiler, Frederik,Grützmacher, Hansj?rg,Pribanic, Bruno,Trincado, Monica,Vogt, Matthias
supporting information
p. 15603 - 15609
(2020/04/29)

Reactions of Trichlorogermane and Trimethylgermane Etherates with 1,3-Divinyl-1,1,3,3-tetramethyldisiloxane
Abstract: The effect of the reactant ratio in the reaction of tetramethyldisiloxane with germanium tetrachloride and diethyl ether on the structure and reactivity of the resulting trichlorogermane–diethyl ether complexes was studied, and the products were
Blagushina, A. I.,Efimenko, D. A.,Gritskova, I. A.,Komalenkova, N. G.,Lakhtin, V. G.,Semyashkina, I. A.,Sokol?skaya, I. B.,Storozhenko, P. A.,Ushakov, N. V.
p. 968 - 976
(2020/07/27)

METHOD FOR PRODUCING SILOXANE OLIGOMER
PROBLEM TO BE SOLVED: To provide a production method capable of simply producing a siloxane oligomer in a high yield when producing a siloxane oligomer by hydrolysis of a silicon halide compound and to provide a production method capable of selectively producing a linear or cyclic siloxane oligomer in particular. SOLUTION: The siloxane oligomer can be efficiently produced without performing any special agitation by providing two electrospray nozzles to oppose to each other in a medium liquid and in the medium liquid, electrostatically spraying in an electric field a first liquid sample containing a silicon halide compound from one nozzle and electrostatically spraying in an electric field a second liquid sample containing water from the other nozzle and allowing the liquid samples to collide and fuse with each other. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPO&INPIT
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Paragraph 0034; 0045

(2017/07/23)

A dimethyl dichloro silane hydrolysate cracking method
The invention discloses a method for splitting dimethyl dichlorosilane hydrolysate. The method comprises the following steps: carrying out load reaction onto strong-basicity macroporous anion exchange resin, potassium hydroxide, potassium trimethylsilanolate and [bmim]BF4 ionic liquid to obtain a composite catalyst after the reaction is ended; adding dimethyl dichlorosilane hydrolysate into a splitting kettle to obtain a ring-body mixture by splitting and re-arranging solvent oil, the composite catalyst and the hydrolysate; and washing with water to remove high-boiling point residues and low-boiling point residues to obtain products such as octamethylcyclotetrasiloxane D4, hexamethylcyclotrisiloxane and decamethylcyclopentasiloxane.
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Paragraph 0026; 0028

(2017/02/24)

Selective Formation of Alkoxychlorosilanes and Organotrialkoxysilane with Four Different Substituents by Intermolecular Exchange Reaction
Alkoxychlorosilanes are scientifically and industrially important toward preparing silicone and silica as well as preparation of siloxane-based nanomaterials by stepwise reactions of Si?OR (R=alkyl) and Si?Cl groups. Intermolecular exchange of alkoxy and chloro groups between alkoxysilanes and chlorosilanes (functional group exchange reaction) provides an efficient and environmentally benign route to alkoxychlorosilanes. BiCl3 as a Lewis acid catalyst can promote the functional group exchange reactions more efficiently than conventional acid catalysts. Higher reactivity has been observed for chlorosilanes with smaller numbers of Si?CH3 groups and for alkoxysilanes with larger numbers of Si?CH3 groups. The reaction mechanism is proposed and selective syntheses of alkoxychlorosilanes are demonstrated. These findings also enable us to synthesize an organotrialkoxysilane with four different substituents.
Komata, Yuma,Yoshikawa, Masashi,Tamura, Yasuhiro,Wada, Hiroaki,Shimojima, Atsushi,Kuroda, Kazuyuki
p. 3225 - 3233
(2016/11/29)

One-Step Synthesis of Siloxanes from the Direct Process Disilane Residue
The well-established Müller–Rochow Direct Process for the chloromethylsilane synthesis produces a disilane residue (DPR) consisting of compounds MenSi2Cl6?n(n=1–6) in thousands of tons annually. Technologically, much effort is made to retransfer the disilanes into monosilanes suitable for introduction into the siloxane production chain for increase in economic value. Here, we report on a single step reaction to directly form cyclic, linear, and cage-like siloxanes upon treatment of the DPR with a 5 m HCl in Et2O solution at about 120 °C for 60 h. For simplification of the Si?Si bond cleavage and aiming on product selectivity the grade of methylation at the silicon backbone is increased to n≥4. Moreover, the HCl/Et2O reagent is also suitable to produce siloxanes from the corresponding monosilanes under comparable conditions.
Neumeyer, Felix,Auner, Norbert
supporting information
p. 17165 - 17168
(2016/11/23)

Method for preparing hybrid cyclo-boron siloxane
The invention relates to the field of chemistry and chemical engineering, provides a cheap and efficient cyclo-boron siloxane intermediate in order to prepare high-performance boracic polysiloxane, and particularly provides a method for preparing hybrid cyclo-boron siloxane. Under inert gas shielding, a mixture of alkyl boric acid and an organic solvent A is dropwise added to dialkyl dichloro-slane, stirring and reacting are carried out for 3 h to 8 h at the temperature of -20 DEG C to 80 DEG C, then the mixture is added into a mixture of an organic solvent B and metallic oxide, filtering and washing are carried out after reacting is carried out for 6 h to 18 h, the organic solvent A and the organic solvent B are evaporated out, and hybrid cyclo-boron siloxane is obtained. The method has the advantages that the raw materials can be obtained easily, and cost is low, and the compound can be used for synthesizing boron-silicon rubber, a heat-resisting adhesive, a heat-resisting coating and other boracic polysiloxane products, and can be widely applied to aerospace, electronics, chemical engineering, machinery and other industries.
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Paragraph 0032; 0033; 0034; 0035; 0036; 0037; 0038

(2016/10/10)

Platinum-catalyzed reduction of DMF by 1,1,3,3-tetramethyldisiloxane, HMeSi2OSiMe2H: New intermediates HSiMe 2OSiMe2OCH2NMe2 and HSiMe 2(OSiMe2)3OCH2
The use of Karstedt's catalyst to study the reduction of Me2NCHO (DMF) by the popular "dual SiH"-containing tetramethyldisiloxane, HMe2SiOSiMe2H (1), has revealed that the first step in the process involves an initial sing
Martinez, Jorge L.,Sharma, Hemant K.,Arias-Ugarte, Renzo,Pannell, Keith H.
supporting information
p. 2964 - 2967
(2014/07/08)

Si-permethylcyclo(1-methoxyphosphoryloxy)siloxanes: New synthons in the processes of low-temperature production of dimethylsilanone
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Basenko,Soldatenko,Voronkov
p. 135 - 138
(2013/07/19)

Effect of catalyst structure on the reaction of α-methylstyrene with 1,1,3,3-tetramethyldisiloxane
Reaction of α-methylstyrene with 1,1,3,3-tetramethyldisiloxane in the presence of the complexes of platinum(II), palladium(II) and rhodium(I) is explored. It is established that in the presence of platinum catalyst predominantly occurs hydrosilylation of α-methylstyrene leading to formation of β-adduct, on palladium catalysts proceeds reduction of α-methylstyrene, on rhodium catalysts both the processes take place. In the reaction mixture proceeds disproportion and dehydrocondensation of 1,1,3,3-tetramethyldisiloxane that leads to formation of long chain linear and cyclic siloxanes of general formula HMe2Si(OSiMe2) n H and (-OSiMe2-)m (n = 2-6, m = 3-7), respectively. Platinum catalysts promotes formation of linear siloxanes, while both rhodium and palladium catalysts afford linear and cyclic siloxanes as well. Structure of intermediate metallocomplexes is studied.
De Vekki,Skvortsov
body text
p. 762 - 777
(2009/09/26)

METHOD FOR THE PRODUCTION OF CYCLIC POLYSILOXANES
A process for producing cyclic polysiloxanes is disclosed. The first step of the process comprises combining a poiysiloxane, a cafaiyst and a high boiling endblocker, wherein the catalyst is selected from the group consisting of a phosphazene base and a carborane acid. The second step of the process comprises heating said poiysiloxane, catalyst and high boiling endblocker, and the third step of the process comprising recovering the cyclic poiysiloxane,
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Page/Page column 19-21

(2009/01/23)

Novel direct process
The invention relates to continuous processes for making cyclic dimethylsiloxane oligomers by reacting in situ methyl bromide, dimethyl ether and activated silicon particles in a direct process reaction zone to produce methylsiloxanes, wherein the proportion of dimethylsiloxane produced in said reaction zone is greater than 75 mole % of the methylsiloxanes produced and recovering the dimethylsiloxane from the reactions zone. The invention favors making cyclic dimethylsiloxane oligomers by this in situ direct reaction.
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Page/Page column 19-20

(2008/06/13)

REACTIVE DISTILLATION OF CHLOROSILANES
Chlorosilanes such as dimethyldichlorosilane are hydrolyzed in a first super-azeotropic hydrochloric acid distillation column A to produce cyclosiloxanes, chlorosiloxanes, and hydrogen chloride gas. The cyclosiloxanes and the chlorosiloxanes are washed and separated according to their volatility in a second sub-azeotropic hydrochloric acid distillation column B, to produce a substantially chloride free volatile cyclosiloxane stream and a substantially chloride free non- volatile siloxane stream. The process is substantially chloride efficient.
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Page/Page column 7-8

(2008/06/13)

A facile and efficient synthesis of organocyclosiloxanes
A new facile preparative method for the synthesis of organocyclosiloxanes is reported. Ring closure of the dichlorosilanes with NaHCO3 and pyridine gave mixture of organocyclosiloxanes with cyclotrisiloxane as a main product.
Zuev, Vjacheslav V.,Kalinin, Alexei V.
p. 1289 - 1294
(2007/10/03)

Anionic and cationic ring-opening polymerization of 2,2,4,4,6,6-hexamethyl-8,8-divinylcyclotetrasiloxane
Ring-opening polymerization (ROP) of 2,2,4,4,6,6-hexamethyl-8,8-divinylcyclotetrasiloxane (I) initiated by both l-fert-butyl-4,4,4-tris(dimetnylamino)-2,2-bis[tris(dimethylamino)phosphoran-yli denamino]-2λ5,4λ5-catenadi(phosphazene) (C22H63N13P4, P4-t-Bu Superbase) and trifluoromethanesulfonic acid (CF3SO3H, triflic acid) has been studied. Both reactions lead to mixtures of linear copolymer, low molecular weight co-oligomers and monomeric cyclosiloxanes. The composition, molecular weight distribution, microstructure, and thermal properties of the copolymers have been determined. The copolymer microstructure has been determined by 29Si NMR spectroscopy. Monomeric cyclosiloxanes have been identified by GC/MS. Both copolymer microstructure and cyclosiloxanes formed depend on the particular catalyst system utilized. P4-t-Bu superbase-initiated anionic ROP of I leads to a copolymer with a random microstructure and to a series of monomeric cyclotetra-, cyclopenta-, and cyclohexasiloxanes formed by random combination of dimethylsiloxane (D) and divinylsiloxane (V) units. On the other hand, triflic acid-initiated ROP of I occurs in a chemoselective manner. This leads to a copolymer with a more ordered microstructure. In this case, I is the only monomeric cyclosiloxane found.
Teng, Conan J.,Weber, William P.,Cai, Guoping
p. 5126 - 5130
(2007/10/03)

Reaction of the dioxane complex of dichlorogermylene with siloxanes
The major organogermanium compounds formed by reactions of the dioxane complex of dichlorogermylene with hexamethyldisiloxane, octamethyltrisiloxane, and hexamethyltricyclotrisiloxane are bis(trimethylsiloxy)dichlorogermane, 3,3-dichloro-1,1,1,5,5,7,7,7-o
Shcherbinin,Pushkina,Krivolapova,Bykovchenko,Khromykh,Komalenkova,Chernyshev
p. 1907 - 1910
(2007/10/03)

New route to permethylcyclosiloxanes
A new method for preparing permethylcyclosiloxanes, based on reaction of 1,1,3,3-tetramethyldisiloxane with iodine (molar ratio 1:1) in inert organic solvents (alkanes, alkyl halides, benzene) is proposed. The products of the reaction react with ethoxytrimethylsilane and tetramethoxysilane in hexamethyldisiloxane to give respectively pentamethyldisiloxane and products of successive substitution of the methoxy groups in Si(OMe)4 by Me2SiHO. A probable scheme of their formation is discussed.
Basenko,Klyba,Voronkov
p. 1368 - 1370
(2007/10/03)

Synthesis of 14C-labeled cyclic and linear siloxanes
Simple procedures to synthesize a variety of 14C-labeled monomeric and polymeric siloxanes are described. Specifically, the synthesis of the following siloxanes, some of which are of significant commercial importance are provided: 14C-octamethylcyclotetrasiloxane (D4), 14C-decamethylcyclopentasiloxane (D5), 14C-hexamethyldisiloxane (MM), 14C-dimethyldimethoxysilane and 14C-dimethylsilanediol (DMSD) are examples of discrete monomeric species. 14C-350 and 1000 cSt polydimethylsiloxanes (PDMS) are examples of polymeric species. Synthesis of the monomeric species with the exception of dimethylsilanediol involve reactions of Grignard reagents with the appropriate chlorosilanes, while the polymeric materials were synthesized via acid catalyzed equilibration reaction of 14C-D4 with dodecamethylpentasiloxane (MD3M). The compound 14C-DMSD was obtained by the hydrolysis of 14C-dimethyldimethoxysilane. The labeled materials listed here were synthesized for their utility as tracers in several of the ongoing environmental fate and effects studies as well as toxicological investigations.
Varaprath, Sudarsanan
p. 37 - 47
(2007/10/03)

Unusual Transformations of Trimethylphenoxysilane in the Reaction with Gallium Oxide
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Voronkov, M. G.,Tsyrendorzhieva, I. P.,Albanov, A. I.,Shergina, N. I.,Klyba, L. V.,Dubinskaya, E. I.
p. 656 - 657
(2007/10/03)

Reaction of Octamethylcyclotetrasiloxane with Aluminum, Gallium, and Silicon Iodides
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Voronkov, M. G.,Tsyrendorzhieva, I. P.,Albanov, A. I.,Shergina, N. I.,Klyba, L. V.,Dubinskaya, E. I.
p. 654 - 655
(2007/10/03)

A New Method for Generation of Dimethylsilanone under Mild Conditions
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Voronkov, M. G.,Tsyrendorzhieva, I. P.,Ivanova, N. P.,Dubinskaya, E. I.
p. 658 - 659
(2007/10/03)

Reaction of Dimethyl Sulfoxide with Diorganyldichlorosilanes: A New Route of Generation of Diorganylsilanones
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Basenko, S.V.,Voronkov, M.G.
p. 248 - 250
(2007/10/02)

Siloxane basicity toward strong acid in nonpolar solution
The relative basicities of ten siloxanes and an ether were studied in benzene by determining from visible spectroscopic measurements the thermodynamic constants for the competition between the substrate and a reference base (4-chloro-2-nitroaniline) for acid (trifluoromethanesulfonic acid): RB-HA + S ? RB + S·HA. The Keq values were considered as a measure of basicity with the following order established and explained by inductive effects in the protonated species: permethyl linear siloxanes (Me3Si(OSiMe2)nOSiMe3, n = 0-3) > dibutyl ether > HMe2SiOSiMe2H > branched siloxanes ((Me3SiO)3SiMe, (Me3SiO)4Si) > cyclic siloxanes ((Me2SiO)n, n = 3-5). The ΔH and ΔS values were positive and increased with higher basicity; this behavior was attributed to differential solvation of ion pairs.
Shepherd, Brian D.
p. 5581 - 5583
(2007/10/02)

EFFECT OF HYDROCHLORIC ACID ON RING FORMATION IN HYDROLYTIC POLYCONDENSATION OF DIFUNCTIONAL ORGANOCHLOROSILANES
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Kopylov, V. M.,Agashkov, S. P.,Sunkovich, G. V.,Prikhod'ko, P. L.,Ezerets, M. A.,Glukhova, M. A.
p. 1873 - 1878
(2007/10/02)

On the Problem of the Intermediate Formation of Silanone R2Si=O by Reactions of Silenes with Dinitrogen Oxide
The silaethene Me2Si=C(SiMe3)2 (1a; unstable; from 1a * Ph2C=MSiMe3 = 4) forms with N2O an unstable cycloadduct, which decomposes under isomerization or cleavage.It was not possible to decide clearly, whether the last reaction, which leads to (Me3Si)2CN2 and polymers with (Me2SiO)n groups, proceeds with intermediate formation of silanone Me2Si=O or not (no trapping product with Et3SiH, but with Me3SiCl).The silanimines Me2Si=NSitBu3 (2a; unstable; from 2a * tBu3SiN3 = 7) and tBu2Si=NSitBu3 (2b; metastable) form with N2O unstable cycloadducts, which, under participation of the silanimines, react into products (10) being composed of a molecular silanone and a molecule silanimine.As has been shown by trapping experiments with Et3SiH, Me3SiCl, or Me3SiOMe, latter reaction involves unstable free silanones Me2Si=O (3a) or tBuSi=O (3b) as intermediates. 3b, generated in benzene from 2b/NO2 in the presence of equimolar amounts of tetrahydrofuran (THF), obviously forms an adduct 3b*THF, which is trapped by excess 2b.When 3b is produced in THF as solvent, the silanone starts THF polymerization, indicating a high Lewis acidity of silanones.
Wiberg, Nils,Preiner, Gerhard,Schurz, Klaus
p. 1407 - 1412
(2007/10/02)

REACTION OF ORGANOCHLOROSILANES WITH OXYGEN HETEROCYCLES AND LITHIUM
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Krasnova, T. L.,Mudrova, N. A.,Bochkarev, V. N.,Kisin, A. V.
p. 1358 - 1362
(2007/10/02)

SILYL AND SILYLMETHYL RADICALS, SILYLENES, SILA-ALKENES, AND SMALL RING SILACYCLES IN REACTIONS OF ORGANOCHLOROSILANES WITH ALKALI METAL VAPOURS
Dehalogenation of the organochlorosilanes Me3SiCl (I), Me2PrSiCl (II), Me3SiSiMe2Cl (III), Me3SiCH2SiMe2Cl (IV), ClCH2SiMe3 (V), ClCH2SiMe2SiMe3 (VI), ClCH2Me2SiSiMe2CH2Cl (VII), Me2SiCl2 (VIII), MePrSiCl2 (IX), Me3SiCH2SiMeCl2 (X), Me3SiCH2CH2SiMeCl2 (XI), Me3SiCH2CH2CH2SiMeCl2 (XII), ClCH2Si(H)MeCl (XIII), ClCH2SiMe2Cl (XIV), ClMe2SiSiMe2Cl (XV), ClCH2CH2CH2Si(H)MeCl (XVI), ClCH2CH2CH2SiMe2Cl (XVII), ClCH2CH2OSiMe2Cl (XVIII), ClMe2SiCH2SiMe2Cl (XIX), ClMe2SiCH2CH2SiMe2Cl (XX), and ClMe2SiCH2CH2CH2SiMe2Cl (XXI) with K/Na alloy vapours at 0.1-1 Torr and 300-320 deg C yields products derived from the reactions of short-lived intermediates, such as silyl and silylmethyl radicals, silylenes, and sila-alkenes.In addition, small-ring silacycles of low stability are formed as the intermediates in some of the dehalogenation reactions.Combination and H-atom abstraction are the main reactions of silyl and silyl-methyl radicals.These radicals are not prone to decomposition reactions when C-H, C-C, or Si-C bonds are at the β(Si-Si) bond with the formation of Me2Si=CH2 and the trimethylsilyl radical.The generation of alkylmethylsilylenes is accompanied by their decomposition processes, which involves intramolecular β(C-H) insertion of alkylmethylsilylenes and 2+1>-thermocyclodecomposition of intermediate silacyclopropanes.The contribution of δ(C-H) and ε(C-H) insertion reactions is much less pronounced, and in the formation of five- or six-membered silacycles.We did not succeed in obtaining monosilacyclobutanes, as the intramolecular γ(C-H) insertion is not typical for silylenes with alkyl substituents.Dehalogenation of chloromethylchlorosilanes with alkali metal vapours yields sila-alkenes, and that of 1,2-dichlorodisilanes gives disilenes. 1-Methyl-1-silaethylene, obtained by this method, does not rearrange into dimethylsilene, but dimerizes to give 1,3-dimethyl-1,3-disilacyclobutane.The formation of 1,3,5-trisilacyclohexanes takes place due to subsequent radical addition at the silicon-carbon double bond and cyclization of 1,6-biradicals.Dehalogenation of organochlorosilanes XVI, XVII, and XX opens up possibilities for the gas-phase synthesis of small organosilicon heterocycles: monosilecyclobutanes and 1,2-disilacyclobutanes.A new, low-stability heterocycle, i.e. 1,1,2,2-tetramethyl-1,2-disilacyclobutane, has been obtained, which enables a new, high polymer, polyethylenetetramethyldisilene, to be obtained.In the case of organochlorosilanes XVIII and XIX, cyclization is accompanied by secondary reactions of silacycles, rearrangements, dimerization, or decomposition.
Gusel'nikov, L. E.,Polyakov, Yu. P.,Volnina, E. A.,Nametkin, N. S.
p. 189 - 204
(2007/10/02)

NEW REACTION LEADING TO UNSTABLE 2,2-DIMETHYL-1,2-OXASILETANE
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Gusel'nikov, L. E.,Kerzina, Z. A.,Polyakov, Yu. P.,Nametkin, N. S.
p. 401
(2007/10/02)

UNUSUAL REDUCTIVE CONDENSATIONS IN THE REACTION OF DIIODODIMETHYLSILANE WITH KETONES
Diiododimethylsilane reacts with various ketones in the presence of zinc to give the corresponding reductive condensation products in good yields.
Ando, Wataru,Ikeno, Masayuki
p. 1255 - 1256
(2007/10/02)