Hydridosilane Manufacturing Process

Abstract

A process for producing one or more silane compounds (A) having at least one Si-H bond, comprising reacting one or more compounds having at least one Si-X bond (B), where X is a halogen atom, with one or more metal hydrides (C) in the presence of one or more heterocyclic ionic liquids.

Description

[Technical Field]

[0001] The present invention relates to the production of hydridosilanes, particularly processes for the production of organohydridosilanes and organohydridohalosilanes, using metal hydrides as reducing agents in heterocyclic ionic liquids that act as both solvents and redispersion aids, and more particularly to the production of dimethylchlorosilanes from dimethyldichlorosilane using CaH as the reducing agent, and to compositions comprising hydridohalosilanes, metal halides, and one or more heterocyclic ionic liquids. [Background technology]

[0002] The partial or complete reduction of halosilanes, particularly chlorosilanes, to their hydrogenated analogs is an important transformation, producing key intermediates in both organic and inorganic silicon chemistry.

[0003] Organohydrido- and organohydridochlorosilanes, in particular, are versatile reagents due to their ability to add multiple bonds via hydrosilylation reactions.

[0004] In particular, hydridochlorosilanes are useful building blocks in synthetic silicon chemistry because they exhibit bifunctional substitution, allowing either the Si—Cl or Si—H moiety of such silanes to undergo selective transformation, while the other moiety remains unaffected and can be further functionalized in subsequent steps.

[0005] For example, Me2SiHCl is an important intermediate for the synthesis of a wide variety of functional silicones by hydrosilylation. Me2SiHCl is a naturally occurring component in the chlorosilane mixture obtained by the Rochow process. However, the portion of Me2SiHCl produced as a by-product in the Rochow process is too small to meet the increasing demand due to the current development of a broad portfolio of highly specialized functional silicones.

[0006] There is a need for a simple and efficient one-step process that allows for the preparation of organohydridosilanes, such as Me2SiHCl, using unrestricted and readily available raw materials.

[0007] The following concept has been proposed and partially used to simultaneously synthesize Si-Cl and Si-H bond containing silanes by reduction.

[0008] 1. Reduction of Si-Cl bonds to Si-H bonds using H2 Although H2 is an inexpensive reducing agent, the reduction of Si-Cl to Si-H has been found to depend on very specific catalytic sites combined with extreme conditions. US5716590 discloses that Ni-silicide can be combined with H2 at high temperatures to obtain SiH silane starting from SiCl silane. US4059608 discloses that in the presence of Ni dispersed in HMPT, combined with H2, the hydrogenolytic cleavage of Si-Si bonds produces SiH silane.

[0009] 2. Reduction of Si-Cl using metal hydrides JPH0324091 discloses a process for reducing chlorosilanes using LiH in combination with a salt mixture of LiCl / KCl at high temperatures above 350° C. However, LiH is a very expensive metal hydride and the energy consumption of this process is high.

[0010] EP 0301678 discloses a Sn-based system, however Sn-based systems are expensive, toxic and / or difficult to handle.

[0011] EP 0 878 476 discloses a process using MgH2 / AlCl3 in combination with an inert solvent activated by milling, and US 5,455,367 discloses a process using MgH2 in ether activated by ultrasound. AlCl3 is a volatile compound and is difficult to separate from the target product. Milling and ultrasound require non-standard equipment, thus increasing the complexity of the reaction.

[0012] G. Simon et al., J. Organomet. Chem., Jan. 1, 1981, pp. 279-286, disclose that Me2SiCl2 can be reduced to Me2SiHCl with CaH2 at high temperatures of 300°C, but only in very low yields.

[0013] US11008349 proposes a system consisting of LiH, an ether solvent, and PR4Cl as a redispersion catalyst. LiH forms Me2SiH2 from Me2SiCl2. Me2SiH2 is then redispersed with Me2SiCl2 in the presence of PR4Cl to produce Me2SiHCl. Therefore, an excess of Me2SiCl2 is important to form the desired product, Me2SiHCl, from the intermediate Me2SiH2. Furthermore, this patent discloses in a general manner the use of the quaternary ammonium compound NR4Cl as a redispersion catalyst instead of PR4Cl.

[0014] EP3915995A1 and WO2019 / 060487A1 also disclose methods for preparing compounds having at least one Si-H bond using LiH in the presence of n-BuPCl, the reaction therefore being carried out in the absence of a heterocyclic ionic liquid.

[0015] EP 1 717 241 A1 discloses a redispersion reaction of MeSiCl and SiH2Cl2 in the presence of 1-butyl-3-methylimidazolium chloride. Thus, this process does not involve a reduction reaction of a chlorosilane with a metal hydride followed by a redispersion reaction between the chlorosilane and the formed hydridosilane, but is directed to a redispersion reaction in which an organochlorosilane is reacted with a hydridochlorosilane that does not have an organyl residue. Summary of the Invention

[0016] The present invention, which is described in detail below, relates to a process for the preparation of one or more silane compounds (A) having at least one Si-H bond, comprising the step of reacting one or more compounds (B) having at least one Si-X bond, where X is a halogen atom, with one or more metal hydrides (C) in the presence of one or more heterocyclic ionic liquids.

[0017] DETAILED DESCRIPTION OF THE INVENTION

[0018] The process according to the invention is a process for the preparation of one or more silane compounds (A) having at least one Si-H bond, which comprises reacting one or more compounds (B) having at least one Si-X bond, where X is a halogen atom, with one or more metal hydrides (C) in the presence of one or more heterocyclic ionic liquids.

[0019] The term "one or more compounds (B) having at least one Si-X bond", as defined herein, includes any compound (B) containing at least one Si-X bond, where X is a halogen, i.e., a fluoro, chloro, bromo, or iodo group, preferably a chloro group, and includes mixtures of two or more of such compounds, which serve as starting materials in the process of the present invention.

[0020] Thus, the starting material(s) may be selected from monosilanes, disilanes, oligosilanes, or polysilanes, and carbodisilanes having at least one Si-X bond, where in the process according to the invention, monosilanes, disilanes, oligosilanes, and polysilanes are preferred compounds (B), monosilanes and disilanes are more preferred compounds (B), and monosilanes are generally the most preferred compound (B).

[0021] The process of the present invention may be applied to any type of silane compound (B), including silanes (B) having at least one Si-X bond with a substituent selected exclusively from halogen and hydrogen atoms, but preferably the process of the present invention is applied to organosilanes, i.e., compounds (B) having at least one Si-R bond, where R is an organyl group. The term "organyl group," as defined herein, refers to any organic group having one free valence at a carbon atom, and thus the organyl group R is bonded to the Si atom of the silane via a carbon atom.

[0022] According to an embodiment of the present invention, the organyl group R comprises optionally substituted, but preferably unsubstituted, groups independently selected from the group consisting of: alkyl, aryl, alkenyl, alkynyl, alkaryl, aralkyl, aralkenyl, aralkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, cycloaralkyl, cycloaralkenyl, and cycloaralkynyl groups, even more preferably selected from alkyl, cycloalkyl, alkenyl, and aryl groups, even more preferably selected from methyl, ethyl, vinyl, and phenyl, and most preferably R is a methyl group.

[0023] As defined herein, the term "alkyl group" includes unbranched n-alkyl groups, branched alkyl groups, and cyclic alkyl groups. According to an embodiment of the present invention, alkyl groups having 1 to 22 carbon atoms are preferred, alkyl groups having 1 to 12 carbon atoms are more preferred, and alkyl groups having 1 to 8 carbon atoms, particularly methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, cyclopentyl, sec-pentyl, isopentyl, neopentyl, n-hexyl, cyclohexyl, n-heptyl, and n-octyl, are even more preferred.

[0024] As defined herein, the term "aryl group" includes all groups derived from monocyclic and polycyclic aromatic hydrocarbons by removing a hydrogen atom from a ring carbon atom.

[0025] According to an embodiment of the present invention, aryl groups having 6-22 carbon atoms, especially phenyl groups, are preferred.

[0026] As defined herein, the term "alkenyl group" includes unbranched, branched, and cyclic hydrocarbyl residues having one or more carbon-carbon double bonds. According to an embodiment of the present invention, alkenyl groups having 1 to 22 carbon atoms are preferred, alkenyl groups having 1 to 12 carbon atoms are more preferred, and alkenyl groups having 1 to 8 carbon atoms, particularly vinyl and allyl groups, are even more preferred.

[0027] The one or more halogen atoms X bonded to the Si atom or atoms of silane compound (B) are selected from fluorine, chlorine, bromine, and iodine atoms, preferably chlorine, where silane compound B may contain two or more different types of halogen atoms, but preferably silane compound B contains one type of halogen atom bonded to the Si atom or atoms. While silane (B) containing all of the above types of halogen atoms can be subjected to the process of the present invention, in embodiments of the present invention, halogen atoms X are preferably selected from iodine, bromine, and chlorine atoms, more preferably bromine and chlorine atoms, and most preferably all halogen atoms X of silane compound (B) are selected from chlorine atoms.

[0028] Furthermore, according to an embodiment of the present invention, it is preferred that the silane compound (B) is exclusively substituted with halogen substituents or organic and halogen substituents, i.e., compound (B) is preferably a perhalogenated silane, in particular a perhalogenated organosilane. More preferably, compound (B) is a perchlorinated silane, and in particular a perchlorinated organosilane, even more preferably selected from tetrachlorosilane and organochloromonosilanes RSiCl3, R2SiCl2, and R3SiCl, where R is an organyl group. Even more preferably, compound (B) is selected from MeSiCl3 and Me2SiCl2, and most preferably compound (B) is Me2SiCl2.

[0029] Silane compounds having at least one Si-X(B) bond can be monosilanes, disilanes, polysilanes, and carbodisilanes. As defined herein, the term polysilane includes all types of silanes having three or more silicon atoms bonded to one another in a linear chain, i.e., forming, for example, a-Si-Si-Si-moieties in the case of trisilane.

[0030] Monosilane: The monosilane (B) having at least one Si-X bond and serving as starting material can be either a monosilane bearing only one or more substituents selected from one or more halogen atoms X, preferably chlorine atoms, and optionally hydrogen atoms, or a monosilane bearing one or more substituents selected from one or more halogen atoms, preferably chlorine atoms, one or more organyl substituents R, and optionally hydrogen atoms. The organyl groups R can be the same or different in organomonosilanes bearing two or more groups R. The one or more organyl groups R are optionally substituted, but preferably unsubstituted, groups independently selected from the group consisting of: alkyl, aryl, alkenyl, alkynyl, alkaryl, aralkyl, aralkenyl, aralkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, cycloaralkyl, cycloaralkenyl, and cycloaralkynyl groups, even more preferably alkyl, cycloalkyl, alkenyl, and aryl groups, even more preferably selected from methyl, ethyl, vinyl, and phenyl, and most preferably R is a methyl group.

[0031] Preferred monosilanes bearing only halogen and hydrogen atoms are SiCl4, SiBr4, SiI4, HSiCl3, HSiBr3 and HSiI3, with SiCl4 and HSiCl3 being most preferred.

[0032] According to an embodiment, preferably the monosilanes (B) having at least one Si-X bond are organomonosilanes, i.e. they have one or more substituents R, more preferably R is an unsubstituted alkyl or phenyl group.

[0033] According to an embodiment of the present invention, the organomonosilane (B) preferably has the following general formula: R a SiH b X c wherein X is a halogen atom, preferably chlorine; R is an organyl group, a=1 to 3, b=0 to 2, c=1 to 3, and a+b+c=4.

[0034] Although the process according to the invention is also suitable for the reduction of organohalomonosilanes of the general formula RSiX, in particular RSiCl, in accordance with an embodiment, the process is preferably applied to organodihalomonosilanes and organotrihalomonosilanes of the general formula RSiX and RSiX, in particular RSiCl and RSiCl, where R is an organyl group and X is a halogen atom as defined above, and R is preferably selected from the group consisting of unsubstituted C-C alkyl groups, unsubstituted C-C alkenyl groups, and C-C aryl groups, more preferably methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, cyclopentyl, cyclohexyl, norbornyl, isopropyl, isobutyl, tert-isobutyl, isoamyl, vinyl, allyl, phenyl, and naphthyl groups, and most preferably methyl, vinyl, and phenyl groups.

[0035] Therein, the above-mentioned organodihalo- and organotrihalosilanes may be fully hydrogenated by replacing all Si-X bonds by Si-H bonds in the reaction with the metal hydride, but in the process according to the invention, preferably the corresponding organohydridohalosilanes of the general formula RSiHX, RSiHX and RSiHX are obtained, and even more preferably the corresponding organohydridohalosilanes of the general formula RSiHCl, RSiHCl and RSiHCl.

[0036] According to an embodiment, the most preferred monosilanes (B) are MeSiCl and MeSiCl, and the most preferred products (A) of processes according to embodiments of the present invention based on the described monosilane starting materials (B) are MeSiHCl, MeSiHCl, and MeSiHCl.

[0037] Disilane: The disilanes (B) having at least one Si-X bond and serving as starting materials can be either disilanes bearing only one or more substituents selected from one or more halogen atoms X, preferably chlorine atoms, and optionally hydrogen atoms, or disilanes bearing one or more substituents selected from one or more halogen atoms, preferably chlorine atoms, one or more organyl substituents R, and optionally hydrogen atoms. The organyl groups R can be the same or different in organodisilanes bearing two or more groups R. The one or more organyl groups R are optionally substituted, but preferably unsubstituted, and are selected from the group consisting of alkyl, aryl, alkenyl, alkynyl, alkaryl, aralkyl, aralkenyl, aralkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, cycloaralkyl, cycloaralkenyl, and cycloaralkynyl groups, even more preferably selected from alkyl, cycloalkyl, alkenyl, and aryl groups, even more preferably selected from methyl, ethyl, vinyl, and phenyl groups, and most preferably R is a methyl group.

[0038] Preferred disilanes bearing only halogen and hydrogen atoms are Si2Cl6, Si2Br6 and Si2I6, of which Si2Cl6 is most preferred.

[0039] Preferably, the disilanes (B) having at least one Si—X bond are organodisilanes, i.e., they have one or more substituents R, more preferably R is an unsubstituted alkyl group or a phenyl group.

[0040] According to an embodiment of the present invention, the organodisilane (B) preferably has the following general formula: R e SiH f X g where R is an organyl group as defined above and X is a halogen atom, preferably chlorine; e=1 to 5, f=0 to 4, g=1 to 5, and e+f+g=6.

[0041] General empirical formula R e SiH f X g Disilanes also have the structural formula: [ka] where the substituents R′ are independently selected from the organyl group R defined above, hydrogen atoms, and halogen atoms X, preferably chlorine, and where the number of organic substituents e=1 to 5, the number of hydrogen atoms f=0 to 4, and the number of halogen atoms g=1 to 5, and the total number e+f+g=6.

[0042] As defined herein, the term "empirical formula" is intended to mean that the formula does not represent a structural formula, but is merely the sum of the chemical groups or atoms present in the molecule. For example, the empirical formula R2Si2Cl4 has the structural formula: [ka] may include:

[0043] According to an embodiment of the present invention, it is preferred that the organodisilane (B) carries only organyl substituents R and halogen substituents X, and more preferably the organodisilane is selected from the group of disilanes having the formulae RSiX, RSiX, and RSiX. Even more preferably it is RSiCl, RSiCl, and RSiCl, where R is as defined above. More preferably, where R is selected from alkyl, aryl, and alkenyl groups, and even more preferably from phenyl, vinyl, ethyl, and methyl groups.

[0044] In the process according to the invention, all halogen atoms of the disilane compound (B) may be replaced by hydrogen atoms, but in some embodiments it is preferred that the organohalodisilane is only partially hydrogenated, thus producing organohydridohalodisilane (A), in particular organohydridochlorodisilane (A).

[0045] The organohalodisilane (B) and the product (A) obtained by partial or complete hydrogenation of the starting material (B) can undergo a cleavage reaction in the process according to the invention, simultaneously with the hydrogenation, preferably partial hydrogenation, carried out in the process by reaction of the silane starting material (B) with the metal hydride (C) and the redispersion reaction promoted by the heterocyclic ionic liquid. In the cleavage reaction of the disilane, the Si-Si bond of this compound is cleaved, resulting in the formation of a monosilane.

[0046] The rate of the cleavage reaction depends on the substitution pattern of compound (B), e.g., the number and type of organyl residues R present in the disilane compound, as well as the reaction conditions, particularly the type of heterocyclic ionic liquid, the reaction temperature, and the reaction time.

[0047] By cleavage of disilane compounds (B) and their hydrogenated analogs, processes according to embodiments of the present invention can provide monosilanes (A) having at least one Si-H bond from disilane (B), preferably organohydridohalomonosilanes, even more preferably organohydridochloromonosilanes of the formula RSiHCl, RSiHCl, and RSiHCl, most preferably MeSiHCl, MeSiHCl, and MeSiHCl.

[0048] Particularly preferred organodisilanes (B) are Me2Si2Cl4, Me3Si2Cl3, and Me4Si2Cl2, and preferred products obtained therefrom according to embodiments of the present invention are Me2SiHCl, MeSiHCl2, MeSiH2Cl, and Me3SiH.

[0049] Polysilane: The polysilane (B) having at least one Si-X bond serving as starting material can be either a polysilane bearing only one or more substituents selected from one or more halogen atoms X, preferably chlorine atoms, and optionally hydrogen atoms, or a polysilane bearing one or more substituents selected from one or more halogen atoms, preferably chlorine atoms, one or more organyl substituents R, and optionally hydrogen atoms. The organyl groups R can be the same or different in organopolysilanes bearing two or more groups R. The organyl group R is optionally substituted, but preferably unsubstituted, and is selected from: alkyl, aryl, alkenyl, alkynyl, alkaryl, aralkyl, aralkenyl, aralkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, cycloaralkyl, cycloaralkenyl, and cycloaralkynyl groups, even more preferably alkyl, cycloalkyl, alkenyl, and aryl groups, even more preferably methyl, ethyl, vinyl, and phenyl groups, and most preferably R is a methyl group.

[0050] According to an embodiment of the present invention, the polysilane is preferably selected from the group of oligosilanes having a linear or branched silane backbone, where q=3 to 7 and the silicon atoms are connected to each other by single bonds, and the compound has the general empirical formula R p Si q H r X s and In the formula, R is an organyl group, X is a halogen atom, preferably a chlorine atom, q=3-7, p=0 to (2q+1), r=0 to (2q+1), s=1 to (2q+2), and r+s=(2q+2)-p.

[0051] Preferred polysilanes that do not carry organic residues are Si3Cl8, Si4Cl 10 , Si5Cl 12 , Si6Cl 14 and Si7Cl 16 is.

[0052] Preferably, according to this embodiment of the present invention, the polysilane has one or more substituents R, more preferably R is an unsubstituted alkyl or phenyl group.

[0053] According to an embodiment of the present invention, it is preferred that these organopolysilanes (B) carry only organyl substituents R and halogen substituents X, more preferably the organopolysilanes are selected from the group of organopolysilanes where R = alkyl, aryl, and alkenyl groups, even more preferably from the group of organopolysilanes where R = phenyl, vinyl, and methyl groups, and most preferably these substituents are selected from methyl and chloro groups.

[0054] In the process according to the invention, all halogen atoms of the polysilane compound (B) may be replaced with hydrogen atoms, but in some embodiments it is preferred that the organohalopolysilane is only partially hydrogenated to produce an organohydridohalopolysilane, in particular an organohydridochloropolysilane.

[0055] Similar to the description of the disilane cleavage reaction above, organohalopolysilane (B) and the products obtained therefrom by hydrogenation and redispersion can be cleaved in processes according to embodiments of the present invention by cleavage of one or more Si-Si bonds, thus producing silanes with fewer silicon atoms, particularly organomonosilanes, more preferably organohydridohalomonosilanes, even more preferably organohydridochloromonosilanes of the formulae RSiHCl, RSiHCl, and RSiHCl, and most preferably MeSiHCl, MeSiHCl, and MeSiHCl.

[0056] Preferred products obtained from organohalopolysilanes according to processes according to embodiments of the present invention, typically obtained as complex mixtures, for example as by-products in the Direct Process for the production of MeSiCl, are RSiHCl, RSiHCl, RSiHCl, and RSiH, where R is an organyl group, preferably an alkyl group. Most preferably, the products are MeSiHCl, MeSiHCl, MeSiHCl, and MeSiH.

[0057] Carbodisilane: The carbodisilanes (B) having at least one Si-X bond which serve as starting materials in the process according to the invention are represented by the general empirical formula R m (Si[CH2] z Si)H n X o and In the formula, R is an organyl group as defined above. m=0 to 5, n=0 to 5, o=1 to 6, z=1 or 2, and m+n+o=6.

[0058] In carbodisilanes carrying two or more groups R, the organyl groups R can be the same or different.

[0059] The organyl group R may be optionally substituted, but is preferably an unsubstituted group selected from the group consisting of alkyl, aryl, alkenyl, alkynyl, alkaryl, aralkyl, aralkenyl, aralkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, cycloaralkyl, cycloaralkenyl, and cycloaralkynyl groups, even more preferably selected from alkyl, cycloalkyl, alkenyl, and aryl groups, even more preferably selected from methyl, ethyl, vinyl, and phenyl, and most preferably R is a methyl group. Preferred carbodisilanes bearing only halogen residues are Cl(SiCHSi)Cl or ClSiCHCHSiCl, the latter of which can be obtained from the reaction ClSiH + CH=CHSiCl, although it is generally preferred that carbodisilanes according to embodiments of the present invention have one or more substituents R, and even more preferably R is an unsubstituted alkyl or phenyl group.

[0060] According to an embodiment of the present invention, it is preferred that these carbodisilanes (B) carry only organyl substituents R and halogen substituents X, more preferably the carbodisilanes are selected from the group of carbodisilanes where R=alkyl, aryl, and alkenyl, even more preferably from the group of carbodisilanes where R=phenyl, vinyl, ethyl, and methyl, and most preferably the substituents are selected from methyl and chloro groups.

[0061] Examples of particularly preferred carbodisilanes are Me2ClSiCH2CH2SiCl3, MeCl2SiCH2CH2SiCl3, Cl3SiCH2CH2SiCl3, Me2ClSiCH2CH2SiMe2Cl, and Me2ClSiCH2CH2SiMeCl2.

[0062] In the process according to the invention, all halogen atoms of the carbodisilane compound (B) may be replaced by hydrogen atoms, but in preferred embodiments, the carbodisilane is only partially hydrogenated to produce an organohydridohalocarbodisilane, particularly an organohydridochlorocarbodisilane.

[0063] According to embodiments of the present invention, organocarbodisilanes may also serve as starting materials (B) for producing organomonosilanes, preferably organohydridohalomonosilanes, even more preferably organohydridochloromonosilanes of the formulae RSiHCl, RSiHCl, and RSiHCl, most preferably MeSiHCl, MeSiHCl, and MeSiHCl. In contrast to the cleavage of disilanes and carbodisilanes, the carbodisilanes cleavage reactions described above, which result in the formation of monosilanes, require the cleavage of one or more Si-C bonds.

[0064] Of the above-mentioned types of silane compounds (B) which have one or more Si-X bonds and which can thus serve as starting materials in the process according to the invention, in embodiments it is preferred that one or more of the following silanes are subjected to the process: monosilanes selected from the formula: MeSiCl3, Me2SiCl2, and Me3SiCl; disilanes selected from the formulae Cl2MeSi-SiMeCl2, Cl2MeSi-SiMe2Cl, Cl2MeSi-SiMe3, ClMe2Si-SiMe2Cl, and Me3Si-SiMe2Cl; oligosilanes selected from the formula: ClMeSi-SiMe-SiMeCl, ClMeSi-SiMe-SiMe-SiMeCl, (ClMeSi)SiMe, (ClMeSi)SiMeCl, (ClMeSi)SiMe, (ClMeSi)SiMe-SiClMe-SiClMe, [(ClMeSi)SiMe], [(ClMeSi)SiMe]SiClMe, and (ClMeSi)SiMe-SiMeCl; Carbodisilanes selected from the formula: Cl2MeSi-CH2-SiMeCl2, ClMe2Si-CH2-SiMeCl2, ClMe2Si-CH2-SiMe2Cl, Me3Si-CH2-SiMeCl2 and Me3Si-CH2-SiMe2Cl, Me2ClSiCH2CH2SiCl3, MeCl2SiCH2CH2SiCl3, Cl3SiCH2CH2SiCl3, Me2ClSiCH2CH2SiMe2Cl, and Me2ClSiCH2CH2SiMeCl2.

[0065] As defined herein, the term "one or more silane compounds (A) having at least one Si-H bond" includes any compound containing at least one Si-H bond. Such a compound (A) or a mixture of several such compounds (A) is the desired product obtained in the process of the present invention by reacting the starting compound (B) with one or more metal hydrides (C) in the presence of one or more heterocyclic ionic liquids.

[0066] The type of compound (A) obtained in the process according to the invention is determined primarily by the choice of starting materials, i.e. the choice of one or more compounds (B) subjected to the process, and furthermore the type of compound formed and / or the distribution of the several compounds (A) obtained may be controlled by the specific reaction conditions applied.

[0067] In the process according to the invention, the starting silane compound (B) is reacted with one or more metal hydrides (C) to obtain one or more silane compounds (A) having at least one Si-H bond, wherein at least one Si-X bond of the one or more compounds (B) is replaced by a Si-H bond, resulting in the formation of one or more hydrogenation products.

[0068] As defined herein, the term "subjected to reaction with" is understood to mean any manner in which compound (B) and metal hydride (C) are contacted in the presence of one or more heterocyclic ionic liquids to effect reaction between one or more silane compounds (B) and one or more metal hydrides (C).

[0069] The metal hydride (C) acts as a hydride donor and is converted to an analogous metal halide, whereas at least one Si-X bond of one or more compounds (B) is replaced by a Si-H bond in the course of the hydrogenation reaction.

[0070] As defined herein, the term "metal hydride (C)" refers to any hydride donor containing at least one metal atom or metal ion, including complex metal hydrides, organometallic reagents, and divalent metal hydrides. The term "complex metal hydride" refers to a metal salt containing a hydride anion, e.g., LiAlH4 or NaBH4, as a hydridometallate anion. Typically, complex metal hydrides contain more than one metal or metalloid. As defined herein, the term "metalloid" includes the elements boron, silicon, germanium, arsenic, antimony, tellurium, carbon, aluminum, selenium, polonium, and astatine.

[0071] The term "organometallic hydride reagent" refers to a compound having a bond between a carbon atom and a metal atom and capable of donating at least one hydride anion for use in the reaction of silane compound (B), resulting in the replacement of at least one Si-X bond with a Si-H bond. A divalent metal hydride, as defined herein, is a metal hydride composed exclusively of a cation and a hydride ion of one specific metal.

[0072] In an embodiment of the present invention, the metal hydride is preferably selected from divalent metal hydrides or complex metal hydrides, more preferably selected from alkali metal hydrides, alkaline earth metal hydrides, and complex metal hydrides containing cations of alkali metals or alkaline earth metals, even more preferably selected from the group of lithium hydride, sodium hydride, potassium hydride, magnesium hydride, calcium hydride, even more preferably selected from magnesium hydride, sodium hydride, or calcium hydride, and most preferably the metal hydride is calcium hydride.

[0073] The molar ratio of hydride ions of one or more metal hydrides to halogen atoms of one or more compounds (B) makes it possible to control the extent of substitution of the Si-X bond in the starting compound (B), and thus determines which silane compound product (A) is primarily formed in the process of the present invention.

[0074] Addition of an equimolar or excess amount of hydride ion in metal hydride (C) relative to the Si-X bond in compound (B), i.e., a molar ratio of hydride ion to Si-X bond equal to or greater than 1, is expected to result in complete hydrogenation of the halosilane, unless hydride anions are otherwise consumed in the reaction mixture. Addition of hydride ion in less than stoichiometric amounts, i.e., a molar ratio less than 1, will result in partial hydrogenation of starting material (B) if one or more compounds have more than one Si-X bond and if starting material (B) has only one Si-X bond and conversion is incomplete.

[0075] The reaction of this process, which results in the replacement of one or more Si-X bonds of compound (B) with Si-H bonds, is carried out in the presence of one or more heterocyclic ionic liquids. As defined herein, a heterocyclic ionic liquid is a salt containing a heterocyclic anion and / or cation, which is liquid under the conditions of the process of the present invention. Typically, the salt or ionic liquid has a melting point below about 150°C, preferably below about 140°C, more preferably below about 120°C, even more preferably below about 100°C, and most preferably below about 50°C. Melting points are measured at ambient pressure using a digital instrument, such as that manufactured by Electrothermal.

[0076] The selection of the ionic liquid is based on parameters such as melting point, polarity, compatibility with the Si compound to be hydrogenated, availability, ease of purification, and recyclability.

[0077] Without wishing to be bound by any theory, it is believed that the presence of one or more heterocyclic ionic liquids promotes and accelerates the reaction between one or more compounds (B) and the metal hydride or metal hydrides (C), particularly by removing metal halides formed on the surface of the metal hydride particles in the hydrogenation reaction. This eliminates the need for other measures such as milling, ultrasonication, or the addition of other activators, thus significantly facilitating the hydrogenation process. Furthermore, the presence of heterocyclic ionic liquids makes it possible to control the ratio of the different silane product compounds (A) formed by hydrogenation by promoting redispersion reactions between the different hydrogenated species of the formed silane compounds and between the different hydrogenated species of the formed silane compounds and the starting silane compound (B).

[0078] According to embodiments of the present invention, the heterocyclic structure of the ionic liquid is not limited in any way, except for the constraint that one or more heteroatoms must be present in the ionic liquid, i.e., that at least one atom other than carbon and hydrogen atoms must be included as a ring member, and the ring structure may be aromatic or non-aromatic.

[0079] Ring structures consisting exclusively of carbon atoms bearing one or more heteroatom substituents are not considered heterocycles according to the present invention. The heteroatoms are typically selected from oxygen (O), sulfur (S), phosphorus (P), and nitrogen (N) atoms, with P-heterocycles and N-heterocycles generally being preferred.

[0080] There are no restrictions on the ring size of the heterocyclic structure, the number of heteroatoms present in the heterocyclic ring, or the type of heteroatom, but the heterocyclic structure is preferably a 5- or 6-membered ring containing one or two heteroatoms, where the heteroatoms are preferably selected from N and P atoms. These structures can be either aromatic or non-aromatic.

[0081] According to an embodiment of the present invention, the heterocyclic ionic liquid is preferably selected from the group consisting of N-heterocyclic ionic liquids and P-heterocyclic ionic liquids.

[0082] As defined herein, N-heterocyclic ionic liquids and P-heterocyclic ionic liquids are heterocyclic ionic liquids as defined above, where the heterocycle of the ionic liquid compound is a P-heterocycle, i.e., a cyclic structure containing one or more P-atoms as ring members, or an N-heterocycle, i.e., a cyclic structure containing one or more N-atoms as ring members.

[0083] Each of the P-heterocycle or N-heterocycle may be present in the cation, the anion, or both the cation and the anion of the ionic liquid, but preferably the P-heterocycle or N-heterocycle is comprised of the cation of the ionic liquid.

[0084] According to embodiments of the present invention, N-heterocyclic ionic liquids are preferred and can be selected from aromatic N-heterocyclic ionic liquids or non-aromatic N-heterocyclic ionic liquids. Examples of aromatic N-heterocyclic ionic liquids according to embodiments of the present invention are ionic liquids selected from imidazolium salts, pyridinium salts, pyrrolium salts, and triazolium salts.

[0085] The general structure of 1,3-substituted imidazolium salts is [ka] R in the formula 1 and R 2 is an organyl residue, preferably a C1-C12 alkyl residue, and Z can be any kind of anion, preferably an anion selected from chloride, bromide, acetate, trifluoroacetate, OTf (trifluoromethanesulfonate), MeSO3 (methanesulfonate), TFSI (bis(trifluoromethylsulfonyl)imide), tetrafluoroborate, or hexafluorophosphate or methylsulfonate; The general structure of N-substituted pyridinium compounds is [ka] R in the formula 3is an organyl residue, preferably a C1-C12 alkyl residue, and Z can be any kind of anion, preferably an anion selected from chloride, bromide, acetate, trifluoroacetate, OTf (trifluoromethanesulfonate), MeSO3 (methanesulfonate), TFSI (bis(trifluoromethylsulfonyl)imide), tetrafluoroborate, or hexafluorophosphate or methylsulfonate; The general structure of N,N-disubstituted pyrrolium salts is [ka] R in the formula 4 and R 5 is an organyl residue, preferably a C1-C12 alkyl residue, and Z can be any kind of anion, preferably an anion selected from chloride, bromide, acetate, trifluoroacetate, OTf (trifluoromethanesulfonate), MeSO3 (methanesulfonate), TFSI (bis(trifluoromethylsulfonyl)imide), tetrafluoroborate, or hexafluorophosphate or methylsulfonate; The general structure of 1,3-substituted 1,2,3-triazolium salts is [ka] R in the formula 6 and R 7 , is an organyl residue, preferably a C1-C12 alkyl residue, and Z can be any kind of anion, preferably an anion selected from chloride, bromide, acetate, trifluoroacetate, OTf (trifluoromethanesulfonate), MeSO3 (methanesulfonate), TFSI (bis(trifluoromethylsulfonyl)imide), tetrafluoroborate, or hexafluorophosphate or methylsulfonate.

[0086] As defined herein, each of the ring carbon atoms of the above structures may also carry, instead of a hydrogen substituent, another substituent, where the substituent is preferably selected from halogen substituents and alkyl groups, more preferably C1-C12 alkyl groups.

[0087] Specific examples of imidazolium salts include 1-ethyl-3-methylimidazolium chloride, 1-butyl-3-methylimidazolium chloride, and 1-hexyl-3-methylimidazolium chloride; specific examples of pyridinium salts include N-butylpyridinium chloride, N-hexylpyridinium chloride, and N-octylpyridinium chloride; specific examples of pyrrolium salts include N,N-dimethylpyrrolium chloride, N-methyl-N-ethylpyrrolium chloride, N-methyl-N-butylpyrrolium chloride, and N-methyl-N-hexylpyrrolium chloride; and specific examples of triazolium salts include N-butyl-N'-methyl-C-methyltriazolium chloride and N-butyl-N'-methyl-C-butyltriazolium chloride.

[0088] Examples of non-aromatic N-heterocyclic ionic liquids according to embodiments of the present invention are ionic liquids selected from morpholinium salts, piperidinium salts, pyrrolidinium salts, and piperazinium salts.

[0089] The general structure of N,N-substituted morpholinium salts is [ka] R in the formula 8 and R 9 is an organyl residue, preferably a C1-C12 alkyl residue, and Z can be any kind of anion, preferably an anion selected from chloride, bromide, acetate, trifluoroacetate, OTf (trifluoromethanesulfonate), MeSO3 (methanesulfonate), TFSI (bis(trifluoromethylsulfonyl)imide), tetrafluoroborate, or hexafluorophosphate or methylsulfonate; The general structure of N,N-substituted piperidinium compounds is [ka] R in the formula 10 and R 11 is an organyl residue, preferably a C1-C12 alkyl residue, and Z can be any kind of anion, preferably an anion selected from chloride, bromide, acetate, trifluoroacetate, OTf (trifluoromethanesulfonate), MeSO3 (methanesulfonate), TFSI (bis(trifluoromethylsulfonyl)imide), tetrafluoroborate, or hexafluorophosphate or methylsulfonate; The general structure of N,N-substituted pyrrolidinium salts is [ka] R in the formula 12 and R 13 is an organyl residue, preferably a C1-C12 alkyl residue, and Z can be any kind of anion, preferably an anion selected from chloride, bromide, acetate, trifluoroacetate, OTf (trifluoromethanesulfonate), MeSO3 (methanesulfonate), TFSI (bis(trifluoromethylsulfonyl)imide), tetrafluoroborate, or hexafluorophosphate or methylsulfonate; The general structure of piperazinium monosalts is [ka] R in the formula 14 , R 15 and R 16is an organyl residue, preferably a C1-C12 alkyl residue, and Z can be any kind of anion, preferably an anion selected from chloride, bromide, acetate, trifluoroacetate, OTf (trifluoromethanesulfonate), MeSO3 (methanesulfonate), TFSI (bis(trifluoromethylsulfonyl)imide), tetrafluoroborate, or hexafluorophosphate or methylsulfonate; The general structure of piperazinium di-salts is [ka] R in the formula 14 , R 15 , R 16 and R 17 is an organyl residue, preferably a C1-C12 alkyl residue, and Z can be any kind of anion, preferably an anion selected from chloride, bromide, acetate, trifluoroacetate, OTf (trifluoromethanesulfonate), MeSO3 (methanesulfonate), TFSI (bis(trifluoromethylsulfonyl)imide), tetrafluoroborate, or hexafluorophosphate or methylsulfonate.

[0090] As defined herein, each of the ring carbon atoms of the above structures may also carry, instead of a hydrogen substituent, another substituent, where the substituent is preferably selected from halogen substituents and alkyl groups, more preferably C1-C12 alkyl groups.

[0091] Specific examples of morpholinium salts include N,N-dimethyl-morpholinium chloride, N-methyl-N-ethyl-morpholinium chloride, N-methyl-N-butyl-morpholinium chloride, and N-methyl-N-hexyl-morpholinium chloride; specific examples of piperidinium salts include N,N-dimethyl-piperidinium chloride, N-methyl-N-ethyl-piperidinium chloride, N-methyl-N-butyl-piperidinium chloride, and N-methyl-N-hexyl-piperidinium chloride; specific examples of pyrrolidinium salts include N,N-dimethyl-pyrrolidinium chloride, N-methyl-N-ethyl-pyrrolidinium chloride, N-methyl-N-butyl-pyrrolidinium chloride, and and N-methyl-N-hexyl-pyrrolidinium chloride, specific examples of piperazinium monosalts include N,N,N'-trimethyl-piperazinium chloride, N,N'-dimethyl-N-ethyl-piperazinium chloride, N,N'-dimethyl-N-butyl-piperazinium chloride, and N,N'-dimethyl-N-hexyl-piperazinium chloride, and specific examples of piperazinium disalts include N,N,N',N'-tetramethyl-piperazinium dichloride, N,N'-dimethyl-N,N'-diethyl-piperazinium dichloride, N,N'-dimethyl-N,N'-dibutyl-piperazinium dichloride, and N,N'-dimethyl-N,N'-dihexyl-piperazinium chloride.

[0092] According to embodiments of the present invention, the P-heterocyclic ionic liquid can be selected from aromatic P-heterocyclic ionic liquids and non-aromatic P-heterocyclic ionic liquids. Exemplary aromatic P-heterocyclic ionic liquids according to embodiments of the present invention are phosphorium salts (containing a five-membered ring with one P heteroatom) and phosphininium salts (containing a six-membered ring with one P heteroatom), and are exemplified by the following specific structures: [ka]

[0093] Examples of non-aromatic P-heterocyclic ionic liquids according to embodiments are ionic liquids selected from phosphoranium salts (containing a saturated five-membered ring with one P heteroatom) and phosphinium salts (containing a saturated six-membered ring with one P heteroatom).

[0094] The general structure of a phosphoranium salt is [ka] R in the formula 18 and R 19 is an organyl residue, preferably a C1-C12 alkyl residue, and Z is any kind of anion, preferably chloride, bromide, acetate, trifluoroacetate, OTf (trifluoromethanesulfonate), MeSO3 (methanesulfonate), TFSI (bis(trifluoromethylsulfonyl)imide), tetrafluoroborate, or hexafluorophosphate or methylsulfonate;

[0095] The general structure of a phosphinnium salt is [ka] R in the formula 20 and R 21 is an organyl residue, preferably a C1-C12 alkyl residue, and Z is any kind of anion, preferably chloride, bromide, acetate, trifluoroacetate, OTf (trifluoromethanesulfonate), MeSO3 (methanesulfonate), TFSI (bis(trifluoromethylsulfonyl)imide), tetrafluoroborate, or hexafluorophosphate or methylsulfonate.

[0096] According to embodiments of the present invention, each of the structures shown above may also bear further substituents on the carbon ring atoms, preferably halogen and alkyl substituents.

[0097] Specific examples of phosphonium salts include P,P-dimethyl-phosphoranium chloride and P-methyl-P-butyl-phosphoranium chloride (5-membered ring), and specific examples of phosphinium salts include P,P-dimethyl-phosphinium chloride (6-membered ring) and P-methyl-P-butyl-phosphinium chloride (6-membered ring).

[0098] According to an embodiment of the present invention, it is preferred that the cation of the ionic liquid comprises a heterocyclic structure. The anion of the ionic liquid compound can be selected from any type of organic and inorganic anion, where monovalent cations are preferred.

[0099] An example of an anion of an ionic liquid compound is F - , Cl - , Br - , I - , AlCl4 - , heptachlorodialuminate (Al2Cl7 - ), hexafluoroantimonate, hexafluoroarsenate, fluorosulfonate, hexafluorophosphate (PF6 - ), tetrafluoroborate (BF4 - ), bis-perfluoroalkylsulfonylamides (especially methyl, butyl and nonyl, more particularly bis(trifluoromethylsulfonyl)imide (NTf2 - 、 TFSI), and perfluoroalkylsulfonates (especially trifluoromethanesulfonate), tetrachloroborates, dicyanamide anion (DCA - ), acetate, trifluoroacetate, methanesulfonate, tetrafluoroborate, hexafluorophosphate, lactate, citrate, sulfate, phosphate, methyl sulfate, ethyl sulfate, hydrogen sulfate, carbonate, and methyl carbonate.

[0100] Preferably, the anion is selected from chloride, bromide, acetate, trifluoroacetate, OTf (trifluoromethanesulfonate), MeSO3 (methanesulfonate), TFSI (bis(trifluoromethylsulfonyl)imide), tetrafluoroborate, or hexafluorophosphate, more preferably selected from chloride, tetrafluoroborate (BF4), hexafluorophosphate (PF6), bis-trifluoromethanesulfonimide (NTf2), and trifluoromethanesulfonate (OTf).

[0101] To obtain a high proportion of a particular partially hydrogenated halosilane, the addition of a metal hydride provides a substoichiometric amount of hydride ion. In parallel with and / or following the reduction reaction, a mixture of products is formed by an equilibration process involving a redispersion reaction of the compound (A) formed in the process and the starting material (B) present in the reaction mixture.

[0102] As defined herein, the term "redispersion reaction" refers to the redispersion of hydrogen and halogen substituents, preferably hydrogen and chlorine substituents, attached to the silicon atoms of one or more silane compounds by exchange of these substituents. This exchange is in particular 29 It can be monitored by Si NMR, GC, and / or GC / MS. Preferably, by redispersing silanes in which the silicon atoms have mostly or exclusively chlorine atoms as substituents in addition to organyl substituents, and silanes in which the silicon atoms have mostly or exclusively hydrogen substituents as substituents in addition to organyl substituents, organohydridohalosilanes having hydrogen and halogen substituents, preferably hydrogen and chlorine substituents, on the silicon atoms are obtained.

[0103] As defined herein, the silane redispersion reaction specifically involves the compromising of two different organosilanes (specifically one having only halogens as additional substituents and the other having only hydrogens as additional substituents) to form one specific halohydridoorganosilane, e.g. Me2SiCl2+Me2SiH2→ 2Me2SiHCl 2MeSiCl3 + MeSiH3 → 3MeSiHCl2

[0104] This redispersion reaction may be considered the reverse of the undesired disproportionation in which, for example, chlorohydridomethylsilane reacts with itself to form two different methylsilanes (one with only chlorine as an additional substituent and the other with only hydrogen as an additional substituent): 2Me2SiHCl → Me2SiCl2+Me2SiH2 3MeSiHCl2 → 2MeSiCl3 + MeSiH3

[0105] The redispersion reaction is catalyzed or facilitated by one or more heterocyclic ionic liquids, and although the presence of additional, different redispersion catalysts is included within the scope of the process of the present invention, in preferred embodiments no additional redispersion catalysts are added beyond the heterocyclic ionic liquid.

[0106] As mentioned above, the starting material for the process according to the present invention is a silane compound (B) having at least one Si-X bond, which includes monosilanes, disilanes, carbodisilanes and polysilanes, wherein the silane compound may or may not also contain organyl substituents. The term "organyl" is defined herein to refer to any organic substituent, regardless of functionality, bonded to the silicon atom of compound (B) via its carbon atom; according to an embodiment of the present invention, the organyl group is preferably a substituted or unsubstituted, more preferably an unsubstituted, group selected from the group consisting of alkyl, aryl, alkenyl, alkynyl, alkaryl, aralkyl, aralkenyl, aralkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, cycloaralkyl, cycloaralkenyl, and cycloaralkynyl groups; even more preferably selected from alkyl, cycloalkyl, alkenyl, and aryl groups; even more preferably selected from methyl, ethyl, vinyl, and phenyl groups; and most preferably R is a methyl group (hereinafter also abbreviated as Me).

[0107] According to an embodiment of the present invention, the process preferably results in the formation of one or more halohydridoorganomonosilanes, particularly the chlorohydridoorganomonosilanes R2SiHCl, RSiH2Cl, and RSiHCl2.

[0108] These compounds are very attractive and valuable due to their bifunctional nature, making them useful as reagents in synthesis. The most preferred silane compounds (A) having at least one Si-H bond obtained in the process according to embodiments of the present invention are Me2SiHCl, MeSiH2Cl, and MeSiHCl2.

[0109] The difunctional halohydridoorganomonosilane compounds described above are generally obtained by subjecting the monosilanes (B) described above to the process of the present invention, but in embodiments the process is also suitable for obtaining organohydridohalomonosilanes by subjecting the corresponding disilanes, polysilanes, and carbodisilanes (B) described above to the process.

[0110] This requires that a cleavage reaction be carried out in a process according to an embodiment of the present invention.

[0111] The term "cleavage reaction" is used above to indicate the transformation in which disilanes (B), polysilanes (B), and carbodisilanes (B) react to produce monosilanes (A). In the case of disilanes and polysilanes, the term "cleavage reaction" further indicates that, according to the present invention, the cleavage of the aforementioned materials occurs by breaking the bonds connecting the silicon atoms of the disilanes and polysilanes, or their fully or partially hydrogenated derivatives. In the case of carbodisilanes, the term "cleavage reaction" indicates that the cleavage reaction in carbodisilanes occurs by breaking one or both of the Si-C bonds between the silyl group and the methylene or ethylene group connecting the silyl group. To facilitate the cleavage reaction described above, an additional cleavage promoter or cleavage catalyst may be added to the reaction mixture of processes according to embodiments of the present invention.

[0112] Such cleavage promoters or catalysts are preferably selected from the group consisting of: Group-15 quaternary onium compounds R4QX, where each R is independently hydrogen or an organyl group, Q is nitrogen, phosphorus, arsenic, antimony, or bismuth, and X is a halide selected from the group consisting of F, Cl, Br, and I; heterocyclic amines, heterocyclic ammonium halides, - a mixture of R3P and RX, wherein R is as defined above and X is as defined above. alkali metal halides, alkaline earth metal halides, alkali metal hydrides, -Alkaline earth metal hydrides, or mixtures thereof.

[0113] However, according to an embodiment of the present invention, it is preferred that no further cleavage catalysts or cleavage promoters are added in addition to the heterocyclic ionic liquids applied in the process according to the present invention.

[0114] Generally, the type of compound (A) having at least one Si-H bond is determined by the silane starting material (B) and the amount of metal hydride reacted with the silane starting material (B). Furthermore, when cleavage of disilanes and polysilanes is involved, the type of monosilane (A) obtained is essentially determined by the substitution pattern of the disilanes and polysilanes and the amount of metal hydride used.

[0115] In the most preferred embodiment of the present invention, MeSiCl is subjected to reaction with CaH in the presence of one or more heterocyclic ionic liquids at a temperature of from about 0° C. to about 150° C., thus producing MeSiHCl, wherein the heterocyclic ionic liquid is preferably selected from N-heterocyclic aromatic quaternary ammonium ionic liquids, more preferably from imidazolium salts, even more preferably from 1-substituted imidazolium salts, even more preferably from 1-alkyl-3-methylimidazolium chlorides, and most preferably from ethyl MIMCl, butyl MIMCl, and hexyl MIMCl.

[0116] In an embodiment according to the present invention, each X is selected from a chlorine atom, a bromine atom or an iodine atom, preferably selected from a chlorine atom, more preferably all X in compound (B) are chlorine atoms.

[0117] The Si-Cl, Si-Br, and Si-I bonds can be readily replaced in processes according to embodiments of the present invention by contacting a silane compound (B) having one or more Si-X bonds with a metal hydride in the presence of a heterocyclic ionic liquid. Preferably, at least one X in silane compound (B) represents a chlorine atom, and more preferably all substituents X in silane compound (B) are chlorine atoms.

[0118] In an embodiment according to the present invention, the compound (A) having at least one Si—H bond is an organomonosilane compound, preferably an organohydridochloromonosilane.

[0119] The target compound according to this embodiment is a monosilane bearing one or more organyl groups R and one or more hydride substituents.

[0120] Organohydridomonosilanes having the formulae RSiH, RSiH, and RSiH, and organohydridohalosilanes having the formulae RSiXH, RSiXH, and RSiXH, both of which are produced by this embodiment of the invention, wherein the substituents R are independently selected from organyl groups, preferably C-C alkyl groups or phenyl groups, more preferably methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, or phenyl groups, and most preferably methyl and phenyl groups.

[0121] According to an embodiment, X is independently selected from F, Cl, Br or I substituents, preferably each X represents a Cl atom.

[0122] In some embodiments, the compound (A) having at least one Si-H bond is preferably an organohydridochloromonosilane, i.e., an organomonosilane bearing one or more hydrogen atoms and one or more chlorine atoms as substituents. Thus, preferred target compounds (A) have the general formulas RSiH2Cl, RSiHCl2, and R2SiHCl, where R is independently selected from organyl groups, preferably C1-C12 alkyl groups or phenyl groups, more preferably methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, or phenyl groups, and most preferably methyl and phenyl groups. In the case of silane compounds (A) of formula R2SiHCl, it is preferred that both R represent the same substituent, most preferably methyl groups. Organohydridochloromonosilanes, bearing one or more organyl groups R, one or more hydrido substituents, and one or more chloro substituents, are useful building blocks in synthetic silicon chemistry because they exhibit bifunctional substitution.

[0123] The most preferred target compounds (A) according to the embodiment are MeSiH2Cl, MeSiHCl2 and Me2SiHCl.

[0124] In an embodiment according to the present invention, the compound (B) having at least one Si-X bond is an organosilane compound, preferably an organoperchlorosilane, more preferably an organoperchloromonosilane compound. Starting materials (B) according to embodiments thus include monosilanes, disilanes, polysilanes, and carbodisilanes having one or more groups R and at least one halo group X bonded to one or more of the compound's Si atoms. In the process according to this embodiment, any type of organosilane having one or more Si-X bonds, including organohydridohalosilanes (B), can be further hydrogenated by contacting the silane compound (B) with a metal hydride.

[0125] According to an embodiment, the groups R of silane compound (B) are independently selected from optionally substituted, preferably unsubstituted, alkyl, aryl, alkenyl, alkynyl, alkaryl, aralkyl, aralkenyl, aralkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, cycloaralkyl, cycloaralkenyl, and cycloaralkynyl groups, more preferably alkyl, cycloalkyl, alkenyl, and aryl groups, even more preferably methyl, vinyl, and phenyl groups, and most preferably R is a methyl group. Preferably, compound (B) having at least one Si-X bond is an organoperchlorosilane, i.e., all substituents other than organyl groups of silane compound (B) are chloro substituents. Preferred monosilanes according to embodiments have the general formula RSiCl3, R2SiCl2 and R3SiCl, preferred disilanes have the general formula RCl2Si-Si-RCl2, R2ClSi-SiRCl2 and R2ClSi-SiR2Cl, and preferred polysilanes have the general formula ClR2Si-SiR2-SiR2Cl, ClR2Si-SiR2-SiR2-SiR2Cl, (ClR2Si)3SiR, (Cl2RSi)2SiRCl, (Cl2RSi)3SiR, (Cl2RSi)2SiR-SiClR-SiCl2R, [(Cl2RSi)2SiR]2, [ (ClRSi)SiR]SiClR, and (ClRSi)SiR—SiRCl, and preferred carbodisilanes have the general formula ClRSi—CH—SiRCl, ClRSi—CH—SiRCl, ClRSi—CH—SiRCl, RSi—CH—SiRClRSi—CH—SiRCl, RClSiCHCHSiCl, RClSiCHCHSiCl, ClSiCHCHSiCl, RClSiCHCHCHSiRCl, and RClSiCHCHSiRCl.

[0126] Preferred examples of compound (B) having at least one Si-X bond according to an embodiment of the present invention include MeSiCl, MeSiCl, MeSiCl, ClMeSi-SiMeCl, ClMeSi-SiMeCl, ClMeSi-SiMeCl, ClMeSi-SiMe3, ClMeSi-SiMe2Cl, MeSi-SiMe2Cl, ClMeSi-SiMe2-SiMe2Cl, ClMeSi-SiMe2-SiMe2Cl, ClMeSi-SiMe2-SiMe2Cl, (ClMeSi)SiMe, (ClMeSi)SiMeCl, (ClMeSi)SiMe, (ClMeSi)SiMe-SiClMe-SiCl 2Me, [(Cl2MeSi)2SiMe]2, [(Cl2MeSi)2SiMe]2SiClMe, (Cl2MeSi)2SiMe-SiMe2Cl, Cl2MeSi-CH2-SiMeCl2, ClMe2Si-CH2-SiMeCl2, ClMe2Si-CH2-SiMe2Cl, Me3Si-CH2-SiMeCl2, Me3Si-CH2-SiMe2Cl, Me2ClSiCH2CH2SiCl3, MeCl2SiCH2CH2SiCl3, Cl3SiCH2CH2SiCl3, Me2ClSiCH2CH2SiMe2Cl, and Me2ClSiCH2CH2SiMeCl2.

[0127] More preferably, compound (B) is an organoperchloromonosilane compound, and most preferably compound (B) is selected from Me2SiCl2 and MeCl3, especially Me2SiCl2.

[0128] In an embodiment according to the invention, the product (A) is selected from monosilanes of the following general formula (I): R x SiH y Cl z (I) In the formula, R is an organyl group, x=0 to 3, preferably 0, 1, 2 and 3; y=1 to 4, preferably 1 to 2, most preferably 1; z=0 to 3, preferably 0, 1, 2 and 3, and x+y+z=4.

[0129] Monosilane (A) in accordance with the present invention is a chlorosilane that does not carry any organyl group R, i.e., x=0 in general formula (I). Preferred halomonosilanes in accordance with the present invention are SiCl, SiBr, SiI, HSiCl, HSiBr, and HSiI, with SiCl and HSiCl being most preferred. Most preferred is when monosilane (A) is an organomonosilane, x is 1 to 3, even more preferably 1 or 2, and y is preferably 1 or 2. Preferred organomonosilanes in accordance with the present invention are RSiHCl, RSiHCl, and RSiHCl. Preferably, the organyl group R is selected from methyl, ethyl, phenyl, and vinyl. Most preferred monosilane products (A) are MeSiHCl, MeSiHCl, and MeSiHCl.

[0130] In an embodiment according to the invention, the product (A) is selected from monosilanes of the following general formula (I): R x SiH y Cl z (I) In the formula, R is an organyl group, x=1 to 3, preferably 1 to 2, y=1 to 3, preferably 1 to 2, z=0 to 2, preferably 1 to 2, and x+y+z=4.

[0131] Preferred organomonosilanes according to this embodiment are R2SiHCl, RSiH2Cl, and RSiHCl2. Preferably, the organyl group R is selected from methyl, ethyl, phenyl, and vinyl groups. The most preferred monosilane products (A) are Me2SiHCl, MeSiHCl2, and MeSiH2Cl.

[0132] In an embodiment according to the invention, the compound (B) having at least one Si-X bond is selected from organochloromonosilanes of the following general formula (II): R a SiH b Cl c(II) wherein R is as defined above; a=1 to 3, b=0 to 2, c=1 to 3, and a+b+c=4.

[0133] Preferably, a = 1 or 2 and b = 0, i.e., the starting material is a monosilane bearing only one or two organyl groups and chlorine substituents. More preferably, the organyl group R is selected from methyl, ethyl, phenyl, and vinyl groups. The most preferred monosilane starting materials (B) are Me2SiCl2 and MeSiCl3.

[0134] In an embodiment according to the present invention, the organyl groups R are independently selected from alkyl, cycloalkyl or phenyl groups, preferably R represents a methyl group.

[0135] Preferably, all R groups in organosilanes (A) containing one or more Si-X bonds or organosilanes (A) containing one or more Si-H bonds are selected from the same type of group: alkyl, cycloalkyl, or phenyl, more preferably C-C alkyl, C-C cycloalkyl, and phenyl, and most preferably methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopentyl, cyclohexyl, and phenyl. Most preferably, all R groups are methyl, and therefore the most preferred organosilanes (B) according to this embodiment are MeSiCl and MeSiCl, and correspondingly, the most preferred organosilanes (A) according to this embodiment are MeSiHCl, MeSiHCl, and MeSiHCl.

[0136] In an embodiment according to the invention, compound (A) is selected from Me2SiHCl, MeSiH2Cl, MeSiHCl2, Me2SiHCl, HSiCl3 and Me3SiH, preferably compound (A) is Me2SiHCl.

[0137] Methylhydridomonosilanes, especially methylhydridomonosilanes, are particularly useful reagents, and thus providing such compounds in a sustainable, cost-effective, and resource-efficient manner is of great interest. According to this embodiment, the analogous methylchloromonosilanes MeSiCl, MeSiCl, and MeSiCl are each preferably reacted with one or more metal hydrides (C) in the presence of one or more heterocyclic ionic liquids, preferably using CaH as the metal hydride, and more preferably using a heterocyclic ionic liquid selected from the group of N-containing aromatic quaternary ammonium compounds, to provide the methylhydridomonosilanes (A), MeSiHCl, MeSiHCl, HSiCl, and MeSiH.

[0138] In an embodiment according to the invention, compound (B) is selected from Me2SiCl2, MeSiCl3, SiCl4 and Me3SiCl, preferably compound (B) is Me2SiCl2.

[0139] Compound (B) according to this embodiment can be fully hydrogenated by reacting silanes with excess hydride ions from a metal hydride (C) in the presence of a heterocyclic ionic liquid without additional activation means or agents, resulting in the production of silane products (A), MeSiH, MeSiH, and MeSiH. Preferably, compound (B) according to this embodiment is reacted with less than a stoichiometric amount of hydride ions from a metal hydride (C), resulting in partial substitution of the Si-X bond of the starting material, with the most preferred products being MeSiHCl, MeSiHCl, and MeSiHCl. The presence of a heterocyclic ionic liquid allows this reaction to occur without additional activation means or agents and also allows for the reduction of the respective amounts of starting material (B) and its superhydrogenated analogs, MeSiH, MeSiH, and MeSiH, relative to the desired organohydridochlorosilane through equilibrated redistribution of chlorine and hydrogen atoms.

[0140] In an embodiment according to the present invention, the metal hydride (C) is selected from an alkali metal hydride, an alkaline earth metal hydride, or a complex metal hydride comprising an alkali metal cation or an alkaline earth metal cation, preferably the metal hydride (C) is selected from LiH, NaH, KH, MgH2, CaH2 and LiAlH4, most preferably the metal hydride (C) is CaH2. Preferably, the metal hydride (C) according to an embodiment of the present invention is selected from a divalent metal hydride, more preferably an alkali metal hydride and an alkaline earth metal hydride, even more preferably selected from the group of lithium hydride, sodium hydride, potassium hydride, magnesium hydride, calcium hydride, even more preferably selected from calcium hydride and magnesium hydride, most preferably the metal hydride (C) is calcium hydride.

[0141] While the reaction of a silane compound having one or more Si-X bonds with a metal hydride often requires activation by activation means such as sonication, milling, or the addition of an activating agent, compound (B) can be readily converted to the desired product (A) by contacting the metal hydride with silane (B) in the presence of a heterocyclic ionic liquid. This allows the process to be carried out using relatively low-cost hydrides such as NaH, KH, MgH, and CaH, particularly CaH. While the form of the metal hydride (C) is not critical, it is preferred in some embodiments that the metal hydride be added to the reaction mixture as a finely divided powder or a slurry of such powder. The heterocyclic ionic liquid facilitates the reaction by removing passivating layers of metal oxides, particularly metal halides formed in the reaction with halosilanes, from the surface of the metal hydride particles.

[0142] In a further embodiment according to the invention, the process is carried out without any metal hydride reagent (C) except for CaH2.

[0143] As already mentioned above, it is preferred to use calcium hydride as the metal hydride (C) because this hydride is readily available at low cost. In the presence of the heterocyclic ionic liquid, no additional metal hydride reagent (C) is required, which further improves the cost-effectiveness of the process for producing one or more silane compounds (A) having at least one Si-H bond.

[0144] In an embodiment according to the invention, the molar ratio of hydride ions of one or more metal hydrides to halogen atoms, preferably chlorine atoms, of one or more compounds (B) in the reaction mixture is in the range of from about 0.01 to about 300, more preferably from about 0.1 to about 10, even more preferably from about 0.4 to about 6, and most preferably from about 0.7 to about 3.

[0145] As previously mentioned, the amount of metal hydride (C) providing the hydride ions relative to the halogen atoms added is determined by whether complete replacement of all Si-X bonds with Si-H bonds is desired and whether there will be further consumption of hydride ions, for example, by reaction with another compound outside the definition of silane compound (B) in the reaction mixture.

[0146] In an embodiment according to the present invention, the heterocyclic ionic liquid is selected from the group consisting of N-heterocyclic ionic liquids and P-heterocyclic ionic liquids.

[0147] According to the present invention, N-heterocyclic ionic liquids and P-heterocyclic ionic liquids are heterocyclic ionic liquids as defined above, where the heterocycle of the ionic liquid compound is a P-heterocycle, i.e., a cyclic structure containing a P-atom as a ring member, or an N-heterocycle, i.e., a cyclic structure containing an N-atom as a ring member. The P-heterocycle or N-heterocycle, respectively, can be present in the cation, the anion, or both the cation and the anion of the ionic liquid, but preferably the cation of the ionic liquid contains the P-heterocycle or N-heterocycle.

[0148] In an embodiment according to the present invention, the heterocyclic ionic liquid is selected from the group consisting of N-heterocyclic aromatic ionic liquids and P-heterocyclic aromatic ionic liquids.

[0149] The N- or P-heterocyclic ionic liquid compounds according to this embodiment each contain one or more aromatic moieties. Preferably, the aromatic structure of the N- or P-heterocyclic compound is a heterocyclic structure. Exemplary N-heterocyclic aromatic ionic liquids according to embodiments are ionic liquids selected from imidazolium salts, pyridinium salts, and triazolium salts, and exemplary P-heterocyclic aromatic ionic liquids according to embodiments are ionic liquids selected from phosphorium salts and phosphininium salts.

[0150] In an embodiment according to the present invention, the heterocyclic ionic liquid is selected from the group consisting of N-heterocyclic quaternary ammonium ionic liquids and P-heterocyclic phosphonium ionic liquids.

[0151] According to this embodiment, each N- or P-heterocyclic ionic liquid compound contains one or more quaternary ammonium or phosphonium groups, respectively. Typically, the quaternary structure of the N- or P-heterocyclic compound is located in the heterocyclic structure, i.e., the quaternary N- or P-atom is part of the ring structure. N-heterocyclic quaternary ammonium ionic liquids may be selected from, for example, pyridinium salts, imidazolium salts, 1,2,3-triazolium salts, imidazolinium salts, pyrrolium salts, morpholinium salts, piperidinium salts, piperazinium salts, and pyrrolidinium salts.

[0152] Preferred P-heterocyclic ionic liquid compounds according to this embodiment are phosphoranium salts of the general formula: [ka] R in the formula 18 and R 19are independently selected from methyl, ethyl, butyl, hexyl, and octyl residues, preferably R 18 is a methyl or butyl residue, and R 19 is selected from methyl, ethyl, butyl, hexyl, and octyl residues, more preferably R 18 is a methyl or butyl residue, and R 19 is selected from a methyl, ethyl, or butyl residue, most preferably R 18 and R 19 are independently methyl and butyl residues, and Z is preferably selected from chloride, bromide, acetate, trifluoroacetate, tetrafluoroborate, hexafluorophosphate or methylsulfonate anions, most preferably Z is chloride anion. Optionally, the P,P-substituted phosphoranium salts can carry one or more further C1-C12 alkyl substituents on one or more of the ring carbon atoms, preferably they can further carry one further methyl, ethyl, butyl, hexyl and octyl residue, more preferably a methyl, ethyl or butyl residue, on the 2-C, 3-C or 4-C atom of the ring.

[0153] Particularly preferred P,P-substituted phosphoranium compounds are 1,1-dimethyl-phosphoranium chloride, 1-ethyl-1-methyl-phosphoranium chloride, 1-butyl-1-methyl-phosphoranium chloride, 1-hexyl-1-methyl-phosphoranium chloride, 1-octyl-1-methyl-phosphoranium chloride, 1-butyl-1-ethyl-phosphoranium chloride, 1,1-dibutyl-phosphoranium chloride, 1-hexyl-1-butyl-phosphoranium chloride, and 1-octyl-1-butyl-phosphoranium chloride.

[0154] Another class of preferred P-heterocyclic ionic liquid compounds according to this embodiment are phosphinnium salts of the general formula: [ka] R in the formula 20 and R 21 are independently selected from methyl, ethyl, butyl, hexyl, and octyl residues, preferably R 20 is a methyl or butyl residue, and R 21 is selected from methyl, ethyl, butyl, hexyl, and octyl residues, more preferably R 20 is selected from a methyl or butyl residue, and R 21 is a methyl, ethyl or butyl residue, most preferably R 20 and R 21 are independently selected from methyl and butyl residues, and Z is preferably selected from chloride, bromide, acetate, trifluoroacetate, tetrafluoroborate, hexafluorophosphate or methylsulfonate anions, most preferably Z is a chloride anion. Optionally, the P,P-substituted phosphinanium salts can carry one or more further C1-C12 alkyl substituents on one or more of the ring carbon atoms, preferably they can further carry one further methyl, ethyl, butyl, hexyl, and octyl residue, more preferably a methyl, ethyl, or butyl residue, on the 2-C, 3-C, or 4-C atom of the ring. Specifically preferred P,P-substituted phosphinanium compounds are 1,1-dimethyl-phosphinanium chloride, 1-ethyl-1-methyl-phosphinanium chloride, 1-butyl-1-methyl-phosphinanium chloride, 1-hexyl-1-methyl-phosphinanium chloride, 1-octyl-1-methyl-phosphinanium chloride, 1-butyl-1-ethyl-phosphinanium chloride, 1,1-dibutyl-phosphinanium chloride, 1-hexyl-1-butyl-phosphinanium chloride, and 1-octyl-1-butyl-phosphinanium chloride.

[0155] In an embodiment of the present invention, the heterocyclic ionic liquid is selected from the group consisting of N-heterocyclic aromatic quaternary ammonium ionic liquids and P-heterocyclic aromatic quaternary phosphonium ionic liquids.

[0156] In an embodiment according to the present invention, the heterocyclic ionic liquid is selected from the group consisting of aromatic heterocyclic quaternary ammonium salts, including pyridinium salts, imidazolium salts, 1,2,3-triazolium salts, imidazolinium salts, and pyrrolium salts; non-aromatic heterocyclic quaternary ammonium salts, including morpholinium salts, piperidinium salts, piperazinium salts, and pyrrolidinium salts; and aromatic heterocyclic quaternary phosphonium salts, including phosphininium salts. Preferably, the counter anion in the aromatic heterocyclic quaternary ammonium salt-based ionic liquid, non-aromatic heterocyclic quaternary ammonium salt-based ionic liquid, or aromatic heterocyclic quaternary phosphonium salt-based ionic liquid is selected from chloride, bromide, acetate, trifluoroacetate, tetrafluoroborate, hexafluorophosphate, or methylsulfonate, and most preferably chloride, bromide, or tetrafluoroborate.

[0157] According to an embodiment, preferred 1,2,3-triazolium salts are 1,3-substituted 1,2,3-triazolium salts of the following general formula: [ka] R in the formula 6 and R 7 are independently selected from methyl, ethyl, butyl, hexyl, and octyl residues, preferably R 6 is a methyl or butyl residue, and R 7 is selected from methyl, ethyl, butyl, hexyl, and octyl residues, more preferably R 6 is a methyl or butyl residue, and R 7 is selected from methyl, ethyl or butyl residues, most preferably R 6 and R7are independently selected from methyl and butyl residues, and Z is preferably selected from chloride, bromide, acetate, trifluoroacetate, tetrafluoroborate, hexafluorophosphate or methylsulfonate anions, most preferably Z is a chloride anion. Optionally, the 1,3-substituted 1,2,3-triazolium salts can carry one or more additional C1-C12 alkyl substituents on one or more of the ring carbon atoms, preferably they further carry one additional methyl, ethyl, butyl, hexyl, and octyl residue, more preferably a methyl, ethyl, or butyl residue on the 4-C atom of the ring. Specific preferred 1,3-substituted 1,2,3-triazolium compounds are 1-methyl-3-methyl-1,2,3-triazolium chloride, 1-ethyl-3-methyl-1,2,3-triazolium chloride, 1-butyl-3-methyl-1,2,3-triazolium chloride, 1-hexyl-3-methyl-1,2,3-triazolium chloride, 1-octyl-3-methyl-1,2,3-triazolium chloride, 1-butyl-3-ethyl-1,2,3-triazolium chloride, 1-butyl-3-butyl-1,2,3-triazolium chloride, 1-hexyl-3-butyl-1,2,3-triazolium chloride, and 1-octyl-3-butyl-1,2,3-triazolium chloride.Particularly preferred 1,3-substituted 1,2,3-triazolium compounds carrying further substituents on the ring C-atoms are 1-methyl-3-methyl-4-methyl-1,2,3-triazolium chloride, 1-ethyl-3-methyl-4-methyl-1,2,3-triazolium chloride, 1-butyl-3-methyl-4-methyl-1,2,3-triazolium chloride, 1-butyl-3-ethyl-4-methyl-1,2,3-triazolium chloride, 1-butyl-3-butyl-4-methyl-1,2,3-triazolium chloride, The compounds are 1-methyl-4-methyl-1,2,3-triazolium chloride, 1-methyl-3-methyl-4-butyl-1,2,3-triazolium chloride, 1-ethyl-3-methyl-4-butyl-1,2,3-triazolium chloride, 1-butyl-3-methyl-4-butyl-triazolium chloride, 1-butyl-3-ethyl-4-butyl-1,2,3-triazolium chloride, and 1-butyl-3-butyl-4-butyl-1,2,3-triazolium chloride.

[0158] According to an embodiment, preferred pyrrolium salts are N,N-alkylpyrrolium salts of the general formula: [ka] R in the formula 4 and R 5 are independently selected from methyl, ethyl, butyl, hexyl, and octyl residues, preferably R 4 is selected from a methyl or butyl residue, and R 5 is selected from methyl, ethyl, butyl, hexyl, and octyl residues, more preferably R 4 is selected from a methyl or butyl residue, and R 5 is selected from a methyl, ethyl, or butyl residue, most preferably R 4 and R 5are independently selected from methyl and butyl residues, and Z is preferably selected from chloride, bromide, acetate, trifluoroacetate, tetrafluoroborate, hexafluorophosphate or methylsulfonate anions, most preferably Z is chloride anion. Optionally, the N,N-substituted pyrrolium salts can carry one or more additional C1-C12 alkyl substituents on one or more of the ring carbon atoms, preferably they further have one methyl, ethyl, butyl, hexyl, and octyl residue, more preferably a methyl, ethyl or butyl residue on the 2-C or 3-C atom of the ring. Specifically preferred N,N-substituted pyrrolium compounds are 1,1-dimethyl-pyrrolium chloride, 1-ethyl-1-methyl-pyrrolium chloride, 1-butyl-1-methyl-pyrrolium chloride, 1-hexyl-1-methyl-pyrrolium chloride, 1-octyl-1-methyl-pyrrolium chloride, 1-butyl-1-ethyl-pyrrolium chloride, 1,1-dibutyl-pyrrolium chloride, 1-hexyl-1-butyl-pyrrolium chloride, and 1-octyl-1-butyl-pyrrolium chloride.Particularly preferred N,N-substituted pyrrolium compounds carrying a further substituent on the 2-C atom of the ring are 1,1,2-trimethyl-pyrrolium chloride, 1-ethyl-1,2-dimethyl-pyrrolium chloride, 1-butyl-1,2-dimethyl-pyrrolium chloride, 1-hexyl-1,2-dimethyl-pyrrolium chloride, 1-octyl-1,2-dimethyl-pyrrolium chloride, 1-butyl-1-ethyl-2-methyl-pyrrolium chloride, 1,1-dibutyl-2-methyl-pyrrolium chloride, 1-hexyl-1-butyl-2-methyl-pyrrolium chloride and 1-octyl-1- butyl-2-methyl-pyrrolium chloride, 1,1-dimethyl-2-butyl-pyrrolium chloride, 1-ethyl-1-methyl-2-butyl-pyrrolium chloride, 1,2-dibutyl-1-methyl-pyrrolium chloride, 1-hexyl-1-methyl-2-butyl-pyrrolium chloride, 1-octyl-1-methyl-2-butyl-pyrrolium chloride, 1,2-dibutyl-1-ethyl-pyrrolium chloride, 1,1,2-tributyl-pyrrolium chloride, 1-hexyl-1,2-dibutyl-pyrrolium chloride, and 1-octyl-1,2-dibutyl-pyrrolium chloride.Particularly preferred N,N-substituted pyrrolium compounds carrying a further substituent on the 3-C atom of the ring are 1,1,3-trimethyl-pyrrolium chloride, 1-ethyl-1,3-dimethyl-pyrrolium chloride, 1-butyl-1,3-dimethyl-pyrrolium chloride, 1-hexyl-1,3-dimethyl-pyrrolium chloride, 1-octyl-1,3-dimethyl-pyrrolium chloride, 1-butyl-1-ethyl-3-methyl-pyrrolium chloride, 1,1-dibutyl-3-methyl-pyrrolium chloride, 1-hexyl-1-butyl-3-methyl-pyrrolium chloride and 1-octyl-1- butyl-3-methyl-pyrrolium chloride, 1,1-dimethyl-3-butyl-pyrrolium chloride, 1-ethyl-1-methyl-3-butyl-pyrrolium chloride, 1,3-dibutyl-1-methyl-pyrrolium chloride, 1-hexyl-1-methyl-3-butyl-pyrrolium chloride, 1-octyl-1-methyl-3-butyl-pyrrolium chloride, 1,3-dibutyl-1-ethyl-pyrrolium chloride, 1,1,3-tributyl-pyrrolium chloride, 1-hexyl-1,3-dibutyl-pyrrolium chloride, and 1-octyl-1,3-dibutyl-pyrrolium chloride.

[0159] Preferred N,N-morpholinium salts according to embodiments are N,N-alkylmorpholinium salts of the general formula: [ka] R in the formula 8 and R 9 are independently selected from methyl, ethyl, butyl, hexyl, and octyl residues, preferably R 8 is a methyl or butyl residue, and R 9 is selected from methyl, ethyl, butyl, hexyl, and octyl residues, more preferably R 8 is selected from a methyl or butyl residue, and R 9 is selected from a methyl, ethyl or butyl residue, most preferably R 8 and R 9are independently selected from methyl and butyl residues, and Z is preferably selected from chloride, bromide, acetate, trifluoroacetate, tetrafluoroborate, hexafluorophosphate or methylsulfonate anions, most preferably Z is chloride anion. Optionally, the N,N-substituted morpholinium salts can carry one or more additional C1-C12 alkyl substituents on one or more of the ring carbon atoms, preferably they further carry one additional methyl, ethyl, butyl, hexyl, and octyl residue, more preferably a methyl, ethyl or butyl residue on the 2-C or 3-C atom of the ring. Specifically preferred N,N-substituted morpholinium compounds are 1,1-dimethyl-morpholinium chloride, 1-ethyl-1-methyl-morpholinium chloride, 1-butyl-1-methyl-morpholinium chloride, 1-hexyl-1-methyl-morpholinium chloride, 1-octyl-1-methyl-morpholinium chloride, 1-butyl-1-ethyl-morpholinium chloride, 1,1-dibutyl-morpholinium chloride, 1-hexyl-1-butyl-morpholinium chloride, and 1-octyl-1-butyl-morpholinium chloride.

[0160] Preferred N,N-piperidinium salts according to embodiments are N,N-alkylpiperidinium salts of the general formula: [ka] R in the formula 10 and R 11 are independently selected from methyl, ethyl, butyl, hexyl, and octyl residues, preferably R 10 is a methyl or butyl residue, and R 11 is selected from methyl, ethyl, butyl, hexyl, and octyl residues, more preferably R 10 is a methyl or butyl residue, and R 11 is a methyl, ethyl or butyl residue, most preferably R 10 and R11 are independently selected from methyl and butyl residues, and Z is preferably selected from chloride, bromide, acetate, trifluoroacetate, tetrafluoroborate, hexafluorophosphate, or methylsulfonate anions, most preferably Z is chloride anion.

[0161] Optionally, the N,N-substituted piperidinium salts can carry one or more additional C1-C12 alkyl substituents on one or more of the ring carbon atoms, preferably they further carry a methyl, ethyl, butyl, hexyl, and octyl residue, more preferably a methyl, ethyl, or butyl residue on the 2-C, 3-C, or 4-C atom of the ring. Specifically preferred N,N-substituted piperidinium compounds are 1,1-dimethyl-piperidinium chloride, 1-ethyl-1-methyl-piperidinium chloride, 1-butyl-1-methyl-piperidinium chloride, 1-hexyl-1-methyl-piperidinium chloride, 1-octyl-1-methyl-piperidinium chloride, 1-butyl-1-ethyl-piperidinium chloride, 1,1-dibutyl-piperidinium chloride, 1-hexyl-1-butyl-piperidinium chloride, and 1-octyl-1-butyl-piperidinium chloride.

[0162] Preferred N,N-pyrrolidinium salts according to embodiments are N,N-alkylpyrrolidinium salts of the general formula: [ka] R in the formula 12 and R 13 are independently selected from methyl, ethyl, butyl, hexyl, and octyl residues, preferably R 12 is a methyl or butyl residue, and R 13 is selected from methyl, ethyl, butyl, hexyl, and octyl residues, more preferably R 12 is selected from a methyl or butyl residue, and R13 is selected from a methyl, ethyl or butyl residue, most preferably R 12 and R 13 are independently selected from methyl and butyl residues, and Z is preferably selected from chloride, bromide, acetate, trifluoroacetate, tetrafluoroborate, hexafluorophosphate or methylsulfonate anions, most preferably Z is chloride anion. Optionally, the N,N-substituted pyrrolidinium salts can carry one or more additional C1-C12 alkyl substituents on one or more of the ring carbon atoms, preferably they further carry one additional methyl, ethyl, butyl, hexyl, and octyl residue, more preferably a methyl, ethyl or butyl residue on the 2-C, 3-C or 4-C atom of the ring. Specifically preferred N,N-substituted pyrrolidinium compounds are 1,1-dimethyl-pyrrolidinium chloride, 1-ethyl-1-methyl-pyrrolidinium chloride, 1-butyl-1-methyl-pyrrolidinium chloride, 1-hexyl-1-methyl-pyrrolidinium chloride, 1-octyl-1-methyl-pyrrolidinium chloride, 1-butyl-1-ethyl-pyrrolidinium chloride, 1,1-dibutyl-pyrrolidinium chloride, 1-hexyl-1-butyl-pyrrolidinium chloride, and 1-octyl-1-butyl-pyrrolidinium chloride.

[0163] Preferred piperazinium monosalts according to embodiments are N,N,N'-alkylpiperazinium monosalts of the following general formula: [ka] R in the formula 14 , R 15 and R 16 are independently selected from methyl, ethyl, butyl, hexyl, and octyl residues, preferably R 15 is selected from a methyl or butyl residue, and R 14 and R 16is selected from methyl, ethyl, butyl, hexyl, and octyl residues, more preferably R 15 is selected from a methyl or butyl residue, and R 14 and R 16 is selected from a methyl, ethyl or butyl residue, most preferably R 14 , R 15 and R 16are independently selected from methyl and butyl residues, and Z is preferably selected from chloride, bromide, acetate, trifluoroacetate, tetrafluoroborate, hexafluorophosphate, or methylsulfonate anions, most preferably Z is a chloride anion. Optionally, the N,N,N'-substituted piperazinium monosalts can carry one or more additional C1-C12 alkyl substituents on one or more of the ring carbon atoms, preferably they carry one additional methyl, ethyl, butyl, hexyl, and octyl residue, more preferably a methyl, ethyl, or butyl residue on the 2-C, 3-C, 5-C, or 6-C atom of the ring. Specific preferred N,N,N'-substituted piperazinium monosalt compounds are 1,1,4-trimethyl-piperazinium chloride, 1-ethyl-1,4-dimethyl-piperazinium chloride, 1-butyl-1,4-dimethyl-piperazinium chloride, 1-hexyl-1,4-dimethyl-piperazinium chloride, 1-octyl-1,4-dimethyl-piperazinium chloride, 1-butyl-1-ethyl-4-methyl-piperazinium chloride, 1,1-dibutyl-4-methyl-piperazinium chloride, 1-hexyl-1-butyl-4-methyl-piperazinium chloride, and 1-octyl-1-butyl-4-methyl-piperazinium chloride. ethyl-piperazinium chloride, 1,1-dimethyl-4-butyl-piperazinium chloride, 1-ethyl-1-methyl-4-butyl-piperazinium chloride, 1,4-dibutyl-1-methyl-piperazinium chloride, 1-hexyl-1-methyl-4-butyl-piperazinium chloride, 1-octyl-1-methyl-4-butyl-piperazinium chloride, 1,4-dibutyl-1-ethyl-piperazinium chloride, 1,1,4-tributyl-piperazinium chloride, 1-hexyl-1,4-dibutyl-piperazinium chloride, and 1-octyl-1,4-dibutyl-piperazinium chloride.

[0164] Preferred piperazinium di-salts according to embodiments include N,N,N',N'-alkylpiperazinium di-salts of the general formula: [ka] R in the formula 14 , R 15 , R 16 and R 17 are independently selected from methyl, ethyl, butyl, hexyl, and octyl residues, preferably R 15 and R 17 is selected from a methyl or butyl residue, and R 14 and R 16 is selected from methyl, ethyl, butyl, hexyl, and octyl residues, more preferably R 15 and R 17 is a methyl or butyl residue, and R 14 and R 16 is a methyl, ethyl or butyl residue, most preferably R 14 , R 15 , R 16 and R 17are independently selected from methyl and butyl residues, and Z is preferably selected from chloride, bromide, acetate, trifluoroacetate, tetrafluoroborate, hexafluorophosphate, or methylsulfonate anions, most preferably Z is a chloride anion. In the case of the piperazinium di-salt structures shown above, the two Z-anions together may also represent a dianion such as, for example, sulfate dianion, oxalate dianion, malonate dianion, succinate dianion, maleate dianion, fumarate dianion, tartrate dianion, or phthalate dianion. Optionally, the N,N,N',N'-substituted piperazinium di-salts can carry one or more additional C1-C12 alkyl substituents on one or more of the ring carbon atoms, preferably they carry one additional methyl, ethyl, butyl, hexyl, and octyl residue, more preferably a methyl, ethyl, or butyl residue on the 2-C, 3-C, 5-C, or 6-C atom of the ring. Specific preferred N,N,N',N'-substituted piperazinium di-salt compounds are 1,1,4,4-tetramethyl-piperazinium dichloride, 1-ethyl-1,4,4-trimethyl-piperazinium dichloride, 1-butyl-1,4,4-trimethyl-piperazinium dichloride, 1-hexyl-1,4,4-trimethyl-piperazinium dichloride, 1-octyl-1,4,4-trimethyl-piperazinium dichloride, 1-butyl-1-ethyl-4,4-dimethyl-piperazinium dichloride, 1,1-dibutyl-4,4-dimethyl-piperazinium dichloride, 1-hexyl-1-butyl 1-octyl-1-butyl-4,4-dimethyl-piperazinium dichloride, 1,1,4-trimethyl-4-butyl-piperazinium dichloride, 1-ethyl-1,4-dimethyl-4-butyl-piperazinium dichloride, 1,4-dibutyl-1,4-dimethyl-piperazinium dichloride, 1-hexyl-1,4-dimethyl-4-butyl-piperazinium dichloride, 1-octyl-1,4-dimethyl-4-butyl-piperazinium dichloride, 1,4-dibutyl-1-ethyl-4-methylpiperazinium dichloride, 1,1,4-Tributyl-4-methyl-piperazinium dichloride, 1-hexyl-1,4-dibutyl-4-methyl-piperazinium dichloride, and 1-octyl-1,4-dibutyl-4-methyl-piperazinium dichloride, 1,1,4-trimethyl-4-butyl-piperazinium dichloride, 1-ethyl-1,4-dimethyl-4-butyl-piperazinium dichloride, 1,4-dibutyl-1 ,4-Dimethyl-piperazinium dichloride, 1-hexyl-1,4-dimethyl-4-butyl-piperazinium dichloride, 1-octyl-1,4-dimethyl-4-butyl-piperazinium dichloride, 1,4-dibutyl-1-ethyl-4-methyl-piperazinium dichloride, 1,1,4-tributyl-4-methyl-piperazinium dichloride, 1-hexyl-1,4-dibutyl-4- Methyl-piperazinium dichloride, and 1-octyl-1,4-dibutyl-4-methyl-piperazinium dichloride, 1,1-dimethyl-4,4-dibutyl-piperazinium dichloride, 1-ethyl-1-methyl-4,4-dibutyl-piperazinium dichloride, 1,4,4-tributyl-1-methyl-piperazinium dichloride, 1-hexyl-1-methyl-4,4-dibutyl-piperazinium dichloride The following are examples of the dichlorides: 1-octyl-1-methyl-4,4-dibutyl-piperazinium dichloride, 1,4,4-tributyl-1-ethyl-piperazinium dichloride, 1,1,4,4-tetrabutyl-piperazinium dichloride, 1-hexyl-1,4,4-tributyl-piperazinium dichloride, and 1-octyl-1,4,4-tributyl-piperazinium dichloride.

[0165] In a further preferred embodiment according to the present invention, the ionic liquid is selected from 1-substituted imidazolium salts and 1-substituted pyridinium salts, preferably selected from 1,3-substituted, 1,2,3-substituted, 1,2,3,4-substituted and 1,2,3,4,5-substituted imidazolium salts, more preferably selected from 1-alkyl-substituted, 1-alkyl-3-substituted, 1-alkyl-2,3-substituted, 1-alkyl-2,3,4-substituted and 1-alkyl-2,3,4,5-substituted imidazolium salts, even more preferably Preferably, the counterion is selected from 1,3-alkyl-substituted imidazolium salts, especially those having a C1-C12 alkyl substituent at the 1-position and a methyl group at the 3-position, even more preferably 1-methyl-, 1-ethyl-, 1-propyl-, 1-butyl-, 1-pentyl-, 1-hexyl-, 1-octyl-, 1-decyl-, and 1-dodecyl-3-methylimidazolium salts, and most preferably ethyl-MIMCl and hexyl-MIMCl. Preferably, the counterion of the imidazolium- or pyridinium-based ionic liquid is selected from chloride, bromide, acetate, trifluoroacetate, tetrafluoroborate, hexafluorophosphate, or methylsulfonate anion, most preferably chloride, bromide, and tetrafluoroborate.

[0166] According to an embodiment, the 1-substituted pyridinium salt is preferably a compound of the following general formula: [ka] R in the formula 3 are independently selected from methyl, ethyl, butyl, hexyl, and octyl residues, preferably R 3 is a methyl or butyl residue, and Z is preferably a chloride, bromide, acetate, trifluoroacetate, tetrafluoroborate, hexafluorophosphate, or methylsulfonate anion, most preferably Z is a chloride anion.

[0167] Optionally, the N,N-substituted pyridinium salts can carry one or more additional C1-C12 alkyl substituents on one or more of the ring carbon atoms, preferably they also carry one additional methyl, ethyl, butyl, hexyl, and octyl residue, more preferably a methyl, ethyl, or butyl residue on the 2-C, 3-C, or 4-C atom of the ring.

[0168] Specifically preferred N-substituted pyridinium compounds are 1-methyl-pyridinium chloride, 1-ethyl-pyridinium chloride, 1-butyl-pyridinium chloride, 1-hexyl-pyridinium chloride, and 1-octyl-pyridinium chloride.

[0169] Particularly preferred N-substituted pyridinium compounds carrying a further substituent on the 2-C atom of the ring are 1,2-dimethyl-pyridinium chloride, 1-ethyl-2-methyl-pyridinium chloride, 1-butyl-2-methyl-pyridinium chloride, 1-hexyl-2-methyl-pyridinium chloride, 1-octyl-2-methyl-pyridinium chloride, 1-butyl-2-butyl-pyridinium chloride, 1-hexyl-2-butyl-pyridinium chloride and 1-octyl-2-butyl-pyridinium chloride, and preferred N-substituted pyridinium compounds carrying a further substituent on the 3-C atom of the ring are 1,3-dimethyl-pyridinium chloride, 1-ethyl-3-methyl-pyridinium chloride, 1-butyl-3-methyl-pyridinium chloride, 1-hexyl-3-methyl-pyridinium chloride. Preferred N-substituted pyridinium compounds carrying a further substituent on the 4-C atom of the ring are 1,4-dimethyl-pyridinium chloride, 1-ethyl-4-methyl-pyridinium chloride, 1-butyl-4-methyl-pyridinium chloride, 1-hexyl-4-methyl-pyridinium chloride, 1-octyl-4-methyl-pyridinium chloride, 1-butyl-4-butyl-pyridinium chloride, 1-hexyl-4-butyl-pyridinium chloride, and 1-octyl-4-butyl-pyridinium chloride.

[0170] According to a further embodiment, the 1,3-substituted imidazolium salt is preferably a compound of the general formula: [ka] R in the formula 1 and R 2 are independently selected from methyl, ethyl, butyl, hexyl, and octyl residues, preferably R 1 is a methyl or butyl residue, and R 2is selected from methyl, ethyl, butyl, hexyl, and octyl residues, more preferably R 1 is a methyl or butyl residue, and R 2 is selected from a methyl, ethyl or butyl residue, most preferably R 1 and R 2are independently selected from methyl and butyl residues, and Z is preferably selected from chloride, bromide, acetate, trifluoroacetate, tetrafluoroborate, hexafluorophosphate or methylsulfonate anions, most preferably Z is a chloride anion. Optionally, the 1,3-substituted imidazolium salts can carry one or more further C1-C12 alkyl substituents on one or more of the ring carbon atoms, preferably they further carry one methyl, ethyl, butyl, hexyl, and octyl residue, more preferably a methyl, ethyl or butyl residue on the 2-C atom of the ring or the 4-C atom of the ring. Particularly preferred 1,3-substituted imidazolium compounds are 1,3-dimethylimidazolium chloride, 1-ethyl-3-methyl-imidazolium chloride, 1-butyl-3-methyl-imidazolium chloride, 1-hexyl-3-methyl-imidazolium chloride, 1-octyl-3-methyl-imidazolium chloride, 1-butyl-3-ethyl-imidazolium chloride, 1,3-dibutyl-imidazolium chloride, 1-hexyl-3-butyl-imidazolium chloride, and 1-octyl-3-butyl-imidazolium chloride. Particularly preferred 1,3-substituted imidazolium compounds carrying a further substituent on the 2-C carbon atom of the ring are 1,2,3-trimethylimidazolium chloride, 1-ethyl-2,3-dimethyl-imidazolium chloride, 1-butyl-2,3-dimethyl-imidazolium chloride, 1-butyl-2-methyl-3-ethyl-imidazolium chloride, 1,3-dibutyl-2-methyl-imidazolium chloride, 1,3-dimethyl-2-butyl-imidazolium chloride, 1-ethyl-2-butyl-3-methyl-imidazolium chloride, 1,2-dibutyl-3-methyl-imidazolium chloride, 1,2-dibutyl-3-ethyl-imidazolium chloride and 1,2,3-tributyl-imidazolium chloride.Particularly preferred 1,3-substituted imidazolium compounds carrying further substituents on the 4-C carbon atom of the ring are 1,3,4-trimethylimidazolium chloride, 1-ethyl-3,4-dimethyl-imidazolium chloride, 1-butyl-3,4-dimethyl-imidazolium chloride, 1-butyl-3-ethyl-4-methyl-imidazolium chloride, 1,3-dibutyl-4-methyl-imidazolium chloride, 1,3-dimethyl-4-butyl-imidazolium chloride, 1-ethyl-3-methyl-4-butyl-imidazolium chloride, 1,4-dibutyl-3-methyl-imidazolium chloride, 1,4-dibutyl-3-ethyl-imidazolium chloride and 1,3,4-tributyl-imidazolium chloride. The most preferred ionic liquid compounds according to this embodiment are 1-ethyl-3-methylimidazolium chloride (ethyl MIMCl) and 1-hexyl-3-methylimidazolium chloride (hexyl MIMCl).

[0171] In embodiments according to the present invention, the ionic liquid has a melting point of less than about 150°C, preferably less than about 100°C, more preferably less than about 80°C, even more preferably less than about 60°C, even more preferably less than about 40°C, and most preferably less than about 30°C.

[0172] Heterocyclic ionic liquids are defined as those that are liquid at the temperature at which the process is carried out, and since processes according to embodiments of the present invention are preferably carried out at temperatures below about 150°C, heterocyclic liquids according to this embodiment have melting points below about 150°C, which is preferred according to embodiments of the present invention.

[0173] In embodiments according to the present invention, the amount of the one or more ionic liquids is in the range of from about 0.1 mol % to about 1500 mol %, preferably from about 0.2 mol % to about 1000 mol %, more preferably from about 0.4 mol % to about 600 mol %, even more preferably from about 0.7 mol % to about 300 mol %, even more preferably from about 0.7 mol % to about 100 mol %, even more preferably from about 2 mol % to about 100 mol %, and most preferably from about 5 mol % to about 100 mol %, relative to the one or more compounds (B) present in the reaction mixture.

[0174] Preferably, the starting materials for the reaction do not include further components in addition to one or more silane compounds (B), one or more metal hydrides (C), and one or more heterocyclic ionic liquids in amounts relative to the one or more compounds (B) as described above.

[0175] In an embodiment according to the invention, the process is carried out in the absence of ether solvents, preferably in the absence of ether solvents and linear or cyclic aliphatic hydrocarbon solvents, more preferably in the absence of ether solvents and linear or cyclic aliphatic hydrocarbon solvents and aromatic hydrocarbon solvents, and most preferably in the absence of any other solvents other than one or more ionic liquids.

[0176] The use of a solvent in a chemical process may be for a variety of reasons, such as providing a reaction mixture in which the starting materials are uniformly dissolved, controlling the conversion rate and the heat effects associated with exothermic reactions, and many additional purposes known to those skilled in the art. However, there may also be numerous disadvantages associated with the need to use a solvent, such as the toxic nature of many organic solvents, the cost of supplying the solvent, and the problem of removing the solvent from the desired product. In the case of ethereal solvents, there is an additional risk of peroxide formation, which can make the use of such solvents harmful, especially on an industrial scale. Therefore, to avoid the need for additional solvents and the problems discussed above, the process according to this embodiment is carried out without an ethereal solvent, and most preferably without any other solvents other than one or more heterocyclic ionic liquids. While the processes according to other embodiments of the present invention do not generally exclude the presence of any solvent in the reaction mixture, it is generally preferred according to embodiments of the present invention that no solvent is present in addition to the heterocyclic ionic liquids required by the process.

[0177] In an embodiment according to the invention, the process is carried out in the absence of acyclic quaternary ammonium salts and acyclic quaternary phosphonium salts.

[0178] Acyclic quaternary ammonium salts and acyclic quaternary phosphonium salts are known in the art as catalysts for the redispersion reaction of silanes and have been used in the presence of organic solvents, particularly ethereal organic solvents. In the process of the present invention, the presence of a heterocyclic ionic liquid not only allows the use of otherwise too unreactive metal hydrides for the reduction of halosilanes, but also obviates the need for additional redispersion catalysts and solvents, thus reducing process complexity and improving process performance and efficiency.

[0179] In an embodiment according to the invention, the reaction is carried out in the range of about 0 to about 150° C., preferably about 10 to about 150° C., more preferably about 20 to about 150° C., even more preferably about 20 to about 125° C., and most preferably about 50 to about 125° C. As defined herein, the temperature at which the reaction is carried out is the temperature of the reaction mixture, i.e., the temperature measured inside the reaction vessel in which the reaction is carried out.

[0180] In embodiments according to the present invention, the reaction is carried out at a pressure ranging from about 0.1 to about 20 bar, preferably from about 0.3 to about 20 bar, more preferably from about 1 to about 20 bar, even more preferably from about 1 to about 10 bar, and most preferably from about 1 to about 5 bar. As defined herein, the pressure ranges indicated refer to the pressure measured inside the reaction vessel used in carrying out the process of embodiments of the present invention.

[0181] In an embodiment according to the invention, the process is carried out under inert conditions. As defined herein, the term "under inert conditions" means partially or completely carried out under conditions that exclude ambient air, particularly moisture and oxygen. To exclude ambient air from the reaction mixture and reaction products, a closed reaction vessel, reduced pressure, and / or an inert gas, particularly nitrogen or argon, or a combination of these means may be used.

[0182] In embodiments according to the invention, the process can be carried out continuously or discontinuously, such as batchwise. Preferably, the process of the embodiments is carried out batchwise, for example in a batch reactor made of steel, stainless steel, glass-lined steel, glass, or another suitable alloy other than steel.

[0183] In an embodiment according to the invention, the process is carried out without milling or sonication of the reaction mixture.

[0184] The reduction of halosilanes with metal hydrides often requires activation of the metal hydride, which is usually accomplished by adding an activating agent, such as aluminum chloride (AlCl), a solvent that promotes such reactions, such as an ether compound, mechanical activation of the metal hydride, or a combination of these means. Milling and sonication have been found to be particularly effective means of mechanical activation. As used herein, "milling" generally refers to any process aimed at reducing the size of a solid material by mechanical force, and specifically includes performing the reaction in a ball mill.

[0185] The term "sonication," as defined herein, applies to any process in which sound energy, particularly at ultrasonic frequencies, is applied to a reaction mixture, i.e., ultrasonication. When ultrasonic waves are applied to a medium, the sound waves are converted into mechanical energy. Both milling and sonication promote the reaction of metal hydrides with halosilanes by mechanically removing the metal halides that form a passivation layer on the surfaces of the metal hydride particles subjected to reaction with the halosilane, thereby allowing the reaction to continue. Sonication, and particularly milling, further promotes the reaction of metal hydrides with halosilanes by breaking down the metal hydrides into smaller particles, thereby increasing the total surface area of ​​the metal hydride particles. However, both milling and sonication require non-standard equipment, thus increasing the complexity of the reaction. The presence of heterocyclic ionic liquids makes it possible to obtain the desired reduction product when reacting halosilanes, particularly organochloromonosilanes, with metal hydrides, preferably alkali metal hydrides and alkaline earth metal hydrides, especially CaH, without further chemical or mechanical activation, particularly in the absence of milling and sonication. This allows for reduced costs and labor in carrying out the reaction. The process of this embodiment of the present invention is thus carried out without milling or sonication of the reaction mixture, which is generally preferred for processes according to this embodiment of the present invention.

[0186] In an embodiment according to the invention, the process is carried out without feeding hydrogen chloride and / or in the absence of a metal catalyst, preferably in the absence of an aluminum chloride or palladium catalyst.

[0187] The presence of hydrogen chloride or a metal catalyst, particularly AlCl or a palladium catalyst, is not required for the successful implementation of processes according to embodiments of the present invention. AlCl is used in conventional processes to enable the reduction of MeSiCl with MgH. However, under the conditions of processes according to embodiments of the present invention, such activation is not necessary. The presence of AlCl also induces undesirable redispersion of organyl groups of silane compounds (A) and (B) present in the reaction mixture.

[0188] The presence of AlCl3 also poses technical problems, since its high solubility in chlorosilanes and its low sublimation temperature make it difficult to separate it from the products formed. Thus, in this embodiment, the process is carried out without the supply of hydrogen chloride and / or in the absence of metal catalysts, in particular palladium catalysts or AlCl3, which are generally preferred according to the present invention and all its embodiments.

[0189] In an embodiment according to the invention, the silane compound (A) having at least one Si-H bond formed, preferably Me2SiHCl, is separated from the reaction mixture by distillation and / or condensation.

[0190] The term "distillation," as defined herein, refers to any process for separating a compound or substance from an at least partially liquid mixture by selective evaporation and condensation. The distillation may result in a substantially complete separation of the components of the mixture, thus leading to the separation of a nearly pure compound, or in a partial separation, whereby the concentration of a selected component of the mixture in the distillate is increased compared to the mixture subjected to distillation. Preferably, this distillation process, which may constitute a separation step for separating or enriching the desired silane compound (A) having at least one Si-H bond, is selected from simple distillation, fractional distillation, vacuum distillation, short-path distillation, or any other distillation method known to those skilled in the art. Also preferably, the step for separating the desired silane compound (A) having at least one Si-H bond according to embodiments of the present invention may include one or more batch distillation steps or may include a continuous distillation step. More preferably, the term "condensation" may include separation or enrichment of one or more silane compounds (A) having at least one Si-H bond from the reaction mixture by evaporation from the reaction vessel, and may also include condensation as a liquid and / or solid in a cooled vessel, from which the condensate can later be recovered by distillation or as a solution in a solvent.

[0191] In an embodiment of the invention, the starting material subjected to the process contains about 75% by weight or more of one or more compounds (B), preferably about 85% by weight or more of one or more compounds (B), more preferably about 90% by weight or more of one or more compounds (B), and most preferably about 95% by weight or more of one or more compounds (B).

[0192] The term "starting material" refers to all compounds other than the metal hydride (C) and heterocyclic ionic liquid that are subjected to the reaction of the process according to the invention, unless further specified, e.g., as "silane starting material (B)." The amount of one or more compounds (B) given in weight percent thus refers to the ratio of compounds falling within the definition of silane compound (B) to the total amount of compounds falling within (B), excluding the metal hydride (C) and heterocyclic ionic liquid, plus additional additives, solvents, and impurities. Thus, according to an embodiment, the amount of additional additives, e.g., solvents and impurities, is less than about 25 weight percent, preferably less than about 15 weight percent, more preferably less than about 10 weight percent, and most preferably less than about 5 weight percent.

[0193] In an embodiment according to the invention, the starting material subjected to the process contains 75 wt. % or more of organomonochlorosilane (B), preferably about 85 wt. % or more of organomonochlorosilane (B), more preferably about 90 wt. % or more of organomonochlorosilane (B), even more preferably about 95 wt. % or more of organomonochlorosilane (B), and most preferably about 95 wt. % or more of organomonochlorosilane (B), and most preferably about 95 wt. % or more of MeSiCl.

[0194] The amounts given in weight percent relate to the mass of organomonochlorosilane (B) relative to the total amount of silane starting material (B) having one or more Si-X bonds that is reacted, excluding one or more metal hydrides (C) and heterocyclic ionic liquid.

[0195] A solvent other than the ionic liquid, i.e., an organic compound that is inert under the reaction conditions and liquid at the reaction temperature, may generally be present but is not considered necessary. Furthermore, the starting material may contain impurities derived from previously produced organomonochlorosilanes. While the presence of such impurities and solvents is not necessarily detrimental to the performance of the process, in view of reaction control, the need to add excess metal hydride to compensate for hydride consumption in undesired reactions with impurities, and ease of purification of the desired product, it is considered preferable to have as high an amount of organochloromonosilane (B) in the starting material as possible.

[0196] In an embodiment according to the present invention, compound (A) is Me2SiHCl, compound (B) is Me2SiCl2, and the metal hydride is CaH2.

[0197] In this embodiment of the present invention, heterocyclic ionic liquids are particularly important as redispersion catalysts to shift the ratio of the reduction products MeSiHCl and MeSiH to the target product MSiHCl. The starting material MeSiCl may be provided to the process as a substantially pure compound or as a mixture of compounds. For example, the compound may be provided to the process according to embodiments in the form of a crude product obtained from the Direct Process or as a fraction obtained from the purification of MeSiCl produced by the Direct Process, such as so-called Direct Process Residue (DPR), which contains high-boiling by-products such as methylchlorodisilanes and methylchlorooligosilanes. Preferably, the molar ratio of CaH to MeSiCl is in the range of about 0.1 to about 1.1, preferably about 0.2 to about 0.9, more preferably about 0.25 to about 0.7, and even more preferably about 0.3 to about 0.65, provided that the resulting mixture does not contain substantial amounts of other compounds that consume hydride ions in addition to MeSiCl. As defined herein, a substantial amount of such other compounds is any amount greater than about 2% by weight based on the mass of the starting material containing Me2SiCl2.

[0198] In an embodiment according to the present invention, compound (A) is MeSiH2Cl or MeSiHCl2, compound (B) is MeSiCl3, and the metal hydride is CaH2.

[0199] Starting with MeSiCl or a mixture of compounds containing it, both MeSiH2Cl and MeSiHCl2 compounds can be obtained, where the ratio of mono- to di-hydrogenated products can be adjusted by the amount of CaH2 added to the reaction mixture. The use of CaH2 as the hydride source makes the process according to this embodiment particularly cost-effective. In this embodiment of the invention, the heterocyclic ionic liquid is particularly important as a redispersion catalyst to obtain the desired ratio of the reduction products MeSiH2Cl and MeSiHCl2. This function of the ionic liquid is particularly important because the partially hydrogenated species MeSiHCl2 and MeSiH2Cl present in the reaction mixture of the process are more susceptible to further hydrogenation by hydride ions than the starting material MeSiCl3, and thus, without redispersion, an undesirable product distribution dominated by MeSiH3 would be obtained. So long as the starting materials do not contain substantial amounts of other compounds besides MeSiCl that consume hydride ions, the molar ratio of CaH to MeSiCl is preferably in the range of about 0.1 to about 2.0, preferably about 0.2 to about 1.5, more preferably about 0.25 to about 1.0, and even more preferably about 0.3 to about 0.8. When the primary desired product of the process of embodiments is MeSiHCl, the molar ratio of CaH to MeSiCl is preferably in the range of about 0.1 to about 1.1, preferably about 0.2 to about 0.9, more preferably about 0.25 to about 0.7, and even more preferably about 0.3 to about 0.65; when the primary desired product of the process is MeSiHCl, the molar ratio of CaH to MeSiCl is preferably in the range of about 0.3 to about 2.0, preferably about 0.5 to about 1.5, more preferably about 0.6 to about 1.3, and even more preferably about 0.8 to about 1.2.

[0200] In an embodiment according to the invention, the process comprises cleavage of one or more Si-Si bonds of one or more di- or polysilane compounds (B) and / or one or more Si-C bonds of one or more carbodisilane compounds (B).

[0201] By cleavage of one or more Si-Si bonds, it is possible to obtain monosilanes from starting materials (B) such as disilanes, polysilanes, or carbodisilanes. In particular, it is possible to obtain organohalomonosilanes starting from organohalodisilanes and organohalopolysilanes. In the process according to an embodiment of the present invention, cleavage of one or more Si-Si bonds makes it possible to obtain monosilane compounds (A) from starting materials (B) such as disilanes and polysilanes, in particular to obtain organomonosilanes from organodisilanes and organopolysilanes, and preferably to obtain organochloromonosilanes from organochlorodisilanes and organochloropolysilanes. During the process of this embodiment, which involves the cleavage of disilanes and / or polysilanes, the conversion of one or more Si-X moieties of compound (B) to Si-H moieties may occur before, during, or after the cleavage of one or more Si-Si bonds, and the cleavage may occur by reduction with one or more metal hydrides (C) or by redispersion with a monosilane or di-, poly-, or carbodisilane having at least one Si-H bond. The same applies in full analogy to the cleavage of one or more Si-C bonds in carbodisilanes. Thus, the process according to this embodiment starts from chlorodisilanes, chlorohydridodisilanes, chloropolysilanes and chlorohydridopolysilanes to give chlorohydridomonosilanes, in particular from organochlorodisilanes, organochlorohydridodisilanes, organochloropolysilanes and organochlorohydridopolysilanes to give organohydridomonosilanes, preferably according to the embodiment starting from organochlorodisilanes and / or organochloropolysilanes to give organochlorohydridomonosilanes, more preferably starting from methylchlorodisilanes and / or methylchloropolysilanes, i.e. disilanes and / or polysilanes exclusively bearing chloro and methyl substituents to give one or more monosilanes (A) selected from MeSiHCl, MeSiHCl and MeSiHCl.The cleavage of the Si-Si bond of the di-, oligo-, or polysilane, or the cleavage of the Si-C bond of the carbodisilane, is thus preferably carried out simultaneously with the reduction and redispersion reactions accompanying the conversion of the silane compound having at least one Si-Cl bond (B) into the compound having at least one Si-H bond (A), e.g., in the same reaction step and / or in the same reaction vessel.

[0202] According to an embodiment of the present invention, it is preferred that the heterocyclic ionic liquid used in the process simultaneously acts as a solvent, a reaction promoter, a redispersion catalyst, and a cleavage catalyst. Group-15 quaternary onium compounds R4QX, where each R is independently hydrogen or an organyl group, Q is nitrogen, phosphorus, arsenic, antimony, or bismuth, and X is a halide selected from the group consisting of F, Cl, Br, and I; heterocyclic amines, heterocyclic ammonium halides, - a mixture of R3P and Rx, where R is as defined above and X is as defined above; alkali metal halides, alkaline earth metal halides, alkali metal hydrides or alkaline earth metal hydrides, optionally In the presence of hydrogen chloride (HCl), may be used in the process of the above-described embodiments, it is preferred that such additional cleavage catalysts are not present in the reaction mixture as it would make the process less cost-effective and more complex with respect to by-product formation and purification of the desired product.

[0203] In an embodiment according to the present invention, compound (A) is selected from MeSiHCl, MeSiHCl and MeSiHCl, and compound (B) is selected from methylchlorodisilanes and methylchloropolysilanes, preferably methylchlorodisilanes, and wherein the metal hydride is preferably CaH or MgH.

[0204] As defined herein, the term "methylchlorodisilane" includes the compounds MeSiCl, MeSiCl, MeSiCl, MeSiCl, and MeSiCl, where the formula MeSiCl represents the structure MeClSi-SiCl, the formula MeSiCl represents the structures MeClSi-SiCl and MeClSi-SiClMe, the formula MeSiCl represents the structures MeSi-SiCl and MeClSi-SiClMe, the formula MeSiCl represents the structures MeClSi-SiMe and MeClSi-SiClMe, and the formula MeSiCl represents the structure MeClSi-SiMe, where, according to this embodiment, each Si atom preferably carries one or more methyl groups and one or more chloro groups. As defined herein, the term "methylchloropolysilane" includes any type of silane having three or more silicon atoms bonded to one another in a linear chain, wherein the further substituents of the silicon atoms are exclusively selected from methyl and chloro groups. Preferably, according to this embodiment, each Si atom carries one or more methyl groups and one or more chloro groups. As generally described in the above embodiment, the process involving the cleavage of Si-Si bonds allows the production of the desired monosilane compounds (A) MeSiHCl, MeSiHClCl, and MeSiHCl starting from compounds (B) that are methylchlorodisilanes and methylchloropolysilanes. These starting compounds are produced in large quantities as by-products of the direct process for the production of methylchlorosilanes. Furthermore, with regard to this embodiment, the product mixture of the direct process may be directly subjected to the process of this embodiment without prior separation of the main product, dimethyldichlorosilane, from the di-, oligo-, and polysilane by-products, usually referred to as high-boiling residues due to their boiling point characteristics in the separation process.Both the main product MeSiCl, as well as the by-products MeSiCl, methylchlorodisilane, and methylchlorodisilane contained in the product mixture of the Direct Process can be converted to the target compound (A) selected from MeSiHCl, MeSiHCl, and MeSiHCl by cleavage of the Si-Si bond. From an economical point of view, it is preferable to use low-cost reducing agents, such as MgH or CaH, and even more preferably CaH, in the process according to this embodiment.

[0205] In a particularly preferred embodiment of the present invention, Me2SiHCl, MeSiH2Cl and MeSiHCl 2-Compound (A) selected from the group consisting of is obtained by reacting methyldichlorosilane, constituting compound (B), and preferably selected from MeSiCl, MeSiCl and MeSiCl, with CaH in the presence of a heterocyclic ionic liquid, the heterocyclic ionic liquid being preferably an N-heterocyclic ionic liquid, even more preferably from the group of 1-substituted imidazolium salts, even more preferably 1,3-alkyl-substituted imidazolium salts, in particular those having a C-C alkyl substituent in the 1-position and a methyl group in the 3-position, most preferably 1-methyl-, 1-ethyl-, 1-propyl-, 1-butyl-, 1-pentyl-, 1-hexyl-, 1-octyl- and 1-decyl- and 1-dodecyl-3-methylimidazolium salts. Preferably, the counteranion in the imidazolium-based ionic liquid is selected from chloride, bromide, acetate, trifluoroacetate, tetrafluoroborate, hexafluorophosphate, or methyl sulfate anions, and most preferably selected from chloride, bromide, and tetrafluoroborate. Even more preferably, no additional cleavage agent, redispersion catalyst, or activator is added to the reaction mixture. Methylchlorodisilanes (B) may be provided to the reaction of the process according to this embodiment as a substantially pure single compound, or as a mixture of several methylchlorodisilanes (B), or as a mixture of one or more methylchlorodisilanes with additional silane compounds, such as high-boiling residues obtained when carrying out the Direct Process for producing methylchlorosilanes, and / or additional compounds not falling within the definition of compound (B). It is believed useful for materials subjected to processes containing one or more compounds (B) to contain about 5% or more methylchlorodisilane by weight of the process, more preferably about 20% or more, even more preferably about 50% or more, and even more preferably about 75% or more, and most preferably about 95% or more methylchlorodisilane by weight.

[0206] According to the present invention, a compound having less than about 2% by weight of impurities, based on the total weight of the compound and the impurities contained therein, is considered to be substantially pure. Preferably, as described with respect to the above embodiment, the presence of one or more heterocyclic liquids enables the cleavage of Si-Si bonds necessary to convert compound (B) selected from methylchlorodisilanes or methylchloropolysilanes to methylmonosilanes in the absence of an additional cleavage catalyst.

[0207] In a further embodiment, the present invention provides a method for producing a pharmaceutical composition comprising: one or more silane compounds (A') having at least one Si-H bond and at least one Si-X bond, where X is a halogen atom, one or more metal halides (C'), one or more heterocyclic ionic liquids, - a composition comprising one or more silane compounds (A'') optionally having at least two Si-H bonds and no Si-X bonds. Preferably, the compounds (A'') are silane compounds obtained from the corresponding silane compounds (A') by substituting any Si-X bond by a Si-H bond.

[0208] Such compositions can be obtained by the process of the present invention detailed above.

[0209] Silane compound (A') The term "one or more compounds having at least one Si-H bond and at least one Si-X bond (A')" is defined herein to include any compound containing at least one Si-H bond and at least one Si-X bond (B), where X is a halogen, i.e., a fluoro, chloro, bromo or iodo group, preferably a chloro group, and mixtures of two or more of such compounds present in the composition.

[0210] Thus, the silane compound (A') may be selected from monosilanes, disilanes, oligo- or polysilanes and carbodisilanes having at least one Si-H bond and at least one Si-X bond, where in the compositions according to the invention, monosilanes, di-, oligo- and polysilanes are preferred compounds (A'), mono- and disilanes are more preferred compounds (A'), and monosilanes are generally the most preferred compounds (A').

[0211] The silane compound (A') constituting the composition can be a silane compound with substituents exclusively selected from halogen atoms and hydrogen atoms, but preferably the composition is an organosilane, i.e., a compound (A') further having at least one Si-R bond, where R is an organyl group.

[0212] According to an embodiment of the present invention, the organyl group R comprises an optionally substituted, but preferably unsubstituted, group independently selected from the group consisting of alkyl, aryl, alkenyl, alkynyl, alkaryl, aralkyl, aralkenyl, aralkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, cycloaralkyl, cycloaralkenyl, and cycloaralkynyl groups, even more preferably selected from alkyl, cycloalkyl, alkenyl, and aryl groups, even more preferably selected from methyl, ethyl, vinyl, and phenyl, and most preferably R is a methyl group.

[0213] Metal Halides (C') Metal halides (C') are compounds containing one or more metals and one or more halides, preferably they are ionic compounds containing one or more metal cations and one or more halide anions.

[0214] In an embodiment of the present invention, the metal halide (C') is selected from divalent metal halides, preferably selected from alkali metal halides and alkaline earth metal halides, more preferably selected from alkali metal chlorides and alkaline earth metal chlorides, even more preferably selected from the group of lithium chloride, sodium chloride, potassium chloride, magnesium chloride, and calcium chloride, even more preferably selected from magnesium chloride, sodium chloride, or calcium chloride, and most preferably the metal halide is calcium chloride.

[0215] The metal halide (C') is formed in the process of the present invention as described above by exchanging the hydride and halide substituents of the metal hydride and halosilane.

[0216] Heterocyclic ionic liquids As already explained above, heterocyclic ionic liquids are salts containing heterocyclic anions and / or cations that are liquid under the conditions of the process according to the invention. Typically, the salts or ionic liquids have a melting point below about 150°C, preferably below about 140°C, more preferably below about 120°C, even more preferably below about 100°C, and most preferably below about 50°C.

[0217] According to embodiments of the present invention, the heterocyclic structure of the ionic liquid is not limited in any way, except that a cyclic structure containing one or more heteroatoms must be present in the ionic liquid, i.e., must contain at least one atom other than carbon and hydrogen atoms as a ring member, and the cyclic structure may be aromatic or non-aromatic.

[0218] Cyclic structures consisting exclusively of carbon atoms bearing one or more heteroatom substituents are not considered heterocycles according to the present invention. The heteroatoms are typically selected from oxygen (O), sulfur (S), phosphorus (P), and nitrogen (N) atoms, with P- and N-heterocycles being generally preferred.

[0219] Although there are no restrictions on the ring size of the heterocyclic structure, the number of heteroatoms present in the heterocyclic ring, or the type of heteroatom, it is preferred that the heterocyclic structure is a 5- or 6-membered ring containing one or two heteroatoms, where the heteroatoms are preferably selected from N and P atoms. These structures can be either aromatic or non-aromatic.

[0220] For the compositions of the present invention, the same heterocyclic ionic liquids are used and are preferred as described above for the process of the present invention.

[0221] In an embodiment according to the present invention, each of X in the silane compound (A') is a chlorine atom, and the metal halide (C') is a metal chloride.

[0222] In a further embodiment according to the present invention, the silane compound (A') is a monosilane, preferably an organohydridochloromonosilane.

[0223] According to this embodiment of the invention, the silane compound (A') is an organohydridohalosilane having the formula RSiXH, RSiXH, and RSiXH, wherein the organyl substituents R are preferably independently selected from a C-C alkyl group or a phenyl group, more preferably selected from a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a cyclopentyl group, a cyclohexyl group, or a phenyl group, and most preferably selected from a methyl group and a phenyl group.

[0224] According to an embodiment, X are simultaneously independently selected from F, Cl, Br or I substituents, preferably all X represent Cl atoms.

[0225] The most preferred silane compounds (A') according to the embodiment are MeSiH2Cl, MeSiHCl2 and Me2SiHCl.

[0226] In a more specific embodiment according to the present invention, the silane compound (A') is selected from monosilanes of the general formula: R x SiH y Cl z (I') In the formula, R is an organyl group, x=0 to 2, preferably 1 or 2; y=1-3, preferably 1 or 2; z=1-3, preferably 1 or 2, and x+y+z=4.

[0227] This monosilane (A') according to an embodiment can be a chlorosilane that does not carry any organyl group R, i.e., x = 0 in general formula (I). Preferred halomonosilanes according to an embodiment are HSiCl, HSiBr, and HSiI, with SiCl and HSiCl being most preferred. More preferably, the monosilane (A') is an organomonosilane, where x is 1 or 2, and y is preferably 1 or 2.

[0228] Preferably, the silane compound (A') is selected from organomonosilanes of the general formula: R x SiH y Cl z (I') In the formula, R is an organyl group, x=1 to 2, y=1 or 2, z=1 or 2, and x+y+z=4.

[0229] Preferred organomonosilanes according to the present invention are R2SiHCl, RSiH2Cl, and RSiHCl2. More preferably, the organyl group R is selected from methyl, ethyl, phenyl, and vinyl. The most preferred monosilane products (A') are Me2SiHCl, MeSiHCl2, and MeSiH2Cl.

[0230] In an embodiment according to the invention, the inventive compositions described herein further comprise one or more monosilane compounds (A″) of the following general formula: R x SiH y (I'') In the formula, R is an organyl group, x=0 to 2, preferably 1 or 2; y=2 to 4, preferably 2 or 3, and x+y=4.

[0231] The monosilane compound having formula (I") is typically formed in the process of the present invention by complete reduction of the chlorosilane. It is preferred that the amount of hydridomonosilane of formula (I") be as small as possible relative to the amount of hydridochloromonosilane of formula (I').

[0232] Preferably, the silane compound (A″) is selected from organomonosilane compounds of the general formula: R x SiH y (I'') During the ceremony x=1 or 2, y=2 or 3, x+y=4.

[0233] Preferred organomonosilanes according to the embodiment of formula (I'') are R2SiH2 and RSiH3. Preferably, the organyl group R is selected from methyl, ethyl, phenyl, and vinyl groups. The most preferred monosilane compounds (I'') are Me2SiH2 and MeSiH3.

[0234] Also preferably, the organyl group or the group R of the organomonosilane compound (A″) of the general formula (I″) R x SiH y (I'') During the ceremony x=1 or 2, y=2 or 3, x+y=4, is the same as that in the organomonosilane compound (A') that constitutes the composition.

[0235] More preferably, the compound (A'') is a silane compound formed by substituting any Si-X bond of the corresponding silane compound (A') with a Si-H bond.

[0236] In an embodiment according to the present invention, the molar ratio of compound (A') to compound (A'') is about 5:1 or greater, preferably about 8:1 or greater, more preferably about 10:1 or greater, and even more preferably about 15:1 or greater.

[0237] In another embodiment according to the invention, one or two organyl groups R of the silane compound (A') are selected from monosilanes of the general formula: R x SiH y Cl z (I') In the formula, R is an organyl group, x=0 to 2, preferably 1 or 2; y=1-3, preferably 1 or 2; z=1-3, preferably 1 or 2, and x+y+z=4, is independently selected from the group consisting of an alkyl group, a cycloalkyl group, or a phenyl group, preferably R is a methyl group, an ethyl group, a vinyl group, or a phenyl group, and most preferably R is a methyl group.

[0238] In yet another embodiment according to the present invention, compound (A') is selected from Me2SiHCl, MeSiH2Cl, and MeSiHCl2, preferably compound (A') is Me2SiHCl.

[0239] In an embodiment according to the present invention, the metal halide (C') is selected from alkali metal chlorides and alkaline earth metal chlorides, preferably the metal halide (C') is selected from LiCl, NaCl, KCl, MgCl2 and CaCl2, and most preferably the metal chloride (C') is CaCl2.

[0240] In another embodiment according to the present invention, the heterocyclic ionic liquid is selected from the group consisting of N-heterocyclic quaternary ammonium ionic liquids and P-heterocyclic phosphonium ionic liquids, preferably the heterocyclic ionic liquid is selected from the group consisting of N-heterocyclic aromatic quaternary ammonium ionic liquids and P-heterocyclic aromatic quaternary phosphonium ionic liquids.

[0241] More preferably, the heterocyclic ionic liquid is selected from the group of aromatic heterocyclic quaternary ammonium salts, including pyridinium salts, imidazolium salts, 1,2,3-triazolium salts, imidazolinium salts, and pyrrolium salts; the group of non-aromatic heterocyclic quaternary ammonium salts, including morpholinium salts, piperidinium salts, piperazinium salts, and pyrrolidinium salts; and the group of aromatic heterocyclic quaternary phosphonium salts, including phosphininium salts, preferably ionic liquids. The alkyl group is selected from 1-substituted imidazolium salts and 1-substituted pyridinium salts, preferably selected from 1,3-substituted, 1,2,3-substituted, 1,2,3,4-substituted and 1,2,3,4,5-substituted imidazolium salts, more preferably selected from 1-alkyl-substituted 1,3-substituted, 1,2,3-substituted, 1,2,3,4-substituted and 1,2,3,4,5-substituted imidazolium salts, and even more preferably selected from ethyl MIMCl and hexyl MIMCl.

[0242] In an embodiment according to the present invention, the silane compound (A') is an organomonosilane compound (A') of the following general formula: R x SiH y Cl z (I') In the formula, R is an organyl group, x=1 to 2, y=1 or 2, z=1 or 2, and x+y+z=4, The metal halide (C') is CaCl2, and the heterocyclic ionic liquid is an N-heterocyclic quaternary ammonium ionic liquid.

[0243] In another embodiment according to the present invention, the molar ratio of the one or more heterocyclic ionic liquid compounds to the one or more silane compounds (A') having at least one Si-H bond and at least one Si-X bond is in the range of from about 0.1 mol % to about 1500 mol %, preferably from about 0.2 mol % to about 1000 mol %, more preferably from about 0.4 mol % to about 600 mol %, even more preferably from about 0.7 mol % to about 300 mol %, even more preferably from about 0.7 mol % to about 100 mol %, even more preferably from about 2 mol % to about 100 mol %, and most preferably from about 5 mol % to about 100 mol %.

[0244] In a further embodiment according to the invention, compound (A') is Me2SiHCl, compound (A'') is Me2SiH2, and the metal halide is CaCl2.

[0245] In yet a further embodiment according to the invention, compound (A') is MeSiH2Cl or MeSiHCl2, compound (A'') is MeSiH3, and the metal halide is CaCl2.

[0246] In a preferred embodiment according to the present invention, the silane compound (A') is Me2SiHCl, Metal halides (C') are CaCl2, Heterocyclic ionic liquids are N-heterocyclic quaternary ammonium ionic liquids, The molar ratio of the N-heterocyclic quaternary ammonium ionic liquid to MeSiHCl ranges from about 0.7 mol % to about 300 mol %, preferably from about 0.7 mol % to about 100 mol %, more preferably from about 2 mol % to about 100 mol %, and most preferably from about 5 mol % to about 100 mol %, and the composition comprises MeSiH, wherein the molar ratio of MeSiHCl to MeSiH is about 5:1 or greater, preferably about 8:1 or greater, more preferably about 10:1 or greater, and even more preferably about 15:1 or greater.

[0247] Any numerical range recited herein is understood to include all subranges within that range, and any combination of the various endpoints of such ranges or subranges, whether or not they are set forth in the examples or elsewhere herein.

[0248] It is also understood herein that any of the components of the present invention described by any particular genus or species detailed in the Examples section herein can, in one embodiment, be used to define an alternative definition for any endpoint of the ranges described elsewhere in this specification for that component, and thus, in one non-limiting embodiment, can replace the endpoints of the ranges described elsewhere.

[0249] Furthermore, all compounds, materials, or substances explicitly or implicitly disclosed and / or claimed herein as belonging to a group of structurally, compositionally, and / or functionally related compounds, materials, or substances are understood to include the individual members of that group and all combinations thereof.

[0250] While the above description contains many specifics, these specifics should not be construed as limitations on the scope of the invention, but merely as exemplifications of preferred embodiments thereof. Those skilled in the art will envision many other possible variations that are within the scope and spirit of the invention as defined by the appended claims.

[0251] Overview of the Preferred Embodiments of the Invention The following provides an overview of preferred embodiments of the present invention: 1. A process for the preparation of one or more silane compounds (A) having at least one Si-H bond, The method comprises the step of reacting one or more compounds (B) having at least one Si-X bond, where X is a halogen atom, with one or more metal hydrides (C) in the presence of one or more heterocyclic ionic liquids.

[0252] 2. The process of embodiment 1, wherein each X is independently selected from a chlorine atom, a bromine atom, or an iodine atom, preferably a chlorine atom, more preferably each X in compound (B) is a chlorine atom.

[0253] 3. The process according to any of the previous embodiments, wherein the compound (A) having at least one Si—H bond is an organomonosilane compound, preferably an organohydridochloromonosilane.

[0254] 4. The process according to any of the previous embodiments, wherein the compound (B) having at least one Si—X bond is an organosilane compound, preferably an organoperchlorosilane, more preferably an organoperchloromonosilane compound.

[0255] 5. The product (A) is selected from monosilanes of the following general formula (I): R x SiH y Cl z (I) In the formula, R is an organyl group, x=0 to 3, preferably 0, 1, 2 and 3; y=1 to 4, preferably 1 to 2, most preferably 1; z=0 to 3, preferably 0, 1, 2 and 3, and 10. The process according to any of the previous embodiments, wherein x+y+z=4.

[0256] 6. The product (A) is selected from monosilanes of the following general formula (I): R x SiH y Cl z (I) In the formula, R is an organyl group, x=1 to 3, preferably 1 to 2, y=1 to 3, preferably 1 to 2, z=0 to 2, preferably 1 to 2, and 10. The process according to any of the previous embodiments, wherein x+y+z=4.

[0257] 7. The compound (B) having at least one Si-X bond is selected from organochloromonosilanes of the following general formula (II): R a SiH b Cl c (II) wherein R is as defined above; a=1 to 3, b=0 to 2, c=1 to 3, and 10. The process according to any of the previous embodiments, wherein a+b+c=4.

[0258] 8. The process according to any of the previous embodiments, wherein R is independently selected from an alkyl group, a cycloalkyl group, or an phenyl group, preferably R is a methyl group.

[0259] 9. The process according to any of the previous embodiments, wherein compound (A) is selected from Me2SiHCl, MeSiH2Cl, MeSiHCl2, HSiCl3, and Me3SiH, preferably compound (A) is Me2SiHCl.

[0260] 10. The process according to any of the previous embodiments, wherein compound (B) is selected from Me2SiCl2, MeSiCl3, SiCl4 and Me3SiCl, preferably compound (B) is Me2SiCl2.

[0261] 11. The process according to any of the previous embodiments, wherein the metal hydride (C) is selected from an alkali metal hydride, an alkaline earth metal hydride, or a complex metal hydride comprising an alkali metal or alkaline earth metal cation, preferably the metal hydride (C) is selected from LiH, NaH, KH, MgH2, CaH2 and LiAlH4, and most preferably the metal hydride (C) is CaH2.

[0262] 12. The process according to any of the previous embodiments, wherein the process is carried out without a metal hydride reagent (C) other than CaH2.

[0263] 13. The process according to any of the previous embodiments, wherein the molar ratio of hydride ions of the one or more metal hydrides to halogen atoms, preferably chlorine atoms, of the one or more compounds (B) in the reaction mixture is in the range of from about 0.01 to about 300, more preferably from about 0.1 to about 10, even more preferably from about 0.4 to about 6, and most preferably from about 0.7 to about 3.

[0264] 14. The process according to any of the previous embodiments, wherein the heterocyclic ionic liquid is selected from the group consisting of N-heterocyclic ionic liquids and P-heterocyclic ionic liquids.

[0265] 15. The process according to any of the previous embodiments, wherein the heterocyclic ionic liquid is selected from the group consisting of N-heterocyclic aromatic ionic liquids and P-heterocyclic aromatic ionic liquids.

[0266] 16. The process according to any of the previous embodiments, wherein the heterocyclic ionic liquid is selected from the group consisting of N-heterocyclic quaternary ammonium ionic liquids and P-heterocyclic phosphonium ionic liquids.

[0267] 17. The process according to any of the previous embodiments, wherein the heterocyclic ionic liquid is selected from the group consisting of N-heterocyclic aromatic quaternary ammonium ionic liquids and P-heterocyclic aromatic quaternary phosphonium ionic liquids.

[0268] 18. The process according to any of the previous embodiments, wherein the heterocyclic ionic liquid is selected from the group of aromatic heterocyclic quaternary ammonium salts, including pyridinium salts, imidazolium salts, 1,2,3-triazolium salts, imidazolinium salts, and pyrrolium salts; the group of non-aromatic heterocyclic quaternary ammonium salts, including morpholinium salts, piperidinium salts, piperazinium salts, and pyrrolidinium salts; and the group of aromatic heterocyclic quaternary phosphonium salts, including phosphininium salts.

[0269] 19. The process according to any of the previous embodiments, wherein the ionic liquid is selected from 1-substituted imidazolium salts and 1-substituted pyridinium salts, preferably 1,3-substituted, 1,2,3-substituted, 1,2,3,4-substituted and 1,2,3,4,5-substituted imidazolium salts, more preferably 1-alkyl-substituted 1,3-substituted, 1,2,3-substituted, 1,2,3,4-substituted and 1,2,3,4,5-substituted imidazolium salts, and even more preferably ethyl-MIMCl and hexyl-MIMCl.

[0270] 20. The process according to any of the previous embodiments, wherein the ionic liquid has a melting point of less than about 150°C, preferably less than about 100°C, more preferably less than about 80°C, even more preferably less than about 60°C, even more preferably less than about 40°C, and most preferably less than about 30°C.

[0271] 21. The process according to any of the previous embodiments, wherein the amount of the one or more ionic liquids relative to the one or more compounds (B) in the reaction mixture is in the range of from about 0.1 mol % to about 1500 mol %, preferably from about 0.2 mol % to about 1000 mol %, more preferably from about 0.4 mol % to about 600 mol %, even more preferably from about 0.7 mol % to about 300 mol %, even more preferably from about 0.7 mol % to about 100 mol %, even more preferably from about 2 mol % to about 100 mol %, and most preferably from about 5 mol % to about 100 mol %.

[0272] 22. The process according to any of the previous embodiments, wherein the process is carried out in the absence of ether solvents, preferably in the absence of ether solvents and linear or cyclic aliphatic hydrocarbon solvents, more preferably in the absence of ether solvents and linear or cyclic aliphatic hydrocarbon solvents and aromatic hydrocarbon solvents, and most preferably in the absence of any solvent other than the one or more ionic liquids.

[0273] 23. A process according to any of the previous embodiments, wherein the process is carried out in the absence of acyclic quaternary ammonium salts and acyclic quaternary phosphonium salts.

[0274] 24. The process according to any of the previous embodiments, wherein the reaction is carried out in the range of about 0 to about 150°C, preferably about 10 to about 150°C, more preferably about 20 to about 150°C, even more preferably about 20 to about 125°C, and most preferably about 50 to about 125°C.

[0275] 25. The process according to any of the previous embodiments, wherein the reaction is carried out at a pressure in the range of from about 0.1 to about 20 bar, preferably from about 0.3 to about 20 bar, more preferably from about 1 to about 20 bar, even more preferably from about 1 to about 10 bar, and most preferably from about 1 to about 5 bar.

[0276] 26. A process according to any of the previous embodiments, wherein the process is carried out under inert conditions.

[0277] 27. A process according to any of the preceding embodiments, wherein the process is carried out continuously or discontinuously, such as batchwise.

[0278] 28. A process according to any of the previous embodiments, wherein the process is carried out in the absence of milling or sonication of the reaction mixture.

[0279] 29. A process according to any of the previous embodiments, wherein the process is carried out without a supply of hydrogen chloride and / or in the absence of a metal catalyst, preferably in the absence of an aluminum chloride or palladium catalyst.

[0280] 30. The process according to any of the previous embodiments, wherein the silane compound (A) having at least one Si—H bond formed, preferably Me2SiHCl, is separated from the reaction mixture by distillation and / or condensation.

[0281] 31. The process according to any of the previous embodiments, wherein the starting material contains about 75% or more by weight of one or more compounds (B), preferably about 85% or more by weight of one or more compounds (B), more preferably about 90% or more by weight of one or more compounds (B), and most preferably about 95% or more by weight of one or more compounds (B).

[0282] 32. The process according to any of the previous embodiments, wherein the starting material contains about 75 wt. % or more organomonochlorosilane (B), preferably about 85 wt. % or more organomonochlorosilane (B), more preferably about 90 wt. % or more organomonochlorosilane (B), even more preferably about 95 wt. % or more organomonochlorosilane (B), and most preferably about 95 wt. % or more Me2SiCl2.

[0283] 33. The process according to any of the previous embodiments, wherein compound (A) is Me2SiHCl, compound (B) is Me2SiCl2, and the metal hydride is CaH2.

[0284] 34. The process according to any of the previous embodiments 1 to 32, wherein compound (A) is MeSiH2Cl or MeSiHCl2, compound (B) is MeSiCl3, and the metal hydride is CaH2.

[0285] 35. The process according to any of the previous embodiments 1 to 32, wherein the process comprises cleavage of one or more Si-Si bonds of the one or more di- or polysilane compounds (B), and / or one or more Si-C bonds of the one or more carbodisilane compounds (B).

[0286] 36. The process according to any of the previous embodiments 1 to 32 and 35, wherein compound (A) is selected from Me2SiHCl, MeSiH2Cl and MeSiHCl2, and compound (B) is selected from methylchlorodisilanes and methylchloropolysilanes, preferably methylchlorodisilanes, and the metal hydride is preferably CaH2 or MgH2.

[0287] 37. A composition comprising: one or more silane compounds (A') having at least one Si-H bond and at least one Si-X bond, where X is a halogen atom, one or more metal halides (C'), one or more heterocyclic ionic liquids, - optionally one or more silane compounds (A'') having at least two Si-H bonds and no Si-X bonds; A composition comprising:

[0288] 38. The composition according to embodiment 37, wherein each X is a chlorine atom and the metal halide (C') is a metal chloride.

[0289] 39. The composition according to embodiments 37 and 38, wherein the silane compound (A') is a monosilane, preferably an organohydridochloromonosilane.

[0290] 40. The silane compound (A') is selected from monosilanes of the general formula: R x SiH y Cl z (I') In the formula, R is an organyl group, x=0 to 2, preferably 1 or 2; y=1-3, preferably 1 or 2; z=1-3, preferably 1 or 2, and The composition according to embodiments 37 to 39, wherein x+y+z=4.

[0291] 41. The silane compound (A') is selected from organomonosilanes of the general formula: R x SiH y Cl z (I') In the formula, R is an organyl group, x=1 to 2, y=1 or 2, z=1 or 2, and The composition according to embodiments 37 to 40, wherein x+y+z=4.

[0292] 42. The composition further comprises one or more monosilane compounds (A″) of the following general formula: R x SiH y (I'') In the formula, R is an organyl group, x=0 to 2, preferably 1 or 2, and y=2 to 4, preferably 2 or 3, and x+y=4, Preferably, the silane compound (A″) is selected from organomonosilane compounds of the general formula: R x SiH y (I'') During the ceremony, x=1 or 2, y=2 or 3, x+y=4, And here preferably, The composition according to embodiments 37 to 41, wherein the organyl group or groups of the organomonosilane compound (A″) are the same as in the organomonosilane compound (A′).

[0293] 43. The composition according to any one of embodiments 37 to 42, wherein compound (A″) is a silane compound formed from the corresponding silane compound (A′) by replacing any Si—X bond with a Si—H bond.

[0294] 44. The composition according to embodiments 37 to 43, wherein one or two organyl groups R of the silane compound (A') are independently selected from the group consisting of an alkyl group, a cycloalkyl group, or a phenyl group, preferably R is a methyl group, an ethyl group, a vinyl group, or a phenyl group, and most preferably R is a methyl group.

[0295] 45. The composition according to embodiments 37 to 44, wherein compound (A') is selected from Me2SiHCl, MeSiH2Cl, and MeSiHCl2, preferably compound (A') is Me2SiHCl.

[0296] 46. ​​The composition according to embodiments 37 to 45, wherein the metal halide (C') is selected from alkali metal chlorides and alkaline earth metal chlorides, preferably the metal halide (C') is selected from LiCl, NaCl, KCl, MgCl2 and CaCl2, and most preferably the metal chloride (C') is CaCl2.

[0297] 47. The composition according to embodiments 37 to 46, wherein the heterocyclic ionic liquid is selected from the group consisting of N-heterocyclic quaternary ammonium ionic liquids and P-heterocyclic phosphonium ionic liquids, preferably the heterocyclic ionic liquid is selected from the group consisting of N-heterocyclic aromatic quaternary ammonium ionic liquids and P-heterocyclic aromatic quaternary phosphonium ionic liquids.

[0298] 48. The silane compound (A') is an organomonosilane compound (A') of the following general formula: R x SiH y Cl z (I') In the formula, R is an organyl group, x=1 to 2, y=1 or 2, z=1 or 2, and x+y+z=4, Metal halides (C') are CaCl2, and The composition according to embodiments 37 to 47, wherein the heterocyclic ionic liquid is an N-heterocyclic quaternary ammonium ionic liquid.

[0299] 49. The heterocyclic ionic liquid is selected from the group of aromatic heterocyclic quaternary ammonium salts, including pyridinium salts, imidazolium salts, 1,2,3-triazolium salts, imidazolinium salts, and pyrrolium salts; from the group of non-aromatic heterocyclic quaternary ammonium salts, including morpholinium salts, piperidinium salts, piperazinium salts, and pyrrolidinium salts; and from the group of aromatic heterocyclic quaternary phosphonium salts, including phosphininium salts; preferably, the ionic liquid is selected from the group of aromatic heterocyclic quaternary ammonium salts, including pyridinium salts, morpholinium salts, piperidinium salts, piperazinium salts, and pyrrolidinium salts; 49. The composition according to embodiments 37 to 48, wherein the alkyl group is selected from 1,3-substituted imidazolium salts and 1-substituted pyridinium salts, preferably from 1,3-substituted, 1,2,3-substituted, 1,2,3,4-substituted and 1,2,3,4,5-substituted imidazolium salts, more preferably from 1-alkyl-substituted 1,3-substituted, 1,2,3-substituted, 1,2,3,4-substituted and 1,2,3,4,5-substituted imidazolium salts, and even more preferably from ethyl MIMCl and hexyl MIMCl.

[0300] 50. The composition according to embodiments 37 to 49, wherein the molar ratio of compound (A') to compound (A'') is 5:1 or greater, preferably 8:1 or greater, more preferably 10:1 or greater, even more preferably 15:1 or greater.

[0301] 51. The composition according to embodiments 37 to 50, wherein the molar ratio of the one or more heterocyclic ionic liquid compounds to the one or more silane compounds (A') having at least one Si-H bond and at least one Si-X bond is from about 0.1 mol % to about 1500 mol %, preferably from about 0.2 mol % to about 1000 mol %, more preferably from about 0.4 mol % to about 600 mol %, even more preferably from about 0.7 mol % to about 300 mol %, even more preferably from about 0.7 mol % to about 100 mol %, even more preferably from about 2 mol % to about 100 mol %, and most preferably from about 5 mol % to about 100 mol %.

[0302] 52. The composition according to any one of embodiments 37 to 51, wherein compound (A′) is Me2SiHCl, compound (A″) is Me2SiH2, and the metal halide is CaCl2.

[0303] 53. The composition according to any one of embodiments 37 to 51, wherein compound (A′) is MeSiH2Cl or MeSiHCl2, compound (A″) is MeSiH3, and the metal halide is CaCl2.

[0304] 54. The silane compound is (A') Me2SiHCl; The metal halide (C') is CaCl2, Heterocyclic ionic liquids are N-heterocyclic quaternary ammonium ionic liquids, the molar ratio of the N-heterocyclic quaternary ammonium ionic liquid to MeSiHCl ranges from about 0.7 mol % to about 300 mol %, preferably from about 0.7 mol % to about 100 mol %, more preferably from about 2 mol % to about 100 mol %, and most preferably from about 5 mol % to about 100 mol %, and 53. A composition according to any one of embodiments 37 to 52, wherein the composition comprises Me2SiH2, wherein the molar ratio of Me2SiHCl to Me2SiH2 is about 5:1 or greater, preferably about 8:1 or greater, more preferably about 10:1 or greater, and even more preferably about 15:1 or greater.

[0305] The present invention will now be described in more detail with reference to examples.

[0306] Example The present invention is further illustrated by the following examples, but is not limited thereto.

[0307] General All reactions were carried out in a 100 ml Hastelloy pressure reactor equipped with a magnetic stirrer, a manometer, a TC Company RTD sensor (platinum resistance temperature sensor) Pt100, and a three-way input / output valve.

[0308] 1-Ethyl-3-methylimidazolium chloride (ethyl MIMCl) (98%) and 1-hexyl-3-methylimidazolium chloride (hexyl MIMCl) (97%) were both purchased from Sigma-Aldrich.

[0309] The products were analyzed and characterized by standard procedures, especially by GC and GC / MS analysis.

[0310] Analysis of the products The products were analyzed by GC-MS (gas chromatography / mass spectrometry).

[0311] The methods applied are listed in the table below.

[0312] [Table 1]

[0313] Under the given GC conditions, the retention times were as follows: Me2SiH2(H2) 0.908 min Me2SiHCl(H1) 0.997 min Me2SiCl2 (precursor) 1.192 min

[0314] Additionally, the identity of the compounds Me2SiH2 and Me2SiHCl was confirmed by MS fragmentation analysis: GC-MS fragments characteristic of H2 and H1 Me2SiH2(H2) M=60 Detected fragments 59 (MH) and 58 (M-2H) Me2SiHCl(H1) M=94.5 Detected fragments 93 (MH) and 79 (M-CH3)

[0315] Example 1 (Comparative Example) Reaction of Me2SiCl2 with LiH and Bu4PCl in THF 0.19 g (0.6 mmol) of Bu4PCl was dissolved in 15 ml of dry THF and placed in a reaction vessel. - ) of LiH was added. The autoclave was closed and cooled to 4 °C. 3 g of Me2SiCl2 was injected via syringe through the three-way valve. The temperature of the reaction mixture immediately rose to 17 °C. An additional 13.2 g of Me2SiCl2 was injected (total of 16.2 g of Me2SiCl2 = 126 mmol), and the reaction vessel was closed and heated at 120 °C for 4 h. After cooling to room temperature, the composition of the liquid phase (containing silane, ether solvent, and some salts) was analyzed by GC (~10% solution in dry toluene; details of the GC method are given in Table 1). The area ratio H1:H2 of the target product Me2SiHCl (H1) to the undesired intermediate product Me2SiH2 (H2) was determined. The results are shown in Table 2.

[0316] Example 2 (Comparative Example) Reaction of Me2SiCl2 with CaH2 and Bu4PCl in THF 0.19 g (0.6 mmol) of Bu4PCl was dissolved in 15 ml of dry THF and placed in a reaction vessel. - ) of CaH2 was added. The autoclave was closed and cooled to 4 °C. 16.2 g (126 mmol) of Me2SiCl2 was injected via syringe through the three-way valve. The temperature of the reaction mixture immediately rose to 13 °C. The reaction vessel was closed and heated at 120 °C for 4 h. After cooling to room temperature, the composition of the liquid phase (containing silane, ether solvent, and some salts) was analyzed by GC (~10% solution in dry toluene; details of the GC method are given in Table 1). The area ratio H1:H2 of the target product Me2SiHCl (H1) to the undesired intermediate product Me2SiH2 (H2) could not be determined because neither Me2SiHCl nor Me2SiH2 was formed in detectable amounts.

[0317] Example 3 Reaction of Me2SiCl2 with CaH2 in 1-ethyl-3-methylimidazolium chloride (ethylMIMCl) 15 g of 1-ethyl-3-methylimidazolium chloride (98%) dissolved in 0.53 g (25.2 mmol) of H - ) of CaH2 and placed in the reaction vessel. 16.2 g of Me2SiCl2 (126 mmol) was injected through the three-way valve, and the reaction vessel was closed and heated at 120 °C for 4 h. The reaction mixture was then cooled to room temperature. The reaction mixture consisted of a solid phase well separated from the liquid phase. The composition of the silane liquid phase was analyzed by GC. Again, the area ratio H1:H2 of the target product Me2SiHCl (H1) to the undesired intermediate product Me2SiH2 (H2) was determined.

[0318] Example 4 Reaction of Me2SiCl2 with CaH2 in 1-hexyl-3-methylimidazolium chloride (HexylMIMCl) 15 g of 1-hexyl-3-methylimidazolium chloride (97%) dissolved in 0.53 g (25.2 mmol) of H - ) of CaH2 and placed in a reaction vessel. 16.2 g of Me2SiCl2 (126 mmol) was injected through the three-way valve, and the reaction vessel was closed and heated at 120 °C for 4 h. The reaction mixture was then cooled to room temperature. The reaction mixture consisted of a solid phase well separated from the liquid phase. The composition of the silane liquid phase was analyzed by GC. The area ratio H1:H2 of the target product Me2SiHCl (H1) to the undesired intermediate product Me2SiH2 (H2) was determined. The higher the ratio, the more the target product was formed relative to the intermediate product.

[0319] Table 2 below summarizes the reaction parameters and compositions H1:H2. [Table 2]

[0320] This data shows that CaH2 is unreactive under prior art conditions suitable for LiH (see Comparative Examples 1 and 2).

[0321] However, when combined with a sufficiently polar heterocyclic ionic liquid, CaH can be used to selectively synthesize MeSiHCl from MeSiCl under moderate conditions without the need for ethereal solvents or an additional activation step (see Examples 3 and 4).

[0322] Because no organic solvents are present, the volatile silane mixture can be distilled under vacuum from the ionic liquid / CaCl mixture and processed directly. This data also demonstrates that the efficiency of ionic liquids is not a direct function of melting point. Both low-melting (-75 °C for 1-hexyl-3-methylimidazolium chloride) and high-melting (77-79 °C for 1-ethyl-3-methylimidazolium chloride) ionic liquids, when combined with CaH, produce high yields of the target product MeSiHCl, thus enabling the availability of a facile, low-cost synthetic route. Without wishing to be bound by theory, the combination of sufficiently high fluidity of the mixture at the reaction temperature, coupled with sufficiently high polarity, is key to the success of the reaction.

Claims

1. 1. A process for the preparation of one or more silane compounds (A) having at least one Si—H bond, comprising:

1. A process comprising the step of reacting one or more compounds (B) having at least one Si—X bond, where X is a halogen atom, with one or more metal hydrides (C) in the presence of one or more heterocyclic ionic liquids.

2. 2. The process according to claim 1, wherein the compound (A) having at least one Si-H bond is an organomonosilane compound, preferably an organohydridochloromonosilane.

3. The product (A) is selected from monosilanes of the following general formula (I): R ｘ SiH ｙ Cl ｚ (I) In the formula, R is an organyl group, x=1 to 3, preferably 1 to 2; y=1 to 3, preferably 1 to 2; z=0 to 2, preferably 1 to 2, and x+y+z=4, 10. A process according to any preceding claim, wherein preferably R is independently selected from an alkyl group, a cycloalkyl group, or a phenyl group, preferably R is a methyl group.

4. Compound (A) is Me ２ SiHCl, MeSiH ２ Cl, MeSiHCl ２ , HSiCl ３ , and Me ３ SiH, and preferably compound (A) is selected from Me ２ 10. The process according to any of the preceding claims, wherein the compound is SiHCl.

5. The metal hydride (C) is selected from alkali metal hydrides, alkaline earth metal hydrides, or complex metal hydrides containing alkali metal or alkaline earth metal cations, and preferably the metal hydride (C) is LiH, NaH, KH, MgH ２ , CaH ２ and LiAlH ４ and most preferably the metal hydride (C) is selected from CaH ２ wherein preferably the molar ratio of hydride ions of the one or more metal hydrides to halogen atoms, preferably chlorine atoms, of the one or more compounds (B) in the reaction mixture is in the range of from about 0.01 to about 300, more preferably from about 0.1 to about 10, even more preferably from about 0.4 to about 6, and most preferably from about 0.7 to about 3.

6. 10. The process according to any of the preceding claims, wherein the heterocyclic ionic liquid is selected from the group consisting of N-heterocyclic ionic liquids and P-heterocyclic ionic liquids, wherein preferably the heterocyclic ionic liquid is selected from the group consisting of N-heterocyclic aromatic ionic liquids and P-heterocyclic aromatic ionic liquids.

7. 10. The process according to any of the preceding claims, wherein the ionic liquid is selected from 1-substituted imidazolium salts and 1-substituted pyridinium salts, preferably from 1,3-substituted, 1,2,3-substituted, 1,2,3,4-substituted and 1,2,3,4,5-substituted imidazolium salts, more preferably from 1-alkyl-substituted 1,3-substituted, 1,2,3-substituted, 1,2,3,4-substituted and 1,2,3,4,5-substituted imidazolium salts, and even more preferably from ethyl MIMCl and hexyl MIMCl.

8. 10. The process according to any of the preceding claims, wherein the amount of the one or more ionic liquids relative to the one or more compounds (B) in the reaction mixture is in the range of from about 0.1 mol % to about 1500 mol %, preferably from about 0.2 mol % to about 1000 mol %, more preferably from about 0.4 mol % to about 600 mol %, even more preferably from about 0.7 mol % to about 300 mol %, even more preferably from about 0.7 mol % to about 100 mol %, even more preferably from about 2 mol % to about 100 mol %, and most preferably from about 5 mol % to about 100 mol %.

9. Compound (A) is Me ２ SiHCl, compound (B) is Me ２ SiCl ２ , and the metal hydride is CaH ２ 10. A process according to any of the preceding claims,

10. Compound (A) is MeSiH ２ Cl or MeSiHCl ２ , Compound (B) is MeSiCl ３ , and the metal hydride is CaH ２ 9. The process according to any one of the preceding claims 1 to 8, wherein

11. 9. The process according to any of the preceding claims 1 to 8, wherein the process comprises cleavage of one or more Si-Si bonds of one or more di- or polysilane compounds (B) and / or one or more Si-C bonds of one or more carbodisilane compounds (B).

12. Compound (A) is Me ２ SiHCl, MeSiH ２ Cl and MeSiHCl ２ wherein compound (B) is selected from methylchlorodisilanes and methylchloropolysilanes, preferably methylchlorodisilanes, and the metal hydride is preferably CaH ２ or MgH ２ 12. The process according to any one of the preceding claims 1 to 8 and 11, wherein

13. 1. A composition comprising: one or more silane compounds (A') having at least one Si-H bond and at least one Si-X bond, where X is a halogen atom; one or more metal halides (C'), one or more heterocyclic ionic liquids, - optionally one or more silane compounds (A'') having at least two Si-H bonds and no Si-X bonds; A composition comprising:

14. The silane compound (A') is an organomonosilane compound (A') of the following formula: R ｘ SiH ｙ Cl ｚ (I') In the formula, R is an organyl group, x=1 to 2, y=1 or 2, z=1 or 2, and x + y + z = 4, Metal halide (C') is CaCl ２ , and the heterocyclic ionic liquid is an N-heterocyclic quaternary ammonium ionic liquid.

15. The silane compound (A') is Me ２ SiHCl, Metal halide (C') is CaCl ２ and the heterocyclic ionic liquid is an N-heterocyclic quaternary ammonium ionic liquid; N-heterocyclic quaternary ammonium ionic liquids Me ２ the molar ratio to SiHCl ranges from about 0.7 mol % to about 300 mol %, preferably from about 0.7 mol % to about 100 mol %, more preferably from about 2 mol % to about 100 mol %, and most preferably from about 5 mol % to about 100 mol %, and The composition is Me ２ SiH ２ where Me ２ SiHCl Me ２ SiH ２ 15. The composition of claims 13 and 14, wherein the molar ratio of is about 5:1 or greater, preferably about 8:1 or greater, more preferably about 10:1 or greater, even more preferably about 15:1 or greater.

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