Method for producing hydrosilanes

Abstract

Process for the preparation of one or more silane compounds (A) having at least one Si-H bond, comprising the step of subjecting one or more compounds (B) having at least one Si-X bond, where X is a halogen atom, to a reaction 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 preparation (production) of hydridosilanes using metal hydrides as reducing agents in heterocyclic ionic liquids used as both solvents and redistribution promoters, and in particular to methods for preparing organohydridosilanes and organohydridohalosilanes, and in particular to methods using A process for preparing dimethylchlorosilane from dimethyldichlorosilane as a reducing agent, and a composition comprising a hydrohalosilane, a metal halide, and one or more heterocyclic ionic liquids. Background Art

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

[0003] In particular, organohydridosilanes and organohydrochlorosilanes are versatile reagents since they can add to multiple bonds by means of a hydrosilylation reaction.

[0004] In particular, hydrochlorosilanes are valuable building blocks in synthetic silicon chemistry due to their difunctional substitution, which allows either the Si—Cl moiety or the Si—H moiety of such silanes to undergo selective conversion, while the other moiety remains unaffected and can be further functionalized in a subsequent step.

[0005] For example, It is a key intermediate for the synthesis of various functional silicones via hydrosilylation. is a naturally occurring component in the chlorosilane mixture received by the Rochow process. However, The fraction is too low to satisfy the increasing demand resulting from the continuous development of a broad portfolio of highly specialized functional siloxanes.

[0006] There is a need for a direct and efficient one-step method that uses unrestricted and affordable raw materials to obtain organohydridosilanes, e.g. .

[0007] The following concept was proposed and partially used to synthesize silanes containing both Si-Cl and Si-H bonds by reduction:

[0008] 1. Use H2 to reduce Si-Cl bonds to Si-H bonds

[0009] H2 is a low-cost reducing agent, yet, it is found that Si-Cl is reduced to Si-H and depends on very specific catalytic reaction sites and extreme (drastic) conditions. US 5716590 discloses Ni-silicide and H2 combination at elevated temperature provides a path from SiCl silane () to SiH silane. US 4059608 discloses Ni dispersed in HMPT and H2 combination under the presence of the hydrogenolysis cleavage of Si-Si bond produces SiH silane.

[0010] 2. Reduction of Si-Cl using metal hydrides

[0011] JP H03 24091 discloses the use of LiH with The salt mixture is used in a process for reducing chlorosilanes at high temperatures above 350° C. However, LiH is a very expensive metal hydride, and the process is energy-intensive.

[0012] Sn-based systems are disclosed in EP 0 301 678. However, Sn-based systems are expensive, toxic and / or difficult to handle.

[0013] The use of inert solvents is disclosed in EP 0878476. combination, a method of activation by grinding, and the use of ether in US 5455367 is disclosed. , through ultrasonic activation method. It is a volatile compound and is therefore difficult to separate from the desired product. Grinding and sonication require non-standard equipment and thus increase the complexity of the reaction.

[0014] G. Simon et al., J. Organomet. Chem., January 1, 1981, pp. 279-286. Available through At temperatures up to 300 °C, the reduction to .

[0015] US 11008349 proposes a method comprising LiH, an ether solvent and a redistribution catalyst. LiH from form . Then use exist redistributed in the presence of Therefore, excessive For the intermediate Formation of target product In addition, the patent discloses the use of quaternary ammonium compounds in a general manner. replace Acts as a redistribution catalyst.

[0016] In addition, EP3915995 A1 and WO2019 / 060487 A1 disclose methods for using LiH in The present invention relates to a method for producing a compound having at least one Si-H bond in the presence of a heterocyclic ionic liquid. Therefore, the reaction is carried out in the absence of any heterocyclic ionic liquid.

[0017] EP1717241 A1 discloses and Redistribution reaction in the presence of 1-butyl-3-methylimidazolium chloride. Therefore, this method does not involve a reduction reaction of a chlorosilane by a metal hydride followed by a redistribution reaction between the chlorosilane and the resulting hydrosilane, but rather involves a redistribution reaction in which an organochlorosilane is reacted with a hydrochlorosilane having no organic residue. Summary of the Invention

[0018] The present invention, described in detail hereinafter, relates to a process for producing one or more silane compounds (A) having at least one Si—H bond,

[0019] It comprises the steps of subjecting one or more compounds (B) having at least one Si-X bond, wherein X is a halogen atom, to a reaction with one or more metal hydrides (C) in the presence of one or more heterocyclic ionic liquids. DETAILED DESCRIPTION

[0020] The process according to the present invention is a process for producing one or more silane compounds (A) having at least one Si—H bond, comprising the step of subjecting one or more compounds (B) having at least one Si—X bond to a reaction with one or more metal hydrides (C) in the presence of one or more heterocyclic ionic liquids, wherein X is a halogen atom.

[0021] 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, wherein X is a halogen, i.e. a fluorine, chlorine, bromine or iodine group, preferably chlorine, as well as mixtures of two or more such compounds, which are used as starting materials in the process of the present invention.

[0022] Thus, the starting material may be selected from monosilanes, disilanes, oligosilanes or polysilanes, and carbodisilanes having at least one Si-X bond, wherein 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) in the process according to the invention.

[0023] The method of the present invention can be applied to any type of silane compound (B), including silanes (B) having at least one Si-X bond, wherein the substituents are selected only from halogen atoms and hydrogen atoms, but preferably the method of the present invention is applied to organosilanes, i.e. compounds (B) having at least one Si-R bond, wherein R is an organic group. The term "organic group" as defined herein refers to any organic group having one free valence at a carbon atom, and thus the organic group R is bonded to the Si atom of the silane via a carbon atom.

[0024] According to one embodiment of the present invention, the organic group R comprises an optionally substituted, but preferably unsubstituted, group independently selected from: alkyl, aryl, alkenyl, alkynyl, alkaryl, aralkyl, aralkenyl, aralkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, cycloaralkyl, cycloaralkenyl and cycloaralkynyl, even more preferably selected from alkyl, cycloalkyl, alkenyl and aryl, even further preferably selected from methyl, ethyl, vinyl and phenyl, and most preferably R is methyl.

[0025] As defined herein, the term "alkyl" encompasses unbranched n-alkyl, branched alkyl and cycloalkyl 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 are even further preferred, in particular 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.

[0026] As defined herein, the term "aryl" encompasses all groups derived from monocyclic and polycyclic aromatic hydrocarbons by removing a hydrogen atom from a ring carbon atom.

[0027] According to one embodiment of the present invention, an aryl group having 6 to 22 carbon atoms, in particular a phenyl group, is preferred.

[0028] As defined herein, the term "alkenyl" encompasses unbranched, branched and cyclic hydrocarbon residues having one or more carbon-carbon double bonds. According to one 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 are even further preferred, in particular vinyl and allyl.

[0029] The one or more halogen atoms X bonded to one or more Si atoms of the silane compound (B) are selected from fluorine atoms, chlorine atoms, bromine atoms and iodine atoms, preferably chlorine, wherein the silane compound B may contain two or more different types of halogen atoms, but preferably the silane compound B contains one type of halogen atom bonded to one or more Si atoms. Although silanes (B) containing all of the above-mentioned types of halogen atoms can be subjected to the method of the present invention, in one embodiment of the present invention, it is preferred that the halogen atoms X are selected from iodine atoms, bromine atoms and chlorine atoms, more preferably selected from bromine atoms and chlorine atoms, and most preferably all halogen atoms X of the silane compound (B) are selected from chlorine atoms.

[0030] In addition, according to one embodiment of the present invention, the silane compound (B) is preferably substituted only with halogen substituents or organic substituents and halogen substituents, that is, the compound (B) is preferably a perhalogenated silane and especially a perhalogenated organosilane.

[0031] More preferably, compound (B) is a perchlorosilane and in particular a perchloroorganosilane, even more preferably selected from tetrachlorosilane and organochloromonosilane 、 、 , wherein R is an organic group. Even more preferably, compound (B) is selected from and , most preferably, compound (B) is .

[0032] The silane compound (B) having at least one Si-X bond may be a monosilane, a disilane, a polysilane and a carbodisilane. As defined herein, the term polysilane encompasses all types of silanes having three or more silicon atoms bonded to one another in a linear manner, i.e. in the case of trisilane forming, for example, part.

[0033] Monosilane:

[0034] The monosilane (B) having at least one Si-X bond used as a starting material may be a monosilane having only substituents selected from one or more halogen atoms X (preferably chlorine atoms) and optionally hydrogen atoms, or a monosilane having substituents selected from one or more halogen atoms (preferably chlorine atoms), one or more organic group substituents R and optionally hydrogen atoms. In an organomonosilane having two or more groups R, the organic groups R may be the same or different. The one or more organic groups R are optionally substituted, but preferably unsubstituted, groups independently selected from: alkyl, aryl, alkenyl, alkynyl, alkaryl, aralkyl, aralkenyl, aralkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, cycloaralkyl, cycloaralkenyl and cycloaralkynyl, even more preferably selected from alkyl, cycloalkyl, alkenyl and aryl, even further preferably selected from methyl, ethyl, vinyl and phenyl, and most preferably R is methyl.

[0035] Preferred monosilanes bearing only halogen and hydrogen atoms are 、 、 、 、 and ,in and is the most preferred.

[0036] In one embodiment, the monosilanes (B) preferably having at least one Si—X bond are organomonosilanes, ie they have one or more substituents R, more preferably R is an unsubstituted alkyl group or a phenyl group.

[0037] According to one embodiment of the present invention, preferably the organosilane (B) has the general formula

[0038] ,

[0039] wherein X is a halogen atom, preferably chlorine,

[0040] R is an organic group,

[0041] a=1 to 3,

[0042] b = 0 to 2,

[0043] c = 1 to 3, and

[0044] .

[0045] Although the method according to the present invention is also applicable to the reduction of the general formula Organic halogenated monosilanes, especially , but in one embodiment, the method is preferably applied to the general formula and Organic dihalogenated monosilanes and organic trihalogenated monosilanes, especially and wherein R is an organic group and X is a halogen atom as defined above, and R is preferably selected from unsubstituted C1-C12 alkyl, unsubstituted C1-C12 alkenyl and C6-C12 aryl, more preferably selected from methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, cyclopentyl, cyclohexyl, norbornyl, isopropyl, isobutyl, tert-isobutyl, isopentyl, vinyl, allyl, phenyl and naphthyl, most preferably selected from methyl, vinyl and phenyl. wherein the organodihalosilanes and organotrihalosilanes as described above can be fully hydrogenated by replacing all Si-X bonds with Si-H bonds in the reaction with a metal hydride, but preferably in the process according to the invention a group of the general formula is obtained 、 and , more preferably the general formula 、 and The corresponding organohydrohalosilanes.

[0046] In one embodiment, the most preferred monosilane (B) is and , and the most preferred product (A) of the process according to an embodiment of the present invention based on the monosilane starting material (B) is 、 and .

[0047] Disilane:

[0048] The disilane (B) having at least one Si-X bond used as a starting material may be a disilane having only substituents selected from one or more halogen atoms X (preferably chlorine atoms) and optionally hydrogen atoms, or a disilane having substituents selected from one or more halogen atoms (preferably chlorine atoms), one or more organic group substituents R, and optionally hydrogen atoms. In an organodisilane having two or more groups R, the organic groups R may be the same or different. The one or more organic groups R are optionally substituted, but preferably unsubstituted, groups selected from alkyl, aryl, alkenyl, alkynyl, alkaryl, aralkyl, aralkenyl, aralkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, cycloaralkyl, cycloaralkenyl, and cycloaralkynyl, even more preferably selected from alkyl, cycloalkyl, alkenyl, and aryl, even more preferably selected from methyl, ethyl, vinyl, and phenyl, and most preferably R is methyl.

[0049] Preferred disilanes bearing only halogen and hydrogen atoms are 、 and ,in is the most preferred.

[0050] Preferably, the disilanes (B) having at least one Si—X bond are organodisilanes, ie they have one or more substituents R, further preferably R is an unsubstituted alkyl group or a phenyl group.

[0051] According to one embodiment of the present invention, preferably the organodisilane (B) has the general formula

[0052] wherein R is an organic group as defined above, and X is a halogen atom, preferably chlorine,

[0053] e=1 to 5,

[0054] f = 0 to 4,

[0055] g = 1 to 5, and

[0056] .

[0057] Disilanes of the following general empirical formula:

[0058]

[0059] It can also be described by the following structural formula:

[0060]

[0061] wherein the substituents R' are independently selected from organic radicals R as defined above, hydrogen atoms and halogen atoms X, preferably chlorine, wherein 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 .

[0062] As defined herein, the term "empirical formula" is intended to mean that these formulas do not represent structural formulas, but rather are summaries of chemical groups or atoms present in a molecule. For example, the empirical formula The following structural formula may be included:

[0063] and .

[0064] According to one embodiment of the present invention, preferably the organodisilane (B) only carries an organic group substituent R and a halogen substituent X, and more preferably the organodisilane is selected from the group having the formula 、 and disilane, even more preferably 、 and , wherein R is as defined above. Further preferably, wherein R is selected from alkyl, aryl and alkenyl, even more preferably selected from phenyl, vinyl, ethyl and methyl.

[0065] Although in the process according to the invention all halogen atoms of the disilane compound (B) can be replaced by hydrogen atoms, in one embodiment it is preferred that the organohalodisilane is only partially hydrogenated to produce an organohydrohalodisilane (A), in particular an organohydrochlorodisilane (A).

[0066] In parallel with the hydrogenation, preferably partial hydrogenation, and the redistribution reaction promoted by the heterocyclic ionic liquid by the reaction of the silane starting material (B) with the metal hydride (C) in the process, the organohalogenated disilane (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. In the cleavage reaction of the disilane, the Si-Si bond of the compound is broken, resulting in the formation of a monosilane.

[0067] The rate of the cleavage reaction depends on the substitution pattern of compound (B), for example the number and type of organic group residues R present in the disilane compound, and the reaction conditions, in particular the type of heterocyclic ionic liquid, reaction temperature and reaction time.

[0068] By cleavage of the disilane compound (B) and its hydrogenated analogues, monosilanes (A) having at least one Si—H bond can be obtained from the disilane (B) in the process according to one embodiment of the invention, preferably organohydrohalogenated monosilanes, even more preferably of the formula 、 and The organohydrochloromonosilane, most preferably 、 and .

[0069] Particularly preferred organodisilanes (B) are 、 and , and the preferred product obtained therefrom in the method according to an embodiment of the present invention is 、 、 and .

[0070] Polysilane:

[0071] The polysilane (B) having at least one Si-X bond used as a starting material may be a polysilane having only substituents selected from one or more halogen atoms X (preferably chlorine atoms) and optionally hydrogen atoms, or a polysilane having substituents selected from one or more halogen atoms (preferably chlorine atoms), one or more organic group substituents R, and optionally hydrogen atoms. In an organopolysilane having two or more groups R, the organic groups R may be the same or different. The organic group R is optionally substituted, but preferably unsubstituted, and is selected from the group consisting of alkyl, aryl, alkenyl, alkynyl, alkaryl, aralkyl, aralkenyl, aralkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, cycloaralkyl, cycloaralkenyl, and cycloaralkynyl, even more preferably selected from alkyl, cycloalkyl, alkenyl, and aryl, even more preferably selected from methyl, ethyl, vinyl, and phenyl, and most preferably R is methyl.

[0072] According to one embodiment of the present invention, the polysilane is preferably selected from oligosilanes having a linear or branched silane skeleton, wherein q = 3 to 7, and the silicon atoms are bonded to each other by single bonds, and the compound has the following general empirical formula

[0073] ,

[0074] in

[0075] R is an organic group,

[0076] X is a halogen atom, preferably a chlorine atom,

[0077]

[0078] p = 0 to (2q + 1)

[0079] r = 0 to (2q + 1)

[0080] s=1 to (2q+2)

[0081] r+s=(2q+2)-p.

[0082] Preferred polysilanes without organic residues are 、 、 、 and .

[0083] Preferably, the polysilane according to one embodiment of the present invention has one or more substituents R, and more preferably, R is an unsubstituted alkyl group or a phenyl group.

[0084] According to one embodiment of the present invention, preferably these organopolysilanes (B) carry only organic group substituents R and halogen substituents X, more preferably said organopolysilane is selected from the group of organopolysilanes in which R = alkyl, aryl and alkenyl, even more preferably from the group of organopolysilanes in which R = phenyl, vinyl and methyl, and most preferably the substituents are selected from methyl and chlorine.

[0085] Although in the process according to the invention all halogen atoms of the polysilane compound (B) can be replaced by hydrogen atoms, in one embodiment it is preferred that the organohalopolysilane is only partially hydrogenated, thereby producing an organohydrogenohalopolysilane, in particular an organohydrogenochloropolysilane.

[0086] Similar to the description of the cleavage reaction of disilanes above, the organohalogenated polysilane (B) and the products obtained therefrom by hydrogenation and redistribution can be cleaved in the method according to one embodiment of the present invention by cleaving one or more Si-Si bonds, thereby producing silanes with a lower number of silicon atoms, in particular organomonosilanes, more preferably organohydrohalogenated monosilanes, and even more preferably formula 、 and The organohydrochloromonosilane, most preferably 、 and .

[0087] In the process according to one embodiment of the invention, the preferred product obtained from the organohalogenated polysilane (which is usually obtained as a complex mixture, for example as a The by-product in the direct process is 、 、 、 , wherein R is an organic group, preferably an alkyl group. Most preferably, the product is 、 、 and .

[0088] Carbodisilane:

[0089] The carbodisilanes (B) having at least one Si—X bond used as starting material in the process according to the invention have the general empirical formula

[0090]

[0091] wherein R is an organic group as defined above,

[0092] m = 0 to 5,

[0093] n=0 to 5,

[0094] o=1 to 6,

[0095] z = 1 or 2,

[0096] and

[0097] .

[0098] In carbodisilanes carrying two or more radicals R, the organic radicals R may be identical or different.

[0099] The organic group R is an optionally substituted, but preferably unsubstituted, group selected from the group consisting of alkyl, aryl, alkenyl, alkynyl, alkaryl, aralkyl, aralkenyl, aralkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, cycloaralkyl, cycloaralkenyl and cycloaralkynyl, even more preferably selected from the group consisting of alkyl, cycloalkyl, alkenyl and aryl, even further preferably selected from the group consisting of methyl, ethyl, vinyl and phenyl, and most preferably R is methyl. Although preferred carbodisilanes with only halogen residues are or , where the latter can be obtained by reacting However, it is generally preferred that the carbodisilane according to the embodiment of the present invention has one or more substituents R, and more preferably R is an unsubstituted alkyl group or a phenyl group.

[0100] According to an embodiment of the present invention, it is preferred that these carbodisilanes (B) carry only organic substituents R and halogen substituents X, more preferably the carbodisilanes are selected from the group of carbodisilanes in which R = alkyl, aryl and alkenyl, even more preferably from the group of carbodisilanes in which R = phenyl, vinyl, ethyl and methyl, and most preferably the substituents are selected from methyl and chlorine.

[0101] Examples of particularly preferred carbodisilanes are 、 、 、 and .

[0102] Although in the process according to the invention all halogen atoms of the carbodisilane compound (B) may be replaced by hydrogen atoms, in one embodiment it is preferred that the carbodisilane is only partially hydrogenated, thereby producing an organohydrogenated halocarbodisilane, in particular an organohydrogenated chlorocarbodisilane.

[0103] According to one embodiment of the present invention, the organocarbodisilane may also serve as a starting material (B) for the production of an organomonosilane, preferably an organohydrohalogenated monosilane, even more preferably of the formula 、 and The organohydrochloromonosilane, most preferably 、 and In contrast to the cleavage of disilanes and carbodisilanes, the cleavage reaction of the above-mentioned carbodisilanes leading to the formation of monosilanes requires the cleavage of one or more Si-C bonds.

[0104] From the above-mentioned class of silane compounds which have one or more Si—X bonds (B) and which can therefore be used as starting materials in the process according to the invention, in one embodiment, preference is given to subjecting one or more of the following silanes to the process:

[0105] - monosilanes selected from the following formulae:

[0106] 、 and ;

[0107] - a disilane selected from the following formula:

[0108] 、 、 、 、 ;

[0109] - oligomeric silanes selected from the following formulae:

[0110] 、 、 、 、 、 、 、 、 ;

[0111] - carbodisilane selected from the following formula:

[0112] 、 、 、 and 、 、 、 、 、 .

[0113] 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 a plurality of such compounds (A) is the desired product obtained in the process of the present invention by reacting the starting material compound (B) with one or more metal hydrides (C) in the presence of one or more heterocyclic ionic liquids.

[0114] The type of compound (A) obtained in the process according to the invention is determined primarily by the choice of the starting material, i.e. the compound or compounds (B) subjected to the process, and, in addition, the type of compound formed and / or the distribution of the various compounds (A) obtained can be controlled by the specific reaction conditions applied.

[0115] In the process according to the invention, the starting material silane compound (B) is subjected to a reaction 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 hydrogenated products.

[0116] As defined herein, the term "subjecting to reaction with" is to be understood as any manner of contacting compound (B) and metal hydride (C) in the presence of one or more heterocyclic ionic liquids such that the one or more silane compounds (B) and the one or more metal hydrides (C) react.

[0117] The metal hydride (C) acts as a hydride donor and is converted into a similar metal halide, while at least one Si-X bond of the one or more compounds (B) is replaced by a Si-H bond during the hydrogenation reaction.

[0118] 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 binary metal hydrides. The term "complex metal hydride" refers to a metal salt containing a hydride anion, for example, as a hydridometalate anion, such as or Typically, complex metal hydrides contain more than one type of metal or metalloid. As defined herein, the term "metalloid" includes the elements boron, silicon, germanium, arsenic, antimony, tellurium, carbon, aluminum, selenium, polonium, and astatine.

[0119] The term "organometallic hydride reagent" refers to a compound containing a bond between a carbon atom and a metal atom, and which is capable of donating at least one hydride anion used in the reaction of the silane compound (B), resulting in at least one Si-X bond being replaced by a Si-H bond. As defined herein, a binary metal hydride is a metal hydride consisting of only a cation and a hydride ion of a specific metal.

[0120] In one embodiment of the present invention, the metal hydride is preferably selected from binary metal hydrides or composite metal hydrides, more preferably selected from alkali metal hydrides, alkaline earth metal hydrides and composite metal hydrides comprising alkali metal or alkaline earth metal cations, even more preferably selected from the group consisting of lithium hydride, sodium hydride, potassium hydride, magnesium hydride, calcium hydride, even more preferably selected from magnesium hydride, sodium hydride or calcium hydride, most preferably the metal hydride is calcium hydride.

[0121] The molar ratio of the hydride ions of the one or more metal hydrides relative to the halogen atoms of the one or more compounds (B) allows controlling the degree of replacement of the Si-X bonds in the starting material compound (B) and thus determines which product silane compound (A) is predominantly formed in the process of the invention.

[0122] Addition of hydride ions in an equimolar amount or in excess relative to the Si-X bonds in compound (B), i.e., a molar ratio of hydride ions to Si-X bonds equal to or greater than 1, to the metal hydride (C) is expected to result in complete hydrogenation of the halosilane, unless the hydride ions are otherwise consumed in the reaction mixture. Addition of hydride ions in a substoichiometric amount, i.e., at a molar ratio of less than 1, results in partial hydrogenation of the starting material (B) in the case of one or more compounds having more than one Si-X bond, and incomplete conversion in the case of the starting material (B) having only a single Si-X bond.

[0123] The reaction of the method resulting 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, heterocyclic ionic liquids are salts containing heterocyclic anions and / or cations that are liquid under the conditions of the method according to the invention. Typically, the melting point of the salt or ionic liquid is 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. The melting point is measured at atmospheric pressure using a digital device, such as an electrothermal device.

[0124] The selection of the ionic liquid(s) is made based on parameters such as melting point, polarity, compatibility with the Si compound to be hydrogenated, commercial availability, ease of purification and recyclability.

[0125] Without wishing to be bound by any theory, it is assumed that the presence of one or more heterocyclic ionic liquids promotes and accelerates the reaction of one or more compounds (B) and one or more metal hydrides (C), in particular by removing metal halides formed on the surface of the metal hydride particles during the hydrogenation reaction. This makes the application of other activation means such as grinding, sonication or the addition of other activators superfluous, thereby significantly accelerating the hydrogenation process. In addition, the presence of heterocyclic ionic liquids allows the ratio of the different silane product compounds (A) formed by hydrogenation to be controlled by promoting redistribution reactions between the different hydride species of the silane compounds formed and between the different hydride species of the silane compounds formed and the starting material silane compound (B).

[0126] According to one embodiment of the present invention, the heterocyclic structure of the ionic liquid is not limited in any way except for the following restriction: a cyclic structure containing one or more heteroatoms must be present in the ionic liquid, i.e., it must include at least one atom other than carbon and hydrogen atoms as a ring member, wherein the cyclic structure may be aromatic or non-aromatic.

[0127] Ring structures consisting only of carbon atoms having one or more heteroatom substituents are not considered to be heterocycles according to the present invention. The heteroatoms are generally selected from oxygen atoms (O), sulfur atoms (S), phosphorus atoms (P) and nitrogen atoms (N), with P-heterocycles and N-heterocycles being generally preferred.

[0128] While there is no limitation on the ring size of the heterocyclic structure, the number of heteroatoms present in the heterocyclic ring, and the type of heteroatoms, it is preferred that the heterocyclic structure be a 5- or 6-membered ring containing one or two heteroatoms, wherein the heteroatoms are preferably selected from N atoms and P atoms. These structures may be aromatic or non-aromatic.

[0129] According to one embodiment of the present invention, the heterocyclic ionic liquid is preferably selected from N-heterocyclic ionic liquids and P-heterocyclic ionic liquids.

[0130] As defined herein, N-heterocyclic ionic liquids and P-heterocyclic ionic liquids are heterocyclic ionic liquids as defined above, wherein 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.

[0131] The P-heterocycle or N-heterocycle, respectively, may be present in the cation, anion, or both the cation and anion of the ionic liquid, but preferably the P-heterocycle or N-heterocycle is contained in the cation of the ionic liquid.

[0132] According to one embodiment 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, pyrrole salts and triazolium salts.

[0133] The general structure of substituted imidazolium salts is

[0134]

[0135] where R 1 and R 2 is an organic residue, preferably a C1-C12 alkyl residue, and Z can be any type of anion, preferably selected from chloride, bromide, acetate, trifluoroacetate, OTf (trifluoromethanesulfonate), anions of tetrafluoroborate, hexafluorophosphate, or methanesulfonate;

[0136] The general structure of N-substituted pyridine compounds is

[0137]

[0138] where R 3 is an organic residue, preferably a C1-C12 alkyl residue, and Z can be any type of anion, preferably selected from chloride, bromide, acetate, trifluoroacetate, OTf (trifluoromethanesulfonate), anions of tetrafluoroborate, hexafluorophosphate, or methanesulfonate;

[0139] The general structure of a disubstituted pyrrolium salt is

[0140]

[0141] where R 4 and R 5 is an organic residue, preferably a C1-C12 alkyl residue, and Z can be any type of anion, preferably selected from chloride, bromide, acetate, trifluoroacetate, OTf (trifluoromethanesulfonate), anions of tetrafluoroborate, hexafluorophosphate, or methanesulfonate;

[0142] Replaced The general structure of triazolium salts is

[0143]

[0144] where R 6 and R 7 is an organic residue, preferably a C1-C12 alkyl residue, and Z can be any type of anion, preferably selected from chloride, bromide, acetate, trifluoroacetate, OTf (trifluoromethanesulfonate), anions of tetrafluoroborate, hexafluorophosphate, or methanesulfonate;

[0145] As defined herein, each of the structures shown above or a ring carbon atom thereof may independently also carry further substituents instead of hydrogen substituents, wherein the substituents are preferably selected from halogen substituents and alkyl groups, more preferably from C1-C12 alkyl groups.

[0146] Specific examples of the imidazolium salt include 1-ethyl-3-methylimidazolium chloride, 1-butyl-3-methylimidazolium chloride and 1-hexyl-3-methylimidazolium chloride, specific examples of the pyridinium salt include N-butylpyridinium chloride, N-hexylpyridinium chloride and N-octylpyridinium chloride, specific examples of the pyrrolium salt include Examples of the triazolium salts include dimethylpyrrolium chloride, N-methyl-N-ethylpyrrolium chloride, N-methyl-N-butylpyrrolium chloride, and N-methyl-N-hexylpyrrolium chloride, and specific examples of the triazolium salts are N-butyl-N′-methyl-C-methyltriazolium chloride and N-butyl-N′-methyl-C-butyltriazolium chloride.

[0147] 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.

[0148] The general structure of substituted morpholinium salts is

[0149]

[0150] where R 8 and R 9 is an organic residue, preferably a C1-C12 alkyl residue, and Z can be any type of anion, preferably selected from chloride, bromide, acetate, trifluoroacetate, OTf (trifluoromethanesulfonate), anions of tetrafluoroborate, hexafluorophosphate, or methanesulfonate;

[0151] The general structure of substituted piperidinium compounds is

[0152]

[0153] where R 10 and R 11 is an organic residue, preferably a C1-C12 alkyl residue, and Z can be any type of anion, preferably selected from chloride, bromide, acetate, trifluoroacetate, OTf (trifluoromethanesulfonate), anions of tetrafluoroborate, hexafluorophosphate, or methanesulfonate;

[0154] The general structure of substituted pyrrolidinium salts is

[0155]

[0156] where R 12 and R 13 is an organic residue, preferably a C1-C12 alkyl residue, and Z can be any type of anion, preferably selected from chloride, bromide, acetate, trifluoroacetate, OTf (trifluoromethanesulfonate), anions of tetrafluoroborate, hexafluorophosphate, or methanesulfonate;

[0157] The general structure of piperazinium monosalt is

[0158]

[0159] where R 14 、R 15 and R 16 is an organic residue, preferably a C1-C12 alkyl residue, and Z can be any type of anion, preferably selected from chloride, bromide, acetate, trifluoroacetate, OTf (trifluoromethanesulfonate), anions of tetrafluoroborate, hexafluorophosphate, or methanesulfonate;

[0160] The general structure of piperazinium disalt is

[0161]

[0162] where R 14 、R 15 、R 16 and R 17is an organic residue, preferably a C1-C12 alkyl residue, and Z can be any type of anion, preferably selected from chloride, bromide, acetate, trifluoroacetate, OTf (trifluoromethanesulfonate), (methanesulfonate), TFSI (bis(trifluoromethylsulfonyl)imide), tetrafluoroborate, or hexafluorophosphate, or methanesulfonate anions.

[0163] As defined herein, the ring carbon atoms of the structure shown above may each independently also carry further substituents instead of hydrogen substituents, wherein the substituents are preferably selected from halogen substituents and alkyl groups, more preferably from C1-C12 alkyl groups.

[0164] Specific examples of morpholinium salts include Specific examples of the piperidinium salts include 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 the pyrrolidinium salt include N,N-dimethyl-pyrrolidinium chloride, N-methyl-N-ethyl-pyrrolidinium chloride, N-methyl-N-butyl-pyrrolidinium chloride and N-methyl-N-hexyl-pyrrolidinium chloride, specific examples of the piperazinium monosalt include Trimethylpiperazinium chloride, Dimethyl-N-ethyl-piperazinium chloride, Dimethyl-N-butyl-piperazinium chloride and Specific examples of dimethyl-N-hexyl-piperazinium chloride, piperazinium disalts include Tetramethyl-piperazinium dichloride, Dimethyl- Diethylpiperazinium dichloride, Dimethyl- Dibutylpiperazinium dichloride and Dimethyl- Dihexyl-piperazinium chloride.

[0165] According to one embodiment of the present invention, the P-heterocyclic ionic liquid may be selected from aromatic P-heterocyclic ionic liquids and non-aromatic P-heterocyclic ionic liquids. Examples of aromatic P-heterocyclic ionic liquids according to embodiments of the present invention are ionic liquids that are phospholium salts (containing a five-membered ring with one P heteroatom) and phosphininium salts (containing a six-membered ring with one P heteroatom), which are exemplified by the following specific structures:

[0166]

[0167] Examples of non-aromatic P-heterocyclic ionic liquids according to embodiments are ionic liquids selected from phospholanium salts (containing a saturated five-membered ring with one P heteroatom) and phosphinanium salts (containing a saturated six-membered ring with one P heteroatom).

[0168] The general structure of phospholanium salts is

[0169]

[0170] where R 18 and R 19 is an organic residue, preferably a C1-C12 alkyl residue, and Z can be any type of anion, preferably selected from chloride, bromide, acetate, trifluoroacetate, OTf (trifluoromethanesulfonate), anions of tetrafluoroborate, hexafluorophosphate, or methanesulfonate;

[0171] The general structure of phosphonium salts is

[0172]

[0173] where R 20 and R 21 is an organic residue, preferably a C1-C12 alkyl residue, and Z can be any type of anion, preferably selected from chloride, bromide, acetate, trifluoroacetate, OTf (trifluoromethanesulfonate), (methanesulfonate), TFSI (bis(trifluoromethylsulfonyl)imide), tetrafluoroborate, or hexafluorophosphate, or methanesulfonate anions.

[0174] According to an embodiment of the present invention, the structure shown above may further independently carry additional substituents on carbon ring atoms, preferably halogen substituents and alkyl substituents.

[0175] Specific examples of phospholanium salts include Dimethyl-phospholanium chloride and P-methyl-P-butyl-phospholanium chloride (five-membered ring), specific examples of phosphonium salts include Dimethyl-phosphonium chloride (six-membered ring) and P-methyl-P-butyl-phosphonium chloride (six-membered ring).

[0176] According to one embodiment of the present invention, the cation of the ionic liquid preferably comprises a heterocyclic structure. The anion of the ionic liquid compound may be selected from any type of one or more organic and inorganic anions, wherein monovalent cations are preferred.

[0177] An example of an anion of an ionic liquid compound is F - 、Cl - Br - , I - 、 、heptachlorodialuminate( ), hexafluoroantimonate, hexafluoroarsenate, fluorosulfonate, hexafluorophosphate ( ), tetrafluoroborate ( ), bisperfluoroalkylsulfonamides (particularly methyl, butyl and nonyl, most particularly bis(trifluoromethylsulfonyl)imide ( , TFSI)) and perfluoroalkylsulfonate (especially trifluoromethanesulfonate), tetrachloroborate, dicyanamide anion ( ), acetate, trifluoroacetate, methanesulfonate, tetrafluoroborate, hexafluorophosphate, lactate, citrate, sulfate, phosphate, methylsulfate, ethylsulfate, bisulfate, carbonate, and methylcarbonate.

[0178] Preferably, the anion is selected from chloride, bromide, acetate, trifluoroacetate, OTf (trifluoromethanesulfonate), (methanesulfonate), TFSI (bis(trifluoromethylsulfonyl)imide), tetrafluoroborate, or hexafluorophosphate, more preferably selected from chlorine, tetrafluoroborate ( ), hexafluorophosphate ( ), bis(trifluoromethanesulfonimide) ) and trifluoromethanesulfonate (OTf).

[0179] In order to obtain a high proportion of a specific partially hydrogenated halosilane, a substoichiometric amount of hydride ions is provided by adding a metal hydride. In parallel with and / or after the reduction reaction, a product mixture is formed by an equilibrium process involving a redistribution reaction of the compound (A) formed in the process and the starting material (B) present in the reaction mixture.

[0180] As defined herein, the term "redistribution reaction" describes the redistribution of hydrogen and halogen substituents, preferably hydrogen and chlorine substituents, bonded to silicon atoms of one or more silane compounds by exchange of these substituents. The exchange can in particular be carried out by , monitored by GC and / or GC / MS. Preferably, an organohydrohalosilane having both hydrogen and halogen substituents, preferably both hydrogen and chlorine substituents, at the silicon atom is obtained by a redistribution reaction of a silane having, in addition to the organyl substituent, mainly or exclusively chlorine substituents at the silicon atom and a silane having, in addition to the organyl substituent, only or mainly hydrogen substituents at the silicon atom.

[0181] The redistribution reaction of silanes as defined herein includes in particular the comproportionation of two different organosilanes, in particular organosilanes having only halogen as further substituents and organosilanes having only hydrogen as further substituents), wherein a specific halohydroorganosilane is formed, for example

[0182]

[0183] .

[0184] The redistribution reaction can be viewed as the opposite of the undesirable disproportionation reaction, in which, for example, a chlorohydromethylsilane reacts with itself to form two different methylsilanes (one with only chlorine as an additional substituent and one with only hydrogen as an additional substituent):

[0185]

[0186] .

[0187] The redistribution reaction is catalyzed or promoted by one or more heterocyclic ionic liquids. Although the presence of other different redistribution catalysts is within the scope of the present method, in one embodiment it is preferred that no other redistribution catalysts are added in addition to the heterocyclic ionic liquids.

[0188] As defined above, the starting material of the method according to the present invention is a silane compound (B) having at least one Si-X bond, which includes monosilane, disilane, carbodisilane and polysilane, wherein the silane compound may or may not contain an organic substituent. Although the term "organic" is defined herein to mean any organic substituent (regardless of the functional type) bonded to a silicon atom of the compound (B) via its carbon atom, in one embodiment of the present invention, the organic group is preferably 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, even more preferably alkyl, cycloalkyl, alkenyl and aryl, even further preferably methyl, ethyl, vinyl and phenyl, and most preferably R is methyl (also abbreviated herein as Me).

[0189] According to an embodiment of the present invention, it is preferred that the process results in the formation of one or more halogenated hydroorganosilanes, in particular chlorohydroorganosilanes. 、 and .

[0190] Such compounds are highly attractive and valuable due to their bifunctional nature, which makes them useful reagents in synthesis. The most preferred silane compound (A) having at least one Si-H bond obtained in the process according to an embodiment of the present invention is 、 and .

[0191] The aforementioned difunctional halohydrogenated organomonosilane compounds can generally be obtained by subjecting the monosilane (B) described above to the method of the present invention, but in one embodiment, the method is also suitable for obtaining organohydrogenated halomonosilanes by subjecting the corresponding disilanes, polysilanes and carbodisilanes (B) described above to.

[0192] This requires that a fragmentation reaction takes place in the method according to an embodiment of the present invention.

[0193] The term "fragmentation reaction" is used above to describe the conversion by which disilane (B), polysilane (B) and carbodisilane (B) as described above react to produce monosilane (A). In the case of disilane and polysilane, the term "fragmentation reaction" also means that according to the present invention, the fragmentation of the aforementioned substrate is achieved by destroying the bonds connecting the silicon atoms of these disilane and polysilane or their fully or partially hydrogenated derivatives. In the case of carbodisilane, the term "fragmentation reaction" means that the fragmentation reaction is achieved by breaking one or two Si-C bonds between the silyl group in the carbodisilane and the methylene or ethylene group connecting the silyl group. In order to promote the fragmentation reaction as described above, an additional fragmentation promoter or fragmentation catalyst can be added to the reaction mixture of the method according to an embodiment of the present invention.

[0194] Such fragmentation promoters or catalysts are preferably selected from:

[0195] - Group 15 onium compounds , wherein each R is independently hydrogen or an organic group, Q is nitrogen, phosphorus, arsenic, antimony or bismuth, and X is a halogen selected from F, Cl, Br and I,

[0196] -heterocyclic amines,

[0197] -heterocyclic ammonium halides,

[0198] - A mixture of RX,

[0199] wherein R is as defined above, and X is as defined above,

[0200] - alkali metal halides,

[0201] - alkaline earth metal halides,

[0202] - alkali metal hydrides,

[0203] - alkaline earth metal hydrides or mixtures thereof.

[0204] However, according to one embodiment of the present invention, it is preferred that no further fragmentation catalysts or fragmentation promoters are added in addition to the heterocyclic ionic liquid used in the process according to the invention.

[0205] In general, 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, in the case of cleavage involving disilanes and polysilanes, the type of monosilane (A) obtained is primarily determined by the substitution pattern of the disilanes and polysilanes and the amount of metal hydride used.

[0206] In a most preferred embodiment of the present invention, Experience and The reaction is carried out in the presence of one or more heterocyclic ionic liquids at a temperature of about 0°C to about 150°C to produce , wherein the heterocyclic ionic liquid is preferably selected from N-heterocyclic aromatic quaternary ammonium ionic liquids, more preferably selected from ionic liquids of imidazolium salts, even more preferably selected from 1-substituted imidazolium salts, even further preferably selected from 1-alkyl-3-methylimidazolium chlorides, most preferably selected from ethyl MIMC1, butyl MIMC1 and hexyl MIMC1.

[0207] In one embodiment according to the present invention, 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.

[0208] 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, Si-Cl bonds, Si-Br bonds, and Si-I bonds can be easily replaced in the method according to an embodiment of the present invention. Preferably, at least one X in the silane compound (B) represents a chlorine atom, and more preferably, all substituents X in the silane compound (B) are chlorine atoms.

[0209] In one embodiment of the present invention, the compound (A) having at least one Si—H bond is an organomonosilane compound, preferably an organohydrogenated chloromonosilane.

[0210] The target compound according to this embodiment is a monosilane carrying one or more organic groups R and one or more hydrogen substituents.

[0211] With formula 、 and The organohydromonosilane and the organohydrogen monosilane having the formula 、 and Both of the organohydrohalosilanes are prepared according to this embodiment of the present invention. Wherein, the substituent R is independently selected from an organic group, preferably selected from a C1-C12 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.

[0212] According to an embodiment, X is independently selected from F, Cl, Br or I substituents, preferably each X represents a Cl atom.

[0213] According to an embodiment, it is preferred that the compound (A) having at least one Si-H bond is an organohydrochloromonosilane, i.e. an organosilane having one or more hydrogen atoms and one or more chlorine atoms as substituents. Therefore, the preferred target compound (A) has the general formula 、 and , wherein R is independently selected from an organic group, preferably selected from a C1-C12 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. In the case of silane compounds (A), preferably both R represent the same substituent, most preferably methyl. Organohydrogenchloromonosilanes carrying one or more organic groups R, one or more hydrogen substituents and one or more chlorine substituents are valuable building blocks in synthetic silicon chemistry due to their difunctional substitution.

[0214] The most preferred target compound (A) according to the embodiment is 、 and .

[0215] In one 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. Thus, the starting material (B) according to this embodiment comprises monosilanes, disilanes, polysilanes, and carbodisilanes having one or more groups R and at least one halo group X bonded to one or more Si atoms of the compound. In the method according to this embodiment, any type of organosilane having one or more Si-X bonds, including organohydrohalosilanes (B), can be further hydrogenated by contacting the silane compound (B) with a metal hydride.

[0216] According to this embodiment, the radicals R of the silane compound (B) are independently selected from optionally substituted, preferably unsubstituted, alkyl, aryl, alkenyl, alkynyl, alkaryl, aralkyl, aralkenyl, aralkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, cycloaralkyl, cycloaralkenyl, cycloaralkynyl, more preferably from alkyl, cycloalkyl, alkenyl and aryl, even further preferably from methyl, vinyl and phenyl, and most preferably R is methyl. Preferably, the compound (B) having at least one Si-X bond is an organoperchlorosilane, i.e. all substituents of the silane compound (B) other than organic radicals are chlorine substituents. Preferred monosilanes according to the embodiment have the general formula 、 and , preferably disilazane has the general formula 、 and , preferably polysilanes have the general formula 、 、 、 、 、 、 、 、 , and preferably carbodisilane has the general formula 、 、 、 、 、 、 、 and .

[0217] Preferred examples of the compound (B) having at least one Si-X bond according to an embodiment of the present invention are 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 and .

[0218] More preferably, compound (B) is an organoperchloromonosilane compound, and most preferably, compound (B) is selected from and ,in particular .

[0219] In an embodiment according to the present invention, the product (A) is selected from the group consisting of monosilanes of formula (I)

[0220] (I),

[0221] Wherein R is an organic group,

[0222] x=0 to 3, preferably 0, 1, 2 and 3,

[0223] y = 1 to 4, preferably 1 to 2, most preferably 1

[0224] z = 0 to 3, preferably 0, 1, 2 and 3, and

[0225] x+y+z=4.

[0226] The monosilane (A) of the embodiment may be a chlorosilane without any organic group R, i.e., x=0 in the general formula (I). The preferred halogenated monosilane according to the embodiment is 、 、 、 、 and ,in and More preferably, the monosilane (A) is an organosilane, wherein x is 1 to 3, even more preferably 1 or 2, and y is preferably 1 or 2. The preferred organosilane according to the embodiment is 、 and Preferably, the organic group R is selected from methyl, ethyl, phenyl and vinyl. The most preferred monosilane product (A) is 、 and .

[0227] In an embodiment according to the present invention, the product (A) is selected from the group consisting of monosilanes of formula (I)

[0228] (I),

[0229] Wherein R is an organic group,

[0230] x=1 to 3, preferably 1 to 2,

[0231] y=1 to 3, preferably 1 to 2,

[0232] z = 0 to 2, preferably 1 to 2, and

[0233] x+y+z=4.

[0234] According to an embodiment, the preferred organomonosilane is 、 and Preferably, the organic group R is selected from methyl, ethyl, phenyl and vinyl. The most preferred monosilane product (A) is 、 and .

[0235] In an embodiment according to the present invention, the compound (B) having at least one Si-X bond is selected from the group consisting of organochloromonosilanes of formula (II)

[0236] (II)

[0237] Wherein R is as defined above,

[0238] a=1 to 3,

[0239] b = 0 to 2,

[0240] c = 1 to 3, and

[0241] a+b+c=4.

[0242] Preferably a=1 or 2, and b=0, i.e. the starting material is a monosilane with one or two organic groups and only chlorine substituents. Further preferably, the organic group R is selected from methyl, ethyl, phenyl and vinyl. The most preferred monosilane starting material (B) is and .

[0243] In one embodiment according to the present invention, the organic group R is independently selected from an alkyl group, a cycloalkyl group or a phenyl group, preferably R represents a methyl group.

[0244] Preferably, all groups R in the organosilane (B) containing one or more Si-X bonds or the organosilane (A) containing one or more Si-H bonds are selected from the same type of group, said group being selected from alkyl, cycloalkyl or phenyl, more preferably from C1-C12 alkyl, C3-C8 cycloalkyl and phenyl, and most preferably from methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopentyl, cyclohexyl and phenyl. Most preferably, any R is methyl, and accordingly the most preferred organosilane (B) according to the embodiment is and , and accordingly the most preferred organosilane (A) according to the embodiment is 、 and .

[0245] In one embodiment according to the present invention, compound (A) is selected from 、 、 、 、 and , preferably, compound (A) is .

[0246] Methylhydromonosilanes, in particular methylhydromonosilanes, are particularly valuable reagents and there is therefore a high interest in providing such compounds in a sustainable and cost- and resource-efficient manner. According to this embodiment, methylhydromonosilane (A) is preferably provided by 、 、 and :Methylchlorosilane 、 and Respectively react with one or more metal hydrides (C) in the presence of one or more heterocyclic ionic liquids, preferably using CaH2 as the metal hydride, and further preferably using a heterocyclic ionic liquid selected from N-containing aromatic quaternary ammonium compounds.

[0247] In one embodiment according to the present invention, compound (B) is selected from 、 、 and , preferably compound (B) is .

[0248] Compound (B) according to this embodiment can be fully hydrogenated by reacting the silane with an excess of hydride ions from the metal hydride (C) in the presence of a heterocyclic ionic liquid without any additional activation means or reagents, resulting in the silane product (A) 、 and Preferably, the compound (B) according to the embodiment is reacted with a substoichiometric amount of hydride ions from the metal hydride (C), resulting in partial replacement of the Si-X bonds of the starting material. The most preferred product is 、 and The presence of heterocyclic ionic liquids allows such reactions to proceed in the absence of additional activation means or reagents and further reduces the starting material (B) and its perhydrogenated analogue, respectively 、 and The amount is such that the desired organohydrochlorosilane is favored by a balance via redistribution of chlorine and hydrogen atoms.

[0249] In one embodiment according to the present invention, 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, 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 binary metal hydrides, more preferably from alkali metal hydrides and alkaline earth metal hydrides, even more preferably from the group consisting of lithium hydride, sodium hydride, potassium hydride, magnesium hydride, and calcium hydride, even more preferably from calcium hydride and magnesium hydride, and most preferably the metal hydride (C) is calcium hydride.

[0250] Although the reaction of the silane compound with one or more Si-X bonds with the metal hydride often needs to be activated by activation means such as sonication, grinding or adding an activator, by contacting the metal hydride with the silane (B) in the presence of a heterocyclic ionic liquid, the compound (B) can be easily converted into the desired product (A). This makes it possible to use relatively low-cost hydrides NaH, KH, MgH2 and CaH2, in particular with CaH2 to carry out the reaction of the method. Since the form of the metal hydride (C) is not limited, it is preferred that the metal hydride is added to the reaction mixture as a micronized powder or as a slurry of such a powder according to an embodiment. The heterocyclic ionic liquid promotes the reaction by removing the passivation layer of the metal oxide and in particular the metal halide formed in the reaction with the halosilane from the surface of the metal hydride particles.

[0251] In another embodiment according to the present invention, the process is carried out in the absence of any metal hydride reagent (C) other than CaH2.

[0252] As mentioned above, calcium hydride is preferably used as the metal hydride (C) because it is readily available at low cost. In the presence of a heterocyclic ionic liquid, no additional metal hydride reagent (C) is required, which further improves the cost efficiency of the process for producing one or more silane compounds (A) having at least one Si-H bond.

[0253] In one embodiment according to the present invention, the molar ratio of hydride ions of the one or more metal hydrides in the reaction mixture relative to the halogen atoms, preferably chlorine atoms, of the one or more compounds (B) is in the range of about 0.01 to about 300, more preferably about 0.1 to about 10, even more preferably about 0.4 to about 6, and most preferably about 0.7 to about 3.

[0254] As previously described, the amount of metal hydride (C) relative to the halogen atoms that delivers the hydride ions to be added is determined by whether complete replacement of all Si-X bonds by Si-H bonds is desired and whether there is further consumption of hydride ions, for example by reactions of other compounds that do not fall under the definition of silane compound (B) in the reaction mixture.

[0255] In one embodiment according to the present invention, the heterocyclic ionic liquid is selected from N-heterocyclic ionic liquids and P-heterocyclic ionic liquids.

[0256] According to the present invention, N-heterocyclic ionic liquids and P-heterocyclic ionic liquids are heterocyclic ionic liquids as defined above, wherein the heterocycle of the ionic liquid compound is a P-heterocycle, i.e., a cyclic structure containing P atoms as ring members, or an N-heterocycle, i.e., a cyclic structure containing N atoms as ring members. The P-heterocycle or N-heterocycle may be present in the cation, anion, or both the cation and anion of the ionic liquid, respectively, but preferably the cation of the ionic liquid comprises a P-heterocycle or an N-heterocycle.

[0257] In one embodiment according to the present invention, the heterocyclic ionic liquid is selected from N-heterocyclic aromatic ionic liquids and P-heterocyclic aromatic ionic liquids.

[0258] According to this embodiment, the compound of the N- or P-heterocyclic ionic liquid comprises one or more aromatic moieties. Preferably, the aromatic structure of the N- or P-heterocyclic compound is a heterocyclic structure. Examples of N-heterocyclic aromatic ionic liquids according to embodiments are ionic liquids selected from imidazolium salts, pyridinium salts, and triazolium salts, and examples of P-heterocyclic aromatic ionic liquids according to embodiments are ionic liquids selected from phospholium salts and phosphonium salts.

[0259] In one embodiment according to the present invention, the heterocyclic ionic liquid is selected from N-heterocyclic quaternary ammonium ionic liquids and P-heterocyclic phosphonium ionic liquids.

[0260] The compounds of the N- or P-heterocyclic ionic liquids according to this embodiment contain one or more quaternary ammonium groups or phosphonium groups, respectively. Typically, the quaternary structure of the N- or P-heterocyclic compound is located in the heterocyclic structure, i.e. it is a quaternary N- or P-atom that is part of the ring structure. The N-heterocyclic quaternary ammonium ionic liquid can be selected, for example, from pyridinium salts, imidazolium salts, Triazolium salts, imidazolinium salts and pyrrolium salts, morpholinium salts, piperidinium salts, piperazinium salts and pyrrolidinium salts.

[0261] The preferred P-heterocyclic ionic liquid compound according to this embodiment is a phospholanium salt having the general structure

[0262]

[0263] where R 18 and R 19 independently selected from methyl, ethyl, butyl, hexyl and octyl residues, preferably R 18 is selected from methyl or butyl, and R 19 is selected from methyl, ethyl, butyl, hexyl and octyl residues, further preferably R 18 is selected from methyl or butyl, and R 19 Selected from methyl, ethyl or butyl, most preferably R 18 and R 19 are independently selected from methyl and butyl residues, and Z is preferably selected from chloride, bromide, acetate, trifluoroacetate, tetrafluoroborate, hexafluorophosphate or methanesulfonate anions, most preferably Z is chloride anion. Optionally, the P,P-substituted phosphacyclopentane salts may carry one or more additional C1-C12 alkyl substituents on one or more ring carbon atoms, preferably they additionally carry one additional methyl, ethyl, butyl, hexyl and octyl residue on a 2-C, 3-C or 4-C ring atom, more preferably a methyl, ethyl or butyl residue.

[0264] Particularly preferred The substituted phospholanium compound is Dimethyl-phospholanium chloride, 1-ethyl-1-methyl-phospholanium chloride, 1-butyl-1-methyl-phospholanium chloride, 1-hexyl-1-methyl-phospholanium chloride, 1-octyl-1-methyl-phospholanium chloride, 1-butyl-1-ethyl-phospholanium chloride, Dibutyl-phospharolium chloride, 1-hexyl-1-butyl-phospharolium chloride, and 1-octyl-1-butyl-phospharolium chloride.

[0265] Another preferred class of P-heterocyclic ionic liquid compounds according to this embodiment is phosphonium salts having the general structure

[0266] ,

[0267] where R 20 and R 21 independently selected from methyl, ethyl, butyl, hexyl and octyl residues, preferably R 20 is selected from methyl or butyl, and R 21 is selected from methyl, ethyl, butyl, hexyl and octyl residues, further preferably R 20 is selected from methyl or butyl, and R 21 Selected from methyl, ethyl or butyl, 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 methanesulfonate anions, most preferably Z is chloride anion. Optionally, the P,P-substituted phosphonium salts may carry one or more additional C1-C12 alkyl substituents on one or more ring carbon atoms, preferably they additionally carry one additional methyl, ethyl, butyl, hexyl and octyl residue on a 2-C, 3-C or 4-C ring atom, more preferably a methyl, ethyl or butyl residue. Particularly preferred P,P-substituted phosphonium compounds are 1,1-dimethyl-phosphonium chloride, 1-ethyl-1-methyl-phosphonium chloride, 1-butyl-1-methyl-phosphonium chloride, 1-hexyl-1-methyl-phosphonium chloride, 1-octyl-1-methyl-phosphonium chloride, 1-butyl-1-ethyl-phosphonium chloride, 1,1-dibutyl-phosphonium chloride, 1-hexyl-1-butyl-phosphonium chloride and 1-octyl-1-butyl-phosphonium chloride.

[0268] In one embodiment according to the present invention, the heterocyclic ionic liquid is selected from N-heterocyclic aromatic quaternary ammonium ionic liquids and P-heterocyclic aromatic quaternary phosphonium ionic liquids.

[0269] In one embodiment of the present invention, the heterocyclic ionic liquid is selected from the group consisting of pyridinium salts, imidazolium salts, The group of aromatic heterocyclic quaternary ammonium salts of triazolium salts, imidazolinium salts, pyrrolidinium salts, the group of non-aromatic heterocyclic quaternary ammonium salts comprising morpholinium salts, piperidinium salts, piperazinium salts and pyrrolidinium salts, and the group of aromatic heterocyclic quaternary phosphonium salts comprising phosphonium salts. Preferably, the counter anion in the ionic liquid based on aromatic heterocyclic quaternary ammonium salts, the ionic liquid based on non-aromatic heterocyclic quaternary ammonium salts or the ionic liquid based on aromatic heterocyclic quaternary phosphonium salts as described above is selected from chloride, bromide, acetate, trifluoroacetate, tetrafluoroborate, hexafluorophosphate or methanesulfonate anions, most preferably selected from chloride, bromide and tetrafluoroborate.

[0270] According to the embodiment, preferably The triazolium salt has the following general structure Replaced Triazolium salts

[0271] ,

[0272] where R 6 and R 7 independently selected from methyl, ethyl, butyl, hexyl and octyl residues, preferably R 6 is selected from methyl or butyl, and R 7 is selected from methyl, ethyl, butyl, hexyl and octyl residues, further preferably R 6 is selected from methyl or butyl, and R 7 Selected from methyl, ethyl or butyl, most preferably R 6 and R 7 are independently selected from methyl and butyl residues, and Z is preferably selected from chloride, bromide, acetate, trifluoroacetate, tetrafluoroborate, hexafluorophosphate or methanesulfonate anions, most preferably Z is chloride anion. Optionally, 1,3-substituted The triazolium salts may carry one or more additional C1-C12-alkyl substituents on one or more ring carbon atoms, preferably they additionally carry one additional methyl, ethyl, butyl, hexyl or octyl residue on the 4-C ring atom, more preferably a methyl, ethyl or butyl residue. 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-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 which carry further substituents at 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, 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-Bu-triazolium chloride, 1-butyl-3-ethyl-4-butyl-1,2,3-triazolium chloride, 1-butyl-3-butyl-4-butyl-1,2,3-triazolium chloride.

[0273] According to an embodiment, the preferred pyrrolium salt is an N,N-alkylpyrrolium salt of the following general structure:

[0274] ,

[0275] where R 4 and R 5 independently selected from methyl, ethyl, butyl, hexyl and octyl residues, preferably R 4 is selected from methyl or butyl, and R 5 is selected from methyl, ethyl, butyl, hexyl and octyl residues, further preferably R 4 is selected from methyl or butyl, and R 5 Selected from methyl, ethyl or butyl, 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 methanesulfonate anions, most preferably Z is chloride anion. Optionally, the N,N-substituted pyrrolium salts may carry one or more additional C1-C12 alkyl substituents on one or more ring carbon atoms, preferably they additionally carry one additional methyl, ethyl, butyl, hexyl and octyl residue on a 2-C or 3-C ring atom, more preferably a methyl, ethyl or butyl residue. Particularly 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 which carry further substituents on the 2-C ring atom 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-1,2-dimethyl-pyrrolium chloride. 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 which carry additional substituents on the 3-C ring atom 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-1,3-dimethyl-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.

[0276] According to an embodiment, the preferred N,N-morpholinium salt is an N,N-alkylmorpholinium salt of the following general structure:

[0277] ,

[0278] where R 8 and R 9 independently selected from methyl, ethyl, butyl, hexyl and octyl residues, preferably R 8 is selected from methyl or butyl, and R 9 is selected from methyl, ethyl, butyl, hexyl and octyl residues, more preferably R 8 is selected from methyl or butyl, and R 9 Selected from methyl, ethyl or butyl, 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 methanesulfonate anions, most preferably Z is chloride anion. Optionally, the N,N-substituted morpholinium salts may carry one or more additional C1-C12 alkyl substituents on one or more ring carbon atoms, preferably they additionally carry one additional methyl, ethyl, butyl, hexyl and octyl residue on a 2-C or 3-C ring atom, more preferably a methyl, ethyl or butyl residue. Particularly 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.

[0279] According to the embodiment, the preferred N,N-piperidinium salt is an N,N-alkylpiperidinium salt of the following general structure:

[0280] ,

[0281] where R 10 and R 11 independently selected from methyl, ethyl, butyl, hexyl and octyl residues, preferably R 10 is selected from methyl or butyl, and R 11 is selected from methyl, ethyl, butyl, hexyl and octyl residues, more preferably R 10 is selected from methyl or butyl, and R 11 Selected from methyl, ethyl or butyl, most preferably R 10 and R 11 are independently selected from methyl and butyl residues, and Z is preferably selected from chloride, bromide, acetate, trifluoroacetate, tetrafluoroborate, hexafluorophosphate or methanesulfonate anions, most preferably Z is a chloride anion.

[0282] Optionally, the N,N-substituted piperidinium salts may carry one or more additional C1-C12-alkyl substituents on one or more ring carbon atoms, preferably they additionally carry one additional methyl, ethyl, butyl, hexyl and octyl residue on a 2-C, 3-C or 4-C ring atom, more preferably a methyl, ethyl or butyl residue. Particularly 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.

[0283] The preferred N,N-pyrrolidinium salt according to the embodiment is an N,N-alkylpyrrolidinium salt of the following general structure

[0284] ,

[0285] where R 12 and R 13 independently selected from methyl, ethyl, butyl, hexyl and octyl residues, preferably R 12 is selected from methyl or butyl, and R 13 is selected from methyl, ethyl, butyl, hexyl and octyl residues, more preferably R 12 is selected from methyl or butyl, and R 13 Selected from methyl, ethyl or butyl, 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 methanesulfonate anions, most preferably Z is chloride anion. Optionally, the N,N-substituted pyrrolidinium salts may carry one or more additional C1-C12 alkyl substituents on one or more ring carbon atoms, preferably they additionally carry one additional methyl, ethyl, butyl, hexyl and octyl residue on a 2-C, 3-C or 4-C ring atom, more preferably a methyl, ethyl or butyl residue. Particularly 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.

[0286] The preferred piperazinium monosalt according to the embodiment is an N,N,N'-alkylpiperazinium monosalt of the following general structure

[0287] ,

[0288] where R 14 、R 15 and R 16 independently selected from methyl, ethyl, butyl, hexyl and octyl residues, preferably R 15 is selected from methyl or butyl, and R 14 and R 16 is selected from methyl, ethyl, butyl, hexyl and octyl residues, more preferably R 15 is selected from methyl or butyl, and R 14 and R 16 Selected from methyl, ethyl or butyl, most preferably R 14 、R 15 and R 16 are independently selected from methyl and butyl residues, and Z is preferably selected from chloride, bromide, acetate, trifluoroacetate, tetrafluoroborate, hexafluorophosphate or methanesulfonate anions, most preferably Z is chloride anion. Optionally, the N,N,N'-substituted piperazinium monosalt may carry one or more additional C1-C12 alkyl substituents on one or more ring carbon atoms, preferably they carry one additional methyl, ethyl, butyl, hexyl and octyl residue on a 2-C, 3-C, 5-C or 6-C ring atom, more preferably a methyl, ethyl or butyl residue. Particularly 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- 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-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.

[0289] According to this embodiment, the preferred piperazinium disalt is an N,N,N',N'-alkylpiperazinium disalt of the following general structure:

[0290] ,

[0291] where R 14 、R 15 、R 16 and R 17 independently selected from methyl, ethyl, butyl, hexyl and octyl residues, preferably R 15 and R 17 is selected from methyl or butyl, and R 14 and R 16 is selected from methyl, ethyl, butyl, hexyl and octyl residues, more preferably R 15 and R 17 is selected from methyl or butyl, and R 14 and R 16 Selected from methyl, ethyl or butyl, most preferably R 14 、R 15 、R 16 and R 17In the embodiment of the present invention, Z is independently selected from methyl and butyl residues, and Z is preferably selected from chlorine, bromine, acetate, trifluoroacetate, tetrafluoroborate, hexafluorophosphate or methanesulfonate anions, most preferably Z is a chloride anion. In the case of the structure of the piperazinium disalt shown above, the two Z-anions together can also represent a divalent anion, such as a sulfate divalent anion, an oxalate divalent anion, a malonate divalent anion, a succinate divalent anion, a maleate divalent anion, a fumarate divalent anion, a tartrate divalent anion or a phthalate divalent anion. Optionally, the N,N,N',N'-substituted piperazinium disalt can carry one or more additional C1-C12 alkyl substituents on one or more ring carbon atoms, preferably they carry an additional methyl, ethyl, butyl, hexyl and octyl residue on a 2-C, 3-C, 5-C or 6-C ring atom, more preferably a methyl, ethyl or butyl residue.Particularly preferred N,N,N',N'-substituted piperazinium disalt 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-4,4-dimethyl-piperazinium dichloride, and 1-octyl-1-butyl-4,4-dimethyl-piperazinium dichloride. ,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, 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.

[0292] 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 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 1,3-alkyl-substituted imidazolium salts, in particular 1,3-alkyl-substituted imidazolium salts having a C1-C12 alkyl substituent in the 1-position and a methyl group in the 3-position, further 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 EthylMIMCl and HexMIMCl. Preferably, the counter anion in the imidazolium-based ionic liquid or pyridinium-based ionic liquid is selected from chloride, bromide, acetate, trifluoroacetate, tetrafluoroborate, hexafluorophosphate or methanesulfonate anions, most preferably chloride, bromide and tetrafluoroborate.

[0293] According to an embodiment, the 1-substituted pyridinium salt is preferably a compound of the following general structure

[0294]

[0295] where R 3 independently selected from methyl, ethyl, butyl, hexyl and octyl residues, preferably R 3 is selected from methyl or butyl, and Z is preferably selected from chloride, bromide, acetate, trifluoroacetate, tetrafluoroborate, hexafluorophosphate or methanesulfonate anions, most preferably Z is chloride anion.

[0296] Optionally, the N,N-substituted pyridinium salts may carry one or more additional C1-C12-alkyl substituents on one or more ring carbon atoms, preferably they additionally carry one additional methyl, ethyl, butyl, hexyl and octyl residue on a 2-C, 3-C or 4-C ring atom, more preferably a methyl, ethyl or butyl residue.

[0297] Particularly 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.

[0298] Particularly preferred N-substituted pyridinium compounds which carry additional substituents at the 2-C ring atom 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, 1-octyl-2-butyl-pyridinium chloride, and preferred N-substituted pyridinium compounds which carry additional substituents at the 3-C ring atom are 1,3-dimethyl-pyridinium chloride, 1-ethyl-3-methyl-pyridinium chloride, 1-butyl-3-methyl-pyridinium chloride, 1- Hexyl-3-methyl-pyridinium chloride, 1-octyl-3-methyl-pyridinium chloride, 1-butyl-3-butyl-pyridinium chloride, 1-hexyl-3-butyl-pyridinium chloride, and 1-octyl-3-butyl-pyridinium chloride, and the preferred N-substituted pyridinium chloride with an additional substituent at the 4-C ring atom is 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.

[0299] According to this embodiment, the 1,3-substituted imidazolium salt is preferably a compound of the following general structure:

[0300]

[0301] where R 1 and R 2 independently selected from methyl, ethyl, butyl, hexyl and octyl residues, preferably R 1 is selected from methyl or butyl, and R 2 is selected from methyl, ethyl, butyl, hexyl and octyl residues, further preferably R 1 is selected from methyl or butyl, and R 2 Selected from methyl, ethyl or butyl, 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 methanesulfonate anions, most preferably Z is chloride anion. Optionally, the 1,3-substituted imidazolium salts may carry one or more additional C1-C12 alkyl substituents on one or more ring carbon atoms, preferably they additionally carry one additional methyl, ethyl, butyl, hexyl and octyl residue on a 2-C ring atom or a 4-C ring atom, more preferably a methyl, ethyl or butyl residue. 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 which carry a further substituent at the C atom of the 2-C ring are 1,2,3-trimethylimidazolium chloride, 1-ethyl-2,3-dimethylimidazolium chloride, 1-butyl-2,3-dimethylimidazolium chloride, 1-butyl-2-methyl-3-ethylimidazolium chloride, 1,3-dibutyl-2-methylimidazolium chloride, 1,3-dimethyl-2-butylimidazolium chloride, 1-ethyl-2-butyl-3-methylimidazolium chloride, 1,2-dibutyl-3-methylimidazolium chloride, 1,2-dibutyl-3-ethylimidazolium chloride, 1,2,3-tributylimidazolium chloride. Particularly preferred 1,3-substituted imidazolium compounds which carry a further substituent at the C atom of the 4-C ring are 1,3,4-trimethylimidazolium chloride, 1-ethyl-3,4-dimethylimidazolium chloride, 1-butyl-3,4-dimethylimidazolium chloride, 1-butyl-3-ethyl-4-methylimidazolium chloride, 1,3-dibutyl-4-methylimidazolium chloride, 1,3-dimethyl-4-butylimidazolium chloride, 1-ethyl-3-methyl-4-butylimidazolium chloride, 1,4-dibutyl-3-methylimidazolium chloride, 1,4-dibutyl-3-ethylimidazolium chloride, 1,3,4-tributylimidazolium chloride. The most preferred ionic liquid compounds according to an embodiment are 1-ethyl-3-methylimidazolium chloride (EthylMIMCl) and 1-hexyl-3-methylimidazolium chloride (HexMIMCl).

[0302] In one embodiment according to the present invention, the melting point of the ionic liquid is below about 150°C, preferably below about 100°C, more preferably below about 80°C, still more preferably below about 60°C, even more preferably below about 40°C, and most preferably below about 30°C.

[0303] Since heterocyclic ionic liquids are defined as being liquid at the temperature at which the process is carried out, the heterocyclic liquid according to this embodiment has a melting point below about 150° C., which is generally preferred according to embodiments of the present invention, as processes according to embodiments of the present invention are preferably carried out at temperatures below about 150° C.

[0304] In one embodiment according to the present invention, 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 about 0.1 mol% to about 1500 mol%, preferably about 0.2 mol% to about 1000 mol%, more preferably about 0.4 mol% to about 600 mol%, even more preferably about 0.7 mol% to about 300 mol%, further preferably about 0.7 mol% to about 100 mol%, even further preferably about 2 mol% to about 100 mol%, and most preferably about 5 mol% to about 100 mol%.

[0305] Preferably, the starting materials for the reaction contain no further components besides the silane compound(s) (B), the metal hydride(s) (C) and the heterocyclic ionic liquid(s) in the amounts described above relative to the compound(s) (B).

[0306] In one embodiment according to the present invention, the process is carried out in the absence of an ether solvent, preferably in the absence of an ether solvent and a linear or cyclic aliphatic hydrocarbon solvent, more preferably in the absence of an ether solvent and a linear or cyclic aliphatic hydrocarbon solvent and an aromatic hydrocarbon solvent, most preferably in the absence of any other solvent than one or more ionic liquids.

[0307] There may be a variety of reasons for using a solvent in a chemical process, for example, the purpose of providing a reaction mixture in which the starting material is uniformly dissolved, the purpose of controlling conversion and the thermal effects associated with the exothermic reaction, and many more reasons well known to those skilled in the art. However, there may also be many disadvantages associated with the need to use a solvent, such as the toxic properties of many organic solvents, the cost of providing the solvent, and the problem of removing the solvent from the desired product. In the case of ether solvents, there is an additional risk of peroxide formation, which may make the use of such solvents dangerous, particularly on an industrial scale. Therefore, since it is not necessary to use an additional solvent and in order to avoid the above-mentioned problems, the method according to this embodiment is carried out in the absence of an ether solvent, and most preferably in the absence of any additional solvent other than one or more heterocyclic ionic liquids. Although the method according to other embodiments of the present invention generally does not exclude the presence of any solvent in the reaction mixture, it is generally preferred according to embodiments of the present invention that no other solvent is present except the heterocyclic ionic liquid required for the method.

[0308] In one embodiment according to the present invention, the method is carried out in the absence of an acyclic quaternary ammonium salt and an acyclic quaternary phosphonium salt.

[0309] Acyclic quaternary ammonium salts and acyclic quaternary phosphonium salts are known in the art as catalysts for the redistribution reaction of silanes, which are used in the presence of organic solvents, particularly ether compounds. In the process of the present invention, the presence of heterocyclic ionic liquids not only enables the use of otherwise less reactive metal hydrides to reduce halosilanes, but also makes the presence of additional redistribution catalysts and solvents obsolete, thereby reducing process complexity and improving process performance and efficiency.

[0310] In one embodiment according to the present invention, the reaction is carried out at a temperature 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 in the range of 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 within the reaction vessel in which the reaction is carried out.

[0311] In one embodiment according to the present invention, the reaction is carried out at a pressure in the range of about 0.1 to about 20 bar, preferably about 0.3 to about 20 bar, more preferably about 1 to about 20 bar, even more preferably about 1 to about 10 bar, and most preferably in the range of about 1 to about 5 bar. As defined herein, the indicated pressure ranges refer to the pressure measured in the reaction vessel used when carrying out the method of the embodiment of the present invention.

[0312] In one embodiment according to the present invention, the process is carried out under inert conditions. As defined herein, the term "under inert conditions" means that the process is carried out partially or completely with the exclusion of ambient air, in particular moisture and oxygen. To exclude ambient air from the reaction mixture and the reaction product, a closed reaction vessel, reduced pressure and / or an inert gas, in particular nitrogen or argon, or a combination of such measures may be used.

[0313] In one embodiment according to the present invention, the method is carried out continuously or discontinuously, for example in batches. Preferably, the method of the embodiment is carried out in a batch mode, for example in a batch reactor made of steel, stainless steel, glass-lined steel, glass, or another suitable alloy different from steel.

[0314] In one embodiment according to the invention, the process is carried out in the absence of grinding or sonicating the reaction mixture.

[0315] In many cases, the reduction of halosilanes by metal hydrides requires activation of the metal hydride, which is typically achieved by adding an activator such as aluminum chloride (AlCl ), adding a solvent that promotes such a reaction such as an ether compound, by mechanical activation of the metal hydride, or a combination of these means. As means of mechanical activation, grinding and sonication have been found to be particularly effective. "Grinding" in this article generally refers to any treatment intended to reduce the size of a solid material by mechanical force, and particularly includes carrying out the reaction in a ball mill.

[0316] The term "sonication" as defined herein is applicable to any process wherein sound energy is applied to the reaction mixture, particularly ultrasonic frequencies, i.e., ultrasonication. When ultrasound is applied to a medium, sound waves are converted into mechanical energy. Grinding and ultrasonication both promote the reaction of metal hydrides and halosilanes by mechanically removing the metal halide, which forms a passivation layer on the surface of the metal hydride particles subjected to the reaction with the halosilanes, thereby allowing the reaction to continue. By decomposing the metal hydride into smaller particles and thus increasing the total surface area of the metal hydride particles, ultrasonication and particularly grinding further promote the reaction of metal hydrides and halosilanes. However, both grinding and ultrasonication require non-standard equipment and therefore increase the complexity of the reaction. When halosilanes, particularly organochloromonosilanes, are subjected to reaction with metal hydrides, preferably alkali metal hydrides and alkaline earth metal hydrides, particularly CaH2, the presence of heterocyclic ionic liquids allows the desired reduction product to be obtained in the absence of additional chemical or mechanical activation, particularly in the absence of grinding and ultrasonication. This allows saving costs and effort when carrying out the reaction.Thus, the process of an embodiment of the present invention is carried out in the absence of grinding or sonicating the reaction mixture according to this embodiment, which is generally preferred for processes according to embodiments of the present invention.

[0317] In one embodiment according to the invention, the process is carried out without supply of hydrogen chloride and / or in the absence of a metal catalyst, preferably in the absence of aluminum chloride or a palladium catalyst.

[0318] The presence of hydrogen chloride or a metal catalyst, particularly AlCl or a palladium catalyst, is not required for the successful implementation of the process according to embodiments of the present invention. AlCl has been used in conventional processes to enable the reduction of MeSiCl by MgH; however, under the conditions of the process according to embodiments of the present invention, such activation is not required. The presence of AlCl further induces undesirable redistribution of the organic groups of the silane compounds (A) and (B) present in the reaction mixture.

[0319] The presence of AlCl also presents technical problems, since it is difficult to separate it from the products formed due to its high solubility in chlorosilanes and its low sublimation temperature. In this embodiment, the process is therefore carried out without supplying hydrogen chloride and / or in the absence of a metal catalyst, in particular a palladium catalyst or AlCl, which is generally preferred according to the invention and for all its embodiments.

[0320] In an embodiment according to the invention, the silane compound (A) having at least one formed Si—H bond, preferably Me 2 SiHCl, is separated from the reaction mixture by distillation and / or condensation.

[0321] The term "distillation" as defined herein relates to any method for separating components or substances from at least partially liquid mixtures by selective evaporation and condensation. Distillation can result in a virtually complete separation of the components of the mixture, thereby resulting in the isolation of nearly pure compounds, or it can be a partial separation that increases the concentration of selected components of the mixture in the distillate when compared to the mixture subjected to distillation. Preferably, the distillation method that can constitute the separation step for isolating 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 type of distillation known to those skilled in the art. Also preferably, the step of separating the desired silane compound (A) having at least one Si-H bond according to an embodiment of the present invention can include one or more batch distillation steps, or can include a continuous distillation process. Further preferably, the term "condensation" can include separating or enriching one or more silane compounds (A) having at least one Si-H bond from a reaction mixture by evaporation from a reaction vessel and condensation into a liquid and / or solid in a refrigerated container, which can then be recovered (recovered) by distillation or by dissolving in a solvent.

[0322] In one embodiment of the present invention, the feedstock subjected to the process contains about 75 weight-% or more of one or more compounds (B), preferably about 85 weight-% or more of one or more compounds (B), more preferably about 90 weight-% or more of one or more compounds (B), and most preferably about 95 weight-% or more of one or more compounds (B).

[0323] Unless otherwise indicated, the term "starting material", for example as "silane starting material (B)", refers to all compounds subjected to the reaction according to the process of the present invention, except for the metal hydride (C) and the heterocyclic ionic liquid. Thus, the amount of one or more compounds (B) given in wt% refers to the ratio of the compounds falling under the definition of silane compound (B) to the total amount of compounds falling under (B) and other additives, solvents and impurities (excluding the metal hydride (C) and the heterocyclic ionic liquid). Thus, according to an embodiment, the amount of additional additives, such as solvents, and impurities is less than about 25 wt%, preferably less than about 15 wt%, more preferably less than about 10 wt%, and most preferably less than about 5 wt%.

[0324] In one embodiment according to the present 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), most preferably about 95 wt-% or more of Me2SiCl2.

[0325] The amounts given in wt. % relate to the mass of organomonochlorosilane (B) relative to the total amount of silane starting material having one or more Si—X bonds (B) subjected to the process (excluding one or more metal hydrides (C) and heterocyclic ionic liquids).

[0326] Other solvents besides the ionic liquid, i.e., organic compounds that are inert under the reaction conditions and liquid at the reaction temperature, may generally be present but are considered unnecessary. In addition, the starting material may contain compounds that are impurities from previous production of the organochlorosilane. Although the presence of such impurities and solvents is not necessarily detrimental to the performance of the process, it is considered preferable that the amount of organochlorosilane (B) in the starting material is as high as possible, considering the reaction control, the necessity of adding excess metal hydride to compensate for the consumption of hydride in undesirable reactions of impurities, and the ease of purification of the desired product.

[0327] In one embodiment according to the present invention, compound (A) is Me2SiHCl, compound (B) is Me2SiCl2, and the metal hydride is CaH2.

[0328] In this embodiment of the invention, heterocyclic ionic liquids are particularly important as redistribution catalysts in order to shift the ratio of the reduction products Me2SiHCl and Me2SiH2 toward the target product M2SiHCl. The starting material Me2SiCl2 can be subjected to the method as a substantially pure compound or as a component of a mixture of compounds. For example, the compound can be subjected to the method according to the embodiment in the form of a crude product obtained by the Direct Process or a fraction obtained by purifying Me2SiCl2 produced by the Direct Process (e.g., a so-called Direct Process Residue (DPR) containing higher boiling point by-products such as methylchlorodisilanes and methylchlorooligosilanes). Preferably, the molar ratio of CaH2 to Me2SiCl2 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, unless the starting material contains, in addition to Me2SiCl2, a large amount of other compounds that consume hydride ions. As defined herein, such a substantial amount of additional compound is any amount greater than about 2 wt % based on the mass of the starting material containing Me2SiCl2.

[0329] In one embodiment according to the present invention, compound (A) is MeSiH2Cl or MeSiHCl2, compound (B) is MeSiCl3, and the metal hydride is CaH2.

[0330] Starting from MeSiCl or a mixture of compounds containing MeSiCl, both compounds MeSiH2Cl and MeSiHCl2 can be obtained, wherein the ratio of monohydrogenated and dihydrogenated products can be adjusted by the amount of CaH2 added to the reaction mixture. The use of CaH2 as a hydride source makes the method according to this embodiment particularly cost-effective. In this embodiment of the invention, heterocyclic ionic liquids are particularly important as redistribution catalysts in order 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 method are more prone to further hydrogenation by hydride ions than the starting material MeSiCl3, and therefore, in the absence of redistribution, an undesirable product distribution with a major amount of MeSiH3 is obtained. Preferably, the molar ratio of CaH2 to MeSiCl3 is 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, unless the starting material contains a large amount of additional compounds other than Me2SiCl2 that consume hydride ions. When the desired major product of the process of an embodiment is MeSiHCl2, it is preferred that the molar ratio of CaH2 to MeSiCl3 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. When the desired major product of the process is MeSiH2Cl, it is preferred that the molar ratio of CaH2 to MeSiCl3 is 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.

[0331] In one embodiment according to the invention, the method comprises breaking one or more Si-Si bonds of one or more disilane or polysilane compounds (B) and / or one or more Si-C bonds of one or more carbodisilane compounds (B).

[0332] By breaking one or more Si-Si bonds, monosilanes can be obtained from disilane, polysilane or carbodisilane starting materials (B). In particular, organohalogenated monosilanes can be obtained starting from organohalogenated disilanes and organohalogenated polysilanes. In the process of an embodiment of the present invention, the breaking of one or more Si-Si bonds allows the monosilane compound (A) to be obtained from the disilane and polysilane starting materials (B), in particular organomonosilanes from organodisilanes and organopolysilanes, preferably organochloromonosilanes from organochlorodisilanes and organochloropolysilanes. During the process of this embodiment comprising the breaking of disilanes and / or polysilanes, the conversion of one or more Si-X moieties of compound (B) into Si-H moieties can be carried out before, during or after the breaking of one or more Si-Si bonds and can be carried out by a reduction reaction with one or more metal hydrides (C) or by a redistribution reaction with a monosilane or a di-, poly- or carbodisilane having at least one Si-H bond. This also applies analogously to the cleavage of one or more Si-C bonds in the carbodisilane (B). Thus, the method according to this embodiment provides chlorohydromonosilanes starting from chlorodisilanes, chlorohydrodisilanes, chloropolysilanes, and chlorohydropolysilanes, in particular organohydromonosilanes starting from organochlorodisilanes, organochlorohydrodisilanes, organochloropolysilanes, and organochlorohydropolysilanes. According to this embodiment, preferably, the organochlorohydromonosilane is produced starting from an organochlorodisilane and / or an organochloropolysilane, and more preferably, the monosilane (A) selected from Me2SiHCl, MeSiHCl2, and MeSiH2Cl is obtained starting from methylchlorodisilane and / or methylchloropolysilane (i.e., a disilane and / or polysilane bearing only chlorine and methyl substituents). Therefore, the cleavage of the Si-Si bonds of disilanes, oligosilanes or polysilanes or of the Si-C bonds in carbodisilanes preferably takes place simultaneously with the reduction reaction and redistribution reaction involving the conversion of the silane compound (B) having at least one Si-Cl bond into a compound (A) having at least one Si-H bond, for example in the same reaction step and / or in the same reaction vessel.

[0333] According to an embodiment of the present invention, it is preferred that the heterocyclic ionic liquid used in the process acts as a solvent, a reaction promoter, a redistribution catalyst and a cleavage catalyst at the same time. At the same time, an additional cleavage catalyst, such as

[0334] - a quaternary Group 15 onium compound R4QX, wherein each R is independently hydrogen or an organic group, Q is nitrogen, phosphorus, arsenic, antimony or bismuth, and X is a halogen selected from F, Cl, Br and I,

[0335] - heterocyclic amines,

[0336] - Heterocyclic ammonium halides,

[0337] - a mixture of R3P and RX, wherein R is as defined above and X is as defined above,

[0338] - alkali metal halides,

[0339] - alkaline earth metal halides,

[0340] - an alkali metal hydride or an alkaline earth metal hydride, optionally

[0341] In the presence of hydrogen chloride (HCl),

[0342] In the processes applicable to the aforementioned embodiments, it is preferred that such an additional cleavage catalyst is not present in the reaction mixture, as it makes the process less cost-effective and more complicated with respect to the formation of by-products and purification of the desired product.

[0343] In one embodiment according to the present invention, compound (A) is selected from Me2SiHCl, MeSiH2Cl and MeSiHCl2, and compound (B) is selected from methylchlorodisilane and methylchloropolysilane, preferably methylchlorodisilane, and wherein the metal hydride is preferably CaH2 or MgH2.

[0344] As defined herein, the term "methylchlorodisilanes" includes the compounds MeSi2Cl5, Me2Si2Cl4, Me3Si2Cl3, Me4Si2Cl2 and Me5SiCl, wherein the formula MeSi2Cl5 represents the structure MeCl2Si-SiCl3, the formula Me2Si2Cl4 represents the structures Me2ClSi-SiCl3 and MeCl2Si-SiCl2Me, the formula Me3Si2Cl3 represents the structures Me3Si-SiCl3 and Me2ClSi-SiCl2Me, the formula Me4Si2Cl2 represents the structures MeCl2Si-SiMe3 and Me2ClSi-SiClMe2, and the formula Me5Si2Cl represents the structure Me2ClSi-SiMe3. Wherein, according to this embodiment, it is preferred that each Si atom carries one or more methyl groups and one or more chlorine groups. As defined herein, the term "methylchloropolysilane" includes any type of silane having three or more silicon atoms bonded to each other in a linear manner, wherein the additional substituents of the silicon atoms are selected only from methyl groups and chlorine. Wherein, according to this embodiment, preferably, each Si atom carries one or more methyl groups and one or more chlorine groups. As described in the previous embodiment, generally, the method comprising the cleavage of the Si-Si bond allows the production of the desired monosilane compound (A) Me2SiHCl, MeSiH2Cl and MeSiHCl2 starting from compound (B) (which is methylchlorodisilane and methylchloropolysilane). Such compounds are produced in large quantities as by-products of the direct method for producing methylchlorosilane. In addition, with respect to this embodiment, the product mixture of the direct method can be directly subjected to the method of the embodiment of the present invention without pre-separating the main product dimethyldichlorosilane, as well as disilane, oligosilane and polysilane by-products, which are generally represented as high-boiling residues according to their boiling point characteristics in the separation method. The main product Me2SiCl2 and by-products MeSiCl3, methylchlorodisilane and methylchlorodisilane contained in the direct method product mixture can all be converted into the target compound (A) selected from Me2SiHCl, MeSiH2Cl and MeSiHCl2 by the cleavage of the Si-Si bond. From an economic point of view, in the method according to this embodiment, it is preferred to use the low-cost reducing agent MgH2 or CaH2, even more preferably CaH2.

[0345] In a particularly preferred embodiment according to the present invention, compound (A) selected from Me2SiHCl, MeSiH2Cl and MeSiHCl2 is obtained by reacting methyldichlorosilane (preferably selected from Me2Si2Cl4, Me3Si2Cl3 and Me4Si2Cl2) constituting compound (B) with CaH2 in the presence of a heterocyclic ionic liquid, preferably selected from N-heterocyclic ionic liquids, even more preferably from the group of 1-substituted imidazolium salts, even further preferably from 1,3-alkyl-substituted imidazolium salts, in particular with a C1-C12 alkyl substituent in the 1-position and a methyl group in the 3-position, most preferably from 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 counter anion in the ionic liquid based on imidazolium is selected from chlorine, bromine, acetate, trifluoroacetate, tetrafluoroborate, hexafluorophosphate or methylsulfate anion, most preferably selected from chlorine, bromine and tetrafluoroborate. Further preferably, no other cleavage agent, redistribution catalyst or activator is added to the reaction mixture. Methylchlorodisilane (B) can be used as a substantially pure single compound or a mixture of multiple methylchlorodisilanes (B) or as a mixture of one or more methylchlorosilanes (methylchlorosisilane) and other silane compounds (for example, a high boiling point residue obtained when carrying out a direct process for the preparation of methylchlorosilane, and / or another compound not falling under the definition of compound (B)) subjected to the reaction according to the method of this embodiment. The process is considered useful when the material containing the one or more compounds (B) subjected to the process contains about 5 wt-% or more methylchlorodisilane, more preferably about 20 wt-% or more, even more preferably about 50 wt-% or more, and still more preferably more than about 75 wt-%, and most preferably about 95 wt-% or more methylchlorodisilane.

[0346] According to the present invention, the compound is considered to be substantially pure if it has less than about 2% by weight of impurities, based on the total weight of the compound and the impurities contained. Preferably, the presence of one or more heterocyclic liquids enables the cleavage of the Si-Si bonds required to convert the compound (B) selected from methylchlorodisilanes or methylchloropolysilanes into methylmonosilanes in the absence of an additional cleavage catalyst, as described with respect to the previous embodiment.

[0347] In a further aspect, the invention relates to a composition comprising:

[0348] - one or more silane compounds (A') having at least one Si-H bond and at least one Si-X bond,

[0349] Wherein X is a halogen atom,

[0350] - one or more metal halides (C'),

[0351] - one or more heterocyclic ionic liquids,

[0352] - Optionally one or more silane compounds (A") having at least two Si-H bonds and no Si-X bonds. Preferably, compound (A") is a silane compound obtained from the corresponding silane compound (A') by replacing any Si-X bonds by Si-H bonds.

[0353] Such a composition is obtainable by the process according to the invention as described in detail above.

[0354] Silane compound (A')

[0355] The term "one or more compounds (A') having at least one Si-H bond and at least one Si-X bond" as defined herein includes any compound (B) containing at least one Si-H bond and at least one Si-X bond, wherein X is a halogen, i.e. a fluorine, chlorine, bromine or iodine group, preferably chlorine, as well as mixtures of two or more such compounds present in the composition.

[0356] 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, wherein 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 (') in the composition according to the invention.

[0357] The silane compound (A') contained in the composition may be a silane compound having substituents selected only from halogen atoms and hydrogen atoms, but preferably the composition contains an organosilane, ie a compound (A') additionally having at least one Si-R bond, wherein R is an organic group.

[0358] According to one embodiment of the present invention, the organic group R comprises an optionally substituted, but preferably unsubstituted, group independently selected from: alkyl, aryl, alkenyl, alkynyl, alkaryl, aralkyl, aralkenyl, aralkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, cycloaralkyl, cycloaralkenyl and cycloaralkynyl, even more preferably selected from alkyl, cycloalkyl, alkenyl and aryl, even further preferably selected from methyl, ethyl, vinyl and phenyl, and most preferably R is methyl.

[0359] Metal halide (C')

[0360] Metal halides (C') are compounds comprising one or more metals and one or more halides, preferably they are ionic compounds comprising one or more metal cations and one or more halide anions.

[0361] In one embodiment of the present invention, the metal halide (C') is selected from binary metal halides, preferably from alkali metal halides and alkaline earth metal halides, more preferably from alkali metal chlorides and alkaline earth metal chlorides, even more preferably from the group consisting of lithium chloride, sodium chloride, potassium chloride, magnesium chloride, calcium chloride, even further preferably from magnesium chloride, sodium chloride or calcium chloride, most preferably the metal hydride is calcium chloride.

[0362] 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 the halosilane.

[0363] Heterocyclic ionic liquids

[0364] As already defined above, heterocyclic ionic liquids are salts comprising heterocyclic anions and / or cations which are liquid under the conditions of the process according to the invention. Typically, the melting point of the salt or ionic liquid is below about 150° C., preferably below about 140° C., more preferably below about 120° C., still more preferably below about 100° C., and most preferably below about 50° C.

[0365] According to one embodiment 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., it must include at least one atom other than carbon and hydrogen atoms as a ring member, wherein the cyclic structure may be aromatic or non-aromatic.

[0366] Ring structures consisting only of carbon atoms having one or more heteroatom substituents are not considered to be heterocycles according to the present invention. The heteroatoms are generally selected from oxygen atoms (O), sulfur atoms (S), phosphorus atoms (P) and nitrogen atoms (N), with P-heterocycles and N-heterocycles being generally preferred.

[0367] While there is no limitation on the ring size of the heterocyclic structure, the number of heteroatoms present in the heterocyclic ring, and the type of heteroatoms, it is preferred that the heterocyclic structure be a 5- or 6-membered ring containing one or two heteroatoms, wherein the heteroatoms are preferably selected from N atoms and P atoms. These structures may be aromatic or non-aromatic.

[0368] With respect to the compositions of the present invention, the same heterocyclic ionic liquids as described above for the methods of the present invention are utilized and are preferred.

[0369] In one embodiment according to the present invention, each X in the silane compound (A') is a chlorine atom, and the metal halide (C') is a metal chloride.

[0370] In a further embodiment according to the present invention, the silane compound (A') is a monosilane, preferably an organohydrogenated chloromonosilane.

[0371] According to this embodiment of the present invention, the silane compound (A') is an organohydrohalosilane having the formula RSiX2H, RSiXH2 and R2SiXH, wherein the organic substituent R is preferably independently selected from C1-C12 alkyl or phenyl, more preferably selected from methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl or phenyl, and most preferably selected from methyl and phenyl.

[0372] According to an embodiment, while X is independently selected from F, Cl, Br or I substituents, preferably each X represents a Cl atom.

[0373] The most preferred silane compounds (A') according to embodiments are MeSiH2Cl, MeSiHCl2 and Me2SiHCl.

[0374] In a more specific embodiment according to the present invention, the silane compound (A') is selected from the following monosilanes:

[0375] R x SiH y Cl z (I'),

[0376] Wherein R is an organic group,

[0377] x = 0 to 2, preferably 1 or 2,

[0378] y = 1-3, preferably 1 or 2,

[0379] z = 1-3, preferably 1 or 2, and

[0380] x+y+z=4.

[0381] The monosilane (A') according to this embodiment can be a chlorosilane without any organic group R, i.e., x=0 in the general formula (I). Preferred halogenated monosilanes according to the embodiment are HSiCl3, HSiBr3, and HSiI3, of which SiCl4 and HSiCl3 are most preferred. More preferably, the monosilane (A') is an organosilane, wherein x is 1 or 2, and y is preferably 1 or 2.

[0382] Preferably, the silane compound (A') is selected from the following organosilanes:

[0383] R x SiHy Cl z (I'),

[0384] Wherein R is an organic group,

[0385] x = 1 to 2,

[0386] y = 1 or 2,

[0387] z = 1 or 2, and

[0388] x+y+z=4.

[0389] According to the embodiment, preferred organosilanes are R2SiHCl, RSiH2Cl and RSiHCl2. Further preferably, the organic group R is selected from methyl, ethyl, phenyl and vinyl. The most preferred monosilane products (A') are Me2SiHCl, MeSiHCl2 and MeSiH2Cl.

[0390] In one embodiment according to the present invention, the composition of the present invention as described herein additionally comprises one or more monosilane compounds (A") of the general formula

[0391] R x SiH y (I”),

[0392] Wherein R is an organic group,

[0393] x = 0 to 2, preferably 1 or 2, and

[0394] y = 2 to 4, preferably 2 or 3, and

[0395] x+y=4.

[0396] The monosilane compound of formula (I") is generally formed in the process of the invention by complete reduction of the chlorosilane. Preferably, the amount of hydrogenated monosilane of formula (I") relative to the amount of hydrogenated monochlorosilane of formula (I') is as low as possible.

[0397] Preferably, the silane compound (A") is selected from the following organosilane compounds:

[0398] R x SiH y in

[0399] x = 1 or 2,

[0400] y = 2 or 3,

[0401] x+y=4.

[0402] Preferred organomonosilanes of formula (I") according to embodiments are R2SiH2 and RSiH3. Preferably, the organic group R is selected from methyl, ethyl, phenyl and vinyl. The most preferred monosilane compounds (I") are Me2SiH2 and MeSiH3.

[0403] It is also preferred that one or more organic groups R

[0404] R x SiH y (I”),

[0405] in it

[0406] x = 1 or 2,

[0407] y=2 or 3,

[0408] x+y=4,

[0409] The same as in the organomonosilane compound (A') contained in the composition. Further preferably, compound (A") is a silane compound formed from the corresponding silane compound (A') by replacing any Si-X bond with a Si-H bond.

[0410] In one 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, even more preferably about 15:1 or greater.

[0411] In another embodiment according to the present invention, one or two organic groups R of the silane compound (A') are selected from monosilanes of the following general formula:

[0412] R x SiH y Cl z (I'),

[0413] Wherein R is an organic group,

[0414] x = 0 to 2, preferably 1 or 2,

[0415] y = 1-3, preferably 1 or 2,

[0416] z = 1-3, preferably 1 or 2, and

[0417] x+y+z=4,

[0418] Independently selected from alkyl, cycloalkyl or phenyl, preferably R is methyl, ethylvinyl or phenyl, most preferably R is methyl.

[0419] In another embodiment of the present invention, compound (A') is selected from Me2SiHCl, MeSiH2Cl, MeSiHCl2, preferably compound (A') is Me2SiHCl.

[0420] In one 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.

[0421] In another embodiment of the present invention, the heterocyclic ionic liquid is selected from N-heterocyclic quaternary ammonium ionic liquids and P-heterocyclic phosphonium ionic liquids, preferably the heterocyclic ionic liquid is selected from N-heterocyclic aromatic quaternary ammonium ionic liquids and P-heterocyclic aromatic quaternary phosphonium ionic liquids.

[0422] More preferably, the heterocyclic ionic liquid is selected from the group of aromatic heterocyclic quaternary ammonium salts comprising pyridinium salts, imidazolium salts, 1,2,3-triazolium salts, imidazolinium salts, pyrrolium salts, the group of non-aromatic heterocyclic quaternary ammonium salts comprising morpholinium salts, piperidinium salts, piperazinium salts and pyrrolidinium salts, and the group of aromatic heterocyclic quaternary phosphonium salts comprising phosphonium salts, preferably the ionic liquid is selected from 1-substituted imidazolium salts and 1-substituted pyridinium salts, preferably Preferably, the alkyl group is 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 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 EthylMIMCl and HexMIMCl.

[0423] In one embodiment of the present invention, the silane compound (A') is an organic monosilane compound (A') of the following general formula:

[0424] R x SiH y Cl z (I'),

[0425] Wherein R is an organic group,

[0426] x = 1 to 2,

[0427] y = 1 or 2,

[0428] z = 1 or 2, and

[0429] x+y+z=4,

[0430] Metal halide (C') is CaCl2,

[0431] And the heterocyclic ionic liquid is an N-heterocyclic quaternary ammonium ionic liquid.

[0432] 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 having at least one Si—H bond and at least one Si—X bond (A′) is in the range of about 0.1 mol% to about 1500 mol%, preferably about 0.2 mol% to about 1000 mol%, more preferably about 0.4 mol% to about 600 mol%, even more preferably about 0.7 mol% to about 300 mol%, further preferably about 0.7 mol% to about 100 mol%, even further preferably about 2 mol% to about 100 mol%, and most preferably about 5 mol% to about 100 mol%.

[0433] In a further embodiment according to the present invention, compound (A') is Me2SiHCl, compound (A") is Me2SiH2, and the metal halide is CaCl2.

[0434] In yet another embodiment according to the present invention, compound (A') is MeSiH2Cl or MeSiHCl2, compound (A") is MeSiH3, and the metal halide is CaCl2.

[0435] In a preferred embodiment according to the present invention, the silane compound (A') is Me2SiHCl,

[0436] Metal halide (C') is CaCl2,

[0437] The heterocyclic ionic liquid is an N-heterocyclic quaternary ammonium ionic liquid,

[0438] The molar ratio of the N-heterocyclic quaternary ammonium ionic liquid to Me2SiHCl is in the range of about 0.7 mol-% to about 300 mol-%, preferably about 0.7 mol-% to about 100 mol-%, further preferably about 2 mol-% to about 100 mol-%, and most preferably about 5 mol-% to about 100 mol-%, and 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, even more preferably about 15:1 or greater.

[0439] It will be understood that any numerical range recited herein includes all sub-ranges within that range and any combination of the various endpoints of such ranges or sub-ranges, whether recited in the Examples or anywhere else in the specification.

[0440] It will also be understood herein that any component of the invention herein, when described by any particular genus or species detailed in the Examples section of the specification, may, in one embodiment, be used to define an alternative corresponding definition of any endpoint of a range described elsewhere in the specification for that component, and thus, in one non-limiting embodiment, may be used to supplant such a range endpoint described elsewhere.

[0441] It will be further understood that any compound, material or substance disclosed explicitly or implicitly in the specification and / or recited in the claims as belonging to a group of structurally, compositionally and / or functionally related compounds, materials or substances includes individual representatives of the group and all combinations thereof.

[0442] Although the above description contains many specifics, these details should not be interpreted as limiting the scope of the invention, but only as examples of its preferred embodiments. Those skilled in the art may envision many other possible changes within the scope and spirit of the invention as defined by the appended claims.

[0443] Overview of Preferred Embodiments of the Invention

[0444] In the following, preferred embodiments of the present invention are summarized:

[0445] 1. A process for preparing one or more silane compounds (A) having at least one Si—H bond,

[0446] It comprises the steps of subjecting one or more compounds (B) having at least one Si-X bond, wherein X is a halogen atom, to a reaction with one or more metal hydrides (C) in the presence of one or more heterocyclic ionic liquids.

[0447] 2. The method according to 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.

[0448] 3. The method according to any one of the preceding embodiments, wherein the compound having at least one Si—H bond (A) is an organomonosilane compound, preferably an organohydrochloromonosilane.

[0449] 4. The method according to any one of the preceding embodiments, wherein the compound having at least one Si-X bond (B) is an organosilane compound, preferably an organoperchlorosilane, more preferably an organoperchloromonosilane compound.

[0450] 5. The method according to any one of the preceding embodiments, wherein the product (A) is selected from the group consisting of monosilanes of formula (I)

[0451] R x SiH y Cl z (I),

[0452] Wherein R is an organic group,

[0453] x=0 to 3, preferably 0, 1, 2 and 3,

[0454] y = 1 to 4, preferably 1 to 2, most preferably 1

[0455] z = 0 to 3, preferably 0, 1, 2 and 3, and

[0456] x+y+z=4.

[0457] 6. The method according to any one of the preceding embodiments, wherein the product (A) is selected from the group consisting of monosilanes of formula (I)

[0458] R x SiH y Cl z (I),

[0459] Wherein R is an organic group,

[0460] x=1 to 3, preferably 1 to 2,

[0461] y=1 to 3, preferably 1 to 2,

[0462] z = 0 to 2, preferably 1 to 2, and

[0463] x+y+z=4.

[0464] 7. The method according to any one of the preceding embodiments, wherein the compound (B) having at least one Si-X bond is selected from the group consisting of organochloromonosilanes of formula (II)

[0465] R a SiH b Cl c (II)

[0466] Where R is as defined above,

[0467] a=1 to 3,

[0468] b = 0 to 2,

[0469] c = 1 to 3, and

[0470] a+b+c=4.

[0471] 8. The method according to any one of the preceding embodiments, wherein R is independently selected from alkyl, cycloalkyl or phenyl, preferably R is methyl.

[0472] 9. The method according to any one of the preceding embodiments, wherein compound (A) is selected from Me2SiHCl, MeSiH2Cl, MeSiHCl2, HSiCl3, Me3SiH, preferably compound (A) is Me2SiHCl.

[0473] 10. The method according to any one of the preceding embodiments, wherein compound (B) is selected from Me2SiCl2, MeSiCl3, SiCl4 and Me3SiCl, preferably compound (B) is Me2SiCl2.

[0474] 11. The method according to any one of the preceding embodiments, wherein 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, preferably the metal hydride (C) is selected from LiH, NaH, KH, MgH2, CaH2 and LiAlH4, and most preferably the metal hydride (C) is CaH2.

[0475] 12. The method according to any one of the preceding embodiments, wherein the method is performed in the absence of any metal hydride reagent (C) other than CaH2.

[0476] 13. The method according to any of the preceding embodiments, wherein the molar ratio of hydride ions of the one or more metal hydrides in the reaction mixture relative to the halogen atoms, preferably chlorine atoms, of the one or more compounds (B) is in the range of about 0.01 to about 300, more preferably about 0.1 to about 10, even more preferably about 0.4 to about 6, and most preferably about 0.7 to about 3.

[0477] 14. The method according to any one of the preceding embodiments, wherein the heterocyclic ionic liquid is selected from N-heterocyclic ionic liquids and P-heterocyclic ionic liquids.

[0478] 15. The method according to any one of the preceding embodiments, wherein the heterocyclic ionic liquid is selected from N-heterocyclic aromatic ionic liquids and P-heterocyclic aromatic ionic liquids.

[0479] 16. The method according to any one of the preceding embodiments, wherein the heterocyclic ionic liquid is selected from N-heterocyclic quaternary ammonium ionic liquids and P-heterocyclic phosphonium ionic liquids.

[0480] 17. The method according to any one of the preceding embodiments, wherein the heterocyclic ionic liquid is selected from N-heterocyclic aromatic quaternary ammonium ionic liquids and P-heterocyclic aromatic quaternary phosphonium ionic liquids.

[0481] 18. The method according to any one of the preceding embodiments, wherein the heterocyclic ionic liquid is selected from the group of aromatic heterocyclic quaternary ammonium salts comprising pyridinium salts, imidazolium salts, 1,2,3-triazolium salts, imidazolinium salts, pyrrolium salts, the group of non-aromatic heterocyclic quaternary ammonium salts comprising morpholinium salts, piperidinium salts, piperazinium salts and pyrrolidinium salts, and the group of aromatic heterocyclic quaternary phosphonium salts comprising phosphonium salts.

[0482] 19. The method according to any one of the preceding 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, even more preferably EthylMIMCl and HexMIMCl.

[0483] 20. The method according to any of the preceding embodiments, wherein the melting point of the ionic liquid is below about 150°C, preferably below about 100°C, more preferably below about 80°C, still more preferably below about 60°C, even more preferably below about 40°C, and most preferably below about 30°C.

[0484] 21. The method according to any one of the preceding 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 about 0.1 mol-% to about 1500 mol-%, preferably about 0.2 mol-% to about 1000 mol-%, more preferably about 0.4 mol-% to about 600 mol-%, even more preferably about 0.7 mol-% to about 300 mol-%, further preferably about 0.7 mol-% to about 100 mol-%, even further preferably about 2 mol-% to about 100 mol-%, and most preferably about 5 mol-% to about 100 mol-%.

[0485] 22. The method according to any one of the preceding embodiments, wherein the method is carried out in the absence of an ether solvent, preferably in the absence of an ether solvent and a linear or cyclic aliphatic hydrocarbon solvent, more preferably in the absence of an ether solvent and a linear or cyclic aliphatic hydrocarbon solvent and an aromatic hydrocarbon solvent, most preferably in the absence of any additional solvent other than one or more ionic liquids.

[0486] 23. The method according to any one of the preceding embodiments, wherein the method is performed in the absence of an acyclic quaternary ammonium salt and an acyclic quaternary phosphonium salt.

[0487] 24. The method according to any one of the preceding embodiments, wherein the reaction is carried out at a temperature 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.

[0488] 25. The method of any one of the preceding embodiments, wherein the reaction is carried out at a pressure of about 0.1 to about 20 bar, preferably about 0.3 to about 20 bar, more preferably about 1 to about 20 bar, even more preferably about 1 to about 10 bar, and most preferably about 1 to about 5 bar.

[0489] 26. The method of any one of the preceding embodiments, wherein the method is performed under inert conditions.

[0490] 27. The method according to any one of the preceding embodiments, wherein the method is performed continuously or discontinuously, such as in batches.

[0491] 28. The method according to any one of the preceding embodiments, wherein the method is performed in the absence of grinding or sonicating the reaction mixture.

[0492] 29. The method according to any one of the preceding embodiments, wherein the method is carried out without supplying hydrogen chloride and / or in the absence of a metal catalyst, preferably in the absence of aluminum chloride or a palladium catalyst.

[0493] 30. The process according to any one of the preceding embodiments, wherein the formed silane compound (A) having at least one Si—H bond, preferably Me 2 SiHCl, is separated from the reaction mixture by distillation and / or condensation.

[0494] 31. A method according to any of the preceding embodiments, wherein the starting material comprises about 75 wt.-% or more of one or more compounds (B), preferably about 85 wt.-% or more of one or more compounds (B), more preferably about 90 wt.-% or more of one or more compounds (B), and most preferably about 95 wt.-% or more of one or more compounds (B).

[0495] 32. The method according to any of the preceding embodiments, wherein the starting material contains about 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), most preferably about 95 wt-% or more of Me2SiCl2.

[0496] 33. The method according to any one of the preceding embodiments, wherein compound (A) is Me2SiHCl, compound (B) is Me2SiCl2, and the metal hydride is CaH2.

[0497] 34. The method according to any one of the preceding embodiments 1 to 32, wherein compound (A) is MeSiH2Cl or MeSiHCl2, compound (B) is MeSiCl3, and the metal hydride is CaH2.

[0498] 35. The method according to any one of embodiments 1 to 32 above, wherein the method comprises breaking one or more Si-Si bonds of one or more disilane or polysilane compounds (B) and / or one or more Si-C bonds of one or more carbodisilane compounds (B).

[0499] 36. The method according to the preceding embodiments 1 to 32 and 35, wherein compound (A) is selected from Me2SiHCl, MeSiH2Cl and MeSiHCl2, and compound (B) is selected from methylchlorodisilane and methylchloropolysilane, preferably methylchlorodisilane, and wherein the metal hydride is preferably CaH2 or MgH2.

[0500] 37. A composition comprising

[0501] - one or more silane compounds (A') having at least one Si-H bond and at least one Si-X bond,

[0502] Wherein X is a halogen atom,

[0503] - one or more metal halides (C'),

[0504] - one or more heterocyclic ionic liquids,

[0505] - Optionally, one or more silane compounds (A") having at least two Si-H bonds and no Si-X bonds.

[0506] 38. The composition of embodiment 37, wherein each X is a chlorine atom and the metal halide (C') is a metal chloride.

[0507] 39. The composition according to embodiments 37 and 38, wherein the silane compound (A') is a monosilane, preferably an organohydrogenated chloromonosilane.

[0508] 40. The composition according to embodiments 37 to 39, wherein the silane compound (A') is selected from monosilanes of the following general formula:

[0509] Rx SiH y Cl z (I'),

[0510] Wherein R is an organic group,

[0511] x = 0 to 2, preferably 1 or 2,

[0512] y = 1-3, preferably 1 or 2,

[0513] z = 1-3, preferably 1 or 2, and

[0514] x+y+z=4.

[0515] 41. The composition according to embodiments 37 to 40, wherein the silane compound (A') is selected from organomonosilanes of the following formula:

[0516] R x SiH y Cl z (I'),

[0517] Wherein R is an organic group,

[0518] x = 1 to 2,

[0519] y = 1 or 2,

[0520] z = 1 or 2, and

[0521] x+y+z=4.

[0522] 42. The composition according to embodiments 37 to 41, wherein the composition further comprises one or more monosilane compounds (A") of the following general formula:

[0523] R x SiH y (I”),

[0524] Wherein R is an organic group,

[0525] x = 0 to 2, preferably 1 or 2, and

[0526] y = 2 to 4, preferably 2 or 3, and

[0527] x+y=4,

[0528] Preferably, the silane compound (A") is selected from the organic monosilane compounds of the following general formula:

[0529] R x SiH y in

[0530] x = 1 or 2,

[0531] y=2 or 3,

[0532] x+y=4,

[0533] And preferably

[0534] The one or more organic groups of the organomonosilane compound (A") are the same as those in the organomonosilane compound (A').

[0535] 43. The composition according to embodiments 37 to 42, wherein compound (A") is a silane compound formed from the corresponding silane compound (A') by replacing any Si-X bonds with Si-H bonds.

[0536] 44. The composition according to embodiments 37 to 43, wherein one or two organic groups R of the silane compound (A') are independently selected from alkyl, cycloalkyl or phenyl, preferably R is methyl, ethylvinyl or phenyl, most preferably R is methyl.

[0537] 45. The composition according to embodiments 37 to 44, wherein compound (A') is selected from Me2SiHCl, MeSiH2Cl, MeSiHCl2, preferably compound (A') is Me2SiHCl.

[0538] 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, most preferably the metal chloride (C') is CaCl2.

[0539] 47. The composition according to embodiments 37 to 46, wherein the heterocyclic ionic liquid is selected from N-heterocyclic quaternary ammonium ionic liquids and P-heterocyclic ionic liquids, preferably the heterocyclic ionic liquid is selected from N-heterocyclic aromatic quaternary ammonium ionic liquids and P-heterocyclic aromatic quaternary ionic liquids.

[0540] 48. The composition according to embodiments 37 to 47, wherein the silane compound (A') is an organosilane compound (A') of the general formula

[0541] R x SiH y Cl z (I'),

[0542] Wherein R is an organic group,

[0543] x = 1 to 2,

[0544] y = 1 or 2,

[0545] z = 1 or 2, and

[0546] x+y+z=4,

[0547] Metal halide (C') is CaCl2,

[0548] And the heterocyclic ionic liquid is an N-heterocyclic quaternary ammonium ionic liquid.

[0549] 49. The composition according to embodiments 37 to 48, 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, 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 phosphonium salts, preferably 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 EthylMIMCl and HexMIMCl.

[0550] 50. The composition of 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.

[0551] 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 having at least one Si-H bond and at least one Si-X bond (A') is in the range of about 0.1 mol% to about 1500 mol%, preferably about 0.2 mol% to about 1000 mol%, more preferably about 0.4 mol% to about 600 mol%, even more preferably about 0.7 mol% to about 300 mol%, further preferably about 0.7 mol% to about 100 mol%, even further preferably about 2 mol% to about 100 mol%, and most preferably about 5 mol% to about 100 mol%.

[0552] 52. The composition of embodiments 37 to 51, wherein compound (A') is Me2SiHCl, compound (A") is Me2SiH2, and the metal halide is CaCl2.

[0553] 53. The composition of embodiments 37 to 51, wherein compound (A') is MeSiH2Cl or MeSiHCl2, compound (A") is MeSiH3, and the metal halide is CaCl2.

[0554] 54. The composition according to embodiments 37 to 52, wherein the silane compound (A') is Me2SiHCl,

[0555] Metal halide (C') is CaCl2,

[0556] The heterocyclic ionic liquid is an N-heterocyclic quaternary ammonium ionic liquid,

[0557] The molar ratio of the N-heterocyclic quaternary ammonium ionic liquid to Me2SiHCl is in the range of about 0.7 mol-% to about 300 mol-%, preferably about 0.7 mol-% to about 100 mol-%, further preferably about 2 mol-% to about 100 mol-%, and most preferably about 5 mol-% to about 100 mol-%, and

[0558] 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, even more preferably about 15:1 or greater.

[0559] The method of the present invention will be described in more detail below with reference to examples.

[0560] Example

[0561] The present invention is further illustrated by the following examples, but is not limited thereto.

[0562] General

[0563] All reactions were performed in a 100 ml Hastelloy pressure reactor equipped with a magnetic stirrer, a pressure gauge, an RTD sensor (Platinum Resistance Thermometer Sensor) Pt 100 from TC Company and three-way inlet / outlet valves.

[0564] 1-Ethyl-3-methylimidazolium chloride (ethyl MIM Cl) (98%) and 1-hexyl-3-methylimidazolium chloride (hexyl MIM Cl) (97%) were purchased from Sigma-Aldrich.

[0565] The products were analyzed and characterized by standard procedures, in particular by GC and GC / MS analysis.

[0566] Product Analysis

[0567] The products were analyzed by GC-MS.

[0568] The methods applied are described in the following table:

[0569] Table 1. GC-MS method description

[0570]

[0571] Under the given GC conditions, the retention times are as follows:

[0572] Me2SiH2(H2)0.908 min

[0573] Me2SiHCl (H1) 0.997 min

[0574] Me2SiCl2 (precursor) 1.192 min

[0575] Furthermore, the identities of the compounds Me2SiH2 and Me2SiHCl were confirmed by MS fragmentation analysis:

[0576] Characteristic GC-MS fragments of H2 and H1

[0577] Me2SiH2(H2)M=60 fragments found 59 (MH) and 58 (M-2H)

[0578] Me2SiHCl (H1) M = 94.5 fragments found 93 (MH) and 79 (M-CH3)

[0579] Example 1 (Comparative Example):

[0580] Reaction of Me2SiCl2 with LiH and Bu4PCl in THF

[0581] 0.19 g (0.6 mmol) Bu4PCl was dissolved in 15 ml of anhydrous THF and placed in the reactor.

[0582] Add 0.2 g (25.2 mmol H -) LiH. The autoclave was closed and cooled to 4°C. 3 g of Me2SiCl2 was injected using a syringe through a three-way valve. The temperature of the reaction mixture immediately rose to 17°C. An additional 13.2 g of Me2SiCl2 was injected (a total of 16.2 g Me2SiCl2 = 126 mmol), the reactor was closed, and heated to 120°C for 4 hours. After cooling to room temperature, the composition of the liquid phase (which contained silane, ether solvent, and some salts) was analyzed by GC (~10% anhydrous toluene solution; the detailed GC method is described in Table 1). The area ratio H1:H2 of the target product Me2SiHCl (H1) to the undesired intermediate Me2SiH2 (H2) was determined. The results are shown in Table 2.

[0583] Example 2 (Comparative Example)

[0584] Reaction of Me2SiCl2 with CaH2 and Bu4PCl in THF

[0585] 0.19 g (0.6 mmol) Bu4PCl was dissolved in 15 ml of anhydrous THF and placed in a reactor. 0.53 g (25.2 mmol H - ) CaH2. The autoclave was closed and cooled to 4°C. 16.2 g (126 mmol) of Me2SiCl2 was injected using a syringe through a three-way valve. The temperature of the reaction mixture immediately rose to 13°C. The reactor was closed and heated to 120°C for 4 hours. After cooling to room temperature, the composition of the liquid phase (which contained silane, ether solvent and some salts) was analyzed by GC (~10% anhydrous toluene solution; the detailed GC method is described in Table 1). The area ratio H1:H2 of the target product Me2SiHCl (H1) to the undesired intermediate Me2SiH2 (H2) could not be determined because neither Me2SiHCl nor Me2SiH2 was formed in detectable amounts.

[0586] Example 3

[0587] Reaction of Me2SiCl2 with CaH2 in 1-ethyl-3-methylimidazolium chloride (EthylMIM Cl)

[0588] 15 g of 1-ethyl-3-methylimidazolium chloride (98%) and 0.53 g (25.2 mmol H -) and CaH2 were mixed and placed in a reactor. 16.2 g of Me2SiCl2 (126 mmol) was injected through a three-way valve, the reactor was closed, and heated to 120°C for 4 hours. The reaction mixture was then cooled to room temperature. It consisted of a solid phase that was well separated from the liquid phase. The composition of the liquid silane phase was analyzed by GC. The area ratio H1:H2 of the desired product Me2SiHCl (H1) to the undesired intermediate Me2SiH2 (H2) was then determined.

[0589] Example 4

[0590] Reaction of Me2SiCl2 with CaH2 in 1-hexyl-3-methylimidazolium chloride (HexMIM Cl)

[0591] 15 g of 1-hexyl-3-methylimidazolium chloride (97%) and 0.53 g (25.2 mmol H - ) and CaH2 and placed in a reactor. 16.2 g Me2SiCl2 (126 mmol) were injected through a three-way valve, the reactor was closed and heated to 120°C for 4 hours. Afterwards, the reaction mixture was cooled to room temperature. It consisted of a solid phase that was well separated from the liquid phase. The composition of the liquid silane phase was analyzed by GC. The area ratio H1:H2 of the target product Me2SiHCl (H1) to the undesired intermediate Me2SiH2 (H2) was determined. The higher the ratio, the more target product was formed relative to the intermediate.

[0592] Table 2 below summarizes the reaction parameters and composition H1:H2.

[0593]

[0594] The data show that CaH2 is non-reactive under state-of-the-art conditions applicable to LiH (see Comparative Examples 1 and 2).

[0595] However, the combination of CaH2 and sufficiently polar heterocyclic ionic liquids can be used to selectively synthesize Me2SiHCl from Me2SiCl2 under mild conditions without the need for any ether solvents or additional activation steps (see Examples 3 and 4).

[0596] The volatile silane mixture can be distilled off from the ionic liquid / CaCl mixture under vacuum and processed directly since no organic solvent is present. The data also show that the efficiency of the ionic liquid is not a direct function of melting point. Both low melting point (-75°C for 1-hexyl-3-methylimidazolium chloride) and high melting point ionic liquids (77-79°C for 1-ethyl-3-methylimidazolium chloride) combined with CaH produce the target product MeSiHCl in high proportions, thus providing a direct, low-cost route. Without wishing to be bound by theory, the combination of sufficiently high fluidity of the mixture at the reaction temperature and sufficiently high polarity is key to a successful reaction.

Claims

1. A process for preparing one or more silane compounds (A) having at least one Si—H bond, The following steps are involved: One or more compounds having at least one Si-X bond (B) are subjected to a reaction with one or more metal hydrides (C) in the presence of one or more heterocyclic ionic liquids, wherein X is a halogen atom. 2 . The method according to claim 1 , wherein the compound (A) having at least one Si—H bond is an organosilane compound, preferably an organohydrochloromonosilane.

3. The process according to claim 1, wherein the product (A) is selected from the group consisting of monosilanes of formula (I) (I)， Wherein R is an organic 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 ， Wherein preferably R is independently selected from alkyl, cycloalkyl or phenyl, preferably R is methyl.

4. The method according to any one of the preceding claims, wherein compound (A) is selected from 、 、 、 、 , preferably compound (A) is .

5. The method according to any one of the preceding claims, wherein 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, preferably the metal hydride (C) is selected from LiH, NaH, KH, 、 and , the most preferred metal hydride (C) is , wherein preferably the molar ratio of the hydride ions of the one or more metal hydrides relative to the halogen atoms, preferably chlorine atoms, of the one or more compounds (B) in the reaction mixture is in the range of about 0.01 to about 300, more preferably about 0.1 to about 10, even more preferably about 0.4 to about 6, and most preferably about 0.7 to about 3.

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

7. The method according to any one of the preceding claims, wherein the ionic liquid is selected from 1-substituted imidazolium salts and 1-substituted pyridinium salts, preferably selected from replaced, replaced, Replaced and Substituted imidazolium salts, more preferably 1-alkyl substituted replaced, replaced, Replaced and Substituted imidazolium salts, and even more preferably EthylMIMCl and HexMIMCl.

8. The process according to any one 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 about 0.1 mol% to about 1500 mol%, preferably about 0.2 mol% to about 1000 mol%, more preferably about 0.4 mol% to about 600 mol%, even more preferably about 0.7 mol% to about 300 mol%, further preferably about 0.7 mol% to about 100 mol%, even further preferably about 2 mol% to about 100 mol%, and most preferably about 5 mol% to about 100 mol%.

9. The process according to any one of the preceding claims, wherein compound (A) is , compound (B) is , and the metal hydride is .

10. The method according to any one of claims 1 to 8, wherein compound (A) is or , compound (B) is , and the metal hydride is .

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

12. The method according to claims 1 to 8, and 11, wherein compound (A) is selected from 、 and , and compound (B) is selected from methylchlorodisilane and methylchloropolysilane, preferably methylchlorodisilane, and wherein the metal hydride is preferably or .

13. A composition comprising - one or more silane compounds (A') having at least one Si-H bond and at least one Si-X bond, wherein 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.

14. The composition according to claim 13, wherein the silane compound (A') is an organic monosilane compound (A') of the following general formula: (I’)， Wherein R is an organic group, x = 1 to 2, y = 1 or 2, z = 1 or 2, and ， Metal halide (C') is , And the heterocyclic ionic liquid is an N-heterocyclic quaternary ammonium ionic liquid.

15. The composition according to claim 13 and 14, wherein the silane compound (A') is , Metal halide (C') is , The heterocyclic ionic liquid is an N-heterocyclic quaternary ammonium ionic liquid, The N-heterocyclic quaternary ammonium ion liquid The molar ratio of is in the range of about 0.7 mol-% to about 300 mol-%, preferably about 0.7 mol-% to about 100 mol-%, further preferably about 2 mol-% to about 100 mol-%, and most preferably about 5 mol-% to about 100 mol-%, and The composition comprises ,in right The molar ratio of oxadiazole to oxadiazole 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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