WO2013034705A1 - Utilisation de polysiloxanes ioniques comme solvants dans des réactions organiques - Google Patents

Utilisation de polysiloxanes ioniques comme solvants dans des réactions organiques Download PDF

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WO2013034705A1
WO2013034705A1 PCT/EP2012/067532 EP2012067532W WO2013034705A1 WO 2013034705 A1 WO2013034705 A1 WO 2013034705A1 EP 2012067532 W EP2012067532 W EP 2012067532W WO 2013034705 A1 WO2013034705 A1 WO 2013034705A1
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ionic
use according
polysiioxane
solvent
groups
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PCT/EP2012/067532
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English (en)
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Johannes Gerardus Petrus Delis
Carsten KOOPMANNS
Roland Wagner
Karl-Heinz Sockel
Monika FRIEDERICHS
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Momentive Performance Materials Gmbh
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Publication of WO2013034705A1 publication Critical patent/WO2013034705A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0834—Compounds having one or more O-Si linkage
    • C07F7/0838—Compounds with one or more Si-O-Si sequences
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/045—Polysiloxanes containing less than 25 silicon atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/38—Polysiloxanes modified by chemical after-treatment
    • C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
    • C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen

Definitions

  • the invention concerns the usage of ionic polysiloxan.es as ionic liquids as a solvent in organic reactions in particular in hydrosilylation reactions.
  • Ionic liquids are molecules which can efficiently replace the conventional organic solvents used in chemical processes and operations. A number of such applications have been reported.
  • Known ionic liquids are based on organic compounds functional i zed with ionic groups. So far polysiloxane-based ionic compounds have not been envisaged as ionic liquids. The reason for this might be found in the expectation of the skilled person in the art, that polysiloxane-based ionic compounds being liquid at temperatures below e.g. 150°C would be too lipophilic, and that hydrophilic polysiloxane-based ionic compounds would have too high melting points (see e.g. US7834087).
  • Hydrocarbon based ionic liquids are known and widely used for the recovery of catalysts from organic reaction mixtures (Hemant G. Joglekar, Imran Rahman, Bhaskar I). Kulkami, Chem. Eng. Technol. 2007, 30, No. 7, 819 -828; W. Hasenpusch, CLB Chemie in Labor und Biotechnik, 57-04-2006, 176). US20040014925(A1), EP1382630(B1) and B. Weyershausen, K. Hell and U. Hesse Green Chem., 2005, 7, 283- 287 describe the use of hydrocarbon based ionic liquids as catalyst carriers in hydrosilylation reactions.
  • US20080045737(A 1 ) claims the use of hydrocarbon-based ionic liquids as catalyst carrier in a continuous process to produce organo-silanes in a reactive distillation column.
  • US20020198100(A 1 ) describes the use of hydrocarbon-based ionic liquids as catalyst carrier in which the ionic liquid is immobilized on a carrier making use of silanes.
  • ionic liquids of varying polarity, solubility and melting point have to be applied.
  • JP-A-2G08239514 discloses the amino-siloxane-type ionic liquids for use as an electrolyte for electrochemical devices such as lithium ion batteries, solar cells, capacitors and display elements. Also this document is silent about the possible use of such compounds as solvent in organic reactions.
  • Solar Energy Materials & Solar Ceils 92 (2008) 126-135 relates to Imidazoli um-based ionic liquid derivatives for application in electrochromic devices. Again also this document is silent about the possible use of such compounds as solvent in organic reactions.
  • J. Phys. Chem. B 2007, 111, 4819-4829 relates to the intermolecular interactions and Dynamics of Room Temperature Ionic Liquids that have Silyl- and Siloxy-Substituted Imidazolium Cations.
  • one specific example has a Si-0-Si-CH 2 -imidazolium cation moiety.
  • the document only addresses physical properties of the compounds. A possible use of the characterized compounds is not addressed in this document.
  • polysiloxane-based ionic compounds can be used as ionic liquids, thereby tremendously extending the range of possible applications of such ionic liquids due to the unique properties of such that polysiloxane-based ionic compounds, such as very low achievable melting points, high variability of available structures leading to a high variability of available properties.
  • polysiloxane-based ionic compounds such as quaternary ammonium modified silicone compounds can be used as solvent in organic reactions, for example as agents for the recovery of metal catalysts from organic, more specifically hydrocarbon or silicone based reaction systems (e.g.
  • Polarity, solubility and melting point of the quatemized silicone can be varied in a wide range and adjusted according to the demands for the ionic liquid.
  • the present invention provides a novel use of ionic polysiloxanes as ionic liquids as a solvent in organic reactions, in particular, as a solvent in hydrosilylation reactions, especially to recover the catalyst in such reactions.
  • the catalyst is preferably a platinum-based catalyst, like a platinum compound, and preferably the ionic liquid is used to revover the said platinum- based catalyst from a hydrosilylation reaction mixture and still more preferably such a revovered mixture comprising the ionic liquid and the platinum-based catalyst is reused in the hydrosilylation reaction.
  • An ionic liquid (IL) in the context of the present invention refers in general to an ionic compound in the liquid state, preferably having a melting point at normal pressure which is below 150 °C, preferably below 120 °C, and more preferably below 100 °C, more preferably below 80 °C, still more preferably below 50 °C and even more preferably below 30 °C.
  • Such ionic liquids are sometimes also referred to in the art as liquid electrolytes, ionic melts, ionic fluids, fused salts, liquid salts, or ionic glasses.
  • the melting point of the ionic polysiloxane is usually determined with a differential scanning calorimeter at a heating rate of 1 °K /minute and determining T-fusion for example with a Mettler DSC1 apparatus.
  • ILs like the pol ysi loxane-based ILs of the invention thus may find a variety of industrial applications in particular in chemical industry, in particular, as solvent in various processes, like hydrocarbon synthesis, as solvent in cellulose processing, as dispersants, e.g.
  • the present invention relates to the use of an ionic polysiloxane compound as a solvent.
  • the ionic polysiloxane compound acts as a carrier medium, to dissolve or disperse certain chemical compounds.
  • the ionic polysiloxane compound according to the invention is generally useful in various organic reactions, like in particular hydrosilylation reactions, that is the reaction of unsaturated organic compounds is SiH-functional silicon compounds, involving the use of the metal catalyst described in more detail below.
  • the ionic polysiloxane compounds according to the invention may act as a solvent in separation operations, including liquid/liquid or gas/liquid separation operations.
  • liquid ionic polysiloxanes according to the invention are useful as dispersants due to the simultaneous presence of ionic groups and more lipophilic groups like the polysiloxane moieties.
  • the liquid ionic polysiloxanes according to the invention are useful in systems having multiple phases, like heterogenous reaction mixtures, for example in phase-transfer catalysed reactions, or heterogeneous separation systems.
  • Another application of the liquid ionic polysiloxancs according to the invention is their use as a catalyst for example in homogeneous or heterogeneous catalytic reactions, like in hydrogen rearrangement reactions, such as the disproportionation of hydrogen silanes, as catalyst in phase-transfer reactions etc..
  • liquid ionic polysiloxanes according to the invention is their use as ligand source for example in transition metal catalysed processes, for example hydrogenation and hydroformulation processes, image processes.
  • liquid ionic polysiloxanes according to the invention is their use as heat transfer or heat storage fluids for in solar thermal energy systems.
  • the ionic polysiloxanes used in accordance with the present invention generally have a melting point at normal pressure of below 150 °C, preferably below 120 °C, more preferably below 100 °C, still more preferably below 80 °C, still more preferably below 50 °C and even more preferably below 30 °C.
  • Suitable ionic polysiloxanes according to the invention have preferably a number average molecular weight of less than 2000, more preferably less than 1500 g mol, more preferably less than 1000 g mol, more preferably of less than 900 g/mol, more preferably of less than 800 g/mol, more preferably of less than 700 g/mol, more preferably less than 600 g/mol.
  • the number average molecular weight can be determined in particular by using gel permeation chromatography with polystyrene as standard. Smaller molecules might be also characterized auxiliary with NMR- techniques in regard to their molecular weights.
  • An ionic polysiloxane in the context of the present invention generally refers to a polysiloxane compound, that is, a compound having at least two siloxy groups, i.e. selected from the groups M, D, T, Q, according to the well-known nomenclature of silicones:
  • R represents an organic group, wherein at least one of the groups R comprises at least one functional ionic group. Depending on such functional ionic group the ionic polysiloxane comprises a suitable counter ionic group with opposite charge.
  • the ionic polysiloxane according to the invention have at least one ionic group attached to or being part of the polysiloxane-containing moiety, that is, the group R, which ionic group is preferably selected from the group consisting of ammonium, in particular quaternary ammonium groups, phosphonium, in particular quaternary phosphonium groups, phosphonate, sulfate, sulfonate, carhoxylate, and bis(sulfon)imide groups. More preferably are cationic groups, like ammonium, in particular quaternary ammonium groups, phosphonium, in particular quaternary phosphonium groups. Most preferably are quaternary ammonium groups.
  • the ionic polysiloxanes according to the invention preferably are linear polydiorganosiloxanes modified with ionic groups as internal, terminal and/or as side chain groups.
  • the term "internal" the context of this application means that ionic groups are present in the polydiorganosiloxanes backbone, thereby connecting more than one polydiorganosiloxane moieties.
  • the ionic polysiloxanes according to the invention are linear polydimethylsiloxanes having the aforementioned ionic groups.
  • the ionic polysiloxanes according to the invention in average have more than two silicon atoms.
  • the ionic polysiloxanes according to the invention include ammonium-polysiloxanes formula (I) -[Q-V] x - (I) in which x is 1 to 3, with x being an average value, but is also may be an integer from 1 to 3, in which Q is selected from the group consisting of
  • R in each case is hydrogen or a monovalent organic radical, Q not bonding to a carbonyl carbon atom,
  • V is selected from the group consisting of V and V in which
  • V 2 is selected from divalent, straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals having up to 20 carbon atoms
  • R 2 is hydrogen, a monovalent, straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radical having up to 10 carbon atoms, which may contain one or more groups selected from -0-, - ⁇ -, -C(O)- and -C(S)-, and which may if desired be substituted by one or more substituents selected from the group consisting of a hydroxyl group, and, if there are two or more groups -CONR 2 -, they may be identical or different,
  • radical V 2 may if desired by substituted by one or more hydroxyl groups, and the radical V 2 contains at least one polydiorganosiloxane group of the formula
  • R can be identical or different and is selected from the group consisting of
  • Ci to C 22 alkyl, fluoro(CrCio)alkyl and C 6 -Ci ® aryl, and m 0 to 18, preferably 0 to 9, still more preferably 0 to 4, with n being an average value, and ni is most preferably > 0.
  • V 1 is selected from divalent, straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals having up to 20 carbon atoms, which i desired may contain one or more groups selected from
  • V 1 may if desired be substituted by one or more hydroxyl groups, which comprise at least one group V , which compounds -[Q-V] x - (I) are terminated by R as defined above, and in which the positive charges resulting from the ammonium groups are neutralized by organic or inorganic anions, and mixtures thereof.
  • x 1.
  • These compounds correspond to alpha,omega-diammonium polydiorganosiloxanes.
  • they include alpha,omega-diquaternary ammonium polydiorganosiloxanes, i.e., R is not hydrogen.
  • These compounds correspond to ammonium polydiorganosiloxanes, optionally having two polydiorganosiloxane moieties, in case V is V and not V 1 .
  • the aforementioned compound can be prepared for example in accordance with WO2004041912.
  • mixtures of the above identified ionic polysiloxane compounds are comprised.
  • Specific ionic polysiloxanes according to the invention may include:
  • X is a divalent hydrocarbon residue having up to 10 carbon atoms, which may have a hydroxy! group and which may be interrupted by an oxygen atom
  • Y is a divalent hydrocarbon residue having up to 20 carbon atoms, which may have a hydroxy! group and which may be interrupted by an oxygen atom or an amino group
  • Z 1 is an optionally substituted alkyl group or Z 1 is
  • R 5 is C r C 20 -alkyl, Z 2
  • R 1 , R 2 , R 3 and R 4 are the same or different and are Cl-C4-alkyl or benzyl, and A " is an inorganic or organic anion, n is 1 to 10, preferably n is > 1 to 10, and m is 1 to 3.
  • diquaternary polysiloxanes of the formula (III) are also included. Also included are diquaternary polysiloxanes of the formula (III),
  • R 6 , R 7 , R 8 are each independent from each other C j -Cio-alkyl or C 2 -C 10 -alkylene, which may have one or more hydroxyl groups
  • R 9 , R 10 , R 12 , R 14 , R 15 are each independent from each other C,-C I0 -alkyl or C 2 -C 10 -alkylene, which may have one or more hydroxyl groups
  • R n is -O- or -NR 13 -, with R 13 being Ci-C4-alkyl- or hydroxyalkyl or hydrogen
  • s 2 to 4
  • M being a divalent hydrocarbon residue with up to 10 carbon atoms which may optionally have one or more hydroxy groups, preferably selected from the group consisting of: ⁇ (CH 2 )-,
  • r is an average number or an integer of 0 to 18, preferably 0 to 6, and still more preferably 0 to 4, most preferably r > 0, and B is an inorganic or organic anion. Also those compounds can be prepared in accordance with DE10036533.
  • Preferred anions in the ionic polysiloxane compounds with cationic groups in the polysiloxane moiety according to the invention include chloride, bromide, PF 6 "
  • alkyl sulfonate (RS0 3 ), sulfate, alkyl sulfate (ROS0 " ), carboxylates, bissulfonimides [(R-S(3 ⁇ 4-N-S0 2 -R) , wherein R is preferably CF 3 )], dialkyl phosphate (R2PO 4 " ).
  • the preferred anion is chloride.
  • Phosphonium (-R-P + (R) 3 ) -containing polysiloxanes are obtainable by alkylation of trialkyl- or triarylphosphines with halogenalkyl-substituted polysiloxanes or by alkylation of phosphine-polysiloxanes, the latter also being prepared by alkylation of the corresponding phosphines with halogenalkyl- substituted polysiloxanes (see e.g. Organikum, VEB Dcutscher Verlag der
  • Sulfonic acid groups (-SO3 " ) -containing polysiloxanes are obtainable by reacting epoxy-functional polysiloxanes with sodiumhydrogensulfite (e.g. Silicone,
  • Sulfate groups (-OS0 3 ⁇ ) -containing polysiloxanes are obtainable by reacting hydroxyalkyl functional polysiloxanes with amidosulfonic acid (see e.g.
  • Phosphonate-groups-containing polysiloxanes are obtainable by reacting alkenyl-polyorganosiloxanes with phosphorous acid ester.
  • Preferred cations for those anionic polysiloxanes include for example metal cations, ammonium cations etc., preferable ammonium cations.
  • Preferred ionic polysiloxanes according to the invention have up to 20 silicon atoms, preferably up to 10 silicon atoms still more preferably up to 6 silicon atoms.
  • Preferred ionic polysiloxanes include those having at least one polydimethylsiloxane chain.
  • alpha,omega ionically functionalized polydiorganosiloxanes preferably alpha,omega ionically functionalized polydimethylsiloxancs, and even more preferred alpha,omega-diquaternary ammonium groups functionalized polydimethylsiloxanes.
  • the ionic polysiloxanes have a partition coefficient log P in water/ 1-octanol at 20 °C of less than 0.5, which means that they are more polar, that is they are usually water-soluble or partially water-soluble at room temperature (20°C).
  • they Preferably they have a water solubility at 20° C of at least 1 g /100 ml, still more preferably of at least 10 g / 100 ml, still more preferably at least 20 g / 100 ml.
  • the preferred ionic quaternized silicone compounds include the structures: (1) ⁇ , ⁇ -diquaternary polysiloxanes,
  • Polyloop polyquaternary polysiloxanes are known from EP-A-282720.
  • Silicone quats i.e. quaternary ammonium groups
  • quat groups as well as the polyethylene oxide moieties in the side chains are described in US 5,098,979, US 5,153,294 and US 5,166,297.
  • Branched silicone quats containing alkylene oxide moieties can be synthesized using a quaternized trialkoxy silanes (US 5,602,224).
  • Silicone based block copolymers containing quat functions as well as polyether moieties are described in WO 02/10257, WO 02/10259 and US 2002/0103094 A.
  • the alkylene oxide structures are incorporated into the block copolymer as ⁇ , ⁇ -difunctional moieties.
  • WO 03/78504 describes branched silicone based block copolymers containing quat functions as well as polyether moieties.
  • Polyquaternary polysiloxane block copolymers containing reactive groups are described in WO 2004/090007.
  • Polyquaternary polysiloxane block copolymers containing polyether side groups are described in WO 2006/103075.
  • Octopus like polyquaternary polysiloxane Mock copolymers are described in WO 2007/014930.
  • Polyquaternary polysiloxane block copolymers containing amide, urethane and urea moieties are described in WO 2009/112418, WO 2009/112417, WO 2009/021989, WO 2008/142109, WO 2008/113831.
  • Polyquaternary polysiloxane block copolymers containing amino acid moieties are described in DE 10036522.
  • WO 02/10256 describes silicone based diquaternary compounds having a quaternized core and terminal silicone moieties.
  • ⁇ , ⁇ -Diquaternary siloxanes are described in US 4891166 , EP 17121, WO 99/32521 , DE 10253152, US 5235082, JP 20061 9918, DE 102007037345.
  • the ionic polysiloxanes have a molar concentration of the ionic groups defined as number of ionic groups in mmol per number average molecular weight in gram (as defined above) is from 0.1 to 25 mmol /g, preferably from 0.5 to 20 mmol /g, more preferably from 1 to 20 mmol / g, still more preferably from 1 to 10 mmol/g and even more preferably from 2 to 10 mmol / g.
  • the number average molecular weight is 500 g/mol, and there are in average 2 ionic groups in the molecule (i.e. 2 mol - 2000 mmol)
  • the mixture is distilled twice.
  • the mixture is heated to 82-84°C for 18 hours,
  • the non-sharp melting point was determined between 80-120 deg C.
  • this compound has a much lower molecular weight than the analogous polysiloxanc compound of example 3, it is solid at room temperature.
  • polysiloxane moieties in ionic liquids substantive reduction of melting points is possible thereby increasing the applicable range of compounds to a great extent. This allows for example in the above described hydrosilylation reaction to separate the ionic liquid comprising the catalyst at room temperature.

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  • Organic Chemistry (AREA)
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Abstract

L'invention concerne l'utilisation de polysiloxanes ioniques comme solvants dans des réactions organiques.
PCT/EP2012/067532 2011-09-09 2012-09-07 Utilisation de polysiloxanes ioniques comme solvants dans des réactions organiques WO2013034705A1 (fr)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2017048123A (ja) * 2015-08-31 2017-03-09 信越化学工業株式会社 アルケニルアミンの製造方法
CN107001637A (zh) * 2014-09-23 2017-08-01 迈图高新材料股份有限公司 用于处理基于氨基酸的底物的硅氧烷化合物及其组合物
JP2020000853A (ja) * 2018-06-26 2020-01-09 信越化学工業株式会社 生体電極組成物、生体電極、及び生体電極の製造方法

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JP2020000853A (ja) * 2018-06-26 2020-01-09 信越化学工業株式会社 生体電極組成物、生体電極、及び生体電極の製造方法
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