WO2019022878A1 - Method of making a mixture of far boiling silane and siloxane - Google Patents
Method of making a mixture of far boiling silane and siloxane Download PDFInfo
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- WO2019022878A1 WO2019022878A1 PCT/US2018/039010 US2018039010W WO2019022878A1 WO 2019022878 A1 WO2019022878 A1 WO 2019022878A1 US 2018039010 W US2018039010 W US 2018039010W WO 2019022878 A1 WO2019022878 A1 WO 2019022878A1
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- Prior art keywords
- rearrangement
- halodisiloxane
- halodisilane
- mixture
- boiling point
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- 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
- C07F7/12—Organo silicon halides
- C07F7/121—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20
- C07F7/128—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20 by reactions covered by more than one of the groups C07F7/122 - C07F7/127 and of which the starting material is unknown or insufficiently determined
Abstract
A method of producing a mixture of silanes and siloxane, the method comprising: subjecting a reaction mixture comprising a rearrangement effective amount of a rearrangement catalyst, a silane and siloxane mixture, wherein the silane and siloxane mixture comprises a halodisilane and a halodisiloxane, and, optionally, a solvent, to conditions sufficient to cause the rearrangement of the halodisilane to produce a reaction product mixture, wherein the reaction product mixture comprises two or more halodisilane rearrangement products and the halodisiloxane.
Description
METHOD OF MAKING A MIXTURE OF FAR BOILING SILANE AND SILOXANE
CROSS-REFERENCE TO RELATED APPLICATIONS
[0001] None
FIELD OF THE INVENTION
[0002] The present invention relates, generally, to a method of producing a mixture of silanes and siloxanes, comprising: subjecting a reaction mixture comprising a rearrangement catalyst and a mixture of a halodisilane and a halodisiloxane to conditions sufficient to cause the rearrangement of the halodisilane to form a reaction product mixture comprising two or more halodisilane rearrangement products and the halodisiloxane.
BACKGROUND OF THE INVENTION
[0003] Chlorosiloxanes can be used, among other things, as intermediates in making other higher molecular weight polysiloxanes and silicone resins. Many of the applications for chlorosiloxanes require high purity.
[0004] Several processes for producing chlorosiloxanes are known. For example, the partial hydrolysis of trichlorosilane at -78 °C to produce chlorosiloxanes has been taught. Chlorosiloxanes have also been produced as byproducts in processes to make trichlorosilane and polysilicon.
[0005] Process of producing trichlorosilane and polysilicon can produce mixtures of chlorosiloxanes with other close boiling silanes or disilanes. These close boiling byproducts make recovering and purifying the chlorosiloxanes by distillation inefficient, and multiple distillations are required to achieve higher purity levels. These multiple distillations add to production costs, still result in extremely low yields, and require significantly more capital and operating costs for sufficient separation design.
[0006] Therefore, there is a need for new methods for efficiently separating chlorosiloxanes from mixtures comprising close boiling silanes which may or may not include, for example, simple distillation or stripping in the methods.
BRIEF SUMMARY OF THE INVENTION
[0007] The present invention is directed to a method of producing a mixture of silanes and siloxane, comprising: subjecting a reaction mixture comprising a rearrangement effective amount of a rearrangement catalyst, a silane and siloxane mixture, wherein the silane and
siloxane mixture comprises a halodisilane and a halodisiloxane, and, optionally, a solvent, to conditions sufficient to cause the rearrangement of the halodisilane to produce a reaction product mixture, wherein the reaction product mixture comprises two or more halodisilane rearrangement products and the halodisiloxane.
[0008] The present invention is further directed to a method of separating a halodisiloxane from a mixture, comprising: subjecting a reaction mixture comprising a rearrangement effective amount of a rearrangement catalyst, a silane and siloxane mixture, wherein the silane and siloxane mixture comprises a halodisilane and a halodisiloxane, and, optionally, a solvent, to conditions sufficient to cause the rearrangement of the halodisilane to produce a reaction product mixture, wherein the reaction product mixture comprises two or more halodisilane rearrangement products and the halodisiloxane, and recovering the
halodisiloxane.
[0009] The method of the invention produces mixtures comprising chlorosiloxanes and far boiling silanes from mixtures of chlorosiloxanes and close boiling silanes. The methods of the invention also separate chlorosiloxanes from a mixture of chlorosiloxanes and close boiling silanes.
DETAILED DESCRIPTION OF THE INVENTION
[0010] A method of producing a mixture of silanes and siloxane, the method comprising: subjecting a reaction mixture comprising
a rearrangement effective amount of a rearrangement catalyst,
a silane and siloxane mixture, wherein the silane and siloxane mixture comprises a halodisilane and a halodisiloxane, and
optionally, a solvent,
to conditions sufficient to cause the rearrangement of the halodisilane to produce a reaction product mixture, wherein the reaction product mixture comprises two or more halodisilane rearrangement products and the halodisiloxane.
[0011] The rearrangement catalyst is any rearrangement catalyst that will catalyze the rearrangement of the halodisilane and not catalyze any significant reaction of the halodisiloxane, alternatively the rearrangement catalyst is an amine type rearrangement catalyst, a phosphonium type catalyst, a cyclic ether catalyst, or an acidic rearrangement catalyst, alternatively the rearrangement catalyst is an amine type rearrangement catalyst, a
phosphonium type catalyst, or an acidic rearrangement catalyst, alternatively an amine-type rearrangement catalyst.
[0012] The acidic rearrangement catalyst (also referred to as the acid rearrangement catalyst herein) is an organic compound containing a strong acid group which is dissolved in the inert liquid diluent present. By a strong acid group we mean that the organic acid has a pK of less than 3 and preferably less than 1.5. The acid is preferably a sulphonic acid but could alternatively be a phosphonic acid or an acid sulphate ester. Preferred sulphonic acids are aryl sulphonic acids, particularly alkylaryl sulphonic acids of the formula R'-Ar-SCbH, where Ar is an aromatic nucleus such as a benzene or naphthalene nucleus and R' is an alkyl group which may have 1 to 30 carbon atoms but preferably has 8 to 20 carbon atoms, for example dodecylbenzenesulphonic acid. Alternative sulphonic acids which are suitable include alkyl sulphonic acids and halogenated aryl or alkyl sulphonic acids, for example trifluorome thane sulphonic acid. Acidic rearrangement catalysts are known in the art and many are available commercially.
[0013] The amine type rearrangement catalyst is any rearrangement catalyst comprising amine functionality, alternatively an azocyclohydrocarbon, a primary, secondary, or tertiary amine, or tertiary amine hydrochloride catalyst, alternatively an azocyclohydrocarbon, a tertiary amine, or tertiary amine hydrochloride catalyst, alternatively a diazobicyclo-(Ci- io)alkane, a tertiary amine, or a tertiary amine hydrochloride.
[0014] Examples of the amine-type rearrangement catalyst include, but are not limited to, l,4-diazabicyclo[2.2.2]octane, l,4-diazabicyclo[2.2.2]pentane, and 1,4- diazabicyclo[2.2.2]propane, triethylamine, trimethylamine, triethylamine hydrochloride, trimethylamine hydrochloride, tributylamine. Amine-type rearrangement catalysts are known and available commercially.
[0015] In one embodiment, the rearrangement catalyst is a cyclic ether, alternatively tetrahydrofuran.
[0016] The phosphonium-type rearrangement catalyst is a rearrangement catalyst comprising a phosphonium group, alternatively a tetra-hydrocarbyl phosphonium halide, alternatively a tetra-alkyl phosphonium halide, where the alkyl has from 1 to 10 carbon atoms, alternatively 1 to 6 carbon atoms, alternatively 2 to 6 carbon atoms, and where the halide is chloride, bromide or iodide, alternatively chloride.
[0017] Examples of the phosphonium type rearrangement catalyst include, but are not limited to, tetra-n-butyl phosphonium chloride, tetra-isopropyl phosphonium chloride, tetra- n-pentyl phosphonium chloride, tetra-hexyl phosphonium chloride, tetra-benzyl phosphonium chloride. Most of the phosphonium catalysts can be purchased or made using known processes.
[0018] The silane and siloxane mixture comprises a halodisilane and a halodisiloxane.
[0019] The halodisilane is according to the formula R1 aR2bSi2, wherein R1 is halogen, alternatively bromo, chloro, or iodo, alternatively chloro, R2 is H, and a is an integer from 1 to 6, alternatively 4 to 6, alternatively individually 4, 5, or 6, and b is an integer from 0 to 5, alternatively 0 to 2, alternatively individually 0, 1, or 2.
[0020] Examples of the halodisilane include, but are not limited to, hexachlorodisilane, pentachlorodisilane, and tetrachlorodisilane.
[0021] The halodisoloxane is according to the formula R3 cR4dSi-0-SiR5 eR6f, where R3 and R5 are halogen, alternatively bromo, chloro, or iodo, alternatively chloro, R4 and R6 are H, each c, d, e, and f individually are an integer from 0 to 3, c+e is an integer froml to 6, alternatively 3 to 6, and d+f is an integer from 0 to 5, alternatively 0 to 3.
[0022] Examples of the halodisiloxane include, but are not limited to, hexachlorodisiloxane, pentachlorodisiloxane, and tetrachlorodisiloxane.
[0023] The solvent is any solvent that will solubilize and not react with the silanes and siloxanes in the reaction mixture.
[0024] In one embodiment, the solvent has a boiling point, alternatively the solvent has a boiling point that is greater than the boiling point of the halodisiloxane, alternatively > 5 °C more than the boiling point of the halodisiloxane, alternatively > 10 °C more than the boiling point of the halodisiloxane.
[0025] Examples of the solvent include, but are not limited to, diisopropyl benzene, hexane, heptane, decane, dodecane, xylene, toluene, tetrahydrofuran (THF), and tetraethyleneglycol dimethyl ether. These solvents are available commercially.
[0026] The silane and siloxane mixture may also comprise monosilanes and/or polysilanes in addition to the halodisilane and the halodisiloxane, alternatively the silane and siloxane comprises at least one silane or siloxane in addition to the halodisilane and the halodisiloxane.
[0027] The silane and siloxane mixture may comprises any ratio and percentage of halodisilane and halodisiloxane, alternatively the silane and siloxane mixture comprises from 1 to 97% (w/w), alternatively from 3 to 75% (w/w), alternatively from 3 to 50% (w/w), based on the weight of the disilane, disiloxane, mono- and polysilanes, and solvent present in the mixture, of halodisilane, halodisiloxane, or halodisilane and halodisiloxane.
[0028] The silane and siloxane mixture may be formed in processes to make trichlorosilane or polysilicon. For example, trichlorosilane is produced by the reaction of HC1 with silicon metal, where the halodisiloxane is produced by reaction with any moisture present, or trichlorosilane is produced through the reaction of silicon metal, silicon tetrachloride and hydrogen. However, the silane and siloxane mixture can be produced by other processes. One skilled in the art would know how to produce the mixture of the invention.
[0029] The reaction mixture is formed by combining the rearrangement catalyst, the silane and siloxane mixture, and solvent, if present. The rearrangement catalyst, the silane and siloxane mixture, and solvent, if present can be combined in any order. In one embodiment, solvent is added to the rearrangement catalyst to form a rearrangement and catalyst mixture. The rearrangement and catalyst mixture is then added to the silane and siloxane mixture or the silane and siloxane mixture is then added to the rearrangement and solvent mixture. The silane and siloxane mixture may also be combined with solvent prior to combining with the rearrangement catalyst or the rearrangement catalyst and solvent mixture. One skilled in the art would know how to combine the rearrangement catalyst and the silane and siloxane mixture and solvent, if present.
[0030] There is no particular rate of addition for the silane and siloxane mixture with the rearrangement catalyst or with the solvent, alternatively the silane and siloxane mixture is combined with the rearrangement catalyst over 2 seconds to 8 hours, alternatively from 10 minutes to 2 hours. The temperature of the silane and siloxane mixture, rearrangement catalyst, and solvent, if present, may be combined at any practical temperature, alternatively combined at a temperature below 10 °C and then the temperature raised to affect the rearrangement of the halodisilane. One skilled in the art would know the temperatures to maintain for the rearrangement reaction and these are described below.
[0031] The concentration of rearrangement catalyst combined in the reaction mixture is in the range 0.005 to 5% (w/w), alternately 0.007 to 0.2% (w/w), based on the weight of the rearrangement catalyst and silane and siloxane mixture in the reaction mixture.
[0032] Conditions sufficient to cause the rearrangement of the halodisilane are a temperature from 0 to 200 °C, alternatively from 20 to 150 °C, a pressure from sub-atmospheric pressure to super-atmospheric pressure, alternatively from full vacuum to 1480.3 kPa, for 2 minutes to 24 hours, alternatively from 20 minutes to 5 hours. In one embodiment, the silane and siloxane mixture is combined with the catalyst and any solvent at a temperature from -10 °C to 10 °C and then is heated. One skilled in the art would know how to achieve the temperature and pressure conditions for a rearrangement reaction. For example, the reaction mixture may be heated using a heating mantle or a steam jacket and using a pressure reactor.
[0033] The reaction product mixture comprises two or more halodisilane rearrangement products and the halodisiloxane. The halodisilane rearrangement products are far boiling. "Far boiling" is intended to mean that the boiling point is at least 5 °C, alternatively at least 10 °C, alternatively at least 15 °C different than the boiling point of the halodisiloxane. "Different" in the context of the boiling point of the rearrangement products can be either greater than or less than the boiling point of the halodisiloxane. In one embodiment, the halodisilane rearrangement products contain one or more silanes, alternatively partially or fully chlorinated neopentasilane, that will boil at temperatures greater than the boiling point of the halodisiloxane, and one or more silanes, alternatively silicontetrachloride, trichlorosilane, and/or dichlorosilane that boils at temperatures less than the boiling point of the halodisiloxane.
[0034] In one embodiment, the two or more halodisilane rearrangement products include, but are not limited to, perchloroneopentasilane and trichlorosilane. Additional rearrangement products may also be present.
[0035] The halodisiloxane in the reaction product mixture is as described above for the halodisilane and halodisiloxane mixture.
[0036] The rearrangement is carried out in reactors suitable for rearrangement reactions of silanes. One skilled in the art would know reactors that would be suitable for rearrangement reactions. For example, the rearrangement may be carried out in a round bottom flask, a sealed tube reactor, or a Parr reactor.
[0037] The method may further comprise recovering the halodisiloxane from the reaction product mixture, alternatively recovering the halodisiloxane from the reaction product mixture by, stripping, single stage stripping, chromatography, or distillation, alternatively removing the monosilane having a boiling point that is at least 10 °C < the boiling point of the halodisilane from the reaction product mixture and then the halodisiloxane by stripping, alternatively distillation.
[0038] One skilled in the art would know the equipment, conditions, and procedures for stripping, single stage stripping, chromatography, and distillation to recover the halodisiloxane.
[0039] A method of separating a halodisiloxane from a mixture, the method comprising: subjecting a reaction mixture comprising
a rearrangement effective amount of a rearrangement catalyst,
a silane and siloxane mixture, wherein the silane and siloxane mixture comprises a halodisilane and a halodisiloxane, and
optionally, a solvent,
to conditions sufficient to cause the rearrangement of the halodisilane to produce a reaction product mixture, wherein the reaction product mixture comprises two or more halodisilane rearrangement products and the halodisiloxane, and
recovering the halodisiloxane.
[0040] The reaction mixture, rearrangement catalyst, silane and siloxane mixture, halodisilane, halodisiloxane, solvent, conditions, reaction product mixture, halodisiloxane rearrangement products are as described above for the method of producing a mixture of silanes and siloxane.
[0041] The halodisiloxane is recovered by single stage stripping, distillation or
chromatography, alternatively distillation, alternatively vacuum distillation. One skilled in the art would know how to distill the halodisiloxane including the equipment and conditions.
[0042] The present invention rearranges halodisilanes in a mixture of halodisilane and halodisiloxanes, where the halodisilanes are close boiling to the siloxanes, to produce a mixture of silanes and siloxanes, where the silane rearrangement products are far boiling from the halodisiloxane, thereby allowing the halodisiloxanes to be easily recovered from the mixture of silanes and siloxanes by, for example, distillation. The present invention also recovers the halodisiloxane from the mixture of the rearrangement products.
EXAMPLES
[0043] The following examples are presented to better illustrate the method of the present invention, but are not to be considered as limiting the invention, which is delineated in the appended claims. Unless otherwise noted, all parts and percentages reported in the examples are by weight. The following table describes the abbreviations used in the examples:
Table 2. List of abbreviations used in the examples.
Abbreviation Word
g gram
Me methyl
wt weight
% percent
mol mole
hr hour
°C °C
NA Not Applicable
mL milliliters
Solids Content (wt. of dried sample/wt. of initial sample) x 100
and determined as described below
cm Centimeter
HCDS Hexachlorodisilane
PCDS Pentachlorodisilane
4CDS Tetrachlorodisilane
5CDSO Pentachlorodisiloxane
4CDSO Tetrachlorodisiloxane
6CDS Hexachlorodisiloxane
DIPB Diisopropylbenzene
DABCO l,4-diazabicyclo[2.2.2]octane
psia Pounds per square inch absolute
mmHg Millimeters of mercury absolute
KG, Kg, or kg kilogram
Test Procedure:
EXAMPLE 1
[0044] A mixed chlorosiloxane and chlorodisilane composition consisting of 8.7% HCDS, 56.0% HCDSO, 27.3% PCDS, 0.01% 4CDS, 2.9% 5CDSO, 0.03% 4CDSO, along with minor low and high boiling siloxanes and silanes was purified to chlorosiloxanes by using the following method. 13 kg of diisopropylbenzene (DIPB) was loaded to a 50L agitated reaction vessel. The reactor was agitated at 200 RPM. The reactor temperature was initially set to 0°C. 2 grams of DABCO was mixed with 40 grams of DIPB to dissolve the catalyst. This catalyst solution was poured into the reactor vessel. The catalyst bottle was then rinsed twice with 250 ml of DIPB and poured to the reactor also. 21.78 kg of the siloxane/silane mixture was fed to the reactor at ambient pressure. After feed was complete, the reactor was held for one hour at 0°C. The reactor was then ramped to 64.5 °C over four hours at ambient pressure. The reactor was then continued to be ramped to 124 °C while slowly ramping down pressure to 66.65 kPa. During this time the volatile silanes were condensed and collected in an overhead receiver. When the overhead distillate reached 2.5% 6CDSO, the overhead was switched to product collection. The product was then stripped until the final pot temperature was 137 °C and the pressure was 14.67 kPa. This final product composition was characterized by GC to comprise 0.01% HCDS, 97.5% 6CDSO, 0.01% 5CDS, 1.1% DIPB along with other minor high and low boiling silanes and siloxanes.
[0045] The same procedure as above was repeated and resulted in a final composition by GC of 0.28% HCDS, 98.3% 6CDSO, 0% 5CDS, 0.02% DIPB, along with other minor high and low boiling silanes and siloxanes.
[0046] The two compositions in the above examples were mixed and loaded to a batch distillation vessel. 18 KG of the material was distilled between 20.7 - 89.6 kPa with a maximum reboiler temperature of 111 °C. The material was distilled to higher purity using a reflux ratio of 30. The final product yielded 7 KG of high purity chlorosiloxane containing 99.18% HCDSO, 0.01% 5CDS, 0.06% 5CDSO, 0.56% HCDS, and 0.17% SiC14 as characterized by GC.
Claims
1. A method of producing a mixture of silanes and siloxane, the method comprising: subjecting a reaction mixture comprising
a rearrangement effective amount of a rearrangement catalyst,
a silane and siloxane mixture, wherein the silane and siloxane mixture comprises a halodisilane and a halodisiloxane, and
optionally, a solvent,
to conditions sufficient to cause the rearrangement of the halodisilane to produce a reaction product mixture, wherein the reaction product mixture comprises two or more halodisilane rearrangement products and the halodisiloxane.
2. A method according to claim 1, wherein the rearrangement catalyst is 1,4- diazabicyclo[2.2.2]octane, tetrahydrofuran, triethyamine, trimethylamine, triethylamine hydrochloride, trimethylamine hydrochloride, tributylamine, or tetra-n-butyl phosphonium chloride.
3. A method according to claim 1 or 2, wherein the halodislane is according to the formula R1 aR2bSi2, wherein R1 is halogen, R2 is H, and a is an integer from 1 to 6, and b is an integer from 0 to 5, and wherein the halodisoloxane is according to the formula
R3cR4dSi-0-SiR5 eR6f, where R3 and R5 are halogen, R4 and R6 are H, c, d, e, and f are an integer from 0 to 3, c+e is an integer from 1 to 6, and d+f is an integer from 0 to 5.
4. A method according to any one of the preceding claims, wherein the reaction mixture comprises the solvent, and the solvent has a boiling point that is sufficiently > the boiling point of the halodisiloxane to allow for separation of the halodisiloxane from the reaction product mixture.
5. A method according to claim 4, wherein the solvent has a boiling point that is at least 5 °C > the boiling point of the halodisiloxane, the temperature is from 0 to 200 °C.
6. A method according to any one of the preceding claims wherein the solvent is diisopropylbenzene.
7. A method according to any one of the preceding claims, wherein the halodisilane rearrangement products comprise a monosilane having a boiling point that is at least 10 °C < the boiling of the halodisilane and a polysilane having a boiling point that is at least 10 °C > the boiling than the halodisilane.
8. A method according to claim 7, further comprising first removing the monosilane having a boiling point that is at least 10 °C < the boiling point of the halodisilane from the reaction product mixture and then the halodisiloxane by single stage stripping.
9. A method of separating a halodisiloxane from a mixture, the method comprising: subjecting a reaction mixture comprising
a rearrangement effective amount of a rearrangement catalyst,
a silane and siloxane mixture, wherein the silane and siloxane mixture comprises a halodisilane and a halodisiloxane, and
optionally, a solvent,
to conditions sufficient to cause the rearrangement of the halodisilane to produce a reaction product mixture, wherein the reaction product mixture comprises two or more halodisilane rearrangement products and the halodisiloxane, and
recovering the halodisiloxane.
10. A method according to claim 9, wherein the halodisiloxane is recovered by distillation.
11. A method according to claim 9 or 10,
wherein the halodislane is according to the formula R1 aR2bSi2, wherein R1 is halogen, R2 is H, and a is an integer from 1 to 6, and b is an integer from 0 to 5, and wherein the halodisoloxane is according to the formula
R3cR4dSi-0-SiR5 eR6f, where R3 and R5 are halogen, R4 and R6 are H, c, d, e, and f are an integer from 0 to 3, c+e is an integer froml to 6, and d+f is an integer from 0 to 5,
wherein the halodisilane rearrangement products comprise a monosilane having a boiling point that is at least 10 °C < the boiling than the halodisilane and a polysilane having a boiling point that is at least 10 °C > the boiling than the halodisilane,
wherein the reaction mixture comprises the solvent, and the solvent has a boiling point that is sufficiently > the boiling point of the halodisiloxane to allow for separation of the halodisiloxane from the reaction product mixture, and
wherein the rearrangement catalyst is l,4-diazabicyclo[2.2.2]octane.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762538243P | 2017-07-28 | 2017-07-28 | |
| US62/538,243 | 2017-07-28 |
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| WO2019022878A1 true WO2019022878A1 (en) | 2019-01-31 |
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| PCT/US2018/039010 WO2019022878A1 (en) | 2017-07-28 | 2018-06-22 | Method of making a mixture of far boiling silane and siloxane |
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| WO (1) | WO2019022878A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020205356A1 (en) * | 2019-03-29 | 2020-10-08 | Momentive Performance Materials Inc. | Low temperature process for the safe conversion of the siemens process side-product mixture to chloromonosilanes |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008097435A1 (en) * | 2007-02-06 | 2008-08-14 | Dow Corning Corporation | Silicone resin, silicone composition, coated substrate, and reinforced silicone resin film |
| WO2013101618A1 (en) * | 2011-12-30 | 2013-07-04 | Momentive Performance Materials Inc. | Synthesis of organohalosilane monomers via enhanced cleavage of direct process residue |
-
2018
- 2018-06-22 WO PCT/US2018/039010 patent/WO2019022878A1/en active Application Filing
- 2018-07-25 TW TW107125633A patent/TW201910261A/en unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008097435A1 (en) * | 2007-02-06 | 2008-08-14 | Dow Corning Corporation | Silicone resin, silicone composition, coated substrate, and reinforced silicone resin film |
| WO2013101618A1 (en) * | 2011-12-30 | 2013-07-04 | Momentive Performance Materials Inc. | Synthesis of organohalosilane monomers via enhanced cleavage of direct process residue |
Non-Patent Citations (1)
| Title |
|---|
| COOPER, GLENN D.; GILBERT, ALFRED R: "Cleavage and disproportionation of polychlorodisilanes, trichloromethylchlorosilanes, and hexachlorodisiloxane by amines and ammonium salts", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 82, 1 October 1960 (1960-10-01), pages 5042 - 5044, XP002783949, ISSN: 0002-7863 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020205356A1 (en) * | 2019-03-29 | 2020-10-08 | Momentive Performance Materials Inc. | Low temperature process for the safe conversion of the siemens process side-product mixture to chloromonosilanes |
| CN113891856A (en) * | 2019-03-29 | 2022-01-04 | 迈图高新材料公司 | Low temperature process for the safe conversion of a mixture of siemens process by-products to chloromonosilane |
| US20220169520A1 (en) * | 2019-03-29 | 2022-06-02 | Momentive Performance Materials Inc. | Low temperature process for the safe conversion of the siemens process side-product mixture to chloromonosilanes |
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| TW201910261A (en) | 2019-03-16 |
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