WO2014023470A1 - Verfahren zur gekoppelten herstellung von polysilazanen und trisilylamin - Google Patents
Verfahren zur gekoppelten herstellung von polysilazanen und trisilylamin Download PDFInfo
- Publication number
- WO2014023470A1 WO2014023470A1 PCT/EP2013/063286 EP2013063286W WO2014023470A1 WO 2014023470 A1 WO2014023470 A1 WO 2014023470A1 EP 2013063286 W EP2013063286 W EP 2013063286W WO 2014023470 A1 WO2014023470 A1 WO 2014023470A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- reactor
- ammonia
- solvent
- polysilazanes
- tsa
- Prior art date
Links
- 0 *N(*NS=*)*N(*)*(N(*)C=*)=C Chemical compound *N(*NS=*)*N(*)*(N(*)C=*)=C 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B21/00—Nitrogen; Compounds thereof
- C01B21/082—Compounds containing nitrogen and non-metals and optionally metals
- C01B21/087—Compounds containing nitrogen and non-metals and optionally metals containing one or more hydrogen 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
- C08G77/60—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 in which all the silicon atoms are connected by linkages other than oxygen atoms
- C08G77/62—Nitrogen atoms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/24—Stationary reactors without moving elements inside
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/24—Stationary reactors without moving elements inside
Definitions
- the present invention relates to a process for the preparation of trisilylamine
- Ammonia first metered substoichiometrically against monochlorosilane, which is also present in an inert solvent.
- the reaction is carried out in a reactor in which, in addition to trisilylamine, polysilazanes are formed.
- the reactor is subsequently expanded and TSA is separated from the product mixture in gaseous form.
- the resulting TSA is purified by filtration and distillation and obtained in high or highest purity.
- ammonia dissolved in inert solvent is further metered into the reactor, wherein a stoichiometric excess of ammonia is used together with the previously introduced amount of ammonia in relation to the previously present amount of MCS. Excess ammonia is then vented, inert gas introduced, and the bottoms product mixture from the reactor passed through a filter unit to separate solid ammonium chloride to obtain a liquid mixture of polysilazanes and solvent.
- Polysilazanes are polymers with a basic structure of silicon and nitrogen atoms in alternating order. An overview can be found, for example
- each silicon atom is attached to two nitrogen atoms, or each
- R 1, R 2 and R 3 may be hydrogen atoms or organic radical groups. If only hydrogen atoms as
- Substituents are present, called the polymers as perhydropolysilazanes [H 2 Si-NH] n . If hydrocarbon radicals are bonded to silicon and / or nitrogen, this is referred to as organopolysilazanes. Polysilazanes are colorless to yellow liquids or solids, going from oily to waxy to glassy, with a density of about 1 kg / l. The average molecular weight can be from a few hundred to more than 100,000 g / mol. Both molecular mass and molecular Macrostructure determine the state of matter and the viscosity. At a molecular weight above 10,000 g / mol, the melting point is 90-140 ° C. High molecular weight perhydropolysilazane [(SiH 2 ) NH] x is a siliceous white substance. Polysilazanes age slowly with elimination of H 2 and / or NH 3 .
- Smaller molecules can be converted to larger molecules by thermal treatment. At temperatures of 100 to 300 ° C, crosslinking of the molecules takes place with elimination of hydrogen and ammonia.
- Polysilazanes are used as a coating material and as an ingredient of
- High temperature paints of corrosion protection systems Since these are also good insulators, they are used in the electronics and solar industries. In the ceramics industry, these are used as preceramic polymers. Furthermore, polysilazanes are used for high-performance coating of steel for protection against oxidation. They are sold commercially as a 20% by weight solution.
- the preparation of polysilazanes can be carried out from chlorosilanes or hydrocarbon-substituted chlorosilanes and ammonia or hydrocarbon-substituted amines (in addition to ammonia and amines, the reaction can also be carried out with hydrazine).
- the reaction can also be carried out with hydrazine.
- ammonium chloride or hydrocarbon substituted amino chlorides which must be separated.
- the reactions are basically spontaneous, exothermic reactions.
- the above-mentioned synthetic routes can be carried out using a solvent.
- Another possibility is to dose halosilane in liquid ammonia, as provided by the application WO 2004/035475.
- halosilane in liquid ammonia, as provided by the application WO 2004/035475.
- the separation of the ammonium halide can be facilitated by the polysilazanes, because the ammonium halide dissolves in the ammonia, while the polysilazanes form a second liquid phase.
- the liquids can be separated by a phase separation.
- TSA is an easily mobile, colorless and easily hydrolysable liquid with a melting point of -105.6 ° C and a boiling point of + 52 ° C.
- TSA like other nitrogen-containing silicon compounds, are important substances in the semiconductor industry.
- TSA for the production of silicon nitride layers, described e.g. in the specifications US 4,200,666 and JP 1986-96741.
- TSA finds particular use in chip fabrication as a layer precursor for silicon nitride or silicon
- the reactor is subsequently expanded and TSA is separated from the product mixture in gaseous form.
- the resulting TSA is purified by cryogenic filtration and distillation and is obtained in high or highest purity. Subsequently, another in inert
- Solvent dissolved ammonia dosed into the reactor which is used together with the previously introduced amount of ammonia over the previously present amount of MCS, a stoichiometric excess of ammonia. Excess ammonia is then drained, inert gas introduced, and the bottom product mixture from the
- Cold reactor passed through a filter unit, wherein solid ammonium chloride is separated, and to obtain a liquid mixture of polysilazanes and solvent.
- the invention thus relates to a process for the preparation of trisilylamine and
- Filtration unit (3) in the distillation column (4) leads, in which one separates TSA overhead from the solvent (L), and
- step (c) the reactor is depressurized in a manner known to those skilled in the art by opening a valve above the liquid in the reactor.
- step (b) The introduction of ammonia in step (b) is also called initial dosage in the context of the invention.
- the stoichiometric excess of the ammonia (NH 3 ) introduced into the reactor (1) in the solvent (L) in the solvent (L) is preferably chosen to be from 2 to 5 mol%.
- the product mixture obtained during the reaction in the reactor (1) during step (b) contains ammonium chloride (NH 4 Cl).
- the inert solvent (L) used in the process according to the invention is
- ammonium halides are particularly preferred Ammonium chloride are insoluble therein.
- an inert solvent which contains neither an azeotrope with TSA nor with those obtained during the performance of the process according to the invention
- the inert solvent should preferably be less volatile than TSA.
- Such preferred solvents may be selected from pyridine, tetrahydrofuran, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, toluene, xylene and / or dibutyl ether.
- TSA is stable in toluene.
- ammonium chloride is sparingly soluble in toluene, which facilitates the separation of ammonium chloride by filtration. This has already been described in the earlier patent application DE 10 201 1088814.4, the disclosure content of which is expressly included in the scope of the present invention.
- Polysilazanes are also stable in toluene.
- toluene is used to dilute the reactor solution and to record the reaction enthalpy.
- a volume ratio of the liquids solvent to monochlorosilane from 30: 1 to 1: 1, preferably from 20: 1 to 3: 1, more preferably from 10: 1 to 3: 1 set.
- This excess causes a strong dilution of monochlorosilane, and this in turn increases the yield of TSA.
- Another advantage of using L in a volumetric excess of monochlorosilane (MCS) is that the concentration of ammonium chloride in the reaction solution is reduced, thereby facilitating reactor agitation and depletion. Excessive excesses, eg above 30: 1, however, worsen the space-time yield in the reactor.
- the reaction of the reaction mixture in the reactor at a temperature of -60 to +40 ° C, preferably at -20 to +10 ° C, more preferably -15 to +5 ° C, most preferably -10 to 0 ° C.
- the reaction can be carried out at a pressure of 0.5 to 15 bar, in particular at the pressure which is established under the given reaction conditions.
- the resulting polysilazanes (PS) are chlorine-containing to a small extent. The majority of polysilazanes, however, is chlorine-free. Thus, they are perhydropolysilazanes.
- the reaction is preferably carried out under protective gas, for example nitrogen and / or a noble gas, preferably argon, and in the absence of oxygen and water, in particular in the absence of moisture, wherein the present system is preferably dried before the first filling operation and flushed with protective gas.
- protective gas for example nitrogen and / or a noble gas, preferably argon, and in the absence of oxygen and water, in particular in the absence of moisture, wherein the present system is preferably dried before the first filling operation and flushed with protective gas.
- step (c) the reactor is depressurized.
- the distillate obtained after step (c2) can be filtered cryogenic by means of filter unit (3), solid ammonium chloride (NH 4 Cl) being separated from the distillate, and this filtrate from the filter unit (3) into the
- Distillation column (4) leads, in which TSA is separated overhead from the solvent (L).
- the advantage is that TSA is achieved with a purity of 99.9% by weight.
- the step is carried out by means of a further filter unit and distillation unit, which is not shown in FIG.
- the polysilazanes present in the reactor (1) may contain chlorine. To these still present in the reactor polysilazanes in completely chlorine-free polysilazanes, preferably
- ammonia dissolved in L is metered in in step (c3) in order to allow chlorine, which is still slightly bound to the polysilazanes, to reactivate.
- This introduction is also called second dosing in the context of the invention.
- the preferred stoichiometric excess of ammonia compared to the originally used amount of MCS is in the range from 5 to 20 mol%.
- perhydropolysilazanes are contained, which preferably have a molecular weight of 100 to 300 g / mol.
- Product mixture may also have novel Perhydropolysilazane for which there are no CAS numbers. Exemplary structural formulas are shown in Table 1.
- step (c4) purges excess NH 3 from the reactor volume.
- Preferred inert gas is argon.
- step (c5) the bottom product mixture, which still contains perhydropolysilazanes having a molecular weight of up to 300 g / mol, toluene and ammonium chloride, is passed cold from the reactor (1) through a filter unit (5), solid ammonium chloride being separated from the product mixture ,
- the advantage associated with the use of MCS in step (a) is that the filtration of ammonium chloride to separate from the perhydropolysilazanes with a molecular weight of up to 300 g / mol is easily possible. A filtration of
- Ammonium chloride for the separation of polysilazanes with significantly higher molecular weights would not be completely successful, but is unnecessary in the process according to the invention, since polysilazanes with significantly higher molecular weights than 300 g / mol arise only if Dichlorosilane and / or trichlorosilane instead of or in addition to MCS in step (a) would be submitted.
- the solvent can be evaporated off from the mixture of polysilazanes and solvent by distillation in order to increase the proportion of polysilazanes in the mixture.
- the concentrated solution by any solvent preferably dibutyl ether
- the concentrated solution by any solvent resume and thus adjust a concentration that is adapted to commercial needs.
- a 2% strength by weight solution can be increased to 10% by weight and then diluted again to 5% by weight using dibutyl ether.
- concentration of the polysilazanes obtained according to the invention can be adjusted in a targeted manner, for example after an inaccurate distillation.
- the process according to the invention can be carried out batchwise or continuously. If the process is carried out continuously, it is advantageous to use recirculation possibilities of components known to the person skilled in the art.
- the invention likewise provides a system for the reaction of at least the reactants monochlorosilane (MCS) in a solvent (L) and ammonia in the liquid phase to form a product mixture comprising trisilylamine and polysilazanes
- MCS monochlorosilane
- L solvent
- ammonia in the liquid phase
- a filter unit (3) is equipped, the at least one
- a downstream filter unit (5) opens, at least one
- Filtrates consisting of polysilazanes and solvents.
- the plant according to the invention provides TSA and polysilazanes in a highly pure quality. If, in the process according to the invention, the distillate obtained after step (c2) is filtered repeatedly cryogenic by means of a filter unit and repeatedly distilled by means of a distillation column, then the plant according to the invention can be equipped with a further filter unit and another
- FIG. 1 The system according to the invention is shown schematically in FIG.
- the reference symbols mean
- the plant parts according to the invention which come into contact with the substances used according to the invention are preferably made of stainless steel and can be cooled or heated in a controlled manner.
- TSA Distillation unit was distilled off of 133 g TSA with portions of toluene and small amounts of ammonium chloride. By filtration and subsequent distillation, TSA was first obtained, which was then again filtered through the same apparatuses (3) and (4) and distilled to obtain TSA with a purity of 99.9 wt .-%.
- TSA Ammonium chloride.
- TSA was first obtained, which was then again filtered or distilled through (3) and (4), whereby TSA was obtained with a purity of 99.9 wt .-%.
- a dosage of 16 g of ammonia in a toluene feed of 180 ml / h was carried out for 0.5 h in the reactor. Temperature and pressure remained constant during dosing. Subsequently, excess ammonia was discharged from the reactor and inert gas introduced into the reactor.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Silicon Polymers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201380042453.4A CN104520353A (zh) | 2012-08-10 | 2013-06-25 | 聚硅氮烷和三甲硅烷基胺的联合制备方法 |
EP13730908.4A EP2882797A1 (de) | 2012-08-10 | 2013-06-25 | Verfahren zur gekoppelten herstellung von polysilazanen und trisilylamin |
JP2015525790A JP2015530964A (ja) | 2012-08-10 | 2013-06-25 | ポリシラザン及びトリシリルアミンの複合的な製造方法 |
US14/344,801 US20150147256A1 (en) | 2012-08-10 | 2013-06-25 | Process for the coupled preparation of polysilazanes and trisilylamine |
KR1020157003121A KR20150042196A (ko) | 2012-08-10 | 2013-06-25 | 폴리실라잔 및 트리실릴아민의 조합 제조 방법 |
US14/212,191 US20140341794A1 (en) | 2012-08-10 | 2014-03-14 | Process for the coupled preparation of polysilazanes and trisilylamine |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102012214290.8 | 2012-08-10 | ||
DE102012214290.8A DE102012214290A1 (de) | 2012-08-10 | 2012-08-10 | Verfahren zur gekoppelten Herstellung von Polysilazanen und Trisilylamin |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US14/344,801 A-371-Of-International US20150147256A1 (en) | 2012-08-10 | 2013-06-25 | Process for the coupled preparation of polysilazanes and trisilylamine |
US14/212,191 Continuation US20140341794A1 (en) | 2012-08-10 | 2014-03-14 | Process for the coupled preparation of polysilazanes and trisilylamine |
Publications (1)
Publication Number | Publication Date |
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WO2014023470A1 true WO2014023470A1 (de) | 2014-02-13 |
Family
ID=48672647
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2013/063286 WO2014023470A1 (de) | 2012-08-10 | 2013-06-25 | Verfahren zur gekoppelten herstellung von polysilazanen und trisilylamin |
Country Status (8)
Country | Link |
---|---|
US (1) | US20150147256A1 (de) |
EP (1) | EP2882797A1 (de) |
JP (1) | JP2015530964A (de) |
KR (1) | KR20150042196A (de) |
CN (1) | CN104520353A (de) |
DE (1) | DE102012214290A1 (de) |
TW (1) | TW201422687A (de) |
WO (1) | WO2014023470A1 (de) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014181194A3 (en) * | 2013-03-28 | 2015-03-26 | L'air Liquide Societe Anonyme Pour I'etude Et L'exploitation Des Procedes Georges Claude | Apparatus and method for the condensed phase production of trisilylamine |
WO2015135698A1 (de) * | 2014-03-14 | 2015-09-17 | Evonik Degussa Gmbh | Verfahren zur herstellung von reinem trisilylamin |
US9446954B2 (en) | 2013-05-27 | 2016-09-20 | Evonik Degussa Gmbh | Process for the coupled preparation of trisilylamine and polysilazanes having a molar mass of up to 500 g/mol |
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SG11201703195QA (en) * | 2014-10-24 | 2017-05-30 | Versum Materials Us Llc | Compositions and methods using same for deposition of silicon-containing film |
EP3026015A1 (de) | 2014-11-28 | 2016-06-01 | Evonik Degussa GmbH | Verfahren zur herstellung von silicium hohlkörpern |
US10647578B2 (en) * | 2016-12-11 | 2020-05-12 | L'Air Liquide, Société Anonyme pour l'Etude et l'Exploitation des Procédés Georges Claude | N—H free and SI-rich per-hydridopolysilzane compositions, their synthesis, and applications |
CN107159058A (zh) * | 2017-06-29 | 2017-09-15 | 新疆科力新技术发展股份有限公司 | 自动化高温高压反应装置及气化和非气化合成的方法 |
CN108147378B (zh) * | 2018-02-07 | 2019-08-20 | 浙江博瑞电子科技有限公司 | 一种三甲基硅烷基胺的精制方法 |
TWI793262B (zh) * | 2018-02-21 | 2023-02-21 | 法商液態空氣喬治斯克勞帝方法研究開發股份有限公司 | 全氫聚矽氮烷組成物和用於使用其形成氮化物膜之方法 |
US20210317272A1 (en) * | 2018-07-24 | 2021-10-14 | A/G Innovation Partners, Ltd. | A system and method for a semi-continuous process for producing polysilazanes |
CN113912029B (zh) * | 2021-10-18 | 2023-02-21 | 浙江博瑞电子科技有限公司 | 一种超低温制备三甲硅烷基胺的方法 |
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- 2013-06-25 CN CN201380042453.4A patent/CN104520353A/zh active Pending
- 2013-06-25 KR KR1020157003121A patent/KR20150042196A/ko not_active Application Discontinuation
- 2013-06-25 WO PCT/EP2013/063286 patent/WO2014023470A1/de active Application Filing
- 2013-06-25 EP EP13730908.4A patent/EP2882797A1/de not_active Withdrawn
- 2013-08-07 TW TW102128304A patent/TW201422687A/zh unknown
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014181194A3 (en) * | 2013-03-28 | 2015-03-26 | L'air Liquide Societe Anonyme Pour I'etude Et L'exploitation Des Procedes Georges Claude | Apparatus and method for the condensed phase production of trisilylamine |
US9446954B2 (en) | 2013-05-27 | 2016-09-20 | Evonik Degussa Gmbh | Process for the coupled preparation of trisilylamine and polysilazanes having a molar mass of up to 500 g/mol |
WO2015135698A1 (de) * | 2014-03-14 | 2015-09-17 | Evonik Degussa Gmbh | Verfahren zur herstellung von reinem trisilylamin |
CN106659999A (zh) * | 2014-03-14 | 2017-05-10 | 赢创德固赛有限公司 | 制备纯三甲硅烷基胺的方法 |
Also Published As
Publication number | Publication date |
---|---|
EP2882797A1 (de) | 2015-06-17 |
TW201422687A (zh) | 2014-06-16 |
JP2015530964A (ja) | 2015-10-29 |
KR20150042196A (ko) | 2015-04-20 |
DE102012214290A1 (de) | 2014-02-13 |
CN104520353A (zh) | 2015-04-15 |
US20150147256A1 (en) | 2015-05-28 |
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