WO2025112101A1 - Procédé de préparation permettant d'améliorer le taux de conversion dans une réduction de chlorosilane d'aryle pour préparer un aryle silane - Google Patents

Procédé de préparation permettant d'améliorer le taux de conversion dans une réduction de chlorosilane d'aryle pour préparer un aryle silane Download PDF

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Publication number
WO2025112101A1
WO2025112101A1 PCT/CN2023/137499 CN2023137499W WO2025112101A1 WO 2025112101 A1 WO2025112101 A1 WO 2025112101A1 CN 2023137499 W CN2023137499 W CN 2023137499W WO 2025112101 A1 WO2025112101 A1 WO 2025112101A1
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Prior art keywords
preparation
aromatic
reducing agent
chlorosilane
aryl
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PCT/CN2023/137499
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English (en)
Chinese (zh)
Inventor
周晓兵
徐飞
刘迪
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Nata Semiconductor Materials Co Ltd
Jiangsu Nata Opto Electronic Material Co Ltd
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Nata Semiconductor Materials Co Ltd
Jiangsu Nata Opto Electronic Material Co Ltd
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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 Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0896—Compounds with a Si-H linkage
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B33/00—Silicon; Compounds thereof
    • C01B33/04—Hydrides of silicon
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B33/00—Silicon; Compounds thereof
    • C01B33/08—Compounds containing halogen
    • C01B33/107—Halogenated silanes
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B6/00—Hydrides of metals including fully or partially hydrided metals, alloys or intermetallic compounds ; Compounds containing at least one metal-hydrogen bond, e.g. (GeH3)2S, SiH GeH; Monoborane or diborane; Addition complexes thereof
    • C01B6/04—Hydrides of alkali metals, alkaline earth metals, beryllium or magnesium; Addition complexes thereof
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B6/00—Hydrides of metals including fully or partially hydrided metals, alloys or intermetallic compounds ; Compounds containing at least one metal-hydrogen bond, e.g. (GeH3)2S, SiH GeH; Monoborane or diborane; Addition complexes thereof
    • C01B6/06—Hydrides of aluminium, gallium, indium, thallium, germanium, tin, lead, arsenic, antimony, bismuth or polonium; Monoborane; Diborane; Addition complexes thereof
    • C01B6/10—Monoborane; Diborane; Addition complexes thereof
    • C01B6/13—Addition complexes of monoborane or diborane, e.g. with phosphine, arsine or hydrazine
    • C01B6/15—Metal borohydrides; Addition complexes thereof
    • 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 Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • 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 Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/12—Organo silicon halides
    • 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 Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/20—Purification, separation
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/584—Recycling of catalysts

Definitions

  • the invention relates to the technical field of organic compound preparation, and in particular to a preparation method for improving the conversion rate of preparing aromatic silane by reducing aromatic chlorosilane.
  • Aromatic silane is an important organosilicon intermediate, which can be used as a reducing agent, a raw material for synthesizing polysilane, and a raw material for preparing diiodosilane.
  • Diiodosilane is a new silicon-based precursor material, suitable for forming silicon-containing thin films by atomic layer deposition (ALD) at a lower temperature, and can be used to produce high-end semiconductor chips.
  • Diiodosilane can be prepared by the iodination reaction of elemental iodine and phenylsilane.
  • diiodosilane requires high-purity phenylsilane, especially phenylsilane that does not contain chloride impurities, because these chlorides may contaminate diiodosilane and cause the chlorine impurity content of diiodosilane to exceed the standard. Chlorine impurities can cause many problems in semiconductor chip manufacturing, including corrosion of equipment and shortening the service life of chips.
  • Phenylsilane is traditionally prepared by reducing phenyltrichlorosilane with metal hydride, during which phenyldichlorosilane and phenylmonochlorosilane intermediates are formed. Under common production conditions, due to the steric hindrance of the benzene ring, even if an excess of metal hydride is used, these intermediates cannot be completely reduced, resulting in industrially produced phenylsilane products containing a certain amount of phenylchlorosilane impurities.
  • the object of the present invention is to provide a method for improving the reduction of aromatic chlorosilanes to prepare aromatic Preparation method of aromatic silane conversion rate.
  • the technical solution adopted by the present invention includes:
  • the present invention provides a method for improving the conversion rate of preparing aromatic silane by reducing aromatic chlorosilane, comprising:
  • Aromatic chlorosilane, a reducing agent and a phase transfer catalyst are formed into a reduction reaction system in an ether solvent;
  • the reducing agent comprises an alkali metal hydride
  • the phase transfer catalyst comprises an alkali metal borohydride
  • the beneficial effects of the present invention at least include:
  • the preparation method provided by the present invention uses alkali metal borohydride as a phase transfer catalyst to improve the reducing ability of the alkali metal hydride reducing agent, thereby improving the chemical reaction process of reducing aromatic chlorosilane to prepare aromatic silane, so that the reaction proceeds in the direction of complete reaction, significantly reducing the content of intermediate products in the final product, especially aromatic monochlorosilane, and obtaining high-purity aromatic silane with extremely low chlorine content.
  • the embodiment of the present invention provides a method for improving the conversion rate of preparing aromatic silane by reducing aromatic chlorosilane, which comprises the following steps:
  • Aromatic chlorosilane, a reducing agent and a phase transfer catalyst are formed into a reduction reaction system in an ether solvent;
  • the reducing agent comprises an alkali metal hydride
  • the phase transfer catalyst comprises an alkali metal borohydride
  • Common metal hydrides used in the reduction method including lithium hydride, generally have low solubility due to their low compatibility with solvents. Even under excess conditions, they cannot achieve the desired reduction effect, which is the main reason for the formation of phenylchlorosilane impurities.
  • the solution provided by the present invention is to use a metal hydride that has good compatibility with both the solvent and lithium hydride, such as alkali metal borohydrides such as sodium borohydride, to play the role of a phase transfer catalyst, improve the solubility and reaction activity of the main reducing agent LiH, thereby achieving the purpose of improving the reduction effect and increasing the degree of reaction, so that when the same amount of metal hydride is used, the effect of significantly reducing phenylchlorosilane impurities is achieved.
  • a metal hydride that has good compatibility with both the solvent and lithium hydride such as alkali metal borohydrides such as sodium borohydride
  • the present invention creatively adds sodium borohydride with a certain mass ratio of lithium hydride, which can improve the conversion rate of aromatic trichlorosilane during the reaction and obtain phenylsilane with higher purity.
  • the purity of aromatic silane prepared and purified in the laboratory under the same experimental conditions and the same experimental equipment can reach 99.994%, the proportion of phenyl monochlorosilane is about 0.006%, and the chlorine content in pure phenylsilane is about 15 ppm.
  • the chlorine content is greatly reduced after adding borohydride in the synthesis reaction.
  • the technical problem solved by this prior art is how to improve the reaction selectivity.
  • the role of the added borohydride catalyst is to reduce the content of lithium hydride to avoid reducing the chlorine atoms connected to the alkyl group.
  • the difference between aromatic chlorosilane and alkyl chlorosilane is that the phenyl group has a higher steric hindrance effect than the alkyl group. Therefore, it is more difficult to reduce phenyl chlorosilane than to reduce alkyl chlorosilane.
  • the above-mentioned related prior art solves the problem of reduction reaction rate and reduction reaction selectivity, which belongs to the problem of reaction kinetic rate, while the present invention solves the problem of reduction reaction degree, which belongs to the problem of reaction thermodynamic equilibrium.
  • the two are not the same technical problems.
  • the so-called improvement of reducing ability includes many situations. Promoting the rate of reduction reaction is one of the kinetic situations. Improving the reducibility of the reducing agent to improve The degree to which chemical equilibrium is changed is the thermodynamic situation involved. The two cannot be confused. Increasing the reaction rate does not necessarily mean that the chemical equilibrium has changed. It only means that equilibrium can be reached quickly.
  • the goal of the present invention is to reduce the content of the partial reduction byproduct, i.e., phenylmonochlorosilane, in the phenylsilane product, rather than selectively reducing alkyl chloride or silicon chloride.
  • the yield of alkylsilane mentioned in multiple embodiments is 100%, which is sufficient to show that due to the low steric hindrance effect of the alkyl group, after controlling the selectivity, the reaction progress can naturally reach complete and thorough.
  • the above-mentioned prior art does not actually face the technical problem of incomplete reduction of the three chlorine atoms connected to the silicon atom; and for the reduced aromatic chlorosilane of the present invention, it is impossible to achieve a 100% reduction effect (i.e., the product has a chlorine content of 0 ppm) by conventional reduction methods.
  • the above-mentioned prior art makes a statement of 100% yield, which just shows that its goal is not to solve the problem of chlorine content caused by insufficient reaction progress after the reduction reaction in the product is balanced.
  • the aromatic chlorosilane includes any one or a combination of two or more of phenyltrichlorosilane, phenyldichlorosilane, phenylmonochlorosilane, o-tolyltrichlorosilane, m-tolyltrichlorosilane, p-tolyltrichlorosilane, o-tolyldichlorosilane, m-tolyldichlorosilane, p-tolyldichlorosilane, o-tolylmonochlorosilane, m-tolylmonochlorosilane, and p-tolylmonochlorosilane, but is not limited thereto.
  • the alkali metal hydride includes any one or a combination of two or more of LiH, NaH, KH, LiAlH 4 , NaAlH 4 and KAlH 4 , but is not limited thereto.
  • the alkali metal borohydride includes any one or a combination of two or more of NaBH 4 , LiBH 4 and KBH 4 , but is not limited thereto.
  • the ether solvent is selected from a high boiling point ether solvent having a boiling point higher than 100°C of the aromatic silane, preferably in some embodiments, a high boiling point ether solvent higher than 150°C;
  • the ether solvent has a boiling point of at least 270°C.
  • the high boiling point ether solvent includes any one of tetraethylene glycol dimethyl ether, triethylene glycol dimethyl ether and diethylene glycol dibutyl ether, or a combination of two or more thereof.
  • the present invention creatively uses a high boiling point solvent, such as tetraethylene glycol dimethyl ether, as the solvent for the reduction reaction, and utilizes the boiling point difference of 155 degrees between the solvent and the aromatic silane. After the reduction reaction is completed, the high-purity phenylsilane product can be quickly separated by reduced pressure distillation.
  • a high boiling point solvent such as tetraethylene glycol dimethyl ether
  • the chlorine atom in the aromatic chlorosilane reacts with the hydrogen atom in the reducing agent.
  • the molar ratio of the ions is (0.5-1):1;
  • the content of the phase transfer catalyst is 1-10% of the total mass of the reducing agent
  • the mass ratio of the reducing agent to the ether solvent is 1:(5-100).
  • the preparation method specifically comprises the following steps:
  • the reducing agent, the phase transfer catalyst and the ether solvent are fully mixed and then heated to the reaction temperature to form a reaction system;
  • the reaction temperature is 80-120° C.
  • the reduction reaction time is 1-24 h.
  • the reduced pressure distillation is performed while maintaining the reaction temperature.
  • the purity of the aromatic silane obtained in the typical implementation case of the present invention is above 99.99%, the mass ratio of the intermediate product aromatic monochlorosilane is below 0.01%, and the chlorine content is below 25 ppm.
  • the present invention improves the method of reducing phenyltrichlorosilane with metal hydride.
  • a small amount of high-solubility metal hydride is used to achieve an effect similar to that of a phase transfer catalyst, thereby improving the reduction effect of the main metal hydride, thereby greatly reducing the content of phenylchlorosilane impurities in the phenylsilane product.
  • the present invention uses a high-boiling point ether solvent, the boiling point of which is at least 100 degrees higher than that of phenylsilane, so that a high-purity phenylsilane product can be quickly separated by reduced pressure distillation after the reduction reaction is completed.
  • the compounds and reagents used are conventional reagents and are commercially available; unless otherwise specified, the pressure is at normal pressure and temperature; and the analytical test methods involved include:
  • the heating temperature is maintained at 100 ⁇ 2°C, and phenylsilane is separated by reduced pressure distillation to obtain pure phenylsilane with a purity of 99.994%, which contains 0.006% phenylmonochlorosilane and a chlorine content of 15ppm.
  • the heating temperature is maintained at 100 ⁇ 2°C, and phenylsilane is separated by vacuum distillation to obtain pure phenylsilane with a purity of 99.649%, which contains 0.351% of phenylmonochlorosilane and a chlorine content of 865ppm.
  • This embodiment is substantially the same as embodiment 1, the main difference being that the content of sodium borohydride is adjusted to 1% and 10% by weight of the lithium hydride, respectively, and both can obtain phenylsilane with a chlorine content that meets the requirements.
  • This embodiment is substantially the same as embodiment 1, the main difference being that the reducing agent and the catalyst are replaced, the reducing agent is replaced with sodium hydride, and the phase transfer catalyst is replaced with potassium borohydride, and phenylsilane with a chlorine content that meets the requirements can still be obtained.
  • This embodiment is substantially the same as embodiment 1, the main difference being that p-tolyltrichlorosilane is used instead of phenyltrichlorosilane, and the obtained p-toluenesilane contains only 0.01% of p-toluenechlorosilane, and the chlorine content is 22 ppm.
  • the embodiments of the present invention have replaced various feasible aromatic chlorosilanes, reducing agents and phase transfer catalysts, all of which can achieve equivalent technical effects, significantly improve the conversion rate and significantly reduce the chlorine content.
  • the preparation method provided by the present invention uses alkali metal borohydride as a phase transfer catalyst to improve the reducing ability of the alkali metal hydride reducing agent, thereby improving the chemical reaction process of reducing aromatic chlorosilane to prepare aromatic silane, thereby allowing the reaction to proceed in the direction of a complete reaction, significantly reducing the content of intermediates in the final product, especially aromatic monochlorosilane, and being able to obtain high-purity aromatic silane with extremely low chlorine content.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Life Sciences & Earth Sciences (AREA)
  • Geology (AREA)

Abstract

L'invention concerne un procédé de préparation permettant d'améliorer le taux de conversion dans une réduction de chlorosilane d'aryle pour préparer un arylsilane, qui comprend les étapes consistant à : former un système de réaction de réduction d'aryle chlorosilane, un agent réducteur et un catalyseur de transfert de phase dans un solvant éther, faire chauffer le système de réaction de réduction pour réagir, et réaliser une distillation sous vide de façon à obtenir un aryl silane, l'agent réducteur comprenant un hydrure de métal alcalin, et le catalyseur de transfert de phase comprenant du borohydrure de métal alcalin. Le présent procédé de préparation utilise du borohydrure de métal alcalin en tant que catalyseur de transfert de phase pour améliorer la capacité de réduction de l'agent réducteur d'hydrure de métal alcalin, et favoriser en outre la progression de la réaction chimique de réduction du chlorosilane d'aryle pour préparer un aryle silane, entraînant ainsi la réaction vers une réaction complète. Par conséquent, le procédé réduit de manière remarquable la teneur en produits intermédiaires, en particulier le monochlorosilane d'aryle, dans le produit final, ce qui permet d'obtenir un arylsilane de haute pureté ayant une teneur en chlore extrêmement faible.
PCT/CN2023/137499 2023-11-28 2023-12-08 Procédé de préparation permettant d'améliorer le taux de conversion dans une réduction de chlorosilane d'aryle pour préparer un aryle silane Pending WO2025112101A1 (fr)

Applications Claiming Priority (2)

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CN202311599850.3 2023-11-28
CN202311599850.3A CN120058769A (zh) 2023-11-28 2023-11-28 提高芳香基氯硅烷还原制备芳香基硅烷转化率的制备方法

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Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4295986A (en) * 1979-05-14 1981-10-20 Gordon Roy G Low temperature catalytic reduction
US4629801A (en) * 1985-02-04 1986-12-16 Rhone-Poulenc Specialites Chimiques Preparation of hydrogenosilanes
JP2003313190A (ja) * 2002-04-19 2003-11-06 Jsr Corp シラン類の製造方法
CN105801611A (zh) * 2014-12-31 2016-07-27 上海楚青新材料科技有限公司 制备苯基硅烷和二苯基硅烷的方法
CN108129510A (zh) * 2018-01-17 2018-06-08 中国科学院化学研究所 一种氯烷基氢硅烷的制备方法
CN108285467A (zh) * 2018-01-17 2018-07-17 中国科学院化学研究所 一种氢化钙还原氯硅烷制备氢硅烷的方法
CN108530477A (zh) * 2018-06-08 2018-09-14 中国科学院化学研究所 一种氢化锂选择性还原氯烷基氯硅烷的方法
CN114409690A (zh) * 2021-12-17 2022-04-29 苏州矽索新材料有限公司 一种使氯硅烷合成氢硅烷工艺方法
CN114656497A (zh) * 2021-12-30 2022-06-24 盘锦研峰科技有限公司 一种苯硅烷的制备方法

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4295986A (en) * 1979-05-14 1981-10-20 Gordon Roy G Low temperature catalytic reduction
US4629801A (en) * 1985-02-04 1986-12-16 Rhone-Poulenc Specialites Chimiques Preparation of hydrogenosilanes
JP2003313190A (ja) * 2002-04-19 2003-11-06 Jsr Corp シラン類の製造方法
CN105801611A (zh) * 2014-12-31 2016-07-27 上海楚青新材料科技有限公司 制备苯基硅烷和二苯基硅烷的方法
CN108129510A (zh) * 2018-01-17 2018-06-08 中国科学院化学研究所 一种氯烷基氢硅烷的制备方法
CN108285467A (zh) * 2018-01-17 2018-07-17 中国科学院化学研究所 一种氢化钙还原氯硅烷制备氢硅烷的方法
CN108530477A (zh) * 2018-06-08 2018-09-14 中国科学院化学研究所 一种氢化锂选择性还原氯烷基氯硅烷的方法
CN114409690A (zh) * 2021-12-17 2022-04-29 苏州矽索新材料有限公司 一种使氯硅烷合成氢硅烷工艺方法
CN114656497A (zh) * 2021-12-30 2022-06-24 盘锦研峰科技有限公司 一种苯硅烷的制备方法

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