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WO2015014530A1 - Procédé, dispositif et leur utilisation pour la préparation d'acryloxypropyltrialcoxysilanes et de méthacryloxypropyltrialcoxysilanes - Google Patents

Procédé, dispositif et leur utilisation pour la préparation d'acryloxypropyltrialcoxysilanes et de méthacryloxypropyltrialcoxysilanes Download PDF

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Publication number
WO2015014530A1
WO2015014530A1 PCT/EP2014/062534 EP2014062534W WO2015014530A1 WO 2015014530 A1 WO2015014530 A1 WO 2015014530A1 EP 2014062534 W EP2014062534 W EP 2014062534W WO 2015014530 A1 WO2015014530 A1 WO 2015014530A1
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WO
WIPO (PCT)
Prior art keywords
reaction
unit
mixture
temperature
rectification
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
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PCT/EP2014/062534
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German (de)
English (en)
Inventor
Hartwig Rauleder
Jaroslaw Monkiewicz
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Evonik Industries AG
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Evonik Industries AG
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Filing date
Publication date
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Priority to EP14729930.9A priority Critical patent/EP3027305A1/fr
Publication of WO2015014530A1 publication Critical patent/WO2015014530A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C07F7/1872—Preparation; Treatments not provided for in C07F7/20
    • C07F7/1876—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-C linkages
    • 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
    • B01J19/18—Stationary reactors having moving elements inside
    • 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
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • 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
    • B01J2219/00049—Controlling or regulating processes
    • B01J2219/00051—Controlling the temperature
    • B01J2219/00074—Controlling the temperature by indirect heating or cooling employing heat exchange fluids
    • B01J2219/00076—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements inside the reactor
    • 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
    • B01J2219/00049—Controlling or regulating processes
    • B01J2219/00051—Controlling the temperature
    • B01J2219/00074—Controlling the temperature by indirect heating or cooling employing heat exchange fluids
    • B01J2219/00076—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements inside the reactor
    • B01J2219/00083—Coils
    • 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
    • B01J2219/00049—Controlling or regulating processes
    • B01J2219/00051—Controlling the temperature
    • B01J2219/00074—Controlling the temperature by indirect heating or cooling employing heat exchange fluids
    • B01J2219/00087—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements outside the reactor
    • B01J2219/00101—Reflux columns
    • 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
    • B01J2219/00049—Controlling or regulating processes
    • B01J2219/00162—Controlling or regulating processes controlling the pressure

Definitions

  • the present invention relates to a special method and a device or system suitable for this purpose and their use for a particularly gentle production of acryloxy and methacryloxypropyl-trialkoxysilanes by hydrosilylation of allyl acrylate or allyl methacrylate with a Hydrogentrialkoxysilan in the presence of a homogeneous Pt catalyst system and using a stabilizer system.
  • Organic silicon compounds (organosilanes) with unsaturated organic radicals such as acryloxyalkyltrialkoxysilane or methacryloxyalkyltrialkoxysilane are important chemical
  • phase transfer catalyst cf., inter alia, EP 0 437 653 B1, EP 0 708 081 A2
  • PTC process phase transfer catalysis
  • salt process salt route
  • EP 0 708 081 A2 and EP 0 483 480 A1 disclose the use of N, N'-disubstituted p-quinonediimines and also N, N'-diphenyl-p-phenylenediamine in the "salt process" at the respective process stages in order to reduce the risk to avoid the "popcorn polymerization" of acrylic or Methacryloxypropyltrialkoxysilanen if possible. Furthermore, in said process, 2,6-di-tert-butyl-4-methylphenol (Jonol) can be used, in particular after the fractional distillation work-up for the subsequent stabilization of the product.
  • Jonol 2,6-di-tert-butyl-4-methylphenol
  • EP 0 702 016 A2 teaches acrylic or methacryloxypropyltrialkoxysilanes containing tertiary amine to raise the pH and improve storage stability.
  • EP 0 707 009 B1 discloses the hydrosilylation of an allyl ester with a hydrogen silane in the presence of a homogeneous Pt (II) catalyst.
  • a homogeneous Pt (II) catalyst As stabilizer systems, 2,6-di-tert-butylphenol and triphenylphosphane or 2,6-di-tert-butylphenol and triethylamine or phenylphosphine or 2,6-di-tert-butylphenol alone are used.
  • WO 2008/017554 A1 discloses a hydrosilylation process wherein a mixture of allylmethyl methacrylate, N, N'-diphenyl-p-phenylenediamine, 2,6-di-tert-butyl-4-methylphenol, an acetone solution of H 2 PtCl 6 x 6 H 2 O and hydrogentrimethoxysilane one
  • Preheated microreactor supplied under pressure, where reacted and worked up the product mixture by means of thin film or short path evaporator.
  • dried nitrogen which can be dried, for example, by means of a drying agent, such as silica gel or by freezing out moisture (water moisture),
  • H2PtCl 6 x6H 2 0 in the reactor which is preferably equipped with stirrer, heating or cooling including temperature measurement and control and reflux condensation, and
  • trialkoxysilane preferably hydrogentrimethoxysilane (TMOS) metered directly into the initially introduced mixture under time and temperature control, d. H. the feed for the trialkoxysilane into the reactor according to the invention is oriented below the liquid surface of the minimum filling quantity for the reaction mixture,
  • TMOS hydrogentrimethoxysilane
  • MEMO 3-methacryloxypropyltrimethoxysilane
  • the method according to the invention can advantageously be carried out in a production plant, as can be deduced from claim 1 and / or from the idealized representation according to FIG.
  • the present invention is thus an apparatus - in the present document also called production plant or plant for short - for the production of pure organosilanes with unsaturated organic radicals from the series Acryloxyalkyl- or
  • Methacryloxyalkyltrialkoxysilane by hydrosilylation comprising
  • a reaction unit (1) which is based on a reactor (stirred tank) (1) and with stirring device (2) and heating, cooling, temperature measurement and control (3) and reflux condensation (7, 8, 9) and the feeds ( 4) and (5) for feedstocks, such as inert gas, educt components and stabilizers and catalyst system, is equipped, while the feed (5) is arranged below the feed (4), so that the inlet of the feed (5.1) into the reactor (1) below the liquid surface of the later
  • a rectification unit (16) which is based on a rectification column (16) and with stirrer (17) and heating, cooling, temperature measurement and control (18) and reflux condensation (22, 23, 24) includingchtsiederauslass (25) and two Areas with column packing (19, 20) and a side stream removal (26) in the middle part of the rectification column (16) placed above the packing (19) and below the packing (20), and further with condensation unit with temperature / pressure measurement and control (27) including volatile expulsion (28), ie Constituents or components of the present phase which have a lower boiling point than the target product, are provided in the rectification column (16) above the packing (20) and a discharge device (29) for the product (30),
  • reaction unit (1) and the rectification unit (16) are for the transfer of
  • the respective units or lines of the present system may also be provided with shut-off valves at required points in addition to control systems.
  • the present invention further provides a process for the preparation of pure organosilanes having unsaturated organic radicals from the series Acryloxyalkyl- or Methacryloxyalkyltrialkoxysilan, wherein allyl acrylate or allyl methacrylate with trialkoxysilane in the presence of a homogeneous Pt (IV) catalyst and Jonol and N, N'-diphenyl reacted -p- phenylenediamine as stabilizers in a reactor and the crude product thus obtained is worked up by distillation, characterized in that
  • Hydrogentrialkoxysilane preferably in a molar ratio of 0.9 to 1: 1. It is further preferred in the process according to the invention for the two stabilizers Jonol and DPPD to be used in a molar ratio of 0.5 to 1:10.
  • the Pt (IV) catalyst is used with respect to the allyl acrylate or allyl methacrylate used in a molar ratio of Pt to allyl (meth) acrylate of 0.1 to 1: 10,000.
  • the Pt (IV) catalyst 2 is advantageously used as acetonic solution of H 2 PtCl 6 x 6 H 0, wherein the content of Pt salt in acetone, preferably 0.05 to 0.2 mole of Pt per 1 liter is acetone.
  • trialkoxysilane preferably hydrogentrimethoxysilane (TMOS)
  • TMOS hydrogentrimethoxysilane
  • Reaction mixture takes place while the reaction mixture is stirred.
  • Tnalkoxysilandos within a period of 5 to 1 15 minutes, preferably 10 to 80 minutes, more preferably 15 to 60 minutes, most preferably from 20 to 40 minutes performed.
  • the reaction mixture is allowed to react for a further 15 to 120 minutes, preferably for 20 to 80 minutes, particularly preferably for 30 to 45 minutes, at the reaction temperature after the end of the reaction with the addition of t -alkoxysilane, in order to achieve as complete a reaction as possible.
  • the reaction temperature in the (reaction) mixture is suitably adjusted by temperature control to a temperature of ⁇ 90 ° C., preferably ⁇ 80 ° C., particularly preferably to 70 to 80 ° C.
  • the pure distillation of the crude product is preferably carried out in the process according to the invention by first the crude product obtained by the reaction by means of a distillation (so-called "bridge distillation") in an overhead phase, which Acryloxalkyltrialkoxysilan-containing or Methacryloxyalkyltrialkoxysilan-containing, and a Catalyst-containing phase containing the catalyst and higher-boiling components (also called high-boiling residue), separated and the preferably taken under stirring and reduced pressure overhead of the reaction unit phase transferred to the lower part of the rectification unit and a side (current) decrease, the advantageous, as particularly gentle to the product, takes place from the middle run of the rectification column, in the pure target product, preferably pure 3-methacryloxyalkyl
  • the distillation steps are carried out in the reaction unit
  • the "bridging distillation” is preferably carried out at a bottom temperature in the reaction unit starting at about 70 ° C. increasing to 140 ° C. and a reduced pressure of 2 to 0.9 mbar, particularly preferably at about 1 mbar , wherein the head temperature for the decrease of the crude product, which is transferred to the rectification column, preferably about 75 ° C at about 1 mbar.
  • the sides (stream) decrease from the rectification column preferably at 50 ° C to 85 ° C and a reduced pressure of approx. 0.8 falling to approx. 0.5 mbar, wherein the bottom temperature in the rectification column is preferably 120 ° C to 140 ° C.
  • the rectification column used in the process according to the invention cf. also unit (16) in FIG. 1, preferably at least with stirrer (17), heating, cooling and temperature measurement and control (18), column packs (19, 20), preferably with metal Sulzer LAB-EX / Mat no .: 1.4404, column head (22, 23, 24, 25) and side take-off (26, 27, 28, 29) and connected to a unit for pressure reduction (vacuum), measurement and control (10, 21, 22).
  • a unit for pressure reduction (vacuum), measurement and control (10, 21, 22).
  • process according to the invention can be carried out continuously or batchwise.
  • FIG. 1 is a diagram in particular also FIG. 1:
  • Reaction unit (1) advantageous with stirring device (2), heating / cooling including
  • trialkoxysilane is metered directly into the charged reaction mixture, i.
  • the trialkoxysilane is metered into the liquid surface (6.1) of the reaction mixture (6) via feed (5, cf., in particular, 5.1), leaving the reaction mixture for some time,
  • the low boilers or volatile components ie, constituents of the reaction mixture or crude product, the higher Boiling point as the target product, at least partially from the thus obtained reaction or product mixture.
  • the rectification unit (16) for carrying out the purifying distillation of the crude product is suitably with stirrer (17), heating, cooling and temperature measurement and control (18), column packs (19, 20), preferably of the metal-Sulzer LAB-EX / material type. No .: 1.4404, head (22, 23, 24, 25) and side removal (26, 27, 29), arranged in the middle of the rectification column, and a connection (21, 22) to the pressure reduction unit
  • the bottoms (15.1) of the rectification column are suitably stirred and heated (17, 18), preferably under reduced pressure (10) (vacuum), and there is a side removal, cf. also the units (10, 21, 22, 15.1, 17, 18, 26, 27, 28, 29), from the middle run of the rectification column under temperature and
  • Volatile components can in this case from the unit (27) via line (28) or via the units (22, 23, 24) back into the
  • Rectification or via unit (25) and (22, 21, 10, 13) are discharged.
  • the process according to the invention can advantageously be carried out under an inert gas atmosphere for the production of MEMO, wherein the use of allyl methacrylate and TMOS as educt component is particularly preferred.
  • the mixture (6) is heated with stirring to reaction temperature (3), - Then trimethoxysilane within a defined period of time and under temperature control via supply (5) under the liquid surface (6.1) of the
  • Rectified unit (16) worked up by distillation and the product (30), pure 3-methacryloxypropyltrimethoxysilane (MEMO), via the lateral decrease (26), (27), (29) from the middle run of the rectification column (16) under temperature and Pressure control wins.
  • MEMO 3-methacryloxypropyltrimethoxysilane
  • the so-called "bridging distillation” can advantageously be carried out at a bottom temperature (6) in the reaction unit (1) starting at about 70 ° C. increasing to 140 ° C. and a reduced pressure of 2 to 0.9 mbar (1 , 8, 10), particularly preferably at about 1 mbar, wherein the head temperature (8) for taking off the crude product which is transferred to the rectification column (16, 15.1) is preferably about 75 ° C. at about 1 mbar
  • Rectification column (16) preferably at 50 ° C to 85 ° C and a reduced pressure (16, 10, 26, 27) of approx. 0.8 falling to approx. 0.5 mbar, wherein the bottom temperature (15.1) in the rectification column (16) is preferably 120 ° C to 140 ° C.
  • the process according to the invention can be carried out batchwise or continuously.
  • the subject of the present invention is the use of a system according to the invention, cf. Claim 1 and Figure 1, for the preparation of 3-methacryloxypropyltrimethoxysilane (MEMO) by hydrosilylation of allyl methacrylate with trimethoxysilane in the presence of a homogeneous Pt catalyst and a stabilizer system and distillative workup of the crude product, wherein the pure product (30) via a targeted side decrease (26 ), (27), (29), which takes place under temperature and pressure control from the rectification column (16), wins.
  • MEMO 3-methacryloxypropyltrimethoxysilane
  • the system of the invention is characterized by a largely safe and trouble-free operation.
  • MEMO produced according to the invention remains clear, in particular as part of a quality test when diluted with water, and no yellowing occurs during this process.
  • Trimethoxysilane (TMOS) (further (educt component) below the liquid surface of the mixture or of the reaction mixture introduced.)
  • the temperature of the reaction was kept at about 70-80 ° C. during the trimethoxysilane metering addition of trimethoxysilane took place over a period of 40 minutes. Thereafter, the reaction mixture was held at 75 ° C for another 45 minutes.
  • the workup was carried out under pressure and temperature control via a reaction with the part [see. Figure 1: (1), (8)] associated "bridge distillation" [see Figure 1: (1) / (10) on (7), (1 1), (12), (13) and (7), (1 1), (15) according to (16)] with subsequent purifying [see Figure 1: (16) and (22), (21), (10)] via a distillation unit with head [see FIG. (22), (23), (24), (25)] and side removal [see Figure 1: (26), (27), (28), (29)] for the pure product [see FIG. 30)].
  • the pure product 3-methacryloxypropyltrimethoxysilane (MEMO, pure) obtained by distillation has a purity of 99.3% (GC area%) according to GC analysis.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)

Abstract

La présente invention concerne un procédé particulier, un dispositif particulièrement avantageux pour celui-ci ainsi que leur utilisation pour la préparation d'organosilanes purs présentant des radicaux organiques insaturés de la série acryloxyalkyltrialcoxysilane ou méthacryloxyalkyltrialcoxysilane, en particulier de 3-méthacryloxypropyltriméthoxysilane (MEMO), par hydrosilylation d'acrylate d'allyle ou de méthacrylate d'allyle avec du trialcoxysilane en présence d'un catalyseur homogène de Pt(IV) ainsi que d'un système de stabilisant particulier et par traitement par distillation du produit brut, le produit pur étant obtenu via un soutirage latéral ciblé de la colonne de rectification qui a lieu avec régulation de la température et de la pression.
PCT/EP2014/062534 2013-07-30 2014-06-16 Procédé, dispositif et leur utilisation pour la préparation d'acryloxypropyltrialcoxysilanes et de méthacryloxypropyltrialcoxysilanes Ceased WO2015014530A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP14729930.9A EP3027305A1 (fr) 2013-07-30 2014-06-16 Procédé, dispositif et leur utilisation pour la préparation d'acryloxypropyltrialcoxysilanes et de méthacryloxypropyltrialcoxysilanes

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102013214830.5 2013-07-30
DE102013214830.5A DE102013214830A1 (de) 2013-07-30 2013-07-30 Verfahren, Vorrichtung und deren Verwendung zur Herstellung von Acryloxy- und Methacryloxypropyltrialkoxysilanen

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WO2015014530A1 true WO2015014530A1 (fr) 2015-02-05

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EP (1) EP3027305A1 (fr)
DE (1) DE102013214830A1 (fr)
WO (1) WO2015014530A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108970163A (zh) * 2018-10-09 2018-12-11 唐山三友硅业有限责任公司 高沸物精馏塔及精馏法提纯高沸物的工艺
US10894801B2 (en) 2018-07-03 2021-01-19 Evonik Operations Gmbh Process for producing alkylalkoxysilanes
US12275823B2 (en) 2021-06-30 2025-04-15 Evonik Operations Gmbh Process for producing high-purity hydrosilylation products

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114570311B (zh) * 2022-02-25 2023-05-05 浙江华亿工程设计股份有限公司 落梯分段式充气反应方法

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DE3832621C1 (fr) 1988-09-26 1989-09-21 Huels Ag, 4370 Marl, De
EP0483480A1 (fr) 1990-10-31 1992-05-06 Hüls Aktiengesellschaft Procédé pour la préparation d'organosilane contenant des groupes méthacryloxy ou acryloxy
EP0437653B1 (fr) 1987-09-25 1994-09-14 Hüls Aktiengesellschaft Procédé de préparation d'organosilanes contenant des groupes méthacryloxy ou acryloxy
EP0702016A2 (fr) 1994-08-30 1996-03-20 Hüls Aktiengesellschaft Acryloxypropylalkoxysilanes, procédé pour leur préparation et leur utilisation
DE4434200A1 (de) * 1994-09-24 1996-03-28 Huels Chemische Werke Ag Verfahren zur Herstellung von 3-Acryloxypropylalkoxysilanen
EP0708081A2 (fr) 1994-10-21 1996-04-24 Hüls Aktiengesellschaft Procédé pour la préparation de diimines de p-quinone N,N'-disubstitué, leur utilisation et organosilanes contenants des groupes méthacryloxy ou acryloxy, procédé pour leur stabilisation ainsi que leur préparation
EP1245271A2 (fr) * 2001-03-30 2002-10-02 Degussa AG Appareil et procédé pour préparer trialkoxysilanes practiquement exempts de chlore
DE10258982B3 (de) 2002-12-16 2004-08-05 Degussa Ag Verfahren zur Herstellung von Acryloxy- oder Methacryloxygruppen enthaltenden Organosilanen höchster Reinheit
WO2008017554A1 (fr) 2006-08-10 2008-02-14 Evonik Degussa Gmbh Installation, réacteur et procédé pour la fabrication industrielle continue de 3-méthacryloxypropylalcoxysilanes
DE102011004058A1 (de) * 2011-02-14 2012-08-16 Evonik Degussa Gmbh Monochlorsilan, Verfahren und Vorrichtung zu dessen Herstellung

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Publication number Priority date Publication date Assignee Title
EP0437653B1 (fr) 1987-09-25 1994-09-14 Hüls Aktiengesellschaft Procédé de préparation d'organosilanes contenant des groupes méthacryloxy ou acryloxy
DE3832621C1 (fr) 1988-09-26 1989-09-21 Huels Ag, 4370 Marl, De
EP0483480A1 (fr) 1990-10-31 1992-05-06 Hüls Aktiengesellschaft Procédé pour la préparation d'organosilane contenant des groupes méthacryloxy ou acryloxy
EP0702016A2 (fr) 1994-08-30 1996-03-20 Hüls Aktiengesellschaft Acryloxypropylalkoxysilanes, procédé pour leur préparation et leur utilisation
DE4434200A1 (de) * 1994-09-24 1996-03-28 Huels Chemische Werke Ag Verfahren zur Herstellung von 3-Acryloxypropylalkoxysilanen
EP0707009B1 (fr) 1994-09-24 2001-06-13 Degussa AG Procédé de préparation de 3-acryloxypropylalkoxysilanes
EP0708081A2 (fr) 1994-10-21 1996-04-24 Hüls Aktiengesellschaft Procédé pour la préparation de diimines de p-quinone N,N'-disubstitué, leur utilisation et organosilanes contenants des groupes méthacryloxy ou acryloxy, procédé pour leur stabilisation ainsi que leur préparation
EP1245271A2 (fr) * 2001-03-30 2002-10-02 Degussa AG Appareil et procédé pour préparer trialkoxysilanes practiquement exempts de chlore
DE10258982B3 (de) 2002-12-16 2004-08-05 Degussa Ag Verfahren zur Herstellung von Acryloxy- oder Methacryloxygruppen enthaltenden Organosilanen höchster Reinheit
WO2008017554A1 (fr) 2006-08-10 2008-02-14 Evonik Degussa Gmbh Installation, réacteur et procédé pour la fabrication industrielle continue de 3-méthacryloxypropylalcoxysilanes
DE102011004058A1 (de) * 2011-02-14 2012-08-16 Evonik Degussa Gmbh Monochlorsilan, Verfahren und Vorrichtung zu dessen Herstellung

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10894801B2 (en) 2018-07-03 2021-01-19 Evonik Operations Gmbh Process for producing alkylalkoxysilanes
CN108970163A (zh) * 2018-10-09 2018-12-11 唐山三友硅业有限责任公司 高沸物精馏塔及精馏法提纯高沸物的工艺
US12275823B2 (en) 2021-06-30 2025-04-15 Evonik Operations Gmbh Process for producing high-purity hydrosilylation products

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DE102013214830A1 (de) 2015-02-05
EP3027305A1 (fr) 2016-06-08

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