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WO2008017555A1 - Installation et procédé pour la fabrication industrielle continue d'organosilanes - Google Patents

Installation et procédé pour la fabrication industrielle continue d'organosilanes Download PDF

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Publication number
WO2008017555A1
WO2008017555A1 PCT/EP2007/056955 EP2007056955W WO2008017555A1 WO 2008017555 A1 WO2008017555 A1 WO 2008017555A1 EP 2007056955 W EP2007056955 W EP 2007056955W WO 2008017555 A1 WO2008017555 A1 WO 2008017555A1
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Prior art keywords
reactor
reaction
catalyst
units
product
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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/EP2007/056955
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German (de)
English (en)
Inventor
Jürgen Erwin LANG
Georg Markowz
Harald Metz
Norbert Schladerbeck
Dietmar Wewers
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Evonik Operations GmbH
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Evonik Degussa GmbH
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Priority to EP07787231A priority Critical patent/EP2049243A1/fr
Publication of WO2008017555A1 publication Critical patent/WO2008017555A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • B01J19/0093—Microreactors, e.g. miniaturised or microfabricated reactors
    • 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
    • C07F7/14—Preparation thereof from optionally substituted halogenated silanes and hydrocarbons hydrosilylation reactions
    • 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
    • B01J2219/00781—Aspects relating to microreactors
    • B01J2219/00783—Laminate assemblies, i.e. the reactor comprising a stack of plates
    • 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
    • B01J2219/00781—Aspects relating to microreactors
    • B01J2219/00788—Three-dimensional assemblies, i.e. the reactor comprising a form other than a stack of plates
    • 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
    • B01J2219/00781—Aspects relating to microreactors
    • B01J2219/00819—Materials of construction
    • B01J2219/00822—Metal
    • 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
    • B01J2219/00781—Aspects relating to microreactors
    • B01J2219/00819—Materials of construction
    • B01J2219/00824—Ceramic
    • B01J2219/00826—Quartz
    • 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
    • B01J2219/00781—Aspects relating to microreactors
    • B01J2219/00819—Materials of construction
    • B01J2219/00831—Glass
    • 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
    • B01J2219/00781—Aspects relating to microreactors
    • B01J2219/00819—Materials of construction
    • B01J2219/00835—Comprising catalytically active material
    • 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
    • B01J2219/00781—Aspects relating to microreactors
    • B01J2219/00819—Materials of construction
    • B01J2219/00837—Materials of construction comprising coatings other than catalytically active coatings
    • 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
    • B01J2219/00781—Aspects relating to microreactors
    • B01J2219/00851—Additional features
    • B01J2219/00858—Aspects relating to the size of the reactor
    • B01J2219/0086—Dimensions of the flow channels
    • 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
    • B01J2219/00781—Aspects relating to microreactors
    • B01J2219/00851—Additional features
    • B01J2219/00867—Microreactors placed in series, on the same or on different supports
    • 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
    • B01J2219/00781—Aspects relating to microreactors
    • B01J2219/00851—Additional features
    • B01J2219/00869—Microreactors placed in parallel, on the same or on different supports
    • 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
    • B01J2219/00781—Aspects relating to microreactors
    • B01J2219/00851—Additional features
    • B01J2219/00871—Modular assembly
    • 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
    • B01J2219/00781—Aspects relating to microreactors
    • B01J2219/00873—Heat exchange
    • 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
    • B01J2219/00781—Aspects relating to microreactors
    • B01J2219/00889—Mixing

Definitions

  • the present invention relates to a novel plant for the continuous industrial production of organosilanes by reacting an ⁇ , ß-unsaturated aliphatic, optionally substituted compound with a HSi compound and a related method.
  • Organosilanes such as vinylchloro or vinylalkoxysilanes (EP 0 456 901 A1, EP 0 806 427 A2), chloroalkylchlorosilanes (DE-AS 28 15 316, EP 0 519 181 A1, DE 195 34 853 A1, EP 0 823 434 A1, EP 1 020 473 A2), alkylalkoxysilanes (EP 0 714 901 A1, DE 101 52 284 A1), fluoroalkylalkoxysilanes (EP 0 838 467 A1, DE 103 01 997 A1), aminoalkylalkoxysilanes (DE-OS 27 53 124, EP 0 709 391 A2 , EP 0 849 271 A2, EP 1 209 162 A2, EP 1 295 889 A2), glycidyloxyalkylalkoxysilanes (EP 1 070 721 A2, EP 0 934 947 A2), methacryloxy
  • Microstructured reactors as such for example for a continuous production of polyether alcohols (DE 10 2004 013 551 A1) or the synthesis of u. a. Ammonia, methanol, MTBE (WO 03/078052) are known. Also microreactors for catalytic reactions are known (WO 01/54807). However, so far the microreactor technology for the industrial production of organosilanes has been omitted or at least not realized. The tendency of alkoxy- and chlorosilanes to hydrolysis - even with small amounts of moisture - and corresponding caking in a Organosilanher einsstrom probably to be seen as a sustainable problem.
  • the object was to provide a further possibility for the industrial production of said organosilanes.
  • the pre-mixing can also be done cold, then heat in the multi-element reactor and there targeted and continuously implement. It is also possible to add a catalyst to the educt mixture. Subsequently, the product can be worked up continuously, z. As in an evaporation, rectification and / or using a Kurzweg- or thin-film evaporator - to name just a few options.
  • the heat of reaction liberated during the reaction can advantageously be removed in the multielement reactor via the large surface area of the interior walls of the reactor in relation to the reactor volume and, if provided, to a heat transfer medium.
  • the present invention enables the preservation of process reliability in a comparatively simple and economical manner.
  • a drastic process intensification in particular a shortening of the process time under reaction conditions by more than 99%, based on the space-time yield, compared to the standard batch process can be achieved.
  • the present reactions were carried out in a stainless steel multi-element reactor.
  • a longer service life of metal reactors are found because the material fatigue compared to a batch mode significantly slower.
  • reactions such as those of vinyl chloride and trichlorosilane to vinyltrichlorosilane can be advantageously carried out at a higher temperature.
  • the reproducibility compared to comparable studies in batch process could be significantly improved.
  • a multi-element reactor advantageously includes a prereactor
  • a surprisingly long plant life even without stoppages caused by caking or deposits are made possible.
  • the present invention thus relates to a plant for the continuous industrial implementation of a reaction, wherein an ⁇ , ß-unsaturated aliphatic, optionally substituted compound A with an HSi compound B optionally in the presence of a catalyst C and / or optionally in the presence of further auxiliaries and the plant is based at least on the starting material combination (3) for the components A (1) and B (2), at least one multi-element reactor (5), which in turn contains at least two reactor units, and based on a subsequent product work-up (8).
  • FIGS 1 to 6 are flow diagrams of plants or system parts as preferred Embodiments of the present invention can be seen.
  • FIG. 1 shows a preferred continuous system in which the reactant components A and B are combined in unit (3), fed to unit (5), which may contain an immobilized catalyst, reacted therein and the reaction product in the unit (8) is worked up.
  • FIG. 2 shows a further preferred embodiment of a continuous plant according to the invention, in which a catalyst C is fed to component B.
  • the catalyst can also be fed to the unit (3) or, as can be seen in FIG. 3, the catalyst C metered into a mixture of the components A and B shortly before entry into the multi-reactor unit (5).
  • a reactor unit is understood as meaning an element of the multielement reactor (5), each element representing an area or reaction space for the said reaction, cf. for example, (5.1) (reactor unit in the form of a pre-reactor) in Figure 4 and (5.5) [reactor unit of an integrated block reactor (5.3)] in Figure 5 and (5.10) [reactor unit of a Mikrorohrbündel Anlagen (2004)erreaktors (5.9)].
  • Reactor units of a multielement reactor (5) in the context of the present invention are in particular stainless steel or quartz glass capillaries, stainless steel tubes or well-dimensioned stainless steel reactors, for example pre-reactors (5.1), tubes (5.10) in microtube bundle heat exchanger reactors [e.g. B.
  • the inner walls of the reactor elements may be coated, for example with a ceramic layer, a layer of metal oxides, such as Al 2 O 3 , TiO 2 , SiO 2 , ZrO 2 , zeolites, silicates, to name only a few, but also organic polymers, in particular fluoropolymers, such as Teflon, are possible.
  • metal oxides such as Al 2 O 3 , TiO 2 , SiO 2 , ZrO 2 , zeolites, silicates, to name only a few, but also organic polymers, in particular fluoropolymers, such as Teflon, are possible.
  • a plant according to the invention comprises one or more multi-element reactors (5), which in turn are based on at least 2 to 1,000,000 reactor units, including all natural numbers in between, preferably from 3 to 10,000, in particular from 4 to 1,000 reactor units.
  • the reactor or reaction space of at least one reactor unit preferably has a semicircular, semi-oval, round, oval, triangular, square, rectangular or trapezoidal cross-section perpendicular to the flow direction.
  • a cross section preferably has a cross-sectional area of 75 ⁇ m 2 to 75 cm 2 .
  • Particularly preferred are cross-sectional areas of 0.7 to 120 mm 2 and all numerically intervening numerical values.
  • a diameter of> 30 ⁇ m to ⁇ 15 mm, in particular 150 ⁇ m to 10 mm is preferred.
  • Square cross-sectional areas preferably have edge lengths of> 30 ⁇ m to ⁇ 15 mm, preferably 0.1 to 12 mm.
  • reactor units with differently shaped cross-sectional areas can be present in a multielement reactor (5) of a system according to the invention.
  • the structure length in a reactor unit i. H. from entry of the reaction or product stream into the reactor unit, cf. z. B. (5.1 and 5.1.1) or (5.5 and 5.5.1), until the exit, cf. (5.1.2) or (5.5.2), preferably 5 cm to 500 m, including all numerically intervening numerical values, particularly preferably> 15 cm to 100 m, very particularly preferably 20 cm to 50 m, in particular 25 cm to 30 m.
  • reactor units whose respective reaction volume (also referred to as the reactor volume, ie the product of Cross-sectional area and structure length) 0.01 ml to 100 l, including all numerically intervening numerical values.
  • the reactor volume of a reactor unit of a system according to the invention is particularly preferably 0.05 ml to 10 l, very particularly preferably 1 ml to 5 l, very particularly preferably 3 ml to 2 l, in particular 5 ml to 500 ml.
  • systems according to the invention can be based on one or more multi-element reactors (5), which are preferably connected in parallel.
  • said multi-element reactors (5) can also be switched one behind the other so that the product which originates from the preceding multi-element reactor can be fed to the inlet of the subsequent multi-element reactor.
  • Present multielement reactors (5) can advantageously be combined with a reactant component stream (4) or (5.2), which is suitably divided into the respective sub-streams, cf. z. B. (5.4) in Figure 5 and (5.11) in Figure 6, are fed.
  • the product streams can be combined, cf. z. B. (5.7) in Figure 5, (5.12) in Figure 6 and (7), and then work up advantageously in a workup unit (8).
  • a processing unit (8) initially have a condensation stage or evaporation stage, which optionally followed by one or more distillation stages.
  • a multielement reactor (5) of a system according to the invention can be based on at least two stainless steel capillaries connected in parallel or on at least two quartz glass capillaries connected in parallel or at least one tube bundle heat exchanger reactor (5.9) or at least one integrated block reactor (5.3).
  • stainless steel capillaries or reactors which advantageously consist of a high-strength, high-temperature-resistant and stainless steel,
  • capillaries, block reactors or tube bundle heat exchangers of steel type 1.4571 or 1.4462 see.
  • the steel facing the reaction chamber surface of a stainless steel capillary or a multi-element reactor with a polymer layer, for example a fluorine-containing layer, including Teflon, or a ceramic layer, preferably an optionally porous SiO 2 -, TiO 2 - or Al 2 O 3 layer, in particular for receiving a catalyst be equipped.
  • Suitable stainless steel or quartz glass capillaries are generally available commercially.
  • a multi-element reactor (5) may include a shell and tube heat exchanger reactor, which may optionally also be temperature-controlled in countercurrent.
  • a so-called, preferably micro-structured tube bundle heat exchanger reactor used according to the invention ie micro tube bundle heat exchanger reactor, cf.
  • 5.9) in Figure 6 suitably from a tube bundle (5.10), wherein the respective tubes (5.10) preferably have the above dimensions are the same, especially in terms of length and diameter, and made of a stainless steel.
  • the inlet planes of the respective tubes (5.10) are oriented in one plane and have a common educt feed (4), (5.11) and a common product removal or combination (5.12), (7).
  • the tube bundle (5.10) can be lapped by a medium (D) for tempering (5.13).
  • the tube bundle is flushed against the flow direction with tempering medium (D, 6.1, 6.2).
  • tempering medium D, 6.1, 6.2
  • such a system can be introduced into a reactor jacket (5.14), the latter advantageously having an educt feed (4), a product removal (7), a temperature-control agent supply (6.1) and a temperature-control agent removal (6.2).
  • a microtube bundle heat exchanger reactor (5.9), cf. FIG. 6, at least one pre-reactor (5.1), cf. also Figure 4, above.
  • a multielement reactor (5) advantageously an integrated block reactor, as used, for example, as a temperature-controllable block reactor constructed from defined metal plates (also referred to as plane below) from http://www.heatric.com/pche-construction.html is apparent.
  • FIG. 5 shows a plane of an integrated block reactor (5.3) with a plurality of reactor units or elements (5.5).
  • a level usually consists of a base plate made of metal with metal walls thereon (5.6), the reaction chambers (5.5) together with a cover plate made of metal and a unit for temperature control (6.5, 6.6), preferably a further level or textured metal plate, limit.
  • the unit (5.3) contains an area (5.4) for feeding and distributing the educt mixture (5.2) into the reactor elements (5.5) and a region (5.7) for combining the product streams from the reaction areas (5.5) and discharging the product stream (7).
  • several such previously described levels can be connected one above the other.
  • integrated block reactors (5.3) are advantageously surrounded by a temperature control unit (6.5, 6.6) which enables the heating or cooling of the block reactor (5.3), ie a targeted temperature control.
  • Marlotherm or Mediatherm by means of a heat exchanger (6.7) tempered and fed via line (6.8) a pump (6.9) and line (6.1) of the temperature control unit (6.5) and via (6.6) and (6.2) removed and the heat exchanger unit (6.7 ).
  • a heat exchanger 6.7
  • a pump 6.9
  • the integrated block reactor (5.3) and the associated temperature control unit (6.5, 6.6) can also be designed such that a temperature control plane is arranged between two reactor element planes, which guides the temperature control medium even more directionally between the areas (6.1, 6.5) and (6.6 , 6.2).
  • a multielement reactor (5) comprising at least one pre-reactor (5.1) and at least one further reactor unit, for example a stainless steel capillary, or a pre-reactor (5.1) and at least one integrated block reactor (5.3), cf. FIG. 4, or at least one pre-reactor (5.1) and a shell-and-tube heat exchanger reactor (5.9), cf. Figure 6, includes.
  • the prereactor (5.1) is suitably tempered, d. H. cooled and / or heated, off (D, 6.3, 6.4).
  • a pre-reactor (5.1) in the context of the multi-element reactor (5), in particular for the implementation of silanes, is that in addition to carrying out the continuous reaction by a targeted Separation and discharge of hydrolyzates or particles unscheduled Still-C. Can advantageously minimize downtime. So you can pre-reactor (5.1) additionally upstream or downstream of a filter for particle separation. But you can also integrate the filter in the prereactor.
  • a plant according to the invention for the continuous industrial implementation of reactions based on a Eduktzusammen arrangement (3) for the components A and B, at least one said multi-element reactor (5) and on a product work-up (8), cf.
  • FIG. 1
  • the educt components A and B can each be combined in a targeted manner from a storage unit by means of pumps and optionally by means of differential weighing system in the area (3).
  • components A and B are metered at ambient temperature, preferably at 10 to 40 ° C., and mixed in region (3). But you can also preheat at least one of the components, both components or feedstocks or the corresponding mixture.
  • the said storage unit can be conditioned and the storage containers can be designed to be temperature-controlled.
  • the multielement reactor (5) is preferably brought to or maintained at the desired operating temperature by means of a temperature control medium D (6.1, 6.2) so that undesirable temperature peaks and temperature fluctuations known from batch systems are advantageously avoided or adequately achieved in the present system according to the invention can become low.
  • the product or crude product stream (7) is continuously the product work-up (8), for example, a rectification, fed, for example, about Head (10) a low-boiling product F, for example, an excessively used and optimally recyclable silane, and on the bottom (9) a heavy boiling product E can continuously decrease. It is also possible to remove side streams as a product from the unit (8).
  • the maximum particle diameter of the suspension catalyst should be less than 1/3, advantageously 1/10 to 1/100 of the extent of the smallest free cross section of the cross sectional area of a reactor unit (5) and the average particle cross sectional area, preferably 10 2 to 10 ⁇ 6 mm 2 preferably 10 to 10 ⁇ 4 mm 2 , very particularly preferably 1 to 10 3 mm 2 , so that there is no blockage advantageous, but still can be easily separated from the product stream in a downstream arrangement.
  • FIG. 2 reveals that it is advantageous to meter in a said catalyst C to component B before it is combined with component A in region (3).
  • a plant according to the invention for the continuous industrial implementation of the reaction of a said compound A with a compound B is optionally based in the presence of a catalyst and further auxiliaries on at least one reactant combination (3), at least one multi-element reactor (5), which in turn contains at least two reactor units, and on a product work-up (8).
  • the reactants or feedstocks are provided in a storage unit for carrying out the reaction and fed or metered as required.
  • a system according to the invention is equipped with the measuring, metering, shut-off, transport, conveying, monitoring, control units and exhaust gas and waste disposal devices which are conventional in the art.
  • system according to the invention can be advantageously accommodated in a portable and stackable container and handled flexibly. So you can bring a system according to the invention quickly and flexibly, for example, to the respective educt or energy sources. With a system according to the invention, but also with all the advantages, it is possible to continuously provide product at the point at which the product is further processed or used further, for example directly at the customer's.
  • Another particularly noteworthy advantage of a plant according to the invention for the continuous industrial implementation of a reaction of ⁇ , ß-unsaturated compounds A with a HSi compound B is that it now has a Possibility to produce even small special products with sales volumes between 5 kg and 50 000 t pa, preferably 10 kg to 10 000 t pa, in a simple and economical way continuously and flexibly.
  • unnecessary downtime, the yield, the selectivity influencing temperature peaks and fluctuations and too long residence times and thus unwanted side reactions can be advantageously avoided.
  • such an installation can also be used optimally for the production of existing silanes from an economical, ecological and customer-friendly point of view.
  • the subject of the present invention is a process for the continuous industrial production of an organosilane of the general formula
  • Y is an organo-functional group selected from vinyl, C 2 - to C 8 -alkyl, C 3 - to C 6 -fluoroalkyl, C 3 - to C 4 -chloroalkyl, aminoalkyl, glycidyloxyalkyl, methacryloxyalkyl, polyetheralkyl and R 'for a d -C 4 -alkyl group, m is 0 or 1 and X represents a hydrolyzable group,
  • one carries out the reaction of the educt components A and B in at least one multi-element reactor, which in turn is based on at least two reactor units.
  • the reaction is carried out in at least one multi-element reactor (5), the reactor units - especially but not exclusively - made of stainless steel or quartz glass or its reaction spaces are limited by stainless steel or quartz glass, the surfaces of the reactor units may be coated or occupied , for example with Teflon.
  • the reactor units whose respective cross-section is semicircular, semi-oval, round, oval, triangular, square, rectangular or trapezoidal.
  • reactor units are used whose respective cross-sectional area is 75 ⁇ m 2 to 75 cm 2 .
  • reactor units which have a structure length of 1 cm to 200 m, particularly preferably 10 cm to 120 m, very particularly preferably 15 cm to 80 m, in particular 18 cm to 30 m, including all possible numerical values Be included above areas.
  • reactor units are suitably used whose respective reaction volume is 0.01 ml to 100 l including all numerically intermediate numerical values, preferably 0.1 ml to 50 l, particularly preferably 1 ml to 20 l, very particularly preferably 2 ml to 10 1, in particular 5 ml to 5 1.
  • the said reaction can also advantageously be carried out in a plant with a multi-element reactor (5) which is based on at least one stainless steel capillary or at least one quartz glass capillary or at least one integrated block reactor (5.3) or at least one tube bundle heat exchanger reactor (5.9).
  • a multi-element reactor (5) which contains at least one pre-reactor (5.1) is preferred.
  • the process according to the invention is particularly preferably carried out in reactor units made of stainless steel. It is further preferred that in the process according to the invention, the surface of the reactor units of the multielement reactor which is in contact with the starting material / product mixture is coated with a catalyst, in particular when working in the presence of an immobilized catalyst or heterogeneous catalyst.
  • the reaction of components A and B is carried out in the presence of a homogeneous catalyst C
  • the substances used for the preconditioning of the multielement reactor can be collected and later metered into the educt stream at least proportionally or fed directly to the product work-up and worked up.
  • the process according to the invention it is possible to carry out the said reaction in the gas and / or liquid phase.
  • the reaction or product mixture can be present in one, two or three phases.
  • the reaction is preferably carried out in a single-phase, in particular in the liquid phase.
  • the process of the invention is advantageously carried out using a multielement reactor at a temperature of 0 to 800 0 C at a pressure of 0.1 to 500 bar abs.
  • the differential pressure in a system according to the invention d. H. between Eduktzusammen entry (3) and product work-up (8), 1 to 10 bar abs.
  • a pressure-holding valve in particular when using trimethoxysilane (TMOS).
  • TMOS trimethoxysilane
  • the reaction can according to the invention analogously to the space velocity at a linear velocity (LV) of 1 to 1 ⁇ 10 4 h '1 i. N. perform.
  • the flow velocity of the material stream is situated in the reactor units preferably in the range of 0.0001 to 1 m / s iN, more preferably 0.0005 to 0.7 m / s, most preferably 0.001 to 0.5 m / s, in particular 0.05 to 0.3 m / s, and all possible numerical values within the above
  • the ratio of reactor surface area (A) to reactor volume (V) is predominant in the reaction according to the invention, then an AV ratio of 20 to 5,000 m 2 / m 3 is preferred, including all numerically possible individual values
  • the AV ratio is a measure of the heat transfer and of possible heterogeneous (wall) influences.
  • reaction in the process according to the invention is advantageously carried out at a mean residence time (.tau.) Of 10 seconds to 60 minutes, preferably 1 to 30 minutes, more preferably 2 to 20 minutes, in particular 3 to 10 minutes.
  • a mean residence time Of 10 seconds to 60 minutes, preferably 1 to 30 minutes, more preferably 2 to 20 minutes, in particular 3 to 10 minutes.
  • Suitable components B in the process according to the invention are silanes of the general formula (II)
  • R ' is a C 1 to C 4 alkyl group, preferably methyl, m is 0 or 1 and X is a hydrolyzable group, preferably chloride, methoxy, ethoxy.
  • TCS trichlorosilane
  • TMOS trimethoxysilane
  • TEOS triethoxysilane
  • components A and B are preferably employed in a molar ratio A to B of 1: 5 to 100: 1, more preferably 1: 4 to 5: 1, very preferably 1: 2 to 2: 1, in particular of 1: 1, 5 to 1, 5: 1, including all possible numbers within the aforementioned ranges.
  • the process according to the invention is preferably carried out in the presence of a catalyst C.
  • a catalyst C it is also possible to operate the process according to the invention without the addition of a catalyst, in which case a clear decrease in the yield is generally to be expected.
  • the process according to the invention is used for carrying out a hydrosilylation reaction for the preparation of organosilanes of the formula (I), in particular homogeneous catalysts of the series Pt complex catalyst, for example those of the Karstedt type, such as Pt (0) -divinyltetramethyldisiloxane in xylene,
  • the known complex catalysts in an organic, preferably polar solvent for example - but not exclusively - ethers, such as THF, ketones, such as acetone, alcohols, such as isopropanol, aliphatic or aromatic hydrocarbons, such as toluene, xylene, CHC, CFC , to solve.
  • organic, preferably polar solvent for example - but not exclusively - ethers, such as THF, ketones, such as acetone, alcohols, such as isopropanol, aliphatic or aromatic hydrocarbons, such as toluene, xylene, CHC, CFC , to solve.
  • an activator for example in the form of an organic or inorganic acid such as HCl, H 2 SO 4 , H 3 PO 4 , mono- or dicarboxylic acids, HCOOH, H 3 C-COOH , Propionic acid, oxalic acid, succinic acid, Citric acid, benzoic acid, phthalic acid - just to name a few.
  • an organic or inorganic acid such as HCl, H 2 SO 4 , H 3 PO 4 , mono- or dicarboxylic acids, HCOOH, H 3 C-COOH , Propionic acid, oxalic acid, succinic acid, Citric acid, benzoic acid, phthalic acid - just to name a few.
  • an organic or inorganic acid to the reaction mixture can take on another advantageous function, for example as a stabilizer or inhibitor of impurities in the trace range.
  • the surface of the present interior walls of the reactor in particular in the case of metal reactors, can also act catalytically under operating conditions.
  • the olefin component A is added to the catalyst, based on the metal, preferably in a molar ratio of 2,000,000: 1 to 1,000: 1, more preferably 1,000,000: 1 up to 4 000: 1, in particular from 500 000: 1 to 10 000: 1, and all possible figures within the abovementioned areas.
  • an immobilized catalyst or heterogeneous catalyst from the series of transition metals or noble metals or a corresponding multielement catalyst for carrying out the hydrosilylation reaction. So you can, for example - but not exclusively - use precious metal sludge or precious metal on activated carbon. But you can also provide a fixed bed for receiving a heterogeneous catalyst in the field of multi-element reactor. So you can, for example - but not exclusively - also heterogeneous catalysts that bring on a carrier such as beads, strands, pellets, cylinders, stirrers, etc., inter alia SiO2, TiO2, Al2O3, ZrO2, in the reaction zone of the reactor units.
  • reaction of a fluoroolefin with an HSi compound can also be carried out according to the invention, but also in the presence of a free-radical initiator, as can be deduced in particular from DE 103 01 997 A1.
  • solvents or diluents such as alcohols, aliphatic and aromatic hydrocarbons, CHC, CFC, ethers, esters, ketones - to name a few - can be used as auxiliaries.
  • Such adjuvants can be removed from the product, for example, in the product work-up.
  • inhibitors for example polymerization inhibitors or corresponding mixtures, can be used as additional auxiliaries in the present process.
  • VC vinyl chloride
  • TCS trichlorosilane
  • VTCS vinyltrichlorosilane
  • VC and TCS are employed in a molar ratio of 1: 1, 05 to 1: 2.
  • the reaction of the components is generally carried out at 300 to 700 0 C and a pressure of 1 to 100 bar abs., Preferably at 1, 5 to 10 bar abs., In particular at 2 to 5 bar abs. You can do without the presence of a catalyst.
  • the thermal conversion of VC and TCS is preferably carried out in a system according to the invention, advantageously using a multielement reactor which is operated on a temperature-controllable prereactor and a downstream heatable, integrated block reactor or prereactor and based at least one downstream stainless steel capillary.
  • the prereactor is preferably operated at 200 to 450 0 C and 1 to 10 bar abs. and the pre-reactor downstream reactor units preferably at 450 to 650 0 C and 1 to 10 bar abs.
  • the residence time of the reaction mixture in the multi-element reactor is preferably 0.2 to 20 seconds, more preferably 0.5 to 5 seconds.
  • the crude product obtained in the multi-element reactor is suitably condensed in the product work-up and worked up by distillation, preferably in two stages.
  • the task of the crude product is preferably carried out at the top of the column.
  • vinyltrichlorosilane is advantageously obtained which can be removed in work-up (8) as bottom product at virtually complete conversion, preferably> 90% and with a purity of about 98%.
  • HCl (g) and excess TCS are generally passed overhead. It is possible to condense TCS and advantageously recycle it as starting material component.
  • acetylene for the preparation of vinyltrichlorosilane or vinylmethyldichlorosilane but can also be acetylene with trichlorosilane or methyldichlorosilane at a pressure of> 1 to 4 bar abs., And a temperature of 60 to 180 0 C in the presence of a homogeneous catalyst by the novel process.
  • acetylene is used in a multiple molar excess.
  • Acetylene is preferably added to trichlorosilane in a molar ratio of 1.5: 1 to 20: 1.
  • the Edukt- and the product mixture are usually two-phase. In the implementation usually ensures a good mixing of the components.
  • catalysts are homogeneous catalysts as reaction products of platinum (IV) chloro acid with ketones, preferably ketones, which are free of aliphatic multiple bonds, such as cyclohexanone, methyl ethyl ketone acetylacetone and / or acetone phenone, especially cyclohexanone.
  • ketones preferably ketones, which are free of aliphatic multiple bonds, such as cyclohexanone, methyl ethyl ketone acetylacetone and / or acetone phenone, especially cyclohexanone.
  • These reaction products can be prepared, for example, by heating a solution of commercial platinum (IV) chloro acid in the ketone with which this acid is to be reacted for 0.5 to 6 hours at 60 to 120 0 C and in the form of the solution thus obtained Removal of the water formed in the reaction, z. B.
  • ketone per part by weight of platinum (IV) chloroacid, preferably 20 to 2,000 parts by volume of ketone are used.
  • platinum (IV) chloroacid per part by weight of platinum (IV) chloroacid, preferably 20 to 2,000 parts by volume of ketone are used.
  • other noble metal catalysts dissolved in an inert solvent or a finely dispersed heterogeneous catalyst for example Pt sludge or Pt on activated carbon.
  • a substantially inert carrier gas for example argon or nitrogen, can be used.
  • a multi-element reactor having a comparatively small structure length, in particular 1 to 100 cm, and a hydraulic diameter of 0.1 to 75 cm 2 of the respective reactor units. The crude product thus obtained is subsequently worked up by distillation, it being possible to recycle the acetylene-containing fraction.
  • alkylchlorosilanes such as chloroalkylchlorosilanes or fluoroalkylchlorosilanes, and fluoroalkylalkoxysilanes, to name but a few, can be prepared by the process according to the invention in an advantageous manner.
  • 3-glycidyloxyalkylalkoxysilanes can advantageously be prepared by the process according to the invention by hydrosilylation of allylglycidyl ether in the presence of a catalyst, cf. u. a. EP 0 934 947 A2 and EP 1 070 721 A2.
  • 3-methacryloxyalkylalkoxysilanes can be obtained by the process according to the invention.
  • the reaction according to the invention of an allyl methacrylate with a hydrogenalkoxysilane in the presence of a homogeneous catalyst and a system for inhibiting polymerization could also be carried out without the occurrence of the dreaded "popcorn formation.”
  • polyether-functional alkoxysilanes can advantageously be obtained by the process according to the invention.
  • Starting materials and operating parameters can be found, for example, in EP 0 387 689 A1.
  • the process according to the invention is carried out as follows:
  • the reactant components A and B and optionally C and, if appropriate, further auxiliaries are metered in and mixed. It is endeavored to meter a homogeneous catalyst with an accuracy of ⁇ 20%, preferably ⁇ 10%. In special cases, one can dose the homogeneous catalyst in the mixture of the components A and B only shortly before entering the multi-element reactor. Subsequently, it is possible to feed the starting material mixture to the multielement reactor and to react the components under temperature control. However, it is also possible first to rinse or precondition the multielement reactor with a catalyst-containing educt or reactant mixture before the temperature is advanced to carry out the reaction. It is also possible to carry out the preconditioning of the multielement reactor at a slightly elevated temperature. The product streams (crude product) combined in the multielement reactor can subsequently be worked up in a suitable manner in a product work-up of the plant according to the invention.
  • the present invention also relates to the use of a plant according to the invention for the continuous industrial implementation of hydrosilylation, wherein an ⁇ , ß-unsaturated aliphatic, optionally substituted compound A with an HSi compound B optionally in the presence of a catalyst C and / or other auxiliaries implements.
  • a temperature control over a heating and cooling system was provided for the pre-reactor and the shell-and-tube heat exchanger reactor.
  • TMOS trimethoxysilane
  • the pressure was 25 ⁇ 10 bar.
  • the system should be kept as free of H 2 O as possible.
  • the system was rinsed for 2 hours prior to raising the temperature in the reactor with educt mixture.
  • the temperature was advanced in the reactors, set to 110 0 C and operated continuously over 18 days. After reactor samples were taken at intervals for GC-WLD measurements.
  • the conversion based on the olefin was on average 96% and the selectivity, based on the ⁇ -product, was 75%.
  • the plant used for the continuous production of hexadecyltrimethoxysilane consisted essentially of the educt reservoirs, HPLC pumps, control, measuring and metering units, a T-mixer, a pre-reactor made of stainless steel (diameter 5 mm, length 40 mm), a stainless steel capillary ( Diameter 1 mm, length 50 m), a heat bath with temperature control for the temperature control of the pre-reactor and the capillary, a pressure-maintaining valve, a wiped Thin-film evaporator and connecting lines in the system for reactant feed between the abovementioned plant components as well as product, recycling and flue-gas removal.
  • the olefin hexadecene-1 purity 93%, Degussa AG
  • the pressure was 25 ⁇ 10 bar.
  • the system was rinsed with educt mixture for 1 hour prior to raising the temperature in the reactor system.
  • the temperature was raised in the bath and set in the reactor system to 140 0 C and operated continuously for 16 days.
  • After reactor samples were taken at intervals for GC-WLD measurements.
  • the conversion (including rearranged educt) based on the olefin was on average 36% and the selectivity based on TMOS was 99%.
  • the crude product thus obtained was continuously driven into the vacuum-operated thin-film evaporator.
  • the overhead product was condensed, analyzed, post-condensed and recycled. In the bottom continuously around 0.5 kg / h of a mixture of hexadecene and Dynasylan ® were discharged and 9116 continuously fed to a further separation unit.
  • the plant used for the continuous production of 3-methacryloxypropyltrimethoxysilane consisted essentially of the educt reservoirs, HPLC pumps, control, measuring and metering units, a T-mixer, a pre-reactor Stainless steel (diameter 5 mm, length 40 mm), two parallel connected stainless steel capillaries (each 1 mm in diameter and a length of 25 m), a heat bath with temperature control for the prereactor and the two capillaries, a pressure holding valve, a N 2 operated stripping and a downstream short-path evaporator and connecting lines in the system for the educt feed, product, recycling and flue gas removal.
  • the pressure was 25 ⁇ 10 bar.
  • a H 2 O and O 2 -free state of the system should be ensured.
  • the system was rinsed with educt mixture for 1 hour prior to raising the temperature in the reactor system.
  • the temperature was raised in the bath, adjusted in the reactor system to 75 0 C and operated continuously for 11 days.
  • samples were taken at intervals on the crude product stream and analyzed by GC-WLP measurements.
  • the conversion based on the olefin was 99% on average and the selectivity based on the ⁇ product was 75%.
  • the product stream thus obtained was continuously stripped.
  • the top product was fed to a thermal afterburning and the bottoms product (3-methacryloxypropyltrimethoxysilane) fed continuously with 0.4 kg / h of purification by means of thin-film or short-path evaporator.
  • the pressure was 25 ⁇ 10 bar.
  • the resulting top product essentially TCS, could be used as recycling.
  • Almost 0.5 kg of hydrosilylation product was withdrawn from the bottom of the stripping column per hour.
  • fluoroalkyltrichlorosilane obtained can be reacted with an alcohol be reacted to obtain so advantageous fluoroalkylalkoxysilane.

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

Abstract

La présente invention concerne une installation pour la réalisation industrielle continue d'une réaction selon laquelle un composé A aliphatique, ß-insaturé, éventuellement substitué est mis en réaction avec un composé HSi B en présence d'un catalyseur C et éventuellement d'adjuvants supplémentaires. L'installation selon l'invention comporte, au moins à la jonction des adduits (3) pour les composants A (1) et B (2), au moins un réacteur multiélément (5), comprenant lui-même au moins deux unités de réacteur, et est fondée sur le traitement d'un produit (8). L'invention concerne également l'utilisation d'une installation pour la réalisation industrielle continue d'une hydrosilylation selon laquelle un composé A aliphatique, ß-insaturé, éventuellement substitué est mis en réaction avec un composé HSi B éventuellement en présence d'un catalyseur C.
PCT/EP2007/056955 2006-08-10 2007-07-09 Installation et procédé pour la fabrication industrielle continue d'organosilanes Ceased WO2008017555A1 (fr)

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DE102007023757A DE102007023757A1 (de) 2006-08-10 2007-05-22 Anlage und Verfahen zur kontinuierlichen industriellen Herstellung von Organosilanen
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EP2360205A1 (fr) 2010-02-19 2011-08-24 BYK-Chemie GmbH Procédé d'hydrosilylation continue
US8039646B2 (en) 2007-02-09 2011-10-18 Evonik Degussa Gmbh Process for preparing glycidyloxyalkyltrialkoxysilanes
US10399997B2 (en) 2014-07-11 2019-09-03 Geo Specialty Chemicals Uk Limited Process for preparation of 3-methacryloxypropyldimethylchlorosilane in continuous flow reactor
CN113861233A (zh) * 2021-10-27 2021-12-31 湖北兴瑞硅材料有限公司 一种甲基三甲氧基硅烷的制备工艺及装置
CN114940687A (zh) * 2022-05-30 2022-08-26 杭州瀛拓科技有限公司 一种多取代乙烯基硅（氧）烷的连续流合成方法
US12275823B2 (en) 2021-06-30 2025-04-15 Evonik Operations Gmbh Process for producing high-purity hydrosilylation products

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CN109824713B (zh) * 2019-03-05 2021-07-09 湖北江瀚新材料股份有限公司 一种长链烷基三烷氧基硅烷的制备方法
CN114394991B (zh) * 2022-01-27 2024-08-13 浙江锦华新材料股份有限公司 一种催化合成乙烯基三氯硅烷的方法
CN116574124A (zh) * 2022-04-18 2023-08-11 华诺森（武汉）生物医药技术有限公司 一种微通道反应器制备3-甲基丙烯酰氧基丙基二甲基氯硅烷的方法

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US8039646B2 (en) 2007-02-09 2011-10-18 Evonik Degussa Gmbh Process for preparing glycidyloxyalkyltrialkoxysilanes
EP2360205A1 (fr) 2010-02-19 2011-08-24 BYK-Chemie GmbH Procédé d'hydrosilylation continue
WO2011101441A1 (fr) 2010-02-19 2011-08-25 Byk-Chemie Gmbh Procédé d'hydrosilylation continue
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US10399997B2 (en) 2014-07-11 2019-09-03 Geo Specialty Chemicals Uk Limited Process for preparation of 3-methacryloxypropyldimethylchlorosilane in continuous flow reactor
US12275823B2 (en) 2021-06-30 2025-04-15 Evonik Operations Gmbh Process for producing high-purity hydrosilylation products
CN113861233A (zh) * 2021-10-27 2021-12-31 湖北兴瑞硅材料有限公司 一种甲基三甲氧基硅烷的制备工艺及装置
CN114940687A (zh) * 2022-05-30 2022-08-26 杭州瀛拓科技有限公司 一种多取代乙烯基硅（氧）烷的连续流合成方法

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