Nothing Special   »   [go: up one dir, main page]

EP1965901A2 - Procede pour creer des composes couples aryle-aryle - Google Patents

Procede pour creer des composes couples aryle-aryle

Info

Publication number
EP1965901A2
EP1965901A2 EP06829097A EP06829097A EP1965901A2 EP 1965901 A2 EP1965901 A2 EP 1965901A2 EP 06829097 A EP06829097 A EP 06829097A EP 06829097 A EP06829097 A EP 06829097A EP 1965901 A2 EP1965901 A2 EP 1965901A2
Authority
EP
European Patent Office
Prior art keywords
reactor
aryl
fixed bed
capillary
reaction
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.)
Withdrawn
Application number
EP06829097A
Other languages
German (de)
English (en)
Inventor
Torsten Zech
Gunilla Kaiser
Oliver Koechel
Oliver Laus
Denis Huertgen
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
HTE GmbH
HTE GmbH the High Throughput Experimentation Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by HTE GmbH, HTE GmbH the High Throughput Experimentation Co filed Critical HTE GmbH
Publication of EP1965901A2 publication Critical patent/EP1965901A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • B01J2219/00835—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
    • B01J2219/00851—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
    • B01J2219/00873—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
    • 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
    • B01J2219/00891—Feeding or evacuation
    • 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
    • B01J2219/00905—Separation
    • B01J2219/00916—Separation by chromatography
    • 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
    • B01J2219/0095—Control aspects
    • B01J2219/00952—Sensing operations
    • B01J2219/00954—Measured properties
    • B01J2219/00957—Compositions or concentrations
    • 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
    • B01J2219/0095—Control aspects
    • B01J2219/00952—Sensing operations
    • B01J2219/00968—Type of sensors
    • B01J2219/0097—Optical sensors
    • B01J2219/00972—Visible light
    • 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
    • B01J2219/0095—Control aspects
    • B01J2219/00952—Sensing operations
    • B01J2219/00968—Type of sensors
    • B01J2219/0097—Optical sensors
    • B01J2219/00975—Ultraviolet light
    • 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
    • B01J2219/0095—Control aspects
    • B01J2219/00952—Sensing operations
    • B01J2219/00968—Type of sensors
    • B01J2219/0097—Optical sensors
    • B01J2219/00977—Infrared light
    • 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
    • B01J2219/0095—Control aspects
    • B01J2219/00984—Residence time
    • 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
    • B01J2219/0095—Control aspects
    • B01J2219/00986—Microprocessor

Definitions

  • aryl-aryl-coupled compounds are of great economic and technical interest in the fields of pharmaceutical and agrochemicals as well as in the field of optoelectronics.
  • optoelectronic applications the use of aryl-aryl-coupled compounds as organic semiconductors, organic solar cells or liquid crystals should be mentioned by way of example.
  • the purity of the aryl-aryl-coupled compounds is of central importance for the mentioned as well as for other technical applications.
  • a cleaning is often very expensive and thus costly.
  • the molecular weight distribution should be kept within narrow limits. Deviations from the product purity targets, as well as the physical and chemical properties, may result in the compounds not being able to be used for the intended applications.
  • the principle of coupling reactions for the preparation of aryl-aryl compounds has been known for some time.
  • a disadvantage of the above-mentioned known continuous process for (hetero) coupling is that during the reaction in (capillary) reactor only small amounts of starting material (s) can be implemented and the process is limited to low molecular weight organic compounds and not can be readily transferred to polymerization reactions, in particular not those that are to lead to high molecular weights. Furthermore, in the reactors described in this prior art, multiphase reactions can not or only poorly be carried out.
  • WO 03/048225 An application of coupling reactions to the polymerization is described in WO 03/048225.
  • the disclosure of WO 03/048225 is limited to the non-continuous batch mode in a stirred-tank reactor.
  • a two-phase reaction aqueous phase with base, organic phase with aryl compounds
  • Disadvantages of the production process described in WO 03/048225 are the batch-to-batch variations that occur in batch mode. This applies in particular to polymerization reactions in which, at the end of the reaction, a strong, exponential increase in the chain length can occur, which can only be controlled with difficulty in the batch mode. Also influencing a once started reaction is difficult.
  • Preferred as a mixer is a micromixer.
  • a fixed bed reactor in the context of the present invention is any reactor which has at least one means for mass transfer between two phases, ie improves the mass transfer between two phases, in particular between two liquid phases compared to an empty reactor, in particular to an empty tube.
  • any device which is known to the person skilled in the art can be used, for example plates, layers, honeycombs, channels etc.
  • the FBR should be designed to help intensify the mass transfer between the two immiscible liquid phases.
  • control and regulation of the entire system including the process data acquisition is at least partially, preferably also largely or even completely, automated. Such automation is significantly more difficult for batch mode processes to this extent.
  • mass flow controllers are used to control the liquid streams.
  • suitable conveying means are used, such as pumps or pressurization, with the aid of which the starting components, for example the two liquid, immiscible phases, preferably via a conduit system in the mixer or directly or from the mixer to be fed into the reactor.
  • HPLC pumps are suitable for liquid transport.
  • the flow rates of the individual educt streams should be controlled as precisely as possible.
  • the use of preparative HPLC pumps is preferred.
  • high-pressure pumps are or are used to transport at least one starting material, preferably piston pumps, which produce a precisely determinable flow rate. possible (preferably with a deviation of 0.3% or less).
  • at least two separate piston pumps with a relative deviation in the flow rate of 0.3% or less are used to supply at least two monomers.
  • An advantage of the continuous process according to the invention is also that first solvent can be rinsed through the entire system to either remove oxygen from the system, or to clean the system of other impurities.
  • the starting materials are combined using optional step ii) in a series connection of static mixers.
  • micromixers are used for this purpose. It is possible to perform the mixing process sequentially. Preferably, certain sequences are also observed during the mixing process, which for example consist of the fact that in general the monomers are first mixed with the base and in the next step the optionally used homogeneous catalyst is fed.
  • step i) the mixing point described above can be used for premixing.
  • the mixing point is characterized by a small flow cross-section, a small dead volume or a small internal volume. All this promotes mass transfer and counteracts phase separation.
  • Micromixers can be used as micromixers.
  • Micromixers are characterized by the fact that they also allow the mixing of volumes in the milliliter range, preferably in the microliter range. If microchannels are used, they have a diameter of less than one mm, preferably less than 500 ⁇ m.
  • Preferably used mixers are under the reaction conditions used both pressure resistant and inert in contact with the chemicals used. Stainless steel is preferred as a material for a mixer.
  • step ii) precedes step iii) the apparatus has mixers and FBRs.
  • the apparatus has a small dead volume, ie. H. has a low volume between mixer and FBR, low flow cross-sections and high flow rates between mixer and FBR. These measures counteract a phase separation. Due to the phase separation, the multiphase flow generated in the micromixers can segregate, which is generally undesirable. It is preferred that the multiphase flow generated in the (micro) mixers is transferred into the FBR with as little separation as possible.
  • lines are used between mixer and reactor, they preferably have a diameter of 0.1-2 mm, more preferably between 0.5 and 1 mm. Preferably, these are capillaries.
  • the components known from HPLC chromatography can be used.
  • two or more (fixed-bed) reactors are connected in series, in order thereby to increase the residence time of the educts or of the educt in the reactor. It can in each Reactor each other residence times can be realized, for example, by different dimensions (diameter, length), etc. In the individual reactors can be set the same and different temperatures.
  • Particle sizes for the particle bed used preferably for conveying the mass transfer are in a range from 1 ⁇ m to 2000 ⁇ m, preferably in a range from 50 to 500 ⁇ m, more preferably in a range from 150 to 300 ⁇ m.
  • a slightly larger average particle size is not excluded, especially if the process is carried out, for example, at higher flow rates.
  • metal particles as bulk material, in particular of Ti or E STAINLESS.
  • Other non-oxidic materials which may be mentioned are carbides and nitrides, in particular SiC, SiN, TiC or TiN. Monoliths or foams of the aforementioned materials are preferred.
  • the FBR can be arranged in any spatial direction. In a preferred embodiment, however, it is arranged vertically, so that the liquid stream can flow through the reactor from top to bottom ("down-flow") or else from bottom to top (“up-flow”). Preferably, the process is carried out in such a way that the reactor is run from the bottom to the top (“up-flow”). is flowing.
  • the "up-flow” operation has the advantage that - in contrast to the "down-flow” operation - the liquid phases can not "trickle" through the reactor and thus leave parts of the fixed bed “dry". Overall, the "up-flow” operation reduces the risk of phase separation.
  • a flow control for the individual Edukthneströme is possible. It is also a regulation of flow and temperature as a result of the data obtained from the online analysis by feedback conceivable.
  • FT-IR Fullier Transform Infrared Spectroscopy
  • ATR crystal flow cell
  • FT-IR is used to control the conversion of functional groups, especially online during the course of the reaction.
  • Further preferred embodiments of the inventive method comprise at least one of the following further steps: a) heating of the reactor, preferably stepwise heating of the reactor, more preferably in different heating zones along the flow direction with different temperature; b) after the reactor outlet, reaction is stopped by cooling; c) addition of "endcapper" after the reactor exit; d) addition of solvent to reduce the viscosity after the reactor exit; e) addition of further monomers after each reactor section; e) series connection of several reactors; f) Parallel connection for throughput increase.
  • Each monomer may also be a mixture of at least two different monomers.
  • the monomers of the mixture may differ with respect to their functional group and / or their other structure.
  • the stoichiometry of different functional groups is balanced, for example 50:50.
  • Fig. 1 shows a flow chart with the basic scheme of the method according to the invention (see the list of reference numerals at the end of the examples);
  • Fig. 5 shows experimental results obtained for a polymerization reaction conducted in a batch reactor; the y-axis indicates the average molecular weight of the polymerization reaction and the x-axis indicates the reaction time;
  • FIG. 6 shows experimental results obtained by continuous processes using a capillary reactor (B, C) and the inventive FBR (A); the y-axis indicates the average molecular weight of the polymerization reaction and the x-axis indicates the reaction time;
  • Fig. 1 1 shows the flow chart of an arrangement of three series-connected continuously operated reactors with fixed beds
  • FIG. 4 shows two possible embodiments of reactors (030) which can be used for the method according to the invention, an overview sketch and a sectional drawing being shown for each individual one of these reactors.
  • the reactor shown in Figure 2 on the left has a smaller length to diameter ratio than the reactor on the right.
  • the reactor tubes (0301) are provided, for example, via threaded connection parts (071, 072 and 073) are connected to conduit sections (07 '), the screw connections being sealed with seals (074' and 074 ").
  • the FBR according to the invention works much more efficiently: With a residence time of only 7 minutes, significantly higher molecular weights than in the capillary reactor are achieved at 60 minutes. At a reaction temperature of 98 0 C, a molecular weight of about 120,000 g / mol is achieved. In addition, a strong dependence of the molecular weight on the temperature can be seen: rising temperature leads to a significant increase in the molecular weight. Without specifying a particular mechanism, it can be assumed that the bulk material reactor works more efficiently because the mass transfer between the organic and aqueous phases is intensified.
  • the flow pattern corresponds in principle to the flow pattern, which is achieved in a capillary of the same diameter directly after a micromixer.
  • FIG. 12 shows a further development of the device as shown in FIG. 11, wherein the structure and process guidance up to the reactor (032) are identical to the arrangement described with reference to FIG. In addition to the arrangement described in FIG. 11, however, the product leaving the third reactor (032) becomes in a fourth reactor (033) with a second endcapper E02 applied, thus saturating the other end group in continuous operation.
  • the monomers (MOl, M02,...) Of the one monomer template (100) each have the same functional group but differ physically and / or chemically from each other. It is further preferred that the monomers (M 10, MI 1,...) Of the at least one further monomer master (101) have a different functional group than the monomers of the first monomer master (100).
  • two or more different monomers are present per monomer master, these can also be mixed, if desired, in a mixer (023) before they are fed to a reactor.
  • Different monomers from two different monomer templates (100) and (101) can also be mixed in a micromixer (020) before entering a reactor and / or mixed with further components from the corresponding templates, for example with a base (BOl). and / or a catalyst (COl).
  • a base base
  • COl catalyst
  • the addition of an endcappers (EOl) is also possible at this time.
  • At the outlet of the last reactor of the plant for the sequential synthesis of polymers is preferably a multiport valve (090), which preferably has a sample loop (090 ') for taking samples.
  • the plant for the sequential synthesis of polymers described in the present embodiment preferably also comprises a positioning device with which many different samples of a predetermined size can be taken out sequentially.
  • a positioning device with which many different samples of a predetermined size can be taken out sequentially.
  • an arrangement (library) of samples (1 10) is preferably produced.
  • the system for the sequential synthesis of polymers has at least one pressure control and / or at least one flow control and / or at least one temperature control (in Figure 14, only the pressure control is shown).
  • radicals R which may be identical or different, there are no restrictions whatsoever.
  • the conversion with respect to polymer given in the present examples is only an example.
  • the conversion can be in the range of 10 g / h to 10 kg / h, preferably 100 g / h to 1 kg / h.
  • the solution is heated to 87 ° C internal temperature under inert gas, and then 2.2 mg (lO ⁇ mol) of palladium acetate and 9.1 mg (60 .mu.mol) of tris-o-tolylphosphine dissolved in 1 ml of the solvent mixture was added.
  • the reaction mixture is refluxed for 2 h in a batch process until the desired viscosity is reached.
  • molecular weights of 3 ⁇ 10 5 g / mol can be achieved in this mode of operation, even after an average VWZ of approximately 17 minutes.
  • such high molecular weights can be achieved constantly over a long period of time (here: at least 200 minutes).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Physical Or Chemical Processes And Apparatus (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)

Abstract

L'invention concerne un procédé pour créer des composés couplés aryle-aryle. Durant ce procédé en continu, au moins deux phases liquides (MOl) et (BOl) non miscibles entre elles sont d'abord éventuellement mélangées dans un malaxeur (020), puis la réaction est réalisée en continu dans un réacteur à lit fixe (030), avant la réalisation éventuelle d'une analyse en ligne (060) des produits (POl).
EP06829097A 2005-11-23 2006-11-22 Procede pour creer des composes couples aryle-aryle Withdrawn EP1965901A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102005055866A DE102005055866A1 (de) 2005-11-23 2005-11-23 Verfahren zur Herstellung von Aryl-Aryl gekoppelter Verbindungen
PCT/EP2006/011202 WO2007059946A2 (fr) 2005-11-23 2006-11-22 Procede pour creer des composes couples aryle-aryle

Publications (1)

Publication Number Publication Date
EP1965901A2 true EP1965901A2 (fr) 2008-09-10

Family

ID=37882550

Family Applications (1)

Application Number Title Priority Date Filing Date
EP06829097A Withdrawn EP1965901A2 (fr) 2005-11-23 2006-11-22 Procede pour creer des composes couples aryle-aryle

Country Status (5)

Country Link
US (1) US20100216964A1 (fr)
EP (1) EP1965901A2 (fr)
JP (1) JP2009516716A (fr)
DE (1) DE102005055866A1 (fr)
WO (1) WO2007059946A2 (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PT1776181E (pt) 2004-01-26 2014-01-02 Harvard College Sistema e método para o fornecimento de fluidos
EP1676632A1 (fr) 2004-12-28 2006-07-05 Covion Organic Semiconductors GmbH Procédé pour la préparation de polymères
JP5222632B2 (ja) * 2008-06-13 2013-06-26 白鳥製薬株式会社 ビアリール化合物の製造方法
ES2741001T3 (es) 2013-03-13 2020-02-07 Opko Diagnostics Llc Mezcla de fluidos en sistemas fluídicos
JP6929773B2 (ja) 2014-12-12 2021-09-01 オプコ・ダイアグノスティクス・リミテッド・ライアビリティ・カンパニーＯｐｋｏ Ｄｉａｇｎｏｓｔｉｃｓ，Ｌｌｃ 成形によって形成される流体システムを含む培養チャネルを備える流体システム
US9481764B1 (en) 2015-10-13 2016-11-01 The Boeing Company Flow reactor synthesis of polymers
GB2571696B (en) 2017-10-09 2020-05-27 Compass Pathways Ltd Large scale method for the preparation of Psilocybin and formulations of Psilocybin so produced
JP7075247B2 (ja) * 2018-03-19 2022-05-25 東レエンジニアリング株式会社 リアクタ
CN110961060A (zh) * 2018-09-30 2020-04-07 中国石油化工股份有限公司 微通道反应器
CA3138094A1 (fr) 2019-04-17 2020-10-22 Compass Pathfinder Limited Procedes de traitement des troubles de l'anxiete, des troubles de la cephalee et des troubles de l'alimentation au moyen de psilocybine
CN110732298B (zh) * 2019-11-21 2024-02-23 温州国仕邦高分子材料有限公司 微波辐射连续式水性树脂合成管道反应器
JP2022163533A (ja) * 2021-04-14 2022-10-26 オルガノ株式会社 白金族金属担持触媒カラムおよび炭素－炭素結合形成方法

Family Cites Families (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1224640B (it) * 1987-11-20 1990-10-18 Vittorio Ragaini Procedimento per la realizzazione di reazioni chimiche in sistemi polifasici e relativa apparecchiatura.
DE4426671A1 (de) * 1994-07-28 1996-02-01 Hoechst Ag Verfahren zur Kreuzkupplung von aromatischen Borverbindungen mit aromatischen Halogenverbindungen oder Perfluoralkylsulfonaten
US6001229A (en) * 1994-08-01 1999-12-14 Lockheed Martin Energy Systems, Inc. Apparatus and method for performing microfluidic manipulations for chemical analysis
DE19816886C2 (de) * 1998-04-17 2001-06-07 Axiva Gmbh Verfahren und Vorrichtung zur kontinuierlichen Herstellung von Polymerisaten
DE19925384A1 (de) * 1999-06-02 2000-12-07 Oxeno Olefinchemie Gmbh Verfahren zur katalytischen Durchführung von Mehrphasenreaktionen, insbesondere Hydroformylierungen
DE19927554C2 (de) * 1999-06-16 2002-12-19 Inst Mikrotechnik Mainz Gmbh Mikromischer
GB2359765B (en) * 2000-03-02 2003-03-05 Univ Newcastle Capillary reactor distribution device and method
DE10020630A1 (de) * 2000-04-27 2001-11-08 Merck Patent Gmbh Verfahren zur Oxidation von tertiären Aminen und Stickstoff-haltigen aromatischen Heterocyclen
JP2002273206A (ja) * 2001-03-16 2002-09-24 Mitsubishi Chemicals Corp 合成反応装置及びそれを用いる合成反応方法
US7010391B2 (en) * 2001-03-28 2006-03-07 Handylab, Inc. Methods and systems for control of microfluidic devices
WO2002078842A1 (fr) * 2001-03-30 2002-10-10 Council Of Scientific And Industrial Research Nouvelle formulation catalytique et sa preparation
US6880576B2 (en) * 2001-06-07 2005-04-19 Nanostream, Inc. Microfluidic devices for methods development
DE20113127U1 (de) * 2001-08-14 2001-10-18 Berger, Bruno, Braunau Schrägrohrreaktor
GB0125622D0 (en) * 2001-10-25 2001-12-19 Cambridge Display Tech Ltd Method of polymerisation
DE10159946A1 (de) * 2001-12-06 2003-06-18 Covion Organic Semiconductors Prozess zur Herstellung von Aryl-Aryl gekoppelten Verbindungen
DE60308698T2 (de) * 2002-08-15 2007-08-23 Velocys, Inc., Plain City Verfahren in mikrokanalreaktoren mit gebundenem katalysator und einen gebundenen katalysator oder gebundene chirale hilfsmittel enthaltende systeme
DE10241814A1 (de) * 2002-09-06 2004-03-25 Covion Organic Semiconductors Gmbh Prozeß zur Herstellung von Aryl-Aryl gekoppelten Verbindungen
SK285692B6 (sk) * 2002-11-26 2007-06-07 Novácke Chemické Závody, Akciová Spoločnosť Zariadenie tvaru dvoch súosových stojatých valcovpre podmienky chemických technológií a spôsob jeho využitia
US6979751B2 (en) * 2002-12-23 2005-12-27 Eastman Chemical Company Processes for the preparation of higher molecular weight ketones
US7178386B1 (en) * 2003-04-10 2007-02-20 Nanostream, Inc. Parallel fluid processing systems and methods
KR20100038476A (ko) * 2004-11-16 2010-04-14 벨로시스, 인코포레이티드 마이크로채널 기술을 사용하는 다중상 반응 과정
DE602005019629D1 (de) * 2004-12-16 2010-04-08 Exxonmobil Chem Patents Inc Verfahren zur herstellung substituierter metallocenverbindungen zur olefinpolymerisierung
EP1676632A1 (fr) * 2004-12-28 2006-07-05 Covion Organic Semiconductors GmbH Procédé pour la préparation de polymères
US7547757B2 (en) * 2006-08-01 2009-06-16 Headwaters Technology Innovation, Llc Methods for manufacturing aryl-aryl coupled polymers
US20080076049A1 (en) * 2006-09-26 2008-03-27 Xerox Corporation Arylamine processes

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2007059946A2 *

Also Published As

Publication number Publication date
WO2007059946B1 (fr) 2007-09-20
WO2007059946A3 (fr) 2007-08-02
US20100216964A1 (en) 2010-08-26
WO2007059946A2 (fr) 2007-05-31
DE102005055866A1 (de) 2007-05-24
JP2009516716A (ja) 2009-04-23

Similar Documents

Publication Publication Date Title
EP1965901A2 (fr) Procede pour creer des composes couples aryle-aryle
EP2403633B1 (fr) Mélangeur statique compact coaxial et son utilisation
Bennett et al. Microfluidic synthesis of elastomeric microparticles: A case study in catalysis of palladium‐mediated cross‐coupling
EP3134201B1 (fr) Réacteur agitateur à plusieurs étages avec un mélange de retour réduit
EP3154674B1 (fr) Chambre de réaction pour un réacteur chimique et réacteur chimique construit à partir de celle-ci
EP2349552A1 (fr) Réacteur modulaire
Zarkadas et al. Antisolvent crystallization in porous hollow fiber devices
EP2046493B1 (fr) Dispositif et procédé de manipulation de mélanges à composants multiples
EP2915581B1 (fr) Mélangeur statique
DE102004003925A1 (de) Universeller kontinuierlich betriebener Säulenreaktor für chemische Synthesen vom Labor- bis in den Pilotmaßstab
WO2018115443A1 (fr) Production d'un oxyde d'amine par oxydation d'une amine tertiaire
DE102005002336A1 (de) Verfahren zur Durchführung von kontinuierlichen Olefin-Ringschluss-Metathesen in komprimiertem Kohlendioxid
DE10031380A1 (de) Verfahren zur Übertragung von Alkyliden-Gruppen auf organischen Verbindungen
DE19816921A1 (de) Verfahren für kontinuierliche polymeranaloge Umsetzungen
RU2397805C2 (ru) Проточное лабораторное устройство для гидрирования и лабораторный способ гидрирования с использованием этого устройства
CH705823A2 (de) Mit einem Wärmetauscher versehener Kreislaufreaktor.
EP1246784B9 (fr) Reaction de composes carbonyle avec des reactifs organo-metalliques
Engl et al. A droplet-based high-throughput tubular platform to extract rate constants of slow chemical reactions
WO2006039895A1 (fr) Reacteur microcapillaire et procede de melange controle de fluides miscibles de maniere non homogene a l'aide de ce reacteur microcapillaire
DE10015518A1 (de) Verfahren zur Oximierung organischer Carbonylverbindungen und/oder CH-acider Verbindungen
WO2001074758A1 (fr) Procede pour la transposition de beckmann d'oximes organiques
EP1268485A1 (fr) Procede de cycloaddition 1,3-dipolaire de composes organiques dans un microreacteur
EP1439905A1 (fr) Procede de production de (co)polymeres a partir de monomeres olefiniquement insatures
JP2008006358A (ja) 微粒子製造方法
DE10026646A1 (de) Verfahren zur Herstellung von Indolen

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20080617

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU LV MC NL PL PT RO SE SI SK TR

RIN1 Information on inventor provided before grant (corrected)

Inventor name: ZECH, TORSTEN

Inventor name: LAUS, OLIVER

Inventor name: HUERTGEN, DENIS

Inventor name: KOECHEL, OLIVER

Inventor name: KAISER, GUNILLA

17Q First examination report despatched

Effective date: 20090330

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: BASF SE

DAX Request for extension of the european patent (deleted)
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20170601