WO2020044359A1 - Micro-réacteur multiphase à double fonction - Google Patents

Micro-réacteur multiphase à double fonction Download PDF

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Publication number
WO2020044359A1
WO2020044359A1 PCT/IN2018/050780 IN2018050780W WO2020044359A1 WO 2020044359 A1 WO2020044359 A1 WO 2020044359A1 IN 2018050780 W IN2018050780 W IN 2018050780W WO 2020044359 A1 WO2020044359 A1 WO 2020044359A1
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reaction
phase
dual function
liquid
microreactor
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PCT/IN2018/050780
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English (en)
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Ganapati Dadasaheb Yadav
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Ganapati Dadasaheb Yadav
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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
    • 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
    • B01J2219/00792—One or more tube-shaped elements
    • 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
    • B01J2219/00891—Feeding or evacuation
    • B01J2219/00894—More than two inlets
    • 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
    • B01J2219/00907—Separation using membranes
    • 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

Definitions

  • the invention relates to microreactor for conducting multiphase reaction. More specifically, the present invention provides a dual function multiphase microreactor having microfluidic flow design to carry out reaction involving an immiscible phases, preferably for at least two or three immiscible phases for example to carry out reaction involving in a phase transfer catalyst reaction.
  • the said multiphase microreactor enables to carry out continuous multiphase reaction and simultaneously phase separation therein. Hence the said microreactor provides faster reaction rate, higher conversion rate, selectivity including separation and reusability of catalyst phase or any phases therein.
  • Multiphase reactions such as liquid-liquid-liquid phase reactions in a tank reactor which are carried out at the interface of two immiscible liquids to form a new product can be advantageous in terms of improved reaction kinetics, higher yields, and selectivity.
  • Such type of reactions is utilized in manufacturing of many agricultural chemicals, pharmaceuticals, and other specialty chemicals and intermediates.
  • the presence of the liquid-liquid interface can accelerate the reaction, the interface between hydrophilic and hydrophobic liquids can be used to combine immiscible reaction partners or to protect sensitive partners, from hydrolysis for example or a phase-transfer catalyst is employed to draw the reaction in one phase of choice (liquid-liquid-liquid three phase reaction).
  • phase transfer catalyst PTC
  • multiphase PTC reaction contain upper organic phase, middle catalyst rich phase and lower aqueous phase.
  • the middle phase is the catalyst-rich phase, with two interfaces on either side, namely aqueous phase-middle catalyst phase and organic phase -middle phase.
  • the formation and stability of the middle phase depend on the phase equilibrium-hydrophilic and lipophilic balance, density difference and temperature.
  • the middle phase contains majority of the catalyst along with some of the organic solvent, aqueous nucleophile and trace quantity of water.
  • the operating conditions for the formation of middle phase include type and quantity of phase transfer catalyst, type and quantity of aqueous reactants, reactant and product in organic phase, quantity of base, quantity of inorganic salts and reaction temperature.
  • Newmann et al. (1984) discovered role of polyethylene glycol as a phase transfer catalyst for the isomerization of allyl anisole under triphasic reaction conditions. They obtained three phase reaction mixture by using 60% aqueous KOH with toluene and catalytic amount of PEG-400. Weng et al. (1988) studied the role played by middle liquid phase in L-L-L phase transfer catalysis and observed that addition of phase transfer catalyst beyond a critical amount leads to a sharp increase in the reaction rate.
  • phase transfer catalysis is conducted in dispersed-phase systems wherein a three-phase mixture containing a phase transfer catalyst or PTC is stirred vigorously in a tank or other vessel (Batch Reaction) to form an agitated interface or micro droplets dispersion.
  • Batch Reaction a three-phase mixture containing a phase transfer catalyst or PTC is stirred vigorously in a tank or other vessel (Batch Reaction) to form an agitated interface or micro droplets dispersion.
  • the overall rate of conversion initially increases with stirring speed, since increasing the stirring speed causes the formation of greater numbers of smaller drops with higher interfacial areas.
  • the conversion rate plateaus with increased stirring speed, as the heterogeneous reaction system undergoes a transition from mass-transfer control to bulk organic -phase kinetic control.
  • US7,604,78l discloses multi-phase PTC reactions conducted in microchannel apparatus comprise of at least one separation assist feature selected from the group consisting of: an expansion zone in the separation zone that is connected to a reaction channel and has a larger internal cross-sectional area than the reaction channel, a phase coalescence element, and a separator plate.
  • US 4,754,089 disclose a method for conducting phase transfer catalysis reaction in a multiphase reaction system wherein the different phases are separated by a membrane permeable to the phase transfer catalyst.
  • PTC reaction of the interest is a displacement reaction. Under these conditions, much less than stoichiometric quantities of catalyst is utilized/deactivated, because the catalyst can continually shuttle back and forth between phases, carrying fresh reactant into the organic phase/aqueous phase with it. It is foreseeable in the practice of this invention that the phase transfer catalyst is active for longer time and can be utilized for continuous reaction processes even in micro reactor systems. Whereas, in plate separator or membrane separator forms available in prior art apparatuses, the catalyst recovering or separation from organic or aqueous phase is a major problem. Other disadvantages of available microreactor include small reaction path length. There is no single attempt is made to develop microreactor with separation of PTC catalyst from multiphase or liquid-liquid-liquid PTC reaction while performing continuous reaction.
  • a dual function microreactor having microfluidic flow for multiphase reaction which provides long reaction path for continuous reaction and keeping reaction phases separated from each other to ensure more effective phase separation at the end of reaction treatment path for a given residence time.
  • the new reactor is successfully separating middle active catalyst phase and can be utilise without further post-treatment for recirculation to carry out new reaction, as middle phase is totally kept in between the organic and water phase thought out the reaction without disturbing the interfaces or forming droplets dispersion.
  • the primary objective of the present invention aims to develop and design a microreactor for multiphase reaction involving a one or two immiscible phases.
  • One more objective of the present invention is to provide a microreactor for reaction involving a phase transfer catalyst, wherein the reactor enables to conduct firstly the continuous chemical reaction instead of batch reaction and second, perform a phase separation simultaneously without stopping the reactor.
  • Next objective of the present invention is to provide a microreactor for multiphase reaction which will reduce the impurity level in final product.
  • One more objective of the present invention is to provide a microreactor, that will keep the phase transfer catalyst active for longer time and can be utilized for continuous reaction processes or reuse for several cycles.
  • Another objective of the invention is to continuously reuse middle catalyst phase without any treatment. Further another objective of the invention is to find out mass transfer coefficient of each phase.
  • Yet another obj ective of the invention is to reuse aqueous phase, organic phase and/or catalyst phase.
  • the present invention aims to provide a microreactor having microfluidic flow paths capable of performing multiphase reaction using two or more immiscible phases, wherein the said microreactor offers continuous process for such multiphase reactions and each phase is separated by permeable membranes so that to keep the phases separated throughout reaction.
  • the present invention also aims to allow for continuous collection of each phase and recirculation of any one or all phases through same reaction device for reusability.
  • the present invention provides a dual function, continuous flow microreactor device (100) for two/multiphase reaction comprising of:
  • Applicants a three-fluid path stacked in layer for each different chemical phases; providing a laminar flow of each phase flowing from inlet conduits (4, 5 and ⁇ ) through the stacked paths separated by said membrane and coming out without mixing from outlet conduits (11, 15 and 19), allowing two phase transport of reactant and product via diffusion through membrane placed at phase interfaces and thereby increasing selective reaction and keeping phases separated while performing liquid-liquid-liquid, gas-liquid-liquid, fluid-liquid-liquid reaction.
  • this dual function microreactor is further configured to back pressure regulator (14, 18 and 22) to exert a pressure for diffusion through membrane.
  • microchannels are provided in zic-zac or S-shape to cover maximum area of plate and maximum path length to increase residence time of reactant.
  • the said plates are made from material selected from Polytetrafluoroethylene, stainless steel, glass, hastelloy and selection of membranes depend upon the hydrophilicity and lipophilicity of reacting molecule and product thereof.
  • Figure No. 1 Schematic view of microcontroller showing various embodiment of it as per present invention.
  • Figure No. 2 Illustrated the view of the fluidic channels and flow inlet and outlet itched on plain surface of top (lb), middle (lc) and bottom (la) plate.
  • Figure No. 3 Illustrated the (a) cross-view of the fluidic channels on plain surface of top (lb), bottom (la) plate and (b) cross-view of the fluidic channels on plain surface of middle (lc).
  • Figure No. 4 Depict cross section view of microreactor as per present invention.
  • Figure No. 5 Schematic view of a reaction unit including layering of plurality of plates and membranes.
  • Figure No. 6 Depict a phase transfer reaction having transfer of reactant, product and catalyst molecular involved in phase transfer reaction as discussed in example 1
  • Microreactor offers many advantages over batch reactor which include suitability for handling hazardous reactions because of vastly reduced hold-up of dangerous reactants and solvents. Mixing is done by diffusion which is very fast comparing to achieve by turbulence in a batch reactor. High surface to volume ratio of microreactor gives much better heat exchange capability and is highly suitable for exothermic and runaway type of reactions. By numbering -up microreactor units on demand production and portability can be easily achieved.
  • the present invention provides a dual function multiphase microreactor with continuous flow mechanism for carrying out at least three liquid phase chemical reaction having three fluidic channels for each phase with at least two membrane separator sandwiches between three fluidic channels to ease of phase separation.
  • reaction and phase separation occur simultaneously.
  • the present invention provides a dual function, continuous flow microreactor device (100) for two/multiphase reaction comprising of:
  • each plate is having plurality of notches configured to fasten
  • Applicants a three-fluid path stacked in layer for each different chemical phases; providing a laminar flow of each phase flowing from inlet conduit (4, 5 and ⁇ ) through the stacked paths separated by said membrane and coming out without mixing from outlet conduits (11, 15 and 19), allowing two phase transport of reactant and product via diffusion through membrane placed at phase interfaces and thereby increasing selective reaction and keeping phases separated while performing liquid-liquid-liquid, gas-liquid-liquid, fluid-liquid-liquid reaction.
  • microreactor device (100) for three phase reaction comprising
  • each plate is having plurality of notches configured to fasten
  • each plate is having plurality of notches configured to fasten each plate together.
  • the said reactor is further configured to back pressure regulator (14, 18 and 22) to exert a pressure for diffusion through membrane.
  • top (lb), middle (lc) and bottom (la) plates are having microchannels disposed on plain surface.
  • the fluidic microchannel disposed on bottom plate (la) and top plate (lb) is semi circular half-channel with one side open on plain surfaces.
  • fluidic microchannel disposed on middle plate (lc) is open channel with both side open on plain surfaces.
  • the channel/groove is prepared isotropically etching into a flat substrate, resulting in a semi-circular half-channel or Open channel (or a rectangle with rounded comers) having width in the range from 0.1 to 1000 pm.
  • the material of plates are selected from Polytetrafluoroethylene and stainless steel, glass, quartz, hastelloy.
  • the term “groove,” as used herein, should be understood to mean a surface feature that has been formed into the surface of an object, that does not penetrate completely through the object, and applies to components of prior art chemical reactors.
  • the plates having openings at both the end (4’, I F, 5’, 15’, 6' and 19’) of microchannel therein for circulation of reaction phase from one end to another end.
  • microchannels are provided in S-shape or any other suitable curves to cover maximum area on plates and maximum path length to increase residence time of reactant.
  • microreactor wherein the said microreactor plates and each plate is having plurality of notches (7) configured to fasten each plate together in layer and touching each other the plates having no openings/space therein for circulation or mixing of any phase flowing through each plate’s microchannel.
  • a key feature of the present invention is the stacking of three plates and two membranes.
  • the openings in each plates in accord with the present invention are configured and oriented to manipulate a laminar flow of fluid in three stacked microchannels in a reactor to achieve a desired result.
  • the manipulation will result in an enhancement of a quantity or a quality of a chemical product produced in Such a reactor.
  • Additional product can be generated by a phase transfer phenomenon while reacting in multiphase reaction by including a passage to reacting molecule from one phase to other phase / from top and bottom phase to middle phase by permeable membranes disposed at the phase interphases that define a selectivity of product in a reaction channels.
  • Higher levels of product can be produced by including more path length or by controlling pressure of fluids to optimise a diffusion rate.
  • a view of plurality of stacked plates and membranes sandwich between two adjacent plate the said membranes are having selective permeability to molecules selected from hydrophobic and hydrophilic, that enable a reactor to exchange of reactant and product from one phase to other phase or enables selectively transfer of one reaction molecule from between the phase interphases.
  • the type pf membranes are selected and not limiting to hydroxylated nylon and polytetrafluoroethylene. And group of ceramic membrane, stainless steel membrane, metal oxide membrane. Additional sealed interfaces that would otherwise be presented if tubing, connectors, valves or other fluid handling hardware are possibly couple the fluidic microstructures or conduits thereof.
  • the present invention is related to dual function microreactor to carry out multiphase PTC reaction accomplished by membrane for phase separation and pumps for recirculation of all phases including catalyst phase.
  • the present invention allows continuous reuse of catalyst without any disturbance or shutdown of the process.
  • the present invention focuses on the design and development of novel dual functional microreactor which has been used to intensify chemical processes by synergistically combining chemical reaction with phase separation for multiphase PTC reactions.
  • the dual functional microreactor has the additional benefit of enhancing the selectivity of the desired product through manipulation of various parameters such as flow rate, mole ratio and temperature.
  • the present invention provides a method of operating the dual function microreactor (100) as illustrated accompanied herewith.
  • the method comprises of following steps:
  • a technical advantage of the present invention includes micro-reactor with membranes for simultaneous reaction and separation of three phases. Another advantage includes higher conversion and selectivity, in shorter periods of time, compared to batch process.
  • the middle catalyst phase is collected separately which can be continuously reused without any treatment.
  • the aqueous phase is also reused after making up reactant concentration with fresh reactants.
  • the lower aqueous phase is selected from group of aqueous phase reactant, base, inorganic salt, small amount of catalyst and water.
  • Base used is any water soluble alkali preferably sodium hydroxide (NaOH), potassium hydroxide (KOH) and inorganic salt like sodium chloride (NaCl), sodium bromide (NaBr), potassium chloride (KCl)and potassium bromide (KBr).
  • the upper organic phase is selected from group organic phase reactant, organic solvents. Solvent should be immiscible preferably toluene, cyclohexane and 1- chlorooctane.
  • the middle catalyst phase is selected from group ammonium salts like tetra butyl ammonium bromide (TBAB), tetra methyl ammonium bromide (TMAB), butyl triethyl ammonium chloride (BTEAC1), Polyethylene glycol (PEG3000-20000), crown ether, phosphonium salts like ethyl triphenylphosphonium bromide (ETPB), Tetra Phenyl Phosphonium Bromide(TPPB) are used as phase transfer catalyst.
  • group ammonium salts like tetra butyl ammonium bromide (TBAB), tetra methyl ammonium bromide (TMAB), butyl triethyl ammonium chloride (BTEAC1), Polyethylene glycol (PEG3000-20000), crown ether, phosphonium salts like ethyl triphenylphosphonium bromide (ETPB), Tetra Phenyl Phosphonium Bromide(TPPB) are used
  • the reactor disclosed in the present invention can be useful to conduct various PTC reactions in micro channels like displacement reaction, C-alkylation reaction, O- alkylation reaction, N-alkylation reaction, S-alkylation reaction, oxidation reaction, reduction reaction, isomerization reaction, dehydrohalogenation reaction etc.
  • the continuous flow is achieved by means of controlling pump operated to feed aqueous, organic and catalyst phase.
  • flow rate and back pressure regulators are adjusted in such way that it maintains all three phases in parallel flow and pressure difference gradient condition.
  • the economic potential of the present invention includes continuous reuse catalyst without any treatment and continuous process for conducting multiphase PTC reaction at volume of micro litre level. It should be understood that the invention is not restricted to the embodiment which has been described herein but covers all variants immediately accessible to a man skilled in the art.
  • the method and the installation according to the invention can be used for the carrying out of any two or more phase chemical reaction under pressure in the presence of a gas phase, a liquid phase and a third phase which may, according to the case, be a liquid or a solid or slurry containing fine particles.
  • the hydrophilic or hydrophobic can be placed at the interface of liquid phase if desired for particular reaction.
  • microreactor as claimed in present invention was suitably used to overcome this problem and the mass transfer coefficients can be independently controlled by independently controlling flow in the channels and selecting a specific membrane polarity for interested product or to reduce the impurity.
  • the dual functional microreactor has additional benefit of enhancing the selectivity of the desired product through manipulation of various parameters such as catalyst quantity, flow rate, mole ratio and temperature.
  • An accompanied Figure 6 illustrated the cross sectional view of micro reactor, wherein the dual functional microreactor which simultaneously perform multiphase reaction as well phase separation comprises of three fluidic channels for organic (Channel A), middle PTC catalyst phase (Channel B) and aqueous phase (Channel C). Further, it comprises at least two membranes E and F having hydrophilic or hydrophilic properties. The said membranes are sandwich between adjacent phases. More preferably, hydrophilic membrane is sandwich between the aqueous phase and the catalyst phase channel and a hydrophobic membrane is sandwich between the organic phase and catalyst phase channel.
  • the material of construction of channel is preferably selected from Polytetrafluoroethylene (PTFE), Polyether ether ketone (PEEK) or stainless steel.
  • PTFE Polytetrafluoroethylene
  • PEEK Polyether ether ketone
  • the hydrophilic and hydrophobic membranes were specially prepared.
  • the thickness of hydrophilic membrane was 100 pm with pore size of 0.1 pm.
  • the thickness of hydrophobic membrane was 100 pm with pore size of 0.2 pm.
  • the volume and length of the top and bottom channels were 8.27 pl and 11.82 cm respectively.
  • the volume and length of the middle channel were 10.1 pl and 14.43 cm respectively.
  • the experimental setup as per present invention contains three pumps from which the three different phases were pumped and fed directly into the three inlet ports of the microreactor.
  • the three outlets of the microreactor were fed into the inlet of back pressure regulator (BPR) of pressurization module and the outlet of the BPR in turn was fed into the collection module.
  • BPR back pressure regulator
  • the three phases were separated and pumped to the microreactor separately and a typical reaction was conducted at 25°C, flow rate of the organic and aqueous phase were 30 pl/min and that of middle phase was 20 m ⁇ /min, pressure across the hydrophilic and hydrophobic membranes were 480 mbar and 460 mbar respectively.
  • Three phases were pumped independently and the catalyst rich middle phase, which was coming out of the pressurization module, was recirculated back to the feed vessel of the middle phase. Sample analysis was done by GC.
  • the three phases were separated and pumped to the microreactor separately and a typical reaction was conducted at 25°C, flow rate of the aqueous phase was 250 m ⁇ /min, middle phase was 250 pl/min, and organic phase 10 pl/min. Pressures across the hydrophilic and hydrophobic membranes were 480 and 460 mbar, respectively. Three phases were pumped independently and the catalyst rich middle phase, which was coming out of the pressurization module, was recirculated back to the feed vessel of the middle phase. Sample analysis was done by GC.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un micro-réacteur pour réaliser une réaction multiphase. Plus spécifiquement, la présente invention concerne un micro-réacteur multiphase à double fonction comprenant des plaques empilées ayant des canaux microfluidiques et un sandwich de membrane de diffusion entre les plaques adjacentes pour effectuer une réaction impliquant une phase non miscible, de préférence pour au moins deux ou trois phases non miscibles, par exemple pour effectuer une réaction impliquant une réaction de catalyseur de transfert de phase. Ledit micro-réacteur multiphase permet d'effectuer une réaction multiphase continue et une séparation de phase simultanée à l'intérieur de celui-ci. Par conséquent, ledit micro-réacteur fournit une vitesse de réaction plus rapide, un taux de conversion plus élevé, une sélectivité comprenant la séparation et la réutilisation de la phase de catalyseur ou de n'importe quelle phase à l'intérieur de celle-ci.
PCT/IN2018/050780 2018-08-25 2018-11-24 Micro-réacteur multiphase à double fonction WO2020044359A1 (fr)

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IN201821031887 2018-08-25
IN201821031887 2018-08-25

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Cited By (3)

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Publication number Priority date Publication date Assignee Title
CN113926402A (zh) * 2020-06-29 2022-01-14 中国石油化工股份有限公司 一种微通道反应器及其应用
CN114849614A (zh) * 2022-05-24 2022-08-05 山东绿色海洋化工研究院有限公司 一种利用微反应系统制备高级卤代脂肪烃的微反应方法
CN115253954A (zh) * 2022-08-05 2022-11-01 中国石油天然气股份有限公司 一种连续反应装置及应用

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113926402A (zh) * 2020-06-29 2022-01-14 中国石油化工股份有限公司 一种微通道反应器及其应用
CN113926402B (zh) * 2020-06-29 2023-04-07 中国石油化工股份有限公司 一种微通道反应器及其应用
CN114849614A (zh) * 2022-05-24 2022-08-05 山东绿色海洋化工研究院有限公司 一种利用微反应系统制备高级卤代脂肪烃的微反应方法
CN114849614B (zh) * 2022-05-24 2023-11-03 山东绿色海洋化工研究院有限公司 一种利用微反应系统制备高级卤代脂肪烃的微反应方法
CN115253954A (zh) * 2022-08-05 2022-11-01 中国石油天然气股份有限公司 一种连续反应装置及应用
CN115253954B (zh) * 2022-08-05 2024-04-16 中国石油天然气股份有限公司 一种连续反应装置及应用

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