CN100510742C - Negatively pressurized sampling micro fluidics chemical synthesis reaction system - Google Patents
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- CN100510742C CN100510742C CNB2006100531400A CN200610053140A CN100510742C CN 100510742 C CN100510742 C CN 100510742C CN B2006100531400 A CNB2006100531400 A CN B2006100531400A CN 200610053140 A CN200610053140 A CN 200610053140A CN 100510742 C CN100510742 C CN 100510742C
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Abstract
The provided negative-pressure micro-flow (mu L/min level) control chemical reaction system comprises: a public negative pressure source, an electric heat plate, a micro-regulation valve, a container for the product, and an interface. This invention is simple and convenient to operate and control reaction condition.
Description
Technical field
The present invention relates in micro-fluidic reactor, carry out the technology and the device of organic synthesis, particularly relate to a plurality of reactants of control with the low discharge of μ L/min level simultaneously by a plurality of micro passage reactions, the condition of the research synthetic reaction in micro-fluidic reactor and improve the apparatus and method of synthetic reaction productive rate.
Background technology
In recent years, field such as research chemical synthesis route and development new drug has been subjected to general attention on micro-fluidic reactor.Because microchannel width and depth ratio are less, it has the unexistent characteristics of conventional glass reaction container, big as specific surface area, molecular diffusion is apart from weak point, thermal capacitance is little, do not need to stir just mass transfer and heat transfer efficiently, can avoid simultaneously in the glass container of routine owing to reactant mixes the inhomogeneous shortcomings such as subsidiary reaction and local overheating that cause.Delivered a first piece of writing behind the document of synthetic compound on the micro passage reaction from 1997, the microfluidic reactor has been used for the synthetic reaction between liquid-liquid and solution-air, shortened the research cycle of developing new drug, novel substance, new material, and it is fast to have reaction velocity, the productive rate height, accessory substance is few, and the reactant consumption is few, characteristics such as the environmental contaminants that produce are few have been showed application prospects.
Because the microchannel width of micro passage reaction is the 20-2000 micron, the degree of depth is about 20-1000, and area is about several square centimeters.In so little micro passage reaction, carry out synthetic reaction, control exactly reactant with the low discharge of μ L/min level by micro passage reaction, be to guarantee reactant reaction time and improve the key of synthetic reaction productive rate in micro passage reaction.Use a plurality of micro-injection pumps or electroosmotic pump to control reactant at present mostly and pass through the microchannel.But micro-injection pump costs an arm and a leg.The amount of infusion of electroosmotic pump changes with the change of electroosmotic flow, and the surface nature of passage, the pH value that is transferred material, ionic strength etc. all can influence the size of electroosmotic flow, thereby changes amount of infusion, and the too big material of ionic strength can not be carried with electroosmotic pump.
Summary of the invention
The purpose of this invention is to provide a kind of easy to operate, micro-fluidic chemical reaction system (Fig. 1) that reactant flow is adjustable, simple in structure, control exactly reactant with the low discharge of μ L/min level simultaneously by a plurality of micro passage reactions, make reactant be arranged the enough reaction time at micro-fluidic reactor.Overcome present micro-injection pump apparatus expensive and electroosmotic pump amount of infusion and be difficult to control shortcoming.
Micro-fluidic chemical reaction system provided by the invention, by one or more micro-fluidic reactors arranged side by side, a public negative pressure source, and form with the same number of electric hot plate of micro-fluidic reactor, micro-regulating valve, product liquid storage bottle and interface.It is characterized in that, use one negative pressure source to make simultaneously on the micro-fluidic reactor that reactant enters micro-fluidic reactor in the reactant liquid storage tank under atmospheric driving, reactant is mixed at intersection point c place, microchannel, chemical reaction takes place in reaction channel cd, and, reacted product is flowed in the product liquid storage bottle through polyfluortetraethylene pipe by at the interface that is installed on micro-fluidic reactor exit (d).Described public negative pressure source is by a minipump, a negative pressure bottle, and an electric contact vacuum meter is formed.With vacuum tightness in electric contact vacuum meter indication and the control Dewar bottle, the interior vacuum tightness of Dewar bottle is remained in the setting range.In Dewar bottle vacuum tightness be lower than set vacuum tightness following in limited time, electric contact vacuum meter can be controlled the power connection of minipump, by using the air of minipump through polyfluortetraethylene pipe extracting vacuum bottle, make vacuum up in the Dewar bottle, vacuum tightness reaches and sets going up in limited time of vacuum tightness in Dewar bottle, minipump stops automatically, and the interior vacuum tightness of Dewar bottle is remained in the setting range.Micro-regulating valve all is equipped with in being connected that negative pressure bottle and each product liquid storage bottle join on the teflon pipeline, negative pressure by the opening degree of control micro-regulating valve is regulated each product liquid storage bottle respectively reaches and controls the purpose that reactant flows through each micro-fluidic reactor flow velocity respectively.The required temperature of chemosynthesis reaction is controlled with electric hot plate.The present invention uses a kind of interface of particular design to be connected the outlet (d) and the product liquid storage bottle of micro-fluidic reactor with polyfluortetraethylene pipe, the feature of its interface is after being holed with Glass drill head in the exit of micro-fluidic reactor, there is sieve silk of passage at the use center to a side, joint by rib-loop in two polytetrafluoroethylene gaskets and the band, the joint of rib-loop in the band is fixedly mounted in the exit of micro-fluidic reactor, again by a connection sieve silk and a polytetrafluoroethylene gasket of being with center pit, the polyfluortetraethylene pipe that connects the product liquid storage bottle hermetic is connected to the other end of the joint of rib-loop in the band, thereby make the reactant that places a plurality of reactant liquid storage tanks of micro-fluidic reactor under atmospheric promotion, flow to the product liquid storage bottle through reaction channel and interface, and be stored in the product liquid storage bottle.
The quantity of electric hot plate, micro-regulating valve, product liquid storage bottle and interface is identical with micro-fluidic reactor quantity arranged side by side among the present invention.Therefore, can control flow velocity and the temperature of reaction of reactant in reaction channel in each micro-fluidic reactor respectively.
The use step of micro-fluidic chemical reaction system provided by the invention is as follows:
Reactant liquid storage tank (a at micro-fluidic reactor, b) add different reactant solutions in respectively, by setting the minimum and maximum vacuum tightness of electric contact vacuum meter, connect the minipump power supply, make and form negative pressure in the Dewar bottle, prescribe a time limit when vacuum tightness in the bottle reaches to set on the vacuum tightness, electric contact vacuum meter is closed the minipump power supply, prescribe a time limit when vacuum tightness in the bottle is lower than to set under the vacuum tightness, electric contact vacuum meter starts minipump, makes bottle interior vacustat in the scope of setting.Opening degree by the control micro-regulating valve, different reactant flow in the reactant liquid storage tank is gone in the microchannel of micro-fluidic reactor, in c point mixing beginning reaction, and, reacted product is flowed in the product liquid storage bottle by at the interface that is installed on micro-fluidic reactor outlet d place.The required temperature of chemosynthesis reaction can be controlled with electric hot plate, reaction time can use two kinds of methods to regulate: 1. the micro-fluidic reactor that uses the different length microchannel, 2. the opening degree negative pressure of regulating each product liquid storage bottle by the control micro-regulating valve, thus the flow velocity of micro-fluidic reactor is crossed in the conditioned reaction logistics.
Analyze the further analysis of instrument and characterize product in the product liquid storage bottle by chromatogram, mass spectrum, chromatograph-mass spectrometer coupling or nuclear magnetic resonance etc., can obtain the structure of product under the various differential responses conditions and the productive rate of synthetic reaction.Because the required sample size of instruments such as chromatogram, mass spectrum, chromatograph-mass spectrometer coupling or nuclear magnetic resonance seldom, the amount that obtains product in a few minutes inherent product liquid storage bottles just can satisfy the requirement of above-mentioned instrumental analysis.Therefore, saved the consumption of reactant greatly, and the quantity of generation environmental contaminants significantly reduces also.
The present invention has following characteristics:
1. the present invention uses by a minipump, a negative pressure bottle, the negative pressure source of an electric contact vacuum meter composition has realized making reactant to pass through a plurality of micro-fluidic reactors arranged side by side simultaneously with the low discharge of μ L/min level, improved the speed of research chemical synthesis route and development new drug, and have that apparatus structure is simple, with low cost, easy to operate, advantages such as reaction time and Controllable Temperature.
2. the present invention uses one negative pressure source to make simultaneously on the micro-fluidic reactor that reactant enters reaction channel simultaneously in a plurality of reactant liquid storage tanks under atmospheric driving, therefore the present invention not only can be used for two synthetic reactions between the reactant, also can be used for the synthetic reaction that a plurality of reactants are participated in.
3. the present invention uses the interface be installed on micro-fluidic reactor exit particular design, guaranteed in micro-fluidic reactor and the product liquid storage bottle between the impermeability of connecting line.
4. the present invention uses micro-regulating valve to regulate vacuum tightness in a plurality of product liquid storage bottles arranged side by side respectively, use one negative pressure source to make on the micro-fluidic reactor in a plurality of reactant liquid storage tanks the reactant can be simultaneously with identical flow velocity, again can be with different flow velocitys respectively by a plurality of micro-fluidic reactors arranged side by side.
5. the negatively pressurized sampling micro fluidics chemical synthesis reaction system selected for use of the present invention has versatility, both be applicable to the condition of the various synthetic reactions of research, as the reaction time, temperature, the flow velocitys of reactant by micro-fluidic reactor etc. are to the influence of productive rate, are applicable to the research of carrying out combinatorial chemistry and the comparison of homolog synthetic yield again.
6. the negatively pressurized sampling micro fluidics chemical synthesis reaction system selected for use of the present invention can be determined micro-fluidic reactor quantity arranged side by side according to the experiment needs, or selects the micro-fluidic reactor with different length reaction channel for use.
Description of drawings
Fig. 1. micro-fluidic chemical reaction system synoptic diagram
Among the figure: 1-micro-fluidic reactor, 2-interface, 3-minipump, 4-negative pressure bottle, 5-electric contact vacuum meter, 6-micro-regulating valve, 7-product liquid storage bottle, 8-electric hot plate, 9-connecting tube
Fig. 2. the interface wiring layout
Among the figure: the 9-polyfluortetraethylene pipe, there are sieve silk of passage, 11-polytetrafluoroethylene gasket in the 10-center to a Side, the 12-polytetrafluoroethylene gasket, the joint of rib-loop in the 13-band, 14-polytetrafluoroethylene gasket, connection sieve silk of 15-band center pit, 16 (a, b)-the reactant liquid storage tank
Concrete embodiment
Embodiment 1 studies the influence of reaction time to synthetic yield in 5 micro-fluidic reactors arranged side by side
Referring to Fig. 1, micro-fluidic chemical reaction system provided by the invention is made up of 1, five block of electric hot plate of five micro-fluidic reactors arranged side by side 8, five micro-regulating valves 6, five product liquid storage bottles 7 and five interfaces 2 and a public negative pressure source.Reactant solution liquid storage tank a on the micro-fluidic reactor 1 and the reactant among the b mix at intersection point c place, microchannel, chemical reaction takes place in reaction channel cd, and by at the interface 2 that is installed on micro-fluidic reactor exit (d), connecting tube 9 joins with product liquid storage bottle 7.Described public negative pressure source is by a minipump 3, a negative pressure bottle 4, an electric contact vacuum meter 5 is formed, negative pressure bottle 4 joins with vacuum pump 3, electric contact vacuum meter 5, product liquid storage bottle 7 respectively by connecting tube, on the connecting tube that negative pressure bottle 4 and product liquid storage bottle 7 join micro-regulating valve 6 is installed.
Referring to Fig. 2, be installed on the interface 2 of micro-fluidic reactor 1 exit d among the present invention, there are sieve silk 10, polytetrafluoroethylene gasket 11,12,14, the joint 13 of the interior rib-loop of band, connection sieve silk 15 of being with center pit and the teflon connecting tube 9 of passage to form by the center to a side.With the exit of glass micro-fluidic reactor with Glass drill head boring after, there is sieve silk of passage at the use center to a side, joint by rib-loop in two polytetrafluoroethylene gaskets and the band, the joint of rib-loop in the band is fixedly mounted in the exit of micro-fluidic reactor, again by a connection sieve silk and a polytetrafluoroethylene gasket of being with center pit, the polyfluortetraethylene pipe that connects the product liquid storage bottle hermetic is connected to the other end of the joint of rib-loop in the band, thereby make the reactant that places reactant liquid storage tank on the micro-fluidic reactor (a and b) under atmospheric promotion, through reaction channel cd, interface 2 and polyfluortetraethylene pipe 9 flow into product liquid storage bottle 7, and are stored in the product liquid storage bottle 7.
Glass micro-fluidic reactor photoetching, wet etching and high temperature bonding techniques, the microchannel configuration is shown in 1 among the Fig.1, and channel width is that 300 μ m, the degree of depth are 100 μ m, and length is respectively 12,24,36,48,60cm., in the ultrapure water environment cover plate and substrate are directly fitted after the punching of corresponding position with Glass drill head, the method with the high temperature bonding is bonded together cover plate and substrate, makes micro-fluidic reactor.Injection port a, b place in the microchannel are about 6mm with the bonding internal diameter of epoxy resin, and the polyfluortetraethylene pipe that highly is 20mm is as the reactant liquid storage tank, and reactant liquid storage tank a, the volume of b are about 560 μ L.Exit, microchannel d with the Glass drill head of diameter 5mm with the cover plate and substrate boring that are bonded together after, with 5 microchannel length 12,24,36,48, the micro-fluidic reactor of 60cm is for to be assembled into micro-fluidic chemical reaction system as Fig. 1 and Fig. 2 respectively.
With P-methoxybenzal-dehyde and oxammonium hydrochloride is that the synthetic P-methoxybenzal-dehyde oxime of raw material is an example, and the research reaction time, their chemical equation was as follows to the influence of synthetic yield:
The ethanolic solution 0.1mL that in the reactant liquid storage tank a of 5 glass micro-fluidic reactors, all adds the 2.0mol/L P-methoxybenzal-dehyde, the mixed aqueous solution 0.1mL that in reactant liquid storage tank b, all adds 2.4mol/L oxammonium hydrochloride and 2.4mol/L sodium bicarbonate, the ether of adding 20 μ L in product liquid storage bottle 7.Polyfluortetraethylene pipe connecting interface 2 and product liquid storage bottle 7, product liquid storage bottle 7 and micro-regulating valve 6 and micro-regulating valve 6 and negative pressure bottle 4 with external diameter 2mm internal diameter 1mm.The maximum vacuum of setting electric contact vacuum meter is-410mbar that the minimum vacuum degree is-390mbar.Close micro-regulating valve, extract air in the negative pressure bottle that volume is 1L with minipump.Vacuum tightness stops automatically for-410mbar final vacuum pump in negative pressure bottle.Slowly open micro-regulating valve again, make reactant flow through reacting pipe (flow velocity is 3.6 μ L/min) between micro-fluidic reactor cd under the room temperature with the flow velocity of 2mm/s.Reactant is 12,24,36,48 in reacting pipe length, and the reaction time in the micro-fluidic reactor of 60cm is respectively 1,2,3,4 and 5 minutes.In the product liquid storage bottle, can obtain reacted solution 18 μ L after 5 minutes.With ethereal extract in the GC-MS analytical test product liquid storage bottle, the productive rate of P-methoxybenzal-dehyde oxime is respectively 60%, 73%, 77%, 81% and 84% when obtaining the reaction time and being 1,2,3,4 and 5 minutes.Embodiment 2 carries out the chemosynthesis of 2 * 2 reactant various combinations in micro-fluidic reactor
Make 4 identical glass micro-fluidic reactors, the microchannel width is 300 μ m, the degree of depth is 100 μ m, and length is 24cm respectively.With 4 identical glass micro-fluidic reactors for to form micro-fluidic chemical reaction system as Fig. 1 and Fig. 2.
With 2 kinds of different organic amines [1-phenylethylenediamine (A) and 4-amino-1-Phenylpiperidine (B)] and 2 kinds of different acyl chlorides [3,5-dinitrobenzoyl chloride (C) and 3-nitrobenzoyl chloride (D)] be example, obtain product A C, BC, the productive rate of AD and BD when studying 2 * 2 combinations of their reactants.
2 kinds of organic amines are formulated in the solution of 0.1mol/L NaOH, obtain concentration and be 1 * 10
-2The 1-phenylethylenediamine (A) of mol/L and 4-amino-1-Phenylpiperidine (B) solution is formulated in 2 kinds of acyl chlorides in the ethyl acetate, obtains concentration and is 1 * 10
-23 of mol/L, the solution of 5-dinitrobenzoyl chloride (C) and 3-nitrobenzoyl chloride (D).Make up the aqueous solution that in reactant liquid storage tank a, adds two kinds of organic amines respectively at 4 identical glass micro-fluidic reactors by 2 * 2, in reactant liquid storage tank b, add the ethyl acetate solution of two kinds of acyl chlorides.They are reacted with following chemical equation respectively in the microchannel of 4 identical glass micro-fluidic reactors:
The maximum vacuum of setting electric contact vacuum meter is-410mbar that the minimum vacuum degree is-390mbar.Close micro-regulating valve, extract air in the negative pressure bottle that volume is 1L with minipump.Vacuum tightness is stopped automatically for-410mbar final vacuum pump.Slowly open micro-regulating valve again, make reactant flow through reacting pipe (flow velocity is 36 μ L/min) between micro-fluidic reactor cd under the room temperature with the flow velocity of 20mm/s.Obtain reacted solution 36 μ L at the product liquid storage bottle after 1 minute.Organic phase (ethyl acetate solution) in the chromatograph test product liquid storage bottle by comparing with the retention time of standard substance, determines that product is shown in above-mentioned reaction equation.AC, AD, the productive rate of BC and BD is respectively 91%, 84%, and 99% and 93%.
Claims (7)
1, a kind of negatively pressurized sampling micro fluidics chemical synthesis reaction system, by one or more micro-fluidic reactors arranged side by side, a public negative pressure source, and with the same number of electric hot plate of micro-fluidic reactor, micro-regulating valve, product liquid storage bottle and interface are formed: it is characterized in that, use a public negative pressure source to make on a plurality of micro-fluidic reactors reactant in the reactant liquid storage tank under atmospheric driving, enter separately micro-fluidic reactor simultaneously, make reactant locate to mix at microchannel intersection point (c), chemical reaction takes place in reaction channel (cd), and, make reacted product in polyfluortetraethylene pipe inflow product liquid storage bottle separately by at the interface that is installed on micro-fluidic reactor exit (d); Described public negative pressure source is by a minipump, a negative pressure bottle, and an electric contact vacuum meter is formed, and with vacuum tightness in electric contact vacuum meter indication and the control Dewar bottle, makes that vacuum tightness remains in the setting range in the Dewar bottle; In Dewar bottle vacuum tightness be lower than set vacuum tightness following in limited time, the power connection of electric contact vacuum meter control minipump, by using the air of minipump through polyfluortetraethylene pipe extracting vacuum bottle, make vacuum up in the Dewar bottle, vacuum tightness reaches and sets going up in limited time of vacuum tightness in Dewar bottle, minipump stops automatically, and the interior vacuum tightness of Dewar bottle is remained in the setting range; Micro-regulating valve all is equipped with in being connected that negative pressure bottle and each product liquid storage bottle join on the teflon pipeline, the opening degree negative pressure of regulating each product liquid storage bottle respectively by the control micro-regulating valve, reach and control reactant respectively and flow through each micro-fluidic reactor flow velocity, the required temperature of chemosynthesis reaction is controlled with electric hot plate.
2, negatively pressurized sampling micro fluidics chemical synthesis reaction system according to claim 1 is characterized in that being connected with polyfluortetraethylene pipe by interface the outlet (d) and the product liquid storage bottle of micro-fluidic reactor; With the exit of micro-fluidic reactor with Glass drill head boring after, there is the screw of passage at the use center to a side, by two polytetrafluoroethylene gaskets and a tapped joint, tapped joint is fixedly mounted in the exit of micro-fluidic reactor, again by a connecting screw and a polytetrafluoroethylene gasket of being with center pit, the polyfluortetraethylene pipe that connects the product liquid storage bottle is connected to the other end of tapped joint, thereby has guaranteed the impermeability that micro-fluidic reactor is connected with polyfluortetraethylene pipe.
3, negatively pressurized sampling micro fluidics chemical synthesis reaction system according to claim 1, it is characterized in that, the quantity of electric hot plate, micro-regulating valve, product liquid storage bottle and interface is identical with micro-fluidic reactor quantity arranged side by side, controls flow velocity and the temperature of reaction of reactant in reaction channel in each micro-fluidic reactor respectively.
4, negatively pressurized sampling micro fluidics chemical synthesis reaction system according to claim 1, the quantity that it is characterized in that reactant liquid storage tank on each micro-fluidic reactor is determined according to chemical equation, use a public negative pressure source to make simultaneously on the micro-fluidic reactor that reactant enters reaction channel simultaneously in a plurality of reactant liquid storage tanks under atmospheric driving, carry out chemical reaction.
5, negatively pressurized sampling micro fluidics chemical synthesis reaction system according to claim 1, it is characterized in that using micro-regulating valve to regulate vacuum tightness in a plurality of product liquid storage bottles arranged side by side respectively, use a public negative pressure source to make on a plurality of micro-fluidic reactors arranged side by side in a plurality of reactant liquid storage tanks the reactant can be simultaneously with identical flow velocity, again can be with different flow velocitys respectively by a plurality of micro-fluidic reactors arranged side by side.
6, the using method of the described negatively pressurized sampling micro fluidics chemical synthesis reaction system of claim 1, step is as follows: at the reactant liquid storage tank (a of micro-fluidic reactor, b) add different reactant solutions in respectively, by setting the minimum and maximum vacuum tightness of electric contact vacuum meter, connect the minipump power supply, make and form negative pressure in the Dewar bottle, when reaching to set on the vacuum tightness, vacuum tightness in the bottle prescribes a time limit, electric contact vacuum meter is closed the minipump power supply, when being lower than to set under the vacuum tightness, vacuum tightness in the bottle prescribes a time limit, electric contact vacuum meter starts minipump, makes bottle interior vacustat in the scope of setting; Opening degree by the control micro-regulating valve, different reactant flow in the reactant liquid storage tank is gone in the microchannel of micro-fluidic reactor, locate mixing at microchannel intersection point (c) and begin reaction, and, reacted product is flowed in the product liquid storage bottle by being installed on the interface that micro-fluidic reactor outlet (d) is located.
7, the using method of negatively pressurized sampling micro fluidics chemical synthesis reaction system according to claim 6, it is characterized in that, the required temperature of chemosynthesis reaction is controlled with electric hot plate, use the micro-fluidic reactor control reaction time of different length microchannel, or the opening degree negative pressure of regulating each product liquid storage bottle of control micro-regulating valve, the flow velocity of micro-fluidic reactor is crossed in the conditioned reaction logistics.
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| KR101602414B1 (en) * | 2009-03-16 | 2016-03-11 | 삼성전자주식회사 | Apparatus for fluidic control |
| US20120211084A1 (en) * | 2009-09-02 | 2012-08-23 | President And Fellows Of Harvard College | Multiple emulsions created using jetting and other techniques |
| CN103537239B (en) * | 2012-07-08 | 2016-01-06 | 复旦大学附属肿瘤医院 | Small size [ 18f] fluorine isotope labeling reactor and application thereof |
| CN102989533B (en) * | 2012-12-20 | 2015-05-13 | 中国科学院上海微系统与信息技术研究所 | Micro-fluidic chip for high-flux automatically rationing and mixing and use method and application of chip |
| CN103277284B (en) * | 2013-06-21 | 2016-06-22 | 苏州盟通利机电设备有限公司 | Fully automatic vacuum air extractor and control method thereof |
| CN106290269B (en) * | 2016-07-22 | 2019-04-26 | 东北大学 | A kind of compound microbial rapid detection method and microchip systems |
| CN106370878B (en) * | 2016-10-09 | 2018-09-18 | 苏州工业园区龙兆生物科技研究院有限公司 | A kind of negative pressure automatic sampling apparatus for micro-fluidic chip |
| CN107228847A (en) * | 2017-05-18 | 2017-10-03 | 大连海事大学 | The micro-fluidic radiation injury monitoring device and method of collection capture culture detection integration |
| CN108479874A (en) * | 2018-05-25 | 2018-09-04 | 中国科学技术大学 | A kind of electric pipettor |
| CN110116028B (en) * | 2019-05-28 | 2021-06-25 | 长春长光辰英生物科学仪器有限公司 | Microfluidic experimental device and method |
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| Micro-flow reaction systems for combinatorial syntheses.. Kikutani, Yoshikuni, Kitamori, Takehiko.Macromolecular Rapid Communications,Vol.25 No.1. 2004 |
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