CN115819381A - Method for separating and purifying furfuryl amine in biological catalysis system - Google Patents
Method for separating and purifying furfuryl amine in biological catalysis system Download PDFInfo
- Publication number
- CN115819381A CN115819381A CN202211648831.0A CN202211648831A CN115819381A CN 115819381 A CN115819381 A CN 115819381A CN 202211648831 A CN202211648831 A CN 202211648831A CN 115819381 A CN115819381 A CN 115819381A
- Authority
- CN
- China
- Prior art keywords
- separation
- desorption
- adsorption
- liquid
- flow rate
- 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.)
- Pending
Links
- DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 title claims abstract description 69
- 238000000034 method Methods 0.000 title claims abstract description 33
- 238000006555 catalytic reaction Methods 0.000 title claims abstract description 26
- 238000003795 desorption Methods 0.000 claims abstract description 80
- 239000007788 liquid Substances 0.000 claims abstract description 53
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims abstract description 46
- 238000000926 separation method Methods 0.000 claims abstract description 31
- 229940107700 pyruvic acid Drugs 0.000 claims abstract description 23
- 238000000746 purification Methods 0.000 claims abstract description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000005891 transamination reaction Methods 0.000 claims abstract description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000012295 chemical reaction liquid Substances 0.000 claims abstract description 4
- 229910021529 ammonia Inorganic materials 0.000 claims abstract 2
- 238000001179 sorption measurement Methods 0.000 claims description 62
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 238000005374 membrane filtration Methods 0.000 claims description 6
- 239000003463 adsorbent Substances 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- 239000012043 crude product Substances 0.000 claims description 2
- 238000005189 flocculation Methods 0.000 claims description 2
- 230000016615 flocculation Effects 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- 102000004169 proteins and genes Human genes 0.000 abstract description 12
- 108090000623 proteins and genes Proteins 0.000 abstract description 12
- 241001052560 Thallis Species 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 6
- 239000006227 byproduct Substances 0.000 abstract description 5
- 229910017053 inorganic salt Inorganic materials 0.000 abstract description 4
- 239000002028 Biomass Substances 0.000 abstract description 3
- 230000003993 interaction Effects 0.000 abstract description 3
- 229920003053 polystyrene-divinylbenzene Polymers 0.000 abstract description 2
- 239000011347 resin Substances 0.000 description 47
- 229920005989 resin Polymers 0.000 description 47
- 102000003929 Transaminases Human genes 0.000 description 23
- 108090000340 Transaminases Proteins 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 18
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 16
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 10
- 241000588724 Escherichia coli Species 0.000 description 10
- 235000011114 ammonium hydroxide Nutrition 0.000 description 10
- 235000018102 proteins Nutrition 0.000 description 10
- 239000000919 ceramic Substances 0.000 description 9
- 239000012528 membrane Substances 0.000 description 8
- 230000002210 biocatalytic effect Effects 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 238000005265 energy consumption Methods 0.000 description 3
- 238000002203 pretreatment Methods 0.000 description 3
- 230000003068 static effect Effects 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 238000010170 biological method Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001713 cholinergic effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000703 high-speed centrifugation Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
Abstract
A separation and purification method of furfuryl amine in a biological catalysis system belongs to the technical field of biomass separation. Aiming at the blank of the separation and purification of furfuryl amine in the existing biological catalysis system, the invention mainly solves the difficult problem of separating furfuryl amine from a transamination reaction liquid with high thallus, protein, inorganic salt and coexisting byproducts. Provides a separation and purification method of furfuryl amine in a biological catalysis system, in particular to a method for obtaining clear liquid of transamination reaction by solid-liquid separation; adsorbing and separating furfuryl amine; and (4) adsorbing and separating pyruvic acid. The method removes thalli and protein by simple solid-liquid separation, adsorbs furfurylamine of a biological catalysis system by the physical size matching and pi-conjugated interaction specificity of a polystyrene divinylbenzene material, obtains high-purity furfurylamine by desorption, and has the yield of 95 percent; and the acetone which is a byproduct of the ammonia conversion reaction liquid is further adsorbed and separated, and the acetone with high added value is recovered.
Description
Technical Field
The invention belongs to the technical field of biomass separation, and particularly relates to a method for separating and purifying furfuryl amine in a biological catalysis system.
Background
Furfuryl amine (2-Furfurylamine, FLA) is a colorless oily liquid and has a variety of applications in modern chemistry and industry, including the synthesis of polymers, pesticides, bioactive molecules, and as intermediates in the synthesis of drugs such as bactericides, cholinergic agents, hypotensive agents, and diuretics. At present, the main synthetic method of furfuryl amine is to use furfural as a raw material, and carry out hydrogenation reaction with liquid ammonia under the catalysis of raney nickel under the conditions of high temperature and high pressure, the reaction conditions are harsh, and the separation and purification method is a rectification method, which needs high-temperature purification and has lower yield of only 40%. Therefore, development of green and mild preparation of furfuryl amine is a problem to be solved urgently.
Transaminase (TA) can catalyze amino groups to be transferred from an amino donor to an amino acceptor, dunbabin and the like in 2017 utilize the transaminase to prepare furfuryl amine (Dunbabin, green Chemistry,2017,19,397) from furfural at a conversion rate of over 90 percent, and the furfuryl amine biocatalytic preparation without harsh conditions such as high temperature, high pressure and the like is realized for the first time; in 2019, zhang and the like use corncob meal hydrolysis and transaminase catalysis to perform two-step reaction, so that mild preparation of furfuryl amine (Zhang, ACS sustamable chem.Eng.,2019,7,17636) by cheap biomass is realized. However, the current reports about preparing furfuryl amine by catalyzing furfural with transaminase only stay at the laboratory research level, and the high-efficiency separation technology for synthesizing furfuryl amine by a biological method is lacked. The biocatalytic furfuryl amine system contains a large amount of thalli, protein, inorganic salt, organic acid, excessive alanine, pyruvic acid and other byproducts, and the problems of large distillation volume, high energy consumption, low yield and the like exist through conventional reduced pressure distillation and rectification modes. Therefore, a high-efficiency separation method for furfuryl amine in a process of preparing furfuryl amine by catalyzing furfural with transaminase is needed.
Disclosure of Invention
The invention provides a method for separating and purifying furfuryl amine in a biological catalysis system, aiming at the problems that the prior technology for separating and purifying furfuryl amine in the biological catalysis system has high energy consumption, high cost and low yield, and is difficult to solve the problem of separating furfuryl amine with high content of thalli, protein, inorganic salt and coexisting pyruvic acid.
The method for separating and purifying furfuryl amine in a biological catalysis system specifically comprises the following steps:
s1, carrying out solid-liquid separation on the transamination reaction liquid to obtain a transamination reaction clear liquid;
the transamination reaction clear liquid obtained from S2 and S1 enters an adsorption column A, the effluent liquid is a crude pyruvic acid solution, and the adsorption column A is desorbed by the desorption liquid A to obtain a furfuryl amine desorption liquid;
and (3) feeding the pyruvic acid crude product solution obtained in the S3 and the S2 into an adsorption column B at a certain flow rate, wherein the adsorption mode is series feeding, and desorbing the adsorption column B by using the desorption solution B to obtain pyruvic acid desorption solution.
In an embodiment of the invention, the solid-liquid separation method in S1 includes any one or a combination of two or more of membrane filtration, flocculation precipitation, plate-and-frame filtration and centrifugal separation.
Preferably, the solid-liquid separation method in S1 is ceramic membrane filtration, and the pore size of the ceramic membrane is preferably 0.05 μm.
In one embodiment of the invention, the adsorbing material used in the S2 adsorption column A is any one of HPD500, NDA-99, NDA-150, NKA-II, XDA-4, XDA-7, CHA-111, H103, D001, 001 x 7, LXP-08, LX-1850.
Preferably, the adsorbing material used by the adsorbing column A in S2 is NKA-II or LXP-08.
In one embodiment of the present invention, the ratio of height to diameter of the adsorption column a in S2 is 3:1 to 20:1, the adsorption mode is multistage series adsorption, the adsorption stage number is 2-4 stages, the adsorption flow rate is 0.5-3 BV/h, the mode is downstream column passing, and the temperature is 25-80 ℃.
In one embodiment of the invention, the desorption solution A in S2 is one or a mixture of two of ammonia water, sodium hydroxide, methanol, ethanol and acetone; the dosage of the desorption solution is 1 BV-2 BV.
In one embodiment of the invention, the desorption flow rate of S2 is 0.2 BV/h-3 BV/h, the temperature is 25-80 ℃, the mode is a forward flow column passing mode, the collection of 0.3-0.8BV is carried out, and the 0.8-1 BV is used indiscriminately.
In one embodiment of the present invention, the adsorbent used in the adsorbent column B of S3 is any one or a combination of two or more of 201 × 7, D201, D301, LXP-01, and LX-27.
In one embodiment of the present invention, the ratio of height to diameter of the adsorption column B in S3 is 3:1 to 10:1, the flow rate is 0.2 BV/h-3 BV/h, and the temperature is 25-50 ℃.
In one embodiment of the present invention, the desorption solution B in S3 is any one or a mixture of two or more of hydrochloric acid, methanol, ethanol, and acetone; the dosage of the desorption liquid B is 1 BV-2 BV.
In one embodiment of the invention, the desorption flow rate of S3 is 0.2 BV/h-3 BV/h, the temperature is 25-80 ℃, the mode is a mode of cocurrent column passing, the 0.3-0.8 BV is collected, and the 0.8-1 BV is used indiscriminately.
The invention has the beneficial effects that:
aiming at the problem that the existing biological catalysis system contains high-content thalli, protein, inorganic salt and coexisting pyruvic acid by-products and is difficult to separate and purify the furfuryl amine, the invention realizes the high-efficiency and low-energy consumption separation and purification of the furfuryl amine by a furfuryl amine specific adsorption material, and has the following specific advantages:
(1) The bacteria and protein are removed by simple solid-liquid separation, a polystyrene divinylbenzene material with rich specific surface area and strong conjugate interaction is selected, the furfurylamine in a biological water system is specifically adsorbed by physical size matching and pi-pi conjugate interaction, and the high-purity furfurylamine is obtained by ammonia water desorption, wherein the yield reaches 95%. Effectively solves the problem that the furfuryl amine in the biological catalysis system is difficult to separate, and has important significance for promoting the green and mild preparation of the furfuryl amine in the biological catalysis system.
(2) The specific adsorption separation is carried out on the byproduct pyruvic acid, and the product utilization rate of the biocatalysis system is improved.
Drawings
FIG. 1 is a graph showing the comparison of the adsorption capacities of NKA-II resin to pyruvic acid, furfuryl amine and furfural in example 1;
FIG. 2 is a graph of the capacity comparison of different resins for static adsorption in a 9.72g/L biocatalytic furfuryl amine system;
FIG. 3 is a furfurylamine dynamic adsorption curve obtained by dynamic adsorption of 9.72g/L biocatalytic furfurylamine system by NKA-II resin.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail below with reference to specific embodiments and the accompanying drawings. The experimental procedures used in the examples below are conventional, unless otherwise specified, and the materials, reagents, methods and apparatus used are conventional in the art, and those skilled in the art are commercially available.
The treated objects in all the following examples are the transaminase Escherichia coli liquid for preparing furfuryl amine by micro-catalysis of furfural, the solid content is 13%, the pH value is 6.0-8.0, and the concentration of furfuryl amine is 9.72g/L.
Example 1:
the embodiment provides a method for separating and purifying furfuryl amine in a biological catalysis system, which specifically comprises the following steps:
step 1: passing the transaminase reaction Escherichia coli liquid (1L) through a ceramic membrane with the aperture of 0.05 μm at the flow rate of 50mL/min to obtain transaminase reaction clear liquid;
and 2, step: NKA-II resin is selected to fill a resin column, and the height-diameter ratio is 3:1, performing two-stage series feeding at the flow rate of 3BV/h and the adsorption mode of 1BV/h at room temperature, performing two-stage series desorption on an ammonia water solution with the mass fraction of 10% as a desorption solution after adsorption, and obtaining a furfurylamine desorption solution with the yield of 95%;
and 3, step 3: d201 resin is selected to fill a resin column, and the height-diameter ratio is 3:1, feeding at the room temperature at the flow rate of 3BV/h in a two-stage series connection mode, taking hydrochloric acid with the mass fraction of 5% as desorption liquid at the flow rate of 1BV/h in a two-stage series connection mode after adsorption is finished, and obtaining pyruvic acid desorption solution.
Example 2:
the embodiment provides a method for separating and purifying furfuryl amine in a biological catalysis system, which specifically comprises the following steps:
step 1: passing the transaminase reaction Escherichia coli liquid (1L) through a ceramic membrane with the aperture of 0.05 μm at the flow rate of 50mL/min to obtain transaminase reaction clear liquid;
and 2, step: NDA-150 resin is selected to fill a resin column, and the height-diameter ratio is 3:1, performing two-stage series feeding at the flow rate of 3BV/h and the adsorption mode of 1BV/h at room temperature, performing two-stage series desorption on an ammonia water solution with the mass fraction of 10% as a desorption solution after adsorption, and obtaining a furfurylamine desorption solution with the yield of 93%;
and step 3: d201 resin is selected to fill a resin column, and the height-diameter ratio is 3:1, feeding in a two-stage series mode at the flow rate of 3BV/h at room temperature, taking hydrochloric acid with the mass fraction of 5% as desorption liquid after adsorption, and obtaining pyruvic acid desorption solution at the flow rate of 1BV/h and in the two-stage series desorption mode.
Example 3:
the embodiment provides a method for separating and purifying furfuryl amine in a biological catalysis system, which specifically comprises the following steps:
step 1: passing the transaminase reaction Escherichia coli liquid (1L) through a ceramic membrane with the aperture of 0.05 μm at the flow rate of 50mL/min to obtain transaminase reaction clear liquid;
step 2: NDA-150 resin is selected to fill a resin column, and the height-diameter ratio is 3:1, performing two-stage series feeding at the flow rate of 3BV/h and the adsorption mode at room temperature, performing two-stage series desorption on an ammonia water solution with the mass fraction of 10% as a desorption solution at the flow rate of 1BV/h after adsorption, and obtaining a furfurylamine desorption solution with the yield of 97%;
and step 3: filling a resin column with 201 × 7 resin, wherein the height-diameter ratio is 3:1, feeding in a two-stage series mode at the flow rate of 3BV/h at room temperature, taking hydrochloric acid with the mass fraction of 5% as desorption liquid after adsorption, and obtaining pyruvic acid desorption solution at the flow rate of 1BV/h and in the two-stage series desorption mode.
Example 4:
the embodiment provides a method for separating and purifying furfuryl amine in a biological catalysis system, which specifically comprises the following steps:
step 1: passing the transaminase reaction Escherichia coli liquid (1L) through a ceramic membrane with the aperture of 0.05 μm at the flow rate of 50mL/min to obtain transaminase reaction clear liquid;
step 2: NDA-150 resin is selected to fill a resin column, and the height-diameter ratio is 3:1, feeding at room temperature at a flow rate of 3BV/h in a two-stage series connection mode, taking ethanol as desorption liquid at a flow rate of 1BV/h after adsorption is finished, and obtaining a furfurylamine desorption solution with a furfurylamine yield of 92 percent, wherein the desorption mode is a two-stage series connection desorption;
and step 3: d201 resin is selected to fill a resin column, and the height-diameter ratio is 3:1, feeding at the room temperature at the flow rate of 3BV/h in a two-stage series connection mode, taking hydrochloric acid with the mass fraction of 5% as desorption liquid at the flow rate of 1BV/h in a two-stage series connection mode after adsorption is finished, and obtaining pyruvic acid desorption solution.
Example 5:
the embodiment provides a method for separating and purifying furfuryl amine in a biological catalysis system, which specifically comprises the following steps:
step 1: passing the transaminase reaction Escherichia coli liquid (1L) through a ceramic membrane with the aperture of 0.05 μm at the flow rate of 50mL/min to obtain transaminase reaction clear liquid;
step 2: LXP-08 resin is selected to fill a resin column, and the height-diameter ratio is 3:1, performing two-stage series feeding at the flow rate of 3BV/h and the adsorption mode at room temperature, performing two-stage series desorption on an ammonia water solution with the mass fraction of 10% as a desorption solution at the flow rate of 1BV/h after adsorption, and obtaining a furfurylamine desorption solution with the yield of 90%;
and step 3: d201 resin is selected to fill a resin column, and the height-diameter ratio is 3:1, feeding in a two-stage series mode at the flow rate of 3BV/h at room temperature, taking hydrochloric acid with the mass fraction of 5% as desorption liquid after adsorption, and obtaining pyruvic acid desorption solution at the flow rate of 1BV/h and in the two-stage series desorption mode.
Example 6:
the embodiment provides a method for separating and purifying furfuryl amine in a biological catalysis system, which specifically comprises the following steps:
step 1: centrifuging the transamination reaction escherichia coli liquid (1L) at a high speed of 2000rpm to remove thalli and protein to obtain a transamination reaction clear liquid;
and 2, step: NDA-150 resin is selected to fill a resin column, and the height-diameter ratio is 3:1, performing two-stage series feeding at the flow rate of 3BV/h and the adsorption mode at room temperature, performing two-stage series desorption by using an ammonia water solution with the mass fraction of 10% as a desorption solution at the flow rate of 1BV/h after adsorption, and obtaining a furfurylamine desorption solution with the yield of 91%;
and step 3: d201 resin is selected to fill a resin column, and the height-diameter ratio is 3:1, feeding in a two-stage series mode at the flow rate of 3BV/h at room temperature, taking hydrochloric acid with the mass fraction of 5% as desorption liquid after adsorption, and obtaining pyruvic acid desorption solution at the flow rate of 1BV/h and in the two-stage series desorption mode.
Example 7:
the embodiment provides a method for separating and purifying furfuryl amine in a biological catalysis system, which specifically comprises the following steps:
step 1: removing thalli and protein from the transaminase reaction escherichia coli bacterial liquid (1L) in a plate-and-frame filtration mode to obtain transaminase reaction clear liquid;
and 2, step: NDA-150 resin is selected to fill a resin column, and the height-diameter ratio is 3:1, feeding at room temperature at a flow rate of 3BV/h in a two-stage series connection mode, taking an ammonia water solution with the mass fraction of 10% as desorption liquid at a flow rate of 1BV/h after adsorption is finished, and obtaining a furfurylamine desorption solution with the yield of 94 percent by taking a desorption mode as two-stage series connection desorption;
and 3, step 3: d201 resin is selected to fill a resin column, and the height-diameter ratio is 3:1, feeding at the room temperature at the flow rate of 3BV/h in a two-stage series connection mode, taking hydrochloric acid with the mass fraction of 5% as desorption liquid at the flow rate of 1BV/h in a two-stage series connection mode after adsorption is finished, and obtaining pyruvic acid desorption solution.
Example 8:
the embodiment provides a method for separating and purifying furfuryl amine in a biological catalysis system, which specifically comprises the following steps:
step 1: passing the transaminase reaction Escherichia coli liquid (50L) through a ceramic membrane with the aperture of 0.05 μm at the flow rate of 200mL/min to obtain transaminase reaction clear liquid;
step 2: NKA-II resin is selected to fill a resin column, and the height-diameter ratio is 3:1, performing two-stage series feeding at the flow rate of 3BV/h and the adsorption mode of 1BV/h at room temperature, performing two-stage series desorption on an ammonia water solution with the mass fraction of 10% as a desorption solution after adsorption, and obtaining a furfurylamine desorption solution with the yield of 93%;
and step 3: d201 resin is selected to fill a resin column, and the height-diameter ratio is 3:1, feeding in a two-stage series mode at the flow rate of 3BV/h at room temperature, taking hydrochloric acid with the mass fraction of 5% as desorption liquid after adsorption, and obtaining pyruvic acid desorption solution at the flow rate of 1BV/h and in the two-stage series desorption mode.
Example 9:
the embodiment provides a method for separating and purifying furfuryl amine in a biological catalysis system, which specifically comprises the following steps:
step 1: passing the transaminase reaction Escherichia coli liquid (50L) through a ceramic membrane with aperture of 0.05 μm at flow rate of 200mL/min to obtain transaminase reaction clear liquid;
step 2: NDA-150 resin is selected to fill a resin column, and the height-diameter ratio is 3:1, feeding at room temperature at a flow rate of 3BV/h in a two-stage series connection mode, taking an ammonia water solution with the mass fraction of 10% as desorption liquid at a flow rate of 1BV/h after adsorption is finished, and obtaining a furfurylamine desorption solution with a furfurylamine yield of 91 percent in a two-stage series connection desorption mode;
and step 3: and (2) filling an LX-27 resin into a resin column, wherein the height-diameter ratio is 3:1, feeding in a two-stage series mode at the flow rate of 3BV/h at room temperature, taking hydrochloric acid with the mass fraction of 5% as desorption liquid after adsorption, and obtaining pyruvic acid desorption solution at the flow rate of 1BV/h and in the two-stage series desorption mode.
And (3) detecting the separation and purification effect:
the results of measurements of the cell and protein removal rates of the three fermentation broth pretreatment methods of examples 6 to 7 and example 9, i.e., high-speed centrifugation (example 6), plate-and-frame filtration (example 7) and membrane filtration (example 9), are shown in Table 1. As can be seen from Table 1, the three treatment methods all gave higher cell removal rates, but only the plate-and-frame filtration method and the membrane filtration method gave higher protein removal rates, and among them, the pretreatment method having the best cell and protein removal effects was the membrane filtration method.
TABLE 1 comparison of the removal rates of bacteria and proteins by different fermentation broth pretreatment methods
(II) the NKA-II resin in example 1 was measured for adsorption capacity of each of the three substances in a mixed system of furfurylamine, furfural and pyruvic acid at 1000mg/L, and the results are shown in FIG. 1. As shown in figure 1, the NKA-II resin has an equilibrium adsorption capacity of 130mg/g for furfuryl amine, but does not adsorb furfural and pyruvic acid, and the NKA-II resin can specifically adsorb furfuryl amine.
(III) the capacity of static adsorption of CHA-111, H103, NDA-150, NDA-99, HPD500 and NKA-II resins in a biocatalytic furfuryl amine system of 9.72g/L (see figure 2) is determined, the resin dosage is 0.06g, the volume of the adsorption solution is 20mL, and the static adsorption is carried out for 4 hours in a shaking table at the temperature of 25 ℃ and the rotation speed of 180 rpm. As shown in FIG. 2, the equilibrium adsorption amounts of furfuryl amine in the above resins are ranked from high to low as NKA-II, H103, NDA-99, CHA-111, and HPD500.
(IV) determination of dynamic adsorption of 9.72g/L biocatalytic furfuryl amine system using NKA-II resin from example 1, resin column BV 50mL, aspect ratio 20:1, the feeding amount is 3BV, the desorption solution is ethanol, the desorption is 3BV, and the specific desorption result is shown in figure 3. As can be seen from FIG. 3, NKA-II has good adsorption performance on furfuryl amine, the ethanol desorption and concentration effect can reach 4.6 times, and the desorption rate is 99%.
Although the present invention has been described with reference to the preferred embodiments, it should be understood that various changes and modifications can be made therein by those skilled in the art without departing from the spirit and scope of the invention as defined in the appended claims.
Claims (10)
1. A separation and purification method of furfuryl amine in a biological catalysis system is characterized by comprising the following steps:
s1, carrying out solid-liquid separation on the transamination reaction liquid to obtain a transamination reaction clear liquid;
the transamination reaction clear liquid obtained from S2 and S1 enters an adsorption column A, the effluent liquid is a crude pyruvic acid solution, and the adsorption column A is desorbed by the desorption liquid A to obtain a furfuryl amine desorption liquid;
and (3) feeding the pyruvic acid crude product solution obtained in the S3 and the S2 into an adsorption column B at a certain flow rate, wherein the adsorption mode is series feeding, and desorbing the adsorption column B by using the desorption solution B to obtain pyruvic acid desorption solution.
2. The separation and purification method according to claim 1, wherein the solid-liquid separation method in S1 comprises any one or a combination of two or more of membrane filtration, flocculation precipitation, plate-and-frame filtration and centrifugal separation.
3. The separation and purification process according to claim 1, wherein the adsorbent used in the adsorption column A of S2 is any one of HPD500, NDA-99, NDA-150, NKA-II, XDA-4, XDA-7, CHA-111, H103, D001, 001X 7, LXP-08, LX-1850.
4. The separation and purification method according to claim 1, wherein the height-diameter ratio of the adsorption column A in S2 is 3:1 to 20:1, the adsorption mode is multistage series adsorption, the adsorption stage number is 2-4 stages, the adsorption flow rate is 0.5-3 BV/h, the mode is downstream column passing, and the temperature is 25-80 ℃.
5. The separation and purification method according to claim 1, wherein the desorption solution a in S2 is any one or a mixture of two of ammonia, sodium hydroxide, methanol, ethanol and acetone; the dosage of the desorption solution is 1 BV-2 BV.
6. The separation and purification method according to claim 1, wherein the desorption flow rate of S2 is 0.2 BV/h-3 BV/h, the temperature is 25-80 ℃, the mode is a cocurrent flow through a column, the 0.3-0.8 BV is collected, and the 0.8-1 BV is used indiscriminately.
7. The separation and purification process according to claim 1, wherein the adsorbent used in the adsorbent column B of S3 is any one or a combination of two or more of 201 x 7, D201, D301, LXP-01, and LX-27.
8. The separation and purification method according to claim 1, wherein the height/diameter ratio of the adsorption column B of S3 is 3:1-10, the flow rate is 0.2 BV/h-3 BV/h, and the temperature is 25-50 ℃.
9. The separation and purification method according to claim 1, wherein the desorption solution B in S3 is any one or a mixture of two or more of hydrochloric acid, methanol, ethanol and acetone; the dosage of the desorption liquid B is 1 BV-2 BV.
10. The separation and purification method according to claim 1, wherein the desorption flow rate of S3 is 0.2BV/h to 3BV/h, the temperature is 25 ℃ to 80 ℃, the flow is concurrent flow through a column, the 0.3 BV to 0.8BV is collected, and the 0.8BV to 1BV is used indiscriminately.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211648831.0A CN115819381A (en) | 2022-12-21 | 2022-12-21 | Method for separating and purifying furfuryl amine in biological catalysis system |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211648831.0A CN115819381A (en) | 2022-12-21 | 2022-12-21 | Method for separating and purifying furfuryl amine in biological catalysis system |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN115819381A true CN115819381A (en) | 2023-03-21 |
Family
ID=85517361
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202211648831.0A Pending CN115819381A (en) | 2022-12-21 | 2022-12-21 | Method for separating and purifying furfuryl amine in biological catalysis system |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN115819381A (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101020629A (en) * | 2007-03-09 | 2007-08-22 | 浙江大学 | Process of separating acetylpropionic acid with active carbon |
| CN101514155A (en) * | 2009-03-31 | 2009-08-26 | 王东阳 | Method for separating and extracting pyruvic acid from fermentation broth by an ion exchange method |
| CN104926701A (en) * | 2015-06-30 | 2015-09-23 | 西安蓝晓科技新材料股份有限公司 | Purification process of methionine |
-
2022
- 2022-12-21 CN CN202211648831.0A patent/CN115819381A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101020629A (en) * | 2007-03-09 | 2007-08-22 | 浙江大学 | Process of separating acetylpropionic acid with active carbon |
| CN101514155A (en) * | 2009-03-31 | 2009-08-26 | 王东阳 | Method for separating and extracting pyruvic acid from fermentation broth by an ion exchange method |
| CN104926701A (en) * | 2015-06-30 | 2015-09-23 | 西安蓝晓科技新材料股份有限公司 | Purification process of methionine |
Non-Patent Citations (1)
| Title |
|---|
| 苏晓萌等: "功能化多壁碳纳米管的制备及对糠胺的高效吸附", 离子交换与吸附, vol. 38, no. 5, pages 426 - 436 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2673190C1 (en) | Method for obtaining l-methionine and organic acid | |
| CN104774881B (en) | A kind of method of living things catalysis production L- butyrines | |
| CN102040476B (en) | Method for separating and purifying 1,3-propylene glycol from fermentation liquor | |
| CN112979482B (en) | High-purity L-valine as well as preparation method and application thereof | |
| CN1944661A (en) | Process for preparing citicoline sodium | |
| CN105506014B (en) | The biological synthesis method of high optical voidness L- homoserine and its derivative | |
| CN101831475A (en) | Method for producing high-purity oligomate | |
| CN100413832C (en) | Method for separating 1,3-propanediol from fermentation liquor | |
| CA2783682C (en) | Method for obtaining ethanol during fermentation | |
| CN115819381A (en) | Method for separating and purifying furfuryl amine in biological catalysis system | |
| CN102241706A (en) | D-ribose purification and separation method | |
| CN101445466B (en) | Method for purifying 2, 2-dimethyl-cyclopropane carboxamide produced by biocatalytic method | |
| CN101066989A (en) | Process of separating and purifying glutathione from fermented liquid in a four-area simulated moving bed | |
| CN105969836B (en) | Method for splitting abacavir chiral intermediate vinelactone by enzymatic method | |
| CN101709037A (en) | Method for preparing high-purity D-amino acid | |
| CN104822652A (en) | Method for purifying 1,4-diaminobutane, 1,4-diaminobutane purified by said method, and polyamide prepared therefrom | |
| CN105238841A (en) | Recycling and conversion method of DCPC in cephalosporin C adsorption waste liquid | |
| CN106480009B (en) | Immobilized amino acid ester acyl transferase and application thereof in preparation of glutamine dipeptide | |
| CN102432495B (en) | Method for separating and concentrating L-theanine from glutaminase or glutamyl transpeptidase conversion liquid by membrane integration technology | |
| CN102226208B (en) | Preparation method of D-asparagine | |
| CN101081810B (en) | Purification method of propenoic acid produced by biology catalysis | |
| CN109321613B (en) | Method for producing D-mannose | |
| CN105906688A (en) | Technological system and technological method for extracting glutathione | |
| CN111217692A (en) | Preparation method of high-purity gallic acid | |
| CN101139382A (en) | Method for separating and purifying glutathione in fermentation liquor by five-region simulated moving bed chromatography |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |