CN116287049A - Preparation method of enzyme-catalyzed bio-based nylon auxiliary - Google Patents
Preparation method of enzyme-catalyzed bio-based nylon auxiliary Download PDFInfo
- Publication number
- CN116287049A CN116287049A CN202310280939.7A CN202310280939A CN116287049A CN 116287049 A CN116287049 A CN 116287049A CN 202310280939 A CN202310280939 A CN 202310280939A CN 116287049 A CN116287049 A CN 116287049A
- Authority
- CN
- China
- Prior art keywords
- reaction
- enzyme
- furandicarboxylate
- nylon
- preparation
- 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
- 229920006118 nylon 56 Polymers 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 29
- 238000000034 method Methods 0.000 claims abstract description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 13
- 239000003054 catalyst Substances 0.000 claims abstract description 12
- YAXWOADCWUUUNX-UHFFFAOYSA-N 1,2,2,3-tetramethylpiperidine Chemical compound CC1CCCN(C)C1(C)C YAXWOADCWUUUNX-UHFFFAOYSA-N 0.000 claims abstract description 11
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 claims abstract description 11
- DNXDYHALMANNEJ-UHFFFAOYSA-N furan-2,3-dicarboxylic acid Chemical compound OC(=O)C=1C=COC=1C(O)=O DNXDYHALMANNEJ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000002994 raw material Substances 0.000 claims abstract description 10
- 108090000790 Enzymes Proteins 0.000 claims abstract description 9
- 102000004190 Enzymes Human genes 0.000 claims abstract description 9
- 239000011259 mixed solution Substances 0.000 claims abstract description 9
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 6
- 239000003960 organic solvent Substances 0.000 claims abstract description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract 6
- 229920001778 nylon Polymers 0.000 claims description 22
- 239000004677 Nylon Substances 0.000 claims description 21
- FXJUUMGKLWHCNZ-UHFFFAOYSA-N dimethyl furan-2,3-dicarboxylate Chemical group COC(=O)C=1C=COC=1C(=O)OC FXJUUMGKLWHCNZ-UHFFFAOYSA-N 0.000 claims description 19
- 239000000706 filtrate Substances 0.000 claims description 18
- 239000000047 product Substances 0.000 claims description 16
- 108010031797 Candida antarctica lipase B Proteins 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- LKHUWNGGFCYROX-UHFFFAOYSA-N diethyl furan-2,3-dicarboxylate Chemical compound CCOC(=O)C=1C=COC=1C(=O)OCC LKHUWNGGFCYROX-UHFFFAOYSA-N 0.000 claims description 8
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- DZUAAFRNIXXDCM-UHFFFAOYSA-N 2,2,3,3-tetramethylpiperidin-1-amine Chemical compound CC1(C)CCCN(N)C1(C)C DZUAAFRNIXXDCM-UHFFFAOYSA-N 0.000 claims description 5
- YVORDIMCXSWNQQ-UHFFFAOYSA-N furan-2,5-dicarboxamide Chemical compound NC(=O)C1=CC=C(C(N)=O)O1 YVORDIMCXSWNQQ-UHFFFAOYSA-N 0.000 claims description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000012752 auxiliary agent Substances 0.000 abstract description 15
- 239000002184 metal Substances 0.000 abstract description 5
- 229910052751 metal Inorganic materials 0.000 abstract description 5
- 239000003513 alkali Substances 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 231100000331 toxic Toxicity 0.000 abstract description 2
- 230000002588 toxic effect Effects 0.000 abstract description 2
- 238000004817 gas chromatography Methods 0.000 description 14
- 239000000376 reactant Substances 0.000 description 7
- 238000000926 separation method Methods 0.000 description 6
- 101710098554 Lipase B Proteins 0.000 description 4
- 241001661345 Moesziomyces antarcticus Species 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 3
- 229920006122 polyamide resin Polymers 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 150000001263 acyl chlorides Chemical group 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000002028 Biomass Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- BMBDJILYIZBBMQ-UHFFFAOYSA-N furan-2,3-dicarbonyl chloride Chemical compound ClC(=O)C=1C=COC=1C(Cl)=O BMBDJILYIZBBMQ-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/16—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing two or more hetero rings
-
- 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
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Abstract
The application discloses a preparation method of an enzyme-catalyzed bio-based nylon auxiliary agent, belonging to the technical field of enzyme-catalyzed synthesis. Dialkyl furan dicarboxylate and tetramethyl piperidine amine are used as raw materials, the raw materials react in an organic solvent at a lower reaction temperature under the catalysis of an enzyme catalyst, and after the reaction is finished, a reaction mixed solution is post-treated to prepare the target product biobased nylon auxiliary N, N' -bis (2, 6-tetramethyl-4-piperidyl) 2, 5-furan dimethylformamide. The method disclosed by the invention does not relate to high-risk and toxic reagents such as metal catalysts, alkali and the like. The method does not involve high temperature conditions, the reaction temperature is 30-45 ℃, the reaction temperature is mild and safe, and the requirement on equipment is low. The content of the obtained product on a gas chromatograph can reach more than 99 percent, and the yield can reach more than 95 percent.
Description
Technical Field
The invention relates to a preparation method of an enzyme-catalyzed bio-based nylon auxiliary agent, belonging to the technical field of enzyme-catalyzed synthesis.
Background
Nylon (Nylon) is also called polyamide resin (PA), has the characteristics of light weight, no toxicity, excellent mechanical strength, strong wear resistance and corrosion resistance, has wide application in the fields of machinery, instruments, chemical industry, automobiles and the like, and can be used for replacing metals such as copper and the like to manufacture parts such as gears, bearings, pump blades and the like. The polyamide resin is spun into filaments after being melted, and can be used as synthetic fibers, medical sutures and the like. In actual production, because the polymer main chain of nylon is provided with repeated amide groups (-NH-CO-), the polarity of the amide groups (-NH-CO-) is larger, and the nylon is a chromophore group, so that the nylon is easily influenced by external environment, and the main chain of the macromolecule is broken, thereby influencing various properties of the nylon and the color of the product. Therefore, in the processing and production processes of nylon, chemical additives are required to be added to improve the product performance of nylon and prolong the service life of nylon.
The biological nylon auxiliary agent N, N' -bis (2, 6-tetramethyl-4-piperidyl) 2, 5-furandicarboxamide is a novel nylon auxiliary agent, and the auxiliary agent molecule contains a plurality of nitrogen, oxygen and other heteroatoms, and can be effectively combined with a nylon main chain through intermolecular hydrogen bonds, so that the processing stability of nylon melt is effectively improved, the nylon can keep heat stability and light stability for a long time, the dyeing performance of the nylon is improved, the light fastness of nylon fibers is improved, and the service life of the nylon is prolonged. The bio-based nylon auxiliary agent is a compound with a structural formula shown in a formula I;
the product is prepared by taking furan dicarboxylic acid chloride and tetramethyl piperidine amine as raw materials by a traditional synthesis method, and the preparation method has the advantages that the acyl chloride functional group has high reaction activity, and can be easily and quickly reacted with the amino group of the tetramethyl piperidine amine to prepare the target nylon auxiliary agent. The method has the defects that the acyl chloride is easy to hydrolyze and difficult to store stably, the reaction is required to be continuously carried out under the anhydrous condition, the reaction is required to be quenched and post-treated by alkali after the reaction is finished, the purification process is complex, and a large amount of sewage is easy to generate.
In recent years, patent reports develop a synthetic method for preparing the nylon auxiliary agent by taking dialkyl furandicarboxylate and tetramethyl piperidine amine as raw materials, wherein the method often needs high temperature conditions and needs to add a metal alkoxide catalyst (for example, sodium methoxide, and patent CN105452243A and CN 107109053A). The preparation method has harsh conditions, and has safety and environmental protection problems,
disclosure of Invention
Aiming at the defects and shortcomings of the prior art, the invention provides an enzyme catalysis preparation method of nylon auxiliary N, N' -bis (2, 6-tetramethyl-4-piperidyl) 2, 5-furandicarboxamide, which takes bio-based small molecular compound dialkyl furandicarboxylate from biomass resources as a starting material, and reacts with tetramethyl piperidine amine in an organic solvent under the catalysis of candida antarctica lipase B (lipase B from Candida antarctica) at a lower reaction temperature, so that a target product can be generated efficiently and in high yield, and the post-treatment mode is simple and easy to operate; the method is green and safe, does not involve the risks of high temperature, metal catalysts, alkali and the like, is not environment-friendly, and is safe and easy to operate.
In order to solve the technical problems, the invention adopts the following technical scheme: dialkyl furan dicarboxylate and tetramethyl piperidine amine are used as raw materials, and the target product is prepared by reacting in an organic solvent at a lower reaction temperature under the catalysis of candida antarctica lipase B (lipase B from Candida antarctica).
In a specific embodiment, the reaction conditions are: the reaction temperature is 30-45 ℃; the reaction time is 1 to 24 hours; the organic solvent is as follows: one or more of methyl tertiary butyl ether, diethyl ether, diisopropyl ether, tetrahydrofuran, 1, 4-dioxane, toluene, acetonitrile, acetone, dichloroethane, and n-hexane; the enzyme catalyst is as follows: candida antarctica lipase B (lipase B from Candida antarctica).
In a specific embodiment, the mass ratio of the enzyme catalyst to the raw material dialkyl furandicarboxylate is 1 (1-5); the ratio of the raw materials of dialkyl furandicarboxylate to tetramethyl piperidine amine is: 1, (2.5-5); the dialkyl furandicarboxylate is dimethyl furandicarboxylate or diethyl furandicarboxylate.
The method of the invention also comprises the necessary post-treatment of the reaction liquid: the post-treatment step of the invention is that after the reaction is finished, the reaction mixture is filtered, the solid separation is washed by water, the filtrate is collected, and the filtrate is concentrated, thus obtaining the target product.
The beneficial effects that this application can produce include:
1. the invention discloses a method for preparing a bio-based nylon auxiliary N, N' -bis (2, 6-tetramethyl-4-piperidinyl) 2, 5-furandicarboxamide by catalysis of candida antarctica lipase B (lipase B from Candida antarctica), which does not involve high-risk and toxic reagents such as metal catalysts, alkali and the like.
2. The method does not involve high temperature condition, the reaction temperature is 30-45 ℃, the reaction temperature is mild and safe, and the requirement on equipment is low.
3. The content of the product obtained by the method on a gas chromatograph can be more than 99 percent, and the yield can be more than 95 percent.
Drawings
FIG. 1 is a high resolution mass spectrum of a biobased nylon aid prepared according to example 3 of the present invention, demonstrating that the target nylon aid has been prepared.
Detailed Description
The present application is described in detail below with reference to examples, but the present application is not limited to these examples.
Unless otherwise indicated, the starting materials and enzyme catalysts (commercial CAS numbers for the enzyme catalysts: 9001-62-1; starting materials dimethyl furandicarboxylate and diethyl furandicarboxylate were both available from Zhejiang sugar technologies Co., ltd.) were both commercially available in the examples of the present application.
Example 1
The preparation method of the enzyme-catalyzed bio-based nylon auxiliary agent comprises the following steps:
to a mixed solution (1M) of dimethyl furandicarboxylate (184 mg,1 equivalent) in diisopropyl ether (184 mL) at 45℃was added tetramethyl piperidinamine (2.5 equivalent), followed by candida antarctica lipase B (CAL B) (73.5 mg) thereto, and the reaction was continued at 45℃for 2 hours. After the reactant dimethyl furandicarboxylate disappears, the reaction mixture is filtered, the solid separation is washed by water, the filtrate is collected, and the filtrate is concentrated, so that the target product is obtained. The yield was 95% based on dimethyl furandicarboxylate, and the content was 99.8% by Gas Chromatography (GC).
Example 2
The preparation method of the enzyme-catalyzed bio-based nylon auxiliary agent comprises the following steps:
to a mixed solution (1M) of dimethyl furandicarboxylate (184 mg,1 equivalent) in diisopropyl ether (184 mL) at 45℃was added tetramethyl piperidinamine (4 equivalent), followed by candida antarctica lipase B (CAL B) (73.5 mg) thereto, and the reaction was continued at 45℃for 2 hours. After the reactant dimethyl furandicarboxylate disappears, the reaction mixture is filtered, the solid separation is washed by water, the filtrate is collected, and the filtrate is concentrated, so that the target product is obtained. The yield was 98% based on dimethyl furandicarboxylate and the content was 99.9% by Gas Chromatography (GC).
Example 3
The preparation method of the enzyme-catalyzed bio-based nylon auxiliary agent comprises the following steps:
to a mixed solution (1M) of dimethyl furandicarboxylate (184 mg,1 equivalent) in diisopropyl ether (184 mL) at 45℃was added tetramethyl piperidinamine (4 equivalent), followed by candida antarctica lipase B (CAL B) (61 mg) thereto, and the reaction was continued at 45℃for 2 hours. After the reactant dimethyl furandicarboxylate disappears, the reaction mixture is filtered, the solid separation is washed by water, the filtrate is collected, and the filtrate is concentrated, so that the target product is obtained. The yield was 97% based on dimethyl furandicarboxylate and the content was 99.9% by Gas Chromatography (GC).
Example 4
The preparation method of the enzyme-catalyzed bio-based nylon auxiliary agent comprises the following steps:
to a mixed solution (1M) of dimethyl furandicarboxylate (184 mg,1 equivalent) in diisopropyl ether (184 mL) at 30℃was added tetramethyl piperidinamine (4 equivalent), followed by candida antarctica lipase B (CAL B) (73.5 mg) thereto, and the reaction was continued at 30℃for 2 hours. After the reactant dimethyl furandicarboxylate disappears, the reaction mixture is filtered, the solid separation is washed by water, the filtrate is collected, and the filtrate is concentrated, so that the target product is obtained. The yield was 95% based on dimethyl furandicarboxylate, and the content was 99.8% by Gas Chromatography (GC).
Example 5
The preparation method of the enzyme-catalyzed bio-based nylon auxiliary agent comprises the following steps:
to a mixed solution (1M) of dimethyl furandicarboxylate (184 mg,1 eq.) in tetrahydrofuran (184 mL) at 45℃was added tetramethyl piperidine amine (4 eq.) followed by candida antarctica lipase B (CAL B) (73.5 mg) and the reaction was continued at 45℃for 2 hours. After the reactant dimethyl furandicarboxylate disappears, the reaction mixture is filtered, the solid separation is washed by water, the filtrate is collected, and the filtrate is concentrated, so that the target product is obtained. The yield was 96% based on dimethyl furandicarboxylate, and the content was 99.9% by Gas Chromatography (GC).
Example 6
The preparation method of the enzyme-catalyzed bio-based nylon auxiliary agent comprises the following steps:
to a toluene (184 mL) mixed solution (1M) of diethyl furandicarboxylate (184 mg,1 eq) at 45℃was added tetramethyl piperidine amine (4 eq), followed by candida antarctica lipase B (CAL B) (73.5 mg) thereto, and the reaction was continued at 45℃for 2 hours. After the reactant diethyl furandicarboxylate disappears, the reaction mixture is filtered, the solid isolate is washed by water, the filtrate is collected, and the filtrate is concentrated, so that the target product is obtained. The yield was 95% based on dimethyl furandicarboxylate, and the content was 99.4% by Gas Chromatography (GC).
Example 7
The preparation method of the enzyme-catalyzed bio-based nylon auxiliary agent comprises the following steps:
to a mixed solution (1M) of diethyl furandicarboxylate (212 mg,1 eq) in diisopropyl ether (212 mL) at 45℃was added tetramethyl piperidine amine (4 eq), followed by candida antarctica lipase B (CAL B) (42.4 mg) and the reaction was continued at 45℃for 24 hours. After the reactant diethyl furandicarboxylate disappears, the reaction mixture is filtered, the solid isolate is washed by water, the filtrate is collected, and the filtrate is concentrated, so that the target product is obtained. The yield was 98% based on diethyl furandicarboxylate and the content was 99.8% by Gas Chromatography (GC).
The foregoing description is only a few examples of the present application and is not intended to limit the present application in any way, and although the present application is disclosed in the preferred examples, it is not intended to limit the present application, and any person skilled in the art may make some changes or modifications to the disclosed technology without departing from the scope of the technical solution of the present application, and the technical solution is equivalent to the equivalent embodiments.
Claims (9)
1. A preparation method of an enzyme-catalyzed bio-based nylon auxiliary is characterized by comprising the following steps of: dialkyl furan dicarboxylate and tetramethyl piperidine amine are used as raw materials, the raw materials react in an organic solvent at a lower reaction temperature under the catalysis of an enzyme catalyst, and after the reaction is finished, a reaction mixed solution is post-treated to prepare the target product biobased nylon auxiliary N, N' -bis (2, 6-tetramethyl-4-piperidyl) 2, 5-furan dimethylformamide.
2. The method of claim 1, wherein the reaction conditions are: the reaction temperature is 30-45 ℃; the reaction time is 1 h-24 h.
3. The preparation method according to claim 1, wherein the organic solvent is one or more of methyl tertiary butyl ether, diethyl ether, diisopropyl ether, tetrahydrofuran, 1, 4-dioxane, toluene, acetonitrile, acetone, dichloroethane and n-hexane.
4. The method of claim 1, wherein the enzyme catalyst is candida antarctica lipase B.
5. The preparation method of claim 1, wherein the mass ratio of the enzyme catalyst to the raw material dialkyl furandicarboxylate is 1 (2.5-5).
6. The process according to claim 1, wherein the ratio of the amounts of the starting materials dialkyl furandicarboxylate and tetramethyl piperidylamine is 1 (1 to 5).
7. The method according to claim 1, wherein the dialkyl furandicarboxylate is dimethyl furandicarboxylate or diethyl furandicarboxylate.
8. The method according to claim 1, wherein after the completion of the reaction, the reaction mixture is filtered, the solid isolate is washed with water, the filtrate is collected, and the filtrate is concentrated to obtain the objective product.
9. The biobased nylon adjunct N, N' -bis (2, 6-tetramethyl-4-piperidinyl) 2, 5-furandicarboxamide prepared according to any one of claims 1-8 for use in the improvement of nylon properties.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310280939.7A CN116287049A (en) | 2023-03-21 | 2023-03-21 | Preparation method of enzyme-catalyzed bio-based nylon auxiliary |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310280939.7A CN116287049A (en) | 2023-03-21 | 2023-03-21 | Preparation method of enzyme-catalyzed bio-based nylon auxiliary |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116287049A true CN116287049A (en) | 2023-06-23 |
Family
ID=86802867
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310280939.7A Pending CN116287049A (en) | 2023-03-21 | 2023-03-21 | Preparation method of enzyme-catalyzed bio-based nylon auxiliary |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN116287049A (en) |
-
2023
- 2023-03-21 CN CN202310280939.7A patent/CN116287049A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105330643B (en) | Card is than the preparation method for Buddhist nun | |
| CN111233704B (en) | Method for preparing 6-aminocapronitrile product | |
| CN1687022A (en) | Method for synthesizing p-phenylene diisocyanate | |
| CN116287049A (en) | Preparation method of enzyme-catalyzed bio-based nylon auxiliary | |
| CN106399418B (en) | Method for preparing moxifloxacin side chain by biological method | |
| US20160168065A1 (en) | Novel synthetic process of adipic acid | |
| CN112661670A (en) | Method for preparing 1,6-hexamethylene dicarbamate in non-catalytic mode | |
| CN108276356B (en) | Preparation method of 3, 5-disubstituted thiazolidine-2-thioketone compound | |
| CN110483323B (en) | Preparation method of asymmetric imide compound | |
| CN109824629B (en) | Method for preparing 3-amino-5- (alpha-aminoethyl) tetrahydrofuran by using N-acetylglucosamine | |
| CN111116420B (en) | Preparation method of symmetrical urea compound | |
| CN109651235B (en) | Preparation method of nylon auxiliary agent | |
| CN109761848B (en) | Method for preparing nitrile | |
| CN108675971B (en) | Method for preparing 2, 5-furan dicarbaldehyde | |
| WO2012142326A1 (en) | A method of producing 5-hydroxypyridine-2-carboxylic acid from alginate | |
| CN113620826B (en) | Preparation method of D-p-hydroxyphenylglycine methyl ester hydrochloride suitable for industrial production | |
| CN117229270A (en) | Preparation method of bio-based nylon auxiliary agent | |
| CN115819232B (en) | Synthesis method of cycloalkyl acrylate compound | |
| CN117051050A (en) | Novel method for preparing amide compounds by biocatalysis | |
| CN117417257A (en) | Method for synthesizing amine compound by catalytic hydrogenation | |
| WO2022073506A1 (en) | Improved process for producing 1, 5-pentamethylene diisocyanate from cadaverine salt | |
| CN1445213A (en) | Method for synthesizing arylamine compound | |
| CN108047059B (en) | Method for preparing aromatic amine by aromatic ketone one-pot method | |
| CN1319954C (en) | Process for synthesizing benzoxazolinone compounds | |
| CN115504899A (en) | Synthesis process of N, N-dialkyl-3-methoxypropionamide |
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 |