CN111171088B - Catalytic selective synthesis method of fatty acid oligosaccharide monoester - Google Patents
Catalytic selective synthesis method of fatty acid oligosaccharide monoester Download PDFInfo
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- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
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Abstract
The invention discloses a catalytic selective synthesis method of fatty acid oligosaccharide monoester. The method comprises the following steps: adding oligosaccharide, fatty acid or fatty acid ester and mesoporous catalyst into a reaction solvent for mixing reaction; then filtering, concentrating, recrystallizing and drying to obtain the fatty acid oligosaccharide monoester. The adopted multiphase limited-domain catalytic selective conversion strategy directly synthesizes series monofatty acid oligosaccharide ester by adjusting proper acidity or alkalinity and accurately controlling the matching of a pore structure and the monofatty acid oligosaccharide ester structure, and has high purity and yield; the reaction process is efficient and clean, the refining and purifying process is simple and convenient to operate, energy-saving and environment-friendly, the mesoporous catalyst can be recycled, the performance is kept, the method is suitable for large-scale production, and the toxic residue risk of organic (metal) catalysis and the high cost of biological enzyme catalysis are avoided.
Description
Technical Field
The invention belongs to the technical field of fine chemical engineering, and particularly relates to a catalytic selective synthesis method of fatty acid monoester.
Background
The fatty acid monoester is a bio-based functional chemical, has excellent surface activity, antibacterial and anti-inflammatory activities and other biological activities, is non-toxic and easily biodegradable, and can be applied to the industrial fields of food, cosmetics, medicines, ecological agriculture and the like. Because the molecular structure of the oligosaccharide contains a plurality of hydroxyl groups with similar activities, sugar ester mixtures such as fatty acid oligosaccharide monoester, fatty acid oligosaccharide diester, fatty acid oligosaccharide ester and the like are obtained by traditional acid-base catalytic synthesis, the monoester content in the mixtures can be improved only by a multi-step refining and purifying process, and the monoester product is directly synthesized by selective esterification in actual production. In scientific research, the controlled synthesis method of the fatty acid oligosaccharide ester mainly comprises an organic catalysis method and an enzyme catalysis method, and respectively adopts methods of protection-deprotection, organic (metal) catalysis, lipase, protease and the like.
For example, Barros et al are based on the Mitsunobu reaction, adding equal equivalents of sucrose, fatty acids, tribenzenePhenylphosphine (PPh)3) Synthesizing 6-O-monofatty acid sucrose ester and 6' -O-monofatty acid sucrose ester by using a reagent and a diisopropyl azodicarboxylate (DIAD) reagent; vlahov and the like adopt equivalent dibutyltin oxide as an activating reagent, react with cane sugar to form a methyltin subunit acetal intermediate, and then react with fatty acid anhydride in anhydrous N, N-dimethylformamide to selectively synthesize 6-O-monofatty acid sucrose ester, wherein the selectivity is more than 95%; ferrer and the like adopt silica gel to fix H.Lanuginosa lipase, and catalyze sucrose and fatty acid to synthesize 6-O-monofatty acid sucrose ester through esterification.
However, the organic catalytic synthesis method of the fatty acid monoester has the problems of large use of organic reagents, environmental sensitivity of metal complexes, high experimental operation requirements, difficult product separation and the like; the enzymatic synthesis method has the problems of poor tolerance and stability of an enzyme preparation to a solvent and a reactant, high cost and the like.
In view of the existing problems, it is an urgent need to develop a catalytic selective synthesis method for synthesizing monofatty acid oligosaccharide ester cleanly and efficiently.
Disclosure of Invention
The invention aims to: the problems in the prior art are solved, and a catalytic selective synthesis method of the fatty acid oligosaccharide ester is provided, so that the fatty acid oligosaccharide ester is synthesized cleanly and efficiently.
In order to achieve the aim, the invention provides a strategy for synthesizing fatty acid oligosaccharide ester through heterogeneous confinement catalytic selective synthesis, which comprises the steps of regulating a proper amount of acidity or alkalinity and accurately controlling a pore channel structure to be matched with the fatty acid oligosaccharide ester structure, carrying out esterification (or ester exchange) reaction on oligosaccharide and fatty acid (or ester) in pore channels in narrow distribution of a mesoporous catalyst to generate fatty acid oligosaccharide ester, leaving the generated fatty acid oligosaccharide ester out of the pore channels through mass transfer, entering a solvent body, and slightly increasing the molecular dynamics size due to the fact that the surface activity of the fatty acid oligosaccharide ester is subjected to molecular directional arrangement to form micelles or relaxation in the solvent, so that the fatty acid oligosaccharide ester is difficult to enter the pore channels for reaction, thereby preparing the high-yield and high-purity fatty acid oligosaccharide ester.
The prior reports rarely disclose mesoporous catalytic technologies for selective synthesis of monofatty acid oligosaccharide esters, and part of the mesoporous catalytic technologies uses acid-base modified MCM-41, SBA-15 and the like as mesoporous catalysts, the matching degree of the most probable pore diameter of the mesoporous catalytic technologies and the monofatty acid oligosaccharide esters is poor, the pore diameter distribution range is relatively large, due to the essential characteristics of similar polyhydroxy activities of oligosaccharide molecular structures, the oligosaccharide or monofatty acid oligosaccharide ester is easy to generate di-fatty acid oligosaccharide esters and even poly-fatty acid oligosaccharide esters by using too large pore channel reaction space of the catalysts in the reaction process, and efficient selective synthesis of the monofatty acid oligosaccharide esters is difficult to achieve.
The specific technical scheme is as follows:
in a first aspect of the invention, a catalytic selective synthesis method of fatty acid oligosaccharide ester is provided. According to an embodiment of the invention, the method comprises the steps of:
mixing oligosaccharide and fatty acid or fatty acid ester for reaction under the mesoporous catalyst to obtain fatty acid monosaccharide ester;
the mesoporous catalyst is at least one of mesoporous catalyst MBC-01, mesoporous catalyst MBC-02 and mesoporous catalyst MBC-03.
According to the embodiment of the invention, the mixture is reacted at 80-120 ℃ and 0.1-100 KPa.
According to the embodiment of the invention, the pore channel of the mesoporous catalyst is an ordered mesoporous pore channel, the most probable pore diameter is 2.0-3.5 nm, and the length of the pore channel is 20-100 nm.
According to an embodiment of the present invention, the mesoporous catalyst has a maximum pore size 0.1 to 0.5nm larger than that of the synthesized mono fatty acid oligosaccharide ester.
According to the embodiment of the invention, the molecular size of the fatty acid is 0.8-1.8 nm, and the structural formula of the fatty acid is R1COOH, wherein, R1Is C8～C18A hydrocarbon group of (a); the mesoporous catalyst is ordered mesoporous silicon oxide or ordered mesoporous carbon, at least one of carboxyl, sulfonic group, heteropoly acid and organic tin is loaded on the inner surface of a pore channel of the mesoporous catalyst, and the acid content is 0.8-1.2 mmol/g.
According to the embodiment of the invention, the molecular size of the fatty acid ester is 0.8-1.8 nm, and the structural formula of the fatty acid ester is shown in the specification
Wherein R is1Is C8～C18A hydrocarbon group of R2Is C1～C4A hydrocarbon group of (a); the mesoporous catalyst is ordered mesoporous silicon oxide or ordered mesoporous carbon, at least one of alkali metal oxide, alkaline earth metal oxide, organic amine and ammonium hydroxide is loaded on the inner surface of a pore channel of the mesoporous catalyst, and the alkali content is 0.8-1.2 mmol/g.
According to the embodiment of the invention, the molecular size of the oligosaccharide is 0.8-1.5 nm, and the oligosaccharide is disaccharide or trisaccharide formed by connecting five-carbon sugar units or six-carbon sugar units through glycosidic bonds.
According to an embodiment of the present invention, the oligosaccharide is selected from one of sucrose, lactose, maltose, trehalose, raffinose, and mannotriose.
According to an embodiment of the present invention, the fatty acid or fatty acid ester is selected from one of methyl laurate, lauric acid, methyl stearate, and methyl caprylate.
According to the embodiment of the invention, the mass ratio of the oligosaccharide to the mesoporous catalyst is 1: 0.05-0.5; the molar mass ratio of the oligosaccharide to the fatty acid or the fatty acid ester is 1 (1-3).
According to the embodiment of the invention, the reaction solvent is at least one of N, N-dimethylformamide and dimethyl sulfoxide.
According to the embodiment of the invention, the recrystallization solvent is at least one of diethyl ether and ethyl acetate.
The invention can be used for the surface modification of series of acids or alkalis and the precise and controllable synthesis of mesoporous catalysts with pore channel structures, the most probable pore diameter is 2.0-3.5 nm, the pore diameter distribution is concentrated, and the most probable pore diameter is less than or equal to +/-0.2 nm.
The invention calculates the molecular size of the monofatty acid oligosaccharide ester to be synthesized by theoretical simulation, strictly controls the acid-base basicity and the pore channel structure of the mesoporous catalyst to be matched with the synthesis of the monofatty acid oligosaccharide ester (the acid amount ranges from 0.8 to 1.2mmol/g, and the base amount ranges from 0.8 to 1.2 mmol/g).
In addition, the invention can accurately control the pore structure and the acidity and alkalinity in the pore, can realize the directional high-efficiency synthesis of the monofatty acid oligosaccharide ester,
the invention has the beneficial effects that:
(1) the invention adopts a heterogeneous confinement catalytic selective synthesis strategy to directly prepare the high-purity high-yield mono-fatty acid oligosaccharide ester, has clean and efficient process, simple and convenient operation and lower production cost, and is suitable for large-scale production.
(2) The method adopts the mesoporous catalyst with proper acidity or alkalinity and the accurate matching of the pore channel structure and the structure of the mono-fatty acid oligosaccharide ester, selectively synthesizes the monoester in the pore channel of the mesoporous catalyst, inhibits the generation of the diester, and improves the yield and the purity of the monoester.
(3) The mesoporous catalyst provided by the invention has centralized pore size distribution and is accurate and controllable;
(4) the method for synthesizing the fatty acid oligosaccharide monoester by catalytic selection has the advantages of easy separation of the catalyst and good recycling performance.
Detailed Description
In order to make the objects, technical solutions and technical effects of the present invention more clear, the present invention will be described in further detail with reference to specific embodiments. It should be understood that the detailed description and specific examples, while indicating the preferred embodiment of the invention, are intended for purposes of illustration only and are not intended to limit the scope of the invention.
Example 1
A catalytic selective synthesis method of sucrose monolaurate comprises the following steps:
1) adding 342g of sucrose (molecular size is about 0.9nm) and 214g of methyl laurate (molecular size is about 1.2nm) into DMF (dimethylformamide) solvent, and stirring and reacting under the conditions of 34.2g of mesoporous catalyst MBC-01 (most probable pore diameter is 2.3nm, alkali amount is 1.2mmol/g), 110 ℃ and 0.5 KPa;
2) TLC (thin layer chromatography) tracks the reaction progress, no sucrose is detected after 8h, the reaction is stopped by cooling, MBC-01 is removed by filtering and separating, filter residue is collected and washed by DMF, filtrate is combined, reduced pressure concentration is carried out to recover reaction solvent, concentrate is recrystallized by ethyl acetate, crystal is collected by cooling to room temperature, and sucrose monolaurate is obtained by vacuum drying at 50 ℃. Sucrose monolaurate had a purity of 98% and a yield of 96%.
Example 2
A catalytic selective synthesis method of sucrose monolaurate comprises the following steps:
1) adding 342g sucrose (molecular size about 0.9nm) and 214g lauric acid (molecular size about 1.1nm) into DMF solvent, stirring and reacting under the conditions of 34.2g mesoporous catalyst MAC-01 (most probable pore diameter is 2.3nm, acid amount is 1.0mmol/g), 120 ℃ and 0.5 KPa;
2) TLC (thin layer chromatography) tracks the reaction progress, no sucrose is detected after 6h, the reaction is stopped by cooling, the mesoporous catalyst MAC-01 is removed by filtering and separating, the obtained filter residue is washed by DMF, the filtrate is combined, the reaction solvent is recovered by decompression and concentration, the concentrate is recrystallized by ethyl acetate, the crystal is collected by cooling to the room temperature, and the sucrose monolaurate is obtained by vacuum drying at 50 ℃. Sucrose monolaurate was 95% pure and 88% yield.
Example 3
A catalytic selective synthesis method of maltose monostearate comprises the following steps:
1) adding 342g of maltose (molecular size is about 0.9nm) and 568g of methyl stearate (molecular size is about 1.8nm) into DMSO solvent, and stirring and reacting under the conditions of 68.4g of mesoporous catalyst MBC-02 (the most probable pore diameter is 3.0nm, the alkali content is 1.0mmol/g), 120 ℃ and 0.5 KPa;
2) TLC (thin layer chromatography) tracks the reaction progress, no sucrose is detected after 6h, the reaction is stopped by cooling, MBC-02 is removed by filtration and separation, the obtained filter residue is washed by DMSO, the filtrate is decompressed and concentrated to recover the reaction solvent, the concentrate is recrystallized by ethyl acetate, crystals are collected by cooling to room temperature, and the crystals are obtained by vacuum drying at 50 ℃. The purity was 96% and the yield was 90%.
Example 4
A catalytic selective synthesis method of raffinose monocaprylate comprises the following steps:
1) adding 504g of raffinose (molecular size about 1.4nm) and 158g of methyl caprylate (molecular size about 0.9nm) into DMF solvent, stirring and reacting under the conditions of 34.2g of mesoporous catalyst MBC-03 (most probable pore diameter 2.5nm, alkali amount 1.2mmol/g), 100 ℃ and 0.5 KPa;
2) TLC (thin layer chromatography) tracks the reaction progress, no raffinose is detected after 8h, the reaction is stopped by cooling, MBC-03 is removed by filtering and separating, the obtained filter residue is washed by DMF, the filtrate is decompressed and concentrated to recover the reaction solvent, the concentrate is recrystallized by diethyl ether, the crystal is collected by cooling to room temperature, and the raffinose monocaprylate is obtained by vacuum drying at 50 ℃. The purity was 97% and the yield was 95%.
Example 5
A catalytic selective synthesis method of raffinose monocaprylate is characterized in that a mesoporous catalyst MBC-03 is repeatedly utilized for an experiment, and comprises the following steps:
1) adding the mesoporous catalyst MBC-03' separated, washed and dried in the embodiment 4 into the same reaction system in the embodiment 4, reacting under the same conditions, recrystallizing the product with diethyl ether, and drying to obtain the raffinose monocaprylate with the purity of 97% and the yield of 94%;
2) the catalyst is repeatedly utilized to react under the same condition to prepare the raffinose monocaprylate with the purity of 97 percent and the yield of 94 percent.
Comparative example 1
A catalytic selective synthesis method of sucrose monolaurate comprises the following steps:
1) adding 342g of sucrose (molecular size is about 0.9nm) and 214g of methyl laurate (molecular size is about 1.2nm) into a DMF solvent, and stirring and reacting under the conditions of 34.2g of an alkali modified commercial mesoporous catalyst SBA-15 (the pore size distribution is 6.0-11.0nm, and the alkali content is 1.0mmol/g), 110 ℃ and 0.5 KPa;
2) TLC (thin-layer chromatography) tracks the reaction progress, no sucrose is detected after 8 hours, the reaction is stopped by cooling, the commercial mesoporous catalyst SBA-15 modified by alkali is removed by filtering and separating, filter residue is washed by DMF, filtrate is combined and then decompressed and concentrated to recover reaction solvent, concentrate is recrystallized by ethyl acetate, is cooled to room temperature to collect crystals, and is dried in vacuum at 50 ℃ to obtain the sucrose monolaurate with the purity of 35% and the yield of 83%.
Comparative example 2
A catalytic selective synthesis method of raffinose monocaprylate comprises the following steps:
1) adding 504g of raffinose (molecular size about 1.4nm) and 158g of methyl laurate (molecular size about 0.9nm) into a DMF solvent, and stirring for reaction under the conditions of 34.2g of an alkali modified commercial mesoporous catalyst MCM-41 (pore size distribution of 3.0-5.0nm and alkali content of 0.9mmol/g), 100 ℃ and 0.5 KPa;
2) TLC (thin layer chromatography) tracks the reaction progress, no raffinose is detected after 8h, the reaction is stopped by cooling, MBC-03 is removed by filtration and separation, filter residue is washed by DMF, filtrate is combined and then decompressed and concentrated to recover reaction solvent, concentrate is recrystallized by diethyl ether, crystal is collected by cooling to room temperature, and the crystal is collected by vacuum drying at 50 ℃ to obtain the raffinose monocaprylate with purity of 68% and yield of 89%.
According to the embodiment and the comparative example, the heterogeneous restricted catalytic selective conversion strategy adopted by the invention is obtained, and the series of monofatty acid oligosaccharide esters are directly synthesized by adjusting a proper amount of acidity or alkalinity and accurately controlling the pore structure to be matched with the structure of the monofatty acid oligosaccharide ester, so that the purity and the yield are high.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (6)
1. A catalytic selective synthesis method of fatty acid oligosaccharide ester is characterized in that: the method comprises the following steps:
mixing oligosaccharide and fatty acid or fatty acid ester for reaction under the mesoporous catalyst to obtain fatty acid monosaccharide ester;
the mesoporous catalyst is selected from at least one of mesoporous catalyst MBC-01, mesoporous catalyst MBC-02 and mesoporous catalyst MBC-03;
the molecular size of the most probable pore diameter of the mesoporous catalyst is 0.1-0.5nm larger than that of the synthesized fatty acid monosaccharide ester;
when oligosaccharide and fatty acid are mixed for reaction, the molecular size of the fatty acid is 0.8-1.8 nm, and the fatThe acid has the structural formula R1COOH, wherein, R1Is C8～C18A hydrocarbon group of (a); the mesoporous catalyst is ordered mesoporous silicon oxide or ordered mesoporous carbon, at least one of carboxyl, sulfonic group, heteropoly acid and organic tin is loaded on the inner surface of a pore channel of the mesoporous catalyst, and the acid content is 0.8-1.2 mmol/g;
when the oligosaccharide and the fatty acid ester are mixed for reaction, the molecular size of the fatty acid ester is 0.8-1.8 nm, and the structural formula of the fatty acid ester is shown in the specification
Wherein R is1Is C8～C18A hydrocarbon group of R2Is C1～C4A hydrocarbon group of (a); the mesoporous catalyst is ordered mesoporous silicon oxide or ordered mesoporous carbon, at least one of alkali metal oxide, alkaline earth metal oxide, organic amine and ammonium hydroxide is loaded on the inner surface of a pore passage of the mesoporous catalyst, and the alkali content is 0.8-1.2 mmol/g;
the pore channel of the mesoporous catalyst is an ordered mesoporous pore channel, the most probable pore diameter is 2.0-3.5 nm, and the length of the pore channel is 20-100 nm.
2. The method of synthesis according to claim 1, characterized in that: in the range of 80 to 120oC. Mixing and reacting under the condition of 0.1-100 KPa.
3. The method of synthesis according to claim 1, characterized in that: the molecular size of the oligosaccharide is 0.8-1.5 nm, and the oligosaccharide is disaccharide or trisaccharide formed by connecting a five-carbon sugar unit or a six-carbon sugar unit through glycosidic bonds.
4. The method of synthesis according to claim 1, characterized in that: the oligosaccharide is selected from one of sucrose, lactose, maltose, trehalose, raffinose and mannotriose.
5. The method of synthesis according to claim 1, characterized in that: the fatty acid or fatty acid ester is selected from one of methyl laurate, lauric acid, methyl stearate and methyl caprylate.
6. The method of synthesis according to claim 1, characterized in that: the mass ratio of the oligosaccharide to the mesoporous catalyst is 1 (0.05-0.5); the molar mass ratio of the oligosaccharide to the fatty acid or the fatty acid ester is 1 (1-3).
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Address after: 510665 Guangzhou, Guangdong, Tianhe District Province Road West, No. 318 Patentee after: Institute of chemical engineering, Guangdong Academy of Sciences Address before: 510665 Guangzhou, Guangdong, Tianhe District Province Road West, No. 318 Patentee before: GUANGDONG RESEARCH INSTITITUTE OF PETROCHEMICAL AND FINE CHEMICAL ENGINEERING |
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