CN107034251A - A kind of method of lipase-catalyzed synthesis L ascorbyl palmitates in ionic liquid - Google Patents
A kind of method of lipase-catalyzed synthesis L ascorbyl palmitates in ionic liquid Download PDFInfo
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- CN107034251A CN107034251A CN201710160577.2A CN201710160577A CN107034251A CN 107034251 A CN107034251 A CN 107034251A CN 201710160577 A CN201710160577 A CN 201710160577A CN 107034251 A CN107034251 A CN 107034251A
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- 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
- C12P17/02—Oxygen as only ring hetero atoms
- C12P17/04—Oxygen as only ring hetero atoms containing a five-membered hetero ring, e.g. griseofulvin, vitamin C
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- 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
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
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Abstract
The invention discloses a kind of method of lipase-catalyzed synthesis L ascorbyl palmitates in ionic liquid.This method is using ionic liquid as reaction medium, and L ascorbic acid is substrate with palmitic acid, and lipase-catalyzed synthesis L ascorbyl palmitates are promoted using microwave heating in microwave reaction device.The catalytic activity and selectivity of lipase are improved, efficiency of pcr product is improved, shortens the reaction time, and environmental pollution is small, meets the requirement of Green Chemistry.
Description
Technical field
The present invention relates to a kind of lipase-catalyzed synthesis L- Vitamin Cs of microwave radiation technology carried out in ion liquid medium
The method of sour palmitate, belongs to technical field of food biotechnology.
Background technology
Ascorbyl Palmitate (Ascorbyl Palmitate, AP) is used as a kind of efficient oxygen scavenger and synergy
Agent is widely used in dairy products and nutritional health food, is the antioxidant that China uniquely can be used for infant food,
It is mainly oxidation resistant to serve by reducing the concentration of oxygen in packaging system.Compared with conventional infant formulas milk powder,
The babies ' formula milk powder of new generation for adding AP is coordinating the equilibrium of each nutrient, promotes baby's normal development, extends product shelf
Unrivaled effect is played in terms of phase.
Synthesis AP method mainly has chemical synthesis and biological catalysis.Chemical synthesis uses the conducts such as the concentrated sulfuric acid, HF
Solvent and catalyst, make L-AA occur esterification (or ester exchange) reaction with palmitic acid (ester).Used in chemical reaction
To the concentrated sulfuric acid and HF of severe corrosive, the toxic solvents such as chloroform, toluene are used when isolating and purifying ester, while chemical synthesis
Also exist easily generation accessory substance, isolate and purify that complicated, cost of investment is big, easily human body caused damage, easily pollution environment etc. it is scarce
Point.And biological catalysis has that mild condition, process are easily controllable, energy consumption is low, typically human body will not be damaged, without pair
Product, the features such as isolate and purify easy to operate.In addition biocatalyst-enzyme can be reused, and greatly reduce cost.And
And No. nine files in 2016 issued according to People's Republic of China's national health and Family Planning Committee are provided " with palm
Sour (or ethyl palmitate) and ascorbic acid are raw material, and food additives vitamin-c palmitate is made through lipase-catalyzed reaction
Ester ".It must be obtained as the AP of food additives with enzyme catalysis method.
Enzymatic method prepares AP, mainly by the use of lipase as catalyst, L-AA is occurred with palmitic acid (ester) straight
Connect esterification (or ester exchange) reaction.But find that normal fat enzyme can be in organic solvent (tert-pentyl alcohol, uncle from research both domestic and external
Butanol etc.) progress of catalytic esterification in medium, but still suffer from that the reaction time is long, yield is relatively low, enzyme dosage is big, cost is high
The problems such as.Based on above present Research, how to shorten the reaction time, improve conversion ratio, while reducing lipase and volatility has
The use of machine solvent, which turns into, prepares AP urgent problems to be solved.
Since effectively accelerating organic reaction using microwave radiation from Gedye in 1986 etc., research of the people to microwave is got over
Come more deep.Microwave chemical with its it is unique the characteristics of, cause the concern of domestic and foreign scholars.Microwave current accelerates organic reaction master
Explained with the fuel factor and non-thermal effect of microwave.The fuel factor of microwave shows that its high-efficiency heating characteristic adds reaction rate
It hurry up.Compared to conventional heat transfer pattern, microwave homogeneous heating, speed is fast and without heating hysteresis quality and thermograde.Microwave
Non-thermal effect show that microwave radiation also acts as the effect of catalyst, change the dynamics of reaction, reduce reaction activation
Can, improve reaction rate.Since nineteen ninety, microwave is applied to biocatalysis field particularly in terms of nonaqueous phase enzymatic.
Influence of the microwave radiation to biocatalytic reaction is mainly manifested in：The microwave radiation of suitable intensity can make the active site of enzyme molecule
More " exposed ", be easy to preferably with Binding Capacity, as a result show enzyme activity rise.Microwave radiation can increase reaction system and bottom
The energy of thing molecule, strengthens the effective collision of substrate molecule, so as to realize the purpose for accelerating reaction rate.
Traditional organic solvent, the absorption efficiency to microwave is low, and volatile, and environment is polluted.Ionic liquid exists
It is in a liquid state at a temperature of room temperature or near room temperature, with excellent chemically and thermally mechanical stability, there is good substrate dissolubility, compared with
Wide temperature applicable range, and be the reaction medium of green almost without vapour pressure.Meanwhile, " controllability " of its own structure,
So that ionic liquid can have preferable assimilation effect to microwave energy.And there are some researches show, compared with organic solvent,
Lipase in ionic liquid compared with as shown in organic solvent higher catalytic activity and reaction stereo-and regio-selectivity.
The content of the invention
Mesh of the present invention is to provide a kind of method that lipase catalyzes and synthesizes AP in ionic liquid, shorten the reaction time,
Reduce environmental pollution, improve efficiency of pcr product.
Technical scheme is as follows：
Lipase-catalyzed synthesis AP method, comprises the following steps in a kind of ionic liquid：
L-AA, palmitic acid, molecular sieve, lipase and ionic liquid are added in bioreactor, by reactor
Move into microwave reaction device, enable microwave radiation and reacted.Reaction terminates rear reaction system and is centrifuged, and uses second
Acetoacetic ester washing solid phase twice, collects organic phase, and decompression obtains white solid crude product except solvent；Pass through chromatographic isolation again, receive
Collect sample component, merge organic phase, dry, decompression removes solvent, obtains white product.
The present invention is under microwave heating condition, AP to be catalyzed and synthesized in ionic liquid using lipase, is not only improved
The catalytic reaction activity and selectivity of lipase, reaction condition is gentle, process conditions are simple, shortens the reaction time, further reduces
Environmental pollution, meets the requirement of Green Chemistry, and preparing AP for biological method provides another successful example.
Wherein, above-mentioned lipase is to dredge the thermophilic hyphomycete lipase of cotton like, fold lipase from candida sp, the false silk ferment in the South Pole
Female lipase, porcine pancreatic lipase, rizolipase, Pseudomonas cepacia lipase, onion cloth kirschner bacterium lipase；Or above-mentioned one
Plant or a variety of lipase.
Wherein, the consumption of above-mentioned lipase is 1-5g/L.
Wherein, above-mentioned ionic liquid is three octyl methyl quaternary ammoniums, chlorination -1- pi-allyl -3- methylimidazole salts, 1- second
Base -3- N-Methylimidazoleacetics cation, 1- butyl -3- methylimidazolium chlorides, the chloroboric acid of 1- ethoxy -3- methylimidazoles four
Salt, 1- ethoxy -3- methylimidazoles dodecane sulfonate, 1- ethoxy -3- methylimidazole villaumites, 1- ethoxy -3- methyl
Imidazole bisulfate, 1- ethoxy -3- methylimidazolium nitrates；Or above-mentioned one or more mixed ionic liquid.
Wherein, the consumption of above-mentioned L-AA is 12-20g/L, and is 1 with the mol ratio of palmitic acid:1-1:8.
Wherein, above-mentioned enzymatic reaction temperature is 50-65 DEG C.
Wherein, the above-mentioned catalytic reaction time is 0-3h.
Wherein, above-mentioned molecular sieve is 3A, 4A type.
The radiant power that microwave heating is carried out to reaction is 30~200W, preferably 30~80W, radiation frequency 2000MHz.
In the present invention, optimal reaction condition is：60 DEG C of reaction temperature, radiant power 60W, radiation frequency is 2000MHz,
Reaction time is 1h.
Compared with the existing technology, beneficial effects of the present invention are embodied in：The present invention is used under microwave radiation technology in green ion
Lipase-catalyzed synthesis Ascorbyl Palmitate in liquid medium, it is not only easy to operate, it is swift in response, and improve fat
The selectivity of fat enzyme, improves efficiency of pcr product.Green ionic liquid is employed as reaction medium simultaneously, that is, is improved to microwave
Assimilation effect, promotes microwave effect, and environmental pollution is reduced again, meets the requirement of Green Chemistry.
Embodiment
With reference to specific embodiment, the present invention is furture elucidated, but the invention is not restricted to this.
High performance liquid chromatography (HPLC) analysis condition：Different time takes out appropriate amount of sample Chromatographic Pure Methanol from reactor
Dilution is placed in sample bottle.To prevent the decomposition of sample, it is loaded at once into HPLC instrument (Agilent 1200Series HPLC)
Middle analysis.Chromatographic column：Eclipse XDB-C18 (5 μm, 4.6mm, 250mm, Agilent), detector：DAD (245nm), post
Temperature：25 DEG C, mobile phase:Methanol/water/H3PO4(95/5/0.1), flow velocity：1.0mL/min, sample size：10μL.With ascorbic acid palm fibre
Glycerin monostearate standard sample calculates product AP yield.
Sample processing conditions：After reaction terminates, reaction system is centrifuged, and washs with ethyl acetate solid phase two
It is secondary, organic phase is collected, decompression obtains white solid crude product except solvent；Pass through chromatographic isolation again, collect sample component, merge organic
Phase, is dried, and decompression removes solvent, obtains white product.
Embodiment 1
The present embodiment probes into the difference of the lipase-catalyzed reaction of conventional heating and microwave heating in organic solvent.
With the lipase-catalyzed reaction of conventional heating：
Added in bioreactor 0.2mM L-AAs, 1.0mM palmitic acids, 24mg/mL 3A molecular sieves and
(the Candida antarctica lipase immobilized on of 1.2mg/mL lipase Novozym 435
Macroporous polyacrylic resin), the 3mL tert-butyl alcohols, 60 DEG C of constant temperature water bath, reacting the AP yields after 6h is
25.8%.
The lipase-catalyzed reaction of microwave heating：
Added in microwave reactor 0.2mM L-AAs, 1.0mM palmitic acids, 24mg/mL 3A molecular sieves and
Microwave reactor is moved into microwave reaction device, enables microwave spoke by 1.2mg/mL lipase Novozym 435, the 3mL tert-butyl alcohols
Penetrate, set 60 DEG C of reaction temperature, radiant power 30W, radiation frequency is 2000MHz, the AP yields after reaction 1h are 60.8%.
Embodiment 2
The present embodiment probes into difference of the lipase-catalyzed reaction of microwave heating in organic solvent and in ionic liquid.
Microwave heats lipase-catalyzed reaction in organic solvent：
Added in microwave reactor 0.2mM L-AAs, 1.0mM palmitic acids, 24mg/mL 3A molecular sieves and
Microwave reactor is moved into microwave reaction device, enables microwave spoke by 1.2mg/mL lipase Novozym 435, the 3mL tert-butyl alcohols
Penetrate, set 60 DEG C of reaction temperature, radiant power 30W, radiation frequency is 2000MHz, the AP yields after reaction 1h are 59.5%.
Lipase-catalyzed reaction is heated in Microwave Irradiation in Ionic Liquids：
Added in microwave reactor 0.2mM L-AAs, 1.0mM palmitic acids, 24mg/mL 3A molecular sieves and
1.2mg/mL lipase Novozym 435 and 3mL ionic liquid tOMATFA (Trioctylmethylammonium
Trifluoroacetate), microwave reactor is moved into microwave reaction device, enables microwave radiation, set 60 DEG C of reaction temperature,
Radiant power 30W, radiation frequency is 2000MHz, and the AP yields after reaction 1h are 74.8%.
Embodiment 3
The present embodiment probes into the difference for heating lipase-catalyzed reaction with different capacity microwave in ionic liquid.
In ionic liquid lipase-catalyzed reaction is heated with 30W power microwaves：
Added in microwave reactor 0.2mM L-AAs, 1.0mM palmitic acids, 24mg/mL 3A molecular sieves and
1.2mg/mL lipase Novozym 435 and 3mL ionic liquid tOMATFA, microwave reaction device is moved into by microwave reactor,
60 DEG C of reaction temperature is set, radiant power 30W, radiation frequency is 2000MHz, the AP yields after reaction 1h are 74.8%.
In ionic liquid lipase-catalyzed reaction is heated with 60W power microwaves：
Added in microwave reactor 0.2mM L-AAs, 1.0mM palmitic acids, 24mg/mL 3A molecular sieves and
1.2mg/mL lipase Novozym 435 and 3mL ionic liquid tOMATFA, microwave reaction device is moved into by microwave reactor,
60 DEG C of reaction temperature is set, radiant power 60W, radiation frequency is 2000MHz, and the AP yields that reaction is 1h are 80.1%.
Embodiment 4
The present embodiment probes into the difference for aiding in lipase-catalyzed reaction with microwave treatment different time in ionic liquid.
Microwave treatment 5min is used in ionic liquid：
1.2mg/mL lipase Novozym 435 and 3mL ionic liquid tOMATFA are added in bioreactor, will
Microwave reactor moves into microwave reaction device, and radiant power 30W enables microwave radiation 5min and (maintains treatment temperature to be no more than 60
DEG C), then 0.2mM L-AAs, 1.0mM palmitic acids, 24mg/mL3A molecular sieves are added in bioreactor, setting reaction
Temperature 60 C, radiant power 30W, radiation frequency is 2000MHz, and the AP yields after reaction 1h are 83.2%.
Microwave treatment 15min is used in ionic liquid：
1.2mg/mL lipase Novozym 435 and 3mL ionic liquid tOMATFA are added in bioreactor, will
Microwave reactor moves into microwave reaction device, and radiant power 30W enables microwave radiation 15min and (maintains treatment temperature to be no more than 60
DEG C), then 0.2mM L-AAs, 1.0mM palmitic acids, 24mg/mL 3A molecular sieves are added in bioreactor, setting is anti-
Temperature 60 C is answered, radiant power 30W, radiation frequency is 2000MHz, the AP yields after reaction 1h are 87.4%.
Described above is only the preferred embodiment of the present invention, it should be pointed out that：For the ordinary skill people of the art
For member, under the premise without departing from the principles of the invention, some improvements and modifications can also be made, these improvements and modifications also should
This is considered as protection scope of the present invention.
Claims (8)
1. a kind of method of lipase-catalyzed synthesis Ascorbyl Palmitate in ionic liquid, it is characterised in that including with
Lower step：
L-AA, palmitic acid, molecular sieve, lipase and ionic liquid are added in bioreactor, reactor is moved into
Microwave reaction device, enables microwave radiation and is reacted, after reaction terminates, and described L-AA palm fibre is obtained by post processing
Glycerin monostearate.
2. the method for lipase-catalyzed synthesis Ascorbyl Palmitate in ionic liquid according to claim 1, its
It is characterised by, described ionic liquid is three octyl methyl quaternary ammoniums, chlorination -1- pi-allyl -3- methylimidazole salts, 1- second
Base -3- N-Methylimidazoleacetics cation, 1- butyl -3- methylimidazolium chlorides, the chloroboric acid of 1- ethoxy -3- methylimidazoles four
Salt, 1- ethoxy -3- methylimidazoles dodecane sulfonate, 1- ethoxy -3- methylimidazole villaumites, 1- ethoxy -3- methyl
One or more mixtures in imidazole bisulfate, 1- ethoxy -3- methylimidazolium nitrates.
3. the method for lipase-catalyzed synthesis Ascorbyl Palmitate in ionic liquid according to claim 1, its
It is characterised by, described lipase is to dredge the thermophilic hyphomycete lipase of cotton like, fold lipase from candida sp, antarctic candida
Lipase, porcine pancreatic lipase, rizolipase, Pseudomonas cepacia lipase or onion cloth kirschner bacterium lipase.
4. the method for lipase-catalyzed synthesis Ascorbyl Palmitate in ionic liquid according to claim 1, its
It is characterised by, the consumption of described lipase is 1.2~2.5% (mass percents) of substrate total amount sum.
5. the method for lipase-catalyzed synthesis Ascorbyl Palmitate in ionic liquid according to claim 1, its
It is characterised by, the mol ratio of the L-AA and palmitic acid is 1:1-1:8.
6. the method for lipase-catalyzed synthesis Ascorbyl Palmitate in ionic liquid according to claim 1, its
It is characterised by, 50~65 DEG C of the controlling reaction temperature, the reaction time is 0~3h.
7. the method for lipase-catalyzed synthesis Ascorbyl Palmitate in ionic liquid according to claim 1, its
It is characterised by, the radiant power that microwave heating is carried out to reaction is 30~200W, 500~2000MHz of radiation frequency.
8. the method for lipase-catalyzed synthesis Ascorbyl Palmitate in ionic liquid according to claim 1, its
It is characterised by, the molecular sieve is 3A or 4A types.
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Cited By (2)
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| CN110760913A (en) * | 2019-09-30 | 2020-02-07 | 东莞东阳光科研发有限公司 | Formation liquid, low-pressure formation foil and preparation method thereof |
| CN111607625A (en) * | 2020-04-24 | 2020-09-01 | 惠州市康维健生物科技有限公司 | Method for producing ascorbyl palmitate by enzyme method |
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| CN111607625A (en) * | 2020-04-24 | 2020-09-01 | 惠州市康维健生物科技有限公司 | Method for producing ascorbyl palmitate by enzyme method |
| CN111607625B (en) * | 2020-04-24 | 2024-01-19 | 惠州市康维健生物科技有限公司 | Method for producing ascorbyl palmitate by enzymatic method |
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Application publication date: 20170811 |