CN103898176A - Method for ultrasonic assisted enzymatic synthesis of D-ascorbic acid palmitate - Google Patents
Method for ultrasonic assisted enzymatic synthesis of D-ascorbic acid palmitate Download PDFInfo
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- CN103898176A CN103898176A CN201410103965.3A CN201410103965A CN103898176A CN 103898176 A CN103898176 A CN 103898176A CN 201410103965 A CN201410103965 A CN 201410103965A CN 103898176 A CN103898176 A CN 103898176A
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Abstract
The invention relates to a method for ultrasonic assisted enzymatic synthesis of D-ascorbic acid palmitate, and belongs to the field of food biotechnology. The method comprises the following steps: with a D-erythorbic acid and a palmitic acid as raw materials, and immobilized lipase as a catalyst, carrying out direct esterification reaction; carrying out ultrasonic assisted non-aqueous enzyme catalytic reaction in an ultrasonic reactor; filtering and removing the immobilized lipase, a molecular sieve and un-reacted D-erythorbic acid from reaction liquid after reaction is ended; removing a solvent from the obtained filtrate by reduced pressure vaporization; dissolving the obtained residue by using ethyl acetate; washing by using deionized water, and separating out an ethyl acetate phase; removing the solvent ethyl acetate by reduced pressure evaporation again; and washing the obtained residue by using normal hexane, and drying in vacuum, so as to obtain the product. A green ultrasonic assisted non-aqueous enzyme catalysis technology is adopted, so that not only is the reaction time greatly shortened, but also the method has relatively high reaction selectivity and catalytic efficiency. Compared with a chemical synthesis method, the method is simple in process, small in pollution, mild in reaction condition, and applicable to industrial production.
Description
Technical field
The present invention relates to a kind of auxiliary method that strengthens the synthetic D-araboascorbic acid cetylate of nonaqueous phase enzyme process of ultrasonic technique of utilizing.Be particularly related to the technique of utilizing the synthetic D-araboascorbic acid cetylate of ultrasonic auxiliary enzymatic.Belong to technical field of food biotechnology.
Background technology
Food oils or oleaginous food are very easily subject to the effect such as light, heat, enzyme, metal ion in processing, storage, use procedure and that oxidative rancidity occurs is rotten, be especially rich in unsaturated double-bond vegetables oil deterioration by oxidation more easily occurs.Therefore, ensure oil quality safely, prevent oxidative rancidity and become that grease or oleaginous food are produced, stored key link.Except precision work, packing, normal employing added antioxidants retard grease and oleaginous food oxidation, is to store grease and the anti-oxidant effective means of oleaginous food.
D-araboascorbic acid (Erythorbic Acid, EA) be vitamins C (Ascorbic acid, VC) optical isomer, as novel natural food antioxidant, sanitas and preservation agent safe, excellent property, D-araboascorbic acid can reduce the oxidation of food effectively, prevent the change of taking off of its color, also can suppress the formation of carcinogenic substance nitrosamine in food simultaneously.There are some researches show, D-araboascorbic acid can strengthen the biological utilisation of non-blood red plain sheet.At present, D-araboascorbic acid is widely applied (FDA:http: //www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSear ch.cfmfr=182.3041 at industrial circles such as food, medicine, chemical industry; CAC:www.codexalimentarius.net/gsfaonline/index.html).China is largest production state and the global provisioning side of D-araboascorbic acid and sodium salt thereof, and industrial scale has reached 40000 tons/year of left and right, has occupied more than 80% international market share.But as antioxidant, D-araboascorbic acid is fat-soluble poor, can not directly apply to lipid food or makeup.Therefore,, in order to expand the range of application of D-araboascorbic acid, developing fat-soluble D-araboascorbic acid derivative stronger, that stability is higher is one of important channel.In the molecular structure of D-araboascorbic acid, on C-6, there is primary hydroxyl group, on C-5, there is secondary hydroxyl group, and contain enediol structural unit.Select suitable functional group, as there is oil loving long carbochain, respectively these functional groups are derived and can obtain D-araboascorbic acid esterified derivative, both wetting ability and the D-araboascorbic acid molecular structure unit with antioxygenation had been retained, increase again oil loving long carbochain hydrocarbyl portion and become amphipathic molecule, become the novel multifunctional additive that can be applied to lipid food simultaneously.
Similar with Ascorbyl Palmitate, D-araboascorbic acid cetylate, as the esterified derivative of D-araboascorbic acid, has anti-oxidant and nutrition reinforcing function, it is fat-soluble strong, in grease, antioxidant effect is remarkable, high temperature resistant, is applicable to oleaginous food, edible oil and makeup.But the correlative study of its enzymatic synthesis method report is less, more research relates to the synthetic of Ascorbyl Palmitate.Such as, the medium preparation method of ascorbyl palmitate (publication number: CN 102260231) that discloses of Deng Zhi in 2007, the method is mainly with the synthetic Quicifal of chemical process.This method is used the vitriol oil and is made catalyzer, instrument and equipment is had relatively high expectations, and easily cause environmental pollution.Consider that chemical process exists severe corrosive acid such as using the vitriol oil, hydrofluoric acid as catalyzer, temperature of reaction is higher, the material of instrument and equipment is had to strict requirement, in addition product needs extraction or post to separate in the process of purifying, and these methods also can be used a series of volatile organic solvents, easily pollute the critical defects such as environment.Zeng Yongqing in 2011 etc. disclose L-ascorbyl palmitate through non-aqueous phase enzymatic synthesis (publication number: CN 102127571), but the method exists the reaction times to grow the problems such as (20-50h) and productive rate are lower.Synthetic similar with Quicifal, the esterification of D-araboascorbic acid can be utilized chemical method or enzyme catalysis method.Compared with chemical method, enzyme catalysis method has that selectivity is high, side reaction is few, reaction conditions is gentle, the operation of product downstream separation is relatively simple and to advantages such as equipment requirements are lower, become at present the prefered method of synthetic (different) ascorbic acid derivates.But find from above-mentioned research, although lipase the carrying out of catalytic esterification preferably exists substrate D-araboascorbic acid poor solubility, transformation efficiency is lower, and the reaction times is long, and lipase consumption is large, high in cost of production problem.Based on above present Research, how to improve transformation efficiency, Reaction time shorten, the usage quantity that simultaneously reduces lipase becomes the synthetic saccharosonic acid cetylate problem demanding prompt solution of enzyme catalysis already.
Sonochemistry is utilize ultrasonic energy to accelerate and control chemical reaction, improve a frontier branch of science of the new chemical reaction of reaction yield and initiation, the formation, vibration, the growth that mainly come from acoustic cavitation-liquid hollow chamber are stretched and collapse, with the physical and chemical changes causing.Because ultrasonic wave has advantages of uniquely, non-secondary pollution, equipment are simple, wide application, so receive increasing concern, have related to the every field of chemistry, chemical industry at present.The ultrasonic application at synthesise vitamins C and A ester has been reported in research both at home and abroad, but has not yet to see about the report of the synthetic D-araboascorbic acid cetylate of ultrasonic auxiliary enzymatic open.
This patent intends providing a kind of method of utilizing the synthetic D-araboascorbic acid cetylate of intensified by ultrasonic wave enzymatic, the method is with respect to other immobilized enzyme catalysis reactions, significantly Reaction time shorten and minimizing enzyme usage quantity, and then improve esterification speed and efficiency, the production cost of D-araboascorbic acid cetylate is significantly reduced.
Summary of the invention
The object of this invention is to provide a kind of method of utilizing the synthetic D-araboascorbic acid cetylate of intensified by ultrasonic wave enzymatic, use the method can shorten the nonaqueous phase enzymatic esterification time and reduce enzyme usage quantity, and enhance esterification speed, thereby improve product preparation efficiency, realized and saved production cost and reduce environmental pollution.
for realizing above-mentioned purpose of the present invention:
A kind of method of utilizing the synthetic D-araboascorbic acid cetylate of intensified by ultrasonic wave enzymatic of the present invention, carry out according to following step: react as catalyzer carries out direct esterification taking D-araboascorbic acid and palmitinic acid as raw material, immobilized lipase (1), the mol ratio of D-araboascorbic acid and palmitinic acid is 1:1-1:10, molecular sieve add-on is 20-100g/L, non-aqueous phase medium is reaction solvent, and temperature of reaction is 30-70
oc, the consumption of immobilized lipase be substrate consumption and 0.5-20%(mass percent), ultrasonic auxiliary nonaqueous phase enzymic catalytic reaction 2-10h in ultrasonic reactor;
(2) after reaction finishes, reacting liquid filtering is removed immobilized lipase, molecular sieve and unreacted D-araboascorbic acid, and gained filtrate is through evaporation under reduced pressure removed solvent; Gained residuum acetic acid ethyl dissolution, washs with deionized water, separates ethyl acetate phase, again evaporation under reduced pressure removed solvent ethyl acetate; Gained residuum washs with normal hexane, and insolubles is in 50
oc vacuum-drying, obtains product D-araboascorbic acid cetylate.
Described ultrasonic reactor comprises the reaction unit of all configuration ultrasonic generators, such as numerical control frequency modulation ultrasonic generator, double frequency numerical control ultrasonic cleaner, 60kHz/300w ultrasonic generator and ultrasonic cell disruptor etc.
Described ultrasonic power is 60-300w.
Described ultrasonic frequency is 20-60kHz.
Described immobilized lipase comprises that all pass through physical adsorption, embedding, covalent attachment and crosslinked methods that D-araboascorbic acid and palmitinic acid can be catalyzed and synthesized to D-araboascorbic acid cetylate are fixed on Rhizopus lipase on carrier, Aspergillus lipase, Mucor lipase, mycocandida lipase, steapsase etc.
Described non-aqueous media is wherein a kind of material in acetone, tertiary amyl alcohol, the trimethyl carbinol, hexalin, normal hexane, tetrahydrofuran (THF), tetracol phenixin or the mixture of two kinds of materials.
Described immobilized enzyme serve as reasons a kind of aspergillus oryzae through gene modification (
aspergillus oryzae)microorganism carries out submerged fermentation and is adsorbed on a kind of macroporosity resin and makes Aspergillus lipase, and non-aqueous media is tertiary amyl alcohol, the trimethyl carbinol or acetone.
Described molecular sieve is 4 types.
It is more than 90% utilizing the purity of D-araboascorbic acid cetylate prepared by this kind of method, and products therefrom transformation efficiency is 30-95%.
The present invention, with respect to prior art, has following advantage:
Method provided by the invention can shorten preparation time greatly, has improved efficiency; The synthetic selectivity of enzyme process is high, and side reaction is few; Avoid adding the organic solvent of severe corrosive, required lower to the selectivity of equipment; Reaction conditions gentleness, the repeating utilization factor of enzyme improves; The solvent using in unreacted raw material and separation and purification of products can be reused by simple process, is convenient to the production of serialization.
brief description of the drawings
Fig. 1 is the synthetic D-araboascorbic acid cetylate process flow sheet of the ultrasonic auxiliary enzymatic of the present invention.Fig. 2 is ultrasonic assisted reaction setting drawing, wherein 1. water baths; 2. reactor; 3. ultra-sonic generator; 4. switch; 5. water pipe; 6. temperature control panel; 7. ultrasonic power control panel; 8. ultrasonic time control panel; 9. water level control panel.
Embodiment
Fig. 2 of the present invention is the reaction unit of the synthetic D-araboascorbic acid cetylate of ultrasonic auxiliary enzymatic, by water bath 1, and ultrasonic generator 3 and temperature control panel 6, ultrasonic power control panel 7, ultrasonic time control panel 8 and water level control panel 9 form.Esterification is carried out in the reactor 2 being fixed in water bath 1; Ultrasonic generator 3 is installed on the bottom of water bath, for generation of ultrasonic wave, and strengthening esterification; Switch 4 is for opening ultrasonic unit.Wherein the water level in the temperature in esterification reaction process, ultrasonic power, ultrasonic time and water bath all can regulate and control by button 6,7,8 and 9.Water pipe 5 is for the outflow that adds and finish rear water of tank water before starting shooting.
With specific examples, technical scheme of the present invention is described below, but protection scope of the present invention is not limited to this:
embodiment 1
In reactor, add 22g/L D-araboascorbic acid, 32g/L palmitinic acid, 20g/L 4 molecular sieves and substrate total amount and 0.5%(mass percent) immobilized lipase Novozym435,1000mL non-aqueous media normal hexane, be 60w in power, operating frequency is to react 6h, temperature of reaction 60 in the ultrasonic cleaning machine of 40kHz
oc; After reaction finishes, reacting liquid filtering is removed immobilized lipase, molecular sieve and unreacted D-araboascorbic acid, and gained filtrate is through 65
oc decompression rotary evaporation is removed solvent; Gained residuum acetic acid ethyl dissolution, and spend 4 times of ionized waters and wash, separate ethyl acetate phase, again through 50
oc decompression rotary evaporation is removed solvent ethyl acetate; Normal hexane washing 3 times for gained residuum, gained insolubles is in 50
oc vacuum-drying, obtains product D-araboascorbic acid cetylate.Gained D-araboascorbic acid cetylate 35.30 g, transformation efficiency is 68.22%, purity 90%.
embodiment 2
In reactor, add 22g/L D-araboascorbic acid, 320g/L palmitinic acid, 40g/L4 molecular sieve and substrate total amount and 20%(mass percent) immobilized lipase Lipozyme TLIM, 1000mL non-aqueous media normal hexane, be 300w in power, operating frequency is the numerical control frequency modulation ultrasonic generator reaction 4h of 40kHz, temperature of reaction 60
oc; After reaction finishes, reacting liquid filtering is removed immobilized lipase, molecular sieve and unreacted D-araboascorbic acid, and gained filtrate is through 65
oc decompression rotary evaporation is removed solvent; Gained residuum acetic acid ethyl dissolution, and spend 4 times of ionized waters and wash, separate ethyl acetate phase, again through 50
oc decompression rotary evaporation is removed solvent ethyl acetate; Normal hexane washing 3 times for gained residuum, gained insolubles is in 50
oc vacuum-drying, obtains product D-araboascorbic acid cetylate.Gained D-araboascorbic acid cetylate 47.55g, transformation efficiency is 91.89%, purity 89%.
embodiment 3
In reactor, add 22g/L D-araboascorbic acid, 128g/L palmitinic acid, 20g/L4 molecular sieve and substrate total amount and 7.5%(mass percent) immobilized lipase Novozym435,2000mL non-aqueous media normal hexane, be 180w in power, operating frequency is the numerical control frequency modulation ultrasonic generator reaction 4h of 40kHz, temperature of reaction 50
oc; After reaction finishes, reacting liquid filtering is removed immobilized lipase, molecular sieve and unreacted D-araboascorbic acid, and gained filtrate is through 65
oc decompression rotary evaporation is removed solvent; Gained residuum acetic acid ethyl dissolution, and spend 4 times of ionized waters and wash, separate ethyl acetate phase, again through 50
oc decompression rotary evaporation is removed solvent ethyl acetate; Normal hexane washing 3 times for gained residuum, gained insolubles is in 50
oc vacuum-drying, obtains product D-araboascorbic acid cetylate.Gained D-araboascorbic acid cetylate 96g, transformation efficiency is 92.86%, purity 94%.
embodiment 4
In reactor, add 22g/L D-araboascorbic acid, 160g/L palmitinic acid, 60g/L4 molecular sieve and substrate total amount and 15%(mass percent) immobilized lipase Lipozyme RMIM, 2000mL non-aqueous media normal hexane, be 120w in power, operating frequency is the ultrasonic cleaning machine reaction 4h of 20kHz, temperature of reaction 50
oc; After reaction finishes, reacting liquid filtering is removed immobilized lipase, molecular sieve and unreacted D-araboascorbic acid, and gained filtrate is through 65
oc decompression rotary evaporation is removed solvent; Gained residuum acetic acid ethyl dissolution, and spend 4 times of ionized waters and wash, separate ethyl acetate phase, again through 50
oc decompression rotary evaporation is removed solvent ethyl acetate; Normal hexane washing 3 times for gained residuum, gained insolubles is in 50
oc vacuum-drying, obtains product D-araboascorbic acid cetylate.Gained D-araboascorbic acid cetylate 89.74g, transformation efficiency is 90.71%, purity 92.8%.
embodiment 5
In reactor, add 22g/L D-araboascorbic acid, 96g/L palmitinic acid, 40g/L4 molecular sieve and substrate total amount and 10%(mass percent) immobilized lipase Novozym435,2000mL non-aqueous media normal hexane, be 200w in power, operating frequency is the ultrasonic cleaning machine reaction 6h of 40kHz, temperature of reaction 60
oc; After reaction finishes, reacting liquid filtering is removed immobilized lipase, molecular sieve and unreacted D-araboascorbic acid, and gained filtrate is through 65
oc decompression rotary evaporation is removed solvent; Gained residuum acetic acid ethyl dissolution, and spend 4 times of ionized waters and wash, separate ethyl acetate phase, again through 50
oc decompression rotary evaporation is removed solvent ethyl acetate; Normal hexane washing 3 times for gained residuum, gained insolubles is in 50
oc vacuum-drying, obtains product D-araboascorbic acid cetylate.Gained D-araboascorbic acid cetylate 95.95g, transformation efficiency is 87.71%, purity 90.6%.
Claims (8)
1. a method of utilizing the synthetic D-araboascorbic acid cetylate of intensified by ultrasonic wave enzymatic, is characterized in that carrying out according to following step:
(1) react as catalyzer carries out direct esterification taking D-araboascorbic acid and palmitinic acid as raw material, immobilized lipase, the mol ratio of D-araboascorbic acid and palmitinic acid is 1:1-1:10, molecular sieve add-on is 20-100g/L, and non-aqueous phase medium is reaction solvent, and temperature of reaction is 30-70
oc, the consumption of immobilized lipase be substrate consumption and 0.5-20%(mass percent), ultrasonic auxiliary nonaqueous phase enzymic catalytic reaction 2-10h in ultrasonic reactor;
(2) after reaction finishes, reacting liquid filtering is removed immobilized lipase, molecular sieve and unreacted D-araboascorbic acid, and gained filtrate is through evaporation under reduced pressure removed solvent; Gained residuum acetic acid ethyl dissolution, washs with deionized water, separates ethyl acetate phase, again evaporation under reduced pressure removed solvent ethyl acetate; Gained residuum washs with normal hexane, and insolubles is in 50
oc vacuum-drying, obtains product D-araboascorbic acid cetylate.
2. a kind of method of utilizing the synthetic D-araboascorbic acid cetylate of intensified by ultrasonic wave enzymatic according to claim 1, it is characterized in that described ultrasonic reactor comprises the reaction unit of all configuration ultrasonic generators, such as numerical control frequency modulation ultrasonic generator, double frequency numerical control ultrasonic cleaner, ultrasonic variable amplitude bar, 60kHz/300w ultrasonic generator, small power ultrasonic generator, high frequency ultrasound wave producer etc.
3. a kind of method of utilizing the synthetic D-araboascorbic acid cetylate of intensified by ultrasonic wave enzymatic according to claim 1, is characterized in that described ultrasonic power is 60-300w.
4. a kind of method of utilizing the synthetic D-araboascorbic acid cetylate of intensified by ultrasonic wave enzymatic according to claim 1, is characterized in that described ultrasonic frequency is 20-60kHz.
5. a kind of method of utilizing the synthetic D-araboascorbic acid cetylate of intensified by ultrasonic wave enzymatic according to claim 1, is characterized in that described immobilized lipase comprises that all pass through physical adsorption, embedding, covalent attachment and crosslinked methods that D-araboascorbic acid and palmitinic acid can be catalyzed and synthesized to D-araboascorbic acid cetylate are fixed on Rhizopus lipase on carrier, Aspergillus lipase, Mucor lipase, mycocandida lipase, steapsase etc.
6. a kind of method of utilizing the synthetic D-araboascorbic acid cetylate of intensified by ultrasonic wave enzymatic according to claim 1, is characterized in that described non-aqueous media is wherein a kind of material in acetone, tertiary amyl alcohol, the trimethyl carbinol, hexalin, normal hexane, tetrahydrofuran (THF), tetracol phenixin or the mixture of two kinds of materials.
7. a kind of method of utilizing the synthetic D-araboascorbic acid cetylate of intensified by ultrasonic wave enzymatic according to claim 1, it is characterized in that described immobilized enzyme serve as reasons a kind of aspergillus oryzae through gene modification (
aspergillus oryzae)microorganism carries out submerged fermentation and is adsorbed on a kind of macroporosity resin and makes Aspergillus lipase, and non-aqueous media is tertiary amyl alcohol, the trimethyl carbinol or acetone.
8. a kind of method of utilizing the synthetic D-araboascorbic acid cetylate of intensified by ultrasonic wave enzymatic according to claim 1, is characterized in that described molecular sieve is 4 types.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104480156A (en) * | 2014-12-19 | 2015-04-01 | 暨南大学 | L-ascorbyloleate as well as preparation method and application thereof |
| CN105647982A (en) * | 2016-02-29 | 2016-06-08 | 广州市食品工业研究所有限公司 | Method for enzymatic synthesis of L-AP (L-ascorbyl palmitate) under ultrasonic condition in combination with stirring method |
| CN106191142A (en) * | 2016-07-18 | 2016-12-07 | 中国农业科学院油料作物研究所 | A kind of preparation method of the biodiesel rich in phenolic acid structure ester |
| CN107034251A (en) * | 2017-03-17 | 2017-08-11 | 浙江工商大学 | A kind of method of lipase-catalyzed synthesis L ascorbyl palmitates in ionic liquid |
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| CN102127571A (en) * | 2010-01-15 | 2011-07-20 | 广州市食品工业研究所有限公司 | Method for producing L-ascorbyl palmitate through non-aqueous phase enzymatic synthesis |
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2014
- 2014-03-19 CN CN201410103965.3A patent/CN103898176A/en active Pending
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| CN102127571A (en) * | 2010-01-15 | 2011-07-20 | 广州市食品工业研究所有限公司 | Method for producing L-ascorbyl palmitate through non-aqueous phase enzymatic synthesis |
Non-Patent Citations (2)
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104480156A (en) * | 2014-12-19 | 2015-04-01 | 暨南大学 | L-ascorbyloleate as well as preparation method and application thereof |
| CN105647982A (en) * | 2016-02-29 | 2016-06-08 | 广州市食品工业研究所有限公司 | Method for enzymatic synthesis of L-AP (L-ascorbyl palmitate) under ultrasonic condition in combination with stirring method |
| CN105647982B (en) * | 2016-02-29 | 2019-04-23 | 广州市食品工业研究所有限公司 | The method of paddling process Enzyme catalyzed synthesis Ascorbyl Palmitate is combined under Ultrasonic Conditions |
| CN106191142A (en) * | 2016-07-18 | 2016-12-07 | 中国农业科学院油料作物研究所 | A kind of preparation method of the biodiesel rich in phenolic acid structure ester |
| CN106191142B (en) * | 2016-07-18 | 2018-08-14 | 中国农业科学院油料作物研究所 | A kind of preparation method of the biodiesel rich in phenolic acid structure ester |
| CN107034251A (en) * | 2017-03-17 | 2017-08-11 | 浙江工商大学 | A kind of method of lipase-catalyzed synthesis L ascorbyl palmitates in ionic liquid |
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