CN1316033C - Enzyme catalysis for producing sucrose fatty acid ester - Google Patents
Enzyme catalysis for producing sucrose fatty acid ester Download PDFInfo
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- CN1316033C CN1316033C CNB2005100443462A CN200510044346A CN1316033C CN 1316033 C CN1316033 C CN 1316033C CN B2005100443462 A CNB2005100443462 A CN B2005100443462A CN 200510044346 A CN200510044346 A CN 200510044346A CN 1316033 C CN1316033 C CN 1316033C
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Abstract
The present invention relates to a preparation method of sucrose fatty acid ester by enzyme catalysis. According to the range of a mole ratio of 1: 1 to 10, sucrose and fatty acid are put into a conical flask of 150 ml; organic solvents are added according to the proportion that 5 to 15 ml of organic solvents are added to 1 mol of sucrose; the conical flask filled with the mixtures is arranged in an HZ-9613Y type oil-bath thermostatic oscillator produced in the science and education instrument plant in Taicang City, Jiangsu Province at the constant temperature of 20 to 80 DEG C, and the conical flask is oscillated for 10 minutes; immobilized lipase with the amount of 0.01 to 0.5 times of that of the sucrose is added to the mixtures to be rotated at the rotating speed of 120 to 200 Rpm at the constant temperature of to 80 DEG C to react for 0.05 to 24 hours, and caustic soda is used for neutralizing residual lauric acid in the reaction solution; products are purified, dried in vacuum and crystallized to obtain sucrose fatty acid ester. The reactions can be carried out under atmospheric pressure by utilizing the method of the present invention which has the advantages of simple production process and low reaction temperature. Since the low-toxicity solvents are used, the sucrose fatty acid ester can be used in food and medicines; the purification of the product is simple, and the sucrose fatty acid ester with high purity can be obtained.
Description
Technical field
The present invention relates to sucrose is the method for raw material production sucrose fatty ester, relates in particular to the method for enzyme catalysis for producing sucrose fatty acid ester.
Background technology
In polyol-based non-ionic surfactant, saccharide fatty acid ester and alkyl-glucoside are the widest nonionogenic tensides of two class purposes.They are nontoxic, skin is had no stimulation, biological degradability is good, have decontamination, emulsification, washing, dispersion, moistening, infiltration, diffusion, foaming, antioxygen, viscosity adjustment, sterilization, prevent to wear out, antistatic and prevent multiple functions such as partial crystallization, in daily use chemicals, the food and medicine industry has obtained using widely.
Sucrose fatty ester (abbreviation sucrose ester), english abbreviation SE, it is a big class organic compound that is generated by sucrose and carboxylic acid reaction.It can be decomposed into glucose, lipid acid at human body, and then is absorbed as nutrient digestion by human body.And different with general synthetic tensio-active agent, the glucose ester can both 100% biological degradation under aerobic and anaerobic condition, help environmental protection, so it is a kind of green surfactant.Simultaneously, because the raw material sucrose and the lipid acid of sucrose ester are renewable resourcess, the use properties that sucrose ester is good, applied range etc., the extremely attention of scientific and technological circle.In recent decades, the research of sucrose ester has been obtained great achievement, and sucrose ester has become a prosperous day by day industry, its Application Areas is also in continuous expansion.Because its purposes constantly is developed, market potential is huge, has development prospect.
In addition, have research report sugar ester to have functions such as antitumor, antibacterial and desinsection, and proper amount of edible glucosides unsaturated fatty acid ester can reduce content of cholesterol and evidence of coronary heart diseases in the blood.Foreign latest report unsaturated fatty acids glucosides ester can be used in the skin cosmetics.
Traditional glycoside fatty acid ester synthetic method is a chemical method.Since on the sugar ring-and OH is numerous, and is poor with the chemical method synthesis of selective, and polymerization can take place in the sugar ring, and is difficult for carrying out the esterification of specific position, have a lot of by products to produce, productive rate is undesirable, and building-up reactions is carried out under high temperature, high pressure, condition is harsh, and the energy consumption height generally can cause sugared coking; And product is impure, has color.
Lipase-catalyzed synthetic sugar ester is the novel method of the synthetic sugar ester that occurred in recent years, utilize the regioselectivity of lipase, can synthesize the location-specific sugar ester of esterification from carbohydrate and the inexpensive raw material that is easy to get such as lipid acid or triglyceride level easily, and the reaction conditions gentleness, easy to operate.Because lipase has highly-solid selectively, regiospecificity and regioselectivity, but thereby the pure sugar ester of synthesizing optical, have important significance for theories and using value.
Because sugar and grease do not dissolve mutually, the direct esterification of carrying out sugar in strong polar organic solvent systems such as pyridine is mainly adopted in the research of lipase-catalyzed synthetic sugar ester in the current organic phase, or the form of sugar being made ketal or glucosides to be increasing its solvability, or adopts the immobilization system of hydrophilic support absorption sugar and enzyme.The synthetic sugar ester of enzyme process can carry out in organic solvents such as methyl-sulphoxide and pyridine, but because the influence of organic solvent, enzymatic one-step reaction productive rate is lower, and because the toxicity of organic solvent makes the sugar ester product be difficult to use in food or medicine.
Anqing is big, and Wu Keke (rolling up 65～68 pages of the 6th phases " Chinese oil " in 2004 the 29th) is a catalyzer with Novozym435 lipase, and normal hexane is an organic solvent, and propylene glycol is an emulsifying agent, enzymatic synthesis of glucose stearate.Result of study shows: the enzyme add-on is 10% of a lipid acid quality, and the mol ratio of substrate acid, sugar is 1: 1, and temperature is 60 ℃, water content is 513% of an organic solvent, reaction times is 4.5h, and when oscillation rate was 100r/min, the stearic acid maximum conversion rate can reach 93.40%.But reaction mixture is thickness very, and separation difficulty is difficult to obtain the high glucose fatty acid ester of purity.And the consumption of enzyme is big, the cost height.
Tu Maobing, Wei Dongzhi, Zheng Hong (East China University of Science's journal, Vol.28 No.2,176～179 pages) makes biological catalyst with immobilized lipase Novozym435 and successfully synthesized ethyl glucuronide glycosides oleic acid monoester in solvent-free system.Determining the suitableeest reaction conditions is: 80 ℃ of temperature, and initial water is divided into 0, and the concentration of enzyme is w enzyme=0.05, and the reaction times is 12h, oleic transformation efficiency 100%, the monoesters yield is 86.55%.
International Patent Application WO 8901480A discloses a kind of method, wherein contains the alkyl glycoside of 2～6 carbon atom alkyls and one and contains C
4～C
22(preferred C
6～C
22) lipid acid or its lower alkyl esters, in the reaction that exists in of lytic enzyme, lytic enzyme is selected from Rhizomucor, Humicola (Humicola), Rhodopseudomonas (Pseudomonas) or mycocandida (Candida).In two embodiment, used solvent is a 2-butanone, and its consumption is far longer than the gross weight of reactant, so can have the energy consumption height, the problem of aftertreatment difficulty during industrialization.
Summary of the invention
In order to overcome the deficiencies in the prior art part, the present inventor is through exploring and research, existing sucrose fatty ester production is transformed, found the method for enzyme catalysis sucrose fatty ester under normal pressure, production technique is simple, temperature of reaction is low, product is purified easy, can obtain highly purified sucrose fatty ester.
Enzyme catalysis of the present invention prepares the method for sucrose fatty ester, the steps include:
A) sucrose and lipid acid, 1: 1 in molar ratio～10 scope places the Erlenmeyer flask of 150ml;
B) ratio according to every mmol sucrose 5～15ml organic solvent adds organic solvent;
C) Erlenmeyer flask that will add said mixture places HZ-9613Y type oil bath isothermal vibration device (Taicang, Jiangsu science and education instrument plant product), and 20～80 ℃ of constant temperature shook 10 minutes;
D) add immobilized lipase, the consumption of immobilized lipase is 0.01～0.5 times of sucrose;
E) rotating speed 120～200r/min, 20～80 ℃ of constant temperature react after 0.05～24 hour, with phenolphthalein is indicator, with residual lauric acid in the sodium hydroxide neutralization reaction liquid of 5mol/L, adds 5～15mL dehydrated alcohol and 20～40mL chloroform then in reaction system, fully shake up, transfer in the separating funnel, isolate lower floor's extracting solution behind the standing demix, the upper strata chloroform extraction, lower floor's extracting solution and chloroform extraction liquid are merged, boil off solvent, vacuum-drying, crystallization obtains sucrose fatty ester.
Above-described sucrose is sucrose or beet sugar;
Above-described lipid acid is saturated or lipid acid unsaturated, straight chain or side chain, that contain 6 to 22 carbon atoms; Preferably, described lipid acid is saturated or lipid acid unsaturated, straight chain or side chain, that contain 8 to 20 carbon atoms; Preferred, described lipid acid is saturated or lipid acid unsaturated, straight chain or side chain, that contain 10 to 18 carbon atoms; Preferred, described lipid acid is: one or more in capric acid, lauric acid, tetradecanoic acid, palmitinic acid, stearic acid and/or the oleic acid; Most preferred, described lipid acid is lauric acid, oleic acid and/or stearic acid.
Above-mentioned steps c) and e), temperature of reaction is 20～80 ℃, preferred 30～50 ℃, and more preferably 35～45 ℃.
Above-mentioned steps a) in the mol ratio of sucrose and lipid acid be 1: 1～1: 10, preferred 1: 1～1: 8; More preferably 1: 1.2～1: 4.
Above-described organic solvent is C
2～C
10Alkane, alkene, alcohol, ketone or its mixture or with the mixture of water.Preferably, organic solvent is one or more in acetone, 2-butanone, ethanol, propyl alcohol, Virahol, the trimethyl carbinol, pentane, hexane, heptane, octane, sherwood oil, propylene glycol and/or the water; Preferred, organic solvent is one or more in acetone, 2-butanone, ethanol, the trimethyl carbinol, pentane, hexane, heptane, sherwood oil, propylene glycol and/or the water.Its optimal addn is every mmol sucrose 5～15ml solvent.
Above-mentioned steps e) reaction times in is 0.05～24 hour, preferred 5 minutes～18 hours, and more preferably 5 minutes～10 hours, more preferably 5 minutes～10 hours, more preferably 5 minutes～5 hours; More preferably 10 minutes～3 hours.
Above-described immobilized lipase is the lipase that is fixed on the carrier, and carrier is diatomite, gac, resin or textiles film; Immobilized lipase is selected from Rhizomucor miehei (Lipozyme, Trake Mark, ex.Novo, DenmarR), Candida antarctica, candida cylindracea Lipase (Sigma Chemical Co.USA), Novozym435 (NovoNordisk), porcine pancreatic lipase (PPL, Sigma company), candida cylindracea lipase (AYL, Japanese Amono Pharmacevtical Co., Ltd.), false pseudomonas bacillus lipase (PSL Japan Amono Pharmacevtical Co., Ltd.), penicillium expansum lipase (PEL, Nantong biochemical-pharmaceutical factory), yeast fat enzyme (CLL, Wuxi zymin factory), the lipase of L ipozyme RM (deriving from Mucor m iehei) (Beijing Novo Nordisk company) generation.Preferably, immobilized lipase is selected from Candida antarctica, candidacylindracea Lipase (Sigma Chemical Co.USA), Novozym435 (Novo Nordisk), porcine pancreatic lipase (PPL, Sigma company), candida cylindracea lipase (AYL, Japanese Amono Pharmacevtical Co., Ltd.), yeast fat enzyme (CLL, Wuxi zymin factory), the lipase of L ipozyme RM (deriving from Mucor m iehei) (Beijing Novo Nordisk company) generation.
The consumption of immobilized lipase is 0.01～0.5 times of sucrose, preferred 0.02～0.2 times, and more preferably 0.02～0.1 times.
Reaction back adds phenolphthalein and gives instruction agent with the NaOH titration of 0.05mol/l, determines transformation efficiency by the lipid acid amount before and after the assaying reaction system.
With tlc at developping agent: ethyl acetate: methyl alcohol: third acetate: water (60: 30: 5: assaying reaction product 5).
Can pass through the carrier combination technology, realize the immobilization of lipase on the carrier, also can directly buy immobilized lipase.The preparation of fibre immobilized lipase be with cotton fibre as immobilization material, cotton fibre is cut into small pieces, and is immersed in the enzyme liquid, soak 12h, take out back water flushing 2 times, 40 ℃ of vacuum-dryings.The preparation of chemically modified lipase is the normal hexane that resolvase and nonionogenic tenside is dissolved in certain volume, stirred 24 hours down at 4 ℃ then, and centrifugal acquisition filter cake, vacuum-drying is also pulverized.
The measuring method of lipase activity is to adopt the BP63 method to measure the activity of lipase, and its principle and step are as follows:
(1) principle: lipase decomposites acetic acid from Vanay, the concentration of the acetic acid that decomposes out with the sodium hydroxide solution titration.
(2) definition: a lipase unit is equivalent to discharge the required ester amount of 1 μ mol acetic acid under experiment condition.
(3) reagent: substrate solution: get the 5.9ml Vanay and splash in the 90ml distilled water, jolting is dissolved fully until Vanay, is settled to 100ml with distilled water then.
Sodium hydroxide solution: 0.05mol/l.
Enzyme solution: use the dissolved in distilled water enzyme, should contain about 400u in the 1ml solution.
(4) make step: the 50.0ml substrate solution is moved into one can thermoregulated in vitro (heating in water bath), is heated to 30 degrees centigrade while stirring, and the hydro-oxidation sodium solution transfers to 6.2 to 6.4 to pH value.Drip the 1.0ml enzyme solution then, and start the watch, under 30 degrees centigrade, stirring this reaction mixture and reach 30 minutes with the moderate speed, dropping sodium solution makes pH value at this moment remain on 6.2 to 6.4.Soaking time reads the consumption of sodium hydroxide solution when finishing, use with quadrat method and measure blank value.Just at this moment usefulness be in 100 degrees centigrade of water-baths passivation the enzyme solution of 4min.
The main value blank value
Substrate solution 50.0ml 50.0ml
Be warming up to 30 degrees centigrade, with sodium hydroxide solution pH value transferred to 6.2 to 6.4 and add
Enzyme solution 1.0ml-----
The enzyme solution of passivation-----1.0ml
Accurately be incubated 30min in 30 degrees centigrade while stirring, with the sodium hydroxide solution Continuous Titration of 0.05mol/l.Read the consumption of sodium hydroxide solution behind the 30min.
(5) calculate: the activity of calculating lipase as follows
(H-B)*50/Ew＝u/g
H in the formula: the consumption (ml) that is used for main value
B: the consumption (ml) that is used for blank value
50:50umol acetic acid=1ml0.05mol sodium hydroxide solution
The weight (g) that contains enzyme in the used enzyme solution of Ew:1ml
Method of the present invention is reacted under normal pressure, and production technique is simple; Temperature of reaction is 20～80 ℃, and temperature of reaction is low; Adopted hypotoxic solvent, can be used for food and medicine, and the product purification is easy, can obtain highly purified sucrose fatty ester.
Description of drawings
Fig. 1 is the infrared spectrogram of Surfhope SE Cosme C 1216.The ownership of each absorption peak is as follows:
3400～3500cm
-1Frequency multiplication absorption peak for the C=O stretching vibration;
3000～2860cm
-1Be the C-H stretching vibration absorption peak on methyl or the methylene radical;
1740cm
-1Be the C=O stretching vibration absorption peak (γ on the ester group
C=O);
1460cm
-1Be the C-H flexural vibration absorption peak on the methylene radical;
1375cm
-1Be the C-H flexural vibration absorption peak in the methyl;
1230～1100cm
-1C-O stretching vibration absorption peak for the C-O-C structure in the ester;
1015～950cm
-1Charateristic avsorption band for furan nucleus;
730cm
-1Be (CH
2)
nThe skeletal vibration absorption peak;
The results of FT-IR as can be seen, we are resulting result and literature value basically identical [CasimirC, Akoh, BarryG, etal, Optimizedsynthesisofsucrose polyester:comparsion of physical properties of sucrose polyester, raffinosepolyesterandsaladoils[J], JofFoodScience, 1990,55 (1): 236-243; Xie Deming, Zheng Jianxian, tall and big dimension, synthetic and analysis [J], Chinese oil, 1997,22 (4): 32-34. of new oil sucrose polyester], therefore can think that the sample of gained is that polyester and purity are also higher.
Embodiment
Again will the invention will be further elaborated in the following examples, but the invention is not restricted to this.
Embodiment 1
Accurately take by weighing 3 parts of 1.6025g lauric acid, place the Erlenmeyer flask of 3 150ml respectively, the glucose (sour sugared mol ratio is 4: 1) that in each Erlenmeyer flask, respectively adds 0.3964g again, add the 10ml propyl carbinol, place HZ-9613Y type oil bath isothermal vibration device (Taicang, Jiangsu science and education instrument plant product), 40 ℃ of constant temperature, shake and add the 0.4000g immobilized enzyme again after 10 minutes, 40 ℃ of constant temperature, rotating speed 150r/min reacted 10 hours.
Reaction back adds phenolphthalein and gives instruction agent with the NaOH titration of 0.05mol/l, determines transformation efficiency by the lipid acid amount before and after the assaying reaction system.Recording the lauric acid transformation efficiency is 10%.
With tlc at developping agent: ethyl acetate: methyl alcohol: third acetate: water (60: 30: 5: assaying reaction product 5).
With phenolphthalein is indicator, with residual lauric acid in the sodium hydroxide neutralization reaction liquid of 5mol/L, in reaction system, add 10mL dehydrated alcohol and 30mL chloroform then, fully shake up, transfer in the separating funnel, isolate lower floor's extracting solution behind the standing demix, the upper strata chloroform extraction merges lower floor's extracting solution and chloroform extraction liquid, boils off solvent, vacuum-drying obtains purified product 0.062g.
Embodiment 2
Accurately take by weighing 3 parts of 1.6025g lauric acid, place the Erlenmeyer flask of 3 150ml respectively, the glucose (sour sugared mol ratio is 4: 1) that in each Erlenmeyer flask, respectively adds 0.3964g again, add the 10ml normal hexane, place HZ-9613Y type oil bath isothermal vibration device (Taicang, Jiangsu science and education instrument plant product), 40 ℃ of constant temperature, shake and add the 0.4000g immobilized enzyme again after 10 minutes, 40 ℃ of constant temperature, rotating speed 150r/min reacted 8 hours.
Reaction back adds phenolphthalein and gives instruction agent with the NaOH titration of 0.05mol/l, determines transformation efficiency by the lipid acid amount before and after the assaying reaction system.Recording the lauric acid transformation efficiency is 70%.
With tlc at developping agent: ethyl acetate: methyl alcohol: third acetate: water (60: 30: 5: assaying reaction product 5).
With phenolphthalein is indicator, with residual lauric acid in the sodium hydroxide neutralization reaction liquid of 5mol/L, in reaction system, add 10mL dehydrated alcohol and 30mL chloroform then, fully shake up, transfer in the separating funnel, isolate lower floor's extracting solution behind the standing demix, the upper strata chloroform extraction merges lower floor's extracting solution and chloroform extraction liquid, boils off solvent, vacuum-drying obtains purified product 0.402g.
Embodiment 3
Accurately take by weighing 3 parts of 1.6025g lauric acid, place the Erlenmeyer flask of 3 150ml respectively, the glucose (sour sugared mol ratio is 4: 1) that in each Erlenmeyer flask, respectively adds 0.3964g again, add 5ml propylene glycol, 5ml normal hexane and 1ml water, place HZ-9613Y type oil bath isothermal vibration device (Taicang, Jiangsu science and education instrument plant product), 40 ℃ of constant temperature, shake and add the 0.4000g immobilized enzyme again after 10 minutes, 40 ℃ of constant temperature, rotating speed 150r/min reacted 10 hours.
Reaction back adds phenolphthalein and gives instruction agent with the NaOH titration of 0.05mol/l, determines transformation efficiency by the lipid acid amount before and after the assaying reaction system.Recording the lauric acid transformation efficiency is 61%.
With tlc at developping agent: ethyl acetate: methyl alcohol: third acetate: water (60: 30: 5: assaying reaction product 5).
With phenolphthalein is indicator, with residual lauric acid in the sodium hydroxide neutralization reaction liquid of 5mol/L, in reaction system, add 10mL dehydrated alcohol and 30mL chloroform then, fully shake up, transfer in the separating funnel, isolate lower floor's extracting solution behind the standing demix, the upper strata chloroform extraction merges lower floor's extracting solution and chloroform extraction liquid, boils off solvent, vacuum-drying obtains purified product 0.351g.
Embodiment 4
Accurately take by weighing 3 parts of 1.6025g lauric acid, place the Erlenmeyer flask of 3 150ml respectively, the glucose (sour sugared mol ratio is 4: 1) that in each Erlenmeyer flask, respectively adds 0.3964g again, add the 10ml trimethyl carbinol, place HZ-9613Y type oil bath isothermal vibration device (Taicang, Jiangsu science and education instrument plant product), 40 ℃ of constant temperature, shake and add the 0.4000g immobilized enzyme again after 10 minutes, 40 ℃ of constant temperature, rotating speed 150r/min reacted 12 hours.
Reaction back adds phenolphthalein and gives instruction agent with the NaOH titration of 0.05mol/l, determines transformation efficiency by the lipid acid amount before and after the assaying reaction system.Recording the lauric acid transformation efficiency is 5%.
With tlc at developping agent: ethyl acetate: methyl alcohol: third acetate: water (60: 30: 5: assaying reaction product 5).
With phenolphthalein is indicator, with residual lauric acid in the sodium hydroxide neutralization reaction liquid of 5mol/L, in reaction system, add 10mL dehydrated alcohol and 30mL chloroform then, fully shake up, transfer in the separating funnel, isolate lower floor's extracting solution behind the standing demix, the upper strata chloroform extraction merges lower floor's extracting solution and chloroform extraction liquid, boils off solvent, vacuum-drying obtains purified product 0.028g.
Embodiment 5
Accurately take by weighing 3 parts of 1.6025g lauric acid, place the Erlenmeyer flask of 3 150ml respectively, the glucose (sour sugared mol ratio is 4: 1) that in each Erlenmeyer flask, respectively adds 0.3964g again, do not add solvent, directly place HZ-9613Y type oil bath isothermal vibration device (Taicang, Jiangsu science and education instrument plant product), 40 ℃ of constant temperature, shake and add the 0.4000g immobilized enzyme again after 10 minutes, 40 ℃ of constant temperature, rotating speed 150r/min reacted 5 hours.
Reaction back adds phenolphthalein and gives instruction agent with the NaOH titration of 0.05mol/l, determines transformation efficiency by the lipid acid amount before and after the assaying reaction system.Recording the lauric acid transformation efficiency is 57%.
With tlc at developping agent: ethyl acetate: methyl alcohol: third acetate: water (60: 30: 5: assaying reaction product 5).
With phenolphthalein is indicator, with residual lauric acid in the sodium hydroxide neutralization reaction liquid of 5mol/L, in reaction system, add 10mL dehydrated alcohol and 30mL chloroform then, fully shake up, transfer in the separating funnel, isolate lower floor's extracting solution behind the standing demix, the upper strata chloroform extraction merges lower floor's extracting solution and chloroform extraction liquid, boils off solvent, vacuum-drying obtains purified product 0.324g.
Embodiment 6
Accurately take by weighing 3 parts of 1.6000g lauric acid, place the Erlenmeyer flask of 3 150ml respectively, the glucose (sour sugared mol ratio is 4: 1) that in each Erlenmeyer flask, respectively adds 0.3963g again, add the 15ml normal hexane, place HZ-9613Y type oil bath isothermal vibration device (Taicang, Jiangsu science and education instrument plant product), 40 ℃ of constant temperature, shake and add the 0.1280g immobilized enzyme again after 10 minutes, 40 ℃ of constant temperature, rotating speed 150r/min reacted 5 hours.
Reaction back adds phenolphthalein and gives instruction agent with the NaOH titration of 0.05mol/l, determines transformation efficiency by the lipid acid amount before and after the assaying reaction system.Recording the lauric acid transformation efficiency is 58%.
With tlc at developping agent: ethyl acetate: methyl alcohol: third acetate: water (60: 30: 5: assaying reaction product 5).
With phenolphthalein is indicator, with residual lauric acid in the sodium hydroxide neutralization reaction liquid of 5mol/L, in reaction system, add 10mL dehydrated alcohol and 30mL chloroform then, fully shake up, transfer in the separating funnel, isolate lower floor's extracting solution behind the standing demix, the upper strata chloroform extraction merges lower floor's extracting solution and chloroform extraction liquid, boils off solvent, vacuum-drying obtains purified product 0.348g.
Embodiment 7
Accurately take by weighing 3 parts of 1.6000g lauric acid, place the Erlenmeyer flask of 3 150ml respectively, the glucose (sour sugared mol ratio is 4: 1) that in each Erlenmeyer flask, respectively adds 0.3963g again, add the 15ml normal hexane, place HZ-9613Y type oil bath isothermal vibration device (Taicang, Jiangsu science and education instrument plant product), 40 ℃ of constant temperature, shake and add the 0.1600g immobilized enzyme again after 10 minutes, 40 ℃ of constant temperature, rotating speed 150r/min reacted 4 hours.
Reaction back adds phenolphthalein and gives instruction agent with the NaOH titration of 0.05mol/l, determines transformation efficiency by the lipid acid amount before and after the assaying reaction system.Recording the lauric acid transformation efficiency is 64.7%.
With tlc at developping agent: ethyl acetate: methyl alcohol: third acetate: water (60: 30: 5: assaying reaction product 5).
With phenolphthalein is indicator, with residual lauric acid in the sodium hydroxide neutralization reaction liquid of 5mol/L, in reaction system, add 10mL dehydrated alcohol and 30mL chloroform then, fully shake up, transfer in the separating funnel, isolate lower floor's extracting solution behind the standing demix, the upper strata chloroform extraction merges lower floor's extracting solution and chloroform extraction liquid, boils off solvent, vacuum-drying obtains purified product 0.360g.
Embodiment 8
Accurately take by weighing 3 parts of 1.6000g lauric acid, place the Erlenmeyer flask of 3 150ml respectively, the glucose (sour sugared mol ratio is 4: 1) that in each Erlenmeyer flask, respectively adds 0.3963g again, add the 15ml normal hexane, place HZ-9613Y type oil bath isothermal vibration device (Taicang, Jiangsu science and education instrument plant product), 40 ℃ of constant temperature, shake and add the 0.2037g immobilized enzyme again after 10 minutes, 40 ℃ of constant temperature, rotating speed 150r/min reacted 8 hours.
Reaction back adds phenolphthalein and gives instruction agent with the NaOH titration of 0.05mol/l, determines transformation efficiency by the lipid acid amount before and after the assaying reaction system.Recording the lauric acid transformation efficiency is 69.6%.
With tlc at developping agent: ethyl acetate: methyl alcohol: third acetate: water (60: 30: 5: assaying reaction product 5).
With phenolphthalein is that indication is sharp, with residual lauric acid in the sodium hydroxide neutralization reaction liquid of 5mol/L, in reaction system, add 10mL dehydrated alcohol and 30mL chloroform then, fully shake up, transfer in the separating funnel, isolate lower floor's extracting solution behind the standing demix, the upper strata chloroform extraction merges lower floor's extracting solution and chloroform extraction liquid, boils off solvent, vacuum-drying obtains purified product 0.366g.
Embodiment 9
Accurately take by weighing 3 parts of 1.6000g lauric acid, place the Erlenmeyer flask of 3 150ml respectively, the glucose (sour sugared mol ratio is 4: 1) that in each Erlenmeyer flask, respectively adds 0.3963g again, add the 15ml normal hexane, place HZ-9613Y type oil bath isothermal vibration device (Taicang, Jiangsu science and education instrument plant product), 40 ℃ of constant temperature, shake and add the 0.3030g immobilized enzyme again after 10 minutes, 40 ℃ of constant temperature, rotating speed 150r/min reacted 12 hours.
Reaction back adds phenolphthalein and gives instruction agent with the NaOH titration of 0.05mol/l, determines transformation efficiency by the lipid acid amount before and after the assaying reaction system.Recording the lauric acid transformation efficiency is 70%.
With tlc at developping agent: ethyl acetate: methyl alcohol: third acetate: water (60: 30: 5: assaying reaction product 5).
With phenolphthalein is indicator, with residual lauric acid in the sodium hydroxide neutralization reaction liquid of 5mol/L, in reaction system, add 10mL dehydrated alcohol and 30mL chloroform then, fully shake up, transfer in the separating funnel, isolate lower floor's extracting solution behind the standing demix, the upper strata chloroform extraction merges lower floor's extracting solution and chloroform extraction liquid, boils off solvent, vacuum-drying obtains purified product 0.412g.
Embodiment 10
Accurately take by weighing 3 parts of 1.6000g lauric acid, place the Erlenmeyer flask of 3 150ml respectively, the glucose (sour sugared mol ratio is 4: 1) that in each Erlenmeyer flask, respectively adds 0.3963g again, add the 15ml normal hexane, place HZ-9613Y type oil bath isothermal vibration device (Taicang, Jiangsu science and education instrument plant product), 40 ℃ of constant temperature, shake and add the 0.5020g immobilized enzyme again after 10 minutes, 40 ℃ of constant temperature, rotating speed 150r/min reacted 3 hours.
Reaction back adds phenolphthalein and gives instruction agent with the NaOH titration of 0.05mol/l, determines transformation efficiency by the lipid acid amount before and after the assaying reaction system.Recording the lauric acid transformation efficiency is 70.1%.
With tlc at developping agent: ethyl acetate: methyl alcohol: third acetate: water (60: 30: 5: assaying reaction product 5).
With phenolphthalein is indicator, with residual lauric acid in the sodium hydroxide neutralization reaction liquid of 5mol/L, in reaction system, add 10mL dehydrated alcohol and 30mL chloroform then, fully shake up, transfer in the separating funnel, isolate lower floor's extracting solution behind the standing demix, the upper strata chloroform extraction merges lower floor's extracting solution and chloroform extraction liquid, boils off solvent, vacuum-drying obtains purified product 0.412g.
Embodiment 11
Accurately take by weighing 3 parts of 1.6025g (8mmol) lauric acid, place the Erlenmeyer flask of 3 150ml respectively, the glucose that in each Erlenmeyer flask, respectively adds 0.1982g (1mmol) again, add the 10ml normal hexane, place HZ-9613Y type oil bath isothermal vibration device (Taicang, Jiangsu science and education instrument plant product), 40 ℃ of constant temperature, shake and add the 0.1923g immobilized enzyme again after 10 minutes, 40 ℃ of constant temperature, rotating speed 150r/min reacted 15 hours.
Reaction back adds phenolphthalein and gives instruction agent with the NaOH titration of 0.05mol/l, determines transformation efficiency by the lipid acid amount before and after the assaying reaction system.Recording the lauric acid transformation efficiency is 85%.
With tlc at developping agent: ethyl acetate: methyl alcohol: third acetate: water (60: 30: 5: assaying reaction product 5).
With phenolphthalein is indicator, with residual lauric acid in the sodium hydroxide neutralization reaction liquid of 5mol/L, in reaction system, add 10mL dehydrated alcohol and 30mL chloroform then, fully shake up, transfer in the separating funnel, isolate lower floor's extracting solution behind the standing demix, the upper strata chloroform extraction merges lower floor's extracting solution and chloroform extraction liquid, boils off solvent, vacuum-drying obtains purified product 0.480g.
Embodiment 12
Accurately take by weighing 3 parts of 1.6025g (8mmol) lauric acid, place the Erlenmeyer flask of 3 150ml respectively, the glucose that in each Erlenmeyer flask, respectively adds 0.1982g (1mmol) again, add the 10ml normal hexane, place HZ-9613Y type oil bath isothermal vibration device (Taicang, Jiangsu science and education instrument plant product), 30 ℃ of constant temperature, shake and add the 0.1923g immobilized enzyme again after 10 minutes, 30 ℃ of constant temperature, rotating speed 150r/min reacted 15 hours.
Reaction back adds phenolphthalein and gives instruction agent with the NaOH titration of 0.05mol/l, determines transformation efficiency by the lipid acid amount before and after the assaying reaction system.Recording the lauric acid transformation efficiency is 67%.
With tlc at developping agent: ethyl acetate: methyl alcohol: third acetate: water (60: 30: 5: assaying reaction product 5).
With phenolphthalein is indicator, with residual lauric acid in the sodium hydroxide neutralization reaction liquid of 5mol/L, in reaction system, add 10mL dehydrated alcohol and 30mL chloroform then, fully shake up, transfer in the separating funnel, isolate lower floor's extracting solution behind the standing demix, the upper strata chloroform extraction merges lower floor's extracting solution and chloroform extraction liquid, boils off solvent, vacuum-drying obtains purified product 0.405g.
Embodiment 13
Accurately take by weighing 3 parts of 1.6025g (8mmol) lauric acid, place the Erlenmeyer flask of 3 150ml respectively, the glucose that in each Erlenmeyer flask, respectively adds 0.1982g (1mmol) again, add the 10ml normal hexane, place HZ-9613Y type oil bath isothermal vibration device (Taicang, Jiangsu science and education instrument plant product), 35 ℃ of constant temperature, shake and add the 0.1923g immobilized enzyme again after 10 minutes, 35 ℃ of constant temperature, rotating speed 150r/min reacted 15 hours.
Reaction back adds phenolphthalein and gives instruction agent with the NaOH titration of 0.05mol/l, determines transformation efficiency by the lipid acid amount before and after the assaying reaction system.Recording the lauric acid transformation efficiency is 94%.
With tlc at developping agent: ethyl acetate: methyl alcohol: third acetate: water (60: 30: 5: assaying reaction product 5).
With phenolphthalein is indicator, with residual lauric acid in the sodium hydroxide neutralization reaction liquid of 5mol/L, in reaction system, add 10mL dehydrated alcohol and 30mL chloroform then, fully shake up, transfer in the separating funnel, isolate lower floor's extracting solution behind the standing demix, the upper strata chloroform extraction merges lower floor's extracting solution and chloroform extraction liquid, boils off solvent, vacuum-drying obtains purified product 0.525g.
Embodiment 14
Accurately take by weighing 3 parts of 1.6025g (8mmol) lauric acid, place the Erlenmeyer flask of 3 150ml respectively, the glucose that in each Erlenmeyer flask, respectively adds 0.1982g (1mmol) again, add the 10ml normal hexane, place HZ-9613Y type oil bath isothermal vibration device (Taicang, Jiangsu science and education instrument plant product), 40 ℃ of constant temperature, shake and add the 0.1923g immobilized enzyme again after 10 minutes, 40 ℃ of constant temperature, rotating speed 150r/min reacted 15 hours.
Reaction back adds phenolphthalein and gives instruction agent with the NaOH titration of 0.05mol/l, determines transformation efficiency by the lipid acid amount before and after the assaying reaction system.Recording the lauric acid transformation efficiency is 87%.
With tlc at developping agent: ethyl acetate: methyl alcohol: third acetate: water (60: 30: 5: assaying reaction product 5).
With phenolphthalein is indicator, with residual lauric acid in the sodium hydroxide neutralization reaction liquid of 5mol/L, in reaction system, add 10mL dehydrated alcohol and 30mL chloroform then, fully shake up, transfer in the separating funnel, isolate lower floor's extracting solution behind the standing demix, the upper strata chloroform extraction merges lower floor's extracting solution and chloroform extraction liquid, boils off solvent, vacuum-drying obtains purified product 0.465g.
Embodiment 15
Accurately take by weighing 3 parts of 1.6025g (8mmol) lauric acid, place the Erlenmeyer flask of 3 150ml respectively, the glucose that in each Erlenmeyer flask, respectively adds 0.1982g (1mmol) again, add the 10ml normal hexane, place HZ-9613Y type oil bath isothermal vibration device (Taicang, Jiangsu science and education instrument plant product), 45 ℃ of constant temperature, shake and add the 0.1923g immobilized enzyme again after 10 minutes, 45 ℃ of constant temperature, rotating speed 150r/min reacted 15 hours.
Reaction back adds phenolphthalein and gives instruction agent with the NaOH titration of 0.05mol/l, determines transformation efficiency by the lipid acid amount before and after the assaying reaction system.Recording the lauric acid transformation efficiency is 72%.
With tlc at developping agent: ethyl acetate: methyl alcohol: third acetate: water (60: 30: 5: assaying reaction product 5).
With phenolphthalein is indicator, with residual lauric acid in the sodium hydroxide neutralization reaction liquid of 5mol/L, in reaction system, add 10mL dehydrated alcohol and 30mL chloroform then, fully shake up, transfer in the separating funnel, isolate lower floor's extracting solution behind the standing demix, the upper strata chloroform extraction merges lower floor's extracting solution and chloroform extraction liquid, boils off solvent, vacuum-drying obtains purified product 0.405g.
Embodiment 16
Accurately take by weighing 3 parts of 1.6025g (8mmol) lauric acid, place the Erlenmeyer flask of 3 150ml respectively, the glucose that in each Erlenmeyer flask, respectively adds 0.1982g (1mmol) again, add the 10ml normal hexane, place HZ-9613Y type oil bath isothermal vibration device (Taicang, Jiangsu science and education instrument plant product), 50 ℃ of constant temperature, shake and add the 0.1923g immobilized enzyme again after 10 minutes, 50 ℃ of constant temperature, rotating speed 150r/min reacted 15 hours.
Reaction back adds phenolphthalein and gives instruction agent with the NaOH titration of 0.05mol/l, determines transformation efficiency by the lipid acid amount before and after the assaying reaction system.Recording the lauric acid transformation efficiency is 53%.
With tlc at developping agent: ethyl acetate: methyl alcohol: third acetate: water (60: 30: 5: assaying reaction product 5).
With phenolphthalein is indicator, with residual lauric acid in the sodium hydroxide neutralization reaction liquid of 5mol/L, in reaction system, add 10mL dehydrated alcohol and 30mL chloroform then, fully shake up, transfer in the separating funnel, isolate lower floor's extracting solution behind the standing demix, the upper strata chloroform extraction merges lower floor's extracting solution and chloroform extraction liquid, boils off solvent, vacuum-drying obtains purified product 0.308g.
Embodiment 17
Accurately take by weighing 3 parts of 0.5688g (2mmol) stearic acid, place the Erlenmeyer flask of 3 150ml respectively, the glucose that in each Erlenmeyer flask, respectively adds 0.3960g (2mmol) again, add 15ml normal hexane, 1ml propylene glycol and 1ml water, place HZ-9613Y type oil bath isothermal vibration device (Taicang, Jiangsu science and education instrument plant product), 50 ℃ of constant temperature, shake and add the 0.1016g immobilized enzyme again after 10 minutes, 50 ℃ of constant temperature, rotating speed 150r/min reacted 0.5 hour.
Reaction back adds phenolphthalein and gives instruction agent with the NaOH titration of 0.05mol/l, determines transformation efficiency by the lipid acid amount before and after the assaying reaction system.Recording the lauric acid transformation efficiency is 88%.
With tlc at developping agent: ethyl acetate: methyl alcohol: third acetate: water (60: 30: 5: assaying reaction product 5).
With phenolphthalein is indicator, with residual lauric acid in the sodium hydroxide neutralization reaction liquid of 5mol/L, in reaction system, add 10mL dehydrated alcohol and 30mL chloroform then, fully shake up, transfer in the separating funnel, isolate lower floor's extracting solution behind the standing demix, the upper strata chloroform extraction merges lower floor's extracting solution and chloroform extraction liquid, boils off solvent, vacuum-drying obtains purified product 0.487g.
Embodiment 18
Accurately take by weighing 3 parts of 0.5688g (2mmol) stearic acid, place the Erlenmeyer flask of 3 150ml respectively, the glucose that in each Erlenmeyer flask, respectively adds 0.3960g (2mmol) again, add 15ml normal hexane, 1ml propylene glycol and 1ml water, place HZ-9613Y type oil bath isothermal vibration device (Taicang, Jiangsu science and education instrument plant product), 60 ℃ of constant temperature, shake and add the 0.1130g immobilized enzyme again after 10 minutes, 60 ℃ of constant temperature, rotating speed 150r/min reacted 5 hours.
Reaction back adds phenolphthalein and gives instruction agent with the NaOH titration of 0.05mol/l, determines transformation efficiency by the lipid acid amount before and after the assaying reaction system.Recording the lauric acid transformation efficiency is 84.2%: methyl alcohol: third acetate: water (60: 30: 5: assaying reaction product 5).
With phenolphthalein is indicator, with residual lauric acid in the sodium hydroxide neutralization reaction liquid of 5mol/L, in reaction system, add 10mL dehydrated alcohol and 30mL chloroform then, fully shake up, transfer in the separating funnel, isolate lower floor's extracting solution behind the standing demix, the upper strata chloroform extraction merges lower floor's extracting solution and chloroform extraction liquid, boils off solvent, vacuum-drying obtains purified product 0.470g.
Embodiment 19
Accurately take by weighing 3 parts of 0.5690g (2mmol) stearic acid, place the Erlenmeyer flask of 3 150ml respectively, the glucose that in each Erlenmeyer flask, respectively adds 0.3965g (2mmol) again, add 15ml normal hexane, 1ml propylene glycol and 1ml water, place HZ-9613Y type oil bath isothermal vibration device (Taicang, Jiangsu science and education instrument plant product), 50 ℃ of constant temperature, shake and add the 0.0573g immobilized enzyme again after 10 minutes, 50 ℃ of constant temperature, rotating speed 150r/min reacted 2.5 hours.
Reaction back adds phenolphthalein and gives instruction agent with the NaOH titration of 0.05mol/l, determines transformation efficiency by the lipid acid amount before and after the assaying reaction system.Recording the lauric acid transformation efficiency is 81%.
With tlc at developping agent: ethyl acetate: methyl alcohol: third acetate: water (60: 30: 5: assaying reaction product 5).
With phenolphthalein is indicator, with residual lauric acid in the sodium hydroxide neutralization reaction liquid of 5mol/L, in reaction system, add 10mL dehydrated alcohol and 30mL chloroform then, fully shake up, transfer in the separating funnel, isolate lower floor's extracting solution behind the standing demix, the upper strata chloroform extraction merges lower floor's extracting solution and chloroform extraction liquid, boils off solvent, vacuum-drying obtains purified product 0.467g.
Embodiment 20
Accurately take by weighing 3 parts of 0.5249g (2mmol) oleic acid, place the Erlenmeyer flask of 3 150ml respectively, the glucose that in each Erlenmeyer flask, respectively adds 0.1982g (1mmol) again, add 15ml normal hexane, 6 propylene glycol and 3ml water, place HZ-9613Y type oil bath isothermal vibration device (Taicang, Jiangsu science and education instrument plant product), 40 ℃ of constant temperature, shake and add the 0.2g immobilized enzyme again after 10 minutes, 40 ℃ of constant temperature, rotating speed 150r/min reacted 10 minutes.
Reaction back adds phenolphthalein and gives instruction agent with the NaOH titration of 0.05mol/l, determines transformation efficiency by the lipid acid amount before and after the assaying reaction system.Recording the lauric acid transformation efficiency is 95%.
With tlc at developping agent: ethyl acetate: methyl alcohol: third acetate: water (60: 30: 5: assaying reaction product 5).
With phenolphthalein is indicator, with residual lauric acid in the sodium hydroxide neutralization reaction liquid of 5mol/L, in reaction system, add 10mL dehydrated alcohol and 30mL chloroform then, fully shake up, transfer in the separating funnel, isolate lower floor's extracting solution behind the standing demix, the upper strata chloroform extraction merges lower floor's extracting solution and chloroform extraction liquid, boils off solvent, vacuum-drying obtains purified product 0.537g.
Claims (4)
1. an enzyme catalysis prepares the method for sucrose fatty ester, the steps include:
A) sucrose and lauric acid, 1: 1 in molar ratio～10 scope places the Erlenmeyer flask of 150ml;
B) ratio according to every mmol sucrose 5-15ml organic solvent adds organic solvent;
C) Erlenmeyer flask that will add said mixture places HZ-9613Y type oil bath isothermal vibration device, constant temperature 30-50 ℃, shakes 10 minutes;
D) add immobilized lipase, the consumption of immobilized lipase is 0.01-0.5 a times of sucrose; Described immobilized lipase is selected from Candida antarctica, candida cylindracea Lipase, porcine pancreatic lipase, candida cylindracea lipase, yeast fat enzyme, the lipase that Lipozyme RM produces;
E) rotating speed 120-200r/min, reacts after 10 minutes～3 hours by constant temperature 30-50 ℃, with phenolphthalein is indicator, with residual lauric acid in the sodium hydroxide neutralization reaction liquid of 5mol/L, adds 5-15mL dehydrated alcohol and 20-40mL chloroform then in reaction system, fully shake up, transfer in the separating funnel, isolate lower floor's extracting solution behind the standing demix, the upper strata chloroform extraction, lower floor's extracting solution and chloroform extraction liquid are merged, boil off solvent, vacuum-drying, crystallization obtains Surfhope SE Cosme C 1216.
2. enzyme catalysis as claimed in claim 1 prepares the method for sucrose fatty ester, it is characterized in that:
Described sucrose is sucrose or beet sugar;
Described immobilized lipase is the lipase that is fixed on the carrier, and carrier is diatomite, resin or textiles film;
Described organic solvent is one or more in acetone, 2-butanone, ethanol, the trimethyl carbinol, pentane, hexane, heptane, sherwood oil, the propylene glycol.
3. enzyme catalysis as claimed in claim 1 prepares the method for sucrose fatty ester, it is characterized in that step c) and e) described in temperature range be 35-45 ℃.
4. enzyme catalysis as claimed in claim 1 prepares the method for sucrose fatty ester, it is characterized in that sucrose and lauric mol ratio are 1: 1.2～1: 4; The consumption of immobilized lipase is 0.02-0.1 a times of sucrose.
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| CN101705257B (en) * | 2009-11-13 | 2012-05-16 | 浙江工业大学 | Method for catalytic synthesis of sucrose ester by lipase in two phases of water and organic solvent |
| CN102181494A (en) * | 2011-03-21 | 2011-09-14 | 盐城捷康三氯蔗糖制造有限公司 | Synthesis of sucrose-6-fatty acid ester through selective catalysis of immobilized aspergillus oryzae lipase |
| JP2013099315A (en) * | 2011-10-14 | 2013-05-23 | Nisshin Oillio Group Ltd | Manufacturing method for sucrose fatty acid ester concentrate mixture and sucrose fatty acid ester concentrate mixture obtained thereby |
| CN103614433A (en) * | 2013-11-06 | 2014-03-05 | 北京工商大学 | Sucrose decanoate having antibacterial activity and preparation method thereof |
| CN104862101B (en) * | 2015-04-28 | 2017-12-12 | 中国热带农业科学院椰子研究所 | A kind of cocounut oil sugar ester dish washing detergent and preparation method thereof |
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