CN101450957A - Method for synthesizing maltose fatty acid ester by microwave - Google Patents
Method for synthesizing maltose fatty acid ester by microwave Download PDFInfo
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- CN101450957A CN101450957A CNA200810154741XA CN200810154741A CN101450957A CN 101450957 A CN101450957 A CN 101450957A CN A200810154741X A CNA200810154741X A CN A200810154741XA CN 200810154741 A CN200810154741 A CN 200810154741A CN 101450957 A CN101450957 A CN 101450957A
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Abstract
The invention discloses a microwave synthesis method for maltose fatty acid ester. The method is that malt syrup and fatty acid ester undergo an ester exchange reaction in the presence of an alkaline catalyst and microwaves to form the maltose fatty acid ester. Due to microwave catalysis, the method reduces reaction time, improves product color and luster, solves a problem of dehydration of the syrup raw material by the prior heating method, simplifies process, saves energy, reduces cost and avoids pollutant discharge, so the obtained maltose ester product is light in color, high in purity, safe to eat as food. The product the method can be widely used in the production and processing of food, makeup and medicines and in the cleaning industry, and so on.
Description
[technical field]: the invention belongs to the fine chemical technology field, be specifically related to a kind of novel method by maltose and lipid acid condensation prepared fatty ester of maltose.
[background technology]:
Fatty ester of maltose is the efficient emulsifying agent of a class that is formed through over-churning by maltose and lipid acid, because of maltose is to be obtained through the catalyzed by amylase hydrolysis by starch, so fatty ester of maltose is called the Dian Fentang fatty acid ester again.It belongs to the polyol ester compounds, is hydrophilic group with the free hydroxyl group in the maltose molecule, and lipid acid is oleophilic group, forms a kind of tensio-active agent with property thus.Because its raw material sources are extensive, superior performance is so fatty ester of maltose is considered to the untapped new non-ionic type of class food emulsifier.Owing to having good emulsifying, fatty acid ester is widely used in grocery trade (as bakery product, beverage, spices, coffee-mate, milk preparation, dessert and meat product etc.) cosmetic industry (as perfumed soap, cleansing milk etc.) and washing Industry.Only have both at home and abroad at present that sucrose fatty ester is a kind of is singing only angle, for fatty ester of maltose academic report is only arranged abroad, so far product-free listing still as the emulsifying agent of the oligomeric sugar esters of lipid acid.In recent years, the U.S., Canadian scientist be research by experiment again, finds that fatty ester of maltose also has the effect that suppresses tumour cell, and aspect treatment cancer, the enhance immunity power unique effect (CA1120399 is being arranged; US6525044; US5550225).In view of this, no matter fatty ester of maltose as the emulsifying agent of food, medicine, daily use chemicals product or as pharmaceutical preparation, all has very big practical potential, it synthesizes with use also will cause bigger concern.At present, the prior synthesizing method of producing the Fructus Hordei Germinatus sugar ester is to use the oil bath synthetic, the not only required long reaction time of this method, and also the color and luster of product is generally yellow or pale brown look more deeply.
Microwave also just more and more is subjected to people's attention to the promoter action of chemical reaction, utilizes the heat effect of microwave and speed that magnetoresistive effect can improve chemical reaction significantly and changes reaction mechanism, has obtained widespread use in organic synthesis.Under electromagnetic effect, the rotation of charged particle or translational speed are very fast, can promote monomer or reaction solution to be rapidly heated, and homogeneous heating, have avoided slow, the shortcoming such as inhomogeneous of being heated of traditional heating mode rate of heating.The use of microwave has been shortened the reaction times greatly, and the color and luster of product also has significant improvement.
[summary of the invention]: the present invention seeks to overcome the prior art above shortcomings, a kind of novel method of synthesizing maltose fatty acid ester by microwave is provided.
The synthetic method of fatty ester of maltose provided by the invention be with malt syrup and fatty acid ester in the presence of basic catalyst, microwave carries out transesterify, finally generates corresponding fatty ester of maltose, comprising:
1), taking by weighing 50～150 weight unit massfractions is 60%～100% malt syrup, with massfraction with respect to fatty acid ester is that 15%～35% lipid acid soap-like matter and reaction solvent mix, making it molten is homogeneous liquid, and then add the fatty acid ester of 16～150 weight unit, rock into milk sap, add massfraction with respect to fatty acid ester again and be 6%～21% catalyzer and place the microwave reactor that has agitator to react 10～30min to finish, microwave power is 150W～400W.
2), thick product is cooled to below 100 ℃, acid adjustment is pH3～5, removes that to add behind the water layer with the isopyknic massfraction of residuum be to stir suction filtration behind 15% the sodium salt solution again.
3) invade with the butanone of 1～3 times of volume and water mixed solvent, again and wash the suction filtration gains, boil off butanone then and obtain fatty ester of maltose.
1) fatty acid ester in the step can be Stearic ethyl stearate or methyl stearate, or soft-ethyl ester or soft-methyl ester, and other carbon numbers are 12～24 fatty-acid ethyl ester or methyl esters.
Fatty ester of maltose provided by the invention synthetic is that maltose (M-OH) carries out transesterify with fatty acid ester (R-COOR ') under alkaline condition, finally generates corresponding fatty ester of maltose.Reaction formula as:
In the experiment earlier malt syrup, emulsifying agent, propylene glycol adds in the reactor, makes it moltenly be homogeneous liquid, adds fatty acid esters again, rocks into milk sap, adds catalyzer again and places the microwave reactor reaction certain hour end that has agitator.Thick product is cooled to below 100 ℃, and through acid adjustment, salt water washing, the organic solvent extraction after drying obtains maltose stearate product.Whole process of preparation can be with reference to being the preparation flow figure of example with the Stearic ethyl stearate system.
The catalyzer that uses in the transesterification reaction of Fructus Hordei Germinatus sugar ester can be selected materials such as sodium hydroxide or potassium hydroxide, sodium alkoxide, potassium alcoholate, yellow soda ash, salt of wormwood, calcium oxide, magnesium oxide, the reaction system of finding to contain sodium alkoxide or potassium alcoholate in the experiment is the productive rate height not only, and excellent catalytic effect, but the cost height of sodium alkoxide or potassium alcoholate, so generally select other alkaline matters such as salt of wormwood, sodium hydroxide or potassium hydroxide for use in order to save cost in the experiment.
Thick product acid adjustment can prevent fatty ester of maltose hydrolysis under alkaline condition, available acid has citric acid and acetic acid, but a little less than the citric acid solution acidity, pH is easy to control, easy volatilization unlike acetic acid, and allow certain citric acid residual in the food applications.
Extraction agent is when selecting butanone or butanols, amylalcohol and organosilane ester solvent, and it is not fine selecting single solvent effect, selects for use butanone and water effect relatively good.
Reaction times influences the transformation efficiency of transesterification reaction and the productive rate of Fructus Hordei Germinatus sugar ester, finds in the experiment, and the prolongation with the reaction times when maltose resin acid ester productive rate begins raises, but descends on the contrary behind certain hour.Reaction times is long, and product colour is deepened.
Increase with microwave power when maltose resin acid ester begins raises, but descends to some extent on the contrary behind certain power.Reaction power is excessive, and product colour is deepened.
In this reaction system, malt syrup is water miscible, and fatty acid ester is fat-soluble, and the two is immiscible, is inhomogeneous reaction, and speed of response is slow, can add the lipid acid soap-like matter and make two-phase form homogeneous phase through emulsification, dispersion.Experiment finds that along with the increase fatty ester of maltose productive rate increase of emulsifying agent consumption, but consumption reaches at 35% o'clock, separates relatively difficulty, and therefore selecting the emulsifying agent consumption is below 35%.
Along with the prolongation in reaction times, the gamma value of glycolipid increases.
Product analysis
1. the identification experiment of product
The Fructus Hordei Germinatus sugar ester resolves into stearate and maltose with the potassium hydroxide effect in ethanolic soln, remove to go into hydrochloric acid soln behind the ethanol and the stearate effect generates stearic acid, uses extracted with diethyl ether then, and the maltose in the water is then with the check of anthrone test solution.
Take by weighing the 1g sample in the 250mL triangular flask, add the 25mL potassium hydroxide-ethanol solution, load onto reflux condensation mode, the little 1h that boils of heating in water-bath, take off and add 50mL distilled water after cold slightly, shift out behind the nearly 30mL of reconcentration, add the 10mL hydrochloric acid soln, fully vibration, add sodium-chlor and make it to become saturated solution, shake up and place separating funnel, use 30mL ether extracting twice at every turn, separate the ether layer to be measured with water layer.
Ether layer liquid adds the 2g anhydrous sodium sulfate dehydration after washing with the 20mL sodium chloride saturated solution, gets ether solution and places stink cupboard interior concentrated, and residue is white soft wafer.
Get the 2mL water layer in test tube, most ether is caught up with in heating in water-bath, and the cooling back is blue-greenish colour after tube wall adds 1mL anthrone sulphuric acid soln, prove the existence of Fructus Hordei Germinatus sugar ester.
2. the infrared analysis of product:
3. the fusing point test of product:
4 productive rates (in monoesters)=actual output/theoretical yield
m
2＝M
2×m
1×0.75/M
1
In the formula: m
2------------the quality of----glycolipid
M
2------------the molecular weight of----glycolipid
M
1------------the molecular weight of----fatty acid ester
0.75--------------the percentage quality of malt syrup
Advantage of the present invention and positively effect:
1, the present invention uses microwave heating that traditional type of heating is improved.The present invention carries out the synthetic fatty ester of maltose of transesterification reaction under the microwave catalysis effect.
2, the present invention uses microwave catalysis, not only shorten the reaction times and improved product color, but also solved the problem of traditional heating to the syrupy processed of raw material, use microwave catalysis, moisture content in the malt syrup does not influence synthetic, therefore do not need dehydration, so not only simplified technology, and saved the energy.
3, whole process of preparation and traditional synthetic method ratio, the microwave reaction mild condition, have simple to operate, raw materials cost is low, pollution-free drainage, the fatty ester of maltose product color purity height (lighter color) that therefore obtains, edible safety is good.
[description of drawings]:
Fig. 1 is to be the preparation flow figure of example with the Stearic ethyl stearate system.
[embodiment]:
Embodiment 1: preparation maltose stearate
Earlier syrup, emulsifying agent, propylene glycol adds in the reactor, makes it moltenly be homogeneous liquid, adds the stearic acid ethyl ester again, rocks into milk sap, adds catalyzer again and places the microwave reactor reaction certain hour end that has agitator.Thick product is cooled to below 100 ℃, and through acid adjustment, salt water washing, butanone extraction after drying obtains maltose stearate product.Specific operation process and step:
Taking by weighing the 20g massfraction and be 75% malt syrup makes it moltenly be homogeneous liquid in flask with after the sodium stearate of 3g (be equivalent to fatty acid ester 30%), the mixed with propylene glycol, after adding the 10g Stearic ethyl stearate again, the salt of wormwood (or yellow soda ash, calcium oxide, magnesium oxide etc.) (be equivalent to fatty acid ester 15%) that adds 1.5g, microwave power is under the 250W, reaction 20min.When being cooled to below 100 ℃, transfers about pH to 4.0 thick product with 5% lemon solution, remove after the layering add again behind the water layer with the isopyknic massfraction of residuum be that 15% sodium chloride solution stirs suction filtration after 10 to 15 minutes, continuation is washed 2 to 3 times with sodium chloride solution, fully dissolve at 53 ℃ with 3 times of volume butanone and water mixed solvent again, pour separating funnel into, standing demix is removed water layer, get supernatant liquid pressure reducing and steaming butanone, drying obtains the Fructus Hordei Germinatus sugar ester product of oyster white or white.
Embodiment 2: preparation maltose palmitate
Taking by weighing the 15g massfraction and be 85% malt syrup makes it moltenly be homogeneous liquid in flask with after 2.5g sodium palmitate (be equivalent to fatty acid ester 25%), the mixed with propylene glycol, after adding the 10g soft-ethyl ester again, the potassium hydroxide (be equivalent to fatty acid ester 15%) that adds 1.5g, microwave power is under the 200W, reaction 25min.Remaining operation is with example 1, and drying obtains the Fructus Hordei Germinatus sugar ester product of oyster white or white.
Embodiment 3: use maltitol powder to prepare the maltose stearate
Taking by weighing the 20g maltitol powder makes it moltenly be homogeneous liquid in flask with after the potassium stearate of 2g (be equivalent to fatty acid ester 20%), the mixed with propylene glycol, after adding the 10g methyl stearate again, the salt of wormwood (be equivalent to fatty acid ester 18%) that adds 1.8g, microwave power is under the 250W, reaction 15min.Remaining operation is with example 1, and drying obtains the Fructus Hordei Germinatus sugar ester product of oyster white or white.
Claims (3)
1, a kind of method of synthesizing maltose fatty acid ester by microwave, it is characterized in that this method be with malt syrup and fatty acid ester in the presence of basic catalyst, microwave carries out transesterify, finally generates corresponding fatty ester of maltose, comprising:
1), taking by weighing 50～150 weight unit massfractions is 60%～100% malt syrup, with massfraction with respect to fatty acid ester is that 15%～35% lipid acid soap-like matter and reaction solvent mix, making it molten is homogeneous liquid, and then add the fatty acid ester of 16～150 weight unit, rock into milk sap, add massfraction with respect to fatty acid ester again and be 6%～21% catalyzer and place the microwave reactor that has agitator to react 10～30min to finish, microwave power is 150W～400W;
2), thick product is cooled to below 100 ℃, acid adjustment is pH3～5, removes that to add behind the water layer with the isopyknic massfraction of residuum be to stir suction filtration behind 15% the sodium salt solution again;
3) invade with the butanone of 1～3 times of volume and water mixed solvent, again and wash the suction filtration gains, boil off butanone then and obtain fatty ester of maltose.
2, method according to claim 1 is characterized in that 1) fatty acid ester described in the step is Stearic ethyl stearate or methyl stearate, or soft-ethyl ester or soft-methyl ester, and other carbon numbers are 12～24 fatty-acid ethyl ester or methyl esters.
3, method according to claim 1 is characterized in that the 1st) catalyzer described in the step be sodium hydroxide, potassium hydroxide, sodium alkoxide, potassium alcoholate, yellow soda ash, salt of wormwood, calcium oxide or magnesian one or more.
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| CNA200810154741XA CN101450957A (en) | 2008-12-31 | 2008-12-31 | Method for synthesizing maltose fatty acid ester by microwave |
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| CNA200810154741XA CN101450957A (en) | 2008-12-31 | 2008-12-31 | Method for synthesizing maltose fatty acid ester by microwave |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101967429A (en) * | 2010-10-21 | 2011-02-09 | 中华全国供销合作总社西安生漆涂料研究所 | Lacquer wax oil sugar ester and preparation method thereof |
| CN102180814A (en) * | 2011-01-31 | 2011-09-14 | 浙江赞宇科技股份有限公司 | Microwave synthesis method of sodium fatty acyloxy isethionate |
| CN103712838A (en) * | 2013-12-31 | 2014-04-09 | 云南磷化集团有限公司 | Detection pretreatment method of anion collecting agent for collophanite flotation |
| CN108069858A (en) * | 2017-11-10 | 2018-05-25 | 浙江工业大学 | A kind of method of fatty acid soaps and silver nitrate coupling extract and separate methyl linolenate |
| CN111138322A (en) * | 2019-12-27 | 2020-05-12 | 赞宇科技集团股份有限公司 | Production process of high-quality alkyl benzene sulfonic acid |
| CN111187310A (en) * | 2020-01-17 | 2020-05-22 | 常州工学院 | Industrial preparation method of trehalose fatty acid ester |
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2008
- 2008-12-31 CN CNA200810154741XA patent/CN101450957A/en active Pending
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101967429A (en) * | 2010-10-21 | 2011-02-09 | 中华全国供销合作总社西安生漆涂料研究所 | Lacquer wax oil sugar ester and preparation method thereof |
| CN101967429B (en) * | 2010-10-21 | 2012-12-19 | 中华全国供销合作总社西安生漆涂料研究所 | Lacquer wax oil sugar ester and preparation method thereof |
| CN102180814A (en) * | 2011-01-31 | 2011-09-14 | 浙江赞宇科技股份有限公司 | Microwave synthesis method of sodium fatty acyloxy isethionate |
| CN103712838A (en) * | 2013-12-31 | 2014-04-09 | 云南磷化集团有限公司 | Detection pretreatment method of anion collecting agent for collophanite flotation |
| CN108069858A (en) * | 2017-11-10 | 2018-05-25 | 浙江工业大学 | A kind of method of fatty acid soaps and silver nitrate coupling extract and separate methyl linolenate |
| CN108069858B (en) * | 2017-11-10 | 2021-02-19 | 浙江工业大学 | Method for extracting and separating methyl linolenate by coupling fatty acid soap and silver nitrate |
| CN111138322A (en) * | 2019-12-27 | 2020-05-12 | 赞宇科技集团股份有限公司 | Production process of high-quality alkyl benzene sulfonic acid |
| CN111187310A (en) * | 2020-01-17 | 2020-05-22 | 常州工学院 | Industrial preparation method of trehalose fatty acid ester |
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Open date: 20090610 |