CN102134402B - Method for preparing and purifying alkylated radish red pigment - Google Patents
Method for preparing and purifying alkylated radish red pigment Download PDFInfo
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Abstract
The invention relates to a method for preparing and purifying alkylated radish red pigment, belonging to the technical field of preparation methods of natural red pigments in plants. The method comprises the following steps: dissolving market-sold radish red pigment which is used as a raw material, carrying out alkylation reaction, separating, concentrating and drying to obtain the product. The invention has the characteristics of simple technique, no waste discharge, energy saving, low production cost, high product purity (up to 87.3%), high yield (up to 95.8%), and the like, and enhances the solubility of the product in cold water. The invention can be widely used for modifying flavonoids (such as hesperidin and the like), and is especially suitable for purifying radish red pigment. The product prepared by the method provided by the invention can be widely used in the industries of food, medicine, health products, cosmetics, dye and the like.
Description
Technical field
The invention belongs to natural red colouring matter preparation method technical field in plant, be specifically related to the purification process of radish red pigment.
Background technology
Radish red pigment is a kind of natural food colour, with its natural color and luster, safely, the advantage such as have no side effect enjoys people to favor, it is painted that radish red pigment has been widely used in the industries such as food, makeup, medicine and healthcare products.
The radish red pigment that existing method is prepared, as application number " producing the preparation method of de-taste radish red pigment based on the membrane separation and integration technology " patent that is 200910173645.4, disclosed is to take turnip with red inside as raw material, through solvent extraction, micro-filtration removal of impurities, ultrafiltration nanofiltration purifying, drying step, make highly purified de-taste radish red pigment product.The main drawback of this radish red pigment product is: because this product is a kind of mixture, except radish red pigment monomer, also have the various ways such as dimer, the tetramer and high polymer, these molecules are two dimensional structure structure, between molecule and molecule, with hydrophobic interaction or hydrogen bond, form combination, thereby can only be dissolved in hot water.In the time of in the food that is applied to cold working liquid foodstuff and maybe needs refrigeration, have at low temperatures radish red pigment and separate out, cause liquid muddy, have a strong impact on food quality.In addition, in existing radish red pigment product, remain a large amount of carbohydrates, protein, amino acid, glucorphanin etc.High polymer radish red pigment poorly water-soluble, polymer carbohydrate is dissolved in hot water, and cold water is separated out, denatured protein is water insoluble, and they all affect the solvability of radish red pigment product in cold water, and 1% cold water solution (4 ℃) is muddy and opaque.In addition, radish red pigment product still has obvious glucorphanin peculiar smell.Due to these weak points of radish red pigment product, cause it not apply in fields such as luxury food, makeup, sale is obstructed.
Summary of the invention
The deficiency that the object of the invention is the radish red pigment prepared for existing method, a kind of preparation and purification process of alkylated radish red pigment are provided, have that gained radish red pigment solubleness in cold water is high, purity is high and free from extraneous odour, production technique is simple, material makes full use of and pollute the features such as little.
The principle of the invention: radish red pigment is chromocor compound.Because flavones parent is two dimensional structure, between molecule and molecule, easily form and arrange closely, intermolecular interaction is strong, by hydrophobic interaction and hydrogen bond polymerization, poorly soluble in cold water.Can there is etherification reaction under certain condition in the phenolic hydroxyl group on radish red pigment molecule, generate etherificate radish red pigment.The etherifying agents such as methylcarbonate, diethyl carbonate or methyl-sulfate, the etherificate that is usually used in oxy-compound, such as etherification starch etc., therefore, by the alkyl on this class etherifying agent molecule and the condensation of radish red pigment phenolic hydroxyl group, can generate alkylated radish red pigment under proper condition.Due to adding of alkyl, the intermolecular interaction of alkylated radish red pigment significantly weakens, and is difficult to form close-packed arrays, and the solvability in cold water increases.
Polymer carbohydrate, protein molecular weight in existing radish red pigment product are huge, and radish red pigment and polymeric molecular weight thereof can adopt the definite ultra-filtration membrane of molecular weight cut-off to carry out separation.By ultrafiltration, the filtrations such as the radish red pigment of molecular weight, amino acid and monose, and macromolecular carbohydrate and protein are trapped, thus realize separated; Compare with amino acid, monose and glucorphanin, radish red pigment molecular weight is larger, can adopt nanofiltration membrane to carry out separation.By nanofiltration, compared with filtrations such as the amino acid of small molecules amount, monose and glucorphanins, the radish red pigment of larger molecular weight is trapped, thereby realizes separated.Therefore, by the etherification reaction of above-mentioned etherifying agent, then pass through ultrafiltration, nanofiltration separation, prepare alkylation is modified, purifying free from extraneous odour radish red pigment, finally by crossing to concentrate and spray, be dried, prepare consoluet alkylated radish red pigment powder in cold water.
The object of the present invention is achieved like this: a kind of preparation of alkylated radish red pigment and purification process, take commercially available radish red pigment as raw material, through dissolving, alkylated reaction, separation, concentrated, dry and obtain finished product.Its concrete method steps is as follows:
(1) prepare radish red pigment product solution
Take commercially available radish red pigment as raw material, the sodium hydroxide solution that is 5% by mass concentration is solvent, according to the quality of radish red pigment (g): the sodium hydroxide solution volume (L) that mass concentration is 5% is than the ratio that is 1: 30～50, in radish red pigment, adding mass concentration is 5% sodium hydroxide solution, under agitation dissolves 20～40min.Then this mixed solution is filtered, collect respectively filtrate and filter residue.Because filter residue is radish red pigment superpolymer and impurity, for the production of daily use chemicals series products; The radish red pigment solution that filtrate being prepared.
(2) prepare alkyl radish red pigment solution
After (1) step completes, the radish red pigment solution that (1) step is made is placed in the thermostat water bath of 20～40 ℃, in radish red pigment: the mass ratio of liquid carbonic acid dimethyl ester or diethyl carbonate or methyl-sulfate etherifying agent is 1: 1～3 ratio, under agitation condition, in 20～40min, be slowly added dropwise to liquid carbonic acid dimethyl ester or diethyl carbonate or methyl-sulfate etherifying agent and carry out alkylated reaction, the pH value that is simultaneously added dropwise to diluted sodium hydroxide solution adjusting reaction solution is 7～8, then at 20～40 ℃ of temperature, constant temperature carries out alkylated reaction 3～6 hours, just prepare alkylated radish red pigment solution.
(3) prepare purification of alkyl radish red pigment concentrated solution
After (2) step completes, the alkylated radish red pigment solution of first (2) step being prepared, with holding back molecule, be that the ultra-filtration membrane of 10000Da carries out ultra-filtration and separation under the pressure of 0.16～0.2MPa, until ultrafiltration trapped fluid is stoste, stop ultrafiltration at 1/8～1/12 o'clock.Collect respectively filter residue and filtrate.For filter residue, be macromolecular carbohydrate and protein, can be used for producing feed; For filtrate, for the mixing solutions containing alkylated radish red pigment etc., with holding back molecule, be that the nanofiltration membrane of 3000Da is carried out nanofiltration separation under 0.16～0.2MPa pressure, when nanofiltration trapped fluid is stoste 1/8～1/12 time, dilute with water trapped fluid is to stoste volume, again carry out nanofiltration separation, 2～6 times so repeatedly, collect respectively trapped fluid and filtered solution.For filtered solution, because containing amino acid, monose, glucorphanin, carbonate, methyl alcohol, ethanol and unreacted methylcarbonate or diethyl carbonate or methyl-sulfate etherifying agent, through neutralization, bio-oxidation up to standard after discharge; To trapped fluid, be the alkylated radish red pigment solution of purifying, be positioned in vacuum concentrator, in vacuum tightness, be under 83～87KPa condition, to carry out vacuum concentration 60～100min, just prepare purification of alkyl radish red pigment concentrated solution.
(4) prepare purification of alkyl radish red pigment dry powder
After (3) step completes, the purification of alkyl radish red pigment concentrated solution that (3) step is prepared, be positioned in spray-dryer, inlet temperature be 100～130 ℃, temperature out be under 80～85 ℃ of conditions, spray dry, just prepare purity and be 80.4%～87.3% alkylated radish red pigment power-product, total recovery rate of product is 89.4%～95.8%, 1% cold water solution (4 ℃) clear.
The present invention adopts after technique scheme, mainly contains following effect:
(1) production process of the present invention adopts methylcarbonate or diethyl carbonate or methyl-sulfate etherifying agent to carry out alkylation modification to radish red pigment, weaken hydrophobic grouping and interacted and hydrogen bond action, significantly improved the solubleness of radish red pigment in cold water.Therefore adopt the product that the inventive method is prepared can be widely used in the industries such as food, medicine, healthcare products, makeup, dyestuff, expanded range of application and the field of radish red pigment.
(2) production process of the present invention adopts ultra-filtration membrane to hold back protein, carbohydrate macromole and radish red pigment superpolymer, adopts nanofiltration membrane to see through small-molecule substance.Thereby make the purity of radish red pigment up to 87.3%, and removed radish red pigment peculiar smell, from and promoted product quality.
(3) the present invention adopts chemical method by radish red pigment alkylation, and total recovery rate of alkylated radish red pigment is up to 95.8%.
(4) the inventive method technique is simple, only adopts the simple process such as millipore filtration, chemically modified, membrane sepn, spraying be dry, and overall save energy, production cost are low.Therefore technique of the present invention can widespread use and radish red pigment deep processing, raising radish red pigment value added.
(5) advantages such as technique of the present invention has reaction conditions gentleness, free from environmental pollution, and material utilization is abundant, and production cost is low.
The present invention can be widely used in the modification of flavonoid compound etc., be specially adapted to the deep processing of radish red pigment, can improve the quality of radish red pigment, the product that adopts the present invention to prepare can be widely used in the industries such as food, medicine, healthcare products, makeup and dyestuff.
Embodiment
Below in conjunction with embodiment, further illustrate the present invention.
Embodiment 1
The preparation of alkylated radish red pigment and a purification process, concrete steps are as follows:
(1) prepare radish red pigment product solution
Take commercially available radish red pigment as raw material, the sodium hydroxide solution that is 5% by mass concentration is solvent, according to the quality of radish red pigment (g): the ratio that the ratio of the sodium hydroxide solution volume (L) that mass concentration is 5% is 1: 30, in radish red pigment, adding mass concentration is 5% sodium hydroxide solution, under agitation dissolves 20min.Then this mixed solution is filtered, collect respectively filtrate and filter residue.Because filter residue is radish red pigment superpolymer and impurity, can be for daily use chemicals series products; The radish red pigment solution that filtrate being prepared.
(2) prepare alkyl radish red pigment solution
After (1) step completes, the radish red pigment solution making in (1) step is placed in to thermostat water bath, at 20 ℃ of temperature, carry out water bath with thermostatic control, and in radish red pigment: the ratio that the mass ratio of liquid carbonic acid dimethyl ester is 1: 1, under agitation condition, in 20min, be slowly added dropwise to liquid carbonic acid dimethyl ester and carry out alkylated reaction, the pH value that is simultaneously added dropwise to diluted sodium hydroxide solution adjusting reaction solution is 7, then at 20 ℃ of temperature, constant temperature carries out alkylated reaction 3 hours, just prepares alkylated radish red pigment solution.
(3) prepare purification of alkyl radish red pigment concentrated solution
After (2) step completes, the alkylated radish red pigment solution of first (2) step being prepared, is that the ultra-filtration membrane of 10000Da carries out ultra-filtration and separation under the pressure of 0.16MPa with holding back molecule, until ultrafiltration trapped fluid stops ultrafiltration while being stoste 1/8.Collect respectively filter residue and filtrate.For filter residue, be macromolecular carbohydrate and protein, can be used for producing feed; For filtrate, for the mixing solutions containing alkylated radish red pigment etc., with holding back molecule, be that the nanofiltration membrane of 3000Da is carried out nanofiltration separation under 0.16MPa pressure, when nanofiltration trapped fluid is stoste 1/8 time, dilute with water trapped fluid is to primary liquid volume, again carry out nanofiltration separation, 2 times so repeatedly, collect respectively trapped fluid and filtered solution.To filtered solution, because containing amino acid, monose, glucorphanin, carbonate, methyl alcohol and unreacted methylcarbonate, through neutralization, bio-oxidation up to standard after discharge.To trapped fluid, be the alkylated radish red pigment solution of purifying, be positioned in vacuum concentrator, in vacuum tightness, be under 83KPa condition, to carry out vacuum concentration 60min, just prepare purification of alkyl radish red pigment concentrated solution.
(4) prepare purification of alkyl radish red pigment dry powder
After (3) step completes, the purification of alkyl radish red pigment concentrated solution that (3) step is prepared, be positioned in spray-dryer, inlet temperature be 100 ℃, temperature out be under 80 ℃ of conditions, spray dry, just prepare purity and be 80.4% alkylated radish red pigment power-product, the cold water solution that total recovery rate of product is 89.4%, 1% (4 ℃) clear.
Embodiment 2
The preparation of alkylated radish red pigment and a purification process, with embodiment 1, wherein:
In (1) step, the quality of radish red pigment (g): the sodium hydroxide solution volume (L) of 5% concentration is than the ratio that is 1: 40, and dissolution time is 30min.
In (2) step, bath temperature is 30 ℃, radish red pigment: the ratio that the mass ratio of liquid carbonic acid diethyl ester is 1: 2, and time for adding is 30min, and reaction solution pH is 7.5, and temperature of reaction is 30 ℃, and the reaction times is 4.5 hours.
In (3) step, ultrafiltration pressure is 0.18MPa, ultrafiltration trapped fluid is 1/10 of stoste, nanofiltration pressure is 0.18MPa, nanofiltration trapped fluid is 1/10 of stoste, nanofiltration 4 times repeatedly, and nanofiltration filtered solution contains amino acid, monose, glucorphanin, carbonate, methyl alcohol and unreacted diethyl carbonate, vacuum concentration vacuum tightness is 85KPa, and the vacuum concentration time is 80min.
In (4) step, the dry inlet temperature of spraying is 110 ℃, and temperature out is 83 ℃, and purity is 87.3%, and total recovery rate is 95.8%.
Embodiment 3
The preparation of alkylated radish red pigment and a purification process, with embodiment 1, wherein:
In (1) step, the quality of radish red pigment (g): the sodium hydroxide solution volume (L) of 5% concentration is than the ratio that is 1: 50, and dissolution time is 40min.
In (2) step, bath temperature is 40 ℃, radish red pigment: the ratio that the mass ratio of fluid sulphuric acid dimethyl ester is 1: 3, and time for adding is 40min, and reaction solution pH is 8, and temperature of reaction is 40 ℃, and the reaction times is 6 hours.
In (3) step, ultrafiltration pressure is 0.2MPa, ultrafiltration trapped fluid is 1/12 of stoste, nanofiltration pressure is 0.2MPa, nanofiltration trapped fluid is 1/12 of stoste, nanofiltration 6 times repeatedly, and nanofiltration filtered solution contains amino acid, monose, glucorphanin, carbonate, methyl alcohol and unreacted methyl-sulfate, vacuum concentration vacuum tightness is 87KPa, and the vacuum concentration time is 100min.
In (4) step, the dry inlet temperature of spraying is 130 ℃, and temperature out is 85 ℃, and purity is 84.7%, and total recovery rate is 92.6%.
Claims (4)
1. the preparation of alkylated radish red pigment and a purification process, is characterized in that concrete steps are as follows:
(1) prepare radish red pigment product solution
Take commercially available radish red pigment as raw material, the sodium hydroxide solution that is 5% by mass concentration is solvent, according to the quality of radish red pigment: the ratio of the sodium hydroxide solution volume that mass concentration is 5% is the ratio of 1g: 30～50L, in radish red pigment, adding mass concentration is 5% sodium hydroxide solution, under agitation dissolve 20～40min, then this mixed solution is filtered, collect respectively filtrate and filter residue;
(2) prepare alkyl radish red pigment solution
After (1) step completes, the radish red pigment solution that (1) step is made, be placed in the thermostat water bath of 20～40 ℃, in radish red pigment: the mass ratio of liquid carbonic acid dimethyl ester or diethyl carbonate or methyl-sulfate etherifying agent is 1: 1～3 ratio, under agitation condition, in 20～40min, be added dropwise to liquid carbonic acid dimethyl ester or diethyl carbonate or methyl-sulfate etherifying agent, the pH value that is simultaneously added dropwise to diluted sodium hydroxide solution adjusting reaction solution is 7～8, then at 20～40 ℃ of temperature, constant temperature carries out alkylated reaction 3～6 hours;
(3) prepare purification of alkyl radish red pigment concentrated solution
After (2) step completes, the alkylated radish red pigment solution of first (2) step being prepared, with holding back molecule, be that the ultra-filtration membrane of 10000Da carries out ultra-filtration and separation under the pressure of 0.16～0.2MPa, until ultrafiltration trapped fluid is stoste, collect respectively filter residue and filtrate at 1/8～1/12 o'clock; For filtrate, with holding back molecule, be that the nanofiltration membrane of 3000Da is carried out nanofiltration separation under 0.16～0.2MPa pressure, when nanofiltration trapped fluid is stoste 1/8～1/12 time, with distilled water diluting trapped fluid to stoste volume, again carry out nanofiltration separation, 2～6 times so repeatedly, collecting respectively trapped fluid and filtered solution, trapped fluid is positioned in vacuum concentrator, is under 83～87KPa condition, to carry out vacuum concentration 60～100min in vacuum tightness;
(4) prepare purification of alkyl radish red pigment dry powder
After (3) step completes, the purification of alkyl radish red pigment concentrated solution that (3) step is prepared, is positioned in spray-dryer, inlet temperature be 100～130 ℃, temperature out be under 80～85 ℃ of conditions, spray dry.
2. according to the preparation of a kind of alkylated radish red pigment claimed in claim 1 and purification process, it is characterized in that:
In (1) step, the quality of radish red pigment: the ratio of the sodium hydroxide solution volume that mass concentration is 5% is the ratio of 1g: 30L, dissolution time is 20min;
In (2) step, bath temperature is 20 ℃, radish red pigment: the ratio that the mass ratio of liquid carbonic acid dimethyl ester is 1: 1, and time for adding is 20min, and reaction solution pH is 7, and temperature of reaction is 20 ℃, and the reaction times is 3 hours;
In (3) step, ultrafiltration pressure is 0.16MPa, and ultrafiltration trapped fluid is stoste 1/8, and nanofiltration pressure is 0.16MPa, and nanofiltration trapped fluid is stoste 1/8, nanofiltration 2 times repeatedly, and vacuum concentration vacuum tightness is 83KPa, the vacuum concentration time is 60min;
In (4) step, the dry inlet temperature of spraying is 100 ℃, and temperature out is 80 ℃.
3. according to the preparation of a kind of alkylated radish red pigment claimed in claim 1 and purification process, it is characterized in that:
In (1) step, the quality of radish red pigment: the sodium hydroxide solution volume ratio that mass concentration is 5% is the ratio of 1g: 40L, dissolution time is 30min;
In (2) step, bath temperature is 30 ℃, radish red pigment: the ratio that the mass ratio of liquid carbonic acid diethyl ester is 1: 2, and time for adding is 30min, and reaction solution pH is 7.5, and temperature of reaction is 30 ℃, and the reaction times is 4.5 hours;
In (3) step, ultrafiltration pressure is 0.18MPa, and ultrafiltration trapped fluid is stoste 1/10, and nanofiltration pressure is 0.18MPa, and nanofiltration trapped fluid is stoste 1/10, nanofiltration 4 times repeatedly, and vacuum concentration vacuum tightness is 85KPa, the vacuum concentration time is 80min;
In (4) step, the dry inlet temperature of spraying is 110 ℃, and temperature out is 83 ℃.
4. according to the preparation of a kind of alkylated radish red pigment claimed in claim 1 and purification process, it is characterized in that:
In (1) step, the quality of radish red pigment: the sodium hydroxide solution volume ratio that mass concentration is 5% is the ratio of 1g: 50L, dissolution time is 40min;
In (2) step, bath temperature is 40 ℃, radish red pigment: the ratio that the mass ratio of fluid sulphuric acid dimethyl ester is 1: 3, and time for adding is 40min, and reaction solution pH is 8, and temperature of reaction is 40 ℃, and the reaction times is 6 hours;
In (3) step, ultrafiltration pressure is 0.2MPa, and ultrafiltration trapped fluid is stoste 1/12, and nanofiltration pressure is 0.2MPa, and nanofiltration trapped fluid is stoste 1/12, nanofiltration 6 times repeatedly, and vacuum concentration vacuum tightness is 87KPa, the vacuum concentration time is 100min;
In (4) step, the dry inlet temperature of spraying is 130 ℃, and temperature out is 85 ℃.
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| CN105504865A (en) * | 2015-12-15 | 2016-04-20 | 重庆大学 | Preparation and purification method of esterification modified radish red pigments |
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