CN102134402A - 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 the 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, advantage such as have no side effect enjoys people to favor, it is painted that radish red pigment has been widely used in industries such as food, makeup, medicine and healthcare products.
The radish red pigment that existing method is prepared, as application number be 200910173645.4 " based on membrane separation and integration technology production take off the flavor radish red pigment the preparation method " patent, disclosed is to be raw material with the turnip with red inside, through solvent extraction, micro-filtration removal of impurities, ultrafiltration nanofiltration purifying, drying step, make the highly purified flavor radish red pigment product that takes off.The main drawback of this radish red pigment product is: because this product is a kind of mixture, except that the radish red pigment monomer, also have various ways such as dimer, the tetramer and high polymer, these molecules are the two dimensional structure structure, form with hydrophobic interaction or hydrogen bond between molecule and the molecule and combine, thereby can only be dissolved in hot water.In the time of in being applied to the food that cold working liquid foodstuff maybe need refrigerate, having radish red pigment at low temperatures and separate out, cause the liquid muddiness, have a strong impact on food quality.In addition, remain a large amount of carbohydrates, protein, amino acid, radish sulphur glycosides etc. in the existing radish red pigment product.High polymer radish red pigment poorly water-soluble, the polymer carbohydrate is dissolved in hot water, and cold water is separated out, denatured protein is water insoluble, and they all influence the solvability of radish red pigment product in cold water, and 1% cold water solution (4 ℃) is muddy and opaque.In addition, the radish red pigment product still has tangible radish sulphur glycosides peculiar smell.Because these weak points of radish red pigment product cause it not use in fields such as luxury food, makeup, sale is obstructed.
Summary of the invention
The deficiency that the objective of the invention is the radish red pigment prepared at existing method, a kind of preparation and purification process of alkylation radish red pigment are provided, have gained radish red pigment solubleness height, purity height and free from extraneous odour in cold water, production technique is simple, material makes full use of and pollute characteristics such as little.
The principle of the invention: radish red pigment is a chromocor compound.Because the flavones parent is a two dimensional structure, easily form between molecule and the molecule and arrange closely, intermolecular interaction is strong, and is by hydrophobic interaction and hydrogen bond polymerization, poorly soluble in cold water.Etherification reaction can take place under certain condition in the phenolic hydroxyl group on the radish red pigment molecule, generates the etherificate radish red pigment.Etherifying agents such as methylcarbonate, diethyl carbonate or methyl-sulfate, the etherificate that is usually used in oxy-compound, etherification starch etc. for example, therefore, with alkyl on this class etherifying agent molecule and the condensation of radish red pigment phenolic hydroxyl group, can generate the alkylation radish red pigment under proper condition.Because the adding of alkyl, the intermolecular interaction of alkylation radish red pigment significantly weakens, and is difficult to form tight arrangement, and the solvability in cold water increases.
Polymer carbohydrate, protein molecular weight in the existing radish red pigment product are huge, and radish red pigment and polymeric molecular weight thereof are less, and the ultra-filtration membrane that can adopt molecular weight cut-off to determine separates.By ultrafiltration, the filtrations such as radish red pigment, amino acid and monose that molecular weight is less, and macromolecular carbohydrate and protein promptly are trapped, thus realize separating; Compare with amino acid, monose and radish sulphur glycosides, the radish red pigment molecular weight is bigger, can adopt nanofiltration membrane to separate.By nanofiltration, than the filtrations such as amino acid, monose and radish sulphur glycosides of small molecular weight, the radish red pigment of larger molecular weight is trapped, thereby realizes separating.Therefore, by the etherification reaction of above-mentioned etherifying agent, pass through ultrafiltration, nanofiltration separation again, promptly prepare alkylation is modified, purifying free from extraneous odour radish red pigment, through concentrating and spraying drying, promptly prepare consoluet alkylation radish red pigment powder in cold water at last.
The object of the present invention is achieved like this: a kind of preparation of alkylation radish red pigment and purification process are raw material with commercially available radish red pigment, through dissolving, alkylated reaction, separation, concentrate, dry and obtain finished product.Its concrete method steps is as follows:
(1) preparation radish red pigment product solution
With commercially available radish red pigment is raw material, with mass concentration is that 5% sodium hydroxide solution is a solvent, quality (g) according to radish red pigment: mass concentration is that 5% sodium hydroxide solution volume (L) is than the ratio that is 1: 30～50, the adding mass concentration is 5% sodium hydroxide solution in radish red pigment, under agitation dissolves 20～40min.Then this mixed solution is filtered, collect filtrate and filter residue respectively.Because of filter residue is radish red pigment superpolymer and impurity, be used for production daily use chemicals series products; The radish red pigment solution that filtrate being prepared.
(2) preparation alkyl radish red pigment solution
(1) step finish after, the radish red pigment solution that (1) step was made places 20～40 ℃ thermostat water bath, 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, slowly be 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 added dropwise to diluted sodium hydroxide solution conditioned reaction liquid simultaneously is 7～8, then under 20～40 ℃ of temperature, constant temperature carried out alkylated reaction 3～6 hours, just prepared alkylation radish red pigment solution.
(3) preparation purification of alkyl radish red pigment concentrated solution
(2) step finish after, go on foot the alkylation radish red pigment solution of preparing with (2) earlier, with holding back molecule is that the ultra-filtration membrane of 10000Da carries out ultra-filtration and separation under the pressure of 0.16～0.2MPa, is that 1/8 of stoste～1/12 o'clock stops ultrafiltration until the ultrafiltration trapped fluid.Collect filter residue and filtrate respectively.For filter residue, be macromolecular carbohydrate and protein, can be used for producing feed; For filtrate, for containing the mixing solutions of alkylation radish red pigment etc., with holding back molecule is that the nanofiltration membrane of 3000Da is carried out nanofiltration separation under 0.16～0.2MPa pressure, when the nanofiltration trapped fluid be stoste 1/8～1/12 the time, the dilute with water trapped fluid is to the stoste volume, carry out nanofiltration separation once more, 2～6 times so repeatedly, collect trapped fluid and filtered solution respectively.For filtered solution, because of containing amino acid, monose, radish sulphur glycosides, carbonate, methyl alcohol, ethanol and unreacted methylcarbonate or diethyl carbonate or methyl-sulfate etherifying agent, discharge through neutralization, bio-oxidation back up to standard; To trapped fluid, be the alkylation radish red pigment solution of purifying, be positioned in the vacuum concentrator, be to carry out vacuum concentration 60～100min under 83～87KPa condition in vacuum tightness, just prepare purification of alkyl radish red pigment concentrated solution.
(4) preparation purification of alkyl radish red pigment dry powder
(3) step finish after, go on foot the purification of alkyl radish red pigment concentrated solution of preparing with (3), be positioned in the spray-dryer, in inlet temperature is that 100～130 ℃, temperature out are to carry out spraying drying under 80～85 ℃ of conditions, just prepare purity and be 80.4%～87.3% alkylation radish red pigment power-product, total recovery rate of product is 89.4%～95.8%, 1% cold water solution (4 ℃) clear.
After the present invention adopts technique scheme, mainly contain following effect:
(1) production process of the present invention adopts methylcarbonate or diethyl carbonate or methyl-sulfate etherifying agent that radish red pigment is carried out alkylation modification, weaken hydrophobic grouping and interacted and hydrogen bond action, significantly improved the solubleness of radish red pigment in cold water.Therefore the product that adopts the inventive method to prepare can be widely used in the industries such as food, medicine, healthcare products, makeup, dyestuff, has enlarged the 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 the purity that makes radish red pigment is up to 87.3%, and removed the radish red pigment peculiar smell, from and promoted product quality.
(3) the present invention adopts chemical method with the radish red pigment alkylation, and total recovery rate of alkylation radish red pigment is up to 95.8%.
(4) the inventive method technology is simple, only adopts simple process such as millipore filtration, chemically modified, membrane sepn, spraying drying, and overall save energy, production cost are low.But therefore technology widespread use of the present invention and radish red pigment deep processing improves the radish red pigment value added.
Advantages such as (5) technology of the present invention has the reaction conditions gentleness, and is free from environmental pollution, and the 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 specify the present invention.
Embodiment 1
A kind of preparation of alkylation radish red pigment and purification process, concrete steps are as follows:
(1) preparation radish red pigment product solution
With commercially available radish red pigment is raw material, with mass concentration is that 5% sodium hydroxide solution is a solvent, quality (g) according to radish red pigment: mass concentration is that the ratio of 5% sodium hydroxide solution volume (L) is 1: 30 a ratio, the adding mass concentration is 5% sodium hydroxide solution in radish red pigment, under agitation dissolves 20min.Then this mixed solution is filtered, collect filtrate and filter residue respectively.Because of filter residue is radish red pigment superpolymer and impurity, can be used for the daily use chemicals series products; The radish red pigment solution that filtrate being prepared.
(2) preparation alkyl radish red pigment solution
(1) step finish after, the radish red pigment solution that makes in (1) step is placed thermostat water bath, under 20 ℃ of temperature, carry out water bath with thermostatic control, and in radish red pigment: the mass ratio of liquid carbonic acid dimethyl ester is 1: 1 a ratio, under agitation condition, in 20min, slowly be added dropwise to the liquid carbonic acid dimethyl ester and carry out alkylated reaction, the pH value that is added dropwise to diluted sodium hydroxide solution conditioned reaction liquid simultaneously is 7, then under 20 ℃ of temperature, constant temperature carried out alkylated reaction 3 hours, just prepared alkylation radish red pigment solution.
(3) preparation purification of alkyl radish red pigment concentrated solution
After (2) step finished, the first alkylation radish red pigment solution that (2) step was prepared was that the ultra-filtration membrane of 10000Da carries out ultra-filtration and separation under the pressure of 0.16MPa with holding back molecule, stops ultrafiltration when the ultrafiltration trapped fluid is stoste 1/8.Collect filter residue and filtrate respectively.For filter residue, be macromolecular carbohydrate and protein, can be used for producing feed; For filtrate, for containing the mixing solutions of alkylation radish red pigment etc., with holding back molecule is that the nanofiltration membrane of 3000Da is carried out nanofiltration separation under 0.16MPa pressure, when the nanofiltration trapped fluid be stoste 1/8 the time, the dilute with water trapped fluid is to the primary liquid volume, carry out nanofiltration separation once more, 2 times so repeatedly, collect trapped fluid and filtered solution respectively.To filtered solution, because of containing amino acid, monose, radish sulphur glycosides, carbonate, methyl alcohol and unreacted methylcarbonate, discharge through neutralization, bio-oxidation back up to standard.To trapped fluid, be the alkylation radish red pigment solution of purifying, be positioned in the vacuum concentrator, be to carry out vacuum concentration 60min under the 83KPa condition in vacuum tightness, just prepare purification of alkyl radish red pigment concentrated solution.
(4) preparation purification of alkyl radish red pigment dry powder
(3) step finish after, go on foot the purification of alkyl radish red pigment concentrated solution of preparing with (3), be positioned in the spray-dryer, in inlet temperature is that 100 ℃, temperature out are to carry out spraying drying under 80 ℃ of conditions, just prepare purity and be 80.4% alkylation radish red pigment power-product, total recovery rate of product is 89.4%, 1% cold water solution (4 ℃) clear.
Embodiment 2
A kind of preparation of alkylation radish red pigment and 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 mass ratio of liquid carbonic acid diethyl ester is 1: 2 a ratio, and the dropping time 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, the ultrafiltration trapped fluid is 1/10 of a stoste, nanofiltration pressure is 0.18MPa, the nanofiltration trapped fluid is 1/10 of a stoste, nanofiltration 4 times repeatedly, and the nanofiltration filtered solution contains amino acid, monose, radish sulphur glycosides, carbonate, methyl alcohol and unreacted diethyl carbonate, vacuum concentration vacuum tightness is 85KPa, and the vacuum concentration time is 80min.
In (4) step, the spraying drying inlet temperature is 110 ℃, and temperature out is 83 ℃, and purity is 87.3%, and total recovery rate is 95.8%.
Embodiment 3
A kind of preparation of alkylation radish red pigment and 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 mass ratio of fluid sulphuric acid dimethyl ester is 1: 3 a ratio, and the dropping time 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, the ultrafiltration trapped fluid is 1/12 of a stoste, nanofiltration pressure is 0.2MPa, the nanofiltration trapped fluid is 1/12 of a stoste, nanofiltration 6 times repeatedly, and the nanofiltration filtered solution contains amino acid, monose, radish sulphur glycosides, carbonate, methyl alcohol and unreacted methyl-sulfate, vacuum concentration vacuum tightness is 87KPa, and the vacuum concentration time is 100min.
In (4) step, the spraying drying inlet temperature 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 an alkylation radish red pigment and purification process is characterized in that concrete steps are as follows:
(1) preparation radish red pigment product solution
With commercially available radish red pigment is raw material, with mass concentration is that 5% sodium hydroxide solution is a solvent, quality according to radish red pigment: mass concentration is that the ratio of 5% sodium hydroxide solution volume is the ratio of 1g: 30～50L, the adding mass concentration is 5% sodium hydroxide solution in radish red pigment, under agitation dissolve 20～40min, then this mixed solution is filtered, collect filtrate and filter residue respectively;
(2) preparation alkyl radish red pigment solution
(1) step finish after, go on foot the radish red pigment solution that makes with (1), place 20～40 ℃ thermostat water bath, 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 added dropwise to diluted sodium hydroxide solution conditioned reaction liquid simultaneously is 7～8, under 20～40 ℃ of temperature, constant temperature carried out alkylated reaction 3～6 hours then;
(3) preparation purification of alkyl radish red pigment concentrated solution
(2) step finish after, go on foot the alkylation radish red pigment solution of preparing with (2) earlier, with holding back molecule is that the ultra-filtration membrane of 10000Da carries out ultra-filtration and separation under the pressure of 0.16～0.2MPa, till the ultrafiltration trapped fluid is 1/8 of stoste～1/12 o'clock, collects filter residue and filtrate respectively; Is that the nanofiltration membrane of 3000Da is carried out nanofiltration separation for filtrate under 0.16～0.2MPa pressure with holding back molecule, when the nanofiltration trapped fluid be stoste 1/8～1/12 the time, with the distilled water diluting trapped fluid to the stoste volume, carry out nanofiltration separation once more, 2～6 times so repeatedly, collecting trapped fluid and filtered solution respectively, trapped fluid is positioned in the vacuum concentrator, is to carry out vacuum concentration 60～100min under 83～87KPa condition in vacuum tightness;
(4) preparation purification of alkyl radish red pigment dry powder
(3) step with (3) the purification of alkyl radish red pigment concentrated solution prepared of step, was positioned in the spray-dryer after finishing, and was that 100～130 ℃, temperature out are to carry out spraying drying under 80～85 ℃ of conditions in inlet temperature.
2. according to the preparation and the purification process of the described a kind of alkylation radish red pigment of claim 1, it is characterized in that:
In (1) step, the quality of radish red pigment: mass concentration is that the ratio of 5% sodium hydroxide solution volume is the ratio of 1g: 30L, and dissolution time is 20min;
In (2) step, bath temperature is 20 ℃, radish red pigment: the mass ratio of liquid carbonic acid dimethyl ester is 1: 1 a ratio, and the dropping time 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 the ultrafiltration trapped fluid is 1/8 of a stoste, and nanofiltration pressure is 0.16MPa, and the nanofiltration trapped fluid is 1/8 of a stoste, nanofiltration 2 times repeatedly, and vacuum concentration vacuum tightness is 83KPa, the vacuum concentration time is 60min;
In (4) step, the spraying drying inlet temperature is 100 ℃, and temperature out is 80 ℃.
3. according to the preparation and the purification process of the described a kind of alkylation radish red pigment of claim 1, it is characterized in that:
In (1) step, the quality of radish red pigment: mass concentration is that 5% sodium hydroxide solution volume ratio is the ratio of 1g: 40L, and dissolution time is 30min;
In (2) step, bath temperature is 30 ℃, radish red pigment: the mass ratio of liquid carbonic acid diethyl ester is 1: 2 a ratio, and the dropping time 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 the ultrafiltration trapped fluid is 1/10 of a stoste, and nanofiltration pressure is 0.18MPa, and the nanofiltration trapped fluid is 1/10 of a stoste, nanofiltration 4 times repeatedly, and vacuum concentration vacuum tightness is 85KPa, the vacuum concentration time is 80min;
In (4) step, the spraying drying inlet temperature is 110 ℃, and temperature out is 83 ℃.
4. according to the preparation and the purification process of the described a kind of alkylation radish red pigment of claim 1, it is characterized in that:
In (1) step, the quality of radish red pigment: mass concentration is that 5% sodium hydroxide solution volume ratio is the ratio of 1g: 50L, and dissolution time is 40min;
In (2) step, bath temperature is 40 ℃, radish red pigment: the mass ratio of fluid sulphuric acid dimethyl ester is 1: 3 a ratio, and the dropping time 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 the ultrafiltration trapped fluid is 1/12 of a stoste, and nanofiltration pressure is 0.2MPa, and the nanofiltration trapped fluid is 1/12 of a stoste, nanofiltration 6 times repeatedly, and vacuum concentration vacuum tightness is 87KPa, the vacuum concentration time is 100min;
In (4) step, the spraying drying inlet temperature is 130 ℃, and temperature out is 85 ℃.
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| CN201110000822.6A CN102134402B (en) | 2011-01-04 | 2011-01-04 | Method for preparing and purifying alkylated radish red pigment |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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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