CN105504865A - Preparation and purification method of esterification modified radish red pigments - Google Patents
Preparation and purification method of esterification modified radish red pigments Download PDFInfo
- Publication number
- CN105504865A CN105504865A CN201510976867.5A CN201510976867A CN105504865A CN 105504865 A CN105504865 A CN 105504865A CN 201510976867 A CN201510976867 A CN 201510976867A CN 105504865 A CN105504865 A CN 105504865A
- Authority
- CN
- China
- Prior art keywords
- red pigment
- radish red
- esterification
- pressure
- radish
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B61/00—Dyes of natural origin prepared from natural sources, e.g. vegetable sources
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0096—Purification; Precipitation; Filtration
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cosmetics (AREA)
Abstract
The invention provides a preparation and purification method of esterification modified radish red pigments and relates to the preparation and purification method of the radish red pigments. According to the method, the radish red pigments sold on the market are taken as raw materials, an acyl chloride reaction liquid for esterification modified radish red pigments is prepared, then an esterification modified radish red pigment solution is prepared, an esterification modified radish red pigment concentrated solution is prepared through purification and concentration, and esterification modified radish red pigment products are prepared through freezing drying. The method mainly has the characteristics that the technological process is short, operation is simple, convenient and safe, energy is saved, no harmful substances are discharged and the like. The products prepared with the method mainly have the characteristics of good stability in the aspects of temperatures, pH, light and the like. The method can be widely applied to preparation and purification of the esterification modified radish red pigment products. The esterification modified radish red pigment products prepared with the method can be widely applied to fields such as food, dye, health-care products, cosmetics and the like, are especially applicable to the fields such as high-temperature-resistant and illumination-resistant high-grade food in different pH ranges, high-grade cosmetics and the like.
Description
Technical field
The invention belongs to natural red colouring matter preparation method technical field in plant, be specifically related to preparation and the purification process of radish red pigment.
Background technology
Turnip with red inside is also known as rouge radish, and the ground such as Fuling, WuLong in Chongqing is the main place of production of turnip with red inside.The radish red pigment extracted from turnip with red inside is a kind of natural pigment, bright in colour, have safe and reliable, have no side effect, the multiple biological activity such as tone is natural, anti-oxidant, food, makeup, beverage, healthcare products, medicine and other fields can be widely used in.The basic structure of radish red pigment belongs to anthocyanin class natural pigment; it is the glucoside derivative of pelargonin; for two acyl group structures of pelargonin-3-Chinese scholartree disaccharides-5-glucose; radish red pigment is soluble in hot water, methyl alcohol, ethanol polar solvent, is insoluble to the non-polar solvents such as acetone, normal hexane, ethyl acetate.Because anthocyanogen character is unstable, light, pH, temperature and metal ion etc. all can cause its change of properties, significantly limit the application of radish red pigment in the field such as luxury food, makeup and popularization.Therefore radish red pigment is improved to the stability of light, pH, temperature etc., for its application in the industry with promote significant.Reacted by radish red pigment and esterifying organic acid, radish red pigment molecular structure basis is introduced different functional group formed and sterically hinderedly increase the stability of radish red pigment to light, pH, temperature etc., simultaneously, the group introduced is polar group, too increase the solvability that radish red pigment product is modified in esterification, expand the application in industries such as food.
Existing radish red pigment preparation method, publication No. as announcement on 07 16th, 2014 is " a kind of preparation method of radish red pigment " patent of CN103923483A, disclosed method is: take turnip with red inside as raw material, first carry out raw material pre-treatment, the acid tap water squeezing of rear employing or lixiviate, then add oxidizing flocculant and carry out oxidizing, flocculating process, then carry out polymeric adsorbent column chromatography, finally concentrated, drying treatment obtains radish red pigment product.The main drawback of the radish red pigment product obtained by the method is: (1) temperature is large on the impact of radish red pigment stability, and radish red pigment is more stable below 50 DEG C, but light absorption value declines very fast more than 50 DEG C; (2) pH is large on the impact of radish red pigment stability, and radish red pigment color and maximum absorption wavelength have very big-difference under different PH; (3) impact of light on radish red pigment stability is large, although under coloured light irradiation is fallen apart in indoor, radish red pigment is more stable, and tone does not change, and pigment rate of loss is less, under outdoor natural light irradiates, irradiation time is in 2 days, and the rate of loss of radish red pigment is less, but along with time continuation increase, irradiate after 5 days, the rate of loss of radish red pigment reaches 50%.The radish red pigment which results in the method production, to the unstable of temperature, PH, light etc., makes it can not promote the use of in luxury food and cosmetic field, significantly limit the range of application of radish red pigment.
Summary of the invention
The object of the invention is the deficiency of preparation for existing radish red pigment and purification process, provide preparation and purification process that radish red pigment is modified in a kind of esterification, it is short that described method has technical process, the easy and simple to handle and feature such as safety, save energy, unharmful substance discharge.Adopt the radish red pigment product prepared of the inventive method to improve the stability significance of temperature, PH, light, very big enrich the use range of radish red pigment at luxury food, cosmetic field etc.
The technical scheme realizing the object of the invention is: preparation and the purification process of radish red pigment are modified in a kind of esterification, with commercially available radish red pigment for raw material, first prepare the acyl chloride reaction liquid that radish red pigment is modified in esterification, radish red pigment solution is modified in rear preparation esterification, carry out purifying again, concentrate and prepare esterification modification radish red pigment concentrated solution, finally carry out lyophilize and obtain esterification modification radish red pigment product.The concrete steps of described method are as follows:
(1) the acyl chloride reaction liquid that radish red pigment is modified in esterification is prepared
First according to organic acid: the mass ratio of sulfur oxychloride is 1: the ratio of (15 ~ 25), joins in reaction vessel by described organic acid and sulfur oxychloride, rear rapid connection tipping has the reflux condensing tube of the drying tube of calcium chloride.Tail gas is absorbed with the sodium hydroxide solution that mass concentration is 10%.Then be placed in oil bath and be slowly heated to 65 ~ 75 DEG C, magnetic agitation 2 ~ 4h is to producing without gas.Then reaction product 70 DEG C of oil pump decompression rotary evaporations, steam unnecessary sulfur oxychloride.Collecting product, finally adding the product according to collecting: the mass ratio of methylene dichloride is 1: the methylene dichloride of the ratio of (2 ~ 4) joins in reaction solution, be the acyl chloride reaction liquid that radish red pigment is modified in esterification.Described organic acid is succsinic acid or hexosamine or dl pipecolinic acid etc.
(2) prepare esterification and modify radish red pigment solution
After (1) step completes, the acyl chloride reaction liquid that radish red pigment is modified in the esterification first (1) step obtained loads in dropping funnel, after according to commercially available radish red pigment: the mass ratio of pyridine is 1: the ratio of (10 ~ 15), described commercially available radish red pigment and pyridine are joined in three mouthfuls of reaction vessels, connect reflux condensing tube, thermometer and dropping funnel, be then placed in oil bath and be heated to 50 DEG C.Then drip according to (30 ~ 80)/speed of min drips the acyl chloride reaction liquid that radish red pigment is modified in esterification that (1) step obtains, reaction 4 ~ 7h.And then 50 DEG C of oil pump decompression rotary evaporations, steam pyridine and methylene dichloride.Be dissolved in water, the unreacted organic acid of centrifugal removing, just prepares esterification and modifies radish red pigment solution again.Described organic acid is succsinic acid or hexosamine or dl pipecolinic acid etc.
(3) prepare esterification and modify radish red pigment concentrated solution
After (2) step completes, the esterification of first (2) step being prepared is modified radish red pigment solution and is placed in the ultra-fine filter that molecular weight cut-off is 10000Da, under pressure is 0.16 ~ 0.2Mpa, carry out ultra-filtration and separation, when the trapped fluid volume in ultra-fine filter reduces to 10% ~ 20% of original volume, supplement distilled water to original volume, again under 0.16 ~ 0.2Mpa, carry out ultrafiltration, so repeat 3 ~ 6 times, the trapped fluid in ultra-fine filter be colourless till.Collect trapped fluid and filtered solution respectively, the trapped fluid of collection, containing macromole such as polysaccharide, can do raw materials of feed additives after concentrate drying; The filtered solution collected is that 500Da nanofiltration membrane carries out nanofiltration separation under pressure is 0.16 ~ 0.2Mpa with molecular weight cut-off, when nanofiltration trapped fluid volume reduces to 10% ~ 20% of original volume, supplement distilled water to original volume, again under 0.16 ~ 0.2Mpa, carry out nanofiltration, so repeat 3 ~ 6 times.Collect trapped fluid, be esterification and modify radish red pigment solution, be placed in vacuum concentrator, temperature be 55 ~ 80 DEG C, under vacuum tightness is the condition of 0.06 ~ 0.08Mpa, carry out vacuum concentration, till when soluble solid content reaches 20 ~ 30% in concentrated solution, just prepare esterification and modify radish red pigment concentrated solution.
(4) prepare esterification and modify radish red pigment product
After (3) step completes, the esterification of first (3) step being prepared is modified radish red pigment concentrated solution and is placed in freeze drier, pressure be 20 ~ 60Pa, under temperature is the condition of-40 ~-60 DEG C, lyophilize 24 ~ 48h, just prepare the esterification modification radish red pigment product that purity is 82.3 ~ 90.1%, the total recovery of product is 92.5 ~ 97.2%.
After the present invention adopts technique scheme, mainly contain following effect:
1, the inventive method adopts chemical process to carry out esterification modification to radish red pigment, improves to significance the stability of radish red pigment to temperature, and the radish red pigment before esterification modification is after temperature 100 DEG C heating 1h, and average loss rate is up to 18%; And the radish red pigment after esterification modification is after temperature 100 DEG C heating 1h, average loss rate is only 5%;
2, the inventive method adopts chemical process to carry out esterification modification to radish red pigment, improve to significance the stability of radish red pigment to pH, the color of radish red pigment changes along with the change of pH, radish red pigment before esterification modification has very big-difference under different pH, and the radish red pigment color in the scope of pH3 ~ 5 after esterification modification does not change substantially;
3, the inventive method adopts chemical process to carry out esterification modification to radish red pigment, improve to significance the stability of radish red pigment to light, under coloured light irradiation is fallen apart in indoor, radish red pigment before esterification modification is in 2 days, rate of loss is very little, also little 5 days internal loss rates, be only 11%, the radish red pigment after esterification modification did not nearly all lose in 5 days; Under outdoor natural light irradiates, the rate of loss that forward and backward radish red pigment is modified in esterification is all little, but after 5 days, the radish red pigment rate of loss before esterification modification reaches 55%, and the radish red pigment rate of loss after esterification modification is only 18%.
The inventive method can be widely used in preparation and radish red pigment product is modified in purification esterification.Radish red pigment product is modified in the esterification adopting the inventive method to prepare, can be widely used in the fields such as food, dyestuff, healthcare products, makeup, be specially adapted in the field such as luxury food, the cosmetics of super quality within the scope of high temperature resistant, resistance to illumination, different pH.
Embodiment
Below in conjunction with embodiment, further illustrate the present invention.
Embodiment 1
The concrete steps that a kind of succinic acid esterification modifies the preparation of radish red pigment and purification process are as follows:
(1) the acyl chloride reaction liquid that radish red pigment is modified in esterification is prepared
First according to succsinic acid: the mass ratio of sulfur oxychloride is the ratio of 1: 20, joins in reaction vessel by described organic acid and sulfur oxychloride, rear rapid connection tipping has the reflux condensing tube of the drying tube of calcium chloride.Tail gas is absorbed with the sodium hydroxide solution that mass concentration is 10%.Then be placed in oil bath and be slowly heated to 70 DEG C, magnetic agitation 4h is to producing without gas.Then reaction product 70 DEG C of oil pump decompression rotary evaporations, steam unnecessary sulfur oxychloride.Collecting product, finally adding the product according to collecting: the mass ratio of methylene dichloride is that the methylene dichloride of the ratio of 1: 2 joins in reaction solution, is the acyl chloride reaction liquid that radish red pigment is modified in esterification.
(2) prepare esterification and modify radish red pigment solution
After (1) step completes, the acyl chloride reaction liquid that radish red pigment is modified in the esterification first (1) step obtained loads in dropping funnel, after according to commercially available radish red pigment: the mass ratio of pyridine is the ratio of 1: 10, described commercially available radish red pigment and pyridine are joined in three mouthfuls of reaction vessels, connect reflux condensing tube, thermometer and dropping funnel, be then placed in oil bath and be heated to 50 DEG C.Then the acyl chloride reaction liquid of the esterification modification radish red pigment that (1) step obtains is dripped according to the speed of 60/min, reaction 5h.And then 50 DEG C of oil pump decompression rotary evaporations, steam pyridine and methylene dichloride.Be dissolved in water, the unreacted acetylsalicylic acid of centrifugal removing, just prepares esterification and modifies radish red pigment solution again.
(3) prepare esterification and modify radish red pigment concentrated solution
After (2) step completes, the esterification of first (2) step being prepared is modified radish red pigment solution and is placed in the ultra-fine filter that molecular weight cut-off is 10000Da, under pressure is 0.18Mpa, carry out ultra-filtration and separation, when the trapped fluid volume in ultra-fine filter reduces to 10% of original volume, supplement distilled water to original volume, again under 0.18Mpa, carry out ultrafiltration, so repeat 3 times, the trapped fluid in ultra-fine filter be colourless till.Collect trapped fluid and filtered solution respectively, the trapped fluid of collection, containing macromole such as polysaccharide, can do raw materials of feed additives after concentrate drying; The filtered solution collected is that the nanofiltration membrane of 500Da carries out nanofiltration separation under pressure is 0.18Mpa with molecular weight cut-off, when nanofiltration trapped fluid volume reduces to 10% of original volume, supplement distilled water to original volume, again under pressure is 0.18Mpa, carry out nanofiltration, so repeat 3 times.Collect trapped fluid, be esterification and modify radish red pigment solution, be placed in vacuum concentrator, temperature be 60 DEG C, under vacuum tightness is the condition of 0.06Mpa, carry out vacuum concentration, till when soluble solid content reaches 25% in concentrated solution, just prepare esterification and modify radish red pigment concentrated solution.
(4) prepare esterification and modify radish red pigment product
After (3) step completes, the esterification of first (3) step being prepared is modified radish red pigment concentrated solution and is placed in freeze drier, pressure be 50Pa, under temperature is the condition of-60 DEG C, lyophilize 48h, just prepare the esterification modification radish red pigment product that purity is 93.8%, the total recovery of product is 97.2%.
Radish red pigment product after esterification modification, after temperature 100 DEG C heating 1h, rate of loss is only 4.6%, and after outdoor natural light irradiates 5 days, rate of loss is only 16.3%.
Embodiment 2
Preparation and the purification process of radish red pigment are modified in hexosamine esterification, with embodiment 1, wherein:
In (1) step, hexosamine used: the mass ratio of sulfur oxychloride is 1: 15, is heated to 65 DEG C, stirs 3h, the product collected: the mass ratio of methylene dichloride is 1: 3.
In (2) step, radish red pigment: the mass ratio of pyridine is 1: 12, and flow velocity is 30/min, reaction 4h.
In (3) step, ultrafiltration pressure is 0.16Mpa, and trapped fluid volume reduces to 20% of original volume, and ultrafiltration pressure is 0.16Mpa, repeats 4 times.Nanofiltration pressure is 0.16Mpa, and trapped fluid volume reduces to 20% of original volume, and pressure is 0.16Mpa, and repeat 4 times, temperature is 55 DEG C, and vacuum tightness is 0.08Mpa, and soluble solid content reaches 20%.
In (4) step, pressure is 60Pa, temperature is-40 DEG C, lyophilize 24h, and it is 85.6% that radish red pigment product purity is modified in the esterification of preparing, and total recovery is 92.5%.
Radish red pigment product after esterification modification, after temperature 100 DEG C heating 1h, rate of loss is only 5.2%, and after outdoor natural light irradiates 5 days, rate of loss is only 18.5%.
Embodiment 3
Preparation and the purification process of radish red pigment are modified in dl pipecolinic acid esterification, with embodiment 1, wherein:
In (1) step, dl pipecolinic acid used: the mass ratio of sulfur oxychloride is 1: 25, is heated to 75 DEG C, stirs 2h, the product collected: the mass ratio of methylene dichloride is 1: 4.
In (2) step, radish red pigment: the mass ratio of pyridine is 1: 15, and flow velocity is 80/min, reaction 7h.
In (3) step, ultrafiltration pressure is 0.2Mpa, and trapped fluid volume reduces to 15% of original volume, and ultrafiltration pressure is 0.2Mpa, repeats 6 times.Nanofiltration pressure is 0.2Mpa, and trapped fluid volume reduces to 15% of original volume, and pressure is 0.2Mpa, and repeat 6 times, temperature is 80 DEG C, and vacuum tightness is 0.07Mpa, and soluble solid content reaches 30%.
In (4) step, pressure is 20Pa, temperature is-50 DEG C, lyophilize 32h, and it is 90.4% that radish red pigment product purity is modified in the esterification of preparing, and total recovery is 96.1%.
Radish red pigment product after esterification modification, after temperature 100 DEG C heating 1h, rate of loss is only 4.7%, and after outdoor natural light irradiates 5 days, rate of loss is only 17.8%.
Claims (4)
1. preparation and a purification process for radish red pigment is modified in esterification, it is characterized in that the concrete steps of described method are as follows:
(1) the acyl chloride reaction liquid that radish red pigment is modified in esterification is prepared
First according to organic acid: the mass ratio of sulfur oxychloride is 1: the ratio of (15 ~ 25), described organic acid and sulfur oxychloride are joined in reaction vessel, the rear tipping of connection rapidly has the reflux condensing tube of the drying tube of calcium chloride, tail gas is absorbed with the sodium hydroxide solution that mass concentration is 10%, then be placed in oil bath and be slowly heated to 65 ~ 75 DEG C, magnetic agitation 2 ~ 4h is to producing without gas, then reaction product 70 DEG C of oil pump decompression rotary evaporations, steam unnecessary sulfur oxychloride, collect product, finally add the product according to collecting: the mass ratio of methylene dichloride is 1: the methylene dichloride of the ratio of (2 ~ 4) joins in reaction solution, be the acyl chloride reaction liquid that radish red pigment is modified in esterification, described organic acid is succsinic acid or hexosamine or dl pipecolinic acid etc.,
(2) prepare esterification and modify radish red pigment solution
After (1) step completes, the acyl chloride reaction liquid that radish red pigment is modified in the esterification first (1) step obtained loads in dropping funnel, after according to commercially available radish red pigment: the mass ratio of pyridine is 1: the ratio of (10 ~ 15), described commercially available radish red pigment and pyridine are joined in three mouthfuls of reaction vessels, connect reflux condensing tube, thermometer and dropping funnel, then be placed in oil bath and be heated to 50 DEG C, then drip according to (30 ~ 80)/speed of min drips the acyl chloride reaction liquid that radish red pigment is modified in esterification that (1) step obtains, reaction 4 ~ 7h, and then 50 DEG C of oil pump decompression rotary evaporations, steam pyridine and methylene dichloride, be dissolved in water again, the unreacted organic acid of centrifugal removing, just prepare esterification and modify radish red pigment solution, described organic acid is succsinic acid or hexosamine or dl pipecolinic acid etc.,
(3) prepare esterification and modify radish red pigment concentrated solution
After (2) step completes, the esterification of first (2) step being prepared is modified radish red pigment solution and is placed in the ultra-fine filter that molecular weight cut-off is 10000Da, under pressure is 0.16 ~ 0.2Mpa, carry out ultra-filtration and separation, when the trapped fluid volume in ultra-fine filter reduces to 10% ~ 20% of original volume, supplement distilled water to original volume, again under 0.16 ~ 0.2Mpa, carry out ultrafiltration, repetition like this 3 ~ 6 times, trapped fluid in ultra-fine filter be colourless till, collect trapped fluid and filtered solution respectively, the trapped fluid collected is containing macromole such as polysaccharide, raw materials of feed additives can be done after concentrate drying, the filtered solution collected, be that 500Da nanofiltration membrane carries out nanofiltration separation under pressure is 0.16 ~ 0.2Mpa with molecular weight cut-off, when nanofiltration trapped fluid volume reduces to 10% ~ 20% of original volume, supplement distilled water to original volume, again under 0.16 ~ 0.2Mpa, carry out nanofiltration, repetition like this 3 ~ 6 times, collect trapped fluid, be esterification and modify radish red pigment solution, be placed in vacuum concentrator, it is 55 ~ 80 DEG C in temperature, vacuum tightness is under the condition of 0.06 ~ 0.08Mpa, carry out vacuum concentration, till when in concentrated solution, soluble solid content reaches 20 ~ 30%, just prepare esterification and modify radish red pigment concentrated solution,
(4) prepare esterification and modify radish red pigment product
After (3) step completes, the esterification of first (3) step being prepared is modified radish red pigment concentrated solution and is placed in freeze drier, pressure be 20 ~ 60Pa, under temperature is the condition of-40 ~-60 DEG C, lyophilize 24 ~ 48h, just prepare the esterification modification radish red pigment product that purity is 82.3 ~ 90.1%, the total recovery of product is 90.2 ~ 96.5%.
2. modify the preparation of radish red pigment and the concrete steps of purification process according to a kind of esterification according to claim 1, it is characterized in that:
In (1) step, organic acid used is succsinic acid, succsinic acid used: the mass ratio of sulfur oxychloride is 1: 20, is heated to 70 DEG C, stirs 4h, the product collected: the mass ratio of methylene dichloride is 1: 2;
In (2) step, radish red pigment: the mass ratio of pyridine is 1: 10, and flow velocity is 60/min, reaction 5h;
In (3) step, ultrafiltration pressure is 0.18Mpa, and trapped fluid volume reduces to 10% of original volume, and ultrafiltration pressure is 0.18Mpa, repeat 3 times, nanofiltration pressure is 0.18Mpa, and trapped fluid volume reduces to 10% of original volume, and pressure is 0.18Mpa, repeat 3 times, temperature is 60 DEG C, and vacuum tightness is 0.06Mpa, and soluble solid content reaches 25%;
In (4) step, pressure is 50Pa, temperature is-60 DEG C, lyophilize 48h, and it is 90.1% that radish red pigment product purity is modified in the esterification of preparing, and total recovery is 96.5%.
3. modify the preparation of radish red pigment and the concrete steps of purification process according to a kind of esterification according to claim 1, it is characterized in that:
In (1) step, organic acid used is hexosamine, hexosamine used: the mass ratio of sulfur oxychloride is 1: 15, is heated to 65 DEG C, stirs 3h, the product collected: the mass ratio of methylene dichloride is 1: 3;
In (2) step, radish red pigment: the mass ratio of pyridine is 1: 12, and flow velocity is 30/min, reaction 4h;
In (3) step, ultrafiltration pressure is 0.16Mpa, and trapped fluid volume reduces to 20% of original volume, and ultrafiltration pressure is 0.16Mpa, repeat 4 times, nanofiltration pressure is 0.16Mpa, and trapped fluid volume reduces to 20% of original volume, and pressure is 0.16Mpa, repeat 4 times, temperature is 55 DEG C, and vacuum tightness is 0.08Mpa, and soluble solid content reaches 20%;
In (4) step, pressure is 60Pa, temperature is-40 DEG C, lyophilize 24h, and it is 82.3% that radish red pigment product purity is modified in the esterification of preparing, and total recovery is 90.2%.
4. modify the preparation of radish red pigment and the concrete steps of purification process according to a kind of esterification according to claim 1, it is characterized in that:
In (1) step, organic acid used is dl pipecolinic acid, dl pipecolinic acid used: the mass ratio of sulfur oxychloride is 1: 25, is heated to 75 DEG C, stirs 2h, the product collected: the mass ratio of methylene dichloride is 1: 4;
In (2) step, radish red pigment: the mass ratio of pyridine is 1: 15, and flow velocity is 80/min, reaction 7h;
In (3) step, ultrafiltration pressure is 0.2Mpa, and trapped fluid volume reduces to 15% of original volume, and ultrafiltration pressure is 0.2Mpa, repeat 6 times, nanofiltration pressure is 0.2Mpa, and trapped fluid volume reduces to 15% of original volume, and pressure is 0.2Mpa, repeat 6 times, temperature is 80 DEG C, and vacuum tightness is 0.07Mpa, and soluble solid content reaches 30%;
In (4) step, pressure is 20Pa, temperature is-50 DEG C, lyophilize 32h, and it is 88.7% that radish red pigment product purity is modified in the esterification of preparing, and total recovery is 94.8%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510976867.5A CN105504865A (en) | 2015-12-15 | 2015-12-15 | Preparation and purification method of esterification modified radish red pigments |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510976867.5A CN105504865A (en) | 2015-12-15 | 2015-12-15 | Preparation and purification method of esterification modified radish red pigments |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN105504865A true CN105504865A (en) | 2016-04-20 |
Family
ID=55713184
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510976867.5A Pending CN105504865A (en) | 2015-12-15 | 2015-12-15 | Preparation and purification method of esterification modified radish red pigments |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105504865A (en) |
Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5536504A (en) * | 1993-11-19 | 1996-07-16 | Marigen S.A. | Ultramicroemulsions from spontaneously dispersible concentrates containing xanthophyll esters and having antitumor activity |
| JP3047221B2 (en) * | 1997-09-22 | 2000-05-29 | 株式会社宗商 | Crustacean coloring method and colored crustaceans |
| CN1278786A (en) * | 1997-11-25 | 2001-01-03 | 奥格尼卡工业公司 | Short chain diesters and process for their production |
| CN1492855A (en) * | 2001-02-23 | 2004-04-28 | ����ά�й��ʹ�˾ | Novel carotenoid esters |
| CN1628097A (en) * | 2002-02-06 | 2005-06-15 | Dsmip资产公司 | Astaxanthin esters |
| CN102134402A (en) * | 2011-01-04 | 2011-07-27 | 重庆海巨农业发展有限公司 | Method for preparing and purifying alkylated radish red pigment |
| CN102174617A (en) * | 2011-01-04 | 2011-09-07 | 重庆大学 | Method for synthesizing and purifying glycosylated red radish haematochrome |
| CN103958614A (en) * | 2011-11-28 | 2014-07-30 | 科·汉森有限公司 | Anthocyanin-based colorant |
| CN104419220A (en) * | 2013-09-11 | 2015-03-18 | 青岛鹏远康华天然产物有限公司 | Method for high-efficiency extraction of pumpkin pigments |
| CN104529988A (en) * | 2014-11-16 | 2015-04-22 | 青海大学 | A chemical modification method for a highland natural dye sensitizer |
| CN104719894A (en) * | 2015-03-24 | 2015-06-24 | 武汉志邦化学技术有限公司 | Beta-carotene microcapsule and preparation technology thereof |
-
2015
- 2015-12-15 CN CN201510976867.5A patent/CN105504865A/en active Pending
Patent Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5536504A (en) * | 1993-11-19 | 1996-07-16 | Marigen S.A. | Ultramicroemulsions from spontaneously dispersible concentrates containing xanthophyll esters and having antitumor activity |
| JP3047221B2 (en) * | 1997-09-22 | 2000-05-29 | 株式会社宗商 | Crustacean coloring method and colored crustaceans |
| CN1278786A (en) * | 1997-11-25 | 2001-01-03 | 奥格尼卡工业公司 | Short chain diesters and process for their production |
| CN1492855A (en) * | 2001-02-23 | 2004-04-28 | ����ά�й��ʹ�˾ | Novel carotenoid esters |
| CN1628097A (en) * | 2002-02-06 | 2005-06-15 | Dsmip资产公司 | Astaxanthin esters |
| CN102134402A (en) * | 2011-01-04 | 2011-07-27 | 重庆海巨农业发展有限公司 | Method for preparing and purifying alkylated radish red pigment |
| CN102174617A (en) * | 2011-01-04 | 2011-09-07 | 重庆大学 | Method for synthesizing and purifying glycosylated red radish haematochrome |
| CN103958614A (en) * | 2011-11-28 | 2014-07-30 | 科·汉森有限公司 | Anthocyanin-based colorant |
| CN104419220A (en) * | 2013-09-11 | 2015-03-18 | 青岛鹏远康华天然产物有限公司 | Method for high-efficiency extraction of pumpkin pigments |
| CN104529988A (en) * | 2014-11-16 | 2015-04-22 | 青海大学 | A chemical modification method for a highland natural dye sensitizer |
| CN104719894A (en) * | 2015-03-24 | 2015-06-24 | 武汉志邦化学技术有限公司 | Beta-carotene microcapsule and preparation technology thereof |
Non-Patent Citations (1)
| Title |
|---|
| 卢晓蕊等: "响应面法优化萝卜红色素酯化修饰条件的研究", 《食品与发酵工业》 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105294790B (en) | A method of extracting high-purity stevioside from STEVIA REBAUDIANA | |
| CN103450703B (en) | Method for preparing high-purity taste-removing purple sweet potato pigment | |
| CN101962486B (en) | Industrial production method for extracting natural purple sweet potato coloring matter for food from edible purple sweet potato | |
| CN103432193A (en) | Microwave-assisted aqueous two-phase extraction and separation method of kudzu root total flavones | |
| CN103102408B (en) | Method for extracting phycocyanin from spirulina | |
| CN107552536B (en) | Comprehensive extraction process of wine waste residues | |
| CN106397630A (en) | Method for extracting sodium hyaluronate based on membrane separation technology | |
| CN102617693B (en) | Method utilizing subcritical water extraction technology to extract and prepare ursolic acid from loquat leaves | |
| CN102702379A (en) | Extraction and preparation process of citrus pectin | |
| CN107652337B (en) | Method for extracting and preparing anthocyanin such as black rice, black beans, purple potatoes, roses, peonies and the like | |
| CN103304677B (en) | A kind of method of separation and purification Rhizoma amorphophalli glucomannan | |
| CN110818585A (en) | Separation method for simultaneously preparing five dopamine compounds from aspongopus | |
| CN110721206A (en) | Deep eutectic solvent for extracting phellinus igniarius flavone and preparation method and extraction method thereof | |
| CN104761596A (en) | Method for preparing anthocyanin standard substance | |
| CN104069191B (en) | A kind of extraction process of water polygonum flaccidum general flavone | |
| CN102924969A (en) | Method for refining paprika red pigment | |
| CN1939458B (en) | Preparation of gardenia jasminoides by macroporous adsorbing resin | |
| CN105504865A (en) | Preparation and purification method of esterification modified radish red pigments | |
| CN104739914B (en) | A kind of method that metal complex isolates and purifies affine cudweed flavonoids | |
| CN104630302A (en) | Enzyme process acylation method of strawberry anthocyanin | |
| CN110141605A (en) | A kind of preparation method of snowpoppy total alkaloid nanoparticle | |
| LU102716B1 (en) | Method for Extracting Anthocyanin from Perillafrutescens (L.) Britton Leaves by Using Ternary Deep Eutectic Solvent | |
| CN104432109A (en) | Method for preparing sulfated water-soluble dietary fiber employing extrusion | |
| CN102040748B (en) | Ganoderma sinensis mycelium anti-tumor polysaccharide component GS-C as well as preparation method and application thereof | |
| CN104962394B (en) | A kind of method that mucor processing pineapple juice prepares cigarette pineapple flavors |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20160420 |
|
| RJ01 | Rejection of invention patent application after publication |