CN115057805A - Method for preparing canthaxanthin crystal with high all-trans isomer stability - Google Patents
Method for preparing canthaxanthin crystal with high all-trans isomer stability Download PDFInfo
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- CN115057805A CN115057805A CN202210525878.1A CN202210525878A CN115057805A CN 115057805 A CN115057805 A CN 115057805A CN 202210525878 A CN202210525878 A CN 202210525878A CN 115057805 A CN115057805 A CN 115057805A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/24—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by six-membered non-aromatic rings, e.g. beta-carotene
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/09—Geometrical isomers
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Abstract
The invention relates to a method for preparing high all-trans isomer stability canthaxanthin crystals, which comprises the steps of preparing the high all-trans isomer stability canthaxanthin crystals, wherein the total content of sodium ions and potassium ions is 0-50ppm, and the total content of chlorine is 0-75 ppm; preferably, the total content of sodium and potassium ions in the canthaxanthin crystals is 0 to 20ppm, and the total chlorine content is 0 to 30 ppm. The canthaxanthin crystal can be used for preparing canthaxanthin powder, and the proportion of all-trans isomers can reach 90-95%.
Description
Technical Field
The invention belongs to the field of nutritional chemicals, and particularly relates to a method for preparing canthaxanthin crystals with high all-trans isomer stability.
Background
Canthaxanthin is an important carotenoid, is also a natural pigment with great potential antioxidant, has the capacity of quenching active oxygen and eliminating free radicals, is second to astaxanthin in capacity of quenching active oxygen and eliminating free radicals, is nearly twice as much as beta-carotene and fifty times as much as vitamin E, is also called super vitamin E, can be used for coloring the skin and yolk of poultry, and can also be applied to the fields of cosmetics and medical treatment.
CN111825588 takes beta-carotene as a raw material, takes metal calcium salt as a catalyst and takes peroxide as an oxidant to prepare canthaxanthin. CN101633633 process for preparing canthaxanthin is oxidizing beta-carotene with chlorate or bromate in the presence of catalyst. The method of CN1417207 uses hypobromous acid generated by the combination of sulfurous acid, bisulfite or bisulfite and bromate as the oxidizing agent.
In the above-mentioned methods for preparing canthaxanthin, inorganic salts such as chlorate, bromate and the like are inevitably introduced and cannot be sufficiently removed, so that the obtained canthaxanthin crystals contain high content of the inorganic salts, and the all-trans isomer is largely converted into the cis isomer in the preparation process, thereby reducing the quality of canthaxanthin. Therefore, effective control of the inorganic salt content in the canthaxanthin crystals becomes critical.
Disclosure of Invention
The invention discovers that the high content of inorganic salt in canthaxanthin crystals can cause that a large amount of all-trans isomers are converted into cis isomers in the preparation process, thereby reducing the quality of canthaxanthin. Therefore, the inorganic salt content in the canthaxanthin crystal needs to be strictly controlled by adopting an effective means, so that the aim of preparing the high all-trans isomer stability canthaxanthin crystal is fulfilled.
In order to achieve the above purpose, the technical scheme of the invention is as follows:
in one aspect, the invention provides a high all-trans isomer stability canthaxanthin crystal, wherein the total content of sodium ions and potassium ions in the high all-trans isomer stability canthaxanthin crystal is 0-50ppm, and the total content of chlorine is 0-75 ppm; preferably, the total content of sodium and potassium ions in the canthaxanthin crystals is 0 to 20ppm, and the total chlorine content is 0 to 30 ppm.
In another aspect, the present invention provides a method for preparing canthaxanthin crystals with high all-trans isomer stability, which comprises the following steps:
(1) the beta-carotene is subjected to oxidation reaction under the action of a catalyst and an oxidant;
(2) after the reaction is finished, quenching, washing, adsorbing and desolventizing to obtain a canthaxanthin crude product;
(3) carrying out isomerization reaction on the canthaxanthin crude product under the action of an isomerization solvent;
(4) the canthaxanthin crystal is obtained after the operations of centrifugation, washing and drying.
Wherein the total content of sodium and potassium ions in the canthaxanthin crystals obtained in the step (4) is 0-50ppm, and the total chlorine content is 0-75 ppm; preferably, the sodium ion content of the canthaxanthin crystal is 0 to 20ppm, and the total chlorine content is 0 to 30 ppm.
Preferably, the oxidant in step (1) is at least one selected from the group consisting of potassium chlorate, sodium chlorite, potassium chlorite, sodium hypochlorite and potassium hypochlorite.
Preferably, the catalyst in the step (1) is at least any one selected from sodium iodide and potassium iodide.
Preferably, in the step (1), the catalyst and the oxidant are dissolved in water, and a mixed solution of beta-carotene and an organic solvent is added, so that the beta-carotene is subjected to an oxidation reaction under the action of the catalyst and the oxidant; preferably, the organic solvent is selected from at least any one of chloroform, dichloromethane, dichloroethane, n-propyl acetate, methanol, and ethanol.
Preferably, the mass ratio of the beta-carotene to the catalyst to the oxidant to the water to the organic solvent is 1:0.02-0.2:0.5-2:10-50:10-100, preferably 1:0.1-0.15:1-1.5:20-40: 20-60.
Preferably, the reaction temperature of the oxidation reaction in the step (1) is-10 to 30 ℃, and preferably-5 to 20 ℃; the reaction pressure is 0.1MPaA to 0.5MPaA, preferably 0.1MPaA to 0.2 MPaA; the reaction time is 6-30h, preferably 8-24 h.
Preferably, the quenching agent of the quenching step in the step (2) is selected from at least any one of sodium thiosulfate and potassium thiosulfate; the mass of the quenching agent is 1.5 to 5 times, preferably 2 to 4 times that of the catalyst.
Preferably, the mass of the deionized water used for washing in the step (2) is 0.5-2 times of that of the reaction water, and preferably 1-1.5 times; the washing time is 0.5-3h, preferably 1-2 h.
Preferably, the adsorbent used in the adsorption operation in step (2) is at least any one of activated alumina, diatomaceous earth, silica gel, activated carbon and adsorption resin.
Preferably, the mass of the adsorbent is 5 to 20 times, preferably 10 to 15 times the amount of the oxidant.
Preferably, the isomerization solvent in the step (3) is at least one selected from ethanol, acetone, n-propyl acetate, n-heptane, toluene and methanol.
Preferably, the mass ratio of the canthaxanthin crude product to the isomeric solvent in the step (3) is 1:10-100, preferably 1: 20-40.
Preferably, the reaction temperature of the isomerization reaction in the step (3) is 50-120 ℃, preferably 70-110 ℃; the reaction pressure is 0.1MPaA-1MPaA, preferably 0.1MPaA-0.5 MPaA; the reaction time is 6-30h, preferably 10-15 h.
The canthaxanthin crystal prepared by the experimental scheme is used for the development of a preparation process, and the proportion of all-trans isomers in the obtained canthaxanthin preparation can reach 90-95%.
By adopting the technical scheme, the invention has the following positive effects:
(1) the canthaxanthin crystal prepared by the experimental scheme has high all-trans content and good product stability;
(2) the preparation process does not lead to the great conversion of all-trans isomer into cis isomer, and the product quality is high.
Detailed Description
The following examples will further illustrate the method provided by the present invention in order to better understand the technical solution of the present invention, but the present invention is not limited to the listed examples, and also includes any other known modifications within the scope of the claims of the present invention.
The production process of the present invention will be described in more detail with reference to the following examples, but the present invention is not limited to the following examples.
The following examples and comparative examples use the following information on the main raw materials:
beta-carotene, BASF;
chloroform, dichloromethane, dichloroethane, n-propyl acetate, methanol, ethanol, acetone, n-heptane, toluene, analytically pure, welibench technologies ltd;
potassium chlorate, sodium chlorite, potassium chlorite, sodium hypochlorite, potassium hypochlorite, sodium iodide, potassium iodide, sodium thiosulfate, potassium thiosulfate, activated alumina, diatomite, silica gel, activated carbon, adsorption resin, analytically pure, alatin.
The liquid chromatography reaction test conditions of the invention are as follows: the chromatographic type is as follows: agilent 1260; a chromatographic column: a C30 column; mobile phase: a: acetonitrile, B: isopropyl alcohol; column temperature: 40 ℃; flow rate: 1.0 mL/min; sample introduction amount: 10 mu L of the solution; detection wavelength: 476 nm.
Example 1
Mixing beta-carotene, sodium hypochlorite, sodium iodide, water and dichloroethane according to the mass ratio of 1:0.1:1:40:60, reacting for 8 hours at 20 ℃ under the condition of 0.1MPaA, quenching by sodium thiosulfate with the mass of 2 times of a catalyst, washing for 2 hours by deionized water with the mass of 2 times of reaction water, adsorbing by active alumina with the mass of 10 times of an oxidant, after solvent removal operation, mixing the obtained canthaxanthin crude product with n-propyl acetate according to the mass ratio of 1:20, reacting for 8 hours at 100 ℃ under the condition of 0.5MPaA, centrifuging, washing and drying to obtain the canthaxanthin crystal. The yield of the oxidation reaction was 82%, the yield of the isomerization reaction was 96%, the all-trans isomer content in the obtained canthaxanthin crystal was 94.1% (sodium ion content was 15ppm, total chlorine content was 25ppm), and the all-trans isomer content in the canthaxanthin preparation product obtained by the formulation operation was 93.6%.
Example 2
Mixing beta-carotene, potassium chlorate, potassium iodide, water and dichloromethane according to the mass ratio of 1:0.02:0.5:50:100, reacting for 30 hours at-10 ℃ and 0.2MPaA, quenching by potassium thiosulfate with the mass of 4 times of a catalyst, washing for 1 hour by deionized water with the mass of 2 times of reaction water, adsorbing by activated carbon with the mass of 5 times of an oxidant, after solvent removal operation, mixing the obtained canthaxanthin crude product with ethanol according to the mass ratio of 1:100, reacting for 6 hours at 120 ℃ and 0.3MPaA, centrifuging, washing and drying to obtain the canthaxanthin crystal. The yield of the oxidation reaction was 81%, the yield of the isomerization reaction was 97%, the all-trans isomer content in the obtained canthaxanthin crystal was 94.3% (potassium ion content was 16ppm, total chlorine content was 20ppm), and the all-trans isomer content in the canthaxanthin preparation product obtained by the formulation operation was 93.7%.
Example 3
Mixing beta-carotene, sodium chlorate, sodium iodide, water and chloroform according to the mass ratio of 1:0.2:2:10:10, reacting for 24 hours at-5 ℃ under the condition of 0.4MPaA, quenching by sodium thiosulfate with the mass of 1.5 times of that of a catalyst, washing for 0.5 hour by deionized water with the mass of 0.5 time of that of reaction water, adsorbing by diatomite with the mass of 20 times of that of an oxidant, after the operation of solvent removal, mixing the obtained canthaxanthin crude product with acetone according to the mass ratio of 1:40, reacting for 30 hours at 70 ℃ under 1MPaA, centrifuging, washing and drying to obtain the canthaxanthin crystals. The yield of the oxidation reaction was 83%, the yield of the isomerization reaction was 95%, the all-trans isomer content in the obtained canthaxanthin crystal was 93.8% (sodium ion content was 30ppm, total chlorine content was 45ppm), and the all-trans isomer content in the canthaxanthin preparation product obtained by the formulation operation was 92.9%.
Example 4
Mixing beta-carotene, sodium chlorite, sodium iodide, water and methanol according to the mass ratio of 1:0.15:1:20:20, reacting for 6 hours at 30 ℃ under the condition of 0.5MPaA, quenching by sodium thiosulfate with the mass of 5 times of catalyst, washing for 3 hours by deionized water with the mass of 1.5 times of reaction water, adsorbing by using adsorption resin with the mass of 15 times of oxidant, after solvent removal operation, mixing the obtained canthaxanthin crude product with n-heptane according to the mass ratio of 1:10, reacting for 10 hours at 110 ℃ under 0.3MPaA, centrifuging, washing and drying to obtain the canthaxanthin crystal. The yield of the oxidation reaction is 80%, the yield of the isomerization reaction is 96%, the all-trans isomer content in the obtained canthaxanthin crystal is 94.2% (the sodium ion content is 50ppm, the total chlorine content is 75ppm), and the all-trans isomer content in the canthaxanthin preparation product obtained by the preparation operation is 92.1%.
Example 5
Mixing beta-carotene, potassium hypochlorite, potassium iodide, water and n-propyl acetate according to the mass ratio of 1:0.1:1.5:40:60, reacting for 20 hours at 10 ℃ under the condition of 0.3MPaA, quenching by potassium thiosulfate with the mass of 3 times of that of a catalyst, washing for 1.5 hours by deionized water with the mass of 1 time of reaction water, adsorbing by silica gel with the mass of 10 times of an oxidant, after solvent removal operation, mixing the obtained canthaxanthin crude product with toluene according to the mass ratio of 1:60, reacting for 15 hours at 50 ℃ under 0.1MPaA, centrifuging, washing and drying to obtain the canthaxanthin crystals. The yield of the oxidation reaction was 81%, the yield of the isomerization reaction was 95%, the all-trans isomer content in the obtained canthaxanthin crystal was 93.2% (potassium ion content was 30ppm, total chlorine content was 30ppm), and the all-trans isomer content in the canthaxanthin preparation product obtained by the formulation operation was 91.8%.
Comparative example 1
The adsorption procedure was absent compared to example 1. The yield of the oxidation reaction is 82 percent, the yield of the isomerization reaction is 92 percent, the all-trans isomer content in the obtained canthaxanthin crystal is 93.1 percent (the sodium ion content is 90ppm, the total chlorine content is 125ppm), and the all-trans isomer content in the canthaxanthin preparation product obtained by the preparation operation is 72.1 percent.
Comparative example 2
Compared with example 1, the adsorbent is used in an amount of 1 time the mass of the activated alumina as the oxidant. The yield of the oxidation reaction was 82%, the yield of the isomerization reaction was 93%, the all-trans isomer content in the obtained canthaxanthin crystal was 93.5% (sodium ion content was 75ppm, total chlorine content was 92ppm), and the all-trans isomer content in the canthaxanthin preparation product obtained by the formulation operation was 80.1%.
As can be seen from the comparison between example 1 and comparative examples 1 and 2, the content of inorganic salts in canthaxanthin crystals obtained by adsorption operation is obviously reduced, so that the content of all-trans isomers in the canthaxanthin preparation is obviously improved.
While the present invention has been described in detail with reference to the preferred embodiments, it should be understood that the above description should not be taken as limiting the invention. It will be appreciated by those skilled in the art that modifications or adaptations to the invention may be made in light of the teachings of the present specification. Such modifications or adaptations are intended to be within the scope of the present invention as defined in the claims.
Claims (10)
1. A high all-trans isomer stability canthaxanthin crystal is characterized in that the total content of sodium ions and potassium ions in the high all-trans isomer stability canthaxanthin crystal is 0-50ppm, and the total content of chlorine is 0-75 ppm; preferably, the total content of sodium and potassium ions in the canthaxanthin crystals is 0 to 20ppm, and the total chlorine content is 0 to 30 ppm.
2. A method for preparing high all-trans isomer stability canthaxanthin crystals comprises the following steps:
(1) the beta-carotene is subjected to oxidation reaction under the action of a catalyst and an oxidant;
(2) after the reaction is finished, quenching, washing, adsorbing and removing the solvent to obtain a canthaxanthin crude product;
(3) carrying out isomerization reaction on the canthaxanthin crude product under the action of an isomerization solvent;
(4) the canthaxanthin crystal is obtained after the operations of centrifugation, washing and drying.
3. The method of claim 2, wherein the oxidant in step (1) is selected from at least any one of potassium chlorate, sodium chlorite, potassium chlorite, sodium hypochlorite, and potassium hypochlorite; and/or, the catalyst in the step (1) is selected from at least any one of sodium iodide and potassium iodide.
4. The method according to any one of claims 2 to 3, wherein step (1) is in particular: dissolving a catalyst and an oxidant in water, adding the mixture of beta-carotene and an organic solvent, and carrying out an oxidation reaction on the beta-carotene under the action of the catalyst and the oxidant; preferably, the organic solvent is selected from at least any one of chloroform, dichloromethane, dichloroethane, n-propyl acetate, methanol, and ethanol.
5. The method according to claim 4, wherein the mass ratio of the beta-carotene to the catalyst to the oxidant to the water to the organic solvent is 1:0.02-0.2:0.5-2:10-50:10-100, preferably 1:0.1-0.15:1-1.5:20-40: 20-60.
6. The method according to any one of claims 2 to 5, wherein the oxidation reaction in step (1) is carried out at a reaction temperature of-10 to 30 ℃, preferably-5 to 20 ℃; the reaction pressure is 0.1MPaA to 0.5MPaA, preferably 0.1MPaA to 0.2 MPaA; the reaction time is 6-30h, preferably 8-24 h.
7. The method according to any one of claims 2 to 6, wherein the quenching agent of the quenching step in the step (2) is selected from at least any one of sodium thiosulfate and potassium thiosulfate; the mass of the quenching agent is 1.5 to 5 times, preferably 2 to 4 times that of the catalyst; and/or the mass of the deionized water used for washing in the step (2) is 0.5-2 times of that of the reaction water, preferably 1-1.5 times; the washing time is 0.5-3h, preferably 1-2 h.
8. The method according to any one of claims 2 to 7, wherein the adsorbent used in the adsorption operation in the step (2) is at least any one of activated alumina, diatomaceous earth, silica gel, activated carbon, and adsorption resin; and/or the mass of the adsorbent is 5 to 20 times of the dosage of the oxidant, preferably 10 to 15 times.
9. The method according to any one of claims 2 to 8, wherein the isomerization solvent in the step (3) is at least any one selected from ethanol, acetone, n-propyl acetate, n-heptane, toluene and methanol.
10. The method according to any one of claims 2 to 9, wherein the mass ratio of the crude canthaxanthin and the isomeric solvent in the step (3) is 1:10 to 100, preferably 1:20 to 40; and/or the reaction temperature of the isomerization reaction in the step (3) is 50-120 ℃, preferably 70-110 ℃; the reaction pressure is 0.1MPaA-1MPaA, preferably 0.1MPaA-0.5 MPaA; the reaction time is 6-30h, preferably 10-15 h.
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