CN115850223A - Method for purifying and desalting vitriol reason - Google Patents
Method for purifying and desalting vitriol reason Download PDFInfo
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- CN115850223A CN115850223A CN202211652670.2A CN202211652670A CN115850223A CN 115850223 A CN115850223 A CN 115850223A CN 202211652670 A CN202211652670 A CN 202211652670A CN 115850223 A CN115850223 A CN 115850223A
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- 238000011033 desalting Methods 0.000 title claims abstract description 26
- 238000000034 method Methods 0.000 title claims abstract description 22
- 239000012043 crude product Substances 0.000 claims abstract description 22
- 238000000746 purification Methods 0.000 claims abstract description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 108010031318 Vitronectin Proteins 0.000 claims abstract description 13
- 102100035140 Vitronectin Human genes 0.000 claims abstract description 13
- 238000001914 filtration Methods 0.000 claims abstract description 10
- 239000012528 membrane Substances 0.000 claims abstract description 9
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims abstract description 8
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims abstract description 7
- 238000010612 desalination reaction Methods 0.000 claims abstract description 7
- 238000005374 membrane filtration Methods 0.000 claims abstract description 7
- 239000000047 product Substances 0.000 claims abstract description 7
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000010791 quenching Methods 0.000 claims abstract description 5
- 230000000171 quenching effect Effects 0.000 claims abstract description 5
- 238000007865 diluting Methods 0.000 claims abstract description 4
- NIFJEQGFAKTKFF-KVPKETBZSA-N 1-[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]propan-2-one Chemical compound CC(=O)C[C@@H]1OC[C@@H](O)[C@H](O)[C@H]1O NIFJEQGFAKTKFF-KVPKETBZSA-N 0.000 claims abstract description 3
- 239000005740 Boscalid Substances 0.000 claims abstract description 3
- 239000012670 alkaline solution Substances 0.000 claims abstract description 3
- WYEMLYFITZORAB-UHFFFAOYSA-N boscalid Chemical compound C1=CC(Cl)=CC=C1C1=CC=CC=C1NC(=O)C1=CC=CN=C1Cl WYEMLYFITZORAB-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229940118790 boscalid Drugs 0.000 claims abstract description 3
- 238000006482 condensation reaction Methods 0.000 claims abstract description 3
- 230000000911 decarboxylating effect Effects 0.000 claims abstract description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 3
- 239000002994 raw material Substances 0.000 claims abstract description 3
- 238000010992 reflux Methods 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims 1
- 238000009776 industrial production Methods 0.000 abstract description 2
- 239000002351 wastewater Substances 0.000 abstract description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- 239000000243 solution Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 239000008213 purified water Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- KOGFZZYPPGQZFZ-QVAPDBTGSA-N (2s,3r,4s,5r)-2-(2-hydroxypropyl)oxane-3,4,5-triol Chemical compound CC(O)C[C@@H]1OC[C@@H](O)[C@H](O)[C@H]1O KOGFZZYPPGQZFZ-QVAPDBTGSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000004321 preservation Methods 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DDADCBXAKYGDEH-UHFFFAOYSA-N 2-(3-hydroxypropyl)oxane-2,3,4-triol Chemical compound OCCCC1(O)OCCC(O)C1O DDADCBXAKYGDEH-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 238000010587 phase diagram Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 150000003741 xylose derivatives Chemical class 0.000 description 1
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Abstract
The invention discloses a purification and desalination method for a chromogen. (1) Taking D-xylose as a raw material, carrying out condensation reaction with acetylacetone in an alkaline solution, and simultaneously hydrolyzing and decarboxylating to obtain an intermediate 1-C- (beta-D-xylopyranosyl) -acetone; (2) Reducing, quenching, filtering and concentrating the intermediate obtained in the step (1) to obtain a crude product of the boscalid; (3) Diluting the crude product of the vitronectin obtained in the step (2) with water, purifying and desalting the crude product by an organic membrane filtration system, controlling the molecular weight cutoff of the organic membrane to be 75 daltons, feeding the product under the pressure of the filtration system of 0.3MPa, and stopping the machine when the pressure of the system rises to 1.5 MPa; then concentrated to obtain the vitronectin. The method has the advantages of simple operation, high desalting efficiency and less waste water output, and is suitable for industrial production.
Description
Technical Field
The invention relates to the field of purification and desalination of vitreous chromogens, in particular to a method for chemically synthesizing the purification and desalination of vitreous chromogens.
Background
Boseine, full name (2S, 3R, 4S, 5R) -2- (2-hydroxypropyl) tetrahydro-2H-pyran-3, 4, 5-triol, abbreviated as hydroxypropyl tetrahydropyran triol (CAS: 439685-79-7). Boseine is a xylose derivative with anti-aging activity, and can promote the synthesis of collagen, make skin more tough and elastic, improve neck fine lines, and prevent aging.
The synthesis of hydroxypropyl tetrahydropyrane triol requires two steps, the first step is the synthesis of an intermediate from xylose and acetylacetone under alkaline conditions, and acetic acid is a by-product in this process. This is followed by a one-step classical reduction of organic chemistry. Complete removal of the acetate produced by the reaction is difficult, but the better the product is cleaned, the less odor is.
At present, anion and cation exchange columns are mostly adopted in the synthesis wave color on the market due to a purification desalting method, the column passing efficiency is low repeatedly during the purification desalting, the vitreous color adsorbed on an ion column cannot be washed completely due to the fact that a large amount of purified water is used for washing, the yield is low, a large amount of time is needed for concentrating the washed water, and the time, the labor and the production cost are increased. Since the vitreous color is sensitive to heat, the long-term concentration also increases the generation of impurities, thereby affecting the product quality. Thus, a method for purifying and desalting the color factor is provided.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a purification and desalination method for a chromogen.
In order to achieve the purpose, the technical scheme of the invention is as follows:
a method for purifying and desalting chromogens, comprising:
(1) Taking D-xylose as a raw material, carrying out condensation reaction with acetylacetone in an alkaline solution, and simultaneously hydrolyzing and decarboxylating to obtain an intermediate 1-C- (beta-D-xylopyranosyl) -acetone; the reaction formula is as follows
(2) Reducing, quenching, filtering and concentrating the intermediate obtained in the step (1) to obtain a crude product of the boscalid; the reaction formula is as follows:
(3) Diluting the crude product of the vitronectin obtained in the step (2) with water, purifying and desalting the crude product by an organic membrane filtration system, controlling the molecular weight cutoff of the organic membrane to be 75 daltons, feeding the product under the pressure of the filtration system of 0.3MPa, and stopping the machine when the pressure of the system rises to 1.5 MPa; then concentrated to obtain the vitronectin.
The using amount of the crude vitronectin dilution water in the step (3) is 5 to 20 times, preferably 10 to 12 times of that of the crude vitronectin.
The conductivity of the crude product of the wave color factor in the step (3) after being diluted by water is 3000 to 15000 mu s/cm, and is preferably 5000 to 10000 mu s/cm.
And (3) refluxing flow of crude product purification desalting of the pink pigment in the step (3) is 300 to 600ml/h.
And (3) the effluent flow rate of the crude product purification and desalting in the step (3) is 200 to 300ml/h.
And (3) after the crude product is purified and desalted, the conductivity of the crude product in the step (3) is 2 to 10 mu s/cm.
And (3) purifying and desalting the crude product of the color factor in the step (3) to obtain the product with the content of 40 to 60wt%.
Compared with the prior purification and desalination technology, the method has the advantages of simple operation, high desalination efficiency and less wastewater output, and is suitable for industrial production.
Drawings
FIG. 1 is a liquid phase diagram of a vitronectin intermediate prepared in example 1.
FIG. 2 is a liquid phase chromatogram of the chromogen prepared in example 1.
Detailed Description
The following describes embodiments of the present invention in detail. The following examples are illustrative only and are not to be construed as limiting the invention.
Example 1
(1) Synthesis of chromogen intermediate
Adding 100g of D-xylose and 500g of purified water into a 2000ml reaction bottle, stirring for dissolving, cooling to 0-10 ℃, dropwise adding 540g of 7.5% sodium hydroxide solution, heating to 50-60 ℃, keeping the temperature for reaction for 4 hours, cooling, adjusting the pH value to be neutral by hydrochloric acid, and concentrating to dryness to obtain 210g of a brown oily substance wave color factor intermediate (containing salt).
(2) Crude synthesis of chromogen
Adding 500g of absolute ethyl alcohol into a 2000ml reaction bottle, adding 30g of sodium borohydride, replacing with nitrogen, cooling to 0-5 ℃, controlling the temperature to be not higher than 15 ℃, dropwise adding 510g of vitronectin intermediate ethanol solution (210 g of chromogen intermediate +300g of absolute ethyl alcohol), carrying out heat preservation reaction at 20-30 ℃ for 4h, cooling, dropwise adding 3% hydrochloric acid to carry out quenching reaction to adjust the pH to be 7-8, filtering, drying, adding 100g of absolute ethyl alcohol to dissolve, filtering to remove salt, and drying to obtain 120g of brown vitronectin crude product (containing salt).
(3) Purification of vitriol by desalting
1200g of purified water is added into 120g of crude bosity factor, the mixture is stirred and dissolved at normal temperature, the measured conductivity is 9.31ms/cm, the solution of the crude bosity factor is filtered by an organic membrane filtration system (the molecular weight of the organic membrane is 75 daltons), the system pressure is controlled to be 0.3MPa, the feeding is carried out, the reflux flow is 300 to 600ml/h, the effluent flow is 200 to 300ml/h, the system is stopped when the system pressure is increased to 1.5MPa, the purified bosity factor is detected, the conductivity is 4 mus/cm, the content is 57.2%, the content of the bosity factor detected by a filtrate is 0.04%, the conductivity is 23.32ms/cm, the aqueous solution of the bosity factor after the purification and the salt removal is 150g, and the mixture is concentrated to obtain 86g of light yellow bosity factor, the total yield is 63%, and the purity is 96.9%.
Example 2
(1) Synthesis of chromogen intermediate
Adding 200g of D-xylose and 1000g of purified water into a 5000ml reaction bottle, stirring, dissolving, cooling to 0-10 ℃, dropwise adding 980g of 7.5% sodium hydroxide solution, heating to 50-60 ℃, preserving heat, reacting for 4 hours, cooling, adjusting the pH value to be neutral by hydrochloric acid, and concentrating to dryness to obtain 430g (containing salt) of a brown oily substance wave color factor intermediate.
(2) Crude synthesis of chromogen
Adding 1000g of absolute ethyl alcohol into a 5000ml reaction bottle, adding 60g of sodium borohydride, replacing with nitrogen, cooling to 0-5 ℃, controlling the temperature to be not higher than 15 ℃, dropwise adding 1030g of vitronectin intermediate ethanol solution (430 g of chromogen intermediate +600g of absolute ethyl alcohol), carrying out heat preservation reaction at 20-30 ℃ for 4h, cooling, dropwise adding 3% hydrochloric acid to carry out quenching reaction to adjust the pH to be 7-8, filtering, drying, adding 200g of absolute ethyl alcohol to dissolve, filtering to remove salt, and drying to obtain 246g of brown vitronectin crude product (containing salt).
(3) Purification of vitriol by desalting
4920g of purified water is added into 246g of crude bosity factor, the mixture is stirred and dissolved at normal temperature, the measured conductivity is 4.36ms/cm, the crude bosity factor solution passes through an organic membrane filtration system (the molecular weight of the organic membrane is 75 daltons), the system pressure is controlled to be 0.3MPa, the feeding is carried out, the reflux flow is 300 to 600ml/h, the effluent flow is 200 to 300ml/h, when the system pressure is increased to 1.5MPa, the machine is stopped, the purified bosity factor is detected, the conductivity is 3.6 mus/cm, the content is 55.4%, the content of the bosity factor detected in the filtrate is 0.06%, the conductivity is 1.36ms/cm, the aqueous solution of the bosity factor after purification and salt removal is 322g, 178g of light yellow bosity factor is obtained by concentration, the total yield is 60.9%, and the purity: 96.4 percent.
Comparative example 1 purification of chromogen to remove salt
Adding 1000g of purified water into 100g of crude bosity factor, stirring and dissolving at normal temperature, measuring the conductivity to be 9.5ms/cm, enabling a solution of the crude bosity factor to pass through an organic membrane filtration system (the molecular weight of the organic membrane is 150 daltons), controlling the system pressure to be 0.3MPa, feeding, controlling the reflux flow to be 300-600ml/h, discharging the solution at 200-300ml/h, stopping the system when the system pressure is raised to 1.5MPa, detecting the purified bosity factor, wherein the conductivity is 5.2 mus/cm, the content is 27.6%, detecting the content of the bosity factor in the filtrate to be 26.3%, the conductivity is 22.3ms/cm, purifying and desalting to obtain 148g of aqueous solution of the bosity factor, and concentrating to obtain 41g of light yellow bosity factor. Organic membranes with a molecular weight cutoff of 150 daltons remove salt, but the color factor also permeates, affecting the yield.
Comparative example 2 purification of chromogen to remove salt
Adding 1000g of purified water into 100g of crude bosity factor, stirring and dissolving at normal temperature, measuring the conductivity to be 9836 mu s/cm, enabling a crude bosity factor solution to pass through an organic membrane filtration system (the molecular weight of the organic membrane cut-off is 50 daltons), controlling the system pressure to be 0.3MPa, feeding, controlling the reflux flow to be 300-600ml/h, discharging the solution at the flow of 200-300ml/h, stopping the system when the system pressure is raised to 1.5MPa, detecting the purified bosity factor, wherein the conductivity is 66.2ms/cm, the content is 56.1%, and detecting the content of the bosity factor in the filtrate to be 0.03% and the conductivity to be 5.3 mu s/cm. The organic membrane with the molecular weight cutoff of 50 daltons can not remove salt basically, and can not achieve the purpose of purification.
While embodiments of the present invention have been shown and described, it will be understood that the embodiments described above are illustrative and not to be construed as limiting the invention, and that various changes and modifications may be effected therein by one skilled in the art without departing from the spirit and scope of the invention.
Claims (7)
1. The method for purifying and desalting the vitreous chromogen is characterized by comprising the following steps of:
(1) Taking D-xylose as a raw material, carrying out condensation reaction with acetylacetone in an alkaline solution, and simultaneously hydrolyzing and decarboxylating to obtain an intermediate 1-C- (beta-D-xylopyranosyl) -acetone;
(2) Reducing, quenching, filtering and concentrating the intermediate obtained in the step (1) to obtain a crude product of the boscalid;
(3) Diluting the crude product of the vitronectin obtained in the step (2) with water, purifying and desalting the crude product by an organic membrane filtration system, controlling the molecular weight cutoff of the organic membrane to be 75 daltons, feeding the product under the pressure of the filtration system of 0.3MPa, and stopping the machine when the pressure of the system rises to 1.5 MPa; then concentrated to obtain the vitronectin.
2. The method for purifying and desalting the chromogen according to claim 1, wherein the amount of the diluting water for the crude product of the chromogen is 5 to 20 times that of the crude product of the chromogen.
3. The method for purifying and desalting the chromogen according to claim 1, wherein the conductivity of the crude chromogen product diluted with water is 5000 to 10000 μ s/cm.
4. The method for purifying and desalting a chromogen according to claim 1: the method is characterized in that the reflux flow rate of crude purification desalting of the trichromatism is 300 to 600ml/h.
5. The method of claim 4 for purifying and desalting a chromogen: the method is characterized in that the flow rate of the effluent liquid for purifying and desalting the crude product of the color factor is 200 to 300ml/h.
6. The method of purifying and desalting for a chromogen according to claim 1: the method is characterized in that the conductivity of the crude product of the wave color factor after purification and desalting is 2 to 10 mu s/cm.
7. The method of purifying and desalting for a chromogen according to claim 1: the method is characterized in that the content of the crude product of the wave color factor after purification and desalination is 40 to 60wt%.
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| CN117050045A (en) * | 2023-10-10 | 2023-11-14 | 长沙创新药物工业技术研究院有限公司 | Synthesis method of S-configuration hydroxypropyl tetrahydropyran triol |
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