CN117285578A - Preparation method of mannitol and erythritol - Google Patents
Preparation method of mannitol and erythritol Download PDFInfo
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- CN117285578A CN117285578A CN202311219206.9A CN202311219206A CN117285578A CN 117285578 A CN117285578 A CN 117285578A CN 202311219206 A CN202311219206 A CN 202311219206A CN 117285578 A CN117285578 A CN 117285578A
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- erythritol
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- 229930195725 Mannitol Natural products 0.000 title claims abstract description 66
- 239000000594 mannitol Substances 0.000 title claims abstract description 66
- 235000010355 mannitol Nutrition 0.000 title claims abstract description 66
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 title claims abstract description 54
- 239000004386 Erythritol Substances 0.000 title claims abstract description 46
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 title claims abstract description 46
- 235000019414 erythritol Nutrition 0.000 title claims abstract description 46
- 229940009714 erythritol Drugs 0.000 title claims abstract description 46
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 title claims abstract description 32
- 238000002360 preparation method Methods 0.000 title abstract description 11
- -1 mannitol erythritol lipid Chemical class 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000004440 column chromatography Methods 0.000 claims abstract description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000000741 silica gel Substances 0.000 claims abstract description 5
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 5
- 241001661343 Moesziomyces aphidis Species 0.000 claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 114
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 51
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 17
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical group CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 12
- 239000003480 eluent Substances 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 238000000926 separation method Methods 0.000 claims description 9
- 238000004809 thin layer chromatography Methods 0.000 claims description 9
- 230000005526 G1 to G0 transition Effects 0.000 claims description 8
- 230000007935 neutral effect Effects 0.000 claims description 8
- 239000000047 product Substances 0.000 claims description 8
- 238000000746 purification Methods 0.000 claims description 8
- 239000012535 impurity Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- 230000001105 regulatory effect Effects 0.000 claims description 6
- 239000012141 concentrate Substances 0.000 claims description 5
- 238000009777 vacuum freeze-drying Methods 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000012043 crude product Substances 0.000 claims description 4
- 238000000855 fermentation Methods 0.000 claims description 4
- 230000004151 fermentation Effects 0.000 claims description 4
- 239000004519 grease Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- UJEADPSEBDCWPS-SGJODSJKSA-N (2R,3R)-1-[(3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]butane-1,2,3,4-tetrol Chemical class C1([C@@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)C([C@H](O)[C@H](O)CO)O UJEADPSEBDCWPS-SGJODSJKSA-N 0.000 abstract description 25
- 150000005846 sugar alcohols Chemical class 0.000 abstract description 14
- 150000002016 disaccharides Chemical class 0.000 abstract description 4
- 125000005313 fatty acid group Chemical group 0.000 abstract description 4
- 238000005904 alkaline hydrolysis reaction Methods 0.000 abstract description 3
- 235000013305 food Nutrition 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 241001124076 Aphididae Species 0.000 abstract description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 229940079593 drug Drugs 0.000 abstract description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000006072 paste Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 235000000346 sugar Nutrition 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 208000002925 dental caries Diseases 0.000 description 3
- 206010012601 diabetes mellitus Diseases 0.000 description 3
- 235000003599 food sweetener Nutrition 0.000 description 3
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000003765 sweetening agent Substances 0.000 description 3
- 239000000811 xylitol Substances 0.000 description 3
- 235000010447 xylitol Nutrition 0.000 description 3
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 3
- 229960002675 xylitol Drugs 0.000 description 3
- MYKOKMFESWKQRX-UHFFFAOYSA-N 10h-anthracen-9-one;sulfuric acid Chemical compound OS(O)(=O)=O.C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 MYKOKMFESWKQRX-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- 208000008589 Obesity Diseases 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
- 235000020824 obesity Nutrition 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 235000010356 sorbitol Nutrition 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 206010048962 Brain oedema Diseases 0.000 description 1
- 206010010774 Constipation Diseases 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 208000018522 Gastrointestinal disease Diseases 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- 102000004877 Insulin Human genes 0.000 description 1
- 108090001061 Insulin Proteins 0.000 description 1
- 230000003178 anti-diabetic effect Effects 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000015895 biscuits Nutrition 0.000 description 1
- 239000004067 bulking agent Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229940125396 insulin Drugs 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 235000013615 non-nutritive sweetener Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method of mannitol erythritol, and belongs to the field of sugar alcohols. Mannitol is prepared by taking mannitol erythritol lipid (mannosylerythritol lipids, MELs) obtained by fermenting aphid mimicry yeast (Pseudozyma aphidis) as a raw material, and removing acetyl and fatty acid chains in the MELs through alkaline hydrolysis reaction. And then separating and purifying by silica gel or activated carbon column chromatography to obtain the mannitol erythritol. The mannitol erythritol prepared by the method is a novel disaccharide alcohol and has wide application potential in the fields of food, daily chemicals, medicines and the like.
Description
Technical Field
The invention relates to the technical field of disaccharide alcohol preparation, in particular to a preparation method of mannitol and erythritol.
Background
Sugar alcohol is a polyhydric alcohol and has wide application in the fields of food, daily chemicals, medicines and the like. Sugar alcohols, although not sugar, have some of the attributes of sugar, both less sweet than sucrose and also much less caloric than sucrose, and thus are useful as low-sweetness, low-caloric sweeteners or bulking agents for high-sweetness sweeteners for the manufacture of low-caloric or sugarless foods, such as sorbitol, xylitol, mannitol, and the like, commonly used in the manufacture of confections, chewing gums, biscuits. Meanwhile, sugar alcohol is generally not limited by insulin and does not cause the rise of blood sugar level, so the sugar alcohol is commonly used as sweetener for patients with diabetes and obesity. In oral care, sugar alcohol is not affected by microorganisms, does not produce acid and does not lower the pH in the oral cavity, so that the oral care product has no caries and is often applied to oral care products such as toothpaste and the like. Sugar alcohols are also widely used in the medical field, for example mannitol is used for the treatment of cerebral oedema and intravenous solutions; sorbitol can be used for treating constipation and gastrointestinal diseases; xylitol can be used for preparing granule for oral administration. Among them, xylitol and erythritol are evaluated as potential antidiabetic sweeteners in many studies reports, with therapeutic potential for diabetes and its complications. Along with the increasingly prominent problems of modern diabetes, obesity, hyperlipidemia, dental caries and the like, various sugar alcohols which have high safety, good taste, no dental caries and no influence on blood sugar level are increasingly valued by people.
Most sugar alcohols are produced by catalytic hydrogenation of their corresponding sugars, and at present sugar alcohols are not available in many types, and Mannosylerythritol (ME) has the chemical name 4-O- β -D-mannopyranosyl-meso-erythritol, a sugar alcohol composed of mannose and erythritol, which is not found naturally in plants and the like, and thus the means of acquisition is very poor.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a preparation method of mannitol and erythritol.
The aim of the invention is realized by the following technical scheme:
in a first aspect, the present invention provides a method for preparing mannitol, the method comprising the steps of:
dissolving mannitol erythritol lipid in methanol solvent, wherein the concentration of the mannitol erythritol lipid is 20-80g/L, then regulating the pH to 13 or above, and reacting at room temperature for 10-60min to obtain a methanol solution containing mannitol;
(2) Regulating the pH of the methanol solution containing mannitol to 6.8-7.0 to obtain neutral methanol solution containing mannitol;
(3) Concentrating the methanol solution containing the mannose erythritol to obtain mannose erythritol concentrated solution;
(4) Performing column chromatography separation and purification on the mannitol erythritol concentrated solution, and collecting only eluent with a specific shift value of 0.25 on a thin layer chromatography plate;
(5) Drying the eluent to obtain the pure product of the mannitol erythritol.
Further, the mannose erythritol lipid is a crude product obtained by separating Pseudozyma aphidis fermentation liquor.
Further, the concentration of the mannosyl erythritol lipid is 20-80g/L.
Further, the step (1) includes: sodium hydroxide of 0.5mol/L is added, the pH is adjusted to 13 or above, and the mixture is reacted for 30min at room temperature.
Further, the step (2) includes: dilute sulfuric acid with a concentration of 1.83M is added, and the pH of the methanol solution containing mannitol is adjusted to 6.8-7.0.
Further, the main impurities of the mannitol erythritol concentrate are grease and mannose.
Further, the step (4) of separating and purifying the mannitol concentrate by column chromatography comprises the following steps:
the stationary phase is 200 mesh silica gel, and the mobile phase is n-butanol: isopropyl alcohol: water = 7:5:2;
or alternatively, the first and second heat exchangers may be,
the stationary phase is 200 mesh active carbon and diatomite with a mass ratio of 1:1, and the mobile phase is ethanol solution with a volume fraction of 0% -20%.
Further, the eluent dried in the step (5) is dried by a vacuum freeze drying method.
In a second aspect, the invention provides mannitol, prepared by the method for preparing mannitol.
The beneficial effects of the invention are as follows: the invention starts from crude products of natural fermentation products of mannitol erythritol lipid MELs, removes acetyl and fatty acid chains in the MELs through alkaline hydrolysis reaction to prepare deacylated ME, and can efficiently separate and purify mannitol ME by a one-step column chromatography separation method, thereby providing a new type of sugar alcohol and a preparation method thereof.
Drawings
In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings that are needed in the description of the embodiments will be briefly described below, it being obvious that the drawings in the following description are only some embodiments of the present invention, and that other drawings may be obtained according to these drawings without inventive effort to a person skilled in the art.
FIG. 1 is a schematic diagram of the process for the preparation, isolation and purification of mannitol.
Detailed Description
The following description of the embodiments of the present invention will be made clearly and completely with reference to the accompanying drawings, in which it is apparent that the embodiments described are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
The features of the following examples and embodiments may be combined with each other without any conflict.
As shown in fig. 1, the invention provides a preparation method of mannitol, which comprises the following steps:
(1) Dissolving mannitol erythritol lipid in methanol solvent, wherein the concentration of the mannitol erythritol lipid is 20-80g/L, then regulating the pH to 13 or above, and reacting at room temperature for 10-60min to obtain a methanol solution containing mannitol; acetyl and fatty acid chains in mannitol erythritol lipid MELs are removed through alkaline hydrolysis reaction.
The mannose erythritol lipid (mannosylerythritol lipids, MELs) is a crude product obtained by separating a fermentation liquid of aphid mimicry yeast (Pseudozyma aphidis).
Further, it is preferable to add 0.5mol/L sodium hydroxide, adjust the pH of the methanol solution containing mannitol erythritol to 13 or more, and react at room temperature for 30 minutes.
(2) Adding 1.83M dilute sulfuric acid, and adjusting the pH of the methanol solution containing mannitol to 6.8-7.0 to obtain neutral methanol solution containing mannitol.
(3) Concentrating the methanol solution containing the mannose erythritol to obtain mannose erythritol concentrated solution; the main impurities of the mannitol erythritol concentrate are grease and mannose.
(4) And (3) performing column chromatography separation and purification on the mannitol erythritol concentrated solution, and collecting only eluent with a specific shift value of 0.25 on a thin layer chromatography plate.
The column chromatography separation and purification comprises the following steps:
the stationary phase adopts 200 mesh silica gel, and the mobile phase adopts volume ratio of 7:5:2 n-butanol: isopropyl alcohol: water;
or alternatively, the first and second heat exchangers may be,
the stationary phase adopts 200 mesh active carbon and diatomite with the mass ratio of 1:1, and the mobile phase adopts ethanol solution with the volume fraction of 0% -20%.
(5) And (5) performing vacuum freeze drying on the eluent to obtain a pure product of the mannitol erythritol.
Example 1
2.4g of crude MELs paste was dissolved in 20mL of methanol and the volume was set to 30mL to achieve a crude MELs methanol solution concentration of 80g/L. NaOH solid is added into the mixture to make the concentration of NaOH be 0.5-2.5M, and the mixture is reacted for 10-60min at room temperature. The structural change of the product and impurities was observed by Thin Layer Chromatography (TLC). The above-mentioned added NaOH solid makes the pH of the methanol solution to be 13.0 or more, and the alkaline environment breaks acyl bonds of MELs, which lose acetyl groups and fatty acid chains, thereby obtaining ME.
The reaction speed depends on pH, the pH depends on NaOH concentration, and NaOH can finish the reaction within 10-60min at the concentration of 0.5M-2.5M, and the conversion rate is close to 100%. The time required to complete the reaction was gradually reduced as the amount of alkali added was increased, and the reaction time and conversion were as shown in table 1. .
Table 1: relationship table of NaOH concentration, reaction time and MELs conversion
The results show that: the optimal condition for the alkaline reaction of crude MELs is a NaOH concentration of 0.5M and a reaction time of 30min, which allows nearly 100% conversion of MELs to mannitol ME.
Example 2
2.4g of crude MELs paste was dissolved in 20mL of methanol and the volume was set to 30mL to achieve a crude MELs methanol solution concentration of 80g/L. To this was added NaOH solid to make NaOH concentration 0.5M, and reacted at room temperature for 30min to obtain ME methanol solution. The pH of the obtained ME methanol solution is regulated to 6.8-7.0 by using acid to prepare the neutral ME methanol solution.
The pH-adjusting acid may be concentrated sulfuric acid, 1.83M dilute sulfuric acid, concentrated hydrochloric acid or 4M dilute hydrochloric acid, but the use of concentrated acid may decompose ME into mannose and erythritol, and the presence of hydrophilic impurities may cause difficulty in separation and purification, so that the choice of dilute acid is more preferable. However, dilute hydrochloric acid will form NaCl with NaOH, which is better soluble in water, thereby increasing the presence of impurity salts, so that the pH is most preferably adjusted to 1.83M dilute sulfuric acid.
The results show that: after the optimal alkali reaction, the pH is adjusted to be the optimal scheme by selecting 1.83M dilute sulfuric acid, so that the mannitol and erythritol ME after the alkali reaction have almost no loss.
Example 3
2.4g of crude MELs paste was dissolved in 20mL of methanol and the volume was set to 30mL to achieve a crude MELs methanol solution concentration of 80g/L. To this was added NaOH solid to make NaOH concentration 0.5M, and reacted at room temperature for 30min to obtain ME methanol solution. The pH of the obtained ME methanol solution is adjusted to 6.8-7.0 by using 1.83M dilute sulfuric acid to prepare the neutral ME methanol solution.
30mL of neutral ME methanol solution is subjected to 40 ℃ and-0.1 MPa rotary evaporation to obtain a paste, the paste is diluted to 2mL by using water, a chromatographic column 305X 46mm is selected, a stationary phase is selected from 200-mesh silica gel, and a mobile phase is selected from n-butanol: isopropyl alcohol: water = 7:5:2. the composition change of the eluent was followed using thin layer chromatography, n-butanol was selected for thin layer chromatography developing agent: isopropyl alcohol: water = 7:5:2, the color reagent is selected from 0.2% sulfuric acid-anthrone, and the eluent with the specific shift value of 0.25 is collected.
The collected eluate was concentrated using vacuum freeze-drying, and the final purity of mannitol erythritol ME was nearly 100%, and the recovery rate was 71.4%.
Example 4
2.4g of crude MELs paste was dissolved in 20mL of methanol and the volume was set to 30mL to achieve a crude MELs methanol solution concentration of 80g/L. To this was added NaOH solid to make NaOH concentration 0.5M, and reacted at room temperature for 30min to obtain ME methanol solution. The pH of the obtained ME methanol solution is adjusted to 6.8-7.0 by using 1.83M dilute sulfuric acid to prepare the neutral ME methanol solution.
30mL of neutral ME methanol solution is subjected to 40 ℃ and-0.1 MPa rotary evaporation and concentration to form a paste, the paste is diluted to 2mL by using water, a chromatographic column 305X 32mm is selected, and a stationary phase is selected from 200-mesh active carbon and diatomite 1:1, mobile phase selection ethanol: water = 0:100-20:80 gradient elution. The composition change of the eluent was followed using thin layer chromatography, n-butanol was selected for thin layer chromatography developing agent: isopropyl alcohol: water = 7:5:2, the color reagent is selected from 0.2% sulfuric acid-anthrone, and the eluent with the specific shift value of 0.25 is collected.
The collected eluate was concentrated using vacuum freeze-drying, and the final purity of mannitol erythritol ME was nearly 100%, with a recovery rate of 84.0%.
In summary, the invention develops a novel preparation and separation and purification method of the disaccharide alcohol ME, the alkali reaction is simple to operate, the required time is short, the column chromatography uses safer organic solvents, and mannitol with the purity of nearly 100% can be rapidly separated. After the alkali reaction, the impurities mainly comprise grease and mannose, and other purification steps are not needed to be added because a column chromatography separation method is selected later, so that the pure product of the mannitol erythritol ME is obtained through one-step separation. The invention starts from natural product mannitol erythritol lipid MELs, prepares new disaccharide alcohol by chemical reaction, provides a new preparation scheme, and provides more types for sugar alcohol.
The foregoing is merely a preferred example of the present invention and is not intended to limit the scope of the present invention. In addition to the embodiments described above, other embodiments of the invention are possible. All technical schemes formed by adopting equivalent replacement or equivalent variation fall within the protection scope of the invention.
Claims (9)
1. A method for preparing mannitol, comprising the steps of:
(1) Dissolving mannitol erythritol lipid in methanol solvent, wherein the concentration of the mannitol erythritol lipid is 20-80g/L, then regulating the pH to 13 or above, and reacting at room temperature for 10-60min to obtain a methanol solution containing mannitol;
(2) Regulating the pH of the methanol solution containing mannitol to 6.8-7.0 to obtain neutral methanol solution containing mannitol;
(3) Concentrating the methanol solution containing the mannose erythritol to obtain mannose erythritol concentrated solution;
(4) Performing column chromatography separation and purification on the mannitol erythritol concentrated solution, and collecting only eluent with a specific shift value of 0.25 on a thin layer chromatography plate;
(5) Drying the eluent to obtain the pure product of the mannitol erythritol.
2. The method for preparing mannitol according to claim 1, wherein the mannitol erythritol lipid is a crude product obtained by separating Pseudozyma aphidis fermentation broth.
3. The method for producing mannitol according to claim 1, wherein the concentration of mannitol erythritol lipid is 20-80g/L.
4. The method for preparing mannitol according to claim 1, wherein the step (1) comprises: sodium hydroxide of 0.5mol/L is added, the pH is adjusted to 13 or above, and the mixture is reacted for 30min at room temperature.
5. The method for producing mannitol according to claim 1, wherein the step (2) comprises: dilute sulfuric acid with a concentration of 1.83M is added, and the pH of the methanol solution containing mannitol is adjusted to 6.8-7.0.
6. The method for preparing mannitol and erythritol according to claim 1, wherein the main impurities of the mannitol and erythritol concentrate are grease and mannose.
7. The method for preparing mannitol and erythritol according to claim 1, wherein the step (4) of separating and purifying the mannitol concentrate by column chromatography comprises:
the stationary phase is 200 mesh silica gel, and the mobile phase is n-butanol: isopropyl alcohol: water = 7:5:2;
or alternatively, the first and second heat exchangers may be,
the stationary phase is 200 mesh active carbon and diatomite with a mass ratio of 1:1, and the mobile phase is ethanol solution with a volume fraction of 0% -20%.
8. The method for preparing mannitol according to claim 1, wherein the drying eluent in step (5) is vacuum freeze drying.
9. Mannitol, characterized in that it is produced by a process according to any one of claims 1 to 8.
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