CN115746009B - Method for fractionating sugar alcohol and dehydrated derivative thereof through hydrophobic ionic liquid - Google Patents
Method for fractionating sugar alcohol and dehydrated derivative thereof through hydrophobic ionic liquid Download PDFInfo
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- 150000005846 sugar alcohols Chemical class 0.000 title claims abstract description 44
- 239000002608 ionic liquid Substances 0.000 title claims abstract description 33
- 230000002209 hydrophobic effect Effects 0.000 title claims abstract description 21
- 238000000034 method Methods 0.000 title claims abstract description 17
- 239000003960 organic solvent Substances 0.000 claims abstract description 20
- 239000000706 filtrate Substances 0.000 claims abstract description 17
- 239000007864 aqueous solution Substances 0.000 claims abstract description 13
- 238000002390 rotary evaporation Methods 0.000 claims abstract description 9
- 238000004090 dissolution Methods 0.000 claims abstract description 7
- 238000000967 suction filtration Methods 0.000 claims abstract description 3
- 229960002479 isosorbide Drugs 0.000 claims description 25
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 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 claims description 17
- 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 claims description 15
- 239000000243 solution Substances 0.000 claims description 15
- 239000000600 sorbitol Substances 0.000 claims description 15
- 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 claims description 11
- -1 imidazole cation Chemical class 0.000 claims description 11
- KLDXJTOLSGUMSJ-BXKVDMCESA-N (3s,3as,6s,6as)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3,6-diol Chemical compound O[C@H]1CO[C@H]2[C@@H](O)CO[C@H]21 KLDXJTOLSGUMSJ-BXKVDMCESA-N 0.000 claims description 8
- 229930195725 Mannitol Natural products 0.000 claims description 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 8
- 239000000594 mannitol Substances 0.000 claims description 8
- 235000010355 mannitol Nutrition 0.000 claims description 8
- 150000001450 anions Chemical class 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 4
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 125000003158 alcohol group Chemical group 0.000 claims description 2
- NJMWOUFKYKNWDW-UHFFFAOYSA-N 1-ethyl-3-methylimidazolium Chemical compound CCN1C=C[N+](C)=C1 NJMWOUFKYKNWDW-UHFFFAOYSA-N 0.000 claims 1
- 239000008346 aqueous phase Substances 0.000 abstract description 13
- 239000000047 product Substances 0.000 abstract description 10
- 238000005194 fractionation Methods 0.000 abstract description 7
- 238000005265 energy consumption Methods 0.000 abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 66
- 238000004128 high performance liquid chromatography Methods 0.000 description 17
- 238000010438 heat treatment Methods 0.000 description 15
- 235000010356 sorbitol Nutrition 0.000 description 14
- 238000002156 mixing Methods 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 238000001914 filtration Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000011521 glass Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000000725 suspension Substances 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 2
- PKAUICCNAWQPAU-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)acetic acid;n-methylmethanamine Chemical compound CNC.CC1=CC(Cl)=CC=C1OCC(O)=O PKAUICCNAWQPAU-UHFFFAOYSA-N 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- 229910018286 SbF 6 Inorganic materials 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910001412 inorganic anion Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000845 maltitol Substances 0.000 description 1
- 235000010449 maltitol Nutrition 0.000 description 1
- VQHSOMBJVWLPSR-WUJBLJFYSA-N maltitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-WUJBLJFYSA-N 0.000 description 1
- 229940035436 maltitol Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 150000002891 organic anions Chemical class 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical group [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Abstract
The invention relates to a method for fractionating sugar alcohol and dehydrated derivatives thereof by hydrophobic ionic liquid, wherein the sugar alcohol and dehydrated derivatives thereof are added into the hydrophobic ionic liquid for dissolution, and the filtrate mainly containing the dehydrated derivatives of the sugar alcohol is obtained by suction filtration; adding aqueous solution of organic solvent into the filtrate, removing the organic solvent by rotary evaporation, and separating to obtain aqueous phase containing dehydrated derivative of sugar alcohol. Compared with the prior art, the hydrophobic ionic liquid used in the invention has very large difference on the solubility of sugar alcohol and dehydrated products thereof, in particular, dehydrated products capable of dissolving sugar alcohol in a large amount are almost insoluble sugar alcohol. The invention can fractionate sugar alcohol and dehydrated derivatives thereof under the conditions of lower temperature and shorter time, effectively reduces the energy consumption of fractionation and improves the fractionation efficiency.
Description
Technical Field
The invention belongs to the field of chemical separation, and relates to a method for fractionating sugar alcohol and dehydrated derivatives thereof by using hydrophobic ionic liquid.
Background
Sugar alcohols are compounds obtained when the aldehyde or ketone group of a sugar is reduced to the corresponding hydroxyl group. The ordinary sugar alcohol can be dehydrated to obtain a dehydrated sugar alcohol product with a high added value.
Sugar alcohols and their anhydrosugar alcohols are polyhydroxy compounds which are generally used as technical ingredients. Maltitol is a novel sweetener, widely used in sugar food processing. Sorbitol and mannitol are useful as chemical raw materials, commonly used in the food and pharmaceutical industries. The corresponding dehydrated products of isosorbide and isomannide are polyhydroxy sugar alcohol compounds widely applied in the market, are main components of corn oil and are byproducts of the starch industry. These compounds are mainly used in the polymer, cosmetic and pharmaceutical industries. Isosorbide and isomannide can be used to replace bisphenol a synthetic polymeric materials. Isosorbide and isomannide also have great potential for use in food and other fields.
All these sugar alcohols and their high added value anhydrosugar alcohols coexist in a mixture of products of natural origin or industrially produced, which may reduce their biological activity or technical properties. Unfortunately, the fractionation of sugar alcohols and their high value-added anhydrosugar alcohols is considered a challenging task due to the complexity and structural similarity of the mixtures. Fractionation can be performed by distillation using the difference in boiling points. Isosorbide and sorbitol are separated after long-term distillation at 170 ℃ (catalyst. Sci. Technology., 2017,7,2065-2073), but the distillation process consumes a lot of energy. For sustainable development, it is necessary to develop a greener and energy efficient process to fractionate sugar alcohols and their dehydrated derivatives.
The ionic liquid makes it possible to fractionate sugar alcohol and its dewatered product in green and high efficiency. The ionic liquid is an ionic compound composed of organic cations and organic or inorganic anions, and has low volatility, low viscosity and high thermal stability. These characteristics make ionic liquids an environmentally friendly alternative solvent in many fields. The structure of the ionic liquid is adjustable. By changing the structure, the interaction between the ionic liquid and the polyhydroxy compound can be regulated, and the selective dissolution of the polyhydroxy compound is realized.
Disclosure of Invention
The invention aims to solve the technical problem that the energy consumption is high in the prior art for fractionating sugar alcohol and dehydrated products thereof by heating at high temperature, and provides a method for selectively dissolving and fractionating sugar alcohol and dehydrated products thereof by using hydrophobic ionic liquid, which solves the problem of high energy consumption and greatly improves the fractionating efficiency.
In order to solve the technical problems, the invention discloses a method for fractionating sugar alcohol and dehydrated derivatives thereof by using hydrophobic ionic liquid, wherein the sugar alcohol and dehydrated derivatives thereof are added into the hydrophobic ionic liquid for dissolution, and suction filtration is carried out to obtain filtrate mainly containing the dehydrated derivatives of the sugar alcohol; adding aqueous solution of organic solvent into the filtrate, removing the organic solvent by rotary evaporation, and separating to obtain aqueous phase containing dehydrated derivative of sugar alcohol.
Specifically, the hydrophobic ionic liquid consists of anions and cations.
Specifically, the anion is [ NTF 2 ] - 、[PF 6 ] - 、[SbF 6 ] - 、[BF 4 ] - Any one of them is preferably [ NTF ] 2 ] - The method comprises the steps of carrying out a first treatment on the surface of the The cation is any one of imidazole cation, pyridine cation, quaternary ammonium cation, quaternary phosphonium cation, guanidine cation, triazole cation, pyrrolidine cation, piperidine cation and morpholine cation, and is preferably imidazole cation.
Specifically, the sugar alcohol is sorbitol, mannitol or xylitol; the dehydrated derivative of sorbitol is isosorbide; the dehydrated derivative of mannitol is isomannide; the dehydrated derivative of xylitol is dehydrated xylitol.
Preferably, the sugar alcohol is sorbitol or mannitol; the dehydrated derivative of sorbitol is isosorbide; the dehydrated derivative of mannitol is isomannitol.
Specifically, the mass ratio of the sugar alcohol and the dehydrated derivative thereof to the hydrophobic ionic liquid is 0.1-0.3: 0.1 to 0.3:1.
specifically, the dissolution temperature is 25-60 ℃.
Specifically, the dissolution time is 1-4 h.
Specifically, the organic solvent is an alcohol organic solvent or a nitrile organic solvent.
Preferably, the alcohol organic solvent is methanol or ethanol; the nitrile organic solvent is acetonitrile.
More preferably, the alcohol-based organic solvent is ethanol.
Specifically, the volume ratio of the organic solvent to the water of the aqueous solution of the organic solvent is 1-3: 1, the volume ratio of the aqueous solution of the organic solvent to the filtrate is 5-40: 1.
wherein, the aqueous phase containing the dehydrated derivative of sugar alcohol is concentrated, and the concentrated solution after concentration is detected by HPLC, and the purity of the dehydrated derivative of sugar alcohol is 99.3-99.7%.
The HPLC detection method comprises the following steps: HPLC (Agilent 1260, USA) consisted of Bio-rad Aminex HPX-87H chromatography columns and a differential refractive index detector with a mobile phase of 0.5wt% aqueous sulfuric acid; the temperature of the column temperature box is 65 ℃ and the temperature of the differential detector is 50 ℃; the flow rate is 0.4mL/min; the acquisition time was 34min.
The beneficial effects are that:
(1) Compared with the prior art, the hydrophobic ionic liquid used in the invention has very large difference on the solubility of sugar alcohol and dehydrated products thereof, in particular, dehydrated products capable of dissolving sugar alcohol in a large amount are almost insoluble sugar alcohol.
(2) The invention can fractionate sugar alcohol and dehydrated derivatives thereof under the conditions of lower temperature and shorter time, effectively reduces the energy consumption of fractionation and improves the fractionation efficiency.
Drawings
The foregoing and/or other advantages of the invention will become more apparent from the following detailed description of the invention when taken in conjunction with the accompanying drawings and detailed description.
FIG. 1 shows high performance liquid chromatograms before and after sorbitol-isosorbide separation; wherein, FIG. 1a shows the HPLC analysis spectrum of the sorbitol-isosorbide mixture before separation, and FIG. 1b shows the HPLC analysis spectrum of the separated isosorbide.
FIG. 2 high performance liquid chromatograms of mannitol-isomannitol separation before and after separation; wherein, fig. 2a is a HPLC analysis spectrum of the mannitol-isomannide mixture before separation, and fig. 2b is a HPLC analysis spectrum of the isomannide separated.
Detailed Description
The present invention is described in the following examples, but the present invention is not limited to the following examples, and various modifications are included in the technical scope of the present invention without departing from the gist of the present invention.
Solubility determination: 0.4g of the sample was put into 1g of a hydrophobic ionic liquid at 45℃to obtain a suspension, and the suspension was stirred at 350rpm for 4 hours until a saturated solution was obtained; the suspension was then filtered in vacuo while hot using a funnel (2 um) to give a filtrate. To the filtrate, 10mL of ethanol and 10mL of deionized water were added to form a homogeneous solution. Removing ethanol from the obtained uniform solution by rotary evaporation (90 mbar) at 55deg.C for 15 min; separating the aqueous phase from the hydrophobic ionic liquid phase, collecting the upper aqueous phase containing polyhydroxy compound, and repeating the extraction 3 times to ensure complete extraction. The water was removed by rotary evaporation (90 mbar) at 65℃for 15min, the volume of the aqueous phase was reduced to 1/3 of the original volume and the content of the sample in the concentrated aqueous phase was analyzed by HPLC.
Example 1
Mixing sorbitol 0.1g, isosorbide 0.1g and [ Bmim ] 1g][NTF 2 ]Adding the mixture into a glass test tube reactor, heating to 60 ℃ in a heating module, dissolving for 4 hours, and filtering to obtain a solution while the solution is hot; then adding an aqueous solution of ethanol (10 mL of ethanol and 10mL of water, wherein the volume ratio of the ethanol to the water is 1:1) into the filtrate, mixing and stirring, then removing the ethanol by rotary evaporation at 55 ℃ and 90mbar for 15-20 min, removing ionic liquid by separating liquid, taking an upper aqueous phase, concentrating, detecting the content of sorbitol and isosorbide by using HPLC, and the HPLC analysis spectrogram is shown in figure 1. The purity of the obtained isosorbide was 99.7%.
Example 2
Mixing sorbitol 0.3g, isosorbide 0.3g, and [ Bmim ] 3g][NTF 2 ]Adding the mixture into a glass test tube reactor, heating to 25 ℃ in a heating module, dissolving for 1h, and filtering to obtain a solution while the solution is hot; subsequently, an aqueous solution of ethanol (30 mL of ethanol and 10mL of water, volume ratio of ethanol to water is 3:1) was added to the filtrate, mixed and stirred, then the mixture was distilled for 1 to 2 hours at 55 ℃ under 90mbar to remove the ethanol, then the ionic liquid was removed by separating liquid, the upper aqueous phase was taken, concentrated, and the sorbitol and isosorbide content was detected by HPLC. The purity of the obtained isosorbide is 99.5%.
Example 3
Mixing sorbitol 0.3g, isosorbide 0.3g and Emim 1g][NTF 2 ]Adding the mixture into a glass test tube reactor, heating to 45 ℃ in a heating module, dissolving for 4 hours, and filtering the solution while the solution is hot; then adding an aqueous solution of ethanol (10 mL of ethanol and 10mL of water, wherein the volume ratio of the ethanol to the water is 1:1) into the filtrate, mixing and stirring, then carrying out rotary evaporation for 15-20 min at 55 ℃ and 90mbar to remove the ethanol,removing ionic liquid by separating liquid, taking an upper water phase, concentrating, and detecting the content of sorbitol and isosorbide by using HPLC. The purity of the obtained isosorbide was 99.6%.
Example 4
Mixing sorbitol 0.3g, isosorbide 0.3g and Emim 1g][NTF 2 ]Adding the mixture into a glass test tube reactor, heating to 25 ℃ in a heating module, dissolving for 4 hours, and filtering to obtain a solution while the solution is hot; then adding an aqueous solution of ethanol (10 mL of ethanol and 10mL of water, wherein the volume ratio of the ethanol to the water is 1:1) into the filtrate, mixing and stirring, then spin-evaporating at 55 ℃ and 90mbar for 15-20 min to remove the ethanol, separating to remove ionic liquid, taking an upper aqueous phase, concentrating, and detecting the content of sorbitol and isosorbide by using HPLC. The purity of the obtained isosorbide was 99.4%.
Example 5
Mixing 0.3g sorbitol, 0.3g isosorbide, 1g [ ami ]][NTF 2 ]Adding the mixture into a glass test tube reactor, heating to 45 ℃ in a heating module, dissolving for 4 hours, and filtering the solution while the solution is hot; then adding an aqueous solution of ethanol (10 mL of ethanol and 10mL of water, wherein the volume ratio of the ethanol to the water is 1:1) into the filtrate, mixing and stirring, then spin-evaporating at 55 ℃ and 90mbar for 15-20 min to remove the ethanol, separating to remove ionic liquid, taking an upper aqueous phase, concentrating, and detecting the content of sorbitol and isosorbide by using HPLC. The purity of the obtained isosorbide was 99.6%.
Example 6
0.2g mannitol, 0.2g isomannitol, 1g [ ami ]][NTF 2 ]Adding into Shi Linke pipe, heating to 45deg.C in heating module, dissolving for 4 hr, and vacuum filtering to obtain solution; then adding an aqueous solution of ethanol (10 mL of ethanol and 10mL of water, wherein the volume ratio of the ethanol to the water is 1:1) into the filtrate, mixing and stirring, then performing rotary evaporation at 55 ℃ and 90mbar for 15-20 min to remove the ethanol, separating liquid to remove ionic liquid, taking an upper aqueous phase, concentrating, detecting the content of mannitol and isomannitol by using HPLC, and the HPLC analysis spectrogram is shown in figure 2. The purity of the obtained isomannide is 99.6%.
Example 7
0.2g mannitol, 0.2g isomannitol, 1g [ ami ]][NTF 2 ]Adding into Shi Linke pipe, heating to 25deg.C in heating module, dissolving for 4 hr, and vacuum filtering to obtain solution; then adding an aqueous solution of ethanol (2.5 mL of ethanol and 2.5mL of water, wherein the volume ratio of the ethanol to the water is 1:1) into the filtrate, mixing and stirring, then performing rotary evaporation at 55 ℃ and 90mbar for 15-20 min to remove the ethanol, separating liquid to remove ionic liquid, taking an upper aqueous phase, concentrating, and detecting the content of mannitol and isomannitol by using HPLC. The purity of the obtained isomannide is 99.3%.
TABLE 1 solubility of sugar alcohols and dehydrated derivatives thereof in hydrophobic ionic liquids
From Table 1, it can be seen that the hydrophobic ionic liquid hardly dissolves sugar alcohol but has a strong dissolving ability for dehydrated derivatives thereof, and fractionation of sugar alcohol and dehydrated derivatives can be achieved based on this particular property.
The invention provides a method for fractionating sugar alcohol and dehydrated derivatives thereof by using hydrophobic ionic liquid, and a method for realizing the technical scheme, wherein the method and the way are a plurality of preferred embodiments of the invention, and it should be pointed out that a plurality of improvements and modifications can be made by those skilled in the art without departing from the principle of the invention, and the improvements and modifications are also considered as the protection scope of the invention. The components not explicitly described in this embodiment can be implemented by using the prior art.
Claims (5)
1. A method for fractionating sugar alcohol and dehydrated derivatives thereof by using hydrophobic ionic liquid is characterized in that sugar alcohol and dehydrated derivatives thereof are added into the hydrophobic ionic liquid for dissolution, and suction filtration is carried out to obtain filtrate mainly containing dehydrated derivatives of sugar alcohol; adding an aqueous solution of an organic solvent into the filtrate, removing the organic solvent by rotary evaporation, and separating the solution to obtain a water phase containing dehydrated derivatives of sugar alcohol;
the hydrophobic ionic liquid consists of anions and cations;
the anion is [ NTF ] 2 ] - The method comprises the steps of carrying out a first treatment on the surface of the The cation is imidazole cation;
the imidazole cation is [ Bmim ]] + 、[Emim] + Or [ Amim ]] + ；
The sugar alcohol is sorbitol or mannitol; the dehydrated derivative of sorbitol is isosorbide; the dehydrated derivative of mannitol is isomannide;
the dissolution temperature is 25-60 ℃.
2. The method according to claim 1, wherein the mass ratio of the sugar alcohol and the dehydrated derivative thereof to the hydrophobic ionic liquid is 0.1-0.3: 0.1 to 0.3:1.
3. the method of claim 1, wherein the dissolving time is 1 to 4 hours.
4. The method according to claim 1, wherein the organic solvent is an alcohol-based organic solvent or a nitrile-based organic solvent.
5. The method of claim 1, wherein the volume ratio of the organic solvent to the water is 1-3: 1, the volume ratio of the aqueous solution of the organic solvent to the filtrate is 5-40: 1.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107722033A (en) * | 2017-11-06 | 2018-02-23 | 上海纳米技术及应用国家工程研究中心有限公司 | The method for adding hydrophobic ionic liquid to be evaporated under reduced pressure separation dehydration of sugar alcohols reaction product |
| CN109320522A (en) * | 2018-12-03 | 2019-02-12 | 山东天力药业有限公司 | A method of preparing isobide |
| CN112724154A (en) * | 2019-10-28 | 2021-04-30 | 中国石油化工股份有限公司 | Isosorbide ester plasticizer and preparation method thereof |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107722033A (en) * | 2017-11-06 | 2018-02-23 | 上海纳米技术及应用国家工程研究中心有限公司 | The method for adding hydrophobic ionic liquid to be evaporated under reduced pressure separation dehydration of sugar alcohols reaction product |
| CN109320522A (en) * | 2018-12-03 | 2019-02-12 | 山东天力药业有限公司 | A method of preparing isobide |
| CN112724154A (en) * | 2019-10-28 | 2021-04-30 | 中国石油化工股份有限公司 | Isosorbide ester plasticizer and preparation method thereof |
Non-Patent Citations (1)
| Title |
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| Solubility of xylitol and sorbitol in ionic liquids – Experimental data and modeling;Aristides P. Carneiro, et a;J. Chem. Thermodynamic;第55卷;184–192 * |
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