CN111253413A - Preparation method of isosorbide - Google Patents
Preparation method of isosorbide Download PDFInfo
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Abstract
The invention discloses a preparation method of isosorbide, belonging to the field of catalytic chemistry and chemical engineering. The method comprises the following steps: preparing a niobium pentoxide solid acid catalyst, adding acidic niobium pentoxide into solid sorbitol, and dehydrating at 130 ℃ and under the condition of-0.09 MPa to obtain a reaction solution; dissolving the reaction solution in water, and filtering to remove the solid acid catalyst to obtain filtrate; then adding activated carbon for decolorization, and filtering again to obtain a filtrate; carrying out rotary evaporation on the filtrate to remove water, adding ethyl acetate to dissolve, and then recrystallizing; finally, vacuum centrifuging at low temperature to obtain the isosorbide crystal. The method provided by the invention uses solid acid as a catalyst, has the advantages of high yield, high selectivity, simple and convenient operation, small pollution and easy regeneration, and the yield of the isosorbide can reach more than 85%.
Description
Technical Field
The invention belongs to the field of catalytic chemistry and chemical engineering, and particularly relates to a preparation method of isosorbide.
Background
Sorbitol was listed in 2004 by the U.S. department of energy as twelve platform compounds derived from carbohydrates, present as sweeteners in many berries and fruits. Sorbitol can be subjected to hydrogenolysis, polymerization, dehydration and other reactions to obtain a series of bio-based chemicals and materials with high added values. The isosorbide as a secondary dehydration cyclization product is an important novel bio-based chemical and can be widely applied to the fields of food, cosmetics, medicines and the like.
At present, most domestic isosorbide preparation methods adopt liquid acid catalysis, reduced pressure distillation, organic solvent extraction crystallization and other processes, the process is complex, the requirement on reaction equipment is high, resources are wasted, a large amount of precipitates are generated, and environmental pollution is serious, so that the cost for producing isosorbide is high.
The current concept of green chemistry is well-minded, and an environment-friendly reaction system is a future development trend. The solid acid overcomes the disadvantages of liquid acid, and has surface with
The acid can also be Lewis acid, has wide acid strength distribution, has the characteristics of easy separation from a liquid phase reaction system, no corrosion to equipment, simple post-treatment, less environmental pollution, high selectivity and the like, can be used in a higher temperature range, and enlarges the application range of acid catalytic reaction which can be possibly carried out thermodynamically. Solid acid has attracted great interest as one kind of green environment protecting catalyst and has been used in various acid catalyzed reactions.
In the patent documents disclosed so far, sorbitol solution is often used as a raw material for the production of isosorbide, and liquid acid or molecular sieve is used as a catalyst. However, since the reaction for preparing isosorbide from sorbitol is a dehydration reaction, when the solution is used as a raw material, water in the solution needs to be removed first in the reaction process, and then reactants are dehydrated, thereby causing partial energy waste.
Niobium pentoxide is used as a novel catalytic material, and can be used as an active component, an auxiliary agent or a carrier of a catalyst. Due to the unique acidity and oxidation-reduction property, the catalyst shows better catalytic performance in a plurality of reactions, and has attracted wide attention of scholars at home and abroad.
Disclosure of Invention
Aiming at the problems, the invention provides a preparation method of isosorbide, which adopts acidic Nb2O5As a solid acid catalyst, solid sorbitol is used as a raw material to prepare isosorbide, and the Nb is2O5Before use, the product needs to be pretreated.
The pretreatment process comprises the following steps:
1) weighing Nb2O5Grinding KOH in hot grinding bowl to powder, and calcining to prepare KNbO3；
2) KNbO obtained in the step 1)3Preparation of KNbO from solid3Stirring the solution for the first time, gradually dropwise adding an acid solution until the pH value of the solution is 2-3, continuously stirring, heating for stirring for the second time, separating and drying the obtained precipitate to obtain acidic Nb2O5。
In the step 1), Nb2O5And KOH mole ratio of 1: (2-20), the roasting temperature is 300-500 ℃, and the roasting time is 2-6 h.
The acid in the step 2) can be one or more of sulfuric acid, phosphoric acid or nitric acid, the concentration of the acid solution is 0.1-10 mol/L, KNbO3The concentration of the solution is 0.01-5mol/L, the first stirring temperature is 40 ℃, the stirring time is 10min, the stirring time is continued for 1h, the second stirring temperature is 80 ℃, and the stirring time is 2 h.
A method for preparing isosorbide comprises the following steps:
1) weighing solid sorbitol in a reactor, adding acidic Nb2O5Stirring uniformly to obtain a reaction solution A;
2) adding deionized water into the reaction solution, stirring and dissolving, filtering to obtain a solution B, and recovering niobium pentoxide;
3) adding activated carbon into the solution B, stirring and decoloring for 1 hour at 80 ℃, and filtering to obtain filtrate C;
4) rotatably evaporating the filtrate C at 60 deg.C for 1 hr to remove water to obtain concentrated solution D; adding ethyl acetate solvent into the concentrated solution D, stirring and dissolving for 1 hour at 60 ℃ to prepare ethyl acetate concentrated solution of isosorbide;
5) filtering while hot to obtain ethyl acetate concentrated solution of isosorbide, rotary evaporating at 40 deg.C for concentration, and refrigerating in refrigerator for crystallization to obtain crystal;
6) washing the crystal obtained in the step 5) with ice water, centrifuging and drying to obtain the isosorbide crystal.
In the step 1), the reaction temperature is 130 ℃, the pressure is-0.09 MPa, and the reaction time is 5-10 hours.
In the step 3), the adding amount of the activated carbon is 20% of the mass of the solid sorbitol.
In the step 5), the addition amount of the ethyl acetate is 5 times of the mass of the solid sorbitol.
In the step 5), the crystallization temperature is 5-10 ℃, and the crystallization time is 5 hours.
The centrifugation process in the step 6) adopts a precooling centrifuge, and the drying process adopts vacuum low-temperature drying.
The invention has the beneficial effects that:
1. the method uses solid acid as a catalyst, has the advantages of high yield, high selectivity, simple and convenient operation, little pollution and easy regeneration, and the purity of the isosorbide prepared by the method is 81-95 percent, the recovery rate of the isosorbide can reach more than 85 percent, and the conversion rate of the sorbitol is close to 100 percent.
2. The preparation method takes the self-made niobium pentoxide as the catalyst, is applied to sorbitol dehydration under the conditions of no solvent and reduced pressure to generate the isosorbide, adopts the solid sorbitol as the raw material, reacts in a molten state, can directly dehydrate reactants, and avoids waste caused by repeated behaviors.
3. According to the method, the self-made niobium oxide is used as a solid catalyst, more surface acid can be loaded on the niobium pentoxide through a pretreatment process, a good catalytic effect is achieved on dehydration of sorbitol, the sorbitol can be dehydrated twice at a low temperature (130 ℃) to generate isosorbide, the isosorbide can be recycled, and the industrial application prospect is good.
Drawings
FIG. 1 is a gas chromatogram of a sample sampled and diluted during a reaction;
FIG. 2 is a Raman spectrum of a solid acid catalyst;
FIG. 3 is an infrared diffraction pattern of a solid acid catalyst;
FIG. 4 shows the sorbitol conversion and yield change during the reaction;
FIG. 5 is a gas chromatogram of the reacted and purified isosorbide product;
Detailed Description
The invention is described in further detail below with reference to the following figures and specific examples:
for commercially available Nb2O5The catalyst has been roasted, the surface acid property is weakened, the acid center is mainly loaded on the surface of the catalyst in the ordinary acidification process by an impregnation method, the catalytic dehydration effect on sorbitol is not obvious, the purity, the yield and the like of isosorbide are low, and Nb is needed2O5Through the pretreatment and preparation processes, the acidification step is omitted, more and stronger acid centers can be obtained, and the catalytic effect on dehydration of sorbitol is good.
Example 1
Preparation of solid acid catalyst:
1) preparing a potassium niobate solution: 13.25g Nb are weighed2O5Grinding 66g KOH in a hot bowl to powder, transferring to a crucible, roasting at 400 ℃ for 3h, taking out, putting into a beaker, adding 1L water for dissolving to obtain KNbO3Standing the solution for later use.
2) Taking potassium niobate solution, stirring the solution in a three-neck flask at 40 ℃ for 10 minutes, then dropwise adding 2mol/L sulfuric acid solution until the pH value of the solution is 2, continuously stirring the solution for 1 hour, heating the solution to 80 ℃, stirring the solution for 2 hours, taking the solution out, cooling the solution to room temperature, performing suction filtration, putting a filter cake into a 100 ℃ oven for drying, taking out the dried filter cake, and grinding the dried filter cake into powder for later use. The prepared niobium pentoxide was subjected to raman and infrared diffraction spectrum tests, and the results are shown in fig. 2 and 3.
The preparation method of the isosorbide comprises the following steps:
1) weighing 50g of solid sorbitol in a reactor, adding 10g of niobium pentoxide prepared by sulfuric acid, stirring and reacting for 7 hours at 130 ℃ and under the pressure of-0.09 MPa, wherein the highest yield of isosorbide is 86.04% according to the detection result of gas chromatography, the sample obtained after sampling and diluting isosorbide in the reaction process is subjected to gas chromatography, and the result is shown in figure 1, and a relation graph between sorbitol conversion rate and isosorbide yield is drawn, as shown in figure 4;
2) adding 100mL of deionized water into the reaction solution, stirring and dissolving, and recovering the solid acid catalyst after filtering;
3) adding 10g of activated carbon particles into the solution, stirring and decoloring for 1 hour at 80 ℃ in a water bath, and filtering to obtain filtrate;
4) rotatably evaporating the filtrate at 60 deg.C for 1 hr to remove water to obtain concentrated solution;
5) adding 150mL of ethyl acetate into the concentrated solution, and stirring and dissolving for 1 hour at the temperature of 60 ℃;
6) filtering while the solution is hot to obtain an ethyl acetate concentrated solution of isosorbide, performing rotary evaporation concentration at 40 ℃, and then placing the solution in a refrigerator for cold storage and crystallization, wherein the temperature is kept at 5-10 ℃, and the crystallization time is 5 hours;
7) the obtained product was washed with ice water, centrifuged, and vacuum-dried at low temperature to obtain 37.68g of isosorbide crystals, which were detected by gas chromatography and had a purity of 93.53% as shown in FIG. 5.
Example 2
Preparation of solid acid catalyst:
1) preparing a potassium niobate solution: 13.25g Nb are weighed2O5Grinding 66g KOH in a hot bowl to powder, transferring to a crucible, roasting at 400 ℃ for 3h, taking out, putting into a beaker, adding 1L water for dissolving to obtain KNbO3Standing the solution for later use.
2) Taking potassium niobate solution, stirring the solution in a three-neck flask at 40 ℃ for 10 minutes, then dropwise adding 2mol/L sulfuric acid solution until the pH value of the solution is 2, continuously stirring the solution for 1 hour, heating the solution to 80 ℃, stirring the solution for 2 hours, taking the solution out, cooling the solution to room temperature, performing suction filtration, putting a filter cake into a 100 ℃ oven for drying, taking out the dried filter cake, and grinding the dried filter cake into powder for later use.
The preparation method of the isosorbide comprises the following steps:
1) weighing 100g of solid sorbitol in a reactor, adding 20g of niobium pentoxide prepared by sulfuric acid, and stirring and reacting for 8 hours at the temperature of 130 ℃ and under the pressure of-0.09 MPa;
2) adding 200mL of deionized water into the reaction solution, stirring and dissolving, and recovering the solid acid catalyst after filtering;
3) adding 20g of activated carbon particles into the solution, stirring and decoloring for 1 hour at 80 ℃ in a water bath, and filtering to obtain filtrate;
4) rotatably evaporating the filtrate at 60 deg.C for 1 hr to remove water to obtain concentrated solution;
5) adding 300mL of ethyl acetate into the concentrated solution, and stirring and dissolving for 1 hour at the temperature of 60 ℃;
6) filtering while the solution is hot to obtain an ethyl acetate concentrated solution of isosorbide, performing rotary evaporation concentration at 40 ℃, and then placing the solution in a refrigerator for cold storage and crystallization, wherein the temperature is kept at 5-10 ℃, and the crystallization time is 5 hours;
7) and (3) washing the centrifugal machine by using ice water, centrifuging, and drying in vacuum at low temperature to obtain 76.84g of isosorbide crystals, wherein the purity is 92.37% through gas chromatography detection.
Example 3
Preparation of solid acid catalyst:
1) preparing a potassium niobate solution: 13.25g Nb are weighed2O5Grinding 66g KOH in a hot bowl to powder, transferring to a crucible, roasting at 400 ℃ for 3h, taking out, putting into a beaker, adding 1L water for dissolving to obtain KNbO3Standing the solution for later use.
2) Taking potassium niobate solution, stirring the solution in a three-neck flask at 40 ℃ for 10 minutes, then dropwise adding 2mol/L sulfuric acid solution until the pH value of the solution is 2, continuously stirring the solution for 1 hour, heating the solution to 80 ℃, stirring the solution for 2 hours, taking the solution out, cooling the solution to room temperature, performing suction filtration, putting a filter cake into a 100 ℃ oven for drying, taking out the dried filter cake, and grinding the dried filter cake into powder for later use.
The preparation method of the isosorbide comprises the following steps:
1) weighing 50g of solid sorbitol in a reactor, adding 20g of niobium pentoxide prepared by sulfuric acid, and stirring and reacting for 6 hours at the temperature of 130 ℃ and under the pressure of-0.09 MPa;
2) adding 100mL of deionized water into the reaction solution, stirring and dissolving, and recovering the solid acid catalyst after filtering;
3) adding 10g of activated carbon particles into the solution, stirring and decoloring for 1 hour at 80 ℃ in a water bath, and filtering to obtain filtrate;
4) rotatably evaporating the filtrate at 60 deg.C for 1 hr to remove water to obtain concentrated solution;
5) adding 150mL of ethyl acetate into the concentrated solution, and stirring and dissolving for 1 hour at the temperature of 60 ℃;
6) filtering while the solution is hot to obtain an ethyl acetate concentrated solution of isosorbide, performing rotary evaporation concentration at 40 ℃, and then placing the solution in a refrigerator for cold storage and crystallization, wherein the temperature is kept at 5-10 ℃, and the crystallization time is 5 hours;
7) and (3) washing the centrifugal machine by using ice water, centrifuging, and drying in vacuum at low temperature to obtain 36.05g of isosorbide crystals, wherein the purity is 92.37% through gas chromatography detection.
Example 4
Preparation of solid acid catalyst:
1) preparing a potassium niobate solution: 13.25g Nb are weighed2O5Grinding 66g KOH in a hot bowl to powder, transferring to a crucible, roasting at 400 ℃ for 3h, taking out, putting into a beaker, adding 1L water for dissolving to obtain KNbO3Standing the solution for later use.
2) Taking potassium niobate solution, stirring the solution in a three-neck flask at 40 ℃ for 10 minutes, then dropwise adding 2mol/L phosphoric acid solution until the pH value of the solution is 2, continuously stirring the solution for 1 hour, heating the solution to 80 ℃, stirring the solution for 2 hours, taking the solution out, cooling the solution to room temperature, performing suction filtration, putting a filter cake into a 100 ℃ oven for drying, taking out the dried filter cake, and grinding the dried filter cake into powder for later use.
The preparation method of the isosorbide comprises the following steps:
1) weighing 50g of solid sorbitol in a reactor, adding 20g of niobium pentoxide prepared from phosphoric acid, and stirring and reacting for 6 hours at the temperature of 130 ℃ and under the pressure of-0.09 MPa;
2) adding 100mL of deionized water into the reaction solution, stirring and dissolving, and recovering the solid acid catalyst after filtering;
3) adding 10g of activated carbon particles into the solution, stirring and decoloring for 1 hour at 80 ℃ in a water bath, and filtering to obtain filtrate;
4) rotatably evaporating the filtrate at 60 deg.C for 1 hr to remove water to obtain concentrated solution;
5) adding 150mL of ethyl acetate into the concentrated solution, and stirring and dissolving for 1 hour at the temperature of 60 ℃;
6) filtering while the solution is hot to obtain an ethyl acetate concentrated solution of isosorbide, performing rotary evaporation concentration at 40 ℃, and then placing the solution in a refrigerator for cold storage and crystallization, wherein the temperature is kept at 5-10 ℃, and the crystallization time is 5 hours;
7) and (3) washing the centrifugal machine with ice water for centrifugation, and drying in vacuum at low temperature to obtain 10.12g of isosorbide crystals, wherein the purity is 85.17% through gas chromatography detection.
Example 5
Preparation of solid acid catalyst:
1) preparing a potassium niobate solution: 13.25g Nb are weighed2O5Grinding 66g KOH in a hot bowl to powder, transferring to a crucible, roasting at 400 ℃ for 3h, taking out, putting into a beaker, adding 1L water for dissolving to obtain KNbO3Standing the solution for later use.
2) Taking potassium niobate solution, stirring the solution in a three-neck flask at 40 ℃ for 10 minutes, then dropwise adding 2mol/L nitric acid solution until the pH value of the solution is 2, continuously stirring the solution for 1 hour, heating the solution to 80 ℃, stirring the solution for 2 hours, taking the solution out, cooling the solution to room temperature, performing suction filtration, putting a filter cake into a 100 ℃ oven for drying, taking out the dried filter cake, and grinding the dried filter cake into powder for later use.
The preparation method of the isosorbide comprises the following steps:
1) weighing 50g of solid sorbitol in a reactor, adding 20g of niobium pentoxide prepared by nitric acid, and stirring and reacting for 6 hours at the temperature of 130 ℃ and under the pressure of-0.09 MPa;
2) adding 100mL of deionized water into the reaction solution, stirring and dissolving, and recovering the solid acid catalyst after filtering;
3) adding 10g of activated carbon particles into the solution, stirring and decoloring for 1 hour at 80 ℃ in a water bath, and filtering to obtain filtrate;
4) rotatably evaporating the filtrate at 60 deg.C for 1 hr to remove water to obtain concentrated solution;
5) adding 150mL of ethyl acetate into the concentrated solution, and stirring and dissolving for 1 hour at the temperature of 60 ℃;
6) filtering while the solution is hot to obtain an ethyl acetate concentrated solution of isosorbide, performing rotary evaporation concentration at 40 ℃, and then placing the solution in a refrigerator for cold storage and crystallization, wherein the temperature is kept at 5-10 ℃, and the crystallization time is 5 hours;
7) and (3) washing the centrifugal machine with ice water for centrifugation, and drying the centrifugal machine at low temperature in vacuum to obtain 7.61g of isosorbide crystals, wherein the purity is 81.72% through gas chromatography detection.
Table 1 reaction results for different acid acidification of niobium pentoxide.
Claims (10)
1. The preparation method of isosorbide is characterized in that acidic Nb is adopted2O5As a solid acid catalyst, solid sorbitol is used as a raw material to prepare isosorbide, and the Nb is2O5Before use, the product needs to be pretreated.
2. The preparation method according to claim 1, wherein the pretreatment process comprises:
1) weighing Nb2O5Grinding KOH in hot grinding bowl to powder, and calcining to prepare KNbO3A solid;
2) KNbO obtained in the step 1)3Preparation of KNbO from solid3Stirring the solution for the first time, gradually dropwise adding an acid solution until the pH value of the solution is 2-3, continuously stirring, heating for stirring for the second time, separating and drying the obtained precipitate to obtain acidic Nb2O5。
3. The method according to claim 2, wherein in step 1), Nb is added2O5And KOH mole ratio of 1: (2-20), the roasting temperature is 300-500 ℃, and the roasting time is 2-6 h.
4. The preparation method according to claim 2, wherein the acid in step 2) is one or more of sulfuric acid, phosphoric acid or nitric acid, the concentration of the acid solution is 0.1-10 mol/L, KNbO3The concentration of the solution is 0.01-5mol/L, the first stirring temperature is 40 ℃, the stirring time is 10min, the stirring time is continued for 1h, the second stirring temperature is 80 ℃, and the stirring time is 2 h.
5. The method of claim 1, comprising the steps of:
1) weighing solid sorbitol in a reactor, adding acidic Nb2O5Stirring uniformly to obtain a reaction solution A;
2) adding deionized water into the reaction solution, stirring and dissolving, filtering to obtain a solution B, and recovering niobium pentoxide;
3) adding activated carbon into the solution B, stirring and decoloring for 1 hour at 80 ℃, and filtering to obtain filtrate C;
4) rotatably evaporating the filtrate C at 60 deg.C for 1 hr to remove water to obtain concentrated solution D; adding ethyl acetate solvent into the concentrated solution D, stirring and dissolving for 1 hour at 60 ℃ to prepare ethyl acetate concentrated solution of isosorbide;
5) filtering while hot to obtain ethyl acetate concentrated solution of isosorbide, rotary evaporating at 40 deg.C for concentration, and refrigerating in refrigerator for crystallization to obtain crystal;
6) washing the crystal obtained in the step 5) with ice water, centrifuging and drying to obtain the isosorbide crystal.
6. The preparation method according to claim 5, wherein in the step 1), the reaction temperature is 130 ℃, the pressure is-0.09 MPa, and the reaction time is 5-10 hours.
7. The method for preparing isosorbide according to claim 5, wherein in step 3), the amount of activated carbon added is 20% by mass of the solid sorbitol.
8. The method according to claim 5, wherein the amount of ethyl acetate added in step 5) is 5 times the mass of the solid sorbitol.
9. The method for preparing isosorbide according to claim 5, wherein the crystallization temperature in step 5) is 5 to 10 ℃ and the crystallization time is 5 hours.
10. The method for preparing isosorbide according to claim 5, wherein the centrifugation process in step 6) is performed by using a pre-cooled centrifuge, and the drying process is performed by vacuum low temperature drying.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114437099A (en) * | 2020-11-02 | 2022-05-06 | 中国石油化工股份有限公司 | Preparation method of high-purity isosorbide |
| CN114671883A (en) * | 2022-05-07 | 2022-06-28 | 华东理工大学 | Method for preparing isosorbide by dehydrating sorbitol under catalysis of niobium-based solid acid |
| CN115010718A (en) * | 2022-07-27 | 2022-09-06 | 北京石油化工学院 | Method for preparing isosorbide by dehydrating sorbitol under catalysis of polymeric ionic liquid |
Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101234347A (en) * | 2008-02-29 | 2008-08-06 | 中国建筑材料科学研究总院 | Method for preparing niobate composition metal oxide nano particle |
| CN102757445A (en) * | 2012-07-27 | 2012-10-31 | 山东福田药业有限公司 | Preparation technique of isosorbide |
| CN103272595A (en) * | 2013-05-21 | 2013-09-04 | 苏州奥索特新材料有限公司 | Catalyst for preparing isosorbide by utilizing celluloses and preparation method of catalyst |
| CN103304366A (en) * | 2013-05-31 | 2013-09-18 | 中国计量学院 | Catalytic synthesis process of diphenylmethane |
| WO2015161468A1 (en) * | 2014-04-23 | 2015-10-29 | East China University Of Science And Technology | Methods and systems for producing isosorbide from biomass background |
| US20160090331A1 (en) * | 2014-09-26 | 2016-03-31 | IFP Energies Nouvelles | Process for transformation of a feedstock comprising a lignocellulosic biomass using an acidic homogeneous catalyst in combination with a heterogeneous catalyst comprising a specific substrate |
| CN108690039A (en) * | 2018-06-26 | 2018-10-23 | 大连理工大学 | A kind of method that sorb dehydration of alcohols prepares isobide |
| CN109734722A (en) * | 2019-01-21 | 2019-05-10 | 中国科学院成都有机化学有限公司 | A kind of method that sorb dehydration of alcohols prepares isobide |
| CN110092795A (en) * | 2018-01-31 | 2019-08-06 | 中国科学院成都有机化学有限公司 | A kind of preparation method of isobide |
| CN110483678A (en) * | 2019-07-19 | 2019-11-22 | 中国科学院山西煤炭化学研究所 | A kind of catalyst and its preparation method and application preparing isobide for sorb dehydration of alcohols |
-
2020
- 2020-02-27 CN CN202010122905.1A patent/CN111253413B/en active Active
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101234347A (en) * | 2008-02-29 | 2008-08-06 | 中国建筑材料科学研究总院 | Method for preparing niobate composition metal oxide nano particle |
| CN102757445A (en) * | 2012-07-27 | 2012-10-31 | 山东福田药业有限公司 | Preparation technique of isosorbide |
| CN103272595A (en) * | 2013-05-21 | 2013-09-04 | 苏州奥索特新材料有限公司 | Catalyst for preparing isosorbide by utilizing celluloses and preparation method of catalyst |
| CN103304366A (en) * | 2013-05-31 | 2013-09-18 | 中国计量学院 | Catalytic synthesis process of diphenylmethane |
| WO2015161468A1 (en) * | 2014-04-23 | 2015-10-29 | East China University Of Science And Technology | Methods and systems for producing isosorbide from biomass background |
| US20160090331A1 (en) * | 2014-09-26 | 2016-03-31 | IFP Energies Nouvelles | Process for transformation of a feedstock comprising a lignocellulosic biomass using an acidic homogeneous catalyst in combination with a heterogeneous catalyst comprising a specific substrate |
| CN110092795A (en) * | 2018-01-31 | 2019-08-06 | 中国科学院成都有机化学有限公司 | A kind of preparation method of isobide |
| CN108690039A (en) * | 2018-06-26 | 2018-10-23 | 大连理工大学 | A kind of method that sorb dehydration of alcohols prepares isobide |
| CN109734722A (en) * | 2019-01-21 | 2019-05-10 | 中国科学院成都有机化学有限公司 | A kind of method that sorb dehydration of alcohols prepares isobide |
| CN110483678A (en) * | 2019-07-19 | 2019-11-22 | 中国科学院山西煤炭化学研究所 | A kind of catalyst and its preparation method and application preparing isobide for sorb dehydration of alcohols |
Non-Patent Citations (7)
| Title |
|---|
| FREDERIC DELBECQ，ET AL.: "Isosorbide: Recent advances in catalytic production", 《MOLECULAR CATALYSIS》 * |
| G. FLECHE，ET AL.: "Isosorbide* Preparation, Properties and Chemistry", 《STARCW/STARKE》 * |
| SUSUMU OKAZAKI，ET AL.: "SURFACE PROPERTIES AND CATALYTIC ACTIVITIES OF AMORPHOUS NIOBIUM PHOSPHATE AND A COMPARISON WITH THOSE OF H3P04-TREATED NIOBIUM OXIDE", 《CATALYSIS TODAY》 * |
| ZHEN-CHEN TANG,ET AL.: "Phosphoric Acid Modified Nb2O5:A Selective and Reusable Catalyst for Dehydration of Sorbitol to Isosorbide", 《BULL. KOREAN CHEM. SOC.》 * |
| 孙鹏 等: "催化山梨醇脱水制备异山梨醇的固体酸催化剂", 《生物加工工程》 * |
| 程月红 等: "铌酸的合成与表征", 《工业催化》 * |
| 金建策 等: "铌酸改性及催化合成油酸异丁酯", 《化学工程与技术》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114437099A (en) * | 2020-11-02 | 2022-05-06 | 中国石油化工股份有限公司 | Preparation method of high-purity isosorbide |
| CN114671883A (en) * | 2022-05-07 | 2022-06-28 | 华东理工大学 | Method for preparing isosorbide by dehydrating sorbitol under catalysis of niobium-based solid acid |
| CN115010718A (en) * | 2022-07-27 | 2022-09-06 | 北京石油化工学院 | Method for preparing isosorbide by dehydrating sorbitol under catalysis of polymeric ionic liquid |
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