CN107473934B - Preparation method of sorbitol - Google Patents
Preparation method of sorbitol Download PDFInfo
- Publication number
- CN107473934B CN107473934B CN201710757968.2A CN201710757968A CN107473934B CN 107473934 B CN107473934 B CN 107473934B CN 201710757968 A CN201710757968 A CN 201710757968A CN 107473934 B CN107473934 B CN 107473934B
- Authority
- CN
- China
- Prior art keywords
- reaction
- sorbitol
- catalyst
- preparation
- reaction kettle
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 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 title claims abstract description 54
- 239000000600 sorbitol Substances 0.000 title claims abstract description 48
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 76
- 239000003054 catalyst Substances 0.000 claims abstract description 31
- 239000001257 hydrogen Substances 0.000 claims abstract description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 23
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims abstract description 20
- 239000008103 glucose Substances 0.000 claims abstract description 20
- 229910052741 iridium Inorganic materials 0.000 claims abstract description 11
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000011049 filling Methods 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 8
- 238000010438 heat treatment Methods 0.000 claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 8
- 230000035484 reaction time Effects 0.000 claims description 4
- 239000012429 reaction media Substances 0.000 abstract description 9
- 239000007809 chemical reaction catalyst Substances 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 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 47
- 229960002920 sorbitol Drugs 0.000 description 47
- 239000012263 liquid product Substances 0.000 description 18
- 238000007789 sealing Methods 0.000 description 12
- 238000004128 high performance liquid chromatography Methods 0.000 description 11
- 239000007789 gas Substances 0.000 description 8
- 238000001816 cooling Methods 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 238000004451 qualitative analysis Methods 0.000 description 6
- 238000004445 quantitative analysis Methods 0.000 description 6
- 238000005303 weighing Methods 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 229930003268 Vitamin C Natural products 0.000 description 2
- -1 alkane compounds Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000005034 decoration Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- 235000019154 vitamin C Nutrition 0.000 description 2
- 239000011718 vitamin C Substances 0.000 description 2
- 239000002028 Biomass Substances 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 239000002551 biofuel Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 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
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000105 evaporative light scattering detection Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002303 glucose derivatives Chemical class 0.000 description 1
- 238000007210 heterogeneous catalysis Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000005272 metallurgy Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 235000021092 sugar substitutes Nutrition 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
- C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2282—Unsaturated compounds used as ligands
- B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
-
- B01J35/50—
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/60—Reduction reactions, e.g. hydrogenation
- B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
- B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
- B01J2231/643—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of R2C=O or R2C=NR (R= C, H)
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0225—Complexes comprising pentahapto-cyclopentadienyl analogues
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0238—Complexes comprising multidentate ligands, i.e. more than 2 ionic or coordinative bonds from the central metal to the ligand, the latter having at least two donor atoms, e.g. N, O, S, P
- B01J2531/0241—Rigid ligands, e.g. extended sp2-carbon frameworks or geminal di- or trisubstitution
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/827—Iridium
Abstract
The invention belongs to the field of chemical synthesis, and particularly relates to a preparation method of sorbitol. The preparation method provided by the invention comprises the following steps: adding glucose, a catalyst and a reaction medium into a reaction kettle, then filling hydrogen into the reaction kettle, and heating for reaction to obtain sorbitol; the catalyst is a semi-sandwich type iridium complex. The preparation method provided by the invention takes the semi-sandwich type iridium complex as a reaction catalyst, and can keep higher selectivity and stability of the reaction under relatively mild reaction conditions, thereby obtaining higher sorbitol preparation yield. Experimental results show that the yield of the sorbitol prepared by the method provided by the invention can reach 95.6% at most.
Description
Technical Field
The invention belongs to the field of chemical synthesis, and particularly relates to a preparation method of sorbitol.
Background
In 2004, the U.S. department of energy identified D-sorbitol as one of the twelve most important value-added chemicals that could be extracted from biomass, and the alkane compounds obtained therefrom could be used for the production of liquid biofuels. D-sorbitol, an excellent commercial chemical base material, is an important additive and intermediate. In the field of pharmacy, the vitamin C is an important raw material for synthesizing vitamin C, and can be applied to the preparation of compound vitamin preparations and diuretics; the cosmetic industry is mainly used as lubricant and moisture regulator. Can be used as softening agent, adhesive, metal surface treating agent and the like in leather, metallurgy, papermaking and other industries. In the catering industry, D-sorbitol is a very important sugar substitute, with a global annual production of over 800000 tons. In addition, the D-sorbitol can be further degraded into a series of downstream products in the petrochemical industry, and the additional value of the D-sorbitol is greatly improved.
At present, the reported glucose hydrogenation catalytic system is mainly based on heterogeneous catalysis, and platinum, ruthenium and nickel are mostly adopted as central metals and loaded on carriers such as activated carbon, metal oxides and the like. Lazaridis (Catalysis Today 257(2015):281-290.) reported that the 1 wt% Pt/AC catalyst used achieved high selectivity conversion of glucose at a lower hydrogen pressure of 1.6MPa, but the reaction temperature of 180 ℃ was relatively high. Perrard (Applied Catalysis A: General,2007,331:100-104.) reported a selectivity for D-sorbitol of > 99.5% over Pt/C catalyst at 100 ℃ and 8MPa hydrogen pressure, but too high a hydrogen pressure. Lu Lin (Carbohydrate research 346.11(2011): 1327-.
Therefore, the exploration of a preparation method of sorbitol with high selectivity, good stability and mild reaction conditions is a technical problem to be overcome in the field.
Disclosure of Invention
In view of the above, the present invention aims to provide a method for preparing sorbitol, which has high selectivity, good stability and mild reaction conditions.
The invention provides a preparation method of sorbitol, which comprises the following steps:
adding glucose, a catalyst and a reaction medium into a reaction kettle, then filling hydrogen into the reaction kettle, and heating for reaction to obtain sorbitol;
the catalyst is a semi-sandwich type iridium complex.
Preferably, the semi-sandwich type iridium complex is a complex with a structure shown in formula (I):
preferably, the mass ratio of the catalyst to the glucose is (0.01-0.05): 1.
preferably, the reaction medium is water.
Preferably, the dosage ratio of the glucose to the reaction medium is (50-150) mg: (1-3) mL.
Preferably, the pressure of the reaction kettle after hydrogen filling is 1-5 MPa.
Preferably, the reaction temperature is 80-150 ℃.
Preferably, the reaction time is 1-12 h.
Preferably, the reaction is carried out under stirring conditions.
Preferably, the rotating speed of the stirring is 500-1500 revolutions/min.
Compared with the prior art, the invention provides a preparation method of sorbitol. The preparation method provided by the invention comprises the following steps: adding glucose, a catalyst and a reaction medium into a reaction kettle, then filling hydrogen into the reaction kettle, and heating for reaction to obtain sorbitol; the catalyst is a semi-sandwich type iridium complex. The preparation method provided by the invention takes the semi-sandwich type iridium complex as a reaction catalyst, and can keep higher selectivity and stability of the reaction under relatively mild reaction conditions, thereby obtaining higher sorbitol preparation yield. Experimental results show that the yield of the sorbitol prepared by the method provided by the invention can reach 95.6% at most.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to the provided drawings without creative efforts.
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of a catalyst provided in an example of the present invention;
FIG. 2 is a nuclear magnetic resonance carbon spectrum of a catalyst provided in an example of the present invention;
FIG. 3 is an HPLC plot of the reaction product provided in example 1 of the present invention.
Detailed Description
The technical solutions in the embodiments of the present invention are clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The invention provides a preparation method of sorbitol, which comprises the following steps:
adding glucose, a catalyst and a reaction medium into a reaction kettle, then filling hydrogen into the reaction kettle, and heating for reaction to obtain sorbitol;
the catalyst is a semi-sandwich type iridium complex.
In the present invention, glucose, catalyst and reaction medium are preferably added to the reaction vessel. Wherein, the catalyst is a semi-sandwich type iridium complex, preferably a complex with a structure shown in a formula (I):
in the present invention, the reaction medium is preferably water; the mass ratio of the catalyst to the glucose is preferably (0.01-0.05): 1, more preferably 0.02: 1; the dosage ratio of the glucose to the reaction medium is preferably (50-150) mg: (1-3) mL, more preferably 100 mg: 2 mL.
And then filling hydrogen into the reaction kettle, wherein the pressure of the reaction kettle after the hydrogen filling is preferably 1-5 MPa, and more preferably 2-3 MPa. In the present invention, in order to ensure that no other gas is present in the reaction vessel, it is preferred to replace the gas in the reaction vessel with hydrogen gas several times and then charge the hydrogen gas to the desired pressure.
And after the hydrogen filling is finished, heating the reaction kettle for reaction. Wherein the heating rate of the reaction kettle is preferably 5-15 ℃/min, and more preferably 10 ℃/min; the reaction temperature is preferably 80-150 ℃, and more preferably 100-120 ℃; the reaction time is preferably 1-12 h, and more preferably 2-6 h. In the present invention, the reaction time refers to the time from the temperature rise of the reaction vessel to the reaction completion. In the present invention, the reaction is carried out under stirring conditions; the rotating speed of the stirring is 500-1500 revolutions/min, and 900 revolutions/min is more preferable. After the reaction is finished, sorbitol is obtained.
The preparation method provided by the invention takes the semi-sandwich type iridium complex as a reaction catalyst, and can keep higher selectivity and stability of the reaction under relatively mild reaction conditions, thereby obtaining higher sorbitol preparation yield. Experimental results show that the yield of the sorbitol prepared by the method provided by the invention can reach 95.6% at most.
For the sake of clarity, the following examples are given in detail.
In the following examples, the catalysts used are all complexes of formula (I), and the preparation process comprises: 0.6mmol of [ Cp IrCl ]2]2And 1.2 mmoleAg2SO4Adding into 5mL deionized water, stirring the solution at room temperature for 10H, filtering to remove precipitate AgCl, and vacuum drying to obtain [ Cp Ir (H)2O)3]SO4And (3) solid powder. 0.1mmol of [ Cp. multidot.Ir (H) was diluted with 10mL of water2O)3]SO4Dissolving, adding 0.1mmol of bipyridyl ligand in argon atmosphere, stirring at room temperature for 12h, carrying out vacuum spin-drying on the solution, and carrying out vacuum drying on the obtained solid to obtain the target catalyst.
The NMR (nuclear magnetic resonance) analysis of the catalyst prepared as described above is shown in fig. 1 and 2, fig. 1 is a nuclear magnetic resonance hydrogen spectrum of the catalyst provided in the example of the present invention, fig. 2 is a nuclear magnetic resonance carbon spectrum of the catalyst provided in the example of the present invention, and it can be seen from fig. 1 and 2 that the catalyst provided in the example of the present invention has the structure of formula (I).
In the following examples, the reaction vessel was a stainless steel autoclave (PARR, 0.01L).
In the following examples, the qualitative and quantitative measuring instruments were as follows: the High Performance Liquid Chromatography (HPLC) is Hitachi L-2000, the liquid chromatography column is Cosmosil Sugar-D, and the detector is an Alltech ELSD 2000ES evaporation photodetector; liquid phase conditions: SUGAR SH1011 column, mobile phase: water, flow rate: 0.5ml/min, column temperature: at 50 ℃.
Example 1
Sorbitol was prepared according to the following reaction sequence:
the method specifically comprises the following steps: weighing 100mg of glucose and 2mg of catalyst, mixing in a reaction kettle, adding 2mL of water, sealing the reaction kettle, replacing gas in the reaction kettle with hydrogen for three times, introducing 3MPa of hydrogen, and sealing. The reaction kettle is placed on a magnetic stirrer, the stirrer is started to rotate at 900 revolutions per minute, the temperature is increased to 120 ℃ at the temperature increase rate of 10 ℃/min, and the temperature is maintained for 6 hours. After the reaction is finished, cooling to room temperature, and collecting a liquid product.
Qualitative and quantitative analysis by HPLC (high performance liquid chromatography) was carried out, and the results are shown in fig. 3, and fig. 3 is an HPLC chart of the reaction product provided in example 1 of the present invention. Obtaining the sorbitol content in the liquid product according to the HPLC chromatogram result, and calculating the sorbitol yield according to the sorbitol content in the liquid product and the sorbitol theoretical yield, wherein the result is as follows: 95.6 percent.
According to the above analysis, the yield in the present invention is the yield of pure sorbitol.
Example 2
Weighing 100mg of glucose and 1mg of catalyst, mixing in a reaction kettle, adding 2mL of water, sealing the reaction kettle, replacing gas in the reaction kettle with hydrogen for three times, introducing 3MPa of hydrogen, and sealing. The reaction kettle is placed on a magnetic stirrer, the stirrer is started to rotate at 900 revolutions per minute, the temperature is increased to 120 ℃ at the temperature increase rate of 10 ℃/min, and the temperature is maintained for 6 hours. After the reaction is finished, cooling to room temperature, and collecting a liquid product.
Performing qualitative and quantitative analysis by HPLC to obtain the sorbitol content in the liquid product; the yield of sorbitol in this example was calculated from the sorbitol content in the liquid product and the theoretical yield of sorbitol, and the results were: 86.5 percent.
Example 3
Weighing 100mg of glucose and 2mg of catalyst, mixing in a reaction kettle, adding 2mL of water, sealing the reaction kettle, replacing gas in the reaction kettle with hydrogen for three times, introducing 2MPa of hydrogen, and sealing. The reaction kettle is placed on a magnetic stirrer, the stirrer is started to rotate at 900 revolutions per minute, the temperature is increased to 120 ℃ at the temperature increase rate of 10 ℃/min, and the temperature is maintained for 6 hours. After the reaction is finished, cooling to room temperature, and collecting a liquid product.
Performing qualitative and quantitative analysis by HPLC to obtain the sorbitol content in the liquid product; the yield of sorbitol in this example was calculated from the sorbitol content in the liquid product and the theoretical yield of sorbitol, and the results were: 72.8 percent.
Example 4
Weighing 100mg of glucose and 2mg of catalyst, mixing in a reaction kettle, adding 2mL of water, sealing the reaction kettle, replacing gas in the reaction kettle with hydrogen for three times, introducing 3MPa of hydrogen, and sealing. The reaction kettle is placed on a magnetic stirrer, the stirrer is started to rotate at 900 revolutions per minute, the temperature is increased to 100 ℃ at the temperature increasing rate of 10 ℃/min, and the temperature is maintained for 6 hours. After the reaction is finished, cooling to room temperature, and collecting a liquid product.
Performing qualitative and quantitative analysis by HPLC to obtain the sorbitol content in the liquid product; the yield of sorbitol in this example was calculated from the sorbitol content in the liquid product and the theoretical yield of sorbitol, and the results were: 50.6 percent.
Example 5
Weighing 100mg of glucose and 2mg of catalyst, mixing in a reaction kettle, adding 2mL of water, sealing the reaction kettle, replacing gas in the reaction kettle with hydrogen for three times, introducing 3MPa of hydrogen, and sealing. The reaction kettle is placed on a magnetic stirrer, the stirrer is started to rotate at 900 revolutions per minute, the temperature is increased to 120 ℃ at the temperature increase rate of 10 ℃/min and is maintained for 2 hours. After the reaction is finished, cooling to room temperature, and collecting a liquid product.
Performing qualitative and quantitative analysis by HPLC to obtain the sorbitol content in the liquid product; the yield of sorbitol in this example was calculated from the sorbitol content in the liquid product and the theoretical yield of sorbitol, and the results were: 38.2 percent.
Example 6
Weighing 100mg of glucose and 2mg of catalyst, mixing in a reaction kettle, adding 2mL of isopropanol, sealing the reaction kettle, replacing gas in the reaction kettle with hydrogen for three times, introducing 3MPa of hydrogen, and sealing. The reaction kettle is placed on a magnetic stirrer, the stirrer is started to rotate at 900 revolutions per minute, the temperature is increased to 120 ℃ at the temperature increase rate of 10 ℃/min, and the temperature is maintained for 6 hours. After the reaction is finished, cooling to room temperature, and collecting a liquid product.
Performing qualitative and quantitative analysis by HPLC to obtain the sorbitol content in the liquid product; the yield of sorbitol in this example was calculated from the sorbitol content in the liquid product and the theoretical yield of sorbitol, and the results were: 25.3 percent.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (5)
1. A preparation method of sorbitol comprises the following steps:
adding glucose, a catalyst and water into a reaction kettle, then filling hydrogen into the reaction kettle, and heating for reaction to obtain sorbitol;
the catalyst is a semi-sandwich type iridium complex;
the semi-sandwich type iridium complex is a complex with a structure shown in a formula (I):
the pressure of the reaction kettle after hydrogen filling is 3-5 MPa;
the reaction temperature is 120-150 ℃, and the reaction time is 6-12 h.
2. The preparation method according to claim 1, wherein the mass ratio of the catalyst to the glucose is (0.01-0.05): 1.
3. the method according to claim 1, wherein the ratio of the glucose to the water is (50-150) mg: (1-3) mL.
4. The method according to claim 1, wherein the reaction is carried out under stirring.
5. The method according to claim 4, wherein the stirring is performed at a rotation speed of 500 to 1500 rpm.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710757968.2A CN107473934B (en) | 2017-08-29 | 2017-08-29 | Preparation method of sorbitol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710757968.2A CN107473934B (en) | 2017-08-29 | 2017-08-29 | Preparation method of sorbitol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN107473934A CN107473934A (en) | 2017-12-15 |
| CN107473934B true CN107473934B (en) | 2020-04-07 |
Family
ID=60602974
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710757968.2A Active CN107473934B (en) | 2017-08-29 | 2017-08-29 | Preparation method of sorbitol |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN107473934B (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1214333A (en) * | 1997-10-09 | 1999-04-21 | 中国石油化工总公司 | Process of hydrogenating glucose to prepare sorbierite |
| CN104370692A (en) * | 2013-08-13 | 2015-02-25 | 北京化工大学 | Polyol preparation method through glucose hydrogenolysis |
| CN105712854A (en) * | 2016-01-25 | 2016-06-29 | 中国科学技术大学先进技术研究院 | Method for selectively preparing 1-hydroxyl-2, 5-hexanedione and 2, 5-furandimethanol |
| CN105859522A (en) * | 2016-04-12 | 2016-08-17 | 中国科学院广州能源研究所 | Method for preparing sugar alcohol from monosaccharide |
-
2017
- 2017-08-29 CN CN201710757968.2A patent/CN107473934B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1214333A (en) * | 1997-10-09 | 1999-04-21 | 中国石油化工总公司 | Process of hydrogenating glucose to prepare sorbierite |
| CN104370692A (en) * | 2013-08-13 | 2015-02-25 | 北京化工大学 | Polyol preparation method through glucose hydrogenolysis |
| CN105712854A (en) * | 2016-01-25 | 2016-06-29 | 中国科学技术大学先进技术研究院 | Method for selectively preparing 1-hydroxyl-2, 5-hexanedione and 2, 5-furandimethanol |
| CN105859522A (en) * | 2016-04-12 | 2016-08-17 | 中国科学院广州能源研究所 | Method for preparing sugar alcohol from monosaccharide |
Non-Patent Citations (1)
| Title |
|---|
| "半三明治型铱催化剂催化氢化葡萄糖制备山梨糖醇";龚宝祥等;《有机化学》;20171231;第37卷(第12期);3170～3176 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN107473934A (en) | 2017-12-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103007929B (en) | The Pd bases catalyst of colloidal deposition method preparation, preparation method and application | |
| CN103159606B (en) | A kind of take furfural as the method that cyclopentanone prepared by raw material | |
| CN108620127B (en) | Catalyst for preparing 1, 5-pentanediol through hydrogenolysis of tetrahydrofurfuryl alcohol, preparation method and application thereof | |
| CN109806886B (en) | Catalyst for preparing dihydroxyacetone by glycerol oxidation and preparation method and application thereof | |
| CN109453765A (en) | A kind of activated carbon supported type ruthenium catalyst and its preparation and application | |
| CN103275096A (en) | Method for preparing isosorbide based on cellulose | |
| CN110698440B (en) | Method for preparing 2, 5-furandimethanol from solvent-free 5-hydroxymethylfurfural | |
| CN108329203B (en) | Method for preparing 3-hydroxypropionic acid from glyceric acid | |
| CN109678732B (en) | Method for continuously producing 5-amino-1-pentanol | |
| CN107473934B (en) | Preparation method of sorbitol | |
| CN109678734B (en) | Method for preparing 2-methoxy ethylamine by directly catalyzing and aminating ethylene glycol monomethyl ether | |
| CN111111744A (en) | Catalyst for catalyzing furfuryl alcohol preparation reaction by furfural hydrogenation, preparation method and application thereof | |
| CN109400452A (en) | A kind of method that furan derivatives acid catalysis adds hydrogen 3- acetylpropyl alcohol and 1,4- pentanediol | |
| CN111056933A (en) | Method for preparing optically active citronellal and catalyst system used in method | |
| CN101209415B (en) | Catalyst for preparing linalyl acetate by hydrogenation of dehydrogenated linalyl acetate | |
| CN114522738B (en) | Method for preparing 1, 3-propylene glycol by one-step hydrogenation of 3-acetoxy propionaldehyde | |
| CN115739187A (en) | Supported iron-based catalyst, preparation thereof and application thereof in synthesis of (R) -citronellal | |
| CN111170840A (en) | Application of supported bifunctional catalyst in preparation of 3-acetyl propanol from furfural | |
| CN112812080B (en) | Method for preparing 2, 5-furandimethanol from 5-hydroxymethylfurfural | |
| CN110981698B (en) | Preparation method of 3-methyl-2-butenol | |
| CN112121793B (en) | Catalyst for preparing citronellal by citral hydrogenation, preparation method of catalyst, and method for preparing citronellal by citral hydrogenation | |
| CN108586194A (en) | A kind of catalyst and preparation method thereof and the application in cracking restores aryl ethers compounds | |
| CN113786837A (en) | Method for preparing cyclopentanone and cyclopentanol through furfural hydrogenation rearrangement | |
| CN111217750B (en) | Preparation method of caprolactam | |
| CN107185571B (en) | Cobalt catalyst, preparation method thereof and application thereof in catalytic synthesis of 2,3, 5-trimethylbenzoquinone |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |