CN107473934A - A kind of preparation method of sorbierite - Google Patents
A kind of preparation method of sorbierite Download PDFInfo
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- CN107473934A CN107473934A CN201710757968.2A CN201710757968A CN107473934A CN 107473934 A CN107473934 A CN 107473934A CN 201710757968 A CN201710757968 A CN 201710757968A CN 107473934 A CN107473934 A CN 107473934A
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- 238000002360 preparation method Methods 0.000 title claims abstract description 28
- 239000003054 catalyst Substances 0.000 claims abstract description 36
- 238000006243 chemical reaction Methods 0.000 claims abstract description 34
- 239000001257 hydrogen Substances 0.000 claims abstract description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
- 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 21
- 239000008103 glucose Substances 0.000 claims abstract description 18
- 238000010438 heat treatment Methods 0.000 claims abstract description 12
- 239000012429 reaction media Substances 0.000 claims abstract description 12
- 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
- 230000004044 response Effects 0.000 claims abstract description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 238000013019 agitation Methods 0.000 claims description 3
- 239000006481 glucose medium Substances 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 5
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 238000012360 testing method Methods 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 239000000047 product Substances 0.000 description 20
- 239000007788 liquid Substances 0.000 description 19
- 238000004128 high performance liquid chromatography Methods 0.000 description 11
- 239000007789 gas Substances 0.000 description 8
- 238000003760 magnetic stirring Methods 0.000 description 6
- 238000012797 qualification Methods 0.000 description 6
- 238000011002 quantification Methods 0.000 description 6
- 238000010792 warming Methods 0.000 description 6
- 238000007789 sealing Methods 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 241000220324 Pyrus Species 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 235000014633 carbohydrates Nutrition 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000000463 material Substances 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
- 235000021017 pears Nutrition 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002028 Biomass Substances 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- 241001507939 Cormus domestica Species 0.000 description 1
- 229910021640 Iridium dichloride Inorganic materials 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical class CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000000105 evaporative light scattering detection Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 238000007210 heterogeneous catalysis Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000000314 lubricant 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
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000013049 sediment Substances 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
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
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
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/50—Catalysts, in general, characterised by their form or physical properties characterised by their shape or configuration
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
The invention belongs to the field of chemical synthesis, more particularly to a kind of preparation method of sorbierite.Preparation method provided by the invention comprises the following steps：By glucose, catalyst and reaction medium add reactor, backward reactor be flushed with hydrogen, heating response, obtain sorbierite；The catalyst is half sandwich type iridium complex.Preparation method provided by the invention can make reaction keep higher selectivity and stability under relatively mild reaction conditions, so as to which the sorbierite for obtaining higher prepares yield using half sandwich type iridium complex as catalysts.Test result indicates that the yield that sorbierite is prepared using method provided by the invention reaches as high as 95.6%.
Description
Technical field
The invention belongs to the field of chemical synthesis, more particularly to a kind of preparation method of sorbierite.
Background technology
2004, USDOE assert that D- D-sorbites are that can be extracted from biomass 12 kinds are most important attached
One of value added chemicals, the preparation of liquid biological fuel is can be used for by the alkane derivative obtained by it.D- D-sorbites
It is a kind of important additive and intermediate as a kind of excellent commercial chemicals basic material.In pharmaceutical field, it is to close
Into ascorbic important source material, the preparation of Cernevit-12, diuretics can be applied to；It is mainly used as in cosmetics industry
Lubricant and moisture regulator.Leather, metallurgy and with can be used as in the industry such as papermaking at softening agent, adhesive and metal surface
Manage agent etc..In catering industry, D- D-sorbites exceed as a kind of critically important carbohydrate substitute, global year output
800000 tons of.In addition, it can further be degraded to a series of petroleum chemical industry downstream product, D- sorbs are greatly improved
The added value of sugar alcohol.
At present, it is more using platinum based on the main heterogeneous catalysis of glucose hydrogenation catalyst system and catalyzing reported for work, ruthenium,
Nickel is carried on the carriers such as activated carbon, metal oxide as central metal.Lazaridis(Catalysis Today 257
(2015):281-290.) the 1wt%Pt/AC catalyst that report uses realizes the height of the glucose in the case where pressing 1.6MPa compared with low hydrogen
Selective conversion, but 180 DEG C of reaction temperature is of a relatively high.Perrard(Applied Catalysis A:General,
2007,331:100-104.) the Pt/C catalyst of report is in 100 DEG C, the selectivity of 8MPa hydrogen pressure D- D-sorbites>
99.5%, but hydrogen presses through height.Lu Lin(Carbohydrate research 346.11(2011):1327-1332.) pass through leaching
Stain-formaldehyde restoring method is prepared for Ru/MCM-41 catalyst and Catalytic Hydrogenation of Glucose is studied, in 120 DEG C, 3MPa
Under conditions of reaction 1.5h obtain 90% D- D-sorbite yields, but yield is begun to decline after 1.5 hours, target product
Selectivity is gradually deteriorated.
Therefore, a kind of selectivity height, the preparation method for the sorbierite that stability is good, reaction condition is gentle are probed into, is ability
The technical barrier that domain is urgently captured.
The content of the invention
In view of this, it is an object of the invention to provide a kind of preparation method of sorbierite, this method selectivity is high, stably
Property is good, and reaction condition is gentle.
The invention provides a kind of preparation method of sorbierite, comprise the following steps：
By glucose, catalyst and reaction medium add reactor, backward reactor be flushed with hydrogen, heating response, obtain mountain
Pears alcohol；
The catalyst is half sandwich type iridium complex.
Preferably, the half sandwich type iridium complex is formula (I) architecture complexes：
Preferably, the mass ratio of the catalyst and glucose is (0.01~0.05)：1.
Preferably, the reaction medium is water.
Preferably, the amount ratio of the glucose and reaction medium is (50~150) mg：(1~3) mL.
Preferably, the pressure for being flushed with hydrogen rear reactor is 1~5MPa.
Preferably, the temperature of the reaction is 80~150 DEG C.
Preferably, the time of the reaction is 1~12h.
Preferably, the reaction is carried out under agitation.
Preferably, the rotating speed of the stirring is 500~1500 turns/min.
Compared with prior art, the invention provides a kind of preparation method of sorbierite.Preparation method provided by the invention
Comprise the following steps：By glucose, catalyst and reaction medium add reactor, backward reactor be flushed with hydrogen, heating response, obtain
To sorbierite；The catalyst is half sandwich type iridium complex.Preparation method provided by the invention is with half sandwich type iridium network
Compound can make reaction keep higher selectivity and stability under relatively mild reaction conditions as catalysts, from
And obtain higher sorbierite and prepare yield.Test result indicates that the yield of sorbierite is prepared using method provided by the invention
Reach as high as 95.6%.
Brief description of the drawings
In order to illustrate more clearly about the embodiment of the present invention or technical scheme of the prior art, below will be to embodiment or existing
There is the required accompanying drawing used in technology description to be briefly described, it should be apparent that, drawings in the following description are only this
The embodiment of invention, for those of ordinary skill in the art, on the premise of not paying creative work, can also basis
The accompanying drawing of offer obtains other accompanying drawings.
Fig. 1 is the hydrogen nuclear magnetic resonance spectrogram of catalyst provided in an embodiment of the present invention；
Fig. 2 is the carbon-13 nmr spectra figure of catalyst provided in an embodiment of the present invention；
Fig. 3 is the HPLC figures for the reaction product that the embodiment of the present invention 1 provides.
Embodiment
The technical scheme in the embodiment of the present invention is clearly and completely described below, it is clear that described embodiment
Only part of the embodiment of the present invention, rather than whole embodiments.Based on the embodiment in the present invention, the common skill in this area
The every other embodiment that art personnel are obtained under the premise of creative work is not made, belong to the model that the present invention protects
Enclose.
The invention provides a kind of preparation method of sorbierite, comprise the following steps：
By glucose, catalyst and reaction medium add reactor, backward reactor be flushed with hydrogen, heating response, obtain mountain
Pears alcohol；
The catalyst is half sandwich type iridium complex.
In the present invention, it is preferred to glucose, catalyst and reaction medium are added into reactor.Wherein, the catalyst is
Half sandwich type iridium complex, preferably formula (I) architecture complexes：
In the present invention, the reaction medium is preferably water；The mass ratio of the catalyst and glucose is preferably (0.01
~0.05)：1, more preferably 0.02：1；The amount ratio of the glucose and reaction medium is preferably (50~150) mg：(1~3)
ML, more preferably 100mg：2mL.
Backward reactor be flushed with hydrogen, the pressure for being flushed with hydrogen rear reactor is preferably 1~5MPa, more preferably 2~3MPa.At this
In invention, in order to ensure not having in reactor other gases, preferably first with the gas in hydrogen replacement reaction kettle for several times, Ran Hou
It is flushed with hydrogen and requires pressure.
After being flushed with hydrogen, reactor is heated, reacted.Wherein, the heating rate of the reactor is preferably 5~15
DEG C/min, more preferably 10 DEG C/min；The temperature of the reaction is preferably 80~150 DEG C, more preferably 100~120 DEG C；It is described
The time of reaction is preferably 1~12h, more preferably 2~6h.In the present invention, the time of the reaction refers to that reactor heats up
The time terminated after the temperature required to reaction to reaction.In the present invention, the reaction is carried out under agitation；It is described to stir
The rotating speed mixed is 500~1500 turns/min, more preferably 900 turns/min.After reaction terminates, sorbierite is obtained.
Preparation method provided by the invention, can be relatively mild using half sandwich type iridium complex as catalysts
Reaction is set to keep higher selectivity and stability under reaction condition, so as to which the sorbierite for obtaining higher prepares yield.Experiment knot
Fruit shows that the yield that sorbierite is prepared using method provided by the invention reaches as high as 95.6%.
For the sake of becoming apparent from, it is described in detail below by following examples.
In following embodiments, used catalyst is formula (I) architecture complexes, and preparation process includes：By 0.6mmol [Cp*
IrCl2]2And 1.2mmolAg2SO4It is added to together in 5mL deionized waters, 10h is stirred at room temperature in solution, by sediment AgCl
It is filtered to remove, solution vacuum is spin-dried for, obtains [Cp*Ir (H2O)3]SO4Solid powder.With 10mL water by 0.1mmol [Cp*Ir
(H2O)3]SO4Dissolving, 0.1mmol bipyridine ligands are added under argon atmosphere, 12h is stirred at room temperature, solution vacuum is spin-dried for, obtained
The solid arrived is vacuum dried, obtains final catalyst.
NMR (nuclear magnetic resonance) analyses are carried out to the catalyst of above-mentioned preparation, as a result as illustrated in fig. 1 and 2, Fig. 1 is the present invention
The hydrogen nuclear magnetic resonance spectrogram for the catalyst that embodiment provides, Fig. 2 is the nuclear magnetic resonance carbon of catalyst provided in an embodiment of the present invention
Spectrogram, can be seen that catalyst provided in an embodiment of the present invention by Fig. 1 and Fig. 2 has formula (I) structure.
In following embodiments, so reaction vessel is stainless steel autoclave (PARR, 0.01L).
In following embodiments, qualitative and quantitative detecting instrument is as follows：High performance liquid chromatography (HPLC) is Hitachi L-2000, liquid
Phase chromatographic column is Cosmosil Sugar-D, and detector is that Alltech ELSD 2000ES evaporate photodetector；Liquid-phase condition：
SUGAR SH1011 posts, mobile phase：Water, flow velocity：0.5ml/min, column temperature：50℃.
Embodiment 1
Sorbierite is prepared according to following course of reaction：
Specially：100mg glucose is weighed with 2mg catalyst in being mixed in reactor, adds 2mL water, sealing reaction
Kettle, then pass to 3MPa hydrogen with gas in hydrogen replacement reaction kettle three times, seal.Reactor is placed in magnetic stirring apparatus
On, turn on agitator to rotating speed is 900 turns/min, is warming up to 120 DEG C with 10 DEG C/min heating rate and maintains 6h.Question response
After end, room temperature is cooled to, collects product liquid.
Quantification and qualification is carried out by HPLC (high performance liquid chromatography), as a result as shown in figure 3, Fig. 3 is of the invention real
The HPLC figures of the reaction product of the offer of example 1 are provided.The content of sorbierite in product liquid is obtained according to HPLC profiling results, further according to
The yield of the sorbierite of the present embodiment is calculated in the content of sorbierite and sorbierite theoretical yield in product liquid, as a result for：
95.6%.
It can be seen from above-mentioned analysis mode, the yield in the present invention refers to the yield of sorbierite sterling.
Embodiment 2
100mg glucose is weighed with 1mg catalyst in being mixed in reactor, 2mL water is added, seals reactor, use hydrogen
Gas three times, then passes to 3MPa hydrogen in gas replacement reaction kettle, sealing.Reactor is placed on magnetic stirring apparatus, opened
Agitator to rotating speed is 900 turns/min, is warming up to 120 DEG C with 10 DEG C/min heating rate and maintains 6h.After question response terminates,
Room temperature is cooled to, collects product liquid.
Quantification and qualification is carried out by HPLC, obtains the content of sorbierite in product liquid；According in product liquid
The yield of the sorbierite of the present embodiment is calculated in the content and sorbierite theoretical yield of sorbierite, as a result for：86.5%.
Embodiment 3
100mg glucose is weighed with 2mg catalyst in being mixed in reactor, 2mL water is added, seals reactor, use hydrogen
Gas three times, then passes to 2MPa hydrogen in gas replacement reaction kettle, sealing.Reactor is placed on magnetic stirring apparatus, opened
Agitator to rotating speed is 900 turns/min, is warming up to 120 DEG C with 10 DEG C/min heating rate and maintains 6h.After question response terminates,
Room temperature is cooled to, collects product liquid.
Quantification and qualification is carried out by HPLC, obtains the content of sorbierite in product liquid；According in product liquid
The yield of the sorbierite of the present embodiment is calculated in the content and sorbierite theoretical yield of sorbierite, as a result for：72.8%.
Embodiment 4
100mg glucose is weighed with 2mg catalyst in being mixed in reactor, 2mL water is added, seals reactor, use hydrogen
Gas three times, then passes to 3MPa hydrogen in gas replacement reaction kettle, sealing.Reactor is placed on magnetic stirring apparatus, opened
Agitator to rotating speed is 900 turns/min, is warming up to 100 DEG C with 10 DEG C/min heating rate and maintains 6h.After question response terminates,
Room temperature is cooled to, collects product liquid.
Quantification and qualification is carried out by HPLC, obtains the content of sorbierite in product liquid；According in product liquid
The yield of the sorbierite of the present embodiment is calculated in the content and sorbierite theoretical yield of sorbierite, as a result for：50.6%.
Embodiment 5
100mg glucose is weighed with 2mg catalyst in being mixed in reactor, 2mL water is added, seals reactor, use hydrogen
Gas three times, then passes to 3MPa hydrogen in gas replacement reaction kettle, sealing.Reactor is placed on magnetic stirring apparatus, opened
Agitator to rotating speed is 900 turns/min, is warming up to 120 DEG C with 10 DEG C/min heating rate and maintains 2h.After question response terminates,
Room temperature is cooled to, collects product liquid.
Quantification and qualification is carried out by HPLC, obtains the content of sorbierite in product liquid；According in product liquid
The yield of the sorbierite of the present embodiment is calculated in the content and sorbierite theoretical yield of sorbierite, as a result for：38.2%.
Embodiment 6
100mg glucose is weighed with 2mg catalyst in being mixed in reactor, 2mL isopropanols is added, seals reactor,
With gas in hydrogen replacement reaction kettle three times, 3MPa hydrogen is then passed to, sealed.Reactor is placed on magnetic stirring apparatus,
Turn on agitator to rotating speed is 900 turns/min, is warming up to 120 DEG C with 10 DEG C/min heating rate and maintains 6h.Question response knot
Shu Hou, room temperature is cooled to, collects product liquid.
Quantification and qualification is carried out by HPLC, obtains the content of sorbierite in product liquid；According in product liquid
The yield of the sorbierite of the present embodiment is calculated in the content and sorbierite theoretical yield of sorbierite, as a result for：25.3%.
Described above is only the preferred embodiment of the present invention, it is noted that for the ordinary skill people of the art
For member, under the premise without departing from the principles of the invention, some improvements and modifications can also be made, these improvements and modifications also should
It is considered as protection scope of the present invention.
Claims (10)
1. a kind of preparation method of sorbierite, comprises the following steps：
By glucose, catalyst and reaction medium add reactor, backward reactor be flushed with hydrogen, heating response, obtain sorbierite；
The catalyst is half sandwich type iridium complex.
2. preparation method according to claim 1, it is characterised in that the half sandwich type iridium complex is tied for formula (I)
Structure complex compound：
3. preparation method according to claim 1, it is characterised in that the mass ratio of the catalyst and glucose is
(0.01~0.05)：1.
4. preparation method according to claim 1, it is characterised in that the reaction medium is water.
5. preparation method according to claim 1, it is characterised in that the amount ratio of the glucose and reaction medium is
(50~150) mg：(1~3) mL.
6. preparation method according to claim 1, it is characterised in that the pressure for being flushed with hydrogen rear reactor is 1~5MPa.
7. preparation method according to claim 1, it is characterised in that the temperature of the reaction is 80~150 DEG C.
8. preparation method according to claim 7, it is characterised in that the time of the reaction is 1~12h.
9. preparation method according to claim 1, it is characterised in that the reaction is carried out under agitation.
10. preparation method according to claim 9, it is characterised in that the rotating speed of the stirring be 500~1500 turns/
min。
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| 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 |
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| 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 |
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| 龚宝祥等: ""半三明治型铱催化剂催化氢化葡萄糖制备山梨糖醇"", 《有机化学》 * |
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