CN107473934A - A kind of preparation method of sorbierite - Google Patents

A kind of preparation method of sorbierite Download PDF

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Publication number
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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preparation
sorbierite
catalyst
reactor
reaction
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CN107473934B (en
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傅尧
龚宝祥
邓晋
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University of Science and Technology of China USTC
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University of Science and Technology of China USTC
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132Preparation 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
    • C07C29/136Preparation 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
    • C07C29/14Preparation 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
    • C07C29/141Preparation 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
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22Organic complexes
    • B01J31/2282Unsaturated compounds used as ligands
    • B01J31/2295Cyclic compounds, e.g. cyclopentadienyls
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J35/00Catalysts, in general, characterised by their form or physical properties
    • B01J35/50Catalysts, in general, characterised by their form or physical properties characterised by their shape or configuration
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/60Reduction reactions, e.g. hydrogenation
    • B01J2231/64Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
    • B01J2231/641Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
    • B01J2231/643Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of R2C=O or R2C=NR (R= C, H)
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/02Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0225Complexes comprising pentahapto-cyclopentadienyl analogues
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/02Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0238Complexes 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
    • B01J2531/0241Rigid ligands, e.g. extended sp2-carbon frameworks or geminal di- or trisubstitution
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82Metals of the platinum group
    • B01J2531/827Iridium

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  • 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

A kind of preparation method of sorbierite
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。
CN201710757968.2A 2017-08-29 2017-08-29 Preparation method of sorbitol Active CN107473934B (en)

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Citations (4)

* Cited by examiner, † Cited by third party
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

Patent Citations (4)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
Title
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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