CN105712961A - Method for preparing lactone by means of oxidizing dihydric alcohol - Google Patents
Method for preparing lactone by means of oxidizing dihydric alcohol Download PDFInfo
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Abstract
The invention relates to a method for preparing lactone by means of catalytically oxidizing dihydric alcohol by the aid of heterogeneous supported metal-metal oxide catalysts under mild conditions. The method includes carrying out heterogeneous catalytic oxidation reaction by the aid of the aromatic dihydric alcohol of different substituent groups, the aliphatic dihydric alcohol, supported metal-metal oxide combinations, oxygen or air under the mild conditions with the organic solvents or without solvents to prepare the lactone. The aliphatic dihydric alcohol is used as a substrate, the supported metal-metal oxide combinations are used as the catalysts, and the oxygen or the air is used as an oxidizing agent. The method has the advantages that various shortcomings of the traditional catalysts can be overcome by the aid of catalytic systems, the catalysts are few in usage and are excellent in catalytic activity under the mild conditions and even at the normal temperature, the high catalytic activity and the high selectivity still can be kept even after the catalysts are repeatedly used, economic and environmental protection requirements can be met, the method for preparing the lactone by means of carrying out oxidation reaction on the dihydric alcohol has a broad industrial prospect, and the like.
Description
Technical field
The invention belongs to technical field of chemistry and chemical engineering, be specifically related to a kind of method that lactone is prepared in dihydroxylic alcohols oxidation.
Background technology
Lactone compound is a class Oxygenic heterocyclic compounds, has boiling point height, dissolubility is good, conductivity is high and the feature of good stability, is excellent solvent, extractant and absorbent, and is alternatively arranged as the monomer etc. of reaction reagent and synthetic macromolecular compound.Lactone compound is widely used in petrochemical industry, weaving, spice, pesticide and medicine and other fields.
The synthetic method of lactone is more, such as zinc and hydrochloric acid reduction compound anhydride method, compound anhydride hydrogenation method and glycol molecules intramolecular cyclization method etc..Wherein, at zinc with hydrochloric acid reduction compound anhydride method, environment can be caused severe contamination by a large amount of uses of hydrochloric acid, does not meet the requirement of the Green Chemistry vigorously advocated now；Although and compound anhydride hydrogenation method has been widely used in commercial production, but usually needing high temperature, high pressure, and hydrogen has certain explosion danger in transport and storage process.Therefore, the method for glycol molecules intramolecular cyclization lactone is more and more concerned.At present, existing lot of documents report is about the method for glycol molecules intramolecular cyclization lactone, mainly include direct dehydrogenation method and oxidizing process, catalyst used by direct dehydrogenation method mainly includes that Cu is catalyst based and noble metal catalyst, generally just can need to carry out under higher reaction temperatures or under the existence of hydrogen acceptor.And choice oxidation process mainly includes bioanalysis, metering oxidizing process, electrochemical process and catalytic oxidation.Wherein, bioanalysis and electrochemical process are not suitable for large-scale industrial production, and it is more serious to measure oxidizing process environmental pollution, relatively costly.Therefore, increasingly come into one's own with pollution-free and inexpensive molecular oxygen catalysis oxidizing process.During with molecular oxygen for oxidant, oxidant cost is minimum, and due to the repeatable utilization of the heterogeneous catalyst of system, significantly reduces the synthetic operation cost of technique, is the important development direction of heavy industrialization from now on.But the good catalyst of reaction effect is mainly containing a nanometer inorganic oxide material for Au granule at present.Fan Kangnian etc. are respectively in J.Catal.2007,252 (1): 69-76；J.Catal.2009,266 (2): 228-235；J.Phys.Chem.C2008,112 (41): 16110-16117 reports Au/TiO2、Au/Fe2O3With Au/Fe-A1-O catalyst for liquid phase oxidation 1,4-butanediol is butyrolactone, catalyst loadings high (3-8wt%), need in higher reaction temperature (140 DEG C), higher reaction pressure (1.25MPa), when catalyst amount relatively larger (1mol%), the catalytic effect that just can obtain.Mitsudome etc. are at GreenChem, 2009,11 (6): 793-797 report the Au/HT catalyst synthesized with brucite (HT) for carrier, it is capable of various dihydroxylic alcohols to lactonize when 40-110 DEG C, and there is extraordinary catalytic performance, overcome the problems such as reaction needed high temperature, organic additive and activity component load quantity that conventional diol lactone faces are high, but catalyst amount is also relatively larger (0.45mol%), some substrate needs the result that could obtain at a higher temperature.
Summary of the invention
It is an object of the invention to overcome the defect of prior art, there is provided that a kind of catalyst amount is few, reaction condition is gentle, operating procedure is simple, method that high activity and the selective dihydroxylic alcohols oxidation reaction of height prepare lactone, the method especially relating to metal-metallic oxide catalyst catalytic oxidation dibastic alcohol compound in a mild condition.
The method comprise the steps that with dihydroxylic alcohols, for substrate, with load type metal-metal-oxide for catalyst, oxygen or air are oxidant, and carbonate is additive, and under temperate condition, multi-phase catalytic oxidation prepares lactone.
The substrate that the present invention is suitable for is aromatic series neighbour's benzene dihydroxylic alcohols of different substituents, and fats dihydroxylic alcohols is the end position hydroxyl dihydroxylic alcohols no less than four carbon.
Substituent group involved in the present invention is selected from halogen atom, nitro, alkyl etc..
The consumption of above-mentioned substrate is 0.5-100mmol, it is preferred to 1-5mmol.
Catalyst involved in the present invention is the metal-metallic oxide catalyst of support type, including AuNiOx/HAP、AuNiOx/CeO2、AuNiOx/TiO2、AuNiOx/Fe2O3、AuNiOx/Al2O3、AuNiOx/MgO、AuNiOx/SiO2-MgO-Al2O3、AuNiOx/SiO2-MgO、AuNiOx/SiO2-Al2O3.Its preparation process adopts the method that this area researcher is familiar with, such as hydro-thermal infusion process, solid-phase synthesis, sol-gel process, liquid-phase precipitation method.The preferred hydro-thermal infusion process of the present invention.
The invention discloses gold presoma and nickel oxide presoma load at silicon dioxide composite alumina method of magnesium oxide.The present invention uses hydro-thermal infusion process, and after gained mixture filters, high-temperature heating obtains required catalyst, AuNiOx/SiO2-MgO-Al2O3, the load capacity of Au is 0.5-5wt%, it is preferable that 0.5-2wt%, and the load capacity of nickel oxide is 0.25-2.5wt%, it is preferable that 0.25-1.25wt%.
The additive used in present invention reaction is the one in potassium carbonate, sodium carbonate, cesium carbonate, lithium carbonate, it is preferable that potassium carbonate or sodium carbonate.
The consumption of carbonate additive used herein is 1-10mol%, it is preferred to 5-10mol%.
In course of reaction of the present invention, the consumption of catalyst controls at 0.01-0.5g, it is preferred that range for 0.01-0.2g.
Oxidant involved in the present invention is molecular oxygen, and oxygen source is air or purity oxygen, and in course of reaction, pressure is 1 atmospheric pressure.
The present invention both can carry out in implementation process under solvent exists situation, it is also possible to carries out under solvent-free state.Described solvent includes toluene or methanol, and solvent load is 2-20ml, and the molal volume of substrate and solvent is than for 0.05-0.5mol/L.
Preferable reaction temperature of the present invention is 25-60 DEG C.
Catalyst of the present invention, in recirculation, uses the separation Solid Method of routine, for instance by filtering or high speed centrifugation, washing is dry catalyst also.
The present invention has advantage highlighted below compared with the prior art:
This catalyst system and catalyzing can realize the dihydroxylic alcohols conversion to lactone under low catalytic amount (10-100ppm) catalyst.
This catalyst system and catalyzing at temperate condition, or even can show good catalysis activity under room temperature.
This catalyst system and catalyzing is possible not only to use at solvent existence condition, it is also possible to carry out in solvent-free situation.
This catalyst system and catalyzing is capable of the conversion to lactone of all kinds of dihydroxylic alcohols, and substrate spectrum is wide.
In this catalyst system, catalyst remains to keep high catalysis activity and selectivity after 6 recirculatioies.
Described above feature can overcome all deficiencies that traditional and existing catalyst exists, and meets economic and environment-friendly requirement, it is provided that a kind of method with industrial applications prospect.
To be described the present invention by specific embodiment in order to make it easy to understand, following.It is important to note that specific embodiment is only for explanation, it is clear that the present invention according to illustrating herein, can be made various correction and change by those of ordinary skill in the art within the scope of the invention, these are revised and change and also include the scope of the invention in.
Detailed description of the invention
Embodiment 1
With common acid-treated 200-400 order silica gel, aluminum nitrate and magnesium nitrate for initial feed, hydro-thermal, high-temperature calcination is utilized to obtain carrier material silica silicon combined oxidation aluminium magnesia, with gold chloride for gold presoma, nickel nitrate for nickel oxide precursor.Loading on carrier by infusion process, centrifugal, washing, dry repeatedly.Catalyst AuNiOx/SiO is obtained after high-temperature calcination2-MgO-Al2O3.Au load capacity is 0.57wt%, and nickel content is 0.36wt%.By 20mg catalyst (0.1mol%), 13.8mgK2CO3(10mol%), 138mg1,2-benzene dimethanol (1mmol), 4mL toluene is added sequentially in the 25mL teflon-lined autoclave pressure with stirring magneton, closed reactor, with oxygen by still pressurising power to 0.1MPa, 25 DEG C of reaction 24h acquisition crude products, chromatography, 1,2-benzene dimethanol conversion ratio 96%, selectivity of product 92%.Reactant liquor post processing: vacuum decompression rotation evaporates organic solvent, gained residue column chromatography (ethyl acetate: petroleum ether=1:42), and product separates 85%.
1HNMR(400MHz,CDCl3) δ 5.32 (s, 1H), 7.50 (d, j=7.6Hz, 1H), 7.55 (dd, j=7.6Hz, 1H), 7.70 (dd, j=7.67.4Hz, 1H), 7.4 (d, j=7.6Hz, 1H)；13CNMR(100MHz,CDCl3)δ69.60,121.98,125.62,125.75,128.96,133.89,146.42,171.06。
Embodiment 2
Catalyst preparing is embodiment 1 such as, by 20mg catalyst (0.1mol%), 13.8mgK2CO3(10mol%), 138mg1,2-benzene dimethanol (1mmol), 4mL methanol is added sequentially in the 25mL teflon-lined autoclave pressure with stirring magneton, closed reactor, with oxygen by still pressurising power to 0.1MPa, 25 DEG C of reaction 24h acquisition crude products, chromatography, 1,2-benzene dimethanol conversion ratio 98%, selectivity of product 95%.Reactant liquor post processing: vacuum decompression rotation evaporates organic solvent, gained residue column chromatography (ethyl acetate: petroleum ether=1:4), and product separates 90%.
1HNMR(400MHz,CDCl3) δ 5.32 (s, 1H), 7.50 (d, j=7.6Hz, 1H), 7.55 (dd, j=7.6Hz, 1H), 7.70 (dd, j=7.67.4Hz, 1H), 7.4 (d, j=7.6Hz, 1H)；13CNMR(100MHz,CDCl3)δ69.60,121.98,125.62,12575,128.96,133.89,146.42,171.06。
Embodiment 3
Catalyst preparing is embodiment 1 such as, by 20mg catalyst (0.1mol%), 13.8mgK2CO3(10mol%), 166mg4,5-dimethyl-1,2-benzene dimethanol (1mmol), 4mL methanol is added sequentially in the 25mL teflon-lined autoclave pressure with stirring magneton, and closed reactor, with oxygen by still pressurising power to 0.1MPa, 25 DEG C of reaction 24h obtain crude product, chromatography, 4,5-dimethyl-1,2-benzene dimethanol conversion ratio 96%, selectivity of product 95%.Reactant liquor post processing: vacuum decompression rotation evaporates organic solvent, gained residue column chromatography (ethyl acetate: petroleum ether=1:4), and product separates 85%.
1HNMR(400MHz,CDCl3) δ 2.36 (s, 3H), 2.39 (s, 3H), 5.24 (s, 2H), 7.24 (s, 1H), 7.67 (s, 1H)；13CNMR(100MHz,CDCl3)δ17.80,18.16,75.81,123.20,130.31,135.71,141.41,143.81,169.51。
Embodiment 4
Catalyst preparing is embodiment 1 such as, by 20mg catalyst (0.1mol%), 13.8mgK2CO3(10mol%), 207mg4,5-bis-chloro-1,2-benzene dimethanol (1mmol), 4mL methanol is added sequentially in the 25mL teflon-lined autoclave pressure with stirring magneton, and closed reactor, with oxygen by still pressurising power to 0.1MPa, 60 DEG C of reaction 24h obtain crude product, chromatography, 4,5-bis-chloro-1,2-benzene dimethanol conversion ratio 76%, selectivity of product 85%.Reactant liquor post processing: vacuum decompression rotation evaporates organic solvent, gained residue column chromatography (ethyl acetate: petroleum ether=1:4), and product separates 60%.
1HNMR(400MHz,CDCl3) δ 5.29 (s, 2H), 7.63 (s, 1H), 8.00 (s, 1H)；13CNMR(100MHz,CDCl3)δ75.00,125.70,128.30,131.61,132.21,146.41,169.51。
Embodiment 5
Catalyst preparing is embodiment 1 such as, by 20mg catalyst (0.1mol%), 13.8mgK2CO3(10mol%), 116mg cis-1,2-cyclohexanediol (1mmol), 4mL toluene is added sequentially in the 25mL teflon-lined autoclave pressure with stirring magneton, closed reactor, with oxygen by still pressurising power to 0.1MPa, 25 DEG C of reaction 24h acquisition crude products, chromatography, cis-1,2-cyclohexanediol conversion ratio 93%, selectivity of product 90%.Reactant liquor post processing: vacuum decompression rotation evaporates organic solvent, gained residue column chromatography (ethyl acetate: petroleum ether=1:4), and product separates 85%.
1HNMR(400MHz,CDCl3) δ 1.16-1.32 (m, 3H), 1.56-1.69 (m, 3H), 1.74-1.87 (m, 1H), 2.06-2.12 (m, 1H), 2.43-1.52 (m, 1H), 2.62-2.68 (m, 1H), 3.93 (dd, j=8.81.4Hz, 2H), 4.19 (dd, j=8.85.0Hz, 1H)；13CNMR(100MHz,CDCl3) δ 20.79,22.44,23.34,35.29,39.33,71.55,178.05.
Embodiment 6
Catalyst preparing is embodiment 1 such as, by 20mg catalyst (0.1mol%), 13.8mgK2CO3(10mol%), 90mg1,4-butanediol (1mmol), 4mL toluene is added sequentially in the 25mL teflon-lined autoclave pressure with stirring magneton, closed reactor, with oxygen by still pressurising power to 0.1MPa, 60 DEG C of reaction 24h acquisition crude products, chromatography, 1,4-butanediol conversion ratio 90%, selectivity of product 95%.Reactant liquor post processing: vacuum decompression rotation evaporates organic solvent, gained residue column chromatography (ethyl acetate: petroleum ether=1:10), and product separates 80%.
1HNMR(400MHz,CDCl3) δ 2.23-2.32 (m, 2H), 2.48 (t, j=8.3Hz, 2H), 4.35 (t, j=7.2Hz, 2H)；13CNMR(100MHz,CDCl3)δ22.10,27.67,68.39,177.45。
Embodiment 7
Catalyst preparing is embodiment 1 such as, by 20mg catalyst (0.1mol%), 13.8mgK2CO3(10mol%), 104mg1,5-pentanediol (1mmol), 4mL toluene is added sequentially in the 25mL teflon-lined autoclave pressure with stirring magneton, closed reactor, with oxygen by still pressurising power to 0.1MPa, 60 DEG C of reaction 24h acquisition crude products, chromatography, 1,5-pentanediol conversion ratio 85%, selectivity of product 90%.Reactant liquor post processing: vacuum decompression rotation evaporates organic solvent, gained residue column chromatography (ethyl acetate: petroleum ether=1:10), and product separates 75%.
1HNMR(400MHz,CDCl3) δ 1.83-1.95 (m, 2H), 2.55 (t, j=7.0Hz, 2H), 4.34 (t, j=6.0Hz, 2H)；13CNMR(100MHz,CDCl3)δ19.02,22.25,29.74,69.28,171.05。
Embodiment 8
Catalyst preparing is embodiment 1 such as, by 20mg catalyst (0.1mol%), 13.8mgK2CO3(10mol%), 166mg1-phenyl-1,4-butanediol (1mmol), 4mL toluene is added sequentially in the 25mL teflon-lined autoclave pressure with stirring magneton, closed reactor, with oxygen by still pressurising power to 0.1MPa, 60 DEG C of reaction 24h obtain crude product, chromatography, 1-phenyl-1,4-butanediol conversion ratio 55%, selectivity of product 95%.Reactant liquor post processing: vacuum decompression rotation evaporates organic solvent, gained residue column chromatography (ethyl acetate: petroleum ether=1:4), and product separates 50%.
1HNMR(400MHz,CDCl3) δ 2.79 (t, j=7.8Hz, 2H), 3.02 (t, j=7.8Hz, 2H), 7.04-7.29 (m, 4H)；13CNMR(100MHz,CDCl3)δ26.12,28.50,121.45,125.50,126.50,128.23,133.21,149.10,168.05。
Embodiment 9
Catalyst preparing is embodiment 1 such as, by 20mg catalyst (0.1mol%), 13.8mgK2CO3(10mol%), 104mg1,4-pentanediol (1mmol), 4mL toluene is added sequentially in the 25mL teflon-lined autoclave pressure with stirring magneton, closed reactor, with oxygen by still pressurising power to 0.1MPa, 60 DEG C of reaction 24h acquisition crude products, chromatography, 1,4-pentanediol conversion ratio 86%, selectivity of product 90%.Reactant liquor post processing: vacuum decompression rotation evaporates organic solvent, gained residue column chromatography (ethyl acetate: petroleum ether=1:10), and product separates 75%.
1HNMR(400MHz,CDCl3) δ 1.42 (d, j=6.3Hz, 3H), 1.78-1.88 (m, 1H), 2.32-2.56 (m, 1H), 2.52-2.59 (m, 1H), 4.60-4.68 (m, 1H)；13CNMR(100MHz,CDCl3)δ21.10,29.06,29.67,176.90。
Claims (10)
1. the method that lactone is prepared in a dihydroxylic alcohols oxidation, it is characterised in that with dihydroxylic alcohols for substrate, with load type metal-metal-oxide for catalyst, the carbonate adding low catalytic amount is oxidant as additive, oxygen or air, under 25-100 DEG C of condition, stirring reaction 6-24h, prepares lactone.
2. method according to claim 1, it is characterised in that described dihydroxylic alcohols is aromatic diol or aliphatic dihydroxy alcohol, aromatic diol is that structural formula adopts logical formula IRepresenting substituent group with R, R is halogen, nitro or C1-C3 alkyl, and aliphatic dihydroxy alcohol is the terminal hydroxy group dihydroxylic alcohols of C4-C6.
3. method according to claim 1, it is characterised in that described catalyst is load type metal-metal oxide catalyst, wherein metal is selected from one or both in Pd, Au, and metal-oxide is selected from NiOx、BiOx, in PbO or ZnO one or more, x=1 or 1.5, the preferred NiO of metal-oxidexOr BiOx, x=1 or 1.5；
Carrier is silicon dioxide, aluminium oxide, magnesium oxide, titanium dioxide, ferrum oxide, hydroxyapatite (HAP), cerium oxide or is silicon dioxide and one or both the compound in aluminium oxide, magnesium oxide, cerium oxide, titanium oxide, and described carrier is preferably silicon dioxide and aluminium oxide and/or magnesian compound；
Described silicon dioxide is 200-400 order；
When carrier be two or more compound be composited time, support preparation method is: be first 10% HCl treatment by silicon dioxide mass concentration, again presoma corresponding for the carrier needing preparation is mixed in acid solution with silicon dioxide, acid solution is nitric acid, sintering temperature 300-600 DEG C, roasting time 3-6h, obtain carrier, carrier is prepared in system, and the mass percent of acid solution ranges for 0.5-2%；
The presoma of carrier is selected from conventional presoma；
The preparation of catalyst: metal precursor, metal oxide precursor and carrier being mixed, by infusion process, calcining heat 300-500 DEG C, roasting time 3-6h, preparing load type metal-metal-oxide is catalyst；
Metal precursor is gold chloride or Palladous chloride., and metal oxide precursor is one or both in nickel nitrate, bismuth nitrate, plumbi nitras or zinc nitrate；
Metal ranges for 0.5-5wt% in catalyst loading, and metal-oxide ranges for 0.25-2.5wt% in the loading of catalyst.
4. method according to claim 3, it is characterised in that the catalyst of preparation is preferably gold-nickel oxide/silica-magnesia-aluminium oxide (AuNiOx/SiO2-MgO-Al2O3), wherein the loading of gold is 0.5-5wt%, and the loading of nickel oxide is 0.25-2.5wt%.
5. method according to claim 3, it is characterised in that catalyst is preferably AuNiOx/HAP、AuNiOx/CeO2、AuNiOx/TiO2、AuNiOx/Fe2O3、AuNiOx/Al2O3、AuNiOx/MgO、AuNiOx/SiO2-MgO-Al2O3、AuNiOx/SiO2-MgO、AuNiOx/SiO2-Al2O3。
6. method according to claim 1, it is characterised in that adding organic solvent in reaction system, organic solvent is toluene or methanol, the molal volume of substrate and organic solvent ratio is for 0.05-0.5mol/L.
7. method according to claim 1, it is characterised in that preferable reaction temperature is 25-60 DEG C.
8. the mol ratio of method according to claim 1, it is characterised in that described carbonate additive is the one in potassium carbonate, sodium carbonate, cesium carbonate, lithium carbonate, carbonate and substrate is 1-10mol%, it is preferred to 5-10mol%.
9. method according to claim 1, it is characterised in that the mol ratio of catalyst and substrate is 0.005:1-0.05:1.
10. method according to claim 9, it is characterised in that the mol ratio of catalyst and substrate is preferably: 0.005-0.01:1.
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Cited By (1)
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| CN112264011A (en) * | 2020-11-03 | 2021-01-26 | 厦门大学 | Gold-based catalyst for preparing carboxylic ester by oxidative esterification and application thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112264011A (en) * | 2020-11-03 | 2021-01-26 | 厦门大学 | Gold-based catalyst for preparing carboxylic ester by oxidative esterification and application thereof |
| CN112264011B (en) * | 2020-11-03 | 2022-03-25 | 厦门大学 | Gold-based catalyst for preparing carboxylic ester by oxidative esterification and application thereof |
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