A method for synthesizing 1,4:3,6-dianhydrohexitol methyl ether

A technology of dianhydrohexitol and anhydrohexose, applied in the field of synthesizing 1,4:3,6-dianhydrohexitol methyl ether, which can solve the problem of low total yield of isosorbide methyl ether and reduction of acidic catalyst Activity, inhibiting the degree of hydroxyl etherification, etc., to achieve the effect of avoiding CO2 generation, avoiding corrosion problems, and improving the degree of hydroxyl etherification

Active Publication Date: 2018-02-02
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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Problems solved by technology

However, since the direct etherification reaction of alcohol is a reversible reaction, the by-product water will seriously inhibit the etherification degree of the hydroxyl group and reduce the activity of the acidic catalyst, so the total yield of isosorbide methyl ether is not high
[0010] In summary, during the preparation of 1,4:3,6-dianhydrohexitol methyl ether, there are highly toxic halogenated hydrocarbons as methylating reagents, or corrosion problems caused by the introduction of high-concentration strong bases, or a large amount of CO 2 Many problems, such as the generation of 1,4:3,6-dianhydrohexitol methyl ether, or the low yield of etherification products, have greatly restricted the research and application of 1,4:3,6-dianhydrohexitol methyl ether. The preparation route of 6-dianhydrohexitol methyl ether and the realization of environmentally friendly catalytic etherification reaction have important scientific significance and application prospects

Method used

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  • A method for synthesizing 1,4:3,6-dianhydrohexitol methyl ether
  • A method for synthesizing 1,4:3,6-dianhydrohexitol methyl ether
  • A method for synthesizing 1,4:3,6-dianhydrohexitol methyl ether

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Experimental program
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Effect test

Embodiment 1

[0030] Put isosorbide, methyl ether compound and acidic catalyst Amberlyst-35 into a stainless steel reactor, seal the reactor, and stir magnetically at 130°C for 15 hours. Wherein, the molar ratio of methylating reagent and isosorbide is 50:1, and the mass ratio of catalyst Amberlyst-35 and isosorbide is 0.5:1. After the reactor was cooled to room temperature, the reaction solution was analyzed by gas chromatography. The conversion rate of isosorbide and the yield of methylated products were calculated according to the internal standard method of gas chromatography, expressed in mole percent (mol%).

[0031] The reaction results are shown in Table 1.

[0032] Table 1: Results of the reaction of isosorbide with methyl ether compounds.

[0033]

[0034] Wherein, the methylated products of isosorbide are 2-methoxyisosorbide (2-MMI), 5-methoxyisosorbide (5-MMI) and dimethyl isosorbide (DMI). Because the selected methyl ether compound has an active methyl group, it can be us...

Embodiment 2

[0036] Put isosorbide, 1,2-dimethoxyethane and strong acid ion exchange resin into a stainless steel reactor, seal the reactor, and react with magnetic stirring at 150°C for 3 hours. Wherein, the molar ratio of 1,2-dimethoxyethane to isosorbide is 10:1, and the mass ratio of strong acid ion exchange resin to isosorbide is 0.3:1. After the reactor was cooled to room temperature, the reaction solution was analyzed by gas chromatography. The conversion rate of isosorbide and the yield of methylated products were calculated according to the internal standard method of gas chromatography, expressed in mole percent (mol%).

[0037] The reaction results are shown in Table 2.

[0038] Table 2: The results of the reaction between isosorbide and 1,2-dimethoxyethane catalyzed by different strong acid ion exchange resins.

[0039]

[0040] The strong acid ion exchange resin has a good catalytic effect on the methylation reaction of isosorbide and 1,2-dimethoxyethane. When the conversi...

Embodiment 3

[0042] Put isosorbide, 1,2-dimethoxyethane and heteropoly acid into a stainless steel reactor, seal the reactor, and react with magnetic stirring at 150°C for 5 hours. Wherein, the molar ratio of 1,2-dimethoxyethane to isosorbide is 20:1, and the mass ratio of heteropoly acid to isosorbide is 0.2:1. After the reactor was cooled to room temperature, the reaction solution was analyzed by gas chromatography. The conversion rate of isosorbide and the yield of methylated products were calculated according to the internal standard method of gas chromatography, expressed in mole percent (mol%).

[0043] The reaction results are shown in Table 3.

[0044] Table 3: The reaction results of heteropolyacid-catalyzed isosorbide and 1,2-dimethoxyethane.

[0045]

[0046] Phosphotungsten and silicotungstic heteropolyacids have better catalytic effects on the methylation of isosorbide and 1,2-dimethoxyethane.

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Abstract

The invention discloses a method for synthesizing 1,4:3,6-dianhydrohexitol methyl ether. Using 1,4:3,6-dianhydrohexitol as the starting material, using methyl ether compound as the methylation reagent, the 1,4:3,6-dianhydrohexitol is produced by etherification in the presence of an acidic catalyst Hexitol Methyl Ether. Wherein, 1,4:3,6-dianhydrohexitol methyl ether is selected from mono- and dimethyl ethers of isosorbide, isomannide and isoidide, preferably isosorbide mono- and dimethyl ethers, and isosorbide The total yield of alcohol methyl ether can reach more than 80%. The invention adopts an environment-friendly acid catalyst, which has high catalytic efficiency, avoids the generation of a large number of halide salt by-products in the traditional etherification method, and the corrosion problem caused by strong alkali, and provides a new and efficient 1,4: A preparation route of 3,6-dianhydrohexitol methyl ether, and an environmentally friendly catalytic etherification reaction has been realized.

Description

technical field [0001] The present invention relates to a method for synthesizing 1,4:3,6-dianhydrohexitol methyl ether, in particular to a process of acidic synthesis of 1,4:3,6-dianhydrohexitol and methyl ether A method for synthesizing 1,4:3,6-dianhydrohexitol methyl ether by catalyst action. Background technique [0002] Catalytic conversion of renewable biomass resources to produce high value-added chemicals and liquid fuels is one of the important ways to reduce dependence on fossil resources such as petroleum. Because biomass and its derivatives contain abundant hydroxyl functional groups, hydroxyl derivatization has become one of the effective methods to realize the efficient utilization of biomass resources. [0003] 1,4:3,6-dianhydrohexitols (isosorbide, isomannide and isoidide), as important biomass-based diols, hexitols that can be derived from biomass, such as D-sorbitol Alcohol, D-mannitol and L-iditol, derived from intramolecular dehydration. The structural...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/04
Inventor 徐杰车鹏华路芳高进苗虹聂鑫
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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