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Synthesis method of cyclohexanol derivative 1-methyl-1, 2-cyclohexanediol

A synthesis method and technology of cyclohexanediol, which is applied in the field of catalytic conversion and utilization of biomass resources, can solve the problems of high catalyst requirements and harsh reaction conditions, and achieve the effects of excellent reaction effect, easy reaction steps and mild reaction conditions

Active Publication Date: 2020-06-09
HEBEI UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In the existing experimental research, guaiacol can undergo hydrodeoxygenation under the catalysis of a catalyst to obtain aromatic hydrocarbons or alkanes. Zhou Minghao et al. used Ni / Co catalyst, water as solvent, and at 200 °C, the initial hydrogen pressure 5Mpa, made cyclohexanol, Dmitry Yu Ermakov used NiCu / CeO 2 -ZrO 2 Catalyst, get guaiacol and catalyst in reactor at 320 ℃ and initial hydrogen pressure 17MPa, the productive rate of making 1-methyl-1,2 cyclohexanediol is only 27%, many experiments show that reaction The required pressure is generally above 5MPa, the temperature is above 200°C, the reaction conditions are relatively harsh, or the requirements for the catalyst are high, and the reaction conditions are harsh. Therefore, it is imminent to seek a reaction with mild reaction conditions and high product utilization value.

Method used

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  • Synthesis method of cyclohexanol derivative 1-methyl-1, 2-cyclohexanediol
  • Synthesis method of cyclohexanol derivative 1-methyl-1, 2-cyclohexanediol
  • Synthesis method of cyclohexanol derivative 1-methyl-1, 2-cyclohexanediol

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] (1) Prepare carbon carrier from biomass tar: Weigh 20g of carbon precursor biomass tar and dissolve it in 100ml absolute ethanol, and then add 100ml 0.2mol / L activator KOH aqueous solution dropwise to the biomass tar ethanol solution. Stir in a water bath at °C for 8 hours until a uniform solid is formed, and then dry at 100 °C for 12 hours to obtain a solid mixture. Grind the solid mixture into uniform fine powder, put it in a tube furnace, heat up to 800°C at 1°C / min in a nitrogen atmosphere, and calcine for 2h. After cooling to room temperature, use HCl (1M, 100ML) to condense and reflux the sample in a water bath environment for 10 hours, then rinse with deionized water twice and ethanol for three times. Finally, vacuum drying was carried out at 100°C for 12 hours to prepare a low-cost carbon support.

[0044] The preparation of the catalyst, load the metal element nickel with a mass fraction of 10%: 1.1010g Ni(NO 3 ) 2 ·6H 2 O is dissolved in 250ml of deionized water...

Embodiment 2

[0046] (1) Prepare carbon carrier with biomass tar: weigh 20g of carbon precursor biotar and dissolve in 100ml of absolute ethanol, and then add 100ml of 0.1mol / L activator K 2 FeO 4 The aqueous solution was added dropwise to the biological tar solution, stirred in a water bath at 60°C for 8 hours until a uniform solid, and then dried at 100°C for 12 hours to obtain a solid mixture. Grind the solid mixture into a uniform fine powder, put it in a tube furnace, and calcine at 800°C for 2h in a nitrogen atmosphere. After cooling to room temperature, use HCl (1mol / L, 100mL) to condense and reflux the sample in a water bath environment for 10 hours, then rinse with deionized water twice and ethanol for three times. Finally, vacuum drying was carried out at 100°C for 12 hours to prepare a low-cost carbon support.

[0047] The preparation of the catalyst: load the metal element nickel with a mass fraction of 10%, add 1.1010g Ni(NO 3 ) 2 ·6H 2 O is dissolved in 250ml of deionized water, ...

Embodiment 3

[0049] Add 0.2g of guaiacol, 20ml of dodecane, and 0.1g of the 10wt% nickel catalyst obtained in Example 1 into the reactor at the same time, add 2MPa hydrogen gas, stir with the magnet, 600r / min, adjust The reaction temperature was 180°C, 190°C, 220°C, 260°C, and the reaction time was 2 hours. The results are shown in Table 1.

[0050] Table 1 Yield of 1-methyl-1,2-cyclohexanediol

[0051] Reaction temperature (℃) Yield of 1-methyl-1,2-cyclohexanediol (%) 22077.6

[0052] From figure 1 Analyzed by the gas chromatography-mass spectrogram, the detected substance has the highest similarity with 1-methyl-1,2-cyclohexanediol, and passed figure 2 Examination of the gas chromatogram showed the presence of double peaks on both spectra, which confirmed that the reaction produced 1-methyl-1,2-cyclohexanediol. The double peaks were due to 1-methyl The presence of cis and trans isomers of 1,2-cyclohexanediol was detected by gas chromatography at the same time, and the internal standard m...

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Abstract

The invention relates to a cyclohexanol derivative 1-methyl-1, 2-cyclohexanediol synthesis method, which comprises: mixing guaiacol and an organic solvent, adding the obtained mixture and a Ni / C catalyst to a reaction kettle, introducing hydrogen gas with a pressure of 1-3 MPa, stirring, and carrying out a heating reaction for 1-3 h at a temperature of 180-260 DEG C; wherein the Ni / C catalyst is anickel-loaded green catalyst taking biomass tar as a carrier. According to the method, synthesis of 1-methyl-1, 2-cyclohexanediol can be achieved in one step, the atom utilization rate reaches 100%,the method has very high conversion rate and selectivity, and the green and energy-saving aims are achieved.

Description

Technical field [0001] The invention belongs to the field of catalytic conversion and utilization of biomass resources, and specifically relates to a method for preparing cyclohexanol derivatives 1-methyl-1,2-cyclohexanediol through efficient conversion of bio-based guaiacol. Background technique [0002] There are many ways to use biomass energy. Among them, rapid biomass pyrolysis technology can quickly and efficiently obtain a large amount of liquid products, so it is considered to be the most effective way to use biomass energy. However, compared with traditional fossil fuels, the quality of bio-oil prepared by rapid thermal cracking technology is poor, with high viscosity, high oxygen content, strong polarity, low calorific value, high acidity, strong corrosion, and poor stability. It is difficult to directly use as internal combustion engine fuel and must be refined and refined before it can be used as high-quality fuel. Through catalytic hydrorefining, the phenol derivati...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C31/27C07C29/56C07C29/19B01J23/755B01J37/16B01J37/08
CPCC07C29/56C07C29/19B01J23/755B01J37/036B01J37/16B01J37/088C07C2601/14C07C2523/755C07C31/276Y02P30/20
Inventor 李浩王思琪
Owner HEBEI UNIV OF TECH
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