CN116178143B - A 1,4-naphthalene dicarboxylic acid/ester, a 1,4-naphthalene dicarboxylic acid derivative, and a preparation method and application thereof - Google Patents

Abstract

The present application discloses a 1,4-naphthalene dicarboxylic acid/ester, a 1,4-naphthalene dicarboxylic acid derivative, and a preparation method and application thereof. It has a structure shown in Formula I or Formula II: Wherein, X or Y is independently selected from one of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl; R is a hydrogen atom or a hydroxyl group. The compound having the structure shown in formula II is obtained by hydrolyzing the compound according to claim 1.

Description

A 1,4-naphthalene dicarboxylic acid/ester, a 1,4-naphthalene dicarboxylic acid derivative, and its preparation method and application

Technical Field

The invention relates to the fields of chemistry, chemical engineering, energy and polymer science, and in particular to 1,4-naphthalenedicarboxylic acid, 1,4-naphthalenedicarboxylic acid derivatives and preparation methods and applications thereof.

Background Art

1,4-Naphthalene dicarboxylic acid/ester can be used to manufacture high-performance polyester fibers, insulating materials, fluorescent brighteners, dye intermediates, liquid crystal materials, etc. Its derivative 5,8-dihydroxy-1,4-naphthalene dicarboxylic acid/ester is a new compound with both carboxylic acid groups and phenolic hydroxyl groups, which can be used as a monomer for synthesizing high-performance polymers and a ligand for new metal framework materials. At present, several preparation processes of 1,4-naphthalenedicarboxylic acid have been reported at home and abroad: 1,4-dimethylnaphthalene is used as a raw material, and 1,4-naphthalenedicarboxylic acid is obtained by liquid phase oxidation with oxygen under the action of cobalt acetate-manganese acetate-potassium bromide catalyst and cocatalyst zirconium acetate (JP06345685, CN113461511 A); naphthalene is used as a starting material, and 1,4-dibromonaphthalene is firstly obtained by bromination, and then reacted with cuprous cyanide in dimethylformamide solvent to obtain 1,4-dicyanonaphthalene, and further hydrolyzed under sulfuric acid catalysis to obtain 1,4-naphthalenedicarboxylic acid (US4375556A, US4376214A); 1-methyl-4-naphthalenecarboxylic acid is used as a raw material, glacial acetic acid is used as a solvent, and 1,4-naphthalenedicarboxylic acid is obtained by air oxidation under the catalysis of cobalt acetate-manganese acetate-sodium acetate (CN103739484 A); 1-methyl-4-naphthyl acetonide is used as a raw material, glacial acetic acid is used as a solvent, and cobalt acetate-manganese acetate-potassium bromide is used as a catalyst to oxidize with oxygen to obtain 1,4-naphthalene dicarboxylic acid (CN111747840 A); 1-bromonaphthalene is used as a starting material, and acetyl chloride is reacted with Friedel-Crafts acylation to generate 4-bromo-1-acetylnaphthalene, which is then oxidized with hypochlorite to obtain 4-bromo-1-naphthalene dicarboxylic acid; 4-bromo-1-naphthalene dicarboxylic acid reacts with cuprous cyanide in a polar aprotic solvent in the presence of catalytic amounts of potassium iodide and copper sulfate to generate a 4-cyanonaphthoic acid copper salt complex; the 4-cyanonaphthoic acid copper salt complex is hydrolyzed with alkali to obtain 1,4-naphthalene dicarboxylic acid (CN112778116 A). The above processes are all limited by the supply of raw materials, and the process requires the use of a large amount of highly polluting compounds such as halides. In addition, there is no literature report on the preparation of 5,8-dihydroxy-1,4-naphthalene dicarboxylic acid/ester. Therefore, it is urgent to develop a green and sustainable preparation method of 1,4-naphthalene dicarboxylic acid/ester and its derivative 5,8-dihydroxy-1,4-naphthalene dicarboxylic acid/ester.

Summary of the invention

The present invention aims to provide a process route for preparing 1,4-naphthalene dicarboxylic acid/ester and its derivative 5,8-dihydroxy-1,4-naphthalene dicarboxylic acid/ester by multi-step reaction of biomass-based raw materials trans, trans-muconic acid diester and p-benzoquinone.

According to one aspect of the present application, a compound is provided, wherein the compound is selected from one of the compounds having a structure shown in Formula I:

wherein X or Y is independently selected from one of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl;

R is a hydrogen atom or a hydroxyl group.

According to one aspect of the present application, a compound is provided, wherein the compound is selected from one of the compounds having a structure shown in Formula II:

Wherein, R is a hydrogen atom or a hydroxyl group;

The compound having the structure shown in Formula II is obtained by hydrolyzing the compound according to claim 1.

According to another aspect of the present application, a method for preparing the above-mentioned compound is provided, comprising at least the following steps:

(1) mixing a raw material containing a compound having a structure represented by Formula III and p-benzoquinone with a catalyst I and a solvent, and performing a reaction I to obtain a mixture I;

(2) mixing the mixture I obtained in (1) with the catalyst II, and reacting II to obtain a compound having a structure shown in formula I;

Preferably, the reaction I is a tandem reaction of a Diels-Alder cycloaddition reaction and a dehydrogenation reaction;

The reaction II is a hydrogenation reaction; further, the reaction II includes a dehydration reaction; further, the reaction II includes a hydrolysis reaction. That is, the reaction II includes two routes, hydrogenation dehydration, hydrolysis or hydrogenation, hydrolysis.

(1), the solvent is selected from an alcohol solvent or an ester solvent;

Optionally, the alcohol solvent is selected from at least one of methanol, ethanol, propanol, n-butanol and isopropanol;

Optionally, the ester solvent is selected from at least one of methyl acetate, ethyl acetate, propyl acetate, butyl acetate or isopropyl acetate;

Optionally, the catalyst I is a cycloaddition reaction catalyst;

Optionally, the catalyst I is selected from at least one of acidic molecular sieves;

Optionally, the catalyst I is selected from at least one of HY, Hβ, Snβ, HZSM-5, USY or SAPO-34.

The molar ratio of the compound having the structure shown in Formula III to p-benzoquinone is 1/20 to 10/1;

Optionally, the molar ratio of the compound of the structure described in Formula III to p-benzoquinone is 1/10 to 2/1;

Further optionally, the molar ratio of the compound of the structure described by formula III to p-benzoquinone is 1/5 to 1/1.

The mass ratio of the compound having the structure represented by Formula III to the solvent is 1/100 to 50/100;

Optionally, the mass ratio of the compound having the structure shown in Formula III to the solvent is 5/100 to 40/100;

Further optionally, the mass ratio of the compound having the structure represented by Formula III to the solvent is 10/100 to 30/100;

The mass ratio of the catalyst I to the compound having the structure shown in formula III is 1/100 to 100/100;

Optionally, the mass ratio of the catalyst I to the compound having the structure shown in formula III is 5/100 to 60/100;

Further optionally, the mass ratio of the catalyst I to the compound having the structure represented by formula III is 8/100 to 20/100.

The temperature of the reaction I is 50-300°C; optionally, the temperature of the reaction I is 100-220°C; further optionally, the temperature of the reaction I is 120-160°C;

The reaction time of the reaction I is 0.5 to 24 hours; optionally, the reaction time of the reaction I is 1 to 16 hours; further optionally, the reaction time of the reaction I is 2 to 10 hours.

The reaction 1 is stirred;

(2), the catalyst II is a hydrogenation reaction catalyst;

Optionally, the catalyst II is a supported metal/acid bifunctional catalyst;

Optionally, the supported metal/acid bifunctional catalyst comprises an acidic molecular sieve and a metal active component;

Optionally, the metal active component is selected from at least one of Ni, Ru, Pd and Pt;

Optionally, the acidic molecule is selected from at least one of HY, Hβ, Snβ, and HZSM-5;

Optionally, the catalyst II is selected from at least one of Ni/HY, Ni/Hβ, Ni/Snβ, Ni/HZSM-5, Ru/HY, Ru/Hβ, Ru/Snβ, Ru/HZSM-5, Pd/HY, Pd/Hβ, Pd/Snβ, Pd/HZSM-5, Pt/HY, Pt/Hβ, Pt/Snβ, Pt/HZSM-5;

The molar ratio of the metal active component in the catalyst II to the compound having the structure shown in formula III is 1/2000 to 1/50;

Optionally, the molar ratio of the metal active component in the catalyst II to the compound having the structure shown in formula III is 1/1000 to 1/100;

Further optionally, the molar ratio of the metal active component in the catalyst II to the compound having the structure shown in formula III is 1/500 to 1/200.

When reaction II is a hydrogenation dehydration reaction, the reaction conditions are A, and the compound having the structure shown in formula I is obtained, wherein R is a hydroxyl group;

The condition A includes:

The atmosphere of the reaction II is a hydrogen atmosphere;

The pressure of the reaction II is 1 to 50 bar; optionally, the pressure of the reaction II is 1 to 25 bar; further optionally, the pressure of the reaction II is 2 to 10 bar;

The temperature of the reaction II is 25 to 120°C; alternatively, the temperature of the reaction II is 25 to 100°C; further alternatively, the temperature of the reaction II is 25 to 60°C;

The time of the reaction II is 0.5 to 24 hours; optionally, the time of the reaction II is 1 to 16 hours; further optionally, the time of the reaction II is 5 to 10 hours.

When reaction II is a hydrogenation reaction, the reaction conditions are B; the obtained compound having the structure shown in formula I has R as a hydrogen atom;

The condition B includes:

The atmosphere of the reaction II is a hydrogen atmosphere;

The pressure of the reaction II is 5 to 150 bar; optionally, the pressure of the reaction II is 10 to 100 bar; further optionally, the pressure of the reaction II is 30 to 60 bar;

The temperature of the reaction II is 150-300°C; optionally, the temperature of the reaction II is 180-280°C; further optionally, the temperature of the reaction II is 200-240°C;

The time of the reaction II is 0.5 to 30 hours; optionally, the time of the reaction II is 1 to 24 hours; further optionally, the time of the reaction II is 5 to 12 hours.

According to another aspect of the present application, a method for preparing the above-mentioned compound is provided, wherein the compound is obtained by hydrolyzing one of the above-mentioned compounds having the structure shown in Formula I;

The hydrolysis process comprises mixing a compound having a structure shown in Formula I with an alkaline solution;

The alkali in the alkaline solution is selected from at least one of sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate or potassium bicarbonate;

The molar ratio of the alkali in the alkali solution to the compound having the structure shown in Formula I is 6:1 to 1:1;

The hydrolysis temperature is 50-200°C;

The hydrolysis time is 1 to 20 hours.

Specifically, the preparation process is as follows:

Taking trans-dimethyl muconate as an example, the reaction process is shown in Figure 5

Step (1), add the reaction raw materials of trans, trans-muconate and p-benzoquinone in a molar ratio of 1/20 to 10/1, an alcohol or ester reaction solvent (the mass ratio of trans, trans-muconate to the solvent is 1/100 to 50/100), and an acidic molecular sieve catalyst (the mass ratio of molecular sieve to trans, trans-muconate is 1/100 to 10/100) to a stainless steel autoclave lined with polytetrafluoroethylene in sequence, control the reaction temperature to 50 to 300° C. under a nitrogen atmosphere, and the reaction time is 0.5 to 24 hours. After the reaction is completed, cool to room temperature, filter to remove the catalyst, and remove the solvent by rotary evaporation. The product 5,8-naphthoquinone-1,4-dicarboxylic acid dimethyl ester is obtained by column chromatography. By optimizing the process conditions, trans, trans- The conversion rate of muconic acid diester can reach more than 99%, and the selectivity of the product 5,8-naphthoquinone-1,4-dicarboxylic acid dimethyl ester can reach more than 95%; step (2), first, a certain amount of 5,8-naphthoquinone-1,4-dicarboxylic acid dimethyl ester, a reaction solvent alcohol or ester, and a metal/acid bifunctional catalyst (the molar ratio of the metal active component to the substrate is 1/2000 to 1/50) are sequentially added to a stainless steel high-pressure reactor with a polytetrafluoroethylene liner, and hydrogen replaces the gas in the reactor five times. , fill with 1-50 bar hydrogen, control the reaction temperature at 25-120°C, carry out hydrogenation reaction for 0.5-24 hours, and the product is 5,8-dihydroxy-1,4-naphthalene dicarboxylic acid diester; or fill with hydrogen pressure of 5-150 bar, control the reaction temperature at 150-300°C, carry out hydrodeoxygenation reaction for 0.5-30 hours, and the product is 1,4-naphthalene dicarboxylic acid diester; secondly, add a certain amount of 1 mol of the reaction liquid after the above hydrogenation or hydrodeoxygenation reaction L ^-1 sodium hydroxide solution (the molar ratio of sodium hydroxide to substrate is 6/1 to 1/1), a sealed reactor, a nitrogen atmosphere, the reaction temperature is controlled at 50-200° C., the hydrolysis reaction is carried out for 1 to 20 hours, stirring is stopped, the reactor is naturally cooled to room temperature, the catalyst added in step II is filtered out, the reaction solution is neutralized with dilute acid, and then the reaction solution is extracted with ethyl acetate several times, the organic phase is dried with anhydrous sodium sulfate overnight, and the solvent is removed by rotary evaporation to obtain solid products 5,8-dihydroxy-1,4-naphthalene dicarboxylic acid and 1,4-naphthalene dicarboxylic acid.

According to another aspect of the present application, there is provided an application of the above-mentioned compound or the compound prepared by the above-mentioned preparation method, which is used to manufacture high-performance polyester fibers, insulating materials, fluorescent brighteners, dye intermediates, liquid crystal materials, or as a monomer for synthesizing high-performance polymers and a ligand for new metal frame materials.

The beneficial effects of this application are:

1. The 1,4-naphthalene dicarboxylic acid/ester prepared by the present invention adopts a synthetic route using a compound having a structure shown in Formula II as a raw material. Compared with the original synthetic route, the raw materials used in the present invention can be derived from biomass resources, which can reduce dependence on petroleum resources.

2. The 5,8-dihydroxy-1,4-naphthalene dicarboxylic acid/ester prepared by the present invention is a new compound that cannot be found in the existing database and has original innovation.

3. The method of the present invention can adopt a one-pot multi-step method, that is, the compound having the structure shown in Formula II and p-benzoquinone undergo a Diels-Alder cycloaddition reaction and a dehydrogenation tandem reaction, after simple catalyst separation, a metal/acid bifunctional catalyst is added to carry out hydrogenation or hydrodeoxygenation reaction, and finally a hydrolysis reaction is carried out. By controlling the process conditions, the target products 1,4-naphthalenedicarboxylic acid and 5,8-dihydroxy-1,4-naphthalenedicarboxylic acid can be obtained in high yield. The method has mild conditions and the process is green and sustainable.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG1 is a nuclear magnetic resonance spectrum of the product 5,8-naphthoquinone-1,4-dicarboxylic acid dimethyl ester in Example 1;

FIG2 is a nuclear magnetic resonance spectrum of the product 1,4-dimethyl naphthalene dicarboxylate in Example 1;

FIG3 is a nuclear magnetic resonance spectrum of the product 1,4-naphthalene dicarboxylic acid in Example 1;

FIG4 is a nuclear magnetic resonance spectrum of dimethyl 5,8-dihydroxy-1,4-naphthalenedicarboxylate in Example 2;

FIG5 shows the reaction process of the technical solution of the present application, taking trans, trans-dimethyl muconate as an example.

DETAILED DESCRIPTION

The present application is described in detail below with reference to embodiments, but the present application is not limited to these embodiments.

Unless otherwise specified, the raw materials and catalysts in the examples of this application were purchased through commercial channels.

The analysis method in the examples of this application is as follows:

The products were qualitatively analyzed by gas chromatography-mass spectrometry, and quantitatively analyzed by gas chromatography internal standard method.

In the examples of this application, the conversion rate and selectivity are calculated as follows:

The selectivity of each product is calculated according to the feed amount of trans-trans-muconic acid diester, that is, the calculation formula of the reactant conversion rate and the selectivity of each product is as follows:

The following examples will help to understand the present invention, but the present invention is not limited thereto.

(1) mixing a raw material containing a compound having a structure represented by Formula II and p-benzoquinone with a catalyst I and a solvent, and performing a reaction I to obtain a mixture I;

(2) Mixing the mixture I obtained in (1) with the catalyst II, and performing reaction II to obtain a compound having the structure shown in formula I.

Example 1 Synthesis and purification of 1,4-naphthalenedicarboxylic acid

In a 500 mL autoclave with a polytetrafluoroethylene liner, 17.00 g of trans, trans-dimethyl muconate, 32.40 g of p-benzoquinone, 170.00 g of methanol reaction solvent and 1.70 g of Snβ catalyst (the molar ratio of Snβ to trans, trans-dimethyl muconate is 10/100) were added in sequence, stirred and mixed uniformly at room temperature, and then heated to 160° C. by electric heating under a nitrogen atmosphere, and reacted for 8 hours under magnetic stirring at 1000 rpm. Stop stirring, let the reactor cool to room temperature naturally, filter to remove the catalyst, remove the solvent by rotary evaporation, and separate by column chromatography to obtain 26.25 g of product I (5,8-naphthoquinone-1,4-dicarboxylic acid dimethyl ester). Figure 1 shows the nuclear magnetic resonance spectrum of product I. The nuclear magnetic hydrogen spectrum is ¹ H NMR (400MHz, CDCl ₃ )δ7.64(s,1H),6.93(s,1H),3.92(s,3H). The calculated yield is 95.1%.

In a 100 mL autoclave with a polytetrafluoroethylene liner, 1.37 g of product I, 18.8 g of methanol reaction solvent and 0.05 g of 5% Ru/Snβ catalyst (the molar ratio of Ru to product I is 1/200) were added in sequence, stirred and mixed uniformly at room temperature, and then replaced with hydrogen 5 times, filled with 50 bar of hydrogen, heated to 220°C by electric heating, and reacted for 12 hours under magnetic stirring at 1000 rpm. Stop stirring, let the reactor cool to room temperature naturally, filter to remove the catalyst, remove the solvent by rotary evaporation, and dry to obtain a crude product. After column chromatography separation and purification, 1.10 g of product II (dimethyl 1,4-naphthalenedicarboxylate) is obtained. FIG2 is the nuclear magnetic resonance spectrum of product II. The nuclear magnetic hydrogen spectrum is ¹ H NMR (400 MHz, CDCl ₃ ) δ8.82 (dd, J＝6.7,3.4 Hz, 1H), 8.09 (s, 1H), 7.65 (dd, J＝6.7,3.4 Hz, 1H), 4.03 (s, 3H). The calculated yield is 90.1%.

In a 100 mL autoclave with a polytetrafluoroethylene liner, 1.37 g of product I, 18.8 g of methanol reaction solvent and 0.05 g of 5% Ru/Snβ catalyst (the molar ratio of Ru to product I is 1/200) were added in sequence, stirred and mixed uniformly at room temperature, and then replaced with hydrogen 5 times, filled with 50 bar of hydrogen, heated to 220°C by electric heating, and reacted for 12 hours under magnetic stirring at 1000 rpm. After cooling to room temperature, the reactor was opened, 20 mL of 1 mol L ^-1 sodium hydroxide solution was added, the reactor was sealed, and the temperature was raised to 120 ° C by electric heating under nitrogen atmosphere. The reaction was carried out for 10 hours under magnetic stirring at 1000 rpm, and the stirring was stopped. The reactor was naturally cooled to room temperature, the catalyst was filtered out, the reaction solution was neutralized with dilute acid to pH = 1, and then the solution was extracted with ethyl acetate for 3 times. The organic phase was dried with anhydrous sodium sulfate overnight, and the solvent was removed by rotary evaporation to obtain a crude product. After purification by column chromatography, 0.95 g of product III (1,4-naphthalenedicarboxylic acid) was obtained. FIG3 is the nuclear magnetic resonance spectrum of product III. The nuclear magnetic hydrogen spectrum is ¹ H NMR (400 MHz, d ₆ -DMSO) δ13.51 (s, 2H, -COOH), 8.81 (dd, 2H), 8.12 (s, 2H), 7.72 (dd, 2H). The calculated yield is 87.9%.

Example 2 Synthesis and purification of 5,8-dihydroxy-1,4-naphthalenedicarboxylic acid

In a 100 mL autoclave with a polytetrafluoroethylene liner, 1.37 g of product I, 18.8 g of methanol reaction solvent and 0.05 g of 5% Ru/Snβ catalyst (the molar ratio of Ru to product I is 1/200) were added in sequence, stirred and mixed uniformly at room temperature, and then replaced with hydrogen 5 times, filled with 5 bar of hydrogen, heated to 80°C by electric heating, and reacted for 8 hours under magnetic stirring at 1000 rpm. Stop stirring, and the reactor can naturally cool to room temperature. Filter to remove the catalyst, remove the solvent by rotary evaporation, and dry to obtain a crude product. After column chromatography separation and purification, 1.32g of product IV (5,8-dihydroxy-1,4-naphthalenedicarboxylic acid dimethyl ester) is obtained. Figure 4 is the nuclear magnetic resonance spectrum of product IV. The nuclear magnetic hydrogen spectrum is ¹ H NMR (400 MHz, d ₆ -DMSO) δ9.82 (s, 1H), 7.36 (s, 1H), 6.80 (s, 1H), 3.82 (s, 3H). ¹³ C NMR (101MHz, d ₆ -DMSO) δ170.97 (s), 145.34 (s), 131.59 (s), 123.35 (s), 121.67 (s), 111.12 (s), 52.52 (s). The calculated yield is 95.6%.

In a 100 mL autoclave with a polytetrafluoroethylene liner, 1.37 g of the product I obtained in Example 1, 18.8 g of methanol reaction solvent and 0.05 g of 5% Ru/Snβ catalyst (the molar ratio of Ru to product I is 1/200) were added in sequence, and after stirring and mixing at room temperature, the hydrogen was replaced 5 times, 5 bar of hydrogen was filled, the temperature was raised to 80°C by electric heating, and the reaction was carried out for 8 hours under magnetic stirring at 1000 rpm. After cooling to room temperature, the reactor was opened, 20 mL of 1 mol L ^-1 sodium hydroxide solution was added, the reactor was sealed, and the temperature was raised to 120° C. by electric heating under nitrogen atmosphere. The reaction was carried out for 10 hours under magnetic stirring at 1000 rpm, and the stirring was stopped. The reactor was naturally cooled to room temperature, the catalyst was filtered out, the reaction solution was neutralized with dilute acid to pH=1, and then the solution was extracted with ethyl acetate for 3 times. The organic phase was dried with anhydrous sodium sulfate overnight, and the solvent was removed by rotary evaporation to obtain a crude product. After purification by column chromatography, 1.17 g of product V (5,8-dihydroxy-1,4-naphthalenedicarboxylic acid) was obtained. The calculated yield was 94.3%.

The above are only a few embodiments of the present application and do not constitute any form of limitation to the present application. Although the present application is disclosed as above with preferred embodiments, it is not intended to limit the present application. Any technician familiar with the profession, without departing from the scope of the technical solution of the present application, using the technical contents disclosed above to make slight changes or modifications are equivalent to equivalent implementation cases and fall within the scope of the technical solution.

Claims (31)

1. A method for preparing a compound having a structure shown in Formula I, characterized in that: Formula I; wherein X or Y is independently selected from one of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl; R is a hydrogen atom or a hydroxyl group; The preparation method comprises at least the following steps: (1) mixing a raw material containing a compound having a structure represented by formula II and p-benzoquinone with a catalyst I and a solvent, and performing a reaction I to obtain a mixture I; (2) mixing the mixture I obtained in (1) with the catalyst II, and reacting II to obtain a compound having a structure shown in formula I; Formula II; The reaction I is a tandem reaction of a Diels-Alder cycloaddition reaction and a dehydrogenation reaction; The reaction II is a hydrodeoxygenation reaction or a hydrogenation reaction; In (2), when reaction II is a hydrogenation reaction, the reaction conditions are A, and the compound having the structure shown in formula I is obtained, wherein R is a hydroxyl group; The condition A includes: The atmosphere of the reaction II is a hydrogen atmosphere; The pressure of reaction II is 1 to 25 bar; The temperature of the reaction II is 25-120°C; The time of the reaction II is 0.5 to 24 hours; (2), when reaction II is a hydrodeoxygenation reaction, the reaction conditions are B; the obtained compound having the structure shown in formula I, in which R is a hydrogen atom; The condition B includes: The atmosphere of the reaction II is a hydrogen atmosphere; The pressure of the reaction II is 30-150 bar; The temperature of the reaction II is 200-300°C; The time of the reaction II is 0.5 to 30 hours; The catalyst I is Snβ; The catalyst II is Ru/Snβ. 2. The preparation method according to claim 1, characterized in that (1), the solvent is selected from an alcohol solvent or an ester solvent; The molar ratio of the compound having the structure shown in Formula II to p-benzoquinone is 1/20 to 10/1; The mass ratio of the compound having the structure shown in Formula II to the solvent is 1/100 to 50/100; The mass ratio of the catalyst I to the compound having the structure shown in formula II is 1/100 to 100/100. 3. The preparation method according to claim 2, characterized in that: The alcohol solvent is selected from at least one of methanol, ethanol, propanol, n-butanol and isopropanol. 4. The preparation method according to claim 2, characterized in that: The ester solvent is selected from at least one of methyl acetate, ethyl acetate, propyl acetate, butyl acetate and isopropyl acetate. 5. The preparation method according to claim 1, characterized in that: The molar ratio of the compound of the structure described in formula II to p-benzoquinone is 1/10 to 2/1. 6. The preparation method according to claim 1, characterized in that: The molar ratio of the compound of the structure described in formula II to p-benzoquinone is 1/5 to 1/1. 7. The preparation method according to claim 1, characterized in that: The mass ratio of the compound having the structure shown in Formula II to the solvent is 5/100 to 40/100. 8. The preparation method according to claim 1, characterized in that: The mass ratio of the compound having the structure shown in Formula II to the solvent is 10/100 to 30/100. 9. The preparation method according to claim 1, characterized in that: The mass ratio of the catalyst I to the compound having the structure shown in formula II is 5/100 to 60/100. 10. The preparation method according to claim 1, characterized in that: The mass ratio of the catalyst I to the compound having the structure shown in formula II is 8/100 to 20/100. 11. The preparation method according to claim 1, characterized in that: In (1), the temperature of the reaction I is 50-300° C.; and the time of the reaction I is 0.5-24 hours. 12. The preparation method according to claim 1, characterized in that: The temperature of the reaction I is 100-220°C. 13. The preparation method according to claim 1, characterized in that: The temperature of the reaction I is 120-160°C. 14. The preparation method according to claim 1, characterized in that: The reaction time is 1 to 16 hours. 15. The preparation method according to claim 1, characterized in that: The reaction time is 2 to 10 hours. 16. The preparation method according to claim 1, characterized in that: In (2), the molar ratio of the metal active component in the catalyst II to the compound having the structure shown in formula II is 1/2000 to 1/50. 17. The preparation method according to claim 1, characterized in that: The molar ratio of the metal active component in the catalyst II to the compound having the structure shown in formula II is 1/1000 to 1/100. 18. The preparation method according to claim 1, characterized in that: The molar ratio of the metal active component in the catalyst II to the compound having the structure shown in formula II is 1/500 to 1/200. 19. The preparation method according to claim 1, characterized in that: The condition A includes: the pressure of the reaction II is 2-10 bar. 20. The preparation method according to claim 1, characterized in that: The condition A includes: the temperature of the reaction II is 25-100°C. 21. The preparation method according to claim 1, characterized in that: The condition A includes: the temperature of the reaction II is 25-60°C. 22. The preparation method according to claim 1, characterized in that: The condition A includes: the reaction time of the reaction II is 1 to 16 hours. 23. The preparation method according to claim 1, characterized in that: The condition A includes: the reaction time of the reaction II is 5 to 10 hours. 24. The preparation method according to claim 1, characterized in that: The condition B includes: the pressure of the reaction II is 30~100 bar. 25. The preparation method according to claim 1, characterized in that: The condition B includes: the pressure of the reaction II is 30~60bar. 26. The preparation method according to claim 1, characterized in that: The condition B includes: the temperature of the reaction II is 200-280°C. 27. The preparation method according to claim 1, characterized in that: The condition B includes: the temperature of the reaction II is 200-240°C. 28. The preparation method according to claim 1, characterized in that: The condition B includes: the reaction II lasts for 1 to 24 hours. 29. The preparation method according to claim 1, characterized in that: The condition B includes: the reaction time of the reaction II is 5 to 12 hours. 30. A method for preparing a compound having a structure represented by formula III, characterized in that: One of the compounds having a structure shown in Formula I is obtained by the preparation method according to any one of claims 1 to 29, and hydrolyzed to obtain a compound having a structure shown in Formula III; Formula III; Here, R is a hydrogen atom or a hydroxyl group. 31. The preparation method according to claim 30, characterized in that: The hydrolysis process comprises mixing a compound having a structure shown in Formula I with an alkaline solution; The alkali in the alkaline solution is selected from at least one of sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate or potassium bicarbonate; The molar ratio of the base in the alkaline solution to the compound having the structure shown in Formula I is 6:1 to 1:1; The hydrolysis temperature is 50-200°C; The hydrolysis time is 1 to 20 hours.