CN107539955B - Solvent system for producing hydrogen peroxide by anthraquinone process, bidirectional working solution and application - Google Patents
Solvent system for producing hydrogen peroxide by anthraquinone process, bidirectional working solution and application Download PDFInfo
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Abstract
The solvent system for producing hydrogen peroxide by an anthraquinone process comprises 50-70% of tetrahydronaphthalene and 30-50% of ketones by volume, wherein the ketones have a structure shown in a general formula I, and R is1Is phenyl, R2Is selected from phenyl or C1-4 alkyl. The bidirectional working solution comprises alkylanthraquinone and the solvent system, and the weight content of the alkylanthraquinone in the working solution is 80-500 g/L. The bidirectional working solution can be applied to hydrogen peroxide production by an anthraquinone process, on one hand, the ketones participate in the reaction to generate hydrogen peroxide, and on the other hand, the changes before and after the ketones participate in the reaction can respectively improve the solubility of reactants and products in a solvent, thereby greatly improving the hydrogen efficiency. By adopting the working solution system, the hydrogen efficiency can reach 12-16 g/L, which is improved by more than 30% compared with the prior art.
Description
Technical Field
The invention relates to a solvent and working solution for producing hydrogen peroxide by an anthraquinone process, and particularly relates to a bidirectional working solution system for producing hydrogen peroxide by the anthraquinone process.
Background
Hydrogen peroxide (H)2O2) The polymer is widely applied to industries such as papermaking, chemical synthesis, military industry, medicine, cosmetics, environmental protection and the like as an oxidant, a bleaching agent, a disinfectant, a polymer initiator and a cross-linking agent, and is an environment-friendly chemical product because the polymer does not generate byproducts polluting the environment in the production and use processes and only releases oxygen and water, so the polymer is called a green chemical product. With the improvement of living standard and the enhancement of environmental awareness, the substitution of chlorine by hydrogen peroxide is further promotedThe use of hydrogen peroxide opens up a wider market.
The current technological technology for producing hydrogen peroxide mainly comprises the following steps: inorganic reaction, electrolysis, isopropanol, hydrogen-oxygen direct synthesis and anthraquinone. The inorganic chemical reaction method is to prepare hydrogen peroxide by reacting sulfuric acid or phosphoric acid with barium oxide and to produce a by-product of barium sulfate which is insoluble in water. The method cannot realize large-scale industrial production, mainly because the by-product barium sulfate cannot be recycled, the barium oxide is used in too large amount and seriously polluted, and therefore, the method is eliminated. In 1853, Medinger discovered that hydrogen peroxide is generated in the process of electrolyzing sulfuric acid, and through the development of decades, the electrolytic method for producing hydrogen peroxide once became the main method for producing hydrogen peroxide. Also, Apietsch and g.adolph successfully established a persulfate electrolysis process in 1910, including the persulfate process, the potassium persulfate process, and the ammonium persulfate process. The persulfate process mainly comprises the following steps: the potassium hydrogen sulfate or the ammonium hydrogen sulfate is firstly electrolyzed into corresponding persulfate, and then the persulfate is hydrolyzed to generate hydrogen peroxide, wherein the hydrolysis of the potassium persulfate needs to adopt the participation of ammonium persulfate. Then the generated hydrogen peroxide is distilled and purified to obtain 30 to 35 percent hydrogen peroxide aqueous solution. The method integrates three methods, namely an ammonium persulfate method which is mainly adopted in industry, and has the advantages of high current utilization efficiency, short process flow and low power consumption. While the persulfuric acid method has simple device and operation, the current utilization efficiency in the electrolysis process is low; although the potassium persulfate method can obtain purer products and correspondingly improves the current utilization efficiency, the method has complex operation, needs intermittent operation in the local production process, does not meet the requirement of high efficiency in industrialization, and is basically eliminated by the market at present. The isopropanol method is developed by the American shell company, can be carried out in a liquid phase or a gas phase, and can produce acetone as a byproduct, but the hydrogen peroxide purification process in the method is complex, the production cost is high, the market competitiveness is lacked, and the technology is basically not adopted at present. The direct hydrogen-oxygen synthesis method is an ideal atom economy reaction for directly catalyzing and synthesizing hydrogen peroxide by hydrogen and oxygen, but the method faces serious technical challenges in industrial application, for example, 1) the explosion range of the mixture of hydrogen and oxygen is wider (4% -94%), and the danger coefficient is larger; 2) the solubility of hydrogen and oxygen in the reaction medium is low, and the production capacity of the hydrogen peroxide is low finally, so that the industrial production requirement cannot be met; 3) the selectivity of hydrogen peroxide generation is affected by direct water-generating reactions, hydrogen peroxide hydrogenation and hydrogen peroxide decomposition reactions, and the selectivity of hydrogen peroxide generation is reduced in the whole reaction path, so that the technology is still in the development stage at present and has a long time for industrial application.
The anthraquinone method is to dissolve alkylanthraquinones (mainly 2-ethylanthraquinone, 2-tert-butylanthraquinone and 2-amylanthraquinone) in a proper mixed solvent to prepare a working solution. In the presence of catalyst (palladium or nickel as active component), the hydrogenation reaction is carried out, the alkyl anthraquinone generates alkyl hydrogen anthraquinone (formula shown in the following formula), and when the hydrogenation reaction is carried out to a certain extent, the tetrahydro alkyl hydrogen anthraquinone is partially generated. The hydroanthraquinone reacts with air to convert the hydroanthraquinone into alkylanthraquinone and simultaneously generate hydrogen peroxide. And (4) feeding the oxidized working solution into an extraction tower, extracting with deionized water, and purifying and concentrating the obtained hydrogen peroxide aqueous solution to obtain a hydrogen peroxide product. The process is the main method for producing hydrogen peroxide at present and is the most mature method. Large-scale manufacturers at home and abroad almost adopt the method to produce the hydrogen peroxide.
In view of the reaction principle of the anthraquinone process for producing hydrogen peroxide, anthraquinone only functions as a hydrogen carrier, and is called a working carrier or a working substance, and a solution of anthraquinone in an organic solvent is called a working solution. In this process, the key indicator for the production efficiency is hydrogen efficiency (in gH)2O2L working solution), the influence on the hydrogen efficiency is mainly determined by the content of a working carrier (alkyl anthraquinone) in the working solution except the catalyst and the process conditions, namely the amount of the selected solvent capable of dissolving the working substance, and a good solvent system can greatly improve the solubility of the working substance, thereby improving the production energy of hydrogen peroxideHowever, since anthraquinone and hydroanthraquinone have a significant difference in properties and it is difficult to make both the solubility of anthraquinone and hydroanthraquinone high by using a single solvent, a mixed solvent composed of two solvents, one of which is mainly used as a solvent for anthraquinone and the other of which is mainly used as a solvent for hydroanthraquinone, is generally used in actual production. In the current industrial production, the anthraquinone solvent is mostly selected from C9-C11 high boiling point mixed aromatic hydrocarbon from petroleum industry, and the hydroanthraquinone solvent is mostly selected from alcohols and esters, such as trioctyl phosphate (TOP), diisobutyl carbinol (DIBC), methylcyclohexyl acetate (MCA) or Hydrogenated Terpineol (HT).
CN104555933A discloses a working solution for producing hydrogen peroxide by an anthraquinone process. The working solution comprises a solvent and a working solution carrier, wherein the solvent comprises the following components in percentage by volume: 50-80% of No. 200 solvent oil, preferably 70-75%, and 20-50% of trioctyl phosphate, preferably 25-30%; the carrier of the working liquid is alkyl anthraquinone. The working solution adopts a two-component solvent system, improves the solubility of anthraquinone, improves the hydrogenation efficiency, simplifies the composition and reduces the production cost compared with a three-component system. CN1552618A discloses an organic solvent system for producing hydrogen peroxide by an anthraquinone process, wherein C9-C10 aromatic hydrocarbon, trioctyl phosphate and 2-methyl cyclohexyl acetate are selected as solvents, so that the solubility and hydrogen efficiency of anthraquinone are improved to a certain extent. CN101798065A discloses a working solution for producing hydrogen peroxide by an anthraquinone process, wherein the solvent composition is as follows: 65-80% of heavy aromatic hydrocarbon, 5-25% of trioctyl phosphate, 4.5-17.8% of N-phenyl N-ethyl benzamide, and the solubility of the working carrier, so that the hydrogenation efficiency is improved. CN103588177A discloses hydrogen peroxide working solution and application thereof in hydrogen peroxide preparation, wherein the working solution comprises 2-ethyl anthraquinone and an organic solvent, the mass concentration of the 2-ethyl anthraquinone is 120-200 g/L, and the solvent comprises the following components in percentage by weight: 70-80% of C9-C10 aromatic hydrocarbon, 14-20% of trioctyl phosphate, 4-10% of 2-methylcyclohexyl acetate and 0.4-0.9% of tertiary amine. The solvent system can improve the solubility of the 2-ethyl anthraquinone and improve the hydrogen efficiency. Chen Sihai et al (Chen Sihai, Chua Shi Wei et al, "research on replacement of trioctyl phosphate by tetrabutyl clothes for hydrogen peroxide production", inorganic salt technology, 2003,3: 21-25) disclose that trioctyl phosphate is replaced by tetrabutyl urea to prepare working solutions with different proportions, and by comparing their physical properties, surface tension, brix, density, etc., hydrogen anthraquinone dissolving capacity, distribution coefficient, influence on hydrogenation reaction speed, etc., it is considered that the replacement of trioctyl phosphate by tetrabutyl urea for hydrogen peroxide production by anthraquinone method is feasible, and it has strong hydrogen anthraquinone dissolving capacity, which is beneficial to hydrogenation reaction, and can increase hydrogen peroxide concentration, reduce production cost, and optimize process operation.
Although the existing technology for producing hydrogen peroxide by an anthraquinone method is improved in the aspect of improving the hydrogen efficiency of the working solution, certain effect is achieved, but the problems that the solvent composition is fixed and the change requirements of the properties of the working solution before and after the reaction cannot be met in the reaction process, so that the content of reaction substances in the working solution before the reaction is low, or the reaction products cannot be effectively dissolved and separated out after the reaction, the abnormal shutdown of the device, even the inactivation of the catalyst and the like occur.
Disclosure of Invention
In order to solve the problem that the solvent system for producing hydrogen peroxide by an anthraquinone process in the prior art has low dissolution rate of reactants or products so as to limit the reaction, the invention provides the solvent system for producing hydrogen peroxide by the anthraquinone process and a bidirectional working solution.
The technical purpose of the first aspect of the invention is to provide a solvent system for producing hydrogen peroxide by an anthraquinone process, which comprises the following components in percentage by volume:
50% -70% of tetrahydronaphthalene
Ketones 30-50%
Wherein the ketones have the general formula I:
Ⅰ
wherein R is1Is phenyl, R2Is selected from phenyl or C1-4 alkyl.
The technical purpose of the second aspect of the invention is to provide a bidirectional working solution for producing hydrogen peroxide by an anthraquinone process, which comprises alkyl anthraquinone and the above solvent system.
The technical purpose of the third aspect of the invention is to provide the application of the bidirectional working solution in the production of hydrogen peroxide by an anthraquinone process.
In the technology for producing hydrogen peroxide by an anthraquinone method, working liquid used in the prior art is generally alkyl anthraquinone and organic solvent, wherein the majority of the organic solvent is heavy aromatic hydrocarbon and trioctyl phosphate, the heavy aromatic hydrocarbon is mainly used for dissolving the alkyl anthraquinone, the alkyl anthraquinone is converted into alkyl hydrogen anthraquinone after hydrogenation reaction, the solubility of the alkyl hydrogen anthraquinone in the heavy aromatic hydrocarbon is very low, and in order to improve the capability of the solvent for dissolving the alkyl hydrogen anthraquinone, a second organic solvent of trioctyl phosphate is also required to be added, so that the capability of the working liquid for dissolving the alkyl anthraquinone and the alkyl hydrogen anthraquinone is reduced. The working solution contains ketones, the solubility of the alkylanthraquinone in the working solution is greatly improved under the combined action of the ketones and the tetrahydronaphthalene before hydrogenation reaction, the alkylanthraquinone is converted into the alkylhydroanthraquinone in the hydrogenation reaction process, meanwhile, the ketones are also subjected to hydrogenation reaction and are converted into corresponding alcohols, and the generated alcohols can greatly improve the solubility of the alkylhydroanthraquinone, so that the solvent composition can be changed along with the change of the reaction environment in the reaction process, and the solubility of reactants and products is greatly improved in different stages; meanwhile, in the process of oxidizing the hydrogenated liquid, the alkyl anthraquinone is oxidized into the alkyl anthraquinone and simultaneously generates hydrogen peroxide, and the alcohols in the hydrogenated liquid are oxidized into the ketones and simultaneously also generate the hydrogen peroxide, so that the hydrogen efficiency in the hydrogen peroxide production is greatly improved. By adopting the working solution system, the hydrogen efficiency can reach 12-16 g/L, which is improved by more than 30% compared with the prior art.
Detailed Description
The following describes the embodiments of the present invention in detail with reference to the technical solutions. It should be understood that the detailed description and specific examples, while indicating the present invention, are given by way of illustration and explanation only, not limitation.
The solvent system for producing hydrogen peroxide by the anthraquinone process comprises the following components in percentage by volume:
50% -70% of tetrahydronaphthalene
Ketones 30-50%
Wherein the ketones have the general formula I:
Ⅰ
wherein R is1Is phenyl, R2Is selected from phenyl or C1-4 alkyl.
In the above solvent system, as a preferred embodiment, the components and composition thereof are as follows:
55-65% of tetrahydronaphthalene
35% -45% of ketones.
In the above solvent system, as one of preferable embodiments, the R2The ketone is selected from phenyl or linear alkyl of C1-4, and as a more preferable embodiment, the ketone is benzophenone or butanone.
The invention also provides a bidirectional working solution for producing hydrogen peroxide by an anthraquinone process, which comprises alkyl anthraquinone and the solvent system.
In the bidirectional working solution, the weight content of the alkylanthraquinone in the working solution is 80 g/L-500 g/L, preferably 120 g/L-300 g/L.
In the above-mentioned bidirectional working fluid, the alkylanthraquinone is a compound having one or more alkyl substituents on the anthraquinone mother nucleus, preferably a compound having one alkyl substituent at the 2-position of the anthraquinone mother nucleus, and as a more specific embodiment, the alkylanthraquinone is at least one selected from the group consisting of 2-ethylanthraquinone, 2-propylanthraquinone, 2-butylanthraquinone and 2-amylanthraquinone.
The invention also provides application of the bidirectional working solution in production of hydrogen peroxide by an anthraquinone process.
When the bidirectional working solution is used for producing hydrogen peroxide, the working solution is suitable for hydrogenation conditions as follows: the temperature is 40-80 ℃, the hydrogen partial pressure is 0.05-1.0 MPa, and the volume airspeed is 1.0h-1~100h-1The volume ratio of hydrogen to oil is 1-100; the working solution is applicable to the oxidation conditions as follows: the temperature is 30-60 ℃, the oxygen partial pressure is 0.01-0.2 MPa, and the time is 0.01-0.5 h.
The following non-limiting examples are presented to enable those of ordinary skill in the art to more fully understand the present invention and are not intended to limit the invention in any way.
In the examples of the present invention, the performance evaluation conditions of the working fluid were as follows: the evaluation is carried out on a miniature continuous fixed bed reactor, the catalyst adopts the prior industrial catalyst FHPO-2, the loading amount of the catalyst is 10 ml, and the hydrogenation conditions are as follows: the temperature is 60 ℃, the hydrogen partial pressure is 0.3MPa, and the volume space velocity is 20h-1And the volume ratio of the hydrogen to the oil is 15, taking the hydrogenated liquid which reacts for 24-36 hours, and oxidizing under the oxidation conditions that: the temperature is 550 ℃, the oxygen partial pressure is 0.04MPa (the volume ratio of oxygen to nitrogen is 1: 5), the time is 0.3h, the obtained oxidation solution is extracted for three times by distilled water with the same volume, the combined extract is titrated by potassium permanganate solution, and the hydrogen efficiency is calculated.
Example 1
Weighing 60 percent of tetrahydronaphthalene and 40 percent of butanone (20 ℃) according to volume percentage content, fully mixing at room temperature, then taking 10 liters of the mixed solvent, adding 2-ethylanthraquinone until the mixed solvent reaches a saturated state, calculating the mass content of the 2-ethylanthraquinone in the working solution to be 137g/L, adding 10 percent of the mixed solvent into the saturated working solution in order to prevent working substances from being precipitated due to temperature fluctuation during evaluation, evaluating the reaction performance of the working solution under the experimental conditions, and calculating the hydrogen efficiency to be 13.5gH through hydrogenation, oxidation and extraction processes2O2and/L working solution.
Examples 2 to 15
The preparation process and experimental method are the same as example 1, the solvent composition is different from example 1, and the mass content and hydrogen efficiency of the working substance (i.e. alkyl anthraquinone) in the obtained working solution are shown in table 1 and table 3.
Comparative examples 1 to 3
The preparation process and experimental method are the same as example 1, the solvent composition is different from example 1, and the mass content and hydrogen efficiency of the working substance (i.e. alkyl anthraquinone) in the obtained working solution are shown in table 2 and table 3.
TABLE 1 composition of solvent in examples
The ketones include acetophenone in example 3, propiophenone in example 6, cyclopentanone in example 8, hexanophenone in example 10, benzophenone in examples 11 to 15, and butanone in the rest.
TABLE 2 composition of solvents in comparative examples 1 to 3
TABLE 3 reaction Performance of working solutions of examples and comparative examples
The working substance in the composition is 2-propyl anthraquinone in example 3, 2-tert-butyl anthraquinone in example 5, 2-tert-amyl hexananthraquinone in example 7 and 2-ethyl anthraquinone in the rest.
The results in Table 3 show that, compared with the comparative example, the anthraquinone dissolving capacity of the working solution system is improved by more than 6.2 percent, and the hydrogen efficiency is improved by more than 33.3 percent, thereby showing the excellent performance of the working solution system.
Claims (8)
1. The solvent system for producing hydrogen peroxide by the anthraquinone method comprises the following components in percentage by volume:
50% -70% of tetrahydronaphthalene
Ketones 30-50%
Wherein the ketone is selected from one of benzophenone, butanone, propiophenone, hexanophenone, acetophenone or pentanone.
2. The solvent system of claim 1, wherein the components and composition are as follows:
55-65% of tetrahydronaphthalene
35% -45% of ketones.
3. The bidirectional working liquid for producing hydrogen peroxide by the anthraquinone process comprises alkyl anthraquinone and the solvent system of claim 1 or 2.
4. The two-way working fluid of claim 3, wherein the weight content of the alkylanthraquinone in the working fluid is 80g/L to 500 g/L.
5. The two-way working fluid of claim 3, wherein the weight content of the alkylanthraquinone in the working fluid is 120g/L to 300 g/L.
6. The bi-directional working fluid of claim 3, wherein said alkylanthraquinone is selected from at least one of 2-ethylanthraquinone, 2-propylanthraquinone, 2-butylanthraquinone and 2-amylanthraquinone.
7. Use of the bidirectional working fluid of any one of claims 3 to 6 in the production of hydrogen peroxide by an anthraquinone process.
8. The use according to claim 7, wherein the working fluid is subjected to hydrogenation conditions selected from the group consisting of: the temperature is 40-80 ℃, the hydrogen partial pressure is 0.05-1.0 MPa, and the volume airspeed is 1.0h-1~100h-1The volume ratio of hydrogen to oil is 1-100; the working solution is applicable to the oxidation conditions as follows: the temperature is 30-60 ℃, the oxygen partial pressure is 0.01-0.2 MPa, and the time is 0.01-0.5 h.
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| US3150930A (en) * | 1961-04-03 | 1964-09-29 | Edogawa Kagaku Kogyo Kabushiki | Process for the dehydrogenation of a tetrahydroanthraquinone to an anthraquinone |
| DE19816297A1 (en) * | 1998-04-11 | 1999-10-21 | Degussa | Process for the production of hydrogen peroxide and reaction support for its implementation |
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| 蒽醌法制过氧化氢;张东南等;《化学世界》;19621231;402-404页 * |
| 蒽醌法生产双氧水的研究进展;陈冠群等;《化学工业与工程》;20061130;550-556页 * |
| 蒽醌法生产过氧化氢的载体和溶剂组成概述;方静;《化工科技》;19981231;18-23页 * |
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