CN107539955A - Dicyandiamide solution, two-way operation liquid and the application of hydrogen dioxide solution production by anthraquinone process - Google Patents
Dicyandiamide solution, two-way operation liquid and the application of hydrogen dioxide solution production by anthraquinone process Download PDFInfo
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Abstract
Dicyandiamide solution, two-way operation liquid and the application of hydrogen dioxide solution production by anthraquinone process, the dicyandiamide solution include 50% ~ 70% naphthane and 30% ~ 50% ketone by volume, and the ketone has the structure of formula I, wherein, R1For phenyl, R2Alkyl selected from phenyl or C1 ~ 4.The two-way operation liquid includes alkyl-anthraquinone and described dicyandiamide solution, and weight content of the alkyl-anthraquinone in working solution is 80g/L ~ 500g/L.The two-way operation liquid can be applied to hydrogen dioxide solution production by anthraquinone process, on the one hand, participate in reacting by ketone itself and generate hydrogen peroxide, on the other hand, ketone, which participates in the front and rear change of reaction, can be respectively increased the solubility of reactant and product in a solvent, so as to greatly improve hydrogen effect.Using working solution system of the present invention, hydrogen effect can reach 12g/L ~ 16g/L, and more than 30% is improved than prior art.
Description
Technical field
The present invention relates to the solvent of hydrogen dioxide solution production by anthraquinone process and working solution, more specifically, is related to a kind of anthraquinone life
Produce hydrogen peroxide two-way operation liquid system.
Background technology
Hydrogen peroxide (H2O2), industrially there is relatively broad application, be used as a kind of oxidant, bleaching agent, disinfectant, poly-
Compound initiator and crosslinking agent, it is widely used in the row such as papermaking, chemicals synthesis, military project, medicine, cosmetics and environmental protection
Industry, because it does not produce the byproduct of pollution environment in the production and use process, oxygen and water are only discharged, is a kind of environment
Friendly chemical products, so being referred to as green chemical products., will as people's living standard improves the enhancing with environmental consciousness
Replacement of the hydrogen peroxide to chlorine is further promoted, so as to open more extensive market for the application of hydrogen peroxide.
The technology of Hydrogen Peroxide Production mainly has at present:Inorganic reaction method, electrolysis, isopropanol method, hydrogen-oxygen directly close
Into method and anthraquinone.Inorganic polymer composite flocculant method is to prepare hydrogen peroxide with barium monoxide reaction by sulfuric acid or phosphoric acid, and by-product does not dissolve in
The barium sulfate of water.This method can not large-scale industrial production, being primarily due to accessory substance barium sulfate can not recycle, oxidation
Barium usage amount is excessive, seriously polluted, so being eliminated.Medinger in 1853 has found there is dioxygen in sulfuric acid process is electrolysed
The generation of water, by the development of decades afterwards, electrolysis production hydrogen peroxide once once turned into the main side of production hydrogen peroxide
Method.Also, Apietsch and G.Adolph successfully established persulfate electrolysis, including over cure acid system, over cure in 1910
Sour potassium method and ammonium persulfate method.Persulfate method main flow is:Potassium acid sulfate or hydrogen sulfate ammonia are electrolysed to be corresponding first
Persulfate, the hydrogen peroxide of hydrolysis generation afterwards, wherein, the hydrolysis of potassium peroxydisulfate needs the participation using ammonium persulfate.Give birth to afterwards
Into hydrogen peroxide be distilled purification obtain 30%-35% aqueous hydrogen peroxide solution.Comprehensive three kinds of methods, ammonium persulfate method is industrial
The method mainly used, this method current utilization efficiency is high, technological process is short, power consumption is low.Although and over cure acid system device and behaviour
Make simply, but the current utilization efficiency in electrolytic process is relatively low;Potassium peroxydisulfate method, although purer product can be obtained, electricity
Stream utilization ratio is correspondingly improved, but this method complex operation, is needed intermittently operated during localized production, is not met
Efficiently required in industrialization, now substantially by market.Isopropanol method is the exploitation of shell companies of the U.S., and the method can be
Carry out also carrying out in the gas phase in liquid phase, and the method can by-product acetone, but hydrogen peroxide purifying technique is complicated in this method,
Production cost is high, lacks the market competitiveness, is substantially all now and is not using the technology.Hydrogen-oxygen direct synthesis technique be by hydrogen and
Oxygen directly catalyzes and synthesizes hydrogen peroxide, is a kind of preferable atom economic reaction, still, this method is in industrial applications
Face the technological challenge of sternness, such as 1)Hydrogen and oxygen mix explosive range are wider(4%-94%), danger coefficient is larger;2)Hydrogen
The solubility of gas and oxygen in reaction medium is smaller, and the production capacity of final hydrogen peroxide is relatively low, it is impossible to meets industrial production
It is required that;3)In whole response path, generating the selectivity of hydrogen peroxide, water is reacted, hydrogen peroxide is hydrogenated with by directly generating
With hydrogen peroxide decompose etc. reaction influence, so as to reduce generation hydrogen peroxide selectivity, so now the technology also locate
In development, also have for quite a long time away from commercial Application.
Anthraquinone is by alkyl-anthraquinone(Mainly 2- EAQs, 2- tert-butyl groups anthraquinone and 2- amyl anthraquinones)It is dissolved in suitable
When in the mixed solvent, be configured to working solution.In catalyst(Active component is palladium or nickel)In the presence of, hydrogenation is carried out,
Alkyl-anthraquinone generates alkyl hydrogen anthraquinone(Equation sees below formula), when hydrogenation is carried out to a certain extent, part generates tetrahydrochysene alkane
Base hydrogen anthraquinone.By hydrogen anthraquinone and air reaction, hydrogen anthraquinone conversion alkyl-anthraquinone, while generate hydrogen peroxide.Work after oxidation
Liquid enters in extraction tower, is extracted with deionized water, obtained aqueous hydrogen peroxide solution is purified, concentration can obtain peroxide
Change hydrogen production.The technique is to produce the main method of hydrogen peroxide at present, and method the most ripe.Large-scale life both at home and abroad
Producer is produced nearly all using this method production hydrogen peroxide.
In terms of the reaction principle of hydrogen dioxide solution production by anthraquinone process, anthraquinone only plays hydrogen donor, thus be referred to as working material or
Operation material, and it is dissolved in the solution of organic solvent and is referred to as working solution.In the process, the crucial index of production efficiency is investigated
It is hydrogen effect(Unit is gH2O2/ L working solutions), hydrogen effect height is influenceed in addition to catalyst and process conditions, depends mainly on work
Working material in liquid(Alkyl-anthraquinone)Content, that is, selected solvent can dissolve the amount of operation material, good solvent system
The solubility of operation material can be greatly improved, so as to improve the production capacity of hydrogen peroxide, but because anthraquinone and hydrogen anthraquinone exist
There is obvious difference in nature, using single solvent it is difficult to make the solubility of both anthraquinone and hydrogen anthraquinone high, so, in reality
The much more general mixed solvents using two kinds of solvents compositions in the production of border, one mainly as anthraquinone solvent, it is another mainly as
The solvent of hydrogen anthraquinone.At present in industrial production, the solvent as anthraquinone is mostly from the height boiling of the C9-C11 from petroleum industry
Point BTX aromatics, the solvent that quinone is feared as hydrogen then selects alcohols and esters more, such as trioctyl phosphate (TOP), diisobutyl carbinol (DIBC)
(DIBC), methyl cyclohexanol acetate (MCA) or hydrogenation terpene pine camphor (HT) etc..
CN104555933A discloses a kind of working solution of hydrogen dioxide solution production by anthraquinone process.The working solution includes solvent and work
The percent by volume of each component is in liquid carrier, wherein solvent:No. 200 solvent naphthas 50%~80%, preferably 70%~75%, tricresyl phosphate
The ratio of monooctyl ester is 20%~50%, preferably 25%~30%;Working solution carrier is alkyl-anthraquinone.The working solution uses two component solvents
System, anthraquinone solubility is improved, improves hydrogenation efficiency, compared with three compositions system, simplified composition, reduce and be produced into
This.CN1552618A discloses a kind of organic solvent system for hydrogen dioxide solution production by anthraquinone process, wherein the virtue from C9 ~ C10
Hydrocarbon, trioctyl phosphate and 2- methylcyclohexyls acetate are solvent, improve the solubility and hydrogen effect of anthraquinone to a certain extent.
CN101798065A discloses a kind of working solution for hydrogen dioxide solution production by anthraquinone process and allotted, and wherein solvent group turns into:Heavy aromatics
65% ~ 80%, the pungent fat 5% ~ 25% of tricresyl phosphate, N- phenyl N- ethyl benzamides 4.5% ~ 17.8%, the solubility of working material,
Improve hydrogenation efficiency.CN103588177A discloses a kind of hydrogen-peroxide working solution and its application in hydrogen peroxide preparation, institute
The working solution stated includes 2- EAQs and organic solvent, and the mass concentration of described 2- EAQs is 120 ~ 200g/L, is pressed
According to referring to that solvent described in percentage includes following components:C9-C10 aromatic hydrocarbons 70% ~ 80%, the pungent fat 14% ~ 20% of tricresyl phosphate, 2- methyl
Cyclohexyl acetate 4% ~ 10% and tertiary amine 0.4% ~ 0.9%.The dicyandiamide solution can improve the solubility of 2- EAQs, improve
Hydrogen is imitated.Chen Sihai etc.(Chen Sihai, Cai Zhiwei etc., " tetrabutyl clothes replace the pungent cruel research for being used for Hydrogen Peroxide Production of tricresyl phosphate ", nothing
Machine salt technology, 2003,3:21-25)Disclose by tricresyl phosphate it is pungent it is cruel replace with tetrabutyl urea be configured to different proportion work it is molten
Liquid, by the physical property surface tension for comparing them, vigorous degree, density etc., dissolved hydrogen anthraquinone ability, distribution coefficient and to hydrogenation
Influence of speed etc., it is believed that pungent cruel to replace with tetrabutyl urea be feasible, its dissolved hydrogen to hydrogen dioxide solution production by anthraquinone process by tricresyl phosphate
Anthraquinone ability is strong, beneficial to hydrogenation, can improve hydrogen peroxide concentration, reduce production cost, technological operation optimization.
Although existing hydrogen dioxide solution production by anthraquinone process technology has made some improvements in raising work liquid hydrogen efficacious prescriptions face and also achieved
Certain effect, but still solvent composition be present and fix, it is impossible to adapt to operation material during the course of the reaction and react fore/aft properties
Change demand, so reactive material content is low in working solution before causing to react, or after reaction product can not effectively dissolve and
Separate out, occur device improper shut-down even catalyst inactivation the problems such as.
The content of the invention
It is low to reactant or product dissolution rate to solve the dicyandiamide solution of hydrogen dioxide solution production by anthraquinone process in the prior art, so as to
The problem of limited reactions, the present invention provide a kind of dicyandiamide solution and two-way operation liquid of hydrogen dioxide solution production by anthraquinone process, and working solution is not
Itself can only react generation hydrogen peroxide during the course of the reaction, can also dissolve more reactants and production respectively in different phase
Thing, improve the hydrogen effect of working solution.
The technical purpose of first aspect present invention is to provide the dicyandiamide solution of hydrogen dioxide solution production by anthraquinone process, contains by volume basis
Gauge, including group consisting of point:
Naphthane 50% ~ 70%
Ketone 30% ~ 50%
Wherein, the ketone has the structure of formula I:
Ⅰ
Wherein, R1For phenyl, R2Alkyl selected from phenyl or C1 ~ 4.
The technical purpose of second aspect of the present invention is to provide a kind of two-way operation liquid of hydrogen dioxide solution production by anthraquinone process, including alkane
Base anthraquinone and above-described dicyandiamide solution.
The technical purpose of third aspect present invention is to provide the two-way operation liquid answering in hydrogen dioxide solution production by anthraquinone process
With.
In the technique of hydrogen dioxide solution production by anthraquinone process, working solution used is generally alkyl-anthraquinone and organic molten in the prior art
Agent, wherein the organic solvent overwhelming majority are heavy aromatics and the pungent fat of tricresyl phosphate, and heavy aromatics main function therein is for dissolving alkane
Base anthraquinone, alkyl-anthraquinone is converted into alkyl hydrogen anthraquinone after the hydrogenation reaction, and solubility of the alkyl hydrogen anthraquinone in heavy aromatics is very
It is low, in order to improve the ability of solvent dissolving alkyl hydrogen anthraquinone, it is also necessary to second of the pungent fat of organic solvent tricresyl phosphate is added, it is such
As a result it is exactly that working solution dissolving alkyl-anthraquinone and the ability of alkyl hydrogen anthraquinone all reduce.And contain ketone in the working solution of the present invention
Class, before hydrogenation, ketone and naphthane it is common in the presence of, increase substantially the solubility of alkyl-anthraquinone wherein,
In hydrogenation process, alkyl-anthraquinone is converted into alkyl hydrogen anthraquinone, while ketone also occurs hydrogenation reaction and is converted into corresponding alcohol
Class, the alcohol of generation can increase substantially the solubility of alkyl hydrogen anthraquinone, so be achieved that solvent composition during the course of the reaction
Can be changed with the change of reaction environment, so as to realize different phase to reactant and product solubility significantly
Degree improves;Simultaneously during liquid oxidation is hydrogenated, alkyl hydrogen anthraquinone is oxidized to produce hydrogen peroxide, hydrogen while alkyl-anthraquinone
The alcohols changed in liquid is oxidized to also produce hydrogen peroxide while ketone, realizes that what hydrogen in Hydrogen Peroxide Production imitated increases substantially.
Using working solution system of the present invention, hydrogen effect can reach 12g/L ~ 16g/L, and more than 30% is improved than prior art.
Embodiment
Describe the embodiment of the present invention in detail below in conjunction with technical scheme.It is it should be appreciated that described herein
Embodiment be merely to illustrate and explain the present invention, be not intended to limit the invention.
The dicyandiamide solution of hydrogen dioxide solution production by anthraquinone process provided by the invention, based on volumn concentration, including consisting of
Component:
Naphthane 50% ~ 70%
Ketone 30% ~ 50%
Wherein, the ketone has the structure of formula I:
Ⅰ
Wherein, R1For phenyl, R2Alkyl selected from phenyl or C1 ~ 4.
It is as follows as preferred embodiment, its each component and composition in above-mentioned dicyandiamide solution:
Naphthane 55% ~ 65%
Ketone 35% ~ 45%.
In above-mentioned dicyandiamide solution, as one of preferred embodiment, the R2Straight chain alkane selected from phenyl or C1 ~ 4
Base, as preferred embodiment, the ketone is benzophenone or phenyl propyl ketone.
The present invention also provides the two-way operation liquid of hydrogen dioxide solution production by anthraquinone process a kind of, including alkyl-anthraquinone and above-described
Dicyandiamide solution.
In above-mentioned two-way operation liquid, weight content of the alkyl-anthraquinone in working solution is 80g/L ~ 500g/L, is preferably
120g/L~300g/L。
In above-mentioned two-way operation liquid, the alkyl-anthraquinone is to have one or more alkyl substituents on anthraquinone parent nucleus
Compound, preferably there is the compound of an alkyl substituent on anthraquinone parent nucleus 2, it is described as more specifically embodiment
Alkyl-anthraquinone is selected from least one of 2- EAQs, 2- propyl group anthraquinone, 2- butyl anthraquinones and 2- amyl anthraquinones.
Present invention also offers application of the two-way operation liquid in hydrogen dioxide solution production by anthraquinone process.
When producing hydrogen peroxide using the two-way operation liquid of the present invention, the applicable hydrogenation conditions of the working solution are:Temperature
40 DEG C ~ 80 DEG C, hydrogen partial pressure 0.05MPa ~ 1.0MPa, volume space velocity 1.0h-1~100h-1, hydrogen to oil volume ratio 1 ~ 100;The work
Making the applicable oxidizing condition of liquid is:30 DEG C ~ 60 DEG C of temperature, oxygen partial pressure 0.01MPa ~ 0.2MPa, time 0.01h ~ 0.5h.
Following non-limiting examples can make one of ordinary skill in the art be more fully understood the present invention, but not with
Any mode limits the present invention.
In an embodiment of the present invention, the performance evaluation condition of working solution is as follows:On miniature continuous fixed bed reactors
Evaluated, catalyst uses existing industrial catalyst FHPO-2, and the loadings of catalyst are 10 milliliters, and hydrogenation conditions are:Temperature
Spend for 60 DEG C, hydrogen partial pressure 0.3MPa, volume space velocity 20h-1, hydrogen to oil volume ratio 15, negate the hydrogenation answered 24 hours ~ 36 hours
Liquid, aoxidized, oxidizing condition is:550 DEG C of temperature, oxygen partial pressure 0.04MPa(Oxygen and nitrogen volume ratio are 1:5), the time
0.3h, obtained oxidation solution are extracted three times with isometric distilled water, and combining extraction liquid is dripped with liquor potassic permanganate
It is fixed, calculate hydrogen effect.
Embodiment 1
By volumn concentration, 60% naphthane, 40% phenyl propyl ketone are measured(20℃)It is sufficiently mixed, then takes at room temperature
10 liters of mixed solvent is stated, 2- EAQs is charged with until reaching saturation state, calculates 2- EAQs in the working solution
In mass content be 137g/L, evaluation when in order to prevent the fluctuation because of temperature from causing the precipitation of operation material, in saturation work
Make to add 10% above-mentioned mixed solvent in liquid, the reactivity worth of the working solution evaluated under foregoing experiment condition,
Through over hydrogenation, oxidation and extraction process, it is 13.5gH to calculate hydrogen effect2O2/ L working solutions.
Embodiment 2 ~ 15
Process for preparation and experimental method are had any different with embodiment 1, are shown in Table 1, the work of gained with embodiment 1, solvent composition
Operation material in liquid(That is alkyl-anthraquinone)Mass content and hydrogen effect be shown in Table 3.
Comparative example 1 ~ 3
Process for preparation and experimental method are had any different with embodiment 1, are shown in Table 2, the work of gained with embodiment 1, solvent composition
Operation material in liquid(That is alkyl-anthraquinone)Mass content and hydrogen effect be shown in Table 3.
The composition of solvent in 1. each embodiment of table
Ketone therein, it is acetophenone in embodiment 3, is propiophenone in embodiment 6, is benzene pentanone in embodiment 8, embodiment 10
In be benzene hexanone, embodiment 11 ~ 15 is benzophenone, and remaining is phenyl propyl ketone.
The composition of solvent in the comparative example 1 ~ 3 of table 2.
The working solution reactivity worth of 3. each embodiment of table and comparative example
Operation material therein, it is 2- propyl group anthraquinones in embodiment 3, is 2- tert-butyl group anthraquinones in embodiment 5, is in embodiment 7
Penta own anthraquinone of uncle 2-, remaining is 2- EAQs.
The result of table 3 is shown, compared with comparative example, the anthraquinone solvability of working solution system of the present invention improve 6.2% with
On, and hydrogen effect improves more than 33.3%, embodies the excellent performance of working solution system of the present invention.
Claims (9)
1. the dicyandiamide solution of hydrogen dioxide solution production by anthraquinone process, based on volumn concentration, including group consisting of point:
Naphthane 50% ~ 70%
Ketone 30% ~ 50%
Wherein, the ketone has the structure of formula I:
Ⅰ
Wherein, R1For phenyl, R2Alkyl selected from phenyl or C1 ~ 4.
2. dicyandiamide solution according to claim 1, it is characterised in that each component and composition are as follows:
Naphthane 55% ~ 65%
Ketone 35% ~ 45%.
3. dicyandiamide solution according to claim 1, it is characterised in that R2Straight chained alkyl selected from phenyl or C1 ~ 4.
4. dicyandiamide solution according to claim 1, it is characterised in that the ketone is benzophenone or phenyl propyl ketone.
5. the two-way operation liquid of hydrogen dioxide solution production by anthraquinone process, including alkyl-anthraquinone and molten described in claim 1 ~ 4 any one
Agent system.
6. two-way operation liquid according to claim 5, it is characterised in that weight content of the alkyl-anthraquinone in working solution be
80g/L ~ 500g/L, preferably 120g/L ~ 300g/L.
7. two-way operation liquid according to claim 5, it is characterised in that the alkyl-anthraquinone is selected from 2- EAQs, 2-
At least one of propyl group anthraquinone, 2- butyl anthraquinones and 2- amyl anthraquinones.
8. application of the two-way operation liquid in hydrogen dioxide solution production by anthraquinone process described in claim 5 ~ 7 any one.
9. application according to claim 8, it is characterised in that the applicable hydrogenation conditions of the working solution are:40 DEG C of temperature ~
80 DEG C, hydrogen partial pressure 0.05MPa ~ 1.0MPa, volume space velocity 1.0h-1~100h-1, hydrogen to oil volume ratio 1 ~ 100;The working solution is fitted
Oxidizing condition is:30 DEG C ~ 60 DEG C of temperature, oxygen partial pressure 0.01MPa ~ 0.2MPa, time 0.01h ~ 0.5h.
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CN111908429A (en) * | 2020-07-23 | 2020-11-10 | 江苏理文化工有限公司 | Formula of working solution in hydrogen peroxide production process |
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