CN113698332A - Method for preparing hydrogen peroxide cyclopentylbenzene from cyclopentylbenzene - Google Patents

Method for preparing hydrogen peroxide cyclopentylbenzene from cyclopentylbenzene Download PDF

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CN113698332A
CN113698332A CN202010437326.6A CN202010437326A CN113698332A CN 113698332 A CN113698332 A CN 113698332A CN 202010437326 A CN202010437326 A CN 202010437326A CN 113698332 A CN113698332 A CN 113698332A
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China
Prior art keywords
cyclopentylbenzene
hydroperoxide
initiator
peroxide
peroxidation
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CN202010437326.6A
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夏金魁
李安
刘坤
肖哲
邱旭
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China Petroleum and Chemical Corp
Sinopec Baling Co
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China Petroleum and Chemical Corp
Sinopec Baling Co
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C407/00—Preparation of peroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated

Abstract

The invention relates to the field of chemical industry, and discloses a method for preparing hydrogen peroxide cyclopentylbenzene from cyclopentylbenzene. The method comprises the following steps: mixing cyclopentylbenzene and an initiator to obtain a mixture, introducing an oxygen-containing gas into the mixture, and carrying out peroxidation at 50-130 ℃ to obtain cyclopentylbenzene hydroperoxide. The initiator initiated self-catalytic oxidation process of the cyclopentylbenzene can be used for reaction without adding a catalyst, so that the use cost of the catalyst and the subsequent catalyst/reactant separation process are reduced, the cost is reduced, and meanwhile, higher yield and selectivity of the hydrogen peroxide cyclopentylbenzene and the conversion rate of the cyclopentylbenzene can be obtained.

Description

Method for preparing hydrogen peroxide cyclopentylbenzene from cyclopentylbenzene
Technical Field
The invention relates to the field of chemical industry, and particularly relates to a method for preparing hydrogen peroxide cyclopentylbenzene from cyclopentylbenzene.
Background
Phenol is an important compound in chemical industry, and can be used for preparing chemical products and intermediates such as phenolic resin, caprolactam, bisphenol A, salicylic acid, picric acid, pentachlorophenol, 2,4-D, adipic acid, phenolphthalein n-acetoacetoxy aniline and the like, and has important application in the industries such as chemical raw materials, alkylphenol, synthetic fibers, plastics, synthetic rubber, medicines, pesticides, spices, dyes, coatings, oil refining and the like. In addition, phenol can be used as a solvent, an experimental reagent and a disinfectant, and the protein on the chromosome in the plant cell can be separated from the DNA by the aqueous solution of the phenol, so that the DNA can be conveniently dyed. At present, the cumyl benzene method which is a common route for producing phenol is traditionally used, and cyclopentanone is also produced by adipic acid condensation or cyclopentene hydration. The methods can only produce phenol or cyclopentanone singly, and have the problems of low economic benefit of production, serious corrosion of acid used in the production process to equipment and the like. The high-value phenol and cyclopentanone can be simultaneously produced from the cyclopentylbenzene through the processes of peroxidation and acidolysis, the atom utilization rate reaches 100%, and the route has high economic value.
In the process of producing the hydrogen peroxide cyclopentylbenzene by the peroxidation of the cyclopentylbenzene, the addition of a catalyst is often required to improve the selectivity and the conversion rate of the reaction. CN 103261126a reports that cyclohexylbenzene peroxide to the corresponding hydroperoxide, which can then be decomposed to produce phenol and cyclohexanone; NHPI and the like are added in the process as catalysts, so that the yield of the hydrogen peroxide cyclohexylbenzene is improved. However, the catalyst itself is expensive, and the subsequent separation of the catalyst and the reactants increases the energy consumption for separation in the production process and increases the production cost.
Disclosure of Invention
The invention aims to overcome the problems of high cost of a catalyst and subsequent need of separating the catalyst from reactants in the prior art, and provides a method for preparing cyclopentylbenzene hydroperoxide from cyclopentylbenzene.
In order to achieve the above objects, the present invention provides a method for preparing cyclopentylbenzene hydroperoxide from cyclopentylbenzene, the method comprising: mixing cyclopentylbenzene and an initiator to obtain a mixture, introducing an oxygen-containing gas into the mixture, and carrying out peroxidation at 50-130 ℃ to obtain cyclopentylbenzene hydroperoxide.
Preferably, the peroxidation is carried out without the addition of a catalyst.
The invention provides a method for preparing hydrogen peroxide cyclopentylbenzene from cyclopentylbenzene, which can still obtain higher yield and selectivity of the hydrogen peroxide cyclopentylbenzene and higher conversion rate of the cyclopentylbenzene without adding a peroxide catalyst.
The method can be carried out under the condition of no addition of a catalyst by the self-catalytic oxidation process of the cyclopentylbenzene initiated by the initiator, so that the use cost of the catalyst and the subsequent catalyst/reactant separation process are reduced, and the cost is reduced.
Detailed Description
The endpoints of the ranges and any values disclosed herein are not limited to the precise range or value, and such ranges or values should be understood to encompass values close to those ranges or values. For ranges of values, between the endpoints of each of the ranges and the individual points, and between the individual points may be combined with each other to give one or more new ranges of values, and these ranges of values should be considered as specifically disclosed herein.
The inventor of the present invention found that in the preparation of cyclopentylbenzene hydroperoxide by the peroxidation of cyclopentylbenzene, the generation of cyclopentylbenzene hydroperoxide can be induced by adding a small amount of initiator, and the generated cyclopentylbenzene hydroperoxide promotes the peroxidation process of the cyclopentylbenzene. Relatively higher conversions of cyclopentylbenzene and cyclopentylbenzene hydroperoxide yields can be obtained using the process of the present invention as compared to catalysis using a catalyst.
The invention provides a method for preparing hydrogen peroxide cyclopentylbenzene by cyclopentylbenzene, which comprises the following steps: mixing cyclopentylbenzene and an initiator to obtain a mixture, introducing an oxygen-containing gas into the mixture, and carrying out peroxidation at 50-130 ℃ to obtain cyclopentylbenzene hydroperoxide.
In the present invention, the time of the peroxidation can be selected within a wide range, and preferably, the time of the peroxidation is 2 to 24 hours, more preferably 8 to 15 hours. Within the preferred ranges, higher cyclopentylbenzene conversion and cyclopentylbenzene hydroperoxide selectivity and yield can be achieved.
In the present invention, the peroxidation of cyclopentylbenzene can be carried out at 50-130 deg.C, preferably at 80-110 deg.C, such as 80, 85, 90, 95, 100, 105, 110 deg.C, and any range between any two values. Within the preferred ranges, higher cyclopentylbenzene conversion and cyclopentylbenzene hydroperoxide selectivity and yield can be achieved.
In the present invention, the oxygen-containing gas used may be a gas containing oxygen as is conventional in the art, such as air, pure oxygen, or a mixture of oxygen and other gases, and the kind thereof is not particularly limited. Preferably, the concentration of oxygen in the oxygen-containing gas is from 20 to 100% by volume.
In the present invention, the amount of the oxygen-containing gas to be used may be selected from a wide range, and preferably, the volume of the oxygen-containing gas introduced per mole of cyclopentylbenzene is 0.2 to 8L/(min. mol), for example, 0.2, 0.4, 0.6, 0.8, 1,2, 3, 4,5, 6, 7, 8L/(min. mol), and any range consisting of any two values. Within the preferred ranges, higher cyclopentylbenzene conversion and cyclopentylbenzene hydroperoxide selectivity and yield can be achieved.
In the present invention, the initiator may be an initiator conventionally used in the art, and may be, for example, a peroxide initiator or an azo initiator, and preferably, the initiator is a peroxide initiator.
In the present invention, the peroxide initiator may be a peroxide initiator conventionally used in the art, and is preferably at least one selected from the group consisting of a hydroperoxy type initiator, a diacyl peroxide type initiator, a dialkyl peroxide type initiator, a diester peroxide type initiator, and a peroxy organic acid/ketone initiator, and more preferably a hydroperoxy type initiator. Under the preferred conditions, the selectivity of the hydrogen peroxide cyclopentylbenzene can be further improved.
In the present invention, the hydroperoxy initiator is preferably at least one selected from the group consisting of cyclopentylbenzene hydroperoxide, tert-butyl hydroperoxide, cyclopentyl-1-phenyl-1-hydroperoxide, cyclohexyl-1-phenyl-1-hydroperoxide, pinane hydroperoxide, 1,3, 3-tetramethylbutyl hydroperoxide, and cumene hydroperoxide.
In the present invention, it is preferable that the diacyl peroxide initiator is at least one selected from the group consisting of dibenzoyl peroxide, di-4-chlorobenzoyl peroxide, di-2, 4-dichlorobenzoyl peroxide, dibenzoyl peroxide and di-4-chlorobenzoyl peroxide.
In the present invention, preferably, the dialkyl peroxide initiator is selected from the group consisting of 1, 1-bis- (t-butylperoxy) cyclohexane, 1-bis- (t-butylperoxy) -3,3, 5-trimethylcyclohexane, 2-dihydroperoxy propane, 2, 5-dimethyl-2, 5-bis- (benzoylperoxy) hexane, 3,6,6,9, 9-hexamethyl-1, 2,4, 5-tetraoxacyclononane, 1-bis- (t-amylperoxy) cyclohexane, 2-bis- (t-butylperoxy) butane, 1-bis- (t-butylperoxy) cyclohexane, 1-bis- (t-butylperoxy) -3,3, 5-trimethylcyclohexane, 1,3, 5-dimethylcyclohexane, and mixtures thereof, 1, 1-bis- (tert-butylperoxy) cyclohexane, 2-bis- (tert-butylperoxy) propane, 1-bis- (tert-butylperoxy) -3,3, 5-trimethylcyclohexane, 2, 5-dimethyl-2, 5-bis- (tert-butylperoxy) hexane, at least one of 2, 5-dimethyl-2, 5-bis- (3,3, 5-trimethylhexanoylperoxy) hexane, 3,6,6,9, 9-hexamethyl-1, 2,4, 5-tetraoxacyclononane, 3,6, 9-triethyl-3, 6, 9-trimethyl-1, 4, 7-triperoxyloxane, di- (2-tert-butylperoxyisopropyl) benzene and tert-butylcumyl peroxide.
In the present invention, it is preferred that the peroxydiester initiator is selected from the group consisting of t-amyl peroxy-3, 5, 5-trimethylhexanoate, t-butyl peroxyacetate, t-butyl monoperoxymaleate, t-butyl monoperoxyphthalate, t-amyl peroxybenzoate, n-butyl 4, 4-bis- (t-butylperoxy) valerate, t-butyl monoperoxymaleate, t-butyl peroxyacetate, t-butyl peroxybenzoate, t-butyl peroxyisopropylcarbonate, t-butyl peroxy-2-methylbenzoate, ethyl 3, 3-bis- (t-butylperoxy) butyrate, di-t-butyl peroxyazelate, di- (t-butylperoxy) phthalate, ethyl 3, 3-bis- (t-amylperoxy) butyrate, ethyl 3, 3-bis- (t-butylperoxy) butyrate and 1, at least one of 1,3, 3-tetramethyl butyl peroxyneodecanoate.
In the present invention, preferably, the peroxy organic acid/ketone initiator is selected from at least one of peracetic acid, 3-chloroperoxybenzoic acid, disuccinic acid peroxide, diperoxydodecanedioic acid, methyl ethyl ketone peroxide, methyl ethyl (meth) ketone peroxide, methyl isobutyl ketone peroxide, acetylacetone peroxide and cyclohexanone peroxide.
In the present invention, the azo initiator may be an azo initiator conventionally used in the art, and preferably, it is perazodiisobutyronitrile and/or perazodiisoheptonitrile.
In the present invention, most preferably, the initiator is cyclopentylbenzene hydroperoxide. Under the preferred conditions, the selectivity of the hydrogen peroxide cyclopentylbenzene can be further improved.
In the present invention, the amount of the initiator can be selected within a wide range, and preferably is 0.01 to 5% by weight, based on the weight of cyclopentylbenzene, such as 0.01, 0.02, 0.04, 0.06, 0.08, 0.1, 0.15, 0.2, 0.4, 0.6, 0.8, 1,2, 3, 4, 5% by weight and any range between any two values, preferably 0.05 to 2% by weight.
In the present invention, the peroxidation process can be carried out without adding a catalyst, and the existing peroxidation reaction for preparing the hydrogen peroxide from the cyclopentylbenzene usually needs to be carried out in the presence of a catalyst, and the catalyst is more preferably a peroxidation catalyst.
In the present invention, the peroxidation catalyst may be selected from compounds that are imines or contain N-OH; for example, N-hydroxyphthalimide, 4-amino-N-hydroxyphthalimide, 3-amino-N-hydroxyphthalimide, tetrabromo-N-hydroxyphthalimide, tetrachloro-N-hydroxyphthalimide, N-hydroxychlorobridge imide, N-hydroxycedrylimide, N-hydroxytoluene-tri-imide, N-hydroxyphenyl-1, 2, 4-trimethylimide, N '-dihydroxy (pyromellitic-diimide), N' -dihydroxy (benzophenone-3, 3',4,4' -tetracarboxydiimide), N-hydroxymaleimide, pyridine-2, 3-dicarboximide, N-hydroxysuccinimide, etc, N-hydroxy (tartrimide), N-hydroxy-5-norbornene-2, 3-dicarboximide, exo-N-hydroxy-7-oxabicyclo [2.2.1] hept-5-ene-2, 3-dicarboximide, N-hydroxy-cis-cyclohexane-1, 2-dicarboximide, N-hydroxy-cis-4-cyclohexene-1, 2-dicarboximide, the sodium salt of N-hydroxynaphthalene dicarboximide, N-hydroxy-O-benzenedisulfonimide or N, N', N "-trihydroxyisocyanuric acid.
In a preferred embodiment of the present invention, the process for preparing cyclopentylbenzene hydroperoxide from cyclopentylbenzene comprises: mixing cyclopentylbenzene and an initiator to obtain a mixture, introducing oxygen-containing gas into the mixture, and performing peroxidation at 80-110 ℃ for 8-15h to obtain cyclopentylbenzene hydroperoxide. The space velocity of the oxygen-containing gas is 10-50min-1. The initiator is a hydroperoxy initiator, and the dosage of the initiator is 0.05-2% by weight based on the weight of the cyclopentylbenzene. The peroxidation process is carried out without the addition of a catalyst. Under the preferable condition, the conversion rate of the cyclopentylbenzene, the selectivity and the yield of the hydrogen peroxide cyclopentylbenzene can be obviously improved.
The present invention will be described in detail below by way of examples.
The hydrogen peroxide cyclopentylbenzene was measured by gas chromatography.
Example 1
This example illustrates the preparation of cyclopentylbenzene hydroperoxide from cyclopentylbenzene as described herein
Using hydrogen peroxide cyclopentylbenzene as an initiator, and fully and uniformly mixing the hydrogen peroxide cyclopentylbenzene with the cyclopentylbenzene, wherein the initiator is 0.2 percent of the mass of the cyclopentylbenzene; then heating the mixture to 100 ℃ for reaction; simultaneously blowing air into the reaction liquid, wherein the air quantity per minute per mole of the cyclopentylbenzene is 3L/(min. mol), and the reaction lasts for 10 h.
After the reaction is finished, the conversion rate of the cyclopentylbenzene, the selectivity and the yield of the cyclopentylbenzene hydroperoxide are measured and calculated, and the specific results are shown in table 1.
Example 2
This example illustrates the preparation of cyclopentylbenzene hydroperoxide from cyclopentylbenzene as described herein
Cumene hydroperoxide is used as an initiator, and is fully and uniformly mixed with the cyclopentylbenzene, wherein the initiator accounts for 1.0 percent of the mass of the cyclopentylbenzene; then heating the mixture to 110 ℃ for reaction; simultaneously, air is blown into the reaction liquid, the air quantity per minute per mol of the cyclopentyl benzene is 1.5L/(min. mol), and the reaction lasts for 8 h.
After the reaction is finished, the conversion rate of the cyclopentylbenzene, the selectivity and the yield of the cyclopentylbenzene hydroperoxide are measured and calculated, and the specific results are shown in table 1.
Example 3
This example illustrates the preparation of cyclopentylbenzene hydroperoxide from cyclopentylbenzene as described herein
Tert-butyl hydroperoxide is used as an initiator, and is fully and uniformly mixed with the cyclopentylbenzene, wherein the initiator accounts for 0.05 percent of the weight of the cyclopentylbenzene; then it is heated to react at 80 ℃; simultaneously, air was blown into the reaction solution, and the amount of air blown per mole of cyclopentylbenzene per minute was 7.3L/(min. mol), and the reaction was continued for 12 hours.
After the reaction is finished, the conversion rate of the cyclopentylbenzene, the selectivity and the yield of the cyclopentylbenzene hydroperoxide are measured and calculated, and the specific results are shown in table 1.
Example 4
This example illustrates the preparation of cyclopentylbenzene hydroperoxide from cyclopentylbenzene as described herein
Cyclohexyl-1-phenyl-1-hydroperoxide is used as an initiator, and is fully and uniformly mixed with the cyclopentylbenzene, wherein the initiator accounts for 1.5 percent of the weight of the cyclopentylbenzene; then heating the mixture to 90 ℃ for reaction; simultaneously, air was blown into the reaction solution, and the amount of air blown per mole of cyclopentylbenzene per minute was 7.3L/(min. mol), and the reaction was continued for 15 hours.
After the reaction is finished, the conversion rate of the cyclopentylbenzene, the selectivity and the yield of the cyclopentylbenzene hydroperoxide are measured and calculated, and the specific results are shown in table 1.
Example 5
This example illustrates the preparation of cyclopentylbenzene hydroperoxide from cyclopentylbenzene as described herein
The azodiisobutyronitrile is used as an initiator and is fully and uniformly mixed with the cyclopentylbenzene, and the initiator accounts for 0.2 percent of the weight of the cyclopentylbenzene; then heating the mixture to 100 ℃ for reaction; simultaneously blowing air into the reaction solution, and the airspeed of the reaction solution is 35min-1The reaction was continued for 11 h.
After the reaction is finished, the conversion rate of the cyclopentylbenzene, the selectivity and the yield of the cyclopentylbenzene hydroperoxide are measured and calculated, and the specific results are shown in table 1.
Example 6
This example illustrates the preparation of cyclopentylbenzene hydroperoxide from cyclopentylbenzene as described herein
The procedure was as in example 1, except that N-hydroxyphthalimide was used as a peroxide catalyst in admixture with cyclopentylbenzene and cyclopentylbenzene hydroperoxide, wherein the amount of N-hydroxyphthalimide was 0.2% by mass of cyclopentylbenzene.
After the reaction is finished, the conversion rate of the cyclopentylbenzene, the selectivity and the yield of the cyclopentylbenzene hydroperoxide are measured and calculated, and the specific results are shown in table 1.
Example 7
This example illustrates the preparation of cyclopentylbenzene hydroperoxide from cyclopentylbenzene as described herein
The procedure was as described in example 1, except that the reaction temperature was 130 ℃.
After the reaction is finished, the conversion rate of the cyclopentylbenzene, the selectivity and the yield of the cyclopentylbenzene hydroperoxide are measured and calculated, and the specific results are shown in table 1.
Example 8
This example illustrates the preparation of cyclopentylbenzene hydroperoxide from cyclopentylbenzene as described herein
The procedure was followed as described in example 1 except that cyclopentylbenzene hydroperoxide was used in an amount of 0.01% by mass based on the amount of cyclopentylbenzene.
After the reaction is finished, the conversion rate of the cyclopentylbenzene, the selectivity and the yield of the cyclopentylbenzene hydroperoxide are measured and calculated, and the specific results are shown in table 1.
Example 9
This example illustrates the preparation of cyclopentylbenzene hydroperoxide from cyclopentylbenzene as described herein
The procedure was followed as described in example 1 except that cyclopentylbenzene hydroperoxide was used in an amount of 5% by mass of cyclopentylbenzene.
After the reaction is finished, the conversion rate of the cyclopentylbenzene, the selectivity and the yield of the cyclopentylbenzene hydroperoxide are measured and calculated, and the specific results are shown in table 1.
Example 10
This example illustrates the preparation of cyclopentylbenzene hydroperoxide from cyclopentylbenzene as described herein
The procedure is as described in example 1, except that the reaction time is 24 h.
After the reaction is finished, the conversion rate of the cyclopentylbenzene, the selectivity and the yield of the cyclopentylbenzene hydroperoxide are measured and calculated, and the specific results are shown in table 1.
Comparative example 1
This comparative example illustrates the preparation of a reference cyclopentylbenzene hydroperoxide from a reference cyclopentylbenzene
The procedure was followed as described in example 1, except that, in the reaction system, the same mass of N-hydroxyphthalimide catalyst was used instead of the initiator cyclopentylbenzene hydroperoxide.
After the reaction is finished, the conversion rate of the cyclopentylbenzene, the selectivity and the yield of the cyclopentylbenzene hydroperoxide are measured and calculated, and the specific results are shown in table 1.
TABLE 1
Figure BDA0002502777590000101
The preferred embodiments of the present invention have been described above in detail, but the present invention is not limited thereto. Within the scope of the technical idea of the invention, many simple modifications can be made to the technical solution of the invention, including combinations of various technical features in any other suitable way, and these simple modifications and combinations should also be regarded as the disclosure of the invention, and all fall within the scope of the invention.

Claims (10)

1. A method for preparing hydrogen peroxide cyclopentylbenzene from cyclopentylbenzene is characterized by comprising the following steps: mixing cyclopentylbenzene and an initiator to obtain a mixture, introducing an oxygen-containing gas into the mixture, and carrying out peroxidation at 50-130 ℃ to obtain cyclopentylbenzene hydroperoxide.
2. The process according to claim 1, wherein the time of peroxidation is 2-24h, preferably 8-15 h.
3. A process according to claim 1 or 2, wherein the temperature of the peroxidation is 80-110 ℃.
4. A process according to any one of claims 1 to 3, wherein the concentration of oxygen in the oxygen-containing gas is in the range of from 20 to 100% by volume.
5. The process as claimed in any one of claims 1 to 4, wherein the volume of oxygen-containing gas introduced per mole of cyclopentylbenzene per minute is from 0.2 to 8L/(min-mol).
6. The process of any one of claims 1-5, wherein the initiator is a peroxide initiator or an azo initiator;
preferably, the peroxide initiator is selected from at least one of hydroperoxy type initiators, diacyl peroxide type initiators, dialkyl peroxide type initiators, diester peroxide type initiators, and peroxy organic acid/ketone initiators;
more preferably, the peroxide initiator is a hydroperoxy type initiator.
7. The method according to claim 6, wherein the hydroperoxy-type initiator is at least one selected from the group consisting of cyclopentylbenzene hydroperoxide, t-butyl hydroperoxide, cyclopentyl-1-phenyl-1-hydroperoxide, cyclohexyl-1-phenyl-1-hydroperoxide, pinane hydroperoxide, 1,3, 3-tetramethylbutyl hydroperoxide, and cumene hydroperoxide.
8. The method of claim 7, wherein the initiator is cyclopentylbenzene hydroperoxide.
9. The process according to any one of claims 1 to 8, wherein the initiator is used in an amount of 0.01 to 5 wt.%, preferably 0.05 to 2 wt.%, based on the weight of cyclopentylbenzene.
10. The method according to any one of claims 1-9, wherein the peroxidation is carried out without addition of a catalyst, preferably a peroxidation catalyst.
CN202010437326.6A 2020-05-21 2020-05-21 Method for preparing hydrogen peroxide cyclopentylbenzene from cyclopentylbenzene Pending CN113698332A (en)

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