Titanium-containing silicon oxides

Abstract

A titanium-containing silicon oxide capable of producing an epoxide in a high yield when used as a catalyst in a reaction for producing an epoxide from an olefin and a hydroperoxide, in which the titanium-containing silicon oxide satisfies all conditions 1 to 5: Condition 1: an average pore diameter is 10 or more; condition 2: 80% or more of the total pore volume has a pore diameter of 5-200; condition 3: the total pore volume is 0.2 cm3 / g or more; condition 4: the D50 of the titanium-containing silicon oxide is from 1.00 mm to 3.30 mm. And Condition 5: the (D90-D10) / D50 of the titanium-containing silicon oxide is 0.35-1.00.

Description

TECHNICAL FIELD

[0001] The present application relates to a method for producing a titanium-containing silicon oxide, a titanium-containing silicon oxide obtainable by the method, and a method for producing an epoxide using the titanium-containing silicon oxide as a catalyst. BACKGROUND

[0002] A method for producing an epoxide from a hydroperoxide and an olefin in the presence of a catalyst is well known. As the catalyst used in the method, a titanium-containing silicon oxide catalyst obtained by a production method including a molding process such as compression molding is described, for example, in Patent Literature 1.

[0003] PRIOR ART DOCUMENTS

[0004] PATENT LITERATURE

[0005] Patent Literature 1: Japanese Patent Application Laid-Open No. 2001-286768 SUMMARY

[0006] PROBLEMS TO BE SOLVED BY THE INVENTION

[0007] A method for producing an epoxide from an olefin and a hydroperoxide with a high yield is desired.

[0008] MEANS FOR SOLVING THE PROBLEMS

[0009] The present application relates to the following, but is not limited thereto.

[0010] [INVENTION 1]

[0011] A titanium-containing silicon oxide, wherein the titanium-containing silicon oxide satisfies all of Condition 1 to Condition 5, Condition 1: the average pore diameter is 10 or more; Condition 2: 80% or more of the total pore volume has a pore diameter of 5 to 200 ; Condition 3: the total pore volume is 0.2 cm 3 / g or more; Condition 4: the D50 of the titanium-containing silicon oxide is 1.00 mm to 3.30 mm; and Condition 5: the (D90-D10) / D50 of the titanium-containing silicon oxide is 0.35 to 1.00.

[0012] [INVENTION 2]

[0013] The titanium-containing silicon oxide according to Invention 1, wherein the titanium-containing silicon oxide is obtainable by a method including: using a quaternary ammonium ion represented by Formula I as a templating agent, and then removing the templating agent by a solvent extraction operation, [NR 1 R 2 R 3 R 4 ] + I (in the formula, R 1 represents a hydrocarbon group of C 2～36 , and R 2 to R 4 each independently represent a hydrocarbon group of C 1～6 ).

[0014] [Invention 3]

[0015] The titanium-containing silicon oxide according to Invention 1 or 2, wherein the titanium-containing silicon oxide is used for producing an epoxide from an olefin and a hydroperoxide.

[0016] [Invention 4]

[0017] The titanium-containing silicon oxide according to Invention 3, wherein the olefin is propylene, and the hydroperoxide is cumene hydroperoxide.

[0018] [Invention 5]

[0019] A method for producing a titanium-containing silicon oxide, wherein the method for producing a titanium-containing silicon oxide comprises the following steps: a raw material mixing step of obtaining a solid containing a silicon oxide and a templating agent by mixing a silicon source, a templating agent, and a solvent; a templating agent removing step of obtaining a solid by removing the templating agent from the solid obtained in the raw material mixing step; a silylation step of obtaining a solid containing a silylated silicon oxide by bringing the solid obtained in the templating agent removing step into contact with a silylating agent; a titanium introducing step of introducing titanium into the solid at at least one timing selected from the group consisting of within the raw material mixing step, after the raw material mixing step and before the templating agent removing step, within the templating agent removing step, after the templating agent removing step and before the silylation step, within the silylation step, and after the silylation step; a particle size distribution adjusting step of adjusting the particle size distribution of the solid supplied to the present step at at least one timing selected from the group consisting of after the raw material mixing step and before the templating agent removing step, within the templating agent removing step, after the templating agent removing step and before the silylation step, within the silylation step, and after the silylation step, so that the final product of the titanium-containing silicon oxide satisfies the following condition: D50 of the solid: 1.00 mm to 3.30 mm; and (D90-D10) / D10 of the solid: 0.35 to 1.00.

[0020] [Invention 6]

[0021] The method according to Invention 5, wherein the method comprises: a shaping step of shaping the solid obtained at at least one timing selected from the group consisting of after the raw material mixing step, after the template removal step, and after the silylation step, thereby obtaining a solid as a shaped body.

[0022] [Invention 7]

[0023] The method according to Invention 6, wherein the solid obtained through the shaping step is subjected to a particle size distribution adjustment step.

[0024] [Invention 8]

[0025] The method according to Invention 7, wherein the particle size distribution adjustment step comprises fractionation of the solid.

[0026] [Invention 9]

[0027] The method according to Invention 8, wherein the fractionated solids are mixed in the particle size distribution adjustment step.

[0028] [Invention 10]

[0029] A titanium-containing silicon oxide, wherein the titanium-containing silicon oxide can be obtained by the method according to any one of Inventions 5 to 9.

[0030] [Invention 11]

[0031] Use of the titanium-containing silicon oxide according to any one of Inventions 1 to 4 and 10 for producing an epoxide from an olefin and a hydroperoxide.

[0032] [Invention 12]

[0033] The use according to Invention 11, wherein the olefin is propylene and the hydroperoxide is cumene hydroperoxide.

[0034] [Invention 13]

[0035] A method for producing an epoxide, wherein the method comprises a step of reacting an olefin with a hydroperoxide in the presence of the titanium-containing silicon oxide according to any one of Inventions 1 to 4 and 10.

[0036] [Invention 14]

[0037] The method according to the application 13, wherein the olefin is propylene and the hydroperoxide is cumene hydroperoxide.

[0038] Effects of the Invention

[0039] According to one embodiment of the present application, in the case where the titanium-containing silicon oxide of the present application is used as a catalyst in a reaction for generating an epoxide (e.g., propylene oxide) from an olefin (e.g., propylene) and a hydroperoxide (e.g., cumene hydroperoxide), the epoxide can be produced at a high yield. DETAILED DESCRIPTION

[0040] Definitions

[0041] In the present specification, the term "solution" includes not only a uniform liquid but also a mixture in a colloidal or suspended state, and a gas-liquid mixture.

[0042] In the present specification, the term "α-olefin" means a hydrocarbon having a carbon-carbon unsaturated double bond at an α-position.

[0043] In the present specification, the term "C X～Y means a hydrocarbon group having X to Y carbon atoms.

[0044] The recitation of a numerical range "from lower limit to upper limit" means "from the lower limit or more and the upper limit or less", and the recitation of "from upper limit to lower limit" means "from the upper limit or less and the lower limit or more". That is, these recitations mean a numerical range including the lower limit and the upper limit, but in one embodiment, one or both of the lower limit and the upper limit can be excluded, that is, "from lower limit to upper limit" can mean "more than the lower limit and equal to or less than the upper limit", "equal to or more than the lower limit and less than the upper limit", or "more than the lower limit and less than the upper limit". Similarly, "xx or more" can mean "more than xx", and "xx or less" can mean "less than xx".

[0045] Titanium-Containing Silicon Oxide

[0046] The titanium-containing silicon oxide means a compound having a bond represented by Si-O-Ti.

[0047] The titanium-containing silicon oxide of the present application satisfies all of the conditions 1 to 5.

[0048] Condition 1

[0049] The average pore diameter of the titanium-containing silicon oxide of the present application is 10 or more, and preferably 20 or more.

[0050] Condition 2

[0051] The titanium-containing silicon oxide of the present application has 80% or more of the total pore volume in pores having a diameter of 5 to 200 the pore diameter is preferably 5

[0052] Condition 3

[0053] The total pore volume of the titanium-containing silicon oxide of the present application is 0.2 cm 3 / g or more. Here, the total pore volume refers to the total pore volume per 1 g of the titanium-containing silicon oxide. The total pore volume is preferably 0.5 cm 3 / g or more.

[0054] The measurement regarding Condition 1 to Condition 3 can be performed by a physical adsorption method using a gas such as nitrogen, argon, and the like, by a usual method. For example, the measurement is performed according to the method described in the examples.

[0055] Condition 4

[0056] The D50 of the titanium-containing silicon oxide of the present application is 1.00 mm to 3.30 mm. Here, the D50 refers to the particle diameter corresponding to the cumulative value of the particle size distribution of the titanium-containing silicon oxide reaching 50%. The particle size distribution referred to here is on a volume basis. The D50 is preferably 1.00 mm to 3.00 mm, more preferably 1.00 mm to 2.50 mm, and further preferably 1.00 mm to 2.00 mm.

[0057] Condition 5

[0058] The (D90-D10) / D50 of the titanium-containing silicon oxide of the present application is 0.35 to 1.00. Here, the D90 and D10 each refer to the particle diameter corresponding to the cumulative value of the particle size distribution of the titanium-containing silicon oxide reaching 90% and 10%, respectively. The particle size distribution referred to here is on a volume basis. The (D90-D10) / D50 is preferably 0.35 to 0.80, and more preferably 0.35 to 0.75.

[0059] The measurement of the particle size distribution in Condition 4 and Condition 5 can be performed by, for example, analysis of an image taken. The adjustment of the particle size distribution is performed by, for example, classifying the powder aggregate (particle aggregate, broken product aggregate) of the titanium-containing silicon oxide into a plurality of particle size ranges, selecting one of them or selecting the classified aggregates of a plurality of ranges and mixing them at a prescribed ratio. More specifically, the measurement and adjustment are performed according to the method described in the examples.

[0060] In one mode, the titanium-containing silicon oxide of the present application can be obtained by a method including a step of using a quaternary ammonium ion represented by Formula I as a template, and then removing the template by a solvent extraction operation. The details are described later together with the production method.

[0061] Production method​​

[0062] The method for producing a titanium-containing silicon oxide of the present application includes a raw material mixing step, a template removing step, a silylation step, a titanium introducing step, and a particle size distribution adjusting step.

[0063] Raw material mixing step (Step A)

[0064] The raw material mixing step is a step of mixing a silicon source, a template agent, and a solvent to obtain a solid containing a silicon oxide and a template agent, and is also referred to as Step A.

[0065] The "silicon source" refers to a silicon oxide and a silicon oxide precursor. The silicon oxide precursor refers to a compound that makes a part or all of the silicon oxide precursor into a silicon oxide by reacting the silicon oxide precursor with water.

[0066] As examples of the silicon oxide, amorphous silica can be given. As examples of the above-mentioned silicon oxide precursor, alkoxysilane, alkyltrialkoxysilane, dialkyldialkoxysilane, and 1,2-bis(trialkoxysilyl)alkane can be given. As examples of the alkoxysilane, tetramethyl orthosilicate, tetraethyl orthosilicate, and tetrapropyl orthosilicate can be given. As examples of the alkyltrialkoxysilane, trimethoxy(methyl)silane can be given. As examples of the dialkyldialkoxysilane, dimethoxydimethylsilane can be given. As the silicon source, a single silicon source can be used, or a plurality of silicon sources can be used in combination.

[0067] In the case where a silicon oxide precursor is used as the silicon source, it is preferable to use water as a part or all of the solvent in Step A. When the silicon oxide precursor is mixed with water, a part or all of the silicon oxide precursor becomes a silicon oxide.

[0068] A template agent is a substance capable of forming a porous structure in titanium-containing silicon oxides. Surfactants are preferred as template agents. Examples of surfactants include cationic surfactants, anionic surfactants, and nonionic surfactants. Examples of cationic surfactants include quaternary ammonium compounds containing quaternary ammonium ions and alkylamine salts. Examples of quaternary ammonium compounds containing quaternary ammonium ions include tetraalkylammonium hydrochloride, tetraalkylammonium acetate, and tetraalkylammonium hydroxide. Examples of alkylamine salts include monoalkylamine hydrochloride, monoalkylamine acetate, dialkylamine hydrochloride, dialkylamine acetate, trialkylamine hydrochloride, and trialkylamine acetate. Examples of anionic surfactants include alkylbenzene sulfonic acids and their salts, sodium α-olefin sulfonate salts, alkyl sulfate salts, alkyl ether sulfate salts, methyl taurine, alanine and its salts, ether carboxylic acids and their salts, sulfosuccinates, sulfated oils, polyoxyalkylene ether sulfate salts, and soaps. Examples of nonionic surfactants include polyepoxides or block copolymers of polyepoxides and alkylamines.

[0069] As surfactants, cationic surfactants and nonionic surfactants are preferred. As cationic surfactants, compounds (e.g., salts) containing quaternary ammonium ions represented by Formula I are preferred. As nonionic surfactants, amines represented by Formula II are preferred.

[0070] [NR 1 R 2 R 3 R 4 ] + I

[0071] (In equation I, R) 1 C represents 2～36 The (straight-chain or branched) hydrocarbon group, R 2 ~R 4 Each represents C independently. 1～6 (The hydrocarbon group.)

[0072] NR 5 R 6 R 7 II

[0073] (In Equation II, R) 5 C represents 2～36 The (straight-chain or branched) hydrocarbon group, R 6 and R 7 Each independently represents a hydrogen atom or a carbon atom. 1～6 (The hydrocarbon group.)

[0074] In equation I, R 1 C 2～36The hydrocarbon group can be straight-chain or branched, and can be aliphatic or aromatic. C is preferred. 10～22 The hydrocarbon group, more preferably C 10～22 A straight-chain hydrocarbon group. R 2 ~R 4 Each independently is C 1～6 The hydrocarbon group is preferably aliphatic and can be linear or branched. More preferably, R... 2 ~R 4 All are methyl groups.

[0075] Examples of quaternary ammonium ions represented by Formula I include: tetraethylammonium, tetrapropylammonium, tetrabutylammonium, decyltrimethylammonium, dodecyltrimethylammonium, hexadecyltrimethylammonium, octadecyltrimethylammonium, eicosyltrimethylammonium, dodecyltrimethylammonium, benzyltrimethylammonium, dimethyl di(dodecyl)ammonium, and hexadecylpyridine, etc.

[0076] Examples of salts containing quaternary ammonium ions represented by Formula I include: tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, decyltrimethylammonium hydroxide, decyltrimethylammonium chloride, decyltrimethylammonium bromide, dodecyltrimethylammonium hydroxide, dodecyltrimethylammonium chloride, dodecyltrimethylammonium bromide, hexadecyltrimethylammonium hydroxide, hexadecyltrimethylammonium chloride, hexadecyltrimethylammonium bromide, octadecyltrimethylammonium hydroxide, octadecyltrimethylammonium chloride, octadecyltrimethylammonium bromide, eicosyltrimethylammonium hydroxide, eicosyltrimethylammonium chloride, eicosyltrimethylammonium bromide, dodecyltrimethylammonium hydroxide, dodecyltrimethylammonium chloride, and dodecyltrimethylammonium bromide, as well as dimethyl dialkylammonium salts and methyl trialkylammonium salts of these salts containing quaternary ammonium ions in which at least one methyl group is substituted with an alkyl group having 2 to 22 carbon atoms.

[0077] In Equation II, R 5 C 2～36 A straight-chain or branched hydrocarbon group, preferably C 10～22 The hydrocarbon group, more preferably C 10～22 A straight-chain hydrocarbon group. R 6 and R 7 Each is independently a hydrogen atom or a carbon atom. 1～6 Hydrocarbon group, preferably R 6 and R 7 It can be a hydrogen atom or a methyl group.

[0078] As specific examples of the amine represented by formula II, there can be mentioned ethylamine, propylamine, butylamine, octylamine, nonylamine, decylamine, undecylamine, dodecylamine, tridecylamine, tetradecylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, nonadecylamine, eicosylamine, and docosylamine, and methylalkylamines and dimethylalkylamines in which at least one hydrogen atom of these amines is substituted with a methyl group, and the like.

[0079] As the template agent, a single template agent can be used, or a plurality of template agents can be used in combination.

[0080] The mixing of the template agent, the silicon source, and the template agent is performed in the presence of a solvent. As examples of the solvent, there can be mentioned water, an alcohol. As examples of the alcohol, there can be mentioned methanol, ethanol, 1-propanol, 2-propanol. Two or more kinds of solvents can be used in combination, and a mixed solvent of water and methanol can be mentioned. The solvent can be imparted with acidity or basicity, and basicity is preferred.

[0081] By carrying out the process A, a solid containing the template agent and the silicon oxide will be obtained. The process A can include a solvent removal process. The obtained solid can be taken out by filtration, decantation, drying, centrifugal separation, a combination thereof, or the like. The mixing of the process A is preferably performed at a temperature ranging from 0°C to 300°C for 30 minutes to 1000 hours. In one embodiment, the mixing can be performed at 20°C to 100°C, at the boiling point of the solvent, at 20°C to 60°C, or at 20°C to 40°C. In one embodiment, the mixing can be performed for 30 minutes to 24 hours, or for 2 hours to 24 hours. In addition, stirring can be performed in the mixing.

[0082] Template agent removal process (process B)

[0083] The template agent removal process is a process of removing the template agent from the solid obtained by the process A, thereby obtaining a solid containing the silicon oxide, and is also referred to as process B. By carrying out the process B, a solid not containing the template agent or substantially not containing the template agent will be obtained.

[0084] In the present specification, "obtained by the process X" can mean "obtained in the process X", or can mean "obtained by carrying out the process X and one or more other processes that follow". Similarly, "after the process X" can mean "immediately after the process X", or can mean "after the process X and one or more other processes that follow".

[0085] The content of the template agent in the solid obtained in the process B is preferably 10% by mass or less, and more preferably 1% by mass or less.

[0086] The removal of the template agent can be achieved, for example, by calcining the solid containing the template agent in air at 300°C to 800°C, or by solvent extraction. The template agent is preferably removed by extraction.

[0087] Whitehurst et al. reported a technique for extracting the template agent using a solvent (see U.S. Patent No. 5143879). The solvent can be any solvent that can dissolve the compound used as the template agent, and a C 1～12 compound, or a mixture of two or more of these compounds. As examples of suitable solvents, there can be mentioned alcohols, ketones, acyclic and cyclic ethers, and esters. As examples of alcohols, there can be mentioned methanol, ethanol, ethylene glycol, propylene glycol, 1-propanol, 2-propanol, 1-butanol, and octanol. As examples of ketones, there can be mentioned acetone, diethyl ketone, methyl ethyl ketone, and methyl isobutyl ketone. As examples of ethers, there can be mentioned diisobutyl ether and tetrahydrofuran. As examples of esters, there can be mentioned methyl acetate, ethyl acetate, butyl acetate, and butyl propionate.

[0088] As the solvent, from the viewpoint of the solubility of the template agent, for example, in the case where the template agent is a compound containing a quaternary ammonium ion, an alcohol is preferred, with methanol being more preferred. The mass ratio of the solvent to the solid containing the template agent is usually 1 to 1000, and preferably 5 to 300. In order to improve the extraction efficiency, an acid or a salt thereof can be added to the solvent. As examples of the acid used, there can be mentioned inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, and hydrobromic acid, or organic acids such as formic acid, acetic acid, and propionic acid. As examples of the salt thereof, there can be mentioned alkali metal salts, alkaline earth metal salts, and ammonium salts. The concentration of the acid or the salt thereof added to the solvent is preferably 30% by mass or less, and more preferably 15% by mass or less.

[0089] As an example of the method for removing the template agent, there can be mentioned a method in which the solvent and the solid containing the template agent are mixed sufficiently, and then the liquid phase is separated by filtration, decantation, or the like. This operation can also be repeated a plurality of times. Alternatively, the template agent can be extracted by a method in which the solid containing the template agent is packed into a container such as a column, and an extraction solvent is caused to flow therethrough. The extraction temperature is preferably 0°C to 200°C, and more preferably 20°C to 100°C. In the case where the boiling point of the extraction solvent is low, the extraction can be performed under pressure.

[0090] The template agent in the solution obtained by the extraction treatment can be recovered and reused as the template agent of Step A. Ion exchange or the like can also be performed at the time of recovery and reuse. Also, likewise, the extraction solvent can be purified by a usual distillation operation or the like and reused.

[0091] Silylation step (Step C)

[0092] The silylation step is a step of obtaining a solid containing silylated silicon oxide by contacting the solid obtained in Step B with a silylating agent, and is also referred to as Step C. By carrying out Step C, the solid obtained in Step B is silylated.

[0093] The silylation can be performed by a gas phase method of contacting and reacting a gaseous silylating agent with the solid obtained in Step B, or by a liquid phase method of contacting and reacting a silylating agent with the solid in a solvent. In one embodiment of the present application, the liquid phase method is preferred. In general, in the case where the silylation is performed by the liquid phase method, a hydrocarbon is suitably used as the solvent in Step C. When the silylation is performed by the liquid phase method, drying can be performed thereafter.

[0094] The silylating agent refers to a silicon compound having the above-described silylation reactivity with respect to the solid, and is a compound in which at least one or more groups selected from the group consisting of alkyl groups, vinyl groups and allyl groups, aryl groups such as phenyl groups, halogenated alkyl groups, and silyloxy groups are bonded to silicon, and a hydrolyzable group is bonded to the silicon. As the hydrolyzable group bonded to the silicon, hydrogen, halogen, alkoxy, acetoxy, and amino can be exemplified. In the silylating agent, the hydrolyzable group bonded to the silicon is preferably one.

[0095] As examples of the silylating agent, organosilane, organosilylamine, organosilylamide and derivatives thereof, and organosilazane can be exemplified.

[0096] As examples of organosilanes, there can be mentioned chlorotrimethylsilane, dichlorodimethylsilane, chlorobromodimethylsilane, nitrottrimethylsilane, chlorotriethylsilane, iododimethylbutylsilane, chlorodimethylphenylsilane, chlorodimethylsilane, dimethyl-n-propylchlorosilane, dimethylisopropylchlorosilane, t-butyldimethylchlorosilane, tripropylchlorosilane, dimethyloctylchlorosilane, tributylchlorosilane, trihexylchlorosilane, dimethylethylchlorosilane, dimethyloctadecylchlorosilane, n-butyldimethylchlorosilane, bromomethyldimethylchlorosilane, chloromethyldimethylchlorosilane, 3-chloropropyldimethylchlorosilane, dimethoxymethylchlorosilane, methylphenylchlorosilane, methylphenylvinylchlorosilane, benzyl dimethylchlorosilane, diphenylchlorosilane, diphenylmethylchlorosilane, diphenylvinylchlorosilane, tribenzylchlorosilane, methoxytrimethylsilane, dimethoxydimethylsilane, trimethoxymethylsilane, ethoxytrimethylsilane, diethoxydimethylsilane, triethoxymethylsilane, triethoxyethylsilane, diethoxydiethylsilane, methoxytriethylsilane, ethoxytriethylsilane, diethoxydiethylsilane, triethoxyethylsilane, methoxytriphenylsilane, dimethoxydiphenylsilane, trimethoxyphenylsilane, ethoxytriphenylsilane, diethoxydiphenylsilane, triethoxyphenylsilane, dichlorotetramethyldisiloxane, 3-cyanopropyldimethylchlorosilane and 1,3-dimethoxy-l,l,3,3-tetramethyldisiloxane.

[0097] As examples of organosilylamines, there can be mentioned N-(trimethylsilyl)imidazole, N-(t-butyldimethylsilyl)imidazole, N-(dimethylethylsilyl)imidazole, N-(dimethyl-n-propylsilyl)imidazole, N-(dimethylisopropylsilyl)imidazole, N-(trimethylsilyl)-N,N-dimethylamine, N-(trimethylsilyl)-N,N-diethylamine, N-(trimethylsilyl)pyrrole, N-(trimethylsilyl)pyrrolidine, N-(trimethylsilyl)piperidine, 1-cyanoethyl(diethylamino)dimethylsilane and pentafluorophenyldimethylsilylamine.

[0098] As examples of organosilylamides and derivatives thereof, there can be mentioned N,O-bis(trimethylsilyl)acetamide, N,O-bis(trimethylsilyl)trifluoroacetamide, N-(trimethylsilyl)acetamide, N-methyl-N-(trimethylsilyl)acetamide, N-methyl-N-(trimethylsilyl)trifluoroacetamide, N-methyl-N-(trimethylsilyl)heptafluorobutyramide, N-(t-butyldimethylsilyl)-N-methyltrifluoroacetamide and N,O-bis(diethylhydro silyl)trifluoroacetamide.

[0099] As examples of the organosilazane, there can be mentioned 1,1,1,3,3,3-hexamethyldisilazane, heptamethyldisilazane, 1,1,3,3-tetramethyldisilazane, 1,3-bis(chloromethyl)- 1,1,3,3-tetramethyldisilazane, 1,3-divinyl-1,1,3,3-tetramethyldisilazane, and 1,3-diphenyl-1,1,3,3-tetramethyldisilazane.

[0100] As other examples of the silylating agent, there can be mentioned N-methoxy-N- (trimethylsilyl)trifluoroacetamide, N-methoxy-O-(trimethylsilyl)carbamate, N,O- bis(trimethylsilyl)sulfamate, trimethylsilyl trifluoromethanesulfonate, and N,N'- bis(trimethylsilyl)urea. The preferred silylating agent is an organosilazane, more preferably 1,1,1,3,3,3-hexamethyldisilazane.

[0101] Titanium-introducing step (step D)

[0102] The titanium-introducing step is a step of introducing titanium into the solid, and is also referred to as step D. Step D is performed at at least one timing selected from the group consisting of within step A, within step B, within step C, between step A and step B, between step B and step C, and after step C.

[0103] The introduction of titanium can be performed at both of the aforementioned timings within the step and between the steps.

[0104] In the present specification, "introducing titanium" means introducing a bond represented by -Si-O-Ti into the silicon oxide contained in the solid by mixing the solid containing the silicon oxide with a titanium source.

[0105] It is preferred that titanium be introduced before the start of step C, more preferably at at least one or more timings selected from the group consisting of within step A, between step B and step C, and further preferably within step A.

[0106] The introduction of titanium within step A is performed, for example, by mixing the silicon source, the titanium source, and the templating agent within step A.

[0107] It is also possible to contact the solid obtained through step A with a titanium source after the end of step A and before the start of step B, thereby introducing titanium into the solid.

[0108] It is also possible to contact the solid obtained through step B with a titanium source after the end of step B and before the start of step C, thereby introducing titanium into the solid.

[0109] The titanium can be introduced into the solid by contacting the solid into which the titanium is to be introduced with a titanium source in a liquid phase, or by contacting a gas containing the titanium source with the solid into which the titanium is to be introduced.

[0110] As examples of the titanium source, there can be mentioned titanium alkoxides, chelate-type titanium complexes, titanium halides, and titanium-containing sulfates. As examples of the titanium alkoxides, there can be mentioned tetramethyl titanate, tetraethyl titanate, tetrapropyl titanate, tetraisopropyl titanate, tetrabutyl titanate, tetraisobutyl titanate, tetra(2-ethylhexyl) titanate, and tetra(octadecyl) titanate. As examples of the chelate-type titanium complexes, there can be mentioned titanium (IV) acetylacetonate and titanium (IV) diisopropoxydiacetylacetonate. As examples of the titanium halides, there can be mentioned titanium tetrachloride, titanium tetrabromide, and titanium tetraiodide. As examples of the titanium-containing sulfates, there can be mentioned titanyl sulfate.

[0111] Particle size distribution adjusting step (step E)

[0112] The particle size distribution adjusting step is a step of adjusting the particle size distribution of the solid, and is also referred to as step E. By this step, the D50 of the titanium-containing silicon oxide of the final product is adjusted to 1.00 mm to 3.30 mm, and the (D90-D10) / D50 is adjusted to 0.35 to 1.00. Note that this step can be performed in the final step of the production of the titanium-containing silicon oxide, or can be performed at an intermediate stage (for example, after step A). In the case where this step is performed at an intermediate stage, the particle size distribution adjusted at the stage is not limited to coincide with the particle size distribution of the titanium-containing silicon oxide of the final product, but the particle size distribution at the stage needs to be adjusted while taking into consideration the particle size distribution of the titanium-containing silicon oxide of the final product.

[0113] Note that, as described above, the D50 refers to the particle size corresponding to the cumulative value of the particle size distribution of the solid (titanium-containing silicon oxide) reaching 50%. The D50 is preferably 1.00 mm to 3.00 mm, more preferably 1.00 mm to 2.50 mm, and further preferably 1.00 mm to 2.00 mm.

[0114] The D90 and D10 refer to the particle sizes corresponding to the cumulative values of the particle size distribution of the titanium-containing silicon oxide reaching 90% and 10%, respectively. The (D90-D10) / D50 is preferably 0.35 to 0.80, and more preferably 0.35 to 0.75.

[0115] As described above, the measurement of the particle size distribution can be performed, for example, by analysis of an image. More specifically, the measurement is performed according to the method described in the examples. The adjustment of the particle size distribution can be performed by classification using a sieve, for example, by classifying the powder aggregate (particle aggregate, broken aggregate) of the titanium-containing silicon oxide into a plurality of particle size ranges, appropriately selecting and mixing the classified aggregates from the plurality of ranges in a prescribed ratio, or selecting the mesh size of the sieve in a manner to become the target particle size distribution.

[0116] Preferably, the process E is performed after the process P described later.

[0117] Shaping process (process P)

[0118] In one embodiment, the production method of the titanium-containing silicon oxide of the present application includes a shaping process. The shaping process is a process of shaping the solid obtained in the process A, thereby obtaining a shaped body. It is also sometimes referred to as process P. As an example of the shaping method, compression molding can be given. In this compression molding, for example, from the viewpoints of catalyst strength, catalyst physical properties, and productivity, roll press molding using a roll press or extrusion molding using a disc granulator is preferably employed. In the shaping, a generally used organic and inorganic binder can be used.

[0119] The obtained shaped body is usually crushed to an appropriate size and used in the next process, for example, the particle size distribution adjustment process. The crushing process can also be considered as one of the processes performed in the particle size distribution adjustment process.

[0120] Liquid replacement process (process Q)

[0121] In one embodiment, the production method of the titanium-containing silicon oxide of the present application includes a liquid replacement process. The liquid replacement process is a process of replacing the solvent remaining in the solid obtained in the process B with a liquid which is substantially inert to the silylating agent, and is also sometimes referred to as process Q. As examples of the liquid which is substantially inert, hydrocarbons, halogenated alkanes, and ethers can be given. As examples of the hydrocarbons, aliphatic hydrocarbons and aromatic hydrocarbons of C 6～14 1-6 can be given. As examples of the halogenated alkanes, dichloromethane and tetrachloroethylene can be given. As examples of the ethers, diethyl ether and tetrahydrofuran can be given. Among them, hydrocarbons are preferred, and toluene is more preferred. The temperature of the liquid for replacement in the liquid replacement is usually from 0°C to 200°C. The liquid replacement can be performed by a batch method or a flow-through method.

[0122] Drying process (process R)

[0123] In one embodiment, the method for producing the titanium-containing silicon oxide of the present application includes a drying step. The drying step is a step of drying the solid obtained in Step B, and is also referred to as Step R. When this step is performed, it is preferable to perform it under normal pressure or reduced pressure. The preferable temperature varies depending on the treatment liquid, but from the viewpoint of catalyst performance, it is usually from 0°C or higher to 700°C or lower, and preferably from 0°C or higher to 200°C or lower. The drying can be performed by a batch method or a gas flow method.

[0124] Step R (drying step) can also be performed after Step Q (liquid displacement step).

[0125] Not only can drying be performed after Step B, but also when Steps A to B are performed, drying of the solid can be performed under the same conditions as Step R after the end of any of these steps and before the next step. Also, either or both of Step Q and Step R can be performed after Step B and before Step C.

[0126] Use

[0127] The titanium-containing silicon oxide of the present application can be used as a catalyst for the oxidation reaction of an organic compound, such as the epoxidation reaction of an olefin, and is particularly preferably used for producing an epoxide by reacting an olefin with a hydroperoxide.

[0128] The olefin for the epoxidation reaction can be an acyclic olefin, a monocyclic olefin, a bicyclic olefin, or a polycyclic olefin having three or more rings, and can be a mono-olefin, a di-olefin, or a poly-olefin. In the case where the olefin has two or more double bonds within the molecule, these double bonds can be conjugated bonds, or can be non-conjugated bonds. Preferred are olefins having C 2～60 The olefin can have a substituent. Examples of such an olefin can include ethylene, propylene, 1-butene, isobutylene, 1-hexene, 2-hexene, 3-hexene, 1-octene, 1-decene, styrene, and cyclohexene. A substituent containing an oxygen atom, a sulfur atom, or a nitrogen atom together with a hydrogen atom or a carbon atom, or both, can be present in the olefin, and examples of such an olefin can include allyl alcohol, crotyl alcohol, and allyl chloride. Examples of di-olefins can include butadiene and isoprene. Examples of preferred olefins can include a-olefins. Examples of particularly preferred olefins can include propylene.

[0129] The method for producing propylene used in the epoxidation reaction is not particularly limited, and propylene produced by the following production methods can be used. Examples include cracking of naphtha or ethane, fluid catalytic cracking of vacuum gas oil, dehydrogenation of propane, dismutation of ethylene and 2-butene, MTO (methanol to olefin) reaction of converting methanol or dimethyl ether, Fischer-Tropsch (FT) synthesis of reacting carbon monoxide and hydrogen, dehydration of isopropyl alcohol, and the like. In addition, propylene produced by a method for reducing the load on the environment, such as a method for producing propylene from bioethanol and / or isopropyl alcohol produced using plants as raw materials, an FT synthesis method using carbon dioxide or biomass, and a method for catalytic cracking of waste plastics, and the like can also be used.

[0130] Examples of the hydroperoxide include organic hydroperoxides. The organic hydroperoxide is a compound having Formula III.

[0131] R-O-O-H III

[0132] (In Formula III, R is a hydrocarbon group.)

[0133] The organic hydroperoxide reacts with the olefin to produce an epoxide and a hydroxyl compound. R in Formula III is preferably a hydrocarbon group of C 3～20 , and more preferably a hydrocarbon group of C 3～10 . It can be linear or branched, and aliphatic or aromatic. Examples of the organic hydroperoxide include t-butyl hydroperoxide, 1-phenylethyl hydroperoxide, and cumene hydroperoxide. Hereinafter, cumene hydroperoxide is sometimes referred to simply as CMHP.

[0134] When CMHP is used as the organic hydroperoxide, the resulting hydroxyl compound is 2-phenyl-2-propanol. This 2-phenyl-2-propanol is converted into cumene by dehydration and hydrogenation. Hereinafter, cumene is sometimes referred to simply as CUM. Furthermore, by oxidizing this CUM, CMHP can be obtained again. From this viewpoint, it is preferable to use CMHP as the organic hydroperoxide used in the epoxidation reaction.

[0135] The epoxidation reaction can be carried out in a liquid phase using a solvent, a diluent, or a mixture thereof. The solvent and the diluent are preferably liquid at the temperature and pressure at the time of the reaction, and are substantially inert to the reactants and the products. In the case where CMHP is subjected to the epoxidation reaction in the presence of CUM, which is a raw material thereof, CUM can be used as the solvent without particular addition of a solvent.

[0136] The epoxidation reaction temperature is usually a temperature of 0°C to 200°C, and preferably 25°C to 200°C. The epoxidation reaction pressure can be a pressure sufficient to maintain the reaction phase in a liquid state, and is usually preferably 100 kPa to 10,000 kPa.

[0137] After the epoxidation reaction is completed, the liquid mixture containing the desired product can be separated from the titanium-containing silicon oxide. Next, the liquid mixture can be purified by an appropriate method. As examples of the purification method, distillation, extraction, and washing can be listed. The solvent and unreacted olefin can be recycled and reused.

[0138] The reaction using the titanium-containing silicon oxide of the present application as a catalyst, such as oxidation of an epoxide, can be performed in the form of a slurry or a fixed bed, and in the case of large-scale industrial operation, a fixed bed is preferably used. In the above use, the titanium-containing silicon oxide can be a powder or a shaped body (a shaped body obtained by a shaping process). In the case where the reaction is performed in a fixed bed, the titanium-containing silicon oxide is preferably a shaped body. The present reaction can be performed by a batch, a semi-continuous method, or a continuous method.

[0139] Example

[0140] Hereinafter, one embodiment of the present application will be described in more detail by way of examples.

[0141] Example 1

[0142] (1) Raw material mixing process and titanium introduction process

[0143] Hexadecyltrimethylammonium hydroxide diluted to a concentration of 16 mass% using a mixed solvent having a mixing ratio (mass ratio) of water:methanol = 72:28 (125 mass parts of a solution at a concentration of 16 mass%) was stirred, and a mixed solution of tetraisopropyl titanate 1.9 mass parts and 2-propanol 10 mass parts was added dropwise thereto at room temperature while stirring. After the dropwise addition was completed, stirring was performed for 30 minutes, and then tetramethyl orthosilicate 38 mass parts was added dropwise while stirring. Then, stirring was continued at room temperature for 3 hours, and the generated solid was filtered out. The obtained solid was dried under reduced pressure at 70°C, and a white solid was obtained. The hexadecyltrimethylammonium hydroxide, the tetramethyl orthosilicate, and the tetraisopropyl titanate were a template agent, a silicon source, and a titanium source, respectively.

[0144] (2) Shaping process

[0145] Water was added to the obtained white solid 15 mass parts so that the moisture content became 1.3 mass parts, and the mixture was sufficiently mixed. Then, the obtained mixture was compression-molded.

[0146] (3) Particle size distribution adjustment process

[0147] The obtained shaped body was crushed, and the crushed product was sieved and classified into A to G shown in the following table. Each classified product was obtained by overlapping two sieves having different mesh sizes in the table below with the larger mesh size as the upper layer, placing the crushed product in the upper sieve and vibrating it for about 3 minutes, and recovering the crushed product remaining on the sieve having the smaller mesh size. Note that in the classification using the sieves, particles having a size between the mesh sizes of the two sieves were not strictly extracted because a particle passes through the sieve as long as one side of the particle is equal to or smaller than the mesh size.

[0148] Table 1

[0149] A to H were mixed in the mass proportions shown in Table 2 below, thereby obtaining the particle size distribution adjusted shaped body used in the examples and comparative examples.

[0150] (4) Template removal step

[0151] The above-obtained particle size distribution adjusted shaped body 20 g was filled in a cylindrical glass column having an inner diameter of 30 mm (sheath tube outer diameter 8 mm) and a height of 27 cm arranged vertically. Then, the following three kinds of solutions were passed upward from the lower part of the column in this order. First, 141 g of methanol was passed at a liquid passing rate = 3.5 g / min at a column temperature of 25°C. Next, a mixed solution of 326 g of methanol and 8 g of concentrated hydrochloric acid (hydrogen chloride content 36 mass%) was passed at a liquid passing rate = 3.0 g / min at a column temperature of 38°C. Next, 190 g of methanol was passed at a liquid passing rate = 3.5 g / min at a column temperature of 38°C, and then 126 g of methanol was passed at a liquid passing rate = 3.5 g / min while the column was cooled to 25°C. Then, the solution containing the template and methanol in the column was drawn from the lower part of the column.

[0152] (5) Liquid replacement step

[0153] Next to the template removal step, 47 g of toluene was passed into the column at a liquid passing rate = 2.8 g / min at a column temperature of 75°C, and then 157 g of toluene was passed while the column temperature was raised to 90°C. Thus, the above mixed solution remaining in the column at the end of the template removal step was replaced with toluene. Then, the toluene in the column was drawn from the lower part of the column. Then, nitrogen was made to flow upward from the lower part of the column in the column at a flow rate of 50 NmL / min at a column temperature of 120°C, and after confirming that the distillation of the liquid from the upper part of the column had stopped, the flow rate was changed to 150 NmL / min, and the nitrogen was made to flow for a total of 2 hours, thereby drying the shaped body. Thus, a solid was obtained.

[0154] (6) Silylation step

[0155] Next, the liquid displacement process was performed by passing a mixed solution of 1,1,1,3,3,3-hexamethyldisilazane (hereinafter also referred to as HMDS) 7.5 g and toluene 92.5 g at a column temperature of 100°C and a liquid passing rate of 3.9 g / min from the lower part of the column. At this time, the liquid that had passed through the column was recovered with a receiver, and the column was continuously circulated for 3 hours with a pump. Thus, silylation of the shaped body in the column was performed. Then, the mixed solution of toluene and HMDS in the column was drawn out from the lower part of the column. Then, nitrogen was made to flow upward from the lower part of the column in the column at a flow rate of 50 NmL / min at a column temperature of 120°C, and after confirming that the distillation of the liquid from the upper part of the column had stopped, the flow rate was changed to 150 NmL / min, and the nitrogen was made to flow for a total of 2 hours, whereby the shaped body was dried. Thus, a shaped body of a titanium-containing silicon oxide catalyst was obtained.

[0156] (7) Evaluation of pore structure

[0157] In order to evaluate the pore structure of the titanium-containing silicon oxide obtained by the above-described processes (1) to (6), a BELSORP MINIX manufactured by Microtrac BEL Co., Ltd. was used to perform a pretreatment of vacuum heat degassing at 120°C for 2 hours, and then nitrogen adsorption measurement of the titanium-containing silicon oxide was performed, and the average pore diameter and the pore volume were calculated by a pore distribution calculation based on the BJH method. In addition, the ratio of the pore volume of 5 to 200 A was calculated. The pore structure is shown in Table 2.

[0158] (8) Measurement method of particle size distribution of catalyst

[0159] The particle diameters corresponding to the cumulative values of 90%, 50%, and 10% of the particle size distribution of the catalyst, namely, D90, D50, and D10, were measured by the following described method.

[0160] The catalyst shaped body of 5 ml obtained by the above-described processes (1) to (6) was dispersed on a black paper in a manner that the particles did not overlap, and an image was captured using a digital camera. Using an image analysis software (Image J 1.53), the area of the particles in the image was calculated and the square root was taken, whereby the particle diameter of the catalyst shaped body was calculated. The particle size distribution was prepared from the obtained particle diameter, and the values of D90, D50, and D10 were calculated. The values of D90, D50, and D10 are shown in Table 2.

[0161] (9) Evaluation of catalyst performance

[0162] The evaluation of the catalyst performance was performed by the following described method.

[0163] • Synthesis of propylene oxide by a fixed bed epoxidation reaction ​​

[0164] The catalyst layer was formed by filling the reactor having an inner diameter of 16 mm (a sheath outer diameter of 5 mm) with the catalyst shaped body obtained in the above-mentioned procedures (1) to (6) at 10 ml (apparent volume including the volume of the space between the shaped bodies). To the filled catalyst layer, a solution (hereinafter referred to as 31.5 mass% CMHP / CUM) obtained by dissolving CMHP in CUM at a concentration of 31.5 mass% and propylene were supplied, and synthesis of propylene oxide was performed by epoxidation reaction. The reaction conditions were as follows.

[0165] LHSV = 18 hours -1 、 Molar ratio of propylene / CMHP = 8, Reaction pressure = 6 MPa-G, The reactor was warmed by an electric furnace provided on the outside of the reactor so that the average temperature of the catalyst layer reached 120°C, Sampling was performed for 30 minutes from the third hour after the start of warming.

[0166] • Reaction results

[0167] The conversion rate of CMHP and the selectivity of PO and the selectivity of "PGs (polypropylene glycol-based)" were calculated in the following manner. The reaction results are shown in Table 2.

[0168] • CMHP conversion rate (%) = 100 x M1 / M2

[0169] M0: Molar amount of raw material CMHP

[0170] M1: Molar amount of CMHP in the liquid after reaction

[0171] M2: Molar amount of CMHP subjected to reaction

[0172] where M2 = M0- M1

[0173] • PO selectivity (%) = 100 x M PO / M2

[0174] M PO : Molar amount of generated PO

[0175] where M PO = M2- (M ph + M ac + M pg + 2 x M dpg + 3 x M tpg )

[0176] M ph : Molar amount of generated phenol

[0177] Mac : Mole amount of generated acetophenone

[0178] M pg : Mole amount of generated propylene glycol

[0179] M dpg : Mole amount of generated dipropylene glycol

[0180] M tpg : Mole amount of generated tripropylene glycol

[0181] PGs selectivity (%) = 100 x M PGs / M2

[0182] M PGs : Mole amount of generated PGs

[0183] wherein, M PGs = M pg + 2 x M dpg + 3 x M tpg

[0184] Example 2 and Comparative Examples 1 and 2

[0185] For Example 2 and Comparative Examples 1 and 2, the procedures, evaluation, and measurement in the above (1) to (9) except for (3) were carried out by the same method as in Example 1. As for the procedure of the above (3), except for changing the mixing ratio of the classified shaped bodies as described in Table 2, it was carried out by the same method as in Example 1.

[0186] Table 2

[0187] From the results described in Table 2, it is apparent that in Comparative Examples 1 to 3 (not satisfying at least one of the features "D50 of the catalyst: 1.00 mm to 3.30 mm" and "(D90-D10) / D50: 0.35 to 1.00" of the present application), the CMHP conversion rate is as low as 77% or less, the PO selectivity is also as low as 97% or less, and PO cannot be produced at a high yield. On the contrary, in Examples 1 to 4 (satisfying both of the features "D50 of the catalyst: 1.00 mm to 3.30 mm" and "(D90-D10) / D50: 0.35 to 1.00" of the present application), the CMHP conversion rate and the PO selectivity are significantly higher than in the comparative examples, and PO can be produced at a high yield.

[0188] Industrial applicability

[0189] The titanium-containing silicon oxide of the present application can be used as a catalyst for a method of producing an epoxide from an olefin and a hydroperoxide.

Claims

1. A titanium-containing silicon oxide, wherein, The titanium-containing silicon oxide satisfies all of the conditions 1 to 5, Condition 1: average pore size of 10 above; Condition 2: More than 80% of the total pore volume has a pore diameter of 5 ~ 200 A. Condition 3: Total pore volume is 0.2 cm3 / g 3 above; Condition 4: the D50 of the titanium-containing silicon oxide is 1.00 mm to 3.30 mm; and Condition 5: the (D90-D10) / D50 of the titanium-containing silicon oxide is 0.35 to 1.

00.

2. The titanium-containing silicon oxide of claim 1, wherein, The titanium-containing silicon oxide can be obtained by a method comprising: using a quaternary ammonium ion represented by Formula I as a template agent, and then removing the template agent by a solvent extraction operation, [NR 1 R 2 R 3 R 4 ] + I (In the formula, R) 1 Indicate C 2～36 hydrocarbon group, R 2 ~R 4 Each represents C independently. 1～6 (hydrocarbon group).

3. The titanium-containing silicon oxide according to claim 1 or 2, wherein, The titanium-containing silicon oxide is used for producing an epoxide from an olefin and a hydroperoxide.

4. The titanium-containing silicon oxide of claim 3, wherein, The olefin is propylene, and the hydroperoxide is cumene hydroperoxide.

5. A method for producing a titanium-containing silicon oxide, wherein, The method for producing the titanium-containing silicon oxide comprises the following steps: a raw material mixing step of obtaining a solid containing a silicon oxide and a template agent by mixing a silicon source, a template agent, and a solvent; a template agent removal step of obtaining a solid by removing the template agent from the solid obtained in the raw material mixing step; a silylation step of obtaining a solid containing a silylated silicon oxide by bringing the solid obtained in the template agent removal step into contact with a silylating agent; a titanium introduction step of introducing titanium into the solid at at least one timing selected from the group consisting of within the raw material mixing step, after the raw material mixing step and before the template agent removal step, within the template agent removal step, after the template agent removal step and before the silylation step, within the silylation step, and after the silylation step; a particle size distribution adjustment step of adjusting the particle size distribution of the solid supplied to the step so that the titanium-containing silicon oxide of the final product satisfies the following conditions at at least one timing selected from the group consisting of after the raw material mixing step, before the template agent removal step, within the template agent removal step, after the template agent removal step and before the silylation step, within the silylation step, and after the silylation step: D50 of the solid: 1.00 mm to 3.30 mm; and (D90-D10) / D10 of the solid: 0.35 to 1.

00.

6. The method of claim 5, wherein, The method comprises: a shaping step of shaping the solid obtained at at least one timing selected from the group consisting of after the raw material mixing step, after the template agent removal step, and after the silylation step, thereby obtaining a solid as a shaped body.

7. The method of claim 6, wherein, The solid obtained in the shaping step is subjected to a particle size distribution adjustment step.

8. The method of claim 7, wherein, The particle size distribution adjustment step comprises a classification treatment of the solid.

9. The method of claim 8, wherein, In the particle size distribution adjustment step, the classified solid is mixed.

10. A titanium-containing silicon oxide, wherein, The titanium-containing silicon oxide can be obtained by the method according to any one of claims 5 to 9.

11. Use of the titanium-containing silicon oxide according to any one of claims 1 to 4 and 10 for producing an epoxide from an olefin and a hydroperoxide.

12. Use according to claim 11, wherein, The olefin is propylene, and the hydroperoxide is cumene hydroperoxide.

13. A method of making an epoxide, wherein, The method comprises a step of reacting an olefin with a hydroperoxide in the presence of the titanium-containing silicon oxide according to any one of claims 1 to 4 and 10.

14. The method of claim 13, wherein, The olefin is propylene, and the hydroperoxide is cumene hydroperoxide.

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