18428-18-7

Upstream product

• 1565-75-9 2-phenyl-2-butanol 
• 135-98-8 sec-Butylbenzene 
• 98-82-8 Isopropylbenzene 
• 75-91-2 tert.-butylhydroperoxide 
• 1038-30-8 Mono(alpha-ethyl-alpha-methylbenzyl)phthalate 

Downstream Products

• 102560-29-2 (1-methyl-1-phenyl-propyl)-xanthen-9-yl peroxide 
• 1565-75-9 2-phenyl-2-butanol 
• 98-86-2 acetophenone 
• 78-93-3 butanone 
• 108-95-2 phenol 
• 135-98-8 sec-Butylbenzene 
• 101584-32-1 phenyl-carbamic acid-(1-methyl-1-phenyl-propyl ester) 
• 53777-08-5 (S)-2-phenyl-butan-2-ol 
• 1006-06-0 (R)-2-phenyl-butan-2-ol 
• 139470-91-0 (R)-1-methyl-1-phenyl-propyl hydroperoxide 

Relevant academic research and scientific papers

Kinetic resolution of 1-methyl-1-phenylpropyl hydroperoxide via sharpless epoxidation

The kinetic resolution of 1-methyl-1-phenylpropyl hydroperoxide via catalytic Sharpless epoxidation with various allylic alcohols has been investigated. An enantiomeric excess of nearly 20% of the resolved hydroperoxide has been observed.

Oxidizing properties of the tert-butyl hydroperoxide-tetra-tert- butoxychromium system

tert-Butyl hydroperoxide reacts with the tetra-tert-butoxychromium by oxidizing the latter to chromyl CrV=O (C6H6, 20 C). At t-BuOOH-Cr(OBu-t)4 ratio of 2: 1 or higher, oxygen is released. The occuring processes include the formation of chromium-containing peroxides and peroxytrioxydes. The t-BuOOH-Cr(OBu-t)4 system oxidizes aromatic hydrocarbons of various structures (anthracene, 9,10-dimethylanthracene, 1,1-diphenylethylene, alkylarenes), as well as primary and secondary alcohols. Depending on the structure of the substrate, the oxidants are: in situ generated oxygen including that in the singlet state, peroxy radicals, or chromium-containing peroxides.

Process for Producing Alkylbenzene Hydroperoxides

In a process for producing alkylbenzene hydroperoxides, a feed comprising (i) sec-butylbenzene, (ii) cumene in an amount greater than 10 wt % of the total feed and (iii) at least one of iso-butylbenzene and tert-butylbenzene in an amount up to 20 wt % of the total feed is contacted with an oxygen-containing gas in the presence of a catalyst comprising a cyclic imide of the general formula (I): wherein each of R1 and R2 is independently selected from hydrocarbyl and substituted hydrocarbyl radicals having 1 to 20 carbon atoms, or from the groups SO3H, NH2, OH, and NO2 or from the atoms H, F, Cl, Br, and I, provided that R1 and R2 can be linked to one another via a covalent bond; each of Q1 and Q2 is independently selected from C, CH, N and CR3; each of X and Z is independently selected from C, S, CH2, N, P and elements of Group 4 of the Periodic Table; Y is O or OH; k is 0, 1, or 2; l is 0, 1, or 2; m is 1 to 3; and R3 can be any of the entities listed for R1. The contacting is conducted under conditions to convert the sec-butylbenzene and cumene to their associated hydroperoxides.

PROCESS FOR PRODUCING PHENOL

Disclosed is a process for producing phenol or a substituted phenol and a co-product comprising the steps of (i) contacting a first stream comprising an alkylaromatic compound with a second stream comprising an oxygen-containing gas in the presence of a first catalyst comprising a cyclic imide under conditions to convert at least a portion of said alkylaromatic compound to an alkylaromatic hydroperoxide, (ii) producing an effluent stream comprising said cyclic imide, said alkylaromatic hydroperoxide, and said alkylaromatic compound wherein said effluent stream has an alkylaromatic hydroperoxide concentration of from 10 to 40 wt%; and (iii) contacting in a second reactor at least a portion of said effluent stream with a second catalyst to convert said alkylaromatic hydroperoxide to a product stream comprising phenol and said co-product.

PROCESS FOR PRODUCING PHENOL

In a process for producing phenol or a substituted phenol, an alkylaromatic hydroperoxide having a general formula (I): R1 / (I) I2C R2 in which R1 and R2 each independently represents an alkyl group having from 1 to 4 carbon atoms, provided that R1 and R2 may be joined to form a cyclic group having from 4 to 10 carbon atoms, said cyclic group being optionally substituted, and R3 represents hydrogen, one or more alkyl groups having from 1 to 4 carbon atoms or a cyclohexyl group, is contacted with a catalyst comprising an oxide of at least one metal from Groups 3 to 5 and Groups 7 to 14 of the Periodic Table of the Elements and an oxide of at least one metal from Group 6 of the Periodic Table of the Elements.

OXIDATION OF ALKYLAROMATIC COMPOUNDS

In a process for oxidizing an alkylaromatic compound to the corresponding hydroperoxide, a feed comprising an alkylaromatic compound is contacted with an oxygen-containing gas in the presence of a catalyst comprising a cyclic imide. The contacting is cond

Catalytic activity of iron-substituted polyoxotungstates in the oxidation of aromatic compounds with hydrogen peroxide

The tetrabutylammonium (TBA) salts of Keggin-type polyoxotungstates of the general formula [XW11FeIII(H2O)O39] n-, where X = P, B or Si, were evaluated as catalysts in the oxidation, under mild conditions, of ethylbenzene, cumene, p-cymene and sec-butylbenzene with aqueous H2O2 in CH3CN at 80 °C. The influence of various factors, such as the substrate/catalyst molar ratio, the amount of oxidant added or the reaction time, was investigated in a systematic way. Generally, the system exhibited moderate conversion, with good selectivity towards the corresponding acetophenone and hydroperoxide. In order to understand the reaction pathways, the oxidation of several products and presumed intermediates was also carried out in the presence of TBA 4[PW11Fe(H2O)O39]?2H 2O. Under the conditions used, the oxidation of styrene and styrene derivatives gave rise mainly to carbon-carbon double-bond cleavage, affording the corresponding products in very high yields (81-87%). Possible reaction pathways are presented.

OXIDATION OF HYDROCARBONS

In a process for oxidizing a hydrocarbon to the corresponding hydroperoxide, alcohol, ketone, carboxylic acid or dicarboxylic acid, a reaction medium comprising a hydrocarbon is contacted with an oxygen-containing gas in the presence of a catalyst comprising a cyclic imide of the general formula (I): wherein each of R1 and R2 is independently selected from hydrocarbyl and substituted hydrocarbyl radicals having 1 to 20 carbon atoms, or from the groups SO3H, NH2, OH and NO2, or from the atoms H, F, Cl, Br and I provided that R1 and R2 can be linked to one another via a covalent bond; each of Q1 and Q2 is independently selected from C, CH, N, and CR3; each of X and Z is independently selected from C, S, CH2, N, P and an element of Group 4 of the Periodic Table; Y is O or OH; k is O, 1, or 2; 1 is 0, 1, or 2; m is 1 to 3; and R3 can be any of the entities listed for R1. The contacting is conducted under conditions such as to maintain the concentration of both water and organic acids in the reaction medium below 50 ppm.

OXIDATION OF HYDROCARBONS

In a process for oxidizing a hydrocarbon to a corresponding hydroperoxide, alcohol, ketone, carboxylic acid or dicarboxylic acid, the hydrocarbon is contacted with an oxygen- containing gas in the presence of a catalyst comprising a cyclic imide of the general formula (I); wherein each of R1 and R2 is independently selected from hydrocarbyl and substituted hydrocarbyl radicals having 1 to 20 carbon atoms, or from the groups SO3H, NH2, OH and NO2, or from the atoms H, F, Cl, Br and I provided that R1 and R2 can be linked to one another via a covalent bond; each of Q1 and Q2 is independently selected from C, CH, N and CR3; each of X and Z is independently selected from C, S, CH2, N, P and elements of Group 4 of the Periodic Table; Y is O or OH; k is O, 1, or 2; 1 is 0, 1, or 2; m is 1 to 3, and R3 can be any of the entities listed for R1. The contacting produces an effluent comprising an oxidized hydrocarbon product and unreacted imide catalyst of said formula (I) and the effluent is treated with a solid sorbent to remove at least part of the unreacted imide catalyst and produce a treated effluent comprising said oxidized hydrocarbon product. The organic phase can then be recovered.

PROCESS FOR OXIDIZING ALKYLAROMATIC COMPOUNDS

In a process for producing hydroperoxides, an alkylaromatic compound of general formula (I) in which R1 and R2 each independently represents an alkyl group having from 1 to 4 carbon atoms, provided that R1 and R2 may be joined to form a cyclic group having from 4 to 10 carbon atoms, said cyclic group being optionally substituted, and R3 represents hydrogen, one or more alkyl groups having from 1 to 4 carbon atoms or a cyclohexyl group, with oxygen in the presence of a catalyst comprising a manganese oxide molecular sieve to produce a hydroperoxide of general formula (II) in which R1, R2 and R3 have the same meaning as in formula (I). The hydroperoxide of formula (II) may then be converted to a phenol and an aldehyde or a ketone of the general formula R1COCH2R2 (III), in which R1 and R2 have the same meaning as in formula (1). In the case where the ketone is cyclohexanone, this may then be dehydrogenated to produce further phenol.