Cyclohexanone Peroxide

By far the most popular commercial ketone peroxide is methyl ethyl ketone peroxide [1338-23-4]. Smaller quantities of ketone peroxides such as methyl isobutyl ketone peroxide [28056-59-9] cyclohexanone peroxide [12262-58-7] and 2,4-pentanedione peroxide [37187-22-7] are used commercially (47). 

G-20 Dicarboxylic Acids. These acids have been prepared from cyclohexanone via conversion to cyclohexanone peroxide foUowed by decomposition by ferrous ions in the presence of butadiene (84—87). Okamura Oil Mill (Japan) produces a series of commercial acids based on a modification of this reaction. For example, Okamura s modifications of the reaction results in the foUowing composition of the reaction product C-16 (Linear) 4—9%, C-16 (branched) 2—4%, C-20 (linear) 35—52%, and C-20 (branched) 30—40%. Unsaturated methyl esters are first formed that are hydrogenated and then hydrolyzed to obtain the mixed acids. Relatively pure fractions of C-16 and C-20, both linear and branched, are obtained after... 

More frequently either methyl ethyl ketone peroxide or cyclohexanone peroxide is used for room temperature curing in conjunction with a cobalt compound such as a naphthenate, octoate or other organic solvent-soluble soap. The peroxides (strictly speaking polymerisation initiators) are referred to as catalysts and the cobalt compound as an accelerator . Other curing systems have been devised but are seldom used. 

Cyclohexanone peroxide, a white powder, another mixture of peroxidic materials, has a similar reactivity to MEKP. Usually supplied as a 50% paste in dimethyl or dibutyl phthalate, it has to be weighed out, but it is easier to follow dispersion and to observe spillage. The quantity of peroxide used is generally 0.5-3% of the polyester. 

Dimethyl peroxide Diethyl peroxide Di-t-butyl-di-peroxyphthalate Difuroyl peroxide Dibenzoyl peroxide Dimeric ethylidene peroxide Dimeric acetone peroxide Dimeric cyclohexanone peroxide Diozonide of phorone Dimethyl ketone peroxide Ethyl hydroperoxide Ethylene ozonide Hydroxymethyl methyl peroxide Hydroxymethyl hydroperoxide... 

For a number of applications curing at room temperature is desirable. This so-called cold cure is brought about by using a peroxy initiator in conjunction with some kind of activator substance. The peroxy compounds in these cases are substances such as methyl ethyl ketone peroxide and cyclohexanone peroxide, which as used in commercial systems tend not to be particularly pure, but instead are usually mixtures of peroxides and hydroperoxides corresponding in composition approximately to that of the respective nominal compounds. Activators are generally salts of metals capable of undergoing oxidation/reduction reactions very readily. A typical salt for this purpose is cobalt naphthenate, which undergoes the kind of reactions illustrated in Reactions 4.6 and 4.7. 

Dimethyl peroxide Diethyl peroxide Di-t-butyl-di-peroxyphthalate Difuroyl peroxide Dibenzoyl peroxide Dimeric ethylidene peroxide Dimeric acetone peroxide Dimeric cyclohexanone peroxide Diozonide of phorone Dimethyl ketone peroxide Ethyl hydroperoxide Ethylene ozonide Hydroxymethyl methyl peroxide Hydroxymethyl hydroperoxide 1-Hydroxyethyl ethyl peroxide 1 -Hydroperoxy-1 -acetoxycyclodecan-6-one Isopropyl percarbonate Isopropyl hydroperoxide Methyl ethyl ketone peroxide Methyl hydroperoxide Methyl ethyl peroxide Monoperoxy succinic acid Nonanoyl peroxide (75% hydrocarbon solution) 1-Naphthoyl peroxide Oxalic acid ester of t-butyl hydroperoxide Ozonide of maleic anhydride Phenylhydrazone hydroperoxide Polymeric butadiene peroxide Polymeric isoprene peroxide Polymeric dimethylbutadiene peroxide Polymeric peroxides of methacrylic acid esters and styrene... 

Dilthey, W. et al., J. Prakt. Chem., 1940, 154, 219 This dimeric cyclohexanone peroxide explodes on impact. 

This appears to be a main constituent of commercial cyclohexanone peroxide together with the bis(hydroperoxy) peroxide (below), and is also known to be hazardous [1], Prepared from cyclohexanone and 30% hydrogen peroxide in presence of hydrochloric acid catalyst, it must be kept moist after isolation as it may explode on drying out [2],... 

One of the components in cyclohexanone peroxide , it explodes violently at elevated temperatures (dining vacuum distillation or on exposure to flame). 

Cyclohexanone peroxide [78-18-2] (dimer 53) E. Peracids and derivatives 1. Free acids UN2896. f... 

Compound Name Cadmium Nitrate Cadmium Oxide Cadmium Sulfate Cyclohexanone Peroxide DI-(p-Chlorobenzoyl) Peroxide Tert-Butyl Hydroperoxide Aluminum Sulfate Calcium Phosphate Calcium Resinate... 

Dimeric Cyclohexanone Peroxide. See Comp VI, under Cyclohexanone Peroxide in Vol 3, p C598-R... 

Ketone peroxides Methyl ethyl ketone peroxide Cyclohexanone peroxide... 

Dimeric cyclohexanone peroxide see Cyclohexanone peroxide 3 CS98... 

C-20 Dicarboxylic Acids. These acids have been prepared front cyclohexanone via conversion to cyclohexanone peroxide followed by decomposition by ferrous ions in Ihe presence of butadiene, Okamura Oil Mill (Japan) produces a series of commercial acids based on a modification of this reaction. 

Cyclohexanone Peroxide. The compn of peroxides obtd from the interaction of cyclohexanone other cyclic ketones with hydrogen peroxides has been a controversial matter. Milas (Ref 3) claimed to have obtd from an ethereal soln of H202 cyclohexanone ... 

Ketone Peroxides. These materials are mixtures of compounds with hydroperoxy groups and are composed primarily of the two structures shown in Table 2. Ketone peroxides are marketed as solutions in inert solvents such as dimethyl phthalate. They are primarily employed in room-temperature-initiated curing of unsaturated polyester resin compositions (usually containing styrene monomer) using transition-metal promoters such as cobalt naphthenate. Ketone peroxides contain the hydroperoxy (—OOH) group and thus are susceptible to the same hazards as hydroperoxides. By far the most popular commercial ketone peroxide is methyl ethyl ketone peroxide [1338-23-4]. Smaller quantities of ketone peroxides such as methyl isobutyl ketone peroxide [28056-59-9], cyclohexanone peroxide [12262-58-7], and 2,4-pentanedione peroxide [37187-22-7] are used commercially (47). 

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