Diisopropyl peroxydicarbonate

Diisopropyl peroxydicarbonate is a moderate skin irritant. The irritation can be severe on rabbit skin. Eye contact can cause conjunctivitis and corneal ulcerations, which, however, are fully recoverable in 1-2 weeks. Its toxicity is very low. There is no report of its ill effect on humans. It may cause dermatitis on sensitive skin. 

No exposure limit is set. Because of low toxicity and vapor pressure, the health hazard from its exposure does not arise. 

This compound is a highly reactive oxidizing and combustible substance. It explodes on heating. It can also decompose violently on its own below room temperature, the 

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Suspension polymerization of VDE in water are batch processes in autoclaves designed to limit scale formation (91). Most systems operate from 30 to 100°C and are initiated with monomer-soluble organic free-radical initiators such as diisopropyl peroxydicarbonate (92—96), tert-huty peroxypivalate (97), or / fZ-amyl peroxypivalate (98). Usually water-soluble polymers, eg, cellulose derivatives or poly(vinyl alcohol), are used as suspending agents to reduce coalescence of polymer particles. Organic solvents that may act as a reaction accelerator or chain-transfer agent are often employed. The reactor product is a slurry of suspended polymer particles, usually spheres of 30—100 pm in diameter they are separated from the water phase thoroughly washed and dried. Size and internal stmcture of beads, ie, porosity, and dispersant residues affect how the resin performs in appHcations. 

Chloroformates are versatile, synthetic intermediates, based on the affinity of the chlorine atoms for active hydrogen atoms. Chloroformates should be considered as intermediates for syntheses of pesticides, perfumes, dmgs, polymers, dyes, and other chemicals. Some of these products, eg, carbonates, are used as solvents, plastici2ers, or as intermediates for further synthesis. A significant use of chloroformates is for conversion to peroxydicarbonates, which serve as free-radical initiators for the polymeri2ation of vinyl chloride, ethylene, and other unsaturated monomers. The most widely used percarbonate initiators are diisopropyl peroxydicarbonate (IPP), di-2-ethyIhexylperoxydicarbonate (2-EHP), and di-j -butylperoxydicarbonate (SBP). The following Hst includes most of the commercially used percarbonates. 

Chemical Designations - Synonyms Diisopropyl percarbonate Diisopropyl peroxydicarbonate Isopropyl peroxydicarbonate Peroxydicarbonic acid, bis (1-methylethyl) ester Peroxydicarbonic acid, diisopropyl ester Chemical Formula C3H7OOCOOCOOC3H7. 

The cyclization of imines 7, induced by the isopropyloxycarbonyloxy radical (i-PrOC02). obtained by homolytic cleavage of diisopropyl peroxydicarbonate, leads to dibenz[6,/][l,4]-oxazepines 8, accompanied by traces of biphenyls and benzoxazoles.424... 

A mixture of the imine 7 (1 mmol), diisopropyl peroxydicarbonate (2 or 4 mmol) and benzene (20 mL) was kept at 60 C until TLC indicated that the reaction was complete. The solvent was removed under reduced pressure and the residue was analyzed by GC/MS. 

Dialkyl peroxydicarbonates have been reported as low temperature sources of alkoxy radicals (Scheme 3.30)lfMJfb and these radicals may be formed in relatively inert media. However, it is established, for primary and secondary peroxydicarbonates, that the rate of loss of carbon dioxide is slow compared to the rate of addition to most monomers or reaction with other substrates.186,187 Thus, in polymerizations carried out with diisopropyl peroxydicarbonate (47), chains will be initiated by isopropoxycarbonyloxy (48) rather than isopropoxy radicals (49) (see 3.4.2.2).188... 

Crano191 has investigated the reaction between diisopropyl peroxydicarbonate and tertiary amines. These experiments indicate the formation of radicals by loss of a hydrogen from the a-CH2 of the amine. It seems likely that the mechanism of... 

Diisopropyl peroxydicarbonate, 3034 1 -Hydropcroxy-1 -hydroxydicyclohexyl peroxide, 3555 2-Pheny 1-2-propyl hydroperoxide, 1387... 

Bis(fluoroformyl) peroxide, 0625 Bis-3-(2-furyl)acryloyl peroxide, 3640 Bis(trichloroacetyl) peroxide, 1361 Bis(trifluoroacetyl) peroxide, 1367 Diacetyl peroxide, 1537 Dibenzenesulfonyl peroxide, 3499 Dibenzoyl peroxide, 3639 Di-3-camphoroyl peroxide, 3807 Dicrotonoyl peroxide, 2986 Dicyclohexylcarbonyl peroxide, 3667 Didodecanoyl peroxide, 3857 Di-2-furoyl peroxide, 3245 Dihexanoyl peroxide, 3554 Diisobutyryl peroxide, 3032 Diisopropyl peroxydicarbonate, 3034 Dimethanesulfonyl peroxide, 0931 Di-2-methylbutyryl peroxide, 3354 Di-l-naphthoyl peroxide, 3831 3,6-Dioxo-l,2-dioxane, 1445 Dipropionyl peroxide, 2442 Dipropyl peroxydicarbonate, 3035 Di-4-toluenesulfonyl peroxide, 3656 Peroxodisulfuryl difluoride, 4328 Phthaloyl peroxide, 2900 Potassium benzenesulfonylperoxosulfate, 2257 Potassium O-O-benzoylmonoperoxosulfate, 2684 (9-TriIIuoroacctyl-.S -lluorofonny 1 thioperoxide, 1050 See PEROXIDES, PEROXYCARBONATE ESTERS... 

I. J-Diisocyanatotoluene Diisodecyl Phtbalate Diisopropanolamine Diisopropyl Ether Diisopropyl Oxide Diisopropyl Percarbonate Diisopropyl Peroxydicarbonate Sym-Diisopropylacetone Diisopropylamine... 

Near-quantitative yields of aryl isopropyl carbonates were realized in a similar process when diisopropyl peroxydicarbonate was reacted with alkyl-substituted aromatics.794 Substitution is effected by a radical entity possessing a considerable ionic character. 

The reaction of thiophene and its derivatives with diisopropyl peroxydicarbonate has been investigated (74JOC504). In the presence of CuCl2 as oxidant, 2-thienyl isopropyl carbonate is formed in 70% yield (Scheme 62). In the absence of added oxidant, loss of a hydrogen atom from the a-complex radical is less efficient. 

O-tert-Butyl hydrogen monoperoxymaleate, 3010 Diisopropyl peroxydicarbonate, 3029... 

Acetyl cyclohexanesulfonyl peroxide, 3028 2,2 -Biphenyldicarbonyl peroxide, 3624 Bis(2,4-dichlorobenzoyl) peroxide, 3617 Bis(2-azidobenzoyl) peroxide, 3621 Bis(3,4-dichlorobenzenesulfonyl) peroxide, 3439 Bis-3-(2-furyl)acryloyl peroxide, 3633 Bis(3-carboxypropionyl) peroxide, 2985 Bis(4-chlorobenzenesulfonyl) peroxide, 3452 Bis(bromobenzenesulfonyl) peroxide, 3447 Bis(fluoroformyl) peroxide, 0621 Bis(trichloroacetyl) peroxide, 1357 Bis(trifluoroacetyl) peroxide, 1363 Di-1-naphthoyl peroxide, 3825 Di-2-furoyl peroxide, 3239 Di-2-methylbutyryl peroxide, 3348 Di-3-camphoroyl peroxide, 3801 Di-4-toluenesulfonyl peroxide, 3649 Diacetyl peroxide, 1532 Dibenzenesulfonyl peroxide, 3493 Dibenzoyl peroxide, 3632 Dicrotonoyl peroxide, 2981 Dicyclohexylcarbonyl peroxide, 3660 Didodecanoyl peroxide, 3851 Dihexanoyl peroxide, 3548 Diisobutyryl peroxide, 3027 Diisopropyl peroxydicarbonate, 3029 Dimethanesulfonyl peroxide, 0927 3,6-Dioxo-l,2-dioxane, 1441... 

Table 7. Radical telomerisation of TFE (DBP, DIPC,BEPH,DTBPandF113 represent dibenzoyl peroxide, diisopropyl peroxydicarbonate, butyl ethyl peroxyhexanoate, ditertiarybutyl peroxide and C1CF2CFC12, respectively) ...

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