Biochemical identification of a hydroperoxide derivative of. The first plant to produce phenol and acetone from petroleum, through oxidation of cumene, went into operation last week when b. The firstorder decomposition of hydrogen peroxide has a half. Chemicals listed effective april 2, 2010 as known to the state to cause cancer. Reactive hazard analysis of cumene hydroperoxide and. Production of phenol and acetone from oxidation of cumene. Chp solution in cumene oxidized at 453 k and 680 psi of oxygen reproducibly with the heat of reaction linearly dependent on peroxide concentration in cumene. An assay for the rate of removal of extracellular hydrogen. The company, owned jointly by shawinigan chemicals and british american oil co. Insights into the mechanism of cumene peroxidation using.
Microimpinger bottles and personal air sampling pumps were used for the sampling. Composition information on ingredients common name cumene hydroperoxide formula c 9 h 12 o 2 cas number 80159 component cas number concentration cumene hydroperoxide 80159 70 90% cumene 20 30% 2phenylpropan2ol 10 20% section 4. Expired lifetime application number us339446a inventor carleton t handy henry s rothrock. Required temperature c for one hour and ten hours halflife. Products of decomposition of cumene hydroperoxide are methylstyrene, acetophenone, and cumyl alcohol. Gas chromatographymass spectrometry was used for the analytical separation and quantitative determination. Polyisoprene ir, natural rubber nr, and styrenebutadiene rubber sbr have. List of organic peroxides purity theoretical aoc package volume storage temp.
The half life period of a first order reaction is 10 minutes. Polyester curatives peroximon curing agents for polyester resins include mek peroxides k1 and k10, methylisobutyl ketone peroxide k2, acetylacetone k3, and cumene hydroperoxide ch. The thermal decomposition and runaway reaction of cumene hydroperoxide chp in cumene were studied by thermal analysis and by using the vspii adiabatic calorimeter. Cumene hydroperoxide article about cumene hydroperoxide. Safety data sheet cumene hydroperoxide date prepared. Hydrogen peroxide, aqueous solutions with not less than 8% but less than 20% hydrogen peroxide d. Jul 18, 1978 the oxidants used in the examples included sulphur example 2, sulphuric acid example 3, air example 4, cumene hydroperoxide example 5, copper isophthalate example 6, silver isophthalate example 7, ditbutyl peroxide in the presence of isophthalic acid example 8 and benzoyl peroxide in the presence of isophthalic acid example 9. Dicumyl peroxide is a white powder with a characteristic odor. This page was last edited on 6 january 2019, at 10. Micron sized spherical droplets of metals and method. The addition of limiting amounts of cumene hydroperoxide to rat liver microsomes prepared from phenobarbitaltreated rats resulted in the rapid uptake of molecular oxygen, the formation of thiobarbituric acid reactive. This paper discusses the results of investigations on the kinetics of cumene oxidation to cumene hydroperoxide by molecular oxygen in the presence of n.
Explosion evaluation and safety storage analyses of cumene. I know that hydrogen peroxide undergoes spontaneous decomposition when dissolved in an acqueous solution. Trigonox 239c is a peroxide mixture based on promoted cumene hydroperoxide and tertbutyl peroxybenzoate. The halflife is the time re quired to reduce the original amount of peroxide at a given temperature by 50%. This article covers the thermal properties of cumene hydroperoxide chp and dicumyl hydroperoxide dcpo. The photochemical decomposition of dicumyl peroxide and cumene hydroperoxide in the absence of oxygen has been investigated in two solvents. Cumene hydroperoxide is a colorless to light yellow liquid with a sharp, irritating odor.
Peroxan cu50 cumene hydroperoxide 140, 284 50% solution in cumene 5. The reason may be that either its halflife span is too short, or its steadystate concentration is too low. In mammalian cells, it is excised by the 8oxoguanine dna glycosylases ogg1 during dna base excision repair, and the generated free 8oxog base 8oxog is one of the dnaderived biomarkers of oxidative stress in biological samples. Insoluble water, soluble ethanol, ether, acetic acid, benzene and petroleum ether. According to 1 hnmr spectroscopy, ditbutyl peroxide is the main product of the hypochlorite reaction with tbutyl hydroperoxide. Pdf catalytic decomposition of cumene hydroperoxide into. Reaction mechanisms have been suggested from a consideration of the products and the quantum yields. Its formula is c 6 h 5 cch 3 2 ooh one of the key uses for the material is as a free radical. In addition to the polymers shown, cispolybutadiene br has a halflife curve between those of nitrile rubber nbr and ethylene. Isopropylbenzene hydroperoxide, 1methyl1phenylethylhydroperoxide, 2phenyl2propyl hydroperoxide cumene hydroperoxide is a reagent that is used to produce organic peroxides. Kinetics of catalystfree thermal and photooxidation of. Determination of dicumyl peroxide in workplace air annals.
Oxidations of alkylbenzene benzene derivatives conjugated. The industrial applications include the production of polymers and fiberglass products. The decomposition of aqueous hydrogen peroxide to gaseous o2. The hydroperoxide of isopropyl benzene cumene obtained by the oxidation of isopropyl benzene. Global cumene market analysis and forecast, 20142022. Us2706708a process for separating cumene from cumene. May react explosively upon contact with reducing reagents. There is a wide range of capacity of cells to remove extracellular h 2 o 2. Cumene hydroperoxide technical grade, 80% sigmaaldrich. This new determination of the reaction order as equal to one half implies the same mechanism of decomposition regardless of chp concentration. It is prepared from the oxidation of cumene with air at a high temperature. Tertbutyl hydroperoxide is an alkyl hydroperoxide in which the alkyl group is tertbutyl. The mechanism of cumene hydroperoxide dependent lipid peroxidation.
Violent reaction occurs upon contact with copper, copper alloys, lead alloys, and mineral acids. The halflife temperatures are 61 c for 10 hours, 80 c 1 for 1. Heat of decomposition and initial exothermic temperature of cumene hydroperoxide. It was confirmed that cumene thermal oxidation was slow at peroxide is a strong free radical source. Luperox cu80 polymer initiator is used for curing of highly reactive polyester or acrylic resins for lower exotherm and slower cure times. Red blood cells have a high capacity to remove extracellular h 2 o 2, despite their small size. Cumene hydroperoxide wiki 1methyl1phenylet hyl hydroperoxide. If you submit this form, please be aware that your name and email may be provided to third parties. Files are available under licenses specified on their description page. In general, high concentration of chp for thermal analysis using the calorimeter is dangerous. The specific strategy proposed for the introduction of lipophilic tails on the nhpi moiety leads to lipophilic catalysts thatwhile completely preserving the activity of the precursorallow the catalytic oxidation to be. This oxidizing agent is commercially available with a purity of 80%. The cumene process cumene phenol process, hock process is an industrial process for synthesizing phenol and acetone from benzene and propylene.
A thermal activity monitor tam was also used to detect the storage index and thermal hazard parameters. Kinetics and mechanism of cumene oxidation initiated by n. The mechanism of cumene hydroperoxidedependent lipid. Aug 21, 2015 the calculated halflife of 1200 mgl1 h2o2 was inconsistent with the preliminary calculated halflife 14 days versus 28 days. It has a role as an antibacterial agent and an oxidising agent. Highstrength hydrogen peroxide, hydrogen dioxide, hydrogen peroxide aqueous, hydroperoxide, peroxide. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.
Hydrogen peroxide h2 o 2 is a nonplanar molecule with twisted c 2 symmetry. The photochemical decomposition of dicumyl peroxide and. Thermal decomposition kinetics of cumene hydroperoxide article pdf available in process safety and environmental protection 764. Cumene hydroperoxide chp is manufactured by cumene mixed with oxygen or air in the oxidation tower and is an important chemical and hazardous material for dicumyl peroxide dcpo manufacturing. Jul 24, 2012 plenty of thermal explosions and runaway reactions of cumene hydroperoxide chp were described from 1981 to 2010 in taiwan. Feb 15, 2012 8oxo7,8dihydroguanine is one the most abundant base lesions in pro and eukaryotic dna. Oehha is subject to the california public records act and other laws that require the release of certain information upon request. Us4564663a us06703,633 us70363385a us4564663a us 4564663 a us4564663 a us 4564663a us 70363385 a us70363385 a us 70363385a us 4564663 a us4564663 a us 4564663a authority us united states. Cdc niosh pocket guide to chemical hazards hydrogen peroxide.
It is widely used in a variety of oxidation processes. A method for the determination of dicumyl peroxide in workplace air was developed and applied. The cumene process for phenolacetone production pdf. The material, as it is purchased, is often listed as 80% cumene hydroperoxide. The halflife temperatures are 61 c for 10 hours, 80 c 1 for 1 hour and 120 c for 1 minute.
Figure 1 is a plot of the crosslinking halflife of dicup dicumyl peroxide in various systems. Reaction mechanism of cumene hydroperoxide decomposition in cumene and evaluation of its reactivity hazards. Cumene hydroperoxide is an organic hydroperoxide intermediate in the cumene process for synthesizing phenol and acetone from benzene and propene. Thermal decomposition kinetics of cumene hydroperoxide core. The term stems from cumene isopropyl benzene, the intermediate material during the process. This work is based on the study of cumene or isopropylbenzene ipb oxidation to cumene hydroperoxide chp, the key reaction of the phenol production industrial process currently in use worldwide 1. Notice of intent to list bromochloroacetic acid and cumene. Us2706708a us390626a us39062653a us2706708a us 2706708 a us2706708 a us 2706708a us 390626 a us390626 a us 390626a us 39062653 a us39062653 a us 39062653a us 2706708 a us2706708 a us 2706708a authority us united states prior art keywords hydroperoxide steam dialkylarylmethane cumene zone prior art date 19531106 legal status the legal status is an. Us4564663a free radical cure of the bismaleimide of dimer. Trigonox 239c promoted mixture of cumyl hydroperoxide and. Cumene hydroperoxide 60 peroxide in various systems. Cumene hydroperoxide c9h12o2 cid 6629 structure, chemical names, physical and chemical properties. Pdf thermal decomposition kinetics of cumene hydroperoxide.
Catalytic decomposition of cumene hydroperoxide into phenol and acetone article pdf available in applied catalysis a general 2191. Synthesis of cumene hydroperoxide compounds with allylic and benzylic c. This process converts two relatively cheap starting. Peroxide initiators include mekp and other ketone peroxides, tbutyl perbenzoate, tbutyl hydroperoxide, cumene hydroperoxide, dicumyl peroxide, and bpo paste. H2so4, it undergo rearrangement to produce phenol and acetone, where cumene hydroperoxide is prepared by treating cumene, i. Request for relevant information on chemicals being considered for listing by the authoritative bodies mechanism. Jan 14, 1986 in all cases, the time to gel formation is greater than 1. All structured data from the file and property namespaces is available under the creative commons cc0 license. The halflife is the time required to reduce the original amount of peroxide at a given temperature by 50%. Therefore, a thermal explosion accident of chp in oxidation tower in 2010 in taiwan was investigated because of piping breakage. A peroxol that is cumene in which the alpha hydrogen is replaced by a hydroperoxy group. The decomposition products of cumene hydroperoxide are methylstyrene, acetophenone, and cumyl alcohol. Does anyone know the rate of disappearance of h2o2 in an.
Highlights we present a method to determine a rate constant, k cell, for removal of extracellular h 2 o 2 by cells. Organic peroxides product guide organische peroxide. The pure compound is a crystalline solid below 12f. A mathematical model has been developed on the basis of the regularities of hydroperoxide and by. Trigonox 239c is especially developed to improve the cure efficiency of vinylester resins in combination with a cobalt accelerator at elevated temperatures. In addition to the polymers shown, cispolybutadiene br has a halflife curve between those of nitrile rubber nbr and ethylenepropylene terpolymer epdm. It has a role as an oxidising agent, an environmental contaminant and a mycoplasma genitalium metabolite. To further assist you in your selection of a thermal initiator, the temperature corresponding to a 10 hour halflife in a specific solvent is also shown. Free radical cure of the bismaleimide of dimer diamine the.
The weaker the ch bond, the higher the rate constant. According to some literature i found, h2o2 would have a halflife of 510 hrs. Applications dcp, as an excellent organic peroxide, is mainly used as the crosslinking agents of pe, eva resins. Decomposition kinetics were determined in various chp concentrations in cumene. Jul 04, 2010 the decomposition of aqueous hydrogen peroxide to gaseous o2 and water is a firstorder reaction. O bond is a single bond, the molecule has a relatively high rotational barrier of 2460 cm. Thermal decomposition kinetics of cumene hydroperoxide. For each test, a clean sodium borosilicate glass cell was fitted with a septum, purged with nitrogen, and placed in a nitrogenpurged glove box containing the appropriate cumene hydroperoxide and other hydrocarbon samples. Cumene hydroperoxide is a peroxol that is cumene in which the alphahydrogen is replaced by a hydroperoxy group. Structure, properties, spectra, suppliers and links for. The slopes for the cumene hydro peroxide system and linoleic acid hydro peroxide system are 4. The cumene process for phenolacetone pa manufacture is one of the unique highvolume petrochemical processes in which simultaneously two products phenol and acetone are obtained from one reactant cumene, each of the products finding useful application.
Regulation of organic hydroperoxide stress response by two. Cumyl peroxide reacts with cumene with the rate constant k 24 510 7 exp. Cumene in chemical form is known as isopropyl benzene, an organic compound based on aromatic hydrocarbons with aliphatic substitution. Kinetics of acidcatalyzed cleavage of cumene hydroperoxide. The influence of biotic communities and organic matter on the degradation of h2o2 in the interox paramove50 formulation was investigated using filtered 0. H d, exothermic onset temperature t 0, reaction order n, etc. Cumene hydroperoxide how is cumene hydroperoxide abbreviated. Cumene hydroperoxide is a colorless to pale yellow liquid chemical used as a polymerization inhibitor particularly in redox systems and to manufacture organic peroxides, primarily dicumylperoxide, which are used in the manufacture of plastic resins and as initiators in chemical reactions. Reactive hazard analysis of cumene hydroperoxide and dicumyl. Cumene hydroperoxide 60 halflife of dicup dicumyl peroxide in various systems. Nov 22, 2007 the firstorder decomposition of hydrogen peroxide has a halflife of 10.
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