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142.3 Hydrogen Peroxide BPPC (Extrap) 150.2 Vapour Pressure(25")/Mmhg 1.9 Hydrogen Peroxide Was First Made in 1818 Density (Solid at -4So)/G Cm-3 1.6434 by J

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142.3 Hydrogen Peroxide BPPC (Extrap) 150.2 Vapour Pressure(25 Previous Page 814.2.3 Hydrogen peroxide 633 which traces the course of this controversy and Table 14.11 Some physical properties of hydrogen analyses the reasons why it took so long to peroxide(a) resolve.("') Property Value MPPC -0.41 142.3 Hydrogen peroxide BPPC (extrap) 150.2 Vapour pressure(25")/mmHg 1.9 Hydrogen peroxide was first made in 1818 Density (solid at -4So)/g cm-3 1.6434 by J. L. Thenard who acidified barium peroxide Density (liquid at 25")/g~rn-~ 1.#25 (p. 121) and then removed excess H2O by Viscosity(2O")/centipoise 1.245 evaporation under reduced pressure. Later Dielectric constant ~(25") 70.7 Electric condu~tivity(25")/S2~'cm-' 5.1 x lo-* the compound was prepared by hydrolysis AhHikl mol-' -187.6 of peroxodisulfates obtained by electrolytic AG;l/kJ mol-' -118.0 oxidation of acidified sulfate solutions at high current densities: fa)For D202: mp+ 1.5"; d20 1.5348g~rn-~;720 1.358 centipoise. -2e- 2HS04-( aq) --+HO3 SOOS03H( aq) 2H20 ---+ 2HS04- + H202 shown in Fig. 14.16a. This is due to repulsive interaction of the O-H bonds with the lone-pairs Such processes are now no longer used except in of electrons on each 0 atom. Indeed, H202 is the laboratory preparation of D202, e.g.: the smallest molecule known to show hindered K2S208 + 2D20 ---+ 2KDs04 + D202 rotation about a single bond, the rotational barriers being 4.62 and 29.45kJmol-' for the On an industrial scale H202 is now almost trans and cis conformations respectively. The exclusively prepared by the autoxidation of 2- skew form persists in the liquid phase, no doubt alkylanthraquinols (see Panel on next page). modified by H bonding, and in the crystalline state at - 163°C a neutron diffraction study" 12) Physical properties gives the dimensions shown in Fig. 14.16b. The dihedral angle is particularly sensitive to Hydrogen peroxide, when pure, is an almost H bonding, decreasing from 111.5" in the gas colourless (very pale blue) liquid, less volatile phase to 90.2" in crystalline H202; in fact, values than water and somewhat more dense and vis- spanning the complete range from 90" to 180" cous. Its more important physical properties are (Le. trans planar) are known for various solid in Table 14.11 (cf. H20, p. 623). The compound phases containing molecular H202 (Table 14.12). is miscible with water in all proportions and The 0-0 distance in H202 corresponds to the forms a hydrate H202.H20, mp -52". Addition value expected for a single bond (p. 616). of water increases the already high dielectric con- stant of H202 (70.7) to a maximum value of 121 at -35% H202, i.e. substantially higher than the Chemical properties value of water itself (78.4 at 25"). In the gas phase the molecule adopts a skew In H202 the oxidation state of oxygen is -1, configuration with a dihedral angle of 11 1.So as intermediate between the values for 02and HzO, and, as indicated by the reduction potentials 'I' F. PERCIVALand A. H. JOHNSTONE,Polywater -A on p. 628, aqueous solutions of H202 should Library Exercise for Chemistry Degree Students, The Chemi- spontaneously disproportionate. For the pure cal Society, London, 1978, 24 pp. [See also B. F. POWELL,J. Chem. Educ. 48, 663-7 (1971). H. FREIZER,J. Chem. Educ. 49, 445 (1972). F. FRANKS,Polywater, MIT Press, Cam- J.-M. SAVARIAULTand M. S. LEHMANN,J. Am. Chem. Soc. bridge, Mass., 1981, 208 pp.] 102, 1298-303 (1980). 634 oxysen Ch. 14 Preparation and Uses of Hydrogen Peroxide("3) Hydrogen peroxide is a major industrial chemical manufactured on a multikilotonne scale by an ingenious cycle of reactions introduced by I. G. Farbenindustrie about 60 years ago. Since the value of the solvents and organic substrates used are several hundred times that of the H202 produced, the economic viability of the process depends on keeping losses very small indeed. The basic process consists of dissolving 2-ethylanthraquinone in a mixed esterhydrocarbon or alcoholhydrocarbon solvent and reducing it by a Raney nickel or supported palladium catalyst to the corresponding quinol. The catalyst is then separated and the quinol non-catalytically reoxidized in a stream of air: The H202 is extracted by water and concentrated to -30% (by weight) by distillation under reduced pressure. Further low-pressure distillation to concentrations up to 85% are not uncommon. World production expressed as 100% H202 approached 1.9 million tonnes in 1994 of which half was in Europe and one-fifth in the USA. The earliest and still the largest industrial use for H202 is as a bleach for textiles, paper pulp, straw, leather, oils and fats, etc. Domestic use as a hair bleach and a mild disinfectant has diminished somewhat. Hydrogen peroxide is also extensively used to manufacture chemicals, notably sodium perborate (p. 206) and percarbonate, which are major constituents of most domestic detergents at least in the UK and Europe. Normal formulations include 15-25% of such peroxoacid salts, though the practice is much less widespread in the USA, and the concentrations, when included at all, are usually less than 10%. In the organic chemicals industry, H202 is used in the production of epoxides, propylene oxide, and caprolactones for PVC stabilizers and polyurethanes, in the manufacture of organic peroxy compounds for use as polymerization initiators and curing agents, and in the synthesis of fine chemicals such as hydroquinone, pharmaceuticals (e.g. cephalosporin) and food products (e.g. tartaric acid). One of the rapidly growing uses of H202 is in environmental applications such as control of pollution by treatment of domestic and industrial effluents, e.g. oxidation of cyanides and obnoxious malodorous sulfides, and the restoration of aerobic conditions to sewage waters. Its production in the USA for these and related purposes has trebled during the past decade (from 126 kt in 1984 to 360 kt in 1994) and it has substantially replaced chlorine as an industrial bleach because it yields only H20 and 02 on decomposition. An indication of the proportion of H202 production used for various applications in North America (1991) is: pulp and paper treatment 49%, chemicals manufacture 15%, environmental uses 15%, textiles 8%, all other uses 13%. The price per kg for technical grade aqueous H202 in tank-car lots (1994) is $0.54 (30%), $0.75 (50%) and $1.05 (70%), i.e. essentially a constant price of $1.50perkg on a "100% basis." 'I3W. T. HESS, Hydrogen Peroxide in Kirk-Orhnier Encyclopedia of Chemical Technology, 4th Edn., Wiley, New York, Vol. 13, 961-95 (1995). $14.2.3 Hydrogen peroxide 635 (a) Gas phase (b) Solid phase Figure 14.16 Structure of the H202molecule (a) in the gas phase, and (b) in the crystalline state. Table 14.12 Dihedral angle of H202 in some crys- peroxonium salts (H200H)+, hydroperoxides talline phases (0OH)- and peroxides (O&, and (iii) its Compound Dihedral Compound Dihedral reactions to give peroxometal complexes and angle angle peroxoacid anions. H202(~> 90.2" Li2C204.H202 180" The ability of H202 to act both as an oxidizing K&Od.H202 101.6" Na&O4.H2O2 180" and a reducing agent is well known in analytical Rb2C204.Hz02 103.4" NbF.H202'"4' 180" chemistry. Typical examples (not necessarily of H202.2H20 129" analytical utility) are: Oxidizing agent in acid solution: liquid: HzOz(1) -HzO(1) + ;02(g); AH' = 2[Fe(CN)6I4- + Hz02 + 2H' -98.2kJmol-', AGO = -119.2kJmol-'. In 2[Fe(CN)6l3- 2H20 fact, in the absence of catalysts, the compound + decomposes negligibly slowly but the reaction Likewise Fez+ +. Fe3+, SO3'- + SO4'-, is strongly catalysed by metal surfaces (Pt, Ag), NH2OH + HN03 etc. by Mn02 or by traces of alkali (dissolved from glass), and for this reason HzOz is generally Reducing agent in acid solution: stored in wax-coated or plastic vessels with sta- Mn04- + 2$H202+ 3H+ bilizers such as urea; even a speck of dust can - initiate explosive decomposition and all handling Mn2+ + 4H20 + 2i02 of the anhydrous compound or its concentrated solutions must be carried out in dust-free condi- 2Ce4+ + H202 -2Ce3+ + 2H+ + 02 tions and in the absence of metal ions. A useful Oxidizing agent in alkaline solution: "carrier" for H202 in some reactions is the adduct (Ph3P0)2.H202. Mn2+ + Hz02 --+ Mn4+ + 20H- Hydrogen peroxide has a rich and varied Reducing agent in alkaline solution: chemistry which arises from (i) its ability to act either as an oxidizing or a reducing agent in 2[Fe(CN),I3- + H202 + 20H- -+ both acid and alkaline solution, (ii) its ability 2[k(CN)6l4- + 2H20 + 02 to undergo proton acidhase reactions to form 2Fe3+ + H202 + 20H- - * l4 V. A. SARIN, V. YA. DUDAREV,T. A. DOBRYNINAand 2Fe2+ + 2H20 + 02 V. E. ZAVODNIK,Soviet Phys. Crystallogr. 24,472-3 (1979), and references therein. mo4 + H202 mo3 + H20 + 02 636 Oxygen Ch. 14 It will be noted that 02is always evolved when reagent (Fe2+/H202). The most important free H202 acts as a reducing agent, and sometimes radicals are OH and OzH. this gives rise to a red chemiluminescence if the Hydrogen peroxide is a somewhat stronger dioxygen molecule is produced in a singlet state acid than water, and in dilute aqueous solutions (p. 605), e.g.: has pK,(25') = 11.65 f0.02, i.e. comparable Acid solution: with the third dissociation constant of H3P04 (p. 519): HOC1 + H202 ---+ H3O' + C1- + 'Oz* ---+ h~ H202 H20 H30+ OOH-; Alkaline solution: + + + [H3Ot][0OH-] Clz + HzOz + 20H- ---+ 2C1- + 2HzO K, = = 2.24 x lo-" moll-' rH2021 + IO** __f hv Conversely, H202 is a much weaker base than The catalytic decomposition of aqueous solutions H20 (perhaps by a factor of lo6), and the fol- H202 alluded to on p.
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