Radiation Processing. Chemical Effects

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1 Radiation Processing Chemical Effects

2 Reactions ofhydrated Electron Major Reactions of e-aq H e- aq + N 2 0 N 2 + {)H Used to detect/estimate e- aq and to increase OH yield 2. e- aq + O H0 2 Used to produce 02- ' prevalent in systems open to air 3. e- aq + C 6 H si C 6 H s l + r Dissociative electron capture by halogenated organics can be used to detect and estimate e- aq 4. e-aq + Fe 3 + Fe 2 + e- aq + N0 3 - NOl- Reactions with cations and many anions are known to occur

3 Reactions ofhydrated Electrons (contd) 5. Reduces carbonyls to hydroxy derivatives several 6. Decreases aromaticity steps Naphthalene several H I.~ :r I steps ~~...~ Dihydronaphthalene 7. Reacts with cellular constituents (e.g. amino acids) e- aq + NH 3 +CHRCOO- - NH 3 + CHRCOO - NH 2 + RCHCOOH -..~ H + NH 2 CHRCOO-

4 Reactions of OH The major types of reactions are 1. Addition to double bonds OH I. >C=C< + OH >C - C< 2. Hydrogen abstraction 3. Electron transfer Br- + OH - Br + OH- Fe OH Fe OH-

5 Reactions of OH (contd) 4. Produce ketones from alcohols (CHa)2CHOH + OH ~ (CH a )2 COH + H20.. (CHa)2COH + (CHahCOH ~ (CHa)2-C-OH I (CHah-C-OH ~ (CHahCHOH + (CHahCO Hydroxyl radical is just about the most reactive free radical known

6 Reactions ofhydrogen Atom The two main reactions are addition to double bonds and hydrogen abstraction 1. Addition to double bond H I. > C = C < + H ~ > C - C < 2. Hydrogen abstraction RH + H With oxygen, it gives the superoxide anion

7 Differentiation ofreactive Species One can differentiate between reactions of the different reactive species by choosing appropriate conditions In inert atmosphere (e.g., N 2 or vacuum) all three, e- aq, H and 'OH are present In the presence of N 2 0 the predominant free radical is 'OH (90% OH, 10 % 'H) In air the reactive species is mainly OH (,...,45% unreactive 02-'/HO'2,...,55%) + rather In the presence of O 2 and formate (10-2 to 10-1 mol.dm- 3 ) only 02- /HO"2 are present OH + HCO- 2 H + HCO- 2 O2+ CO ,... CO- 2 + H ;~~ CO 2' + H ,..~ 0-2" + CO 2

8 Comparison of'h With 'OH and e- aq. Reactivity Inactivation Efficiencies of Reactive Free Radical Species with Ribosomes Species Relative Inactivation Efficiency In Vacuum Expected in air a OH e"aq H Increased damage due to peroxidation b Damage from superoxide anion (0-2 -) Singh and Singh (1983)

9 ph Dependence ofyields on Radiolysis ofwater Qj 3 =-~2 I Co-' 1 e- + H+ -+ H aq H + OH- -+e-aq 4--r O~~ 'OH e aq ~~--...-_-~:';:;;;;;;;;;;..,;;;;;;.J ph The ph range of most foods lies between 2 and

10 Some Reaction Rate Constants in Aqueous Solutions at 20 C Reactant, k(e"aq + S) K( OH + S) k( H + S) S 1.2 X x x X X X X X X X x10 9 9x X slow 5 x X 10 6 <10 7 no reaction < x 10 7 "" X 10 9 no rection "" 10 4 no reaction 1.1 x 10 9 no reaction no reaction 10 9 no reaction 1.2 x x x X no reaction 2 x Fe 2 + Mn 2 + Cu 2 + NO"2 NO"3 H 2 PO"4 HCO"3 CO 2 Br CI" H O 2 (Units: mol"1.dm 3.s"1) In general - e- aq is a very strong reducing agent - H is a weaker reducing agent, and - OH is a strong oxidizing agent

11 Some Reaction Rate Constants in Aqueous Solutions at 20 C Reactant, k(e- aq + S) K( OH + S) k( H + S) S Fe x 10 8 Mn x 10 7 Cu x NO X 10 9 NO X H 2 PO x 10 6 HCO- 3 <10 6 co X 10 9 Br no reaction CI- no reaction H x O X (Units: mol- 1.dm 3.s- 1 ) 3 X X x10 8 3x X X x10 9 9x10 6 slow 5 x 10 6 <10 7 no reaction 1 x 10 7, no rection, x 10 9 no reaction 10 9 no reaction 2.2 x x 10 7 no reaction 2 x In general ~-,ag_is a very strong reducing agent M 15 a weal<er reducing agent, and OH is a strong oxidizing agent

12 Some Reaction Rate Constants in Aqueous Solutions at 20 C (contd) Reactant, 5 k(e- aq + 5) Aliphatic Negligible a a hydrocarbons (CH 3 hco 5.9 x x x 10 5 >C=C< 10 6,...,109,...,109 >C=C-C=C< 8 x ROOH, ROOR RCI b b RN b b Aromatics ,...,10 8-5H,...,1010,...,1010,..., ,...,1010,...,1010,...,109 H 2 NCH 2 COOH 8.2 x x x 10 4 a Depends on the C-H bond strength, b Depends on R

13 Some Reaction Rate Constants in Aqueous Solutions at 20 C (contd) Protection of biological systems by the -SH compounds is due to their very high reactivity with all of the three primary species from water The >C=C-C=C< would be the next best. However, its secondary radical could be damaging to biological systems, but RS is not

14 Reactions ofhzoz 1. Formation OH + OH H H (in vacuum/n 2 ) ---l.~ H 2 0 (in air) 2. Reactions Fenton Reaction H Fe 2 + Fe OH- + OH HRP Reaction H HRP -...HRP-I RH + HRP-I R + HRP-II RH + HRP-II R + HRP Overall, it is a mild oxidizing agent; it oxidizes phenols and inactivates enzymes

15 Other Secondary Reactive Species 1. Superoxide Anion (0 2 -.) Formation e- aq + O 2 Reactions o H+ 2 2 o -. + SOD-Cu Superoxide Dismutase SOD-Cu+ + O H '... H O SOD-Cu Singlet Oxygen (10 2 ) A minor species which oxidizes unsaturated compounds Lipids Lipid Hydroperoxide (ROOH) ROOH + Fe 2 + RO + OH- + Fe 3 + Alkoxy Radical (Fenton like reaction)

16 Detection ofvarious Reactive Species e"aq OH H H ESR -ESR -ESR -ESR/Fenton Reaction ( OH formation) -Optical absorption -Reaction with N 2 0 -C 2 H 4 formation with methional -Bleaching of p-nitrosodimethylaniline -Hydroxylation of phenol and/or salicylic acid -Reaction with tryptophan -Formation of characteristic products following its reactions (e.g., H 2 ) -Inhibition of its reaction by catalase -Iodine liberation from acidified KI solutions

17 Absorption Spectra of Some Species in Water I HO E (.)... -I III H C?E 80 E'" "C 60 -CIJ 4 C\I 40 I , Wavelenth (nm) T

18 Reactions of Organic Free Radicals 1. Peroxy Radicals Formation R +0 2 R0 2 (Peroxy Radical) Reactions R0 2 + RSH RO + RO -... ROOH + (hydroperoxide) RO + O 2 (alkoxy radical) RO RO-OR (organic peroxide) RS (thiyl radical) Peroxy radicals are the main vehicle of lipid peroxidation leading to rancidity of oils and fats

19 Reactions of Organic Free Radicals (contd) 2. Hydrogen Abstraction R + R1 H RH + R1 (less efficient than OH or H ) 3. Addition to Double Bonds R I. R + > C = C > C - C < (usually, not as efficient as the addition of H or OH) 4. Recombination R + R R-R 5. Disproportionation

20 Radiolysis of Cyclohexane o C 6 H 12 Products H 2 c-c S H 10 (c-c S H 11 h CH=CH(CH2hCH2 c-c S H 7 -CH 3 C-CSH11-(CH2)4CH=CH2 n-c S H 14 unidentified C12 C-CSH11-C2Hs Initial Yield (molecules/100 ev) ± ± I'J 0.05 I'J 0.04

21 Gamma Radiolysis ofliquid Cyclohexane in the Presence of Oxygen G (Product) Product Evacuated Sample in 02 Sample (2 mol m- 3 ) 1-Hexene Hexane 0.1 <0.01 Methylcylopentane Cyclohexene Bicylohexyl Cylohexanol Cylohexanone Peroxides

22 Radiolysis ofbenzene ~~ C 6 H 6 Products Hydrogen Ethylene Acetylene 1,4-Cyclohexadiene 1,3-Cyclohexadiene Phenyl-2,4-Cyclohexadiene Phenyl-2,5-Cyclohexadiene Biphenyl C e units incorporated in polymers G (molecules/100 ev)

23 Radiolysis of Chlorobenzene Yields ofmajor Products a Product G(Product) Hydrogen 0.01 Hydrochloric acid 0.25 Benzene 2.91 Biphenyl 0.12 Dichlorobenzene 0.36 Chloro-biphenyl 0.90 a Dose, 208/kGy (Spinks and Woods, 1990)

24 'Y- Radiolysis ofliquid Acetone and Methyl Acetate at C, G(Products) Product Acetone Methyl Acetate (CH 3 COCH 3 ) (CH 3 COOCH 3 ) Hydrogen Carbon Monoxide Carbon Dioxide Methane Ethane Acetaldehyde Dimethyl Ether Acetic Acid Biacetyl Methyl Ethyl Ketone 2-Propanol (CH 3 COCH 2 )2 CH 3 COCH 2 COCH

25 Conclusions - Understanding of the detailed chemical processes occurring on irradiation has helped develop many of the commercial applications of radiation processing, e.g., curing of coatings, crosslinking of polyethylene, and purification of water in the presence of ozone -Continuing effort in this area is needed to improve current, and develop new, chemical effect based processes

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