4. AUTOXIDATION AND OTHER LIPID REACTIONS
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- Bertram Carson
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1 4 AUTXIDATIN AND TE LIPID EACTINS A) Technologically significant reactions (oleochemistry) esterification enzymatic (lipases) nonenzymatic (acid and base catalysis) esterifications 0-00 C, S 4, Cl - + -C -C + glycols, alditols + FA emulsifiers glycerol + FA (hydroxyl acid) emulsifiers interesterification acidolysis -C + -C -C + -C without catalyst, C; with catalyst S 4, C TAG + abietic acid varnish TAG + phthalic acid glyptals (drying oil ~ natural resins exchange lower/higher FA coconut oil, palm kernel fat alcoholysis -C + - -C + - Na, Na 0 C and more, S 4 ~ 00 C, with catalyst at 50 C methanolysis Me-esters, biofuels butanolysis Bu-esters (plasts softenings) glycerolysis parcial esters (emulsifiers) transesterification -C + -C 3 -C 3 + -C without catalyst ~ 50 C, acidic, basic catalyst 00 C cacao butter, randomisation (melting point higher for about 0 C) oil + tallow digestability, consistence molecule splitting -C -C + - saponification - MPa hydroxides, soaps as products
2 3 hydrogenation -C=C- -C -C -, C, Ni-catalyst; 0,-0, MPa hardened fats (hardening, hydrogenation) composition of fatty acids (book, tab343) C C C C C linolová 3 0 C C C C C olejová C C C C C k k stearová C C C C C oktadec--enová stability against oxidation, consistency, absence of trans-acids side-reactions cis/trans isomerisation (30-45 % trans-isomers) positional isomerisation (unusual isomers) hydrogenation smell: -linolenoic (Z,E)-oktadeca-,5-dienoic (E)-non-6-enal other products (fatty alcohols, ethers) FA - (~ 0 MPa) esters ethers type -- (nonresorbate fats) B ancidity of oils and fats hydrolytic rancidity scented rancidity reversion oxidation hydrolytic rancidity enzymatic reaction: lipases (butter, coconut oil, palm oil) chemical reaction: frying TAG FA + partial esters butter, milk, coconut oil, palm oil undesirable chocolate partly desirable cheese desirable threshold value (mg/kg) free fatty acids, smell, taste (bitter)
3 scented rancidity enzymatic reaction: mikroorganisms and their enzymes FA with short and medium carbon chain milk fat, coconut oil, palm oil undesirable mould cheese desirable reversion chemical reaction (autooxidation) wornish, fish and bean smell in oils containing C :3 acids (soybean oil) C5 oxidative rancidity consequences negative lowering of sensory quality lowering of nutritive value, reaction of oxidised lipids with proteins lowering of hygiene-toxicological quality, toxic products aging, illness (in vivo) positive formation of aromatic compounds nonenzymatic reaction air oxygen ( 3 ) reactive forms of oxygen (singlet oxygen, radicals, ) singlet oxygen formation: photosensitised reactions 3 pigments (riboflavin, chlorophyll, hem) free radicals - (superoxide radical) - (hydroxyl radical) enzymatic reactions lipoxygenases (lipoxidases) 3
4 nonenzymatic reactions oxidation by triplet oxygen, autoxidation general mechanism of hydrocarbon chain autoxidation (radical reaction) induction stage - + iniciators, homolytic decomposition hydrocarbon radical propagation stage up to thousands of segments (influence temperature p ) hydroperoxide= primary oxidation product hydroperoxides decomposition hydroperoxyl radical hydroperoxide 3 terminal stage mutual radical reactions, polymers of different type bound C-C bound C---C induction mostly photooxidation and enzymatic reaction singlet oxygen hydroperoxide, first radicals forming due to decomposition of hydroperoxides decomposition of hydroperoxides monomolecular decomposition and bimolecular decomposition (at higher concentration ) alkoxyl radical as a new species reactivity of radicals - -- fate of alkoxyl radicals decomposition aromatic compounds recombination in terminal stage 4
5 bound C--C oxidation of unsaturated acids (at ordinary temperature) : L : LL = : 0 : 00 structure dissociation energy (kj / mol) -C - 4 C 3 -C C-C=C- 3 -C=-C--C-C=C- 7 C C C oxidation of saturated acids (at elevated temperature) 3 (7) kj/mol C C C 4 kj/mol C C C C C radikály o frying and roasting mechanisms: oxidation of oleic acid mixture 4 hydroperoxides in retio of cca ::: cis (or trans), trans - oxidation of linoleic acid 0 C C C C C C C C C C C C C 0 C -hydroperoxy--enová k C C C C -hydroperoxy-0-enová k mixture 7 hydroperoxides, mostly - a 3-0 C C C C C C geometric isomers positional isomers 0 0 C C C C 0 C C C C -hydroperoxy--enová k C C C C 0-hydroperoxy--enová k oxidation of linolenoic acid 5
6 mixture of many hydroperoxides mostly -, -, 3- and 6- with conjugated double bonds and one isolated bond subsequent reaction of hydroperoxides secondary autooxidation products same number C lower number C higher number C epoxy-, hydroxy-, oxo-acids aldehydes, hydrocarbons and others different polymers formation of epoxy-, hydroxy- a oxo-compounds C C C C C C C C C - epoxykyselina C C C hydroxykyselina C C C C C C C C C - C C C oxokyselina epoxykyselina formation of aldehydes and hydrocarbons general mechanisms C C C - hydroperoxid C C C alkoxylový radikál C C + C C C C + oxokyselina aldehyd C C C C - aldehyd uhlovodík mastná kyselina for example -hydroperoxy-0,-fatty acid from linoleic acid - hydroxykyselina 6
7 C C C C hydroperoxid C C C C alkoxylový radikál C C + C C C C + C C C C C C aldehyd C oxokyselina C C C aldehyd -oxononanoic, octanoic, (E,Z)-deca-,4-dienal, (Z)-non-3-enal, C3 mastná kyselina subsequent reaction of aldehydes polymers formation bond C-C ether bond peroxide bond two-fold C-C bond tetrahydrofurane bond C-C peroxide bound cyclopentane cycle two-fold bond C-C tetrahydropyrane bond dioxane bond reaction of oxidised lipids with proteins oxidation with singlet oxygen photooxidation (photosensitilisators) enzymatic reaction (photosynthesis) 7
8 S senzibilizátor S h * 3 excitovaný singletový senzibilizátor - - typ I S * excitovaný tripletový senzibilizátor S + typ II S- radikál redukovaného kation senzibilizátoru senzibilizátoru - S 3 singletový kyslík - hydroperoxid -- addition on double bound, ~ 000 times faster than autoxidation C : - a 0-hydroperoxid C : - a 3-hydroperoxid 0 C :3 -, -, 3-, 6- a 0-, 5,-hydroperoxid 0 hydroperoxidy compoundss destroying singlet oxygen -carotene and other carotenoides tocopherols ascorbic acid carotenoid + 3 karotenoid carotenoid (excited triplet state) carotenoid enzymatic oxidation lipoxygenases (lipoxidases, linoleate: oxidoreductase), E : = 7 kj/mol En unsaturated lipid hydroperoxides of unsaturated lipids (optically active) C C C C C C
9 C : - a 3-hydroperoxids 0-hydroperoxids C :3 - a 3-hydroperoxids 0-hydroperoxids specificity (regio-, stereo-) example C : soya (3S)-, -cis-, -transtomatoes (S)-, 0-trans-, -cis mushrooms (0S)-, -trans-, -cis negative, positive consequences animals: decomposition by glutathionperoxidases plants and mushrooms: splitting by lyases, isomerases, aroma compounds 3--,,5- ~ C3 C (Z)-hex-3-enal (green flavour) (E)-hex--enal, leaf aldehyde, product of isomeration of (Z)-hex-3-enal by isomerases oily, greasy, green smell --0,,5- ~ C 3 C 0--,- ~ (Z)-non--enal (oily smell) C3 C thermal reactions geometrical isomerisation positional isomerisation cyclisation ()-okt--en-3-ol (mushroom-like smell) cis/trans
10 polymerisation Diels-Alder reaction (monoene C : and diene C : ) C : C : 3 4 dimer mechanisms of oleic acid isomers formation (~70 C) = = - 0 (Z)--oktadecenová (olejová) kyselina (C ) 6 C 3 (C ) 6 C inhibition of autooxidation temperature air radiation - volný radikál volný radikál inhibitors (antioxidants, synergists) C C C C mesomerní stav C C C C mesomerní stav (E)--oktadecenová (elaidová) kyselina (E)--oktadecenová kyselina 0 (E)-0-oktadecenová kyselina antioxidants classification according to origin natural (mostly tokopherols, phenols synthetic (mostly phenols) 0
11 classification according to activity (mechanisms) primarary (reaction with s radicals) secondary (reduction of --) phenolic antioxidants (mechanism of action) A A -A (antioxidant) main reactions A A-A A A A A side reactions ( 0,0 %) A + A-- A A--- + A (radical antioxidant) main natural antioxidants C3 main synthetic antioxidants tocopherols C gallates C 3 C3 C3 BT BA (isomers cca : ) TBQ applications BA, BT, tocopherols, dodecylgallate type of emulsion: oil/water TBQ, propylgallate pure fats (oils)
12 00 P I I t 0 evaluation of fat oxidation induction period P - peroxide number, t time of autoxidation at 60 o C (days), - concentration of antioxidants (BA) = 0 %, - 0,0 %, I a I = induction periods, protective factor PF = (I -I )/I
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