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Addition Polymerization (Macropolymerization) /. Introduction Acid-catalyzed addition polymerization, also called macropolymerization, of olefins may lead to the formation of h y d r o c a r b o n s of high molecular weight. Although the chemistry of macropolymerization is outside the scope of this b o o k , it w a s nevertheless d e e m e d advisable to p r e s e n t a brief discussion of it since this might lead to a b e t t e r understanding of the chemistry of acid-catalyzed polymerization r e a c t i o n s .

Isolated e x p e r i m e n t s w e r e m a d e with o t h e r alkanes containing a tertiary c a r b o n a t o m a t t a c h e d to h y d r o g e n , s u c h as isopent a n e and 2-methylpentane, b o t h of which react with alkenes to form alkylates. H o w e v e r , m o s t of the k n o w l e d g e u s e d t o interpret t h e m e c h a n i s m of reaction w a s derived from the study of i s o b u t a n e , and for that r e a s o n the reaction of alkenes with isobutane is d i s c u s s e d in m o r e detail.

T h e propagation reaction requires the least activation e n e r g y . At low t e m p e r a t u r e it pred o m i n a t e s over the termination reaction, but at higher t e m p e r a t u r e s the 1 48 1 Acid-Catalyzed Reactions relative rates of termination increase and p o l y m e r s of lower molecular weight result. A more complicated termination step may o c c u r at a higher t e m p e r a ture wherein the H of an a l k e n e , n a m e l y , an allylic hydride from the mono m e r , is transferred to the growing p o l y m e r cation: • I R'CH 2— C—C R'CH—C=C / R + R I R'CH=C—C , i l l R H ι + —C—(C—C-^—C—CR R I I H • H I I —C—(C—C-h—C—CR —CH I I ' ' T h e allylic cation m a y complex with the catalyst and h e n c e deactivate the catalytic action of the acid as explained in Section III,C on conjunct polymerization.

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