Reactivities of Di(1-naphthyl)methane and Hydrogenated Di(1-naphthyl)methanes toward Hydrocracking over Ni−S

Abstract

Hydrocracking reactions of di(1-naphthyl)methane (DNM) and hydrogenated di(1-naphthyl)methanes (H-DNMs) were investigated at 300 °C to examine the relationship between structure and reactivity of the substrates. The results show that in the presence of Ni−S DNM is readily hydrocracked to naphthalene and 1-methylnaphthalene under pressurized hydrogen, while the more deeply DNM is hydrogenated, the more slowly the resulting H-DNMs are hydrocracked. The differences between DNM and H-DNMs and among the different H-DNMs in reactivity toward hydrocracking can be ascribed to the hydrogen-accepting abilities of ipso-carbons in the substrates, the stabilities of leaving arylmethyl radicals and the adsorption strength of the substrates on catalyst surface.

A Novel Magnetic Solid Acid for Specially Cleaving the C‐O Bridged Bond in Dibenzyl Ether

“…A part of benzyl cation attacks the benzene ring ortho‐position of benzyl alcohol to produce intermediate (IM3) . Then the intermediate becomes protonated ether (TS3) by intramolecular hydrogen transfer, and the protonated ether loses H 2 O to produce carbonium ion intermediate (IM4) quickly.…”

Preparation of a new solid acid and its catalytic performance in di(1-naphthyl)methane hydrocracking

“…The dissociation energy of Car-Calk bond in DNM was reported to be 355.6 kJ/mol, therefore thermal cleavage of the Car-Calk bond in DNM at 300 C is extremely difficult [29]. Hydrogen transfer either from H • or H + greatly facilitates Car-Calk bond cleavage, as the attack of H • or H + on the ipso-position of an aromatic ring connected to methylene yields a stable arene rather than a labile aryl radical in addition to a relatively stable leaving group, i.e., an arylmethyl radical or arylmethylium [30,31].…”

Catalytic hydrocracking of bitumen at mild experimental condition

“…When simple feed is hydrocracked, the product yield can be calculated by GC/MS [20]; however, heavy residue is cracked and product yield can be suggested based on boiling point cut [21]. Recently, we reported that bitumen can be fractionated by TGA, which shows similar results of boiling point cut [13].…”