Mechanism of the side-chain alkylation of toluene with methanol

Journal Article · Fri Aug 01 04:00:00 EDT 1980 · J. Catal.; (United States)

DOI:https://doi.org/10.1016/0021-9517(80)90503-5· OSTI ID:6313323

Itoh, H; Mijamoto, A; Murakami, Y

The side-chain alkylation of toluene at a 6:1 toluene-methanol ratio and 425/sup 0/C over potassium-exchanged X-zeolite in a flow reactor yielded 7.1% ethylbenzene and 7.4% styrene. Various other potassium-exchanged zeolites were less active. The pulsed reaction of toluene and methanol produced much more styrene than ethylbenzene, which indicated that styrene is a primary product which is further hydrogenated to ethylbenzene. A mechanism is proposed in which methanol is dehydrogenated to formaldehyde which acts as methylation agent. The mechanism was verified with quantum chemical calculations which also indicated that specific configurations of basic and acid sites with steric restrictions are required for the side-chain alkylation, whereas the alkylation of the benzene ring takes place on an acidic site.

• Research Organization: Nagoya Univ.
• OSTI ID: 6313323
• Journal Information: J. Catal.; (United States), Journal Name: J. Catal.; (United States) Vol. 64:2; ISSN JCTLA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
ALCOHOLS
ALDEHYDES
ALKYLATED AROMATICS
ALKYLATION
AROMATICS
CALCULATION METHODS
CATALYTIC EFFECTS
CHEMICAL REACTION KINETICS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CHEMICAL REACTORS
COMPARATIVE EVALUATIONS
CONFIGURATION
DATA
EXPERIMENTAL DATA
FORMALDEHYDE
HIGH TEMPERATURE
HYDROCARBONS
HYDROXY COMPOUNDS
INFORMATION
INORGANIC ION EXCHANGERS
ION EXCHANGE
ION EXCHANGE MATERIALS
KINETICS
MATERIALS
METHANOL
METHYLATION
MINERALS
NUMERICAL DATA
ORGANIC COMPOUNDS
PH VALUE
QUANTITY RATIO
REACTION KINETICS
STEREOCHEMISTRY
STYRENE
TOLUENE
YIELDS
ZEOLITES