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Titre du document / Document title

Mechanism and kinetics of the acid-catalyzed dehydration of 1- and 2-propanol in hot compressed liquid water

Auteur(s) / Author(s)

ANTAL M. J. (1) ; CARLSSON M. (1) ; XIAODONG XU (1) ; ANDERSON D. G. M. (2) ;

Affiliation(s) du ou des auteurs / Author(s) Affiliation(s)

(1) Hawaii Natural Energy Institute, 2540 Dole Street, University of Hawaii at Manoa, Honolulu, Hawaii 96822, ETATS-UNIS
(2) Division of Engineering and Applied Sciences, Harvard University, Cambridge, Massachusetts 02138, ETATS-UNIS

Résumé / Abstract

Only propene and 1-propanol are observed as products of the acid-catalyzed dehydration of 2-propanol in compressed liquid water after 100 s or less at 320°C. Likewise, only propene, 2-propanol, and traces of n-propyl ether are observed as products of the acid-catalyzed dehydration of 1-propanol under the same conditions. Kinetic analyses of the experimental data indicate that propene is formed from 1-propanol by an acid-catalyzed E2 mechanism that involves only protonated 1-propanol as an intermediate. Byproduct n-propyl ether is formed by an AdE3 mechanism involving propene, 1-propanol, and acid. The formation of propene from 2-propanol is kinetically consistent with both an acid-catalyzed E2 mechanism and an acid-catalyzed E1 mechanism (that involves the bare i-propyl cation in addition to protonated 2-propanol as intermediates in the dehydration chemistry). Thus, the kinetic analysis does not enable to discriminate between the two mechanisms for 2-propanol dehydration. On the other hand, results of the kinetic analysis point to the important role of the undetected product i-propyl ether in the formation of propene from both 2-propanol and 1-propanol. This ether (which is not stable in hot liquid water) is formed by an AdE3 mechanism and decomposes via an uncatalyzed, unimolecular reaction. Experimental studies of the reactions of n-propyl ether and i-propyl ether are consistent with model predictions.

Revue / Journal Title

Industrial & engineering chemistry research    ISSN  0888-5885   CODEN IECRED 

Source / Source

1998, vol. 37, no10, pp. 3820-3829 (28 ref.)

Langue / Language

Anglais

Editeur / Publisher

American Chemical Society, Washington, DC, ETATS-UNIS  (1987) (Revue)

Mots-clés anglais / English Keywords

Dehydration

;

Alcohol

;

Hot water

;

Supercritical solvent

;

Catalytic reaction

;

Acid catalysis

;

Sulfuric acid

;

Kinetics

;

Conversion rate

;

Rate constant

;

Reaction mechanism

;

Kinetic model

;

Parameter estimation

;

Experimental study

;

Mots-clés français / French Keywords

Déshydratation

;

Alcool

;

Propan-1-ol

;

Propan-2-ol

;

Eau chaude

;

Solvant supercritique

;

Réaction catalytique

;

Catalyse acide

;

Sulfurique acide

;

Cinétique

;

Taux conversion

;

Constante vitesse

;

Mécanisme réaction

;

Modèle cinétique

;

Estimation paramètre

;

Etude expérimentale

;

Mots-clés espagnols / Spanish Keywords

Deshidratación

;

Alcohol

;

Agua caliente

;

Disolvente supercrítico

;

Reacción catalítica

;

Catálisis ácida

;

Sulfúrico ácido

;

Cinética

;

Factor conversión

;

Constante velocidad

;

Mecanismo reacción

;

Modelo cinético

;

Estimación parámetro

;

Estudio experimental

;

Localisation / Location

INIST-CNRS, Cote INIST : 120 F, 35400007123434.0040

Nº notice refdoc (ud4) : 2397469



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