Ion exchange resin catalyzed addition of alcohols to olefins

Ancillotti, Francesco; Mauri, Marcello Massi; Pescarollo, E.

doi:10.1016/0021-9517(77)90134-8

Cited by 162 publications

(58 citation statements)

References 24 publications

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“…In etherification reactions, E'a,i was found to increase as the exothermicity of reaction decreases, that is in the order R1< R2 < R3. E'a,R1 is in good agreement with published values in the synthesis of ETBE over Amberlyst™ 15 by Ancillotti et al [46], and over Amberlyst™ 35 by Gonzalez [28]. E'a,R2 and E'a,R3 are in reasonable agreement with those determined by Linnekoski et al [9] in the synthesis of TAEE over Amberlyst™ 16.…”

Section: Figuresupporting

confidence: 89%

Kinetic modeling of the simultaneous etherification of ethanol with C4 and C5 olefins over Amberlyst™ 35 using model averaging

Fité

Ramírez

Bringué

et al. 2017

Chemical Engineering Journal

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Graphical abstract Highlights Model averaging provides the kinetic model taking into account model uncertainty  ETBE is formed faster than TAEE in the simultaneous etherification  Reactions mechanism is deduced from the proposed kinetic model  Active sites are mainly occupied by adsorbed ethanol, ETBE and TAEE  Two active sites participate in etherification reactions, and one in isomerization AbstractA kinetic study on the simultaneous liquid-phase etherification of ethanol with isobutene (IB), 2-methyl-1-butene (2M1B) and 2-methyl-2-butene (2M2B) catalyzed by Amberlyst™ 35 to form ethyl tert-butyl ether (ETBE) and tert-amyl ethyl ether (TAEE) is presented. Isothermal experimental runs were carried out in a stirred tank batch reactor in the temperature range 323-353 K at 2.0 MPa, starting from different initial concentrations. Obtained reaction rates were free of catalyst load, internal, and external mass transfer effects. Mathematical fitting of a series 2 of systematically originated models, model selection, and model averaging procedures were applied to find the best model and to draw conclusions about the reaction mechanism. The selected model involves a saturated catalytic surface with the participation of two active sites in etherification reactions and one active site in isoamylenes isomerization. Apparent activation energies for ETBE formation from IB and EtOH, TAEE formation from 2M1B and EtOH, TAEE formation from 2M2B and EtOH, and double bond isomerization between 2M1B and 2M2B were 72.8±1.4, 74.9±2.8, 81.2±2.2 and, 76.5±7.2 kJ/mol, respectively. The alkenes with the double bond in terminal position were more reactive towards EtOH than 2M2B, with the double bond in internal position.

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Section: Figuresupporting

confidence: 89%

Kinetic modeling of the simultaneous etherification of ethanol with C4 and C5 olefins over Amberlyst™ 35 using model averaging

Fité

Ramírez

Bringué

et al. 2017

Chemical Engineering Journal

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“…This has also been observed by other authors [18][19][20], and seems to be a characteristic value for acid-catalyzed reactions in the presence of resins, such as ether synthesis by reaction between alcohols and olefins. In general, the non-linear dependence of the reaction rate on the catalyst concentration (n = 2.7) is not straightforward to explain.…”

Section: Development Of a Kinetic Model And Reaction Mechanism For Thsupporting

confidence: 84%

“…In particular, different kinds of mechanisms have been applied in the related literature, such as Langmuir-Hinshelwood or Eley-Rideal mechanisms, but without giving good results. Actually, as it is evident from findings in the literature [20], the protonating power of the resin does not linearly depend on the concentration of sulphonic groups, explaining the non-linear dependency of the reaction rate on the catalyst concentration.…”

Section: Development Of a Kinetic Model And Reaction Mechanism For Thmentioning

confidence: 87%

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Synthesis of Biolubricant Basestocks from Epoxidized Soybean Oil

et al. 2017

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This work deals with the preparation of biolubricant basestocks through the ring-opening reaction of epoxidized soybean oil (ESO) by alcohols in presence of solid acid catalysts (SAC-13 resin). To this end, different experimental runs were carried out in a lab-scale reactor, analyzing the effect of the alcohol (methanol, ethanol, 2-propanol, 2-butanol), catalyst mass loading (from 1 to 10 wt % with respect to the oil mass) and operating temperature (60-90 • C). The main focus of investigation was oxirane conversion. The study was complemented by FT-IR, 1 H NMR and kinematic viscosity characterization of the different products of the ring-opening reaction. Experimental conversion data were fitted through a suitable kinetic model. Values of the best-fitting parameters in terms of rate constant, activation energy and catalyst reaction order were obtained, and were potentially useful for the design of an industrial process.

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“…In the present work the activity of several catalysts derived from a montmorillonite are compared with that of the macroreticular sulphonic acid resin Amberlyst 15 (Anonymous, 1967) which is similar to the acidic resin used industrially for the production of MTBE (Ancillotti et al, 1977). Ancillotti et al (1977Ancillotti et al ( , 1978 and Gicquel and Torck (1983) showed that at methanol:isobutene ratios reasonably close to unity the pore spaces of Ambeflyst 15 resin are filled with methanol, which acts as the solvent at the reaction site in the formation of MTBE.…”

Section: Meoh + Ch2=c(c[--i3)2 --* Me-o--(2(ch3)3mentioning

confidence: 99%

Methyl t-Butyl Ether (MTBE) Production: A Comparison of Montmorillonite-Derived Catalysts with an Ion-Exchange Resin

Adams

1986

Clays and clay miner.

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Abstract--Montmorillonite-based catalysts were compared with an acidic ion-exchange resin of the type used industrially for the production of methyl t-butyl ether (MTBE) from methanol and isobutene or t-butanol. When 1,4-dioxan was used as solvent, Al3+-exchanged montmorillonites had about half the efficiency of the resin Arnberlyst 15 at 60~ they were, however, about twice as efficient at this temperature at Ti3+-montmorillonite or K10, a commercially available acid-treated bentonite. Montmorillonite exchanged with Chlorhydrol solutions to give interlayer [AI1304(OH)2(H20)12] 7+ ions and pillared clays derived from such materials were poor catalysts, as was K306, a more drastically acid-treated bentonitebased commercial catalyst. Freeze-drying of the AP+-day before reaction to produce a more open, porous structure had no effect on its catalytic efficiency. The activation energy for the reaction of isobutene and methanol in dioxan was 44 El/mole for an AP+-clay catalyst compared with 25 kJ/mole for reactions catalyzed by Ambedyst 15. With no solvent (as in industrial processes), the rates of reaction were considerably slower for both the clay-and resin-catalyzed reactions. As has been found previously for resin-catalyzed reactions using stoichiometric amounts or an excess of methanol, the rate was proportional to the isobutene concentration, and the rate-determining step appeared to be protonation of the alkene. The performance of the AP+-clay catalyst was increased by reducing the water content of the clay. In most reactions the clay catalysts were equilibrated at 12% relative humidity. Exposure of the clay to a low vacuum (10-1 ton-) before use increased its catalytic activity from 50 to 60% of that of Amberlyst 15.

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Ion exchange resin catalyzed addition of alcohols to olefins

Cited by 162 publications

References 24 publications

Kinetic modeling of the simultaneous etherification of ethanol with C4 and C5 olefins over Amberlyst™ 35 using model averaging

Kinetic modeling of the simultaneous etherification of ethanol with C4 and C5 olefins over Amberlyst™ 35 using model averaging

Synthesis of Biolubricant Basestocks from Epoxidized Soybean Oil

Methyl t-Butyl Ether (MTBE) Production: A Comparison of Montmorillonite-Derived Catalysts with an Ion-Exchange Resin

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