Extractive hydration of n-butene with solid acid catalysts in the liquid phase and under supercritical conditions

Mahajani, Sanjay M.; Sharma, Man Mohan; Sridhar, T.

doi:10.1016/s0009-2509(01)00172-5

Cited by 9 publications

(4 citation statements)

References 14 publications

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“…Another interesting example is the hydration of butene to 2-butanol, which is performed in the presence of acid catalysts. A supercritical butene/water biphasic system is specially adapted for this application, as the solubility of butene in water is low and supercritical butene allows the separation of the product 2-butanol, shifting the reversible reaction in the forward direction . Supercritical fluids and GXLs have been used in recent years for multiphase catalytic reactions such as hydroformylations, hydrogenations, carbonylations, oxidations, and epoxidations by taking advantage of the tunability that these systems offer.…”

Section: Solubility Of Catalystsmentioning

confidence: 99%

“…A supercritical butene/water biphasic system is specially adapted for this application, as the solubility of butene in water is low and supercritical butene allows the separation of the product 2-butanol, shifting the reversible reaction in the forward direction. 69 Supercritical fluids and GXLs have been used in recent years for multiphase catalytic reactions such as hydroformylations, hydrogenations, carbonylations, oxidations, and epoxidations by taking advantage of the tunability that these systems offer. Some reviews in this field have been published by different authors, and we encourage interested readers to refer to them.…”

Section: ■ Introductionmentioning

confidence: 99%

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ScCO₂/Green Solvents: Biphasic Promising Systems for Cleaner Chemicals Manufacturing

Medina-González

Camy

Condoret

2014

ACS Sustainable Chem. Eng.

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Solvents play a key role in the chemical industry; novel classes of solvents such as gas expanded liquids and switchable solvents have attracted great interest in recent years as their emergence and utilization in chemical processes hold many promises to develop benign environmental technologies. This perspective paper aims at reflecting on the state of the art concerning biphasic scCO 2 /green solvent systems. Rather than discussing the reactions that have been performed in each major type of scCO 2 /green solvent biphasic system, this paper is structured instead in terms of the problems or difficulties that these innovative systems help to solve in processes engineering by taking advantage of the unique advantages of these systems such as greenness, solubility enhancement, and pressure-tunable properties, allowing for overcoming issues concerning monophasic systems that the chemical engineer is confronted with when scCO 2 or a green solvent are used separately and that have limited their utilization at industrial scales. Among such issues, one can cite (1) difficulties in the solubilization of these compounds, (2) difficult separation of reactants, products, and catalysts, and (3) loss of the catalyst. These problems arise on one hand from the poor solvent power of scCO 2 when used in homogeneous phase and on another hand from the need for a decrease in the usage of distillation as a separation technique. However, their association in biphasic systems allows for overcoming these problems and provides unique opportunities and perspectives to develop future versatile, flexible, and atom economical chemical processes in full accordance with the principles of green sustainable engineering. The green solvents considered in this perspective paper are water, ionic liquids, biobased ionic liquids, and other green solvents such as glycerol and liquid polymers. Ionic liquids have been considered in this paper as they have been claimed as "green" because they allow the prevention of volatile emissions; however, some of them present toxic issues together with a high environmental impact because of their nonbiodegradability and high manufacturing costs. 1 We have then tried to attract special attention to biosourced ionic liquids that may have better toxicological and environmental properties and that may hold promise for their future use in chemical processes. This paper presents also the studies concerning phase equilibrium between scCO 2 and green solvents where biphasic systems can be obtained, as phase behavior control is an interesting tool for designing effective catalytic reactions and catalyst-product separation processes. The unique properties of green solvents that have been proposed as a homogeneous phase in previous studies have prompted us to include them in this perspective paper with the aim of interesting the scientific community in testing them in biphasic systems including scCO 2. Finally, some reflections about the next steps toward greener processes using scCO 2 /green solvent biphasic systems are prese...

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Section: Solubility Of Catalystsmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

ScCO₂/Green Solvents: Biphasic Promising Systems for Cleaner Chemicals Manufacturing

Medina-González

Camy

Condoret

2014

ACS Sustainable Chem. Eng.

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“…Comparison of Different Catalysts. Our previous experience 8, 13,14 and the literature 15 suggest that zeolites perform better than ion exchange resin catalyst for many hydrations. However, we have observed that Amberlyst-15 and Indion-130 are the best among all catalysts, with selectivity toward cydecanol more than 95% at the conversion on the order of 4%.…”

Section: Catalyst Reusabilitymentioning

confidence: 91%

Hydration of Dicyclopentadiene in the Presence of Cation Exchange Resin

Talwalkar

Kumbhar

Mahajani

2006

Ind. Eng. Chem. Res.

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In the present work the hydration of dicyclopentadiene (DCPD) has been studied in the presence of cation exchange resin catalyst. Ion exchange resin Amberlyst-15 was found to offer the best performance with more than 95% selectivity toward cydecanol and conversion as high as 15%. The literature suggests that the zeolites are more active than ion exchange resin catalysts for such reactions. However, this is one of those few liquid phase hydrations for which ion exchange resins offer much better performance in terms of both rate and selectivity toward alcohol. An important finding of our earlier study on this reaction is that the properties of the ion exchange resin catalyst are modified during the course of reaction, which helps in improving the reaction kinetics. In the present work, the kinetic studies have been discussed in detail and issues such as catalyst reusability and reasons for the rate enhancement have been addressed.

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“…The deactivation mechanism of the catalysts might be attributed to the solubility or the washdown of structurally different HPAs from the support surface 17 and thermal aging and dissolution of sulfonic acid groups from ion exchange resins and their subsequent deactivation. 25,26 Fig. 4 Conversion vs. time data for H 3 PW 12 O 40 loadings over S100-H + catalyst, at 343 K, 1:1 reactant molar ratio and 1 wt% catalyst concentration with respect to bare resin and the homogeneous reaction.…”

Section: Catalytic Activity Of Bulk and Supported Heteropoly Acid Cat...mentioning

confidence: 99%

Production of lactic acid esters catalyzed by heteropoly acid supported over ion-exchange resins

2003

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The heterogeneous liquid-phase esterification reaction of lactic acid with ethyl alcohol accompanied with lactoyllactic acid hydrolysis over heteropoly acid supported on ion exchange resin catalysts was investigated at 343 K with ethanol to lactic acid molar ratio of 1:1. The catalysts with 5-20% of tungstophosphoric (H 3 PW 12 O 40 •xH 2 O) and molybdophosphoric (H 3 PMo 12 O 40 •xH 2 O) acid type of heteropoly acids over Lewatit ® S100 showed higher activities than the resin itself. DRIFTS and XRD analysis indicated the formation of amorphous heteropoly acid layer, which is strongly bonded to the resin surface with hydrate structure. Reaction experiments showed molybdophosphoric acid has slightly higher activity than the tungstophosphoric acid, which yields slower deactivation. The reaction model was established by considering the hydrolysis reaction of lactoyllactic acid under the reaction conditions and the esterification step. Reaction rate constants for homogeneous self catalyzed, ion exchange resin catalyzed, and kinetic contribution of heteropoly acid loading were calculated. Kinetic analysis of the reaction data revealed that the active proton sites do not increase proportionally with the amount of heteropoly acids over the resin surface and proton efficiency of the catalysts decreases with increasing loading. It was observed that molybdophosphoric acid loaded S100 catalysts have higher proton efficiency than the tungstophosphoric acid loaded counterpart. Green ContextLactate esters show promise as green solvents, but the esterification of lactic acid can be difficult. This contribution investigates the process, and proposes a resin-supported heteropolyacid as a suitable strongly acidic catalyst for the synthesis of these products in very good yield.

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Extractive hydration of n-butene with solid acid catalysts in the liquid phase and under supercritical conditions

Cited by 9 publications

References 14 publications

ScCO₂/Green Solvents: Biphasic Promising Systems for Cleaner Chemicals Manufacturing

ScCO₂/Green Solvents: Biphasic Promising Systems for Cleaner Chemicals Manufacturing

Hydration of Dicyclopentadiene in the Presence of Cation Exchange Resin

Production of lactic acid esters catalyzed by heteropoly acid supported over ion-exchange resins

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Extractive hydration of n-butene with solid acid catalysts in the liquid phase and under supercritical conditions

Cited by 9 publications

References 14 publications

ScCO2/Green Solvents: Biphasic Promising Systems for Cleaner Chemicals Manufacturing

ScCO2/Green Solvents: Biphasic Promising Systems for Cleaner Chemicals Manufacturing

Hydration of Dicyclopentadiene in the Presence of Cation Exchange Resin

Production of lactic acid esters catalyzed by heteropoly acid supported over ion-exchange resins

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Product

Resources

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ScCO₂/Green Solvents: Biphasic Promising Systems for Cleaner Chemicals Manufacturing

ScCO₂/Green Solvents: Biphasic Promising Systems for Cleaner Chemicals Manufacturing