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Related Concept Videos

Leveling Effect01:29

Leveling Effect

1.6K
In acid-base chemistry, the leveling effect refers to the limitation imposed by the solvent on the strength of acids and bases in solution. When a base stronger than the solvent's conjugate base is used, it deprotonates the solvent until the base is entirely consumed, making it ineffective against weaker acids. Conversely, an acid stronger than the solvent's conjugate acid protonates the solvent until the acid is depleted, rendering it ineffective against weaker bases. Essentially, the...
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Leveling Effect and Non-Aqueous Acid-Base Solutions02:11

Leveling Effect and Non-Aqueous Acid-Base Solutions

8.2K
This lesson defines the leveling effect in acidic and basic solutions and its role in aqueous and non-aqueous solutions. It is essential to understand the competing nature of various species in a chemical system.
The Leveling Effect of a Solvent
A generic acid (HA) reacts with the generic base (B-) to yield the corresponding conjugate base (A-) and conjugate acid (HB):
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Acid-Catalyzed Hydration of Alkenes02:45

Acid-Catalyzed Hydration of Alkenes

15.3K
Alkenes react with water in the presence of an acid to form an alcohol. In the absence of acid, hydration of alkenes does not occur at a significant rate, and the acid is not consumed in the reaction. Therefore, alkene hydration is an acid-catalyzed reaction.
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Solvating Effects02:12

Solvating Effects

7.8K
An understanding of the solvating effect helps rationalize the relation between solvation and acidity of the compound. In addition, this also explains the relative stability of conjugate bases for compounds with different pKa values. This lesson details, in-depth, the principle of solvating effects. The strength of an acid and the stability of its corresponding conjugate base are determined using pKa values. This observed relationship is a consequence of solvation, which is the interaction...
7.8K
Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis01:13

Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis

3.1K
Hydrolysis of esters under acidic conditions proceeds through a nucleophilic acyl substitution. In the presence of excess water, the reaction proceeds in a reversible manner, forming carboxylic acids and alcohols.
During hydrolysis, the ester is first activated towards nucleophilic attack through the protonation of the carboxyl oxygen atom by the acid catalyst. The protonation makes the ester carbonyl carbon more electrophilic. In the next step, water acts as a nucleophile and adds to the...
3.1K
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview01:20

Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview

15.1K
The Fischer esterification reaction was developed by the German chemist Emil Fischer in 1895. It is a condensation reaction between carboxylic acids and alcohols in an acidic medium to give esters and water.
15.1K

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Solvent effects in acid-catalyzed biomass conversion reactions.

Max A Mellmer1, Canan Sener, Jean Marcel R Gallo

  • 1Department of Chemical and Biological Engineering, University of Wisconsin-Madison, Madison, WI 53706 (USA).

Angewandte Chemie (International Ed. in English)
|September 13, 2014
PubMed
Summary

Polar aprotic solvents like gamma-valerolactone (GVL) accelerate acid-catalyzed reactions such as xylose to furfural conversion. These solvents enhance reaction rates and selectivity by altering proton stabilization in transition states.

Keywords:
biomasscatalysiskineticssolvent effectssustainable chemistry

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Area of Science:

  • Chemical kinetics
  • Catalysis
  • Organic chemistry

Background:

  • Acid-catalyzed conversion of biomass-derived carbohydrates is crucial for biorefineries.
  • Understanding solvent effects on reaction kinetics is key to process optimization.
  • Polar aprotic solvents may offer advantages over water in biomass conversion.

Purpose of the Study:

  • To investigate the kinetic effects of polar aprotic solvents on acid-catalyzed reactions.
  • To quantify the influence of gamma-valerolactone (GVL) on xylose conversion to furfural.
  • To explore the role of solvent properties in Brønsted acid catalysis.

Main Methods:

  • Kinetic studies of xylose to furfural conversion.
  • Analysis of dehydration and hydrolysis reactions using various acid catalysts.
  • Comparison of reaction rates in water versus GVL and other polar aprotic solvents.
  • Investigation using homogeneous Brønsted acids with different pKa values.

Main Results:

  • Gamma-valerolactone (GVL) significantly increases reaction rates and product selectivity for xylose to furfural conversion compared to water.
  • GVL demonstrates similar rate-enhancing effects on the dehydration of 1,2-propanediol and the hydrolysis of cellobiose.
  • The observed kinetic effects are consistent across homogeneous and solid Brønsted acid catalysts (e.g., H-mordenite, H-beta).

Conclusions:

  • Polar aprotic solvents, particularly GVL, enhance acid-catalyzed reaction kinetics.
  • Solvent influence on reaction rates is attributed to altered stabilization of the acidic proton and transition states.
  • GVL is a promising solvent for biomass conversion processes requiring acid catalysis.