Anisole hydrolysis in high temperature water

Natalie A. Rebacz, Phillip E. Savage

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

We investigated the hydrolysis of anisole to phenol in high-temperature water with and without water-tolerant Lewis acid catalysis. With no catalyst present, anisole hydrolyzes to phenol in 97% yield after 24 hours at 365 °C, our experimentally determined optimal temperature and time. Experiments with varied water density and analysis of comparable literature data suggest that anisole hydrolysis is almost third order in water, when the SN2 mechanism dominates. Of the water-tolerant Lewis acid catalysts studied, In(OTf)3 offered the best phenol yield. Anisole hydrolysis was first order in catalyst and first order in substrate. Introducing In(OTf)3 catalysis lowered the activation energy for anisole hydrolysis to 31 ± 1 kcal mol-1. Anisole hydrolysis in high-temperature water with In(OTf)3 catalysis is competitive with other techniques in the literature based on rate and yield. In the presence of 5 mol% In(OTf) 3 catalyst, anisole hydrolyzes to phenol in 97% yield after 90 minutes at 300 °C. This journal is

Original languageEnglish (US)
Pages (from-to)3562-3569
Number of pages8
JournalPhysical Chemistry Chemical Physics
Volume15
Issue number10
DOIs
StatePublished - Mar 14 2013

Fingerprint

anisole
hydrolysis
Hydrolysis
Phenol
Water
phenols
water
Catalysis
catalysis
catalysts
Lewis Acids
Catalysts
Temperature
acids
Activation energy
activation energy
trifluoromethanesulfonic acid
Substrates

All Science Journal Classification (ASJC) codes

  • Physics and Astronomy(all)
  • Physical and Theoretical Chemistry

Cite this

Rebacz, Natalie A. ; Savage, Phillip E. / Anisole hydrolysis in high temperature water. In: Physical Chemistry Chemical Physics. 2013 ; Vol. 15, No. 10. pp. 3562-3569.
@article{8cf1f6a48f644230bd909fbfac3d1ae1,
title = "Anisole hydrolysis in high temperature water",
abstract = "We investigated the hydrolysis of anisole to phenol in high-temperature water with and without water-tolerant Lewis acid catalysis. With no catalyst present, anisole hydrolyzes to phenol in 97{\%} yield after 24 hours at 365 °C, our experimentally determined optimal temperature and time. Experiments with varied water density and analysis of comparable literature data suggest that anisole hydrolysis is almost third order in water, when the SN2 mechanism dominates. Of the water-tolerant Lewis acid catalysts studied, In(OTf)3 offered the best phenol yield. Anisole hydrolysis was first order in catalyst and first order in substrate. Introducing In(OTf)3 catalysis lowered the activation energy for anisole hydrolysis to 31 ± 1 kcal mol-1. Anisole hydrolysis in high-temperature water with In(OTf)3 catalysis is competitive with other techniques in the literature based on rate and yield. In the presence of 5 mol{\%} In(OTf) 3 catalyst, anisole hydrolyzes to phenol in 97{\%} yield after 90 minutes at 300 °C. This journal is",
author = "Rebacz, {Natalie A.} and Savage, {Phillip E.}",
year = "2013",
month = "3",
day = "14",
doi = "10.1039/c3cp43877e",
language = "English (US)",
volume = "15",
pages = "3562--3569",
journal = "Physical Chemistry Chemical Physics",
issn = "1463-9076",
publisher = "Royal Society of Chemistry",
number = "10",

}

Anisole hydrolysis in high temperature water. / Rebacz, Natalie A.; Savage, Phillip E.

In: Physical Chemistry Chemical Physics, Vol. 15, No. 10, 14.03.2013, p. 3562-3569.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Anisole hydrolysis in high temperature water

AU - Rebacz, Natalie A.

AU - Savage, Phillip E.

PY - 2013/3/14

Y1 - 2013/3/14

N2 - We investigated the hydrolysis of anisole to phenol in high-temperature water with and without water-tolerant Lewis acid catalysis. With no catalyst present, anisole hydrolyzes to phenol in 97% yield after 24 hours at 365 °C, our experimentally determined optimal temperature and time. Experiments with varied water density and analysis of comparable literature data suggest that anisole hydrolysis is almost third order in water, when the SN2 mechanism dominates. Of the water-tolerant Lewis acid catalysts studied, In(OTf)3 offered the best phenol yield. Anisole hydrolysis was first order in catalyst and first order in substrate. Introducing In(OTf)3 catalysis lowered the activation energy for anisole hydrolysis to 31 ± 1 kcal mol-1. Anisole hydrolysis in high-temperature water with In(OTf)3 catalysis is competitive with other techniques in the literature based on rate and yield. In the presence of 5 mol% In(OTf) 3 catalyst, anisole hydrolyzes to phenol in 97% yield after 90 minutes at 300 °C. This journal is

AB - We investigated the hydrolysis of anisole to phenol in high-temperature water with and without water-tolerant Lewis acid catalysis. With no catalyst present, anisole hydrolyzes to phenol in 97% yield after 24 hours at 365 °C, our experimentally determined optimal temperature and time. Experiments with varied water density and analysis of comparable literature data suggest that anisole hydrolysis is almost third order in water, when the SN2 mechanism dominates. Of the water-tolerant Lewis acid catalysts studied, In(OTf)3 offered the best phenol yield. Anisole hydrolysis was first order in catalyst and first order in substrate. Introducing In(OTf)3 catalysis lowered the activation energy for anisole hydrolysis to 31 ± 1 kcal mol-1. Anisole hydrolysis in high-temperature water with In(OTf)3 catalysis is competitive with other techniques in the literature based on rate and yield. In the presence of 5 mol% In(OTf) 3 catalyst, anisole hydrolyzes to phenol in 97% yield after 90 minutes at 300 °C. This journal is

UR - http://www.scopus.com/inward/record.url?scp=84874088642&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84874088642&partnerID=8YFLogxK

U2 - 10.1039/c3cp43877e

DO - 10.1039/c3cp43877e

M3 - Article

VL - 15

SP - 3562

EP - 3569

JO - Physical Chemistry Chemical Physics

JF - Physical Chemistry Chemical Physics

SN - 1463-9076

IS - 10

ER -