Aerobic Oxidations in Continuous Flow

Chapter
Part of the Topics in Organometallic Chemistry book series (TOPORGAN, volume 57)

Abstract

In recent years, the high demand for sustainable processes resulted in the development of highly attractive oxidation protocols utilizing molecular oxygen or even air instead of more uneconomic and often toxic reagents. The application of these sustainable, gaseous oxidants in conventional batch reactors is often associated with severe safety risks and process challenges especially on larger scales. Continuous flow technology offers the possibility to minimize these safety hazards and concurrently allows working in high-temperature/high-pressure regimes to access highly efficient oxidation protocols. This review article critically discusses recent literature examples of flow methodologies for selective aerobic oxidations of organic compounds. Several technologies and reactor designs for biphasic gas/liquid as well as supercritical reaction media are presented in detail.

Keywords

Aerobic oxidation Continuous flow Heterogeneous catalysis Homogeneous catalysis Oxygen 

Abbreviations

Ac

Acetyl

acac

Acetylacetonate

ATR

Attenuated total reflection

bpy

2,2′-Bipyridyl

conv

Conversion

CSTR

Continuous stirred-tank reactor

DBU

1,8-Diazabicyclo[5.4.0]undec-7-ene

DMF

N,N-dimethylformamide

DMSO

Dimethylsulfoxide

dr

Diastereomeric ratio

equiv

Equivalent(s)

Et

Ethyl

EXAFS

Extended X-ray absorption fine structure

FDH

Formate dehydrogenase

FEP

Fluorinated ethylene propylene

g

Gram(s)

GC

Gas chromatography

h

Hour(s)

HbpA

2-Hydroxybiphenyl 3-monooxygenase

HPLC

High-performance liquid chromatography

IBX

2-Iodoxybenzoic acid

i-Pr

iso-Propyl

IR

Infrared

L

Liter(s)

LED

Light-emitting diode

LOC

Limiting oxygen concentration

m

Meter(s)

M

Molar

Me

Methyl

MFC

Mass flow controller

min

Minute(s)

mol

Mole(s)

MS

Mass spectrometry

NAD

Nicotinamide adenine dinucleotide

NaHMDS

Sodium hexamethyldisilazide

NMI

N-Methylimidazole

NMO

N-Methylmorpholine N-oxide

NMP

N-Methyl-2-pyrrolidone

n-Pr

n-Propyl

PCC

Pyridiniumchlorochromate

PDC

Pyridinium dichromate

PDMS

Polydimethylsiloxane

PEEK

Polyether ether ketone

PEG

Polyethylene glycol

PFA

Perfluoroalkoxy

Ph

Phenyl

phen

Phenanthroline

PTFE

Polytetrafluoroethylene

quant

Quantitative

rt

Room temperature

s

Second(s)

sc

Supercritical

Sel

Selectivity

SET

Single-electron transfer

SMU

Static mixing unit

t-AmOK

Potassium tert-amylate

TBAF

Tetrabutylammonium fluoride

TBR

Trickle-bed reactor

t-bu

tert-Butyl

TEM

Transmission electron microscopy

TEMPO

(2,2,6,6-Tetramethylpiperidin-1-yl)oxyl

TEOS

Tetraethoxysilane

Tf

Trifluoromethanesulfonyl

TFA

Trifluoroacetic acid

THF

Tetrahydrofuran

TMEDA

N,N,N′,N′-Tetramethyl-1,2-ethylenediamine

TMSCN

Trimethylsilylcyanide

TPAP

Tetrapropylammoniumperuthenate

TPP

meso-Tetraphenylporphyrin

U

Unit(s)

UHP

Urea hydrogen peroxide

XAS

X-ray absorption spectroscopy

Notes

Acknowledgments

Research on continuous flow chemistry in our laboratories over the past decade has been generously supported by the Christian Doppler Research Association (CDG) and a variety of industrial partners including Lonza, DPx, Microinnova, ThalesNano, Anton Paar, Eli Lilly, Bayer Pharma, BASF, and Clariant.

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Copyright information

© Springer International Publishing Switzerland 2015

Authors and Affiliations

  1. 1.Institute of ChemistryUniversity of Graz, NAWI GrazGrazAustria

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