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Hydrogenation of 4-chloronitrobenzenes over palladium and platinum catalysts supported on beta zeolite and γ-alumina

  • Milan Králik
  • Dana Gašparovičová
  • Mária Turáková
  • Zuzana Vallušová
  • Jozef Balko
  • Peter Major
  • Milan Kučera
  • Pavel Puliš
  • Ondrej Milkovič
Original Paper
  • 25 Downloads

Abstract

Liquid-phase hydrogenation of 4-chloronitrobenzene (4-CNB) to 4-chloroaniline (4-CAN) under mild reaction conditions (0.6 MPa, 25 °C, methanol-diethyl ether, 1:1 vol.) over palladium and platinum catalysts containing 1 mass% of metal supported on beta zeolite (M/B) or γ-alumina (M/A) was studied. The catalysts were prepared by the incipient wetness method using amino nitrate complexes and hydrogen as the reducing agent. SEM, adsorption–desorption nitrogen isotherms, XRD, TEM, and hydrogen chemisorption techniques were used for their characterization. The techniques employed revealed the presence of relatively large metal particles (approximately 15 nm; about 3% of metal dispersion). Stability of the catalysts during the hydrogenation was high; no catalyst changes were observed after two recycle runs. Hydrogenation over M/A catalysts was found to be faster than that over M/B catalysts in the methanol–diethyl ether mixture. Selectivity of only about 75% to 4-CAN was achieved over the M/A catalyst in methanol. Positive effect of the acid support (beta zeolite) and low polarity of the reaction environment (diethyl ether) are reflected in the high selectivity to 4-CAN; of about 99% at virtually 100% conversion of 4-CNB.

Keywords

Hydrogenation Liquid phase Chloronitrobenzenes Hydrodechlorination Palladium catalysts Platinum catalysts Solvent effect 

Abbreviations

AC

Activated carbon

Al-PILC

Al-pillared clay

AN

Aniline

ASMA

Amino poly[styrene-co-maleic anhydride]

B

Benzene

BET

Brunauer, Emmet, and Teller

4-CAN

4-Chloroaniline

CHAN

Cyclohexane

ClPhNO

Chloronitrosobenzene

ClPhHNOH

N-chloro-phenylhydroxylamine

CN

Carbon nitride

4-CNB

4-Chloronitrobenzene

CNT

Carbon nanotubes

DABP

4,4′-Diaminobiphenyl

DETE

Diethyl ether

DMF

Dimethylformamide

DR

Dubinin–Radushkevich

DOX

1,4-Dioxane

EG

Ethylene glycol

EtOAc

Ethyl acetate

EtOH

Ethanol

FTIR

Fourier-transform infrared spectroscopy

GO

Graphite oxide

HDC

Hydrodechlorination

HDN

Hydrodenitrogenation

HPLC

High-performance liquid chromatography

M/A

1 mass% of metal supported on γ-alumina

M/B

1 mass% of metal supported on beta zeolite

MeOH

Methanol

MC

Mesoporous carbon

MS

Mesoporous silica

NB

Nitrobenzene

NTO

Nitrotoluene

NAN

Nitroaniline

NAS

Nitroanisole

NMR

Nuclear magnetic resonance

NTs

Nanotubes

Rec.

Number of repetitions with the same catalyst

SAED

Selective electron diffraction

SEM

Scanning electron microscopy

TEM

Transmission electron microscopy

THF

Tetrahydrofurane

TMB

Trimethylbenzene

TOFH2

Turn over frequencies (molH2 mol metal −1 s−1)

TOFs,H2

Turn over frequencies with respect to the metal surface (molH2 m−2 s−1)

Tol

Toluene

TPD

Temperature-programmed desorption

W

Water

XRD

X-ray diffraction

XPS

X-ray photoelectron spectroscopy

List of symbols

C

coefficient in the BET isotherm

d

Average size of metal particles (nm)

dH2,CHS

Average size of metal particles estimated from H2 sorption (nm)

dTEM

Average size of metal particles estimated from TEM (nm)

ds,TEM

Average size of metal particles estimated from TEM with respect to the surface (nm)

dV,TEM

Average size of metal particles estimated from TEM with respect to the volume (nm)

dXRD

Average size of metal particles estimated from XRD (nm)

DM

Dispersion of metal (%)

Dhkl

Lattice parameter (nm)

fH2,M

Factor expressing number of metal atoms interacting with hydrogen molecule

K

The Scherrer’s constant (usually 0.9)

mcat

Mass of a catalyst (g)

nCNB,0

Moles of x-CNB in the starting reaction mixture (mol)

nCNB,t

Moles of x-CNB in the reaction mixture at time t (mol)

nH2,Chs

Moles of H2 chemisorbed on catalyst sample (mol g−1)

nH2,r

Moles of H2 consumed in the hydrogenation process (mol)

nY

Moles of component “Y” in the reaction mixture (mol)

P

Polarity of a solvent (Pwater = 100)

sM

Specific surface of metal particles (m2 g−1)

sA,M

Surface equivalent of one metal atom (m2)

SY

Selectivity to compound “Y” (%)

t

Time (s)

TFP

Flash point temperature (°C)

TAI

Autoignition temperature (°C)

va

Adsorbed amount expressed in the liquefied form (cm3 g−1)

Vmi

Volume of micropores (cm3 g−1)

wM

Content of the metal in the dry catalyst (wt%)

x

Relative pressure (x = p/ps)

xH2,25°C

Mole fraction of H2 at 25 °C and 101.325 kPa

XCNB

Conversion of chloronitrobenzene (%)

Greek letters

εr

Relative permittivity (dielectric constant)

ΔM

Loose of the metal content as a portion of the initial amount of metal (%)

δ

Solubility parameter

\(\overline{\delta }\)

Average error

λ

Wavelength of the X-ray used for the XRD (nm)

ρ

Density (kg m−3)

η

Dynamic viscosity (cP)

μ

Dipole moment (D)

Notes

Acknowledgements

This publication is a result of the project implementation: Hydrogenation in the Liquid Phase, ITMS: 26,220,220,144, supported by the Research & Development Operational Programme funded by the ERDF.

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Copyright information

© Institute of Chemistry, Slovak Academy of Sciences 2018

Authors and Affiliations

  1. 1.Institute of Organic Chemistry, Catalysis and PetrochemistrySlovak University of Technology in BratislavaBratislavaSlovakia
  2. 2.VUCHT a.s, Areal Duslo a.sŠaľaSlovakia
  3. 3.SLOVNAFT, a.sBratislavaSlovakia
  4. 4.Faculty of MetallurgyTechnical University of KošiceKošiceSlovakia

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