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CHAPTER 7

OXIDATION OF NAPHTHALENE

Abstract
Polycyclic aromatic hydrocarbons are carcinogenic substances to
which humans are exposed from the environment. The major exhausts of the

diesel vehicles are particulates and polycyclic aromatic hydrocarbons, which

are emitted from diesel engines and can be much higher than those of Otto
engines. Naphthalene, a constituent of diesel and jet fuel is the most volatile

member of this class of pollutants. The industrial productioz of naphthalene

and its application as an intermediate can contribute to the environmental

naphthalene burden, it is widely accepted that the major part comes from

burning processes such as residential, industrial and natural sources.


Common methods applicable for naphthalene elimination from the waste
stream include biodegradation, adsorption, absorption, high-energy electron
beam, ozonization and catalytic oxidation. Among them, the catalytic oxidation

has been demonstrated as one of the cost eective and eicient technologies to
destroy the troublesome volatile organic compounds.

Oxidation of Naphthalene

7.1 INTRODUCTION

Polycyclic aromatic compounds (PACs) have been found special

concern because these are among the most toxic pollutants and can be
transported by small particles deep into human hngs. Therefore, it is desired

that new formulations of metal-based catalysts, which are effective in


controlling NOX problems, be utilized to satisfactorily mitigate PACs toxicity

in diesel emissions. Naphthalene (Nap) consists of a basic aromatic structure


and is the simplest and least toxic poly aromatic hydrocarbon. It is one of the

most stable tar compounds and it is difcult to decomposel. The oxidation


reaction pathways are depicted in Scheme 7.1.
OH
0H

\ [O]

/ 1-Naphthol --in
[O]

Naphthalene OH \
2-Naphthol [O1 I

Oo
o ---

Phthalic anhydridc 1,4-Naphhaquin0n


Scheme .7.1

In the last decade certain success has been achieved in the resolution of

oxidation of aromatic compounds in nuclei. The main product of naphthalene

oxidation is phthalic anhydride (PAN). Generally phthalic anhydride


253

Chapter 7 g
production is by catalytic oxidation of 0-xylene or naphthalene using V205
operated at 340 to 385 C2. Of the current production of phthalic anhydride

obtained by naphthalene and 0-xylene oxidation, 50 percent is used for


plasticizers, 25 percent for alkyl resins, 20 percent for unsaturated polyester
resins, and 5 percent for miscellaneous and exports. Because emission factors

are intended for future as well as present application, utilization of highly


carcinogenic feedstock naphthalene for phthalic anhydride production is very
desirable.

Several groups investigated the activities of metal catalysts in


decomposing naphthalene. Decomposition of naphthalene with O; is reported
by Zhang et al.3 over supported catalysts like Pt, Pd, Ru, Co, Mo and W on 7

A1203. Xiao et al.4 investigated the intermediates generated during catalytic


oxidation of naphthalene over l%Pt/y-A1203 and 5%Co/7-A1203 catalysts and

were identied as naphthalene-decomposed by-products, naphthalene


derivatives, and polymerized PACs. They also conclude that the weaker
adsorption on Co catalysts allowed more direct and complete oxidation of
naphthalene. Other catalysts, which have been utilized to oxidize polyaromatic

hydrocarbons including volatile organic compounds, are Pt/ALMCM-41,


V205-WO3fl"iO;, Fe2O3 and M003-V205, Pd-Ce/A1203, Pd-Ba/A1103 and Pd

Zr/Y zeolites '12. Li et al. studied the inuence of Pt on catalytic activity of


Ni/A1203 by using naphthalene as a model compound . Cr(V I) oxide catalyzed

oxidation of arenes with periodic acid as the tenninal oxidant in acetonitrile

produced quinine as the main product and naphthalene was oxidized to 1,4

naphthaquinonem. The effect of protic and aprotic solvents on naphthalene


oxidation over cytochrome P-450 was studied by Safari et al.15 and reported a
254

Oxidation of Naphthalene

mechanism based upon the electrophilic addition with a carbocation


intennediate which is consistent with peroxo iron intermediate. The formation

of phthalic anhydride by further oxidation of 1,4-dihydroxy naphthalene from


1-naphthol was observed on mesoporous vanadosilicates. The active sites were

the tetrahedral vanadium sites inside the pore channels of MCM-4116. The

steam reforming of naphthalene have been studied over Ni and Co/MgO


catalysts, in which Co/MgO catalyst pre calcined at 873 K exhibited the best
performancel MO.

This chapter deals with the oxidation of naphthalene in order to develop

an abatement technique of polyaromatic hydrocarbons emitted into the


atmosphere. The relationship between conversion efficiency, operating
parameters and relevant factors such as treatment temperatures, catalyst
weight, solvent effect and oxidant volume etc are examined in detail.
7.2 INFLUENCE OF REACTION CONDITION

The inuence of reaction condition was analyzed in order to maximize

the product yield and selectivity. Influence of reaction parameters on


naphthalene oxidation with H202 was initially studied in nonoptimized
conditions with 8VC as the catalyst.

7.2.1 Effect of Temperature

The effect of temperature on naphthalene oxidation was studied by


varying the temperature between 298 and 373 K while other parameters were
kept constant. Results are presented in Figure 7.1.

255

Chapter 7

so - 1- so

-"Naphthalene --A-Phthalicanhydridc 1

I
l

- f-20 ?

01 e re *i " 1 I ~e+0

298 323 333 353 373


Temperature/K

Figure 7.1

Reaction conditions:-8VC-100 mg, Naphthalene-1.56 mmol,


Acetonitrile- 191 mmol, H20; -44 mmol and Time-4 h.

Temperature variation on naphthalene oxidation shows that as the

temperature increases from room temperature conversion and phthalic


anhydride selectivity increases reaches a maximum and then decrease. At 333

K, a maximum conversion (63.5 %) with high phthalic anhydride selectivity


(79 /go) is observed. Further increase in reaction temperature cause decrease in

conversion as well as phthalic anhydride selectivity. Low activity is attributed

to the competitive thennal decomposition of H20; at higher temperatures


without being involved in the reaction.

7.2.2 Effect of Solvent

The oxidation activity of" the catalyst obtained for a series of solvents
with different polarities is depicted in Figure 7.2.

256

Oxidation of Naphthalene

50
'
'
100
T
40- +80 l
'-I-Naphthalene A Phthalic anhydride

Ip AJBic -_
0

/-\
\-/
00-1

-4-I.

0 '1 U _%' ~~1 | Jr Q

I Solvent/mm 01

l A-Water, B-Dichloromethane, C-Acetone, D-Acetonitrile

I is

Figure 7.2

Reaction conditions:- 8VC-100 mg, Naphthalene-1.56 mmol, Solvent


-191 ml, H20; -44 mmol, Temperature- 333 K and Time-2 h.

The reacfon media have a strong inuence on the activity of the


catalyst. Absence of any solvent didnt activate the reaction. Water was
inactive in the oxidation. Acetone and acetonitrile acts positively giving
phthalic anhydride as the main product. The enhanced activity and selectivity
of the catalysts in acetonitrile can be explained on the basis of polarity of these

solvents. In organic solvent the reaction is initiated by electron transfer at the

interface leading to the radical cation of the substrate and superoxide anion

while in the aqueous solution, the actual active species are assumed to be
hydroxyl radicals formed by oxidation of solvent2223. Acetonitrile is an aprotic

solvent. The activity of the catalysts is found to increase with the solvent
polarity and acetonitrile having more polar nature always enhances the activity.

In this solvent, the phase separation between the aromatic substrate and the
aqueous oxidant is greatly decreased thereby allows an easy transport of the

active oxygen species for the oxidation. According to Federica et a1.25 the
257

Chapter 7

oxidation of naphthalene in acetonitrile gave only traces of dialdehydes with

signicant amount of 1,4-naphthaquinone (Napqone) and the main product

l llll

was phthalic anhydride.

7.2.3 Effect of Catalyst weight

The inuence of amount of the catalyst on the naphthalene oxidation is


presented in Figure 7.3.

Ti
** J fl ii: T T:
J J i if :anhydride
; i: f f T
A -I-Naphthalene
"0-Phthalic

M
I00-H
_ H-80
/R
so-U
l 7\

\ l F60 A l

y 2014
W
...ll
l iW
ll-20
I-4

1H
or ::F=-ii: = w>; Q-0
00-r:so
100 150 200

l Catalyst weight/mg J1
Figure 7.3

Reaction conditions:-8VC, Naphthalene-1.56 mrnol, Acetonitrile


191 mmol, H302 -44 mmol, Temperature ~333 K and Time-2 h.

Absence of catalyst resulted no oxidation. As the amount of catalyst

increases, an increase in the activity and phthalic anhydride selectivity was


noted to a certain extent and decreased with a further increase in the catalyst

amount. Very high concentration of catalyst amount can inhibit the


autooxidation reactions, which in turn results in lower activity with
nonselective products26.

258

Oxidation of Naphthalene

IJi n
F
;I

7.2.4 Effect of Acetonitrile volume

The effect of concentration of the acetonitrile on naphthalene oxidation


is shown in Figure 7.4.

L 80 " "' 80
I

T
'
L60
I W a __
-I-Naphthalene -9-Phihalic anhydridc

"20

0-|95~191
e - 286
J 381
e-0 1;

Volume/mmol

Figure 7.4

Reaction conditions:- SVC-100 mg, Temperature-333 K,


Naphthalene-1.56 mmol, H202 -44 mmol and Time-2 h.

Taking different volumes of solvent while keeping other parameters


constant, inuence of solvent concentration on oxidation reaction was tested.

The conversion increased with increase in acetonitrile volume and reaches a

maximum value and then decreases thereafter. Too much of acetonitrile


concentration reduces conversion as well as acetophenone selectivity. The
acetonitrile with the concentration of 191 mmol was thus found to be optimum.

When the solvent was excess, the benzene or catalyst concentration at the

interface may be lower, thus resulting in a decreased conversion rate and


nonselective oxidation of alcohols fonned27.

259

Chapter 7

r\
-|

7.2.5 Effect of Naphthalene volume

The effect of volume of naphthalene dining oxidation is shown in


Figure 7.5.

14-so
5
O | 1%
T M If I-Naphthalene -Q-Phthalilclanl1ydn'dc

1l 3,"-4
-_2;.
Q
n-
kI
r\._

' \?

gir"
0.78---4
1.56 |
2.34 3 r12Q)

Volume/mmol

Figure 7.5

Reaction conditions:~ 8VC-100 mg, Temperature-333 K,


Acetonitrile-95 mmol, H202 - 44 mmol and Time-4 h.

Polarity of the reactant and products formed play an important role in


the oxidation of naphthalene. The substrate naphthalene is nonpolar while the
primary products formed are polar. An increase in activity and selectivity was

observed to a certain extent and then decreased with further increase in


substrate to catalysts ratio. This could be probably due to the decrease in the

number of active centers for the reaction. Selectivity decline can be due to

further oxidation of phthalic anhydride thus -formed under the reaction


conditionszg .

7.2.6 Effect of H20; volume


The effect of oxidant volume on naphthalene oxidation is illustrated in
Figure 7.6
260

r\ 1
T

Oxidation of Naphthalene

-0

60 ' 30
-I- Naphthalene Phthalic anhydride

1%

hi

Ll

\-ll

-0

1in

' 20+11| 44
a ~19
|r0
Volume/mmol

Figure 7.6

Reaction conditions:- 8VC-100 mg, Acetonitrile-191 mmol,


Naphthalene- 156 mmol, Temperature-333 K and Time-2 h.

No oxidaion takes place in the absence of oxidant. An increase in the


amount of oxidant resulted an increase in rate together with phthalic anhydride

selectivity reaches a maximum and then decrease. This can arise from the
negative effect due to the production of H20 as a byproduct. The water and

oxidant compete for complexation to the vanadium center, therefore excess


water relative to H20; inhibits the reaction. The amount of H202 consumed in

self-decomposition was much more than that consumed in the oxidation

reaction. This may be why more than stoichiometric amount of H20; is


needed30.

7.2.7 Effect of Time

The inuence of reaction time on naphthalene oxidation is illustrated in


Figure 7.6.

261

Chapter 7

i\l50"
-.,
.|_
'
l
l
l
616
W F90I
90-
cl-I

v -I Naphthalene -5-Phthalic anhydride

1% l

3014 * 6
nn

\ Time/h 1
I23456736

l 10-w" ir * -W rm "-T ~* 1;*"i*i** T *c L60 ;

\_ _ __ ___ g___s_ si___t_ _* _g_;


Figure 7.6

Reaction conditions:- Temperature -333 K, 8VC-100 mg, Acetonitrile


191 mrnol, Naphthalene- 156 mmol and H20; -44 mmol.

As observed from the gure, variation of time intert als on reaction


indicated that around 74 % of the conversion was achieved at a time of 6 h,

while further increase in reaction time did not signicantly enhance the
conversion. Phthalic anhydride of about 88 % was obtained selectively in the

initial period of time. Further oxidation of this to acid can cause drop off in
selectivity with time. Similar observation was reported for benzene oxidation

and attributed to the poisoning of the surface sites by the reaction products
which in turn block the active sites with long time of reaction run3 1.
7.3 NAPHTHALENE OXIDATION OVER PREPARED CATALYSTS

The reaction parameters play an important role in determining the

oxidation rate and product selectivity in the liquid-phase oxidation of


naphthalene using hydrogen peroxide as oxidant. The naphthalene oxidation

262

Oxidation of Naphthalene

was carried out over all the prepared catalysts under the selected reaction
conditions as shown in Table 7.1.
Table 7.1

Parameters Selected condition


Temperature/K. 333
Acetonitrile/mmol 191
Naphthalene/mmol 1.56

H202/mmol 44

Time/h 6

Table 7.2 shows the results of naphthalene oxidation over VC series of


catalysts.
Table 7.2

Catalyst Conversion
(

Selectivity (%)

wt. %) PAN

Ce
2VC

1.0

4VC

25.0

73.6

6VC

71.3

86.4

8VC

73.1

89.4

10VC

69.3

90.7

q_
100

2-Naphthol 1,4-Napqone

T7. -;':;:_ _ "1

26.3

7.2 6.4
6.6 3.8
4.2 5.1

The ceria is completely inactive towards naphthalene oxidation under


the reaction conditions studied. Addition of vanadia enhances the activity and

phthalic anhydride selectivity. Conversion increases up to 8VC while it


decreases for l0VC. Phthalic anhydride production was increased with vanadia
263

i#2&e' 7 _

loading. Small amounts of 2-naphthol and 1,4-naphthaquinone were also


observed.

Table 7.3 shows the results of naphthalene oxidation over VCRS series
of catalysts.
Table 7.3

Catalyst

Conversion Selectivity (/ll 7

RS

CRS

(wt.%)

PAN

ZVCRS l .2
4VCRS 25 .9
6VCRS 84.6
SVCRS 89.7
IOVCRS 76.9

1,4-Napqone

100

92.7

7.3

94.5

5.5

96.5

4.0

96.7

3.2

Silica and CRS support gave no oxidation products under the set

reaction conditions. Interestingly, only phthalic anhydride and 1,4


naphthaquinone were obtained with VCRS series of catalysts. Conversion
increased up to 8VCRS and further increase in vanadia loading to 10 wt.%
V205 reduced the conversion rate. However, phthalic anhydride selectivity was
found to be the same with 8 and IOVCRS

Table 7.4 shows the results of naphthalene oxidation over praseodymia


containing catalysts along with various silica supported vanadia catalysts.

Oxidation of Naphthalene
Table 7.4

p
_

PRS
1.3
100

2VP 1.23 - 100

Catalyst Conversion Selectivity (%)

(wt. %) PAN 2-Naphthol 1,4-Napqone

6VP
17.8
100

l0VP 1.2 - 82.4 17.6

ZVPRS

6VPRS

IOVPRS 2.3 - 58.1 41.8

vs
53.6
11.3
88.6
6vRs* 77.9 91.9 - 11.9
6vsG* 78.2 94.7 - 5.3
$-5min,#-4h
Praseodymia catalysts exhibit a very different behaviour during

oxidation of naphthalene. P, 2 and 6VPRS did not respond to the oxidation


reaction under the set conditions. Any of the catalysts of VP and VPRS series

produced no phthalic anhydride during naphthalene oxidation. Among VP


series activity increased with vanadia loading to 6VP and then decreases for

IOVP. 2 and 6 VP produced only 2-naphthol while small amount of 1,4


naphthaquinone was observed with 10VP. IOVPRS produced 2-naphthol and

1,4-naphthaquinone as the oxidation products. V205 (V) oxidized 53.6 %


naphthalene within 5 minutes of reaction and gave 11.3 /6 phthalic anhydride

and 88.6 % 1,4-naphthaquinone. Various silica (6VRS and 6VSG) supported

265

Chapter 7

vanadia catalysts show higher oxidation activity to produce phthalic anhydride


in high amount within 4 h of the reaction.
7.4 EFFECT OF LEACHING

In order to attain a better insight into the catalyst behaviour it is


important to check the heterogeneity during the reaction conditions. Leaching

of active metal sites may occur during reactions and the enhanced catalytic

activity can arise from the presence of such homogeneous leached metal
species. The leaching of vanadium ions under reaction conditions from the

catalysts was veried by carrying out ltrate experiments. After l h of


reaction, the catalyst was ltered off while hot and the ltrate solution was
again used for the reaction without any further addition of the oxidant. Table

7.5 shows the results of leaching studies conducted with representative


catalysts.
Table 7.5

Catalyst Time/h Conversionmi(iwt.%) PAN (%)

8vc

12.6
80.2
Filtiate 1 14.8 81.2

8VCRS I/2 17.6 88.8

Filtrate 1 19.3 89.5

An enhancemem observed for the ltrate reaction indicates some of the


active vanadia sites may leach into the reaction during oxidation condition thus

enhancing the conversion rate. The use of 30 % H20; and acetonitrile as


solvent results considerable leaching in liquid phase reactions. However the
phthalic anhydride selectivity remains more or less the same.
266

Oxidation of Naphthalene

7.5 REGENERATION AND STABILITY

The stability of the catalysts was tested by recycling experiments with


regenerated catalysts. The recycling experiments were carried out as follows.
After 2 h reaction, the catalyst was recovered by hot ltration, washed several
times with acetone, dried at 383 K overnight and calcined for 5 h at 773 K. The

recovered catalysts were reused for naphthalene oxidation under the same
reaction conditions. Table 7.6 displays the results obtained with regenerated
catalysts.
Table 7.6

Catalyst N Cycle Conversion (wt.%) I3 PAN (%)


8VC

8VCRS

1
26.2
82.3
2l 28.7
23.3 95.4
81.2
2 26.4 93.8

The activity of the reused catalyst was found to be lower than the fresh
catalyst as expected. It is attributed to the leaching of vanadium ions under the

reaction conditions thus reducing the catalytic activity. This is generally


observed with all liquid-phase reactions more predominantly with peroxide
catalyzed reaction in acetonitrile solvent.
7.6 DISCUSSION

Selective oxidation reactions of aromatics are known to follow a Mars

van Krevelen mechanism35. The reaction pathways of arenes observed with

supported vanadia catalysts are dependent on the catalyst, substrate and all
267

'.=P<"__--- _ _ _ _ . . . . _ _
other reaction parameters. The structural relationship of supported vanadia
catalysts and behaviour in benzene and ethylbenzene oxidation was already

discussed in chapters 5 and 6. The catalytic redox cycle on ceria-supported


vanadia may be due to the redox cycle of cerium near vanadium; unlike the
most supported vanadia catalysts, which work on the redox cycle of vanadium
sites in accordance for ceria supported chromia catalysts.

In naphthalene oxidation reaction, support materials shows completely

inactive nature. Hence, the activity enhancement reveals that the nature of
vanadium species and its different site isolations/coordination environments
may be responsible for the differences in the conversion/selectivity behaviour.
Catalytic activity of VC and VCRS series of catalysts exhibits the same pattem

while phthalic anhydride selectivity was more with VCRS catalysts. Small
amount of 2naphthol was also produced with VC catalysts and selectivity to

this decrease as the vanadia loading increases. Among praseodymia catalysts,


VP series only exhibits considerable activity towards oxidation but no phthalic
anhydride was observed with these catalysts.

The structural characterization of supported catalysts by various


techniques such as XRD, FT-IR, FT-Raman and UV-vis DRS shows the

presence of highly dispersed vanadia on lower loading and formation of


CeVO4 as the vanadia loading increases to 10 wt.% V205. Lower loading
consists vanadia as tetrahedral V=O species while higher loading can lead to

formation of V-O-V species on the support surface. The EPR data of ceria
containing catalysts shows that the interaction of CeO2 with vanadia stabilizes

surface Ce sites, which inturn moderating the valence change ability of the
268

Oxidation of Naphthalene

Ce4+/Ce3+ pair, as well as blocking the corresponding V redox interplay.


Vanadium would moderate the liability of ceria oxygen sites. 29Si and 51V
MAS NMR studies suggest the formation of CeVO4 even with 6 wt.% vanadia

on ceria. However for CRS supported catalysts support envisages highly


dispersed V=O species up to 10 wt.% vanadia loading. VP and VPRS catalysts

contain pyrovanadate, PrxV2O7 groups as observed by powder XRD analysis.

The fonnation of silicate like SiO-Pr conguration was evidenced from 29Si
MAS NMR studies for VPRS catalysts.

As reported, hydrocarbon hydroxylation can occur via either Hatom


abstraction or the insertion of an oxygen atom of metallo-oxene into the C-H
bond with the intermediate formation of a penta coordinated carbon atom37'38.

Scheme 7.1 shows that 1,4-naphthaquinone was produced without requiring

naphthalene ring destruction while phthalic anhydride was subsequently


produced with ring rupture as reported by Bruckner et al.39 over vanadia
catalysts. Altematively, Linstromberg et al.40 reported that naphthalene could

be directly oxidized to phthalic anhydride during oxidation over vanadium


pentoxide catalyst, and can be easily converted to phthalic acid ester. They also

argued that naphthalene followed the similar pathways undertaken by benzene

during selective gas-phase oxidation. The catalytic activity of benzene and


naphthalene oxidations conducted in this work also results the same behaviour.

Present catalytic systems of ceria supported ones shows higher concentration

of phthalic anhydride suggesting that ring rupture route was most probable

over these catalysts. This is possible with the highly dispersed tetrahedral
vanadia species on the supports. Formation of CeVO4 at higher vanadia loading

results lower activity suggesting deactivation of catalysts. We have already


269

Chapter 7

shown that nature of solvent have an important role in oxidation reaction. The

presence of aprotic solvent may yield the naphthol products. According to


Khavasi et al.41 in protic solvents, high oxo intermediate produced quinonic

compounds but in aprotic solvent, phenolic compounds were produced from


peroxo active oxidant. Production of no phthalic anhydride with praseodymia
catalysts suggests these are not able to cause ring rupture thereby oxidizing the

aromatic ring. This low activity can be attributed to the difference in redox
property of praseodymia and ceria supported vanadia catalysts.
7.7 CONCLUSION

The liquid phase oxidation of naphthalene in acetonitrile is conducted

with H20; as oxidant._All the ceria supported vanadia catalyst prepared was
considerably active towards the oxidation, which produced phthalic anhydride

as the main product while praseodymia was less active and not produced

phthalic anhydride in any catalysts. High activity and phthalic anhydride


selectivity of ceria supported vanadia can arise from the presence of tetrahedral

vanadia species as evidenced in the case of benzene oxidation. Low activity

and no phthalic anhydride production over praseodymia catalysts suggest


different redox behaviour from that of ceria.

......................................................................................... ..

270

Oxidation of Naphthalene

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