Каталітична ефективність Pd, осадженого на різних носіях, у реакції гідрування хіноліну
Pd nanoparticles were deposited on two different grades of activated carbon – NORIT and CAW. In addition, these carbons were pre-treated with HNO3 or covered by polyaniline, and these modified carbons were used as carriers for the Pd deposition. The resulting materials were tested as catalysts for t...
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| author | Yurchenko, Oleksandr O. Poturai, Andrii S. |
| author_facet | Yurchenko, Oleksandr O. Poturai, Andrii S. |
| author_institution_txt_mv | [
{
"author": "Oleksandr O. Yurchenko",
"institution": "Institute of Organic Chemistry of the National Academy of Sciences of Ukraine",
"orcid": ""
},
{
"author": "Andrii S. Poturai",
"institution": "Institute of Organic Chemistry of the National Academy of Sciences of Ukraine; Enamine Ltd.",
"orcid": ""
}
] |
| author_sort | Yurchenko, Oleksandr O. |
| baseUrl_str | https://ophcj.nuph.edu.ua/oai |
| collection | OJS |
| container_end_page | 28 |
| container_issue | 2 |
| container_start_page | 23 |
| container_title | Журнал органічної та фармацевтичної хімії |
| container_volume | 23 |
| datestamp_date | 2026-08-22T19:54:27Z |
| description | Pd nanoparticles were deposited on two different grades of activated carbon – NORIT and CAW. In addition, these carbons were pre-treated with HNO3 or covered by polyaniline, and these modified carbons were used as carriers for the Pd deposition. The resulting materials were tested as catalysts for the hydrogenation of quinoline. The best-performing samples were further tested in the hydrogenation of 4-methylquinoline. The structural features of carriers and catalysts were elucidated by the N2 adsorption studies. The grade of activated carbon was found to be a key factor controlling its performance, and the effect of the surface modification was negligible. |
| doi_str_mv | 10.24959/ophcj.25.330039 |
| first_indexed | 2025-07-23T04:43:45Z |
| format | Article |
| fulltext |
ISSN 2308-8303 (Print) / 2518-1548 (Online) 23
Original Research
http://ophcj.nuph.edu.ua
UDC 546.11+54-44:(546.98+661.183.2)
A. S. Poturai1,2, A. A. Yurchenko1
1 Institute of Organic Chemistry of the National Academy of Sciences of Ukraine,
5 Akademik Kuhar str., 02094 Kyiv, Ukraine
2 Enamine Ltd., 78 Winston Churchill str., 02094 Kyiv, Ukraine
Catalytic Performance of Pd Deposited on Various Carriers
in Hydrogenation of Quinoline
Abstract
Pd nanoparticles were deposited on two different grades of activated carbon – NORIT and CAW. In addition, these carbons
were pre-treated with HNO3 or covered by polyaniline, and these modified carbons were used as carriers for the Pd deposi-
tion. The resulting materials were tested as catalysts for the hydrogenation of quinoline. The best-performing samples were
further tested in the hydrogenation of 4-methylquinoline. The structural features of carriers and catalysts were elucidated
by the N2 adsorption studies. The grade of activated carbon was found to be a key factor controlling its performance, and the
effect of the surface modification was negligible.
Keywords: hydrogenation; palladium; activated carbon; quinoline; specific surface
А. С. Потурай1,2, О. О. Юрченко1
1 Інститут органічної хімії Національної академії наук України,
вул. Академіка Кухаря, 5, м. Київ, 02094, Україна
2 ТОВ НВП «Єнамін», вул. Вінстона Черчилля, 78, м. Київ, 02094, Україна
Каталітична ефективність Pd, осадженого на різних носіях, у реакції гідрування хіноліну
Анотація
Наночастинки Pd було нанесено на дві різні марки активованого вугілля – NORIT і CAW. Крім того, ці марки вугілля
було попередньо оброблено HNO3 або покрито поліаніліном і далі використано як носії для осадження Pd. Отримані
матеріали випробувано як каталізатори гідрування хіноліну. Найкращі зразки було надалі протестовано в реакції гі-
дрування 4-метилхіноліну. Структурні особливості носіїв і каталізаторів з’ясовано за допомогою адсорбційних дослі-
джень N2. Виявлено, що марка активованого вугілля була ключовим фактором, який контролював його ефективність,
а ефект модифікації поверхні був незначним.
Ключові слова: гідрування; паладій; активоване вугілля; хінолін; питома поверхня
Citation: Poturai, A. S.; Yurchenko, A. A. Catalytic Performance of Pd Deposited on Various Carriers in Hydrogenation of Quinoline.
Journal of Organic and Pharmaceutical Chemistry 2025, 23 (2), 23 – 28.
https://doi.org/10.24959/ophcj.25.330039
Received: 28 March 2025; Revised: 11 May 2025; Accepted: 17 May 2025
Copyright© 2024, A. S. Poturai, A. A. Yurchenko. This is an open access article under the CC BY license
(http://creativecommons. org/licenses/by/4.0).
Funding: The authors received no specific funding for this work.
Conflict of interests: The authors have no conflict of interests to declare.
■ Introduction
Hydrogenation is one of the most important
reactions in organic chemistry, and it is widely
used for both the fine synthesis and industrial
production of chemicals [1, 2]. Among hydroge-
nation catalysts, Pd-based systems play one of the
central roles due to their high efficiency, which
includes activity and selectivity, as well as good
reproducibility [3, 4]. However, in view of the high
price of palladium, searching for ways to reduce
the metal consumption is an important task.
In our preliminary studies, it was found that
the deposition of Pd nanoparticles on different
grades of activated carbon led to the formation
of catalysts with a completely different activity.
ISSN 2308-8303 (Print) / 2518-1548 (Online) 24
Журнал органічної та фармацевтичної хімії 2025, 23 (2)
This difference can be explained by the formation
of different particles due to specific surface fea-
tures (for example, different concentration and
activity of “seeding” centers, which act as the growth
sites for particles [5]), as well as different influ-
ence of the carrier on the electronic structure of
Pd particles [6]. Unfortunately, the carbons that
give the most active catalysts are the most ex-
pensive, and searching for a simple way of modi-
fying the carbon surface to “improve” it is an ur-
gent task.
The aim of this study was to evaluate the role
of the activated carbon pre-treatment determin-
ing the catalytic performance of Pd/C catalysts.
Two samples of activated carbon were chosen for
this study: (1) CAW MB240 activated carbon, and
(2) NORIT GSX activated carbon. CAW is an ac-
tivated carbon type, widely used for the purifi-
cation of wastewater and liquids in different tech-
nological processes. Its sorption characteristics
depend a lot on the batch; the sample used in
this study had SBET = 49 m2 g–1, the total pore
volume – VT = 0.164 cm3 g–1, and contained al-
most no micropores, according to the data of the
N2 sorption. NORIT is another grade of activated
carbon, produced by Norit Ltd., and it can also be
manufactured from coconut. The sample used in
this study had SBET = 850 m2 g–1, the total pore volu-
me VT = 0.604 cm3 g–1, and contained a significant
quantity of micropores, with Vmicro = 0.220 cm3 g–1
(by Dubinin-Radushkevich); the Horvath and
Kawazoe median micropore diameter was 0.64 nm.
Significantly lower sorption characteristics of CAW
compared to NORIT may be caused by a simpler
activation process used in the production of CAW;
consistently, CAW is much cheaper compared to
NORIT. The possible use of CAW instead of
NORIT after the modification with PANI seemed
to be an attractive outlook.
These carbons were oxidized by the treat-
ment with HNO3, and the oxidized carbons were
used as carriers for the Pd deposition. In another
series of experiments, a layer of polyaniline (PANI)
was deposited on activated carbon to test if the
creation of such a “PANI shell” would negate the
difference between these materials. The PANI
content was chosen at the level of 10 % by weight.
PANI was chosen as a surface modifier because
it was shown that the reduction of Pd2+ by PANI
led to a very efficient hydrogenation catalyst
where PANI served as a carrier for Pd nanopar-
ticles [7]. In addition, the deposition of PANI
over activated carbon is a technically accessible
task.
The deposition of Pd on the carriers was car-
ried out by the decomposition of the Pd2(dba)3 com-
plex (dba = dibenzylideneacetone), as previously
reported [8, 9]. The decomposition of zero-valent
complexes of metals was shown to be an efficient
way to obtain hydrogenation catalysts [10 – 13].
■ Materials and methods
Hydrogen (99.99 %) was purchased from Galo-
gas Ltd. (Kyiv, Ukraine) and used without further
purification. NORIT GSX activated carbon was
purchased from Energochimservise (Kyiv, Ukrai-
ne). CAW MB240 activated carbon was purcha-
sed from Ecofilter Ltd (Kharkiv, Ukraine). Other
starting materials and reagents, except hydrogen,
were available from Enamine Ltd. (Kyiv, Ukraine)
and UkrOrgSyntez Ltd. (Kyiv, Ukraine).
The N2 sorption was measured using Sorpto-
matic-1990 instrument by the volumetric method
at 78 K. Prior to the measurements, the samples
were heated at 200oC in a 10–4 Torr vacuum for
2 hours.
The yield of 1,2,3,4-tetrahydroquinoline was
determined by integrating signals of different pro-
ducts in 1H NMR spectra and measuring their
ratios. No product is volatile; the total quantity
of all products is equal to the quantity of the star-
ting compound. In turn, GC-MS was not used for
the quantitative analysis of the mixtures because
of the need to calibrate columns. GC-MS was used
just for verification of the products (by retention
times and MS patterns), as well as to ensure
that other products did not form. All quantita-
tive analyses were performed using NMR data.
1H spectra were measured on a Varian Unity
Plus 400 spectrometer at 400 MHz. Mass spec-
tra were measured on an Agilent 1100 LCMSD
SL instrument (chemical ionization (CI)) and an
Agilent 5890 Series II 5972 GC-MS instrument
(electron impact ionization (EI)).
The deposition of Pd on the carriers was car-
ried out, as previously reported [8, 9]. In all cas-
es, the quantity of Pd-containing starting mate-
rial, Pd2(dba)3, was chosen to ensure the 1 % Pd
content in the final product.
The oxidation of activated carbons was per-
formed by treating the carbon sample with boil-
ing diluted (30 %) nitric acid for 4 hours [14, 15].
The deposition of PANI on activated car-
bons was performed as described [8]. Since the
deposition was carried out in the acidic medium,
the samples that were formed contained proto-
nated PANI (hereinafter denoted as PANI(H+)).
ISSN 2308-8303 (Print) / 2518-1548 (Online) 25
Journal of Organic and Pharmaceutical Chemistry 2025, 23 (2)
For the conversion of these materials into those
containing neutral PANI, samples were treated
with an excess of 1 % solution of ammonia.
The hydrogenation of quinoline was perfor-
med in the high-pressure vessels as previously
described [8, 10].
■ Results and discussion
Two types of activated carbons, CAW and
NORIT, were used as starting materials for fur-
ther modification and deposition of PANI. The aim
of the surface oxidation with HNO3 was to unify
the surface, i.e., to eliminate specific functional
groups (if any) and convert them into hydroxy-
or carboxy-groups. The aim of the PANI depo-
sition was to create a uniform layer of organic
polymer, and make the conditions of the Pd na-
noparticles deposition closer, regardless of dif-
ferent grades of activated carbon.
The deposition of Pd on all carriers, i.e.,
NORIT and CAW, treated by HNO3 or covered
by PANI (in protonated and neutral forms), was
performed by the decomposition of Pd2(dba)3.
The scheme of the catalyst formation, along with
their abbreviations, is shown in Figure 1.
The hydrogenation of quinoline was chosen
as a benchmark reaction for comparing the ca-
talytic properties of the materials. In all cases,
1,2,3,4-tetrahydroquinoline (THQ) was the only
hydrogenation product. The yields of THQ
achieved in the presence of the catalysts studied
are presented in Table 1.
It was found that the NORIT-based catalysts
possessed high catalytic performance, and the quan-
titative hydrogenation of quinoline was achieved
in the cases of Pd-NORIT and Pd-NORIT-Ox in
the presence of 0.1 mol % of Pd at p(H2) = 30 bar,
T = 50 °C for 4 hours in methanol. At 0.025 mol %
Pd loading, the yield of THQ was not quantitative,
Figure 1. The preparation of Pd-containing catalysts
Table 1. The yields of 1,2,3,4-tetrahydroquinoline upon the hydrogenation of quinoline in the presence of Pd-containing catalysts under
conditions p(H2) = 30 bar, T = 50 °C, 4 h, methanol
Catalyst Pd loading, mol. % per 1 mol
of quinoline Yield of THQ, % Ref.
NORIT series
Pd-NORIT 0.1 100 this work
Pd-NORIT 0.025 92 this work
Pd-NORIT-Ox 0.1 100 this work
Pd-NORIT-Ox 0.025 74 this work
Pd-PANI(H+)/NORIT 11 100 8
Pd-PANI/NORIT 11 61 8
CAW Series
Pd-CAW 0.2 0 this work
Pd-CAW-Ox 0.2 0 this work
Pd-PANI(H+)/CAW 0.2 0 this work
Pd-PANI/CAW 1 0 this work
Note: 1 The Pd content on the catalysts was different from 1 %, but the weights of the catalysts were adjusted to ensure 1 % of Pd in the reaction mixture
ISSN 2308-8303 (Print) / 2518-1548 (Online) 26
Журнал органічної та фармацевтичної хімії 2025, 23 (2)
and it could be found that the performance of
Pd-NORIT was better compared to Pd-NORIT-Ox
(the yields of THQ were 92 % and 74 %, respective-
ly). Anyhow, the catalytic performance of these
materials was superior compared to those con-
taining PANI since in these conditions, the quan-
titative conversion of quinoline to THQ was not
achieved in the case of Pd-PANI/NORIT at 1 mol %
Pd loading.
It was previously shown that the catalysts con-
taining Pd nanoparticles on the carriers made of
PANI and NORIT had better performance com-
pared to “classical” Pd-charcoal systems where
Pd was deposited on the BAU activated carbon
[8]. From the results of the present study, we must
conclude that the high performance of such sys-
tems was due to NORIT, and not because of the
PANI “shell”.
In contrast to NORIT-based systems, catalysts
made using CAW activated carbon did not pos-
sess any catalytic activity in the conditions used
herein, i.e., p(H2) = 30 bar, T = 50 °C, 4 hours in
methanol. Their performance could not be impro-
ved by the surface oxidation with HNO3 or the
deposition of a PANI layer. We have to admit
that the idea of cheap activated carbon transfor-
mation into analogues of expensive, but active
ones, is not so simple and cannot be implement-
ed by covering with a PANI layer.
The catalytic performance of the best cata-
lysts considered herein, i.e., Pd-NORIT and
Pd-NORIT-Ox, was checked in the hydrogenation
of 4-methylquinoline. It was found that the yields
of 4-methyl-1,2,3,4-tetrahydroquinoline were higher
in the case of Pd-NORIT both at 0.2 and 0.1 mol %
Pd loading. These yields were expectedly lower
compared to the hydrogenation of non-substi-
tuted quinoline, but the tendency was the same
(Table 2).
It was previously shown that the treatment of
activated carbon with HNO3 led to the enhance-
ment of its sorption capacity in the processes of
the sorption of heavy metal ions [16], the cataly-
tic thermal decomposition of pentachlorobenzene
[17], and in the case of the use as a carrier for
hydrogenation catalysts [18]. In contrast, in our
case, the treatment of NORIT with HNO3 prior
to the deposition of Pd nanoparticles led to the
formation of a less active catalyst, and a similar
procedure had no effect on the catalyst proper-
ties in the case of CAW.
To determine changes in the structural pro-
perties of carriers and catalysts during various
treatments, and to assess their possible effect on
the catalytic performance of Pd-containing sam-
ples, N2 adsorption experiments were carried out
for the NORIT series. The results are presented
in Table 3.
The oxidation of NORIT with HNO3 led to a
ca. 2 % decrease in SBET. However, the deposition
of PANI resulted in abrupt, about 50 %, growth
of SBET. In addition, the pore volume also signifi-
cantly increased. This effect can be explained
by the formation of new roughness and folding
Table 2. The yields of 4-methyl-1,2,3,4-tetrahydroquinoline upon the hydrogenation of 4-methylquinoline in the presence
of Pd-containing catalysts in conditions p(H2) = 30 bar, T = 50 °C, 4 hours, methanol
Catalyst Pd loading, mol % per 1 mol
of quinoline Yield of THQ, % Ref.
NORIT series
Pd-NORIT 0.2 98 this work
Pd-NORIT 0.1 27 this work
Pd-NORIT-Ox 0.2 55 this work
Pd-NORIT-Ox 0.1 26 this work
Table 3. Structural properties of the NORIT-based carriers and catalysts determined from N2 adsorption isotherms
Catalyst SBET, m2 g–1 Pore volume (Gurvich)
at p/p0 = 0.95, cm3 g–1
Median micropore
diameter by Horvath
and Kawazoe, nm
Vmicro (by Dubinin-
Radushkevich), cm3 g–1
NORIT 850 0.604 0.64 0.220
Pd-NORIT 605 0.572 0.83 0.202
NORIT-Ox 830 0.588 0.74 0.284
Pd-NORIT-Ox 750 0.553 0.68 0.265
PANI(H+)/NORIT 1310 0.948 0.75 0.452
Pd-PANI(H+)/NORIT 1080 0.759 0.74 0.384
PANI/NORIT 1280 0.857 0.71 0.450
Pd-PANI/NORIT 1115 0.802 0.76 0.390
ISSN 2308-8303 (Print) / 2518-1548 (Online) 27
Journal of Organic and Pharmaceutical Chemistry 2025, 23 (2)
of the surface, including new pores, due to the
PANI layer.
The deposition of Pd in all cases led to some
decrease in the specific surface probably due to
the fact that Pd particles filled the asperities of
the surface. Similarly, the total pore volume and
the volume of micropores decreased upon the de-
position of Pd, indicating the localization of Pd
nanoparticles in pores. However, 1 % of Pd could
not ensure such a significant decrease in the pore
volume, and probably Pd nanoparticles blocked
some part of the pores, making them inacces-
sible for N2 probe molecules. It should be noted
that a 1 % decrease of the specific surface should
have been due to the “addition” of a heavy me-
tallic phase to the porous carrier.
The efficient pores diameter determined using
the Horvath and Kawazoe model, did not change
regularly upon the deposition of Pd nanoparticles
(for example, it increased in the case of NORIT
or decreased in the case of NORIT-Ox), and such
irregular variation could be an argument in fa-
vor of the pore blocking by Pd nanoparticles, in-
stead of filling the pores volume by Pd in full.
■ Conclusions
The main conclusion from this study is that
the grade of activated carbon governs the pro-
perties of the deposited Pd-containing hydro-
genation catalysts, and the performance of the
catalyst cannot be significantly changed by the
simple treatment of the carbon. In other words,
the use of suitable activated carbon as a carrier
is a key point, and the transformation of cheap
activated carbon (which acts as a carrier for the
catalysts of low activity) into a “good carrier” can-
not be achieved by the oxidative treatment with
nitric acid or the polyaniline layer formation.
In addition, PANI is a good carrier for Pd na-
noparticles for creating hydrogenation catalysts
only if one compares PANI and a “non-active” car-
bon, such as CAW. PANI can be an alternative
to cheap carbons, but the performance of activa-
ted carbon like NORIT is superior (though it is
much more expensive). The deposition of a PANI
layer on the surface of activated carbon does not
improve its performance as a catalyst carrier, de-
spite some reports about the formation of highly
active catalysts based on PANI.
The nature of activated carbon itself is a key
factor, which controls the performance of the ca-
talysts, containing Pd nanoparticles, at least in
the series where Pd was deposited in the same
way. Thus, the activated carbon grade should be
carefully selected for the preparation of Pd cata-
lysts for the hydrogenation.
■ Acknowledgement
The authors thank Pavel. S. Yaremov for the
measurement of N2 sorption isotherms.
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Information about the authors:
Andrii S. Poturai (corresponding author), Ph.D Student of the Institute of Organic Chemistry of the National Academy of Sciences of
Ukraine; Laboratory Head, Enamine Ltd.; https://orcid.org/0000-0002-3991-0920; e-mail for correspondence: a.poturai@enamine.net.
Oleksandr O. Yurchenko, Ph. D. in Chemistry, Head of the High-Pressure Laboratory, Institute of Organic Chemistry of the National
Academy of Sciences of Ukraine; https://orcid.org/0000-0002-5668-8022.
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| id | oai:ojs.journals.uran.ua:article-330039 |
| institution | Journal of Organic and Pharmaceutical Chemistry |
| issn | 2518-1548 |
| keywords_txt_mv | |
| language | English |
| last_indexed | 2026-08-23T01:00:28Z |
| publishDate | 2025 |
| publisher | National University of Pharmacy |
| record_format | ojs |
| resource_txt_mv | ophcjnupheduua/3f/45a1e6f77a35a672dab41aa459973d3f.pdf |
| spelling | oai:ojs.journals.uran.ua:article-3300392026-08-22T19:54:27Z Catalytic Performance of Pd Deposited on Various Carriers in Hydrogenation of Quinoline Каталітична ефективність Pd, осадженого на різних носіях, у реакції гідрування хіноліну Yurchenko, Oleksandr O. Poturai, Andrii S. гідрування паладій активоване вугілля хінолін питома поверхня hydrogenation palladium activated carbon quinoline specific surface Pd nanoparticles were deposited on two different grades of activated carbon – NORIT and CAW. In addition, these carbons were pre-treated with HNO3 or covered by polyaniline, and these modified carbons were used as carriers for the Pd deposition. The resulting materials were tested as catalysts for the hydrogenation of quinoline. The best-performing samples were further tested in the hydrogenation of 4-methylquinoline. The structural features of carriers and catalysts were elucidated by the N2 adsorption studies. The grade of activated carbon was found to be a key factor controlling its performance, and the effect of the surface modification was negligible. Наночастинки Pd було нанесено на два різні марки активованого вугілля – NORIT і CAW. Крім того, ці марки вугілля було попередньо оброблено HNO3 або покрито поліаніліном і далі використано як носії для осадження Pd. Отримані матеріали випробувано як каталізатори гідрування хіноліну. Найкращі зразки було надалі протестовано в реакції гідрування 4-метилхіноліну. Структурні особливості носіїв і каталізаторів з’ясовано за допомогою адсорбційних досліджень N2. Виявлено, що марка активованого вугілля була ключовим фактором, який контролював його ефективність, а ефект модифікації поверхні був незначним. National University of Pharmacy 2025-05-24 Article Article application/pdf https://ophcj.nuph.edu.ua/article/view/330039 10.24959/ophcj.25.330039 Journal of Organic and Pharmaceutical Chemistry; Vol. 23 No. 2 (2025); 23-28 Журнал органической и фармацевтической химии; Том 23 № 2 (2025); 23-28 Журнал органічної та фармацевтичної хімії; Том 23 № 2 (2025); 23-28 2518-1548 2308-8303 en https://ophcj.nuph.edu.ua/article/view/330039/320375 Copyright (c) 2025 Oleksandr O. Yurchenko, Andrii S. Poturai http://creativecommons.org/licenses/by/4.0 |
| spellingShingle | гідрування паладій активоване вугілля хінолін питома поверхня Yurchenko, Oleksandr O. Poturai, Andrii S. Каталітична ефективність Pd, осадженого на різних носіях, у реакції гідрування хіноліну |
| title | Каталітична ефективність Pd, осадженого на різних носіях, у реакції гідрування хіноліну |
| title_alt | Catalytic Performance of Pd Deposited on Various Carriers in Hydrogenation of Quinoline |
| title_full | Каталітична ефективність Pd, осадженого на різних носіях, у реакції гідрування хіноліну |
| title_fullStr | Каталітична ефективність Pd, осадженого на різних носіях, у реакції гідрування хіноліну |
| title_full_unstemmed | Каталітична ефективність Pd, осадженого на різних носіях, у реакції гідрування хіноліну |
| title_short | Каталітична ефективність Pd, осадженого на різних носіях, у реакції гідрування хіноліну |
| title_sort | каталітична ефективність pd, осадженого на різних носіях, у реакції гідрування хіноліну |
| topic | гідрування паладій активоване вугілля хінолін питома поверхня |
| topic_facet | гідрування паладій активоване вугілля хінолін питома поверхня hydrogenation palladium activated carbon quinoline specific surface |
| url | https://ophcj.nuph.edu.ua/article/view/330039 |
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