Effect of acid treatment on thermal extraction yield

in ashless coal production

Chunqi Li
a
, Toshimasa Takanohashi
a,
*
, Takahiro Yoshida
a
,
Ikuo Saito
a
, Hideki Aoki
b
, Kiyoshi Mashimo
b
a
Institute for Energy Utilization, National Institute of Advanced Industrial Science and Technology, 16-1 Onogawa, Tsukuba 305-8569, Japan
b
College of Science and Technology, Nihon University, 1-8 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-8308, Japan
Received 8 March 2003; revised 3 June 2003; accepted 4 June 2003; available online 5 December 2003
Abstract
Coals of different ranks were acid-treated in aqueous methoxyethoxy acetic acid (MEAA), acetic acid (AA), and HCl. The acid-treated
coals were extracted with polar N-methyl-2-pyrrolidinone (NMP) and nonpolar 1-methylnaphthalene (1MN) solvents at temperatures from
200 to 360 8C for 1060 min. The thermal extraction yields with NMP for some acid-treated low-rank coals increased greatly; for example,
the extraction yield for Wyodak coal (%C; 75.0%) increased from 58.4% for the raw coal to 82.9% for coal treated in 1.0 M MEAA.
Conversely, the extraction yields changed minimally for all the acid-treated coals extracted in 1-MN. The type and concentration of acid
affected the extraction yield when NMP was used as the extraction solvent. With increasing MEAA concentration from 0.01 to 0.1 M, the
extraction yield for Wyodak coal increased from 66.3 to 81.4%, and subsequently did not change clearly with concentration. Similar changes
in the extraction yield with acid concentration were also observed with AA and HCl. The de-ashing ratio for coals acid-treated in MEAA,
AA, and HCl also increased greatly with concentration from 0.01 to 0.1 M, which corresponded to the change in the thermal extraction yield
in NMP. For the acid-treated coals, high extraction yields were obtained at lower extraction temperatures and shorter extraction times than
for the raw coal. The mechanisms for the acid treatment and thermal extraction are discussed.
q 2003 Elsevier Ltd. All rights reserved.
Keywords: Ashless coal; Thermal extraction; Extraction yield; Acid treatment; N-methyl-2-pyrrolidinone
1. Introduction
Thermal extraction with organic solvents has been
used for clean, value-added utilization of coals. Thermal
extraction with polar solvents at their boiling points gave
high extraction yields for some bituminous coals [15];
for example, an extract with about 74% yield with as
little as 1000 ppm ash was obtained when the polar
solvent N-methyl-2-pyrrolidinone (NMP) was used at its
boiling point, 202 8C [4]. Miura et al. [68] developed a
method for producing clean fuels from coals with solvent
extraction using a ow-type extractor at around 350 8C,
and reported that the extract yield reached 6580% for
bituminous coals when the nonpolar solvent tetralin was
used, and reached about 80% for the sub-bituminous and
lignite coals when the polar solvent carbol oil was used.
Recently, the thermal extraction of coals with organic
solvents has been used to produce ashless coal (Hyper-
Coal) [914], which can be red directly in gas turbines
to achieve a higher net power output, resulting in
reduced CO
2
emissions. A thermal extraction yield
higher than 60% is desired; the ash content of HyperCoal
is less than 200 ppm, and there is less than 0.5 ppm
sodium and potassium. In our previous work [1214],
extraction yields higher than 60% were obtained for
several bituminous coals using a ow-type extractor at
360 8C with the nonpolar solvents 1-methylnaphthalene
(1-MN) and light cycle oil. With the polar solvents NMP
and crude methylnaphthalene oil, extraction yields higher
than 80% were obtained. With 1-MN, the high extraction
yields are attributed mainly to the heat-induced relaxation
of coal aggregates, while with NMP they are due to both
heat-induced and solvent-induced relaxation [14]. By
contrast, for some low-rank coals these extraction
conditions give relatively low extraction yields [14].
0016-2361/$ - see front matter q 2003 Elsevier Ltd. All rights reserved.
doi:10.1016/j.fuel.2003.06.002
Fuel 83 (2004) 727732
www.fuelrst.com
* Corresponding author. Tel.: 81-298-61-8441; fax: 81-29-861-8408.
E-mail address: toshi-takanohashi@aist.go.jp (T. Takanohashi).
In low-rank coals, a considerable amount of oxygen is
present in the form of carboxylic and phenolic functional
groups. The carboxylic groups in coal are known to be
present in the acid form (carboxyl group) or the salt form
(metal carboxylate group) with cations such as Mg
2
, Ca
2
,
and Na

[1517]. Therefore, signicant cation-bridging

cross-links ((COO
2
)
2
M
2
) can form between divalent
cations (such as Mg
2
and Ca
2
) and carboxylate anions,
and releasing these cross-links via cation exchange by
treatment with strong acids has been reported to enhance
coal extractability greatly [18,19]; for example, Opaprakasit
et al. [19] reported that the pyridine extraction (Soxhlet,
115 8C) yield for sub-bituminous Wyodak coal was
increased from 15% for the raw coal to 39% for coal that
was acid-treated with 0.1 M HCl. It has also been reported
that organic acids, such as methoxyethoxy acetic acid
(MEAA) and acetic acid (AA), are effective for the cation
exchange of metal carboxylate groups in coals [20,21].
In this work, in order to increase the thermal extraction
yield of some low-rank coals, coal was treated with the
organic acids MEAA and AA or the inorganic acid HCl
before thermal extraction. The detailed effects of acid
treatment on the extraction yields were investigated under
different conditions (type and concentration of acid used,
coal rank, extraction solvent, temperature, and time). The
effect of acid treatment on the thermal extraction yield for
different kinds of coal is discussed with respect to their
chemical structures.
2. Experimental
2.1. Materials
Five Argonne Premium coals (Pocahontas No. 3 (POC),
Upper Freeport (UF), Illinois No. 6 (IL), Wyodak (WY),
and Beulah-Zap (BZ) (,150 mm)) and three Indonesian
coals (Adaro (AD), Pasir (PA) (,150 mm), and Banko 97
(BA) (,74 mm)) were studied. All the coal samples were
dried in vacuo at 80 8C for 12 h. The ultimate analysis and
ash content are shown in Table 1. Reagent grade 1-MN and
NMP were used as the thermal extraction solvents without
further purication.
2.2. Acid treatment
Acid treatment of coal was carried out using aqueous
MEAA, AA, and HCl, as described elsewhere [2022]. An
approximately 4.0-g dried coal sample was treated in 150 ml
of aqueous acid with 10% ethanol under a nitrogen
atmosphere at room temperature for 24 h. Then, the acid-
treated coal was washed with deionized water 35 times
until the pH of the deionized water was near 6.0. Finally, the
acid-treated coal was dried in vacuo at 80 8C for 12 h. The
ultimate analysis and ash content of the 1.0 M MEAA acid-
treated coals are also listed in Table 1.
2.3. Thermal extraction
The thermal extraction of coal was carried out using a
ow-type extractor, as described previously [12]. A coal
sample (0.20.5 g) was charged into a stainless steel cell
(ca. 4.0 cm
3
) tted with stainless steel lters (0.5 mm) on
both sides and then set in an oven. The thermal extraction
proceeded by supplying fresh solvent (ow rate: 0.1 ml/
min) under a N
2
atmosphere (1.0 MPa) at extraction
temperatures of 200360 8C for 1060 min. After the
extraction, the extract was precipitated by adding an excess
of n-hexane (300 ml) to the extract solution when 1-MN was
used as the extraction solvent. Alternatively, when NMP
was used as the extraction solvent, the solvent was rst
evaporated, and then the extract obtained was washed with
deionized water three times. The extraction yield was
calculated on a dry ash-free basis from the weight of the
residue [12].
2.4. FT-IR measurement
FT-IR spectra were recorded using a diffuse reectance
method with a spectrometer (Nicolet MAGNA-IR) at a
resolution of 4 cm
21
.
2.5. Analysis of metal ions eluted by acid treatment
A Dionex DX 500 ion chromatograph, equipped with an
Ion Pac CS14 column using 10 mmol/l CH
3
SO
3
H as the
eluent, was used to analyze the metal ions eluted by the acid
treatments. The ow rate of the eluent was 1.0 ml/min, and
the injection loop was 25 ml. Metal ions were detected with
a conductivity meter.
Table 1
Ultimate analysis and ash content of the coal samples
Coal sample Ultimate analysis (wt%, daf) Ash (wt%, db)
C H N S O
a
Pocahontas No.3(POC) 89.7 4.5 1.1 0.7 4.0 4.8
POC acid-treated
b
90.0 4.3 1.2 0.6 3.9 3.3
Upper Freeport (UF) 86.2 5.1 1.9 2.2 4.6 13.1
UF acid-treated
b
86.7 5.0 1.7 2.3 4.3 12.2
Illinois No. 6(IL) 76.9 5.5 1.9 5.6 10.1 15.1
IL acid-treated
b
76.5 5.3 2.0 5.8 10.4 12.0
Wyodak (WY) 75.0 5.4 1.1 0.5 18.0 8.8
WY acid-treated
b
74.5 5.6 1.2 0.6 18.1 3.9
Adaro (AD) 73.0 5.1 1.1 0.0 20.8 1.8
AD acid-treated
b
72.9 5.2 1.1 0.0 20.8 0.7
Pasir (PA) 73.5 5.3 1.9 0.2 19.1 4.9
PA acid-treated
b
74.4 5.3 1.7 0.2 18.4 3.5
Beulah-Zap (BZ) 71.6 4.8 1.0 0.9 21.7 9.6
BZ acid-treated
b
72.0 5.0 1.1 0.8 21.1 3.0
Banko 97 (BA) 70.0 5.3 1.3 0.3 23.1 2.4
BA acid-treated
b
70.4 5.4 1.2 0.4 22.6 0.8
a
By difference.
b
Methoxyethoxy acetic acid (1.0 M ).
C. Li et al. / Fuel 83 (2004) 727732 728
3. Results
3.1. Effects of extraction solvent and coal rank on the
extraction yield of acid-treated coal
Table 2 lists the thermal extraction yields for raw and
acid-treated (1.0 M MEAA) coals with 1-MN and NMP at
360 8C for 60 min. When 1-MN was used as the extraction
solvent, the extraction yields for high-rank POC and all the
low-rank raw coals were lower than those for the middle-
rank UF and IL coals, and the extraction yields for all the
coals examined did not change very much with acid
treatment. When NMP was used as the extraction solvent,
the extraction yields for the high-rank POC and low-rank
WY and BZ raw coals were also much lower than for the
other coals, while relatively high extraction yields were
obtained for the low-rank AD, PA, and BA raw coals. With
acid treatment, the yields for the WY and BZ coals in NMP
increased greatly; the yields for the acid-treated WY and BZ
coals were increased 82.9 and 79.0% from 58.4% and 30.5%
for the raw coals, respectively. For the low-rank PA coal,
the middle-rank UF and IL coals, and the high-rank POC
coal, acid treatment had little effect on the extraction yields,
even with NMP. Therefore, acid treatment effect on
extraction yield was heavily coal sample dependent. The
mechanism for the acid treatment and thermal extraction are
discussed later.
3.2. Effects of acid type and concentration on the extraction
yield for acid-treated coal
As shown in Fig. 1, the extraction yield for WY coal in
NMP increased from 58.4% for the raw coal to 66.3% for
coal that was acid-treated in 0.01 M MEAA; furthermore,
increasing the concentration of MEAA to 0.1 M, increased
the extraction yield to 81.4%, after which no clear change in
the extraction yield was observed as the concentration was
increased to 1.0 M. Similar trends were obtained with AA
and HCl. Fig. 1 also shows that HCl gave higher extraction
yields than MEAAand AAat the same concentrations. Fig. 2
shows that the de-ashing ratio increased with increasing acid
concentration for all the acids used. From 0.01 to 0.1 M, the
de-ashing ratio increased greatly, and subsequently did not
change much. For the same concentration, the de-ashing
ratio increased in the order HCl . MEAA . AA. These
results correspond to the changes in the extraction yield, as
shown in Fig. 1.
3.3. Effect of extraction temperature on the extraction yield
for acid-treated coal
Fig. 3 shows the extraction yields for raw and acid-
treated (1.0 M MEAA and AA) WY coals in NMP at
different temperatures. For the raw coal, the extraction
yields did not change from 200 to 250 8C, and then
increased gradually with temperature from 250 to 360 8C.
For the coal treated in 1.0 M AA, the extraction yields were
similar to those for the raw coal from 200 to 270 8C. Then,
the extraction yield increased greatly with increasing
temperature; at 320 8C, a yield of 69.8% was obtained,
Table 2
Extraction yields for raw and acid-treated coal sample
a
Coal sample Extraction solvent
1-MN NMP
Raw Acid-treated
b
Raw Acid-treated
b
POC 27.5 23.4 28.4 26.5
UF 61.4 63.6 80.2 78.1
IL 53.7 55.8 89.8 90.3
WY 31.9 35.7 58.4 82.9
AD 32.0 35.8 70.2 81.2
PA 39.8 38.9 77.3 78.2
BZ 28.8 31.2 30.5 79.0
BA 30.6 32.8 72.3 79.3
a
At 360 8C for 60 min.
b
Methoxyethoxy acetic acid (1.0 M ).
Fig. 1. Extraction yields with NMP at 360 8C for 60 min, for acid-treated
WY in MEAA, AA, and HCl at different concentrations.
Fig. 2. De-ashing ratios for WYcoal acid-treated in MEAA, AA, and HCl at
different concentrations.
C. Li et al. / Fuel 83 (2004) 727732 729
which was higher than that for raw coal at 360 8C. For coal
treated in 1.0 M MEAA, the extraction yields were much
higher at temperatures from 200 to 250 8C than for the raw
coal or coal treated in 1.0 M AA; at 270 8C, the extraction
yield was increased to 70.2%, which was higher than that for
the raw coal at 360 8C.
The differences in extraction yields for MEAA and AA
treatments against the extraction temperature imply that the
chemical structures after those acid treatments may be
different, although similar de-ashing ratio was obtained for
them. The detailed reason needs further investigation.
3.4. Effect of extraction time on the extraction yield
for acid-treated coal
Fig. 4 shows the extraction yields for acid-treated (1.0 M
AA) and raw WY coal in NMP for different extraction
times. For the raw coal, the extraction yields increased
gradually from 10 to 60 min. For the acid-treated coal,
the extraction yield for a 10 min extraction was 64.6%,
which was higher than that for raw coal extracted for
60 min. Moreover, the yield for the acid-treated coal
increased to 81.0% for a 40-min extraction.
4. Discussion
Fig. 5(a) shows FT-IR spectra of WY coal acid-treated in
1.0 M MEAA (A), raw coal (B) and the difference spectrum
(C). With acid treatment, the bands near 1400 and
Fig. 3. Extraction yields with NMP at 200360 8C for 60 min, for raw and
acid-treated (1.0 M MEAA and AA) WY coal.
Fig. 4. Extraction yields with NMP at 360 8C for 1060 min, for raw and
acid-treated (1.0 AA) WY coal.
Fig. 5. FT-IR spectra of acid-treated (A) and raw (B) coal, and the
difference spectrum (C); (A) (B). (a) WY, (b) BZ and (c) PA coals.
C. Li et al. / Fuel 83 (2004) 727732 730
1555 cm
21
decreased and the band near 1720 cm
21
increased. The bands near 1400 and 1555 cm
21
are assigned
to metal carboxylate groups, and that near 1720 cm
21
to
carboxyl groups [19]. This result suggests that acid
treatment converted the metal carboxylate groups into
carboxyl groups. Similar changes in FT-IR spectra were also
observed for acid-treated BZ coal, as shown in Fig. 5(b)
[22]. Table 3 shows the metal ion contents of the raw coal,
and ions removed by acid treatment with 1.0 M MEAA. WY
and BZ raw coals contained relatively large quantities of
Mg
2
and Ca
2
ions, as compared to the other raw coals, and
the acid treatment removed almost all of the Mg
2
and
Ca
2
ions. MEAA is reported to be effective for eliminating
cation bridging via oxygen functional groups in low-rank
coals [20,21]. For BZ coal, the acid treatment also removed
many Na

ions, although Na

is a univalent cation and

cannot form cation-bridging cross-links like divalent
cations. Consequently, the cation-bridging cross-links
formed via the metal carboxylate groups in the raw coal
might be released by converting the metal carboxylate
groups into carboxyl groups, by removing Mg
2
and Ca
2
ions; new hydrogen bonds would form among the carboxyl
groups [23]. The aprotic dipolar solvent NMP is effective
for releasing some noncovalent bonds through its strong
interaction with polar sites in coals, such as hydroxyl groups
[24]. The removal of cation-bridging cross-links in some
coals may allow more NMP to diffuse inside the coal, and
newly formed hydrogen bonds might be more easily
released by NMP, resulting in the higher extraction yield
for acid-treated coals. It has also been reported [25,26] that
newly formed associations between NMP and polar oxygen
functional groups can prevent retrogressive reactions, such
as coupling reactions between oxygen functional groups,
also increasing the extraction yield.
As shown in Fig. 5(c), for PA coal, after acid treatment
there were no signicant changes near 1400, 1555, or
1720 cm
21
. A similar result was observed for BA coal [22].
Table 3 shows that for PA coal, fewer Mg
2
and Ca
2
ions
were eluted with acid treatment than for WY and BZ coals.
In addition, an obvious carboxyl group peak near
1720 cm
21
was observed in the raw coal (Fig. 5(c); (B)).
Therefore, there are many carboxyl groups in raw PA coal.
As a result, hydrogen bonds can form between the carboxyl
groups, and are easily released by NMP. Therefore, high
extraction yields were obtained for the raw coals, without
acid treatment, as shown in Table 2.
Fig. 6. FT-IR spectra of acid-treated (A) and raw (B) coal, and the
difference spectrum (C); (A)(B). (a) IL, (b) UF and (c) POC coals.
Table 3
Metal ions in raw coal, and those removed by the acid treatment with 1.0 M
MEAA
Coal Metal ion (mg/g, coal)
Na K Mg Ca
Raw
a
Rem.
b
Raw
a
Rem.
b
Raw
a
Rem.
b
Raw
a
Rem.
b
POC 0.71 0.47 0.24 0.13 0.58 0.41 4.39 4.26
UF 0 0 2.94 0.14 1.26 0.56 3.93 3.56
IL 0 0 3.63 0.17 1.09 0.94 8.52 8.45
WY 0.98 0.86 0.58 0.16 1.91 1.88 9.49 9.35
AD 0.78 0.50 0.11 0.08 0.74 0.74 2.65 2.43
PA 0.18 0.13 0.33 0.16 0.28 0.15 1.24 1.05
BZ 5.53 5.11 0.75 0.21 4.33 4.15 16.95 16.81
BA 0.50 0.11 0.32 0.38
a
Contained in raw coal, based on the analysis data from Argonne and
CCUJ.
b
Removed by acid treatment.
C. Li et al. / Fuel 83 (2004) 727732 731
Table 3 also shows that acid treatment eluted much
Ca
2
ion from higher-rank IL, UF, and POC raw coals,
although acid treatment did not increase the extraction yields
for these coals, as shown in Table 2. After the acid treatment
of IL, UF, and POC coals, no signicant changes near 1400,
1555, or 1720 cm
21
were observed (Fig. 6). In addition, no
clear peaks near 1720 cm
21
were seen in these raw coals.
Therefore, there are few carboxyl or metal carboxylate
groups in these middle- and high-rank coals. Instead of metal
carboxylate groups, other forms of Ca
2
ion may exist in
these coals, although their chemical structure is unknown.
In summary, acid treatment had different effects on the
thermal extraction yields of different coals depending on the
conversion of metal carboxylate groups in the raw coals to
carboxyl groups. The type and concentration of acid also
affected the yield; increasing the acid concentration from
0.01 to 0.1 M enhanced the yields greatly, suggesting that
0.1 M acids are sufcient to release the cation-bridging
cross-links by removing metal ions in metal carboxylate
groups. The results corresponded to changes in the de-ashing
ratio with acid treatment. In addition, the increase in removal
ratios of Mg
2
and Ca
2
ions was also conrmed with
increasing the acid concentration from 0.01 to 0.1 M, and
those detailed data, together with the detailed mechanisms of
acid treatment and thermal extraction, are reported in another
paper [27]. Furthermore, high extraction yields for acid-
treated coals were obtained at lower extraction temperatures
and shorter extraction times than for the raw coal, indicating
that acid treatment not only increased the extraction yield,
but also lowed extraction temperature and shortened the
extraction time to obtain a high extraction yield.
5. Conclusions
The effects of acid treatment on the thermal extraction
yield with the polar solvent NMP and the nonpolar solvent
1-MN at temperatures from 200 to 360 8C for 1060 min
were investigated, and the following conclusions were
obtained.
The effects of the acid treatment were strongly dependent
on the coal type and extraction solvents used. The thermal
extraction yields for some low-rank coals extracted in the
polar solvent NMP were greatly increased, while the
changes in the yield for all the acid-treated coals extracted
in the nonpolar solvent 1-MN were minimal. Acid treatment
converts metal carboxylate groups in coal into carboxyl
groups, which form new hydrogen bonds that are more
easily released by the polar solvent NMP, resulting in the
higher extraction yield for acid-treated low-rank coals. The
type and concentration of acid also affected yield; increas-
ing the concentration from 0.01 to 0.1 M enhanced the yield
greatly. This result corresponded to the changes in the de-
ashing ratio with the acid concentration. High extraction
yields for acid-treated coals were obtained at lower
extraction temperatures and shorter extraction times than
for the raw coals. The detailed mechanism involved in acid
treatment and thermal extraction under various conditions
needs further investigation.
Acknowledgements
This work was nancially supported by the New Energy
and Industrial Technology Development Organization
(NEDO). The authors thank Ms Fengjuan Xiao for FT-IR
measurements and Mr Shinsuke Okita of Shinnikka
Environmental Engineering Co., Ltd for ion chromatograph
measurements.
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