Bioresource Technology 98 (2007) 1454–1459

Qualitative analysis of products formed during the acid

catalyzed liquefaction of bagasse in ethylene glycol
Ting Zhang a, Yujie Zhou b, Dehua Liu a,*
, Leo Petrus c

a
Department of Chemical Engineering, Tsinghua University, Beijing 100084, China
b
Institute of Nuclear and New Energy Technology, Tsinghua University, Beijing 100084, China
c
Shell Global Solutions International B.V., Box 38000, 1030 BN, Amsterdam, The Netherlands

Received 25 January 2006; received in revised form 3 March 2006; accepted 6 March 2006
Available online 8 December 2006

Abstract

Bagasse was liquefied in ethylene glycol (EG) catalyzed by sulfuric acid at 190 C under atmospheric pressure. The compositions of
the crude products obtained were analyzed after separating them into three fractions: a water-soluble fraction, an acetone-soluble frac-
tion and a residue. With infrared, gel permeation chromatography and elemental analyses, the residue mainly included undissolved cel-
lulose and lignin derivatives and the acetone-soluble fraction mainly contained lignin degradation products with high molecular weights.
The water-soluble fraction, after further analyzed by GC-MS and HPLC, showed EG, diethylene glycol, EG derivatives, saccharides,
alcohols, aldehydes, ketones, phenols, especially some acids such as formic acid, levulinic acid, acetic acid, oxalic acid and 2-
hydroxy-butyric acid and their esters. The Higher Heating Value (HHV) of the residue and the acetone-soluble fractions were higher
than that of bagasse. The results showed that some useful chemicals and biofuels could be obtained by this process.
 2006 Elsevier Ltd. All rights reserved.

Keywords: Liquefaction; Ethylene glycol; Bagasse; Analysis

1. Introduction mass under moderate temperature and low, or even

Lignocellulosic materials are the most abundant renew-
able resources in the world. Chemical liquefaction is a very
effective method to convert those solid lignocellulosic mate-
rials into liquid products, which are potential intermediates
for the production of biofuels or chemicals. Traditional liq-
uefaction processes are operated under high temperature
and high pressure, such as the PERC process by Apell
et al. (1971), the LBL process established by Lawrence
Berkeley Laboratory (Figueroa et al., 1982) and the HTU
process developed by Shell (Goudriaan and Peferoen,
1990). Therefore, those processes are usually complex and
expensive and their products are normally crude oil, which
are complex mixtures and very difficult to separate, or con-
vert into certain pure chemicals. The liquefaction of bio-
*
Corresponding author. Tel./fax: +86 010 62794742.
E-mail address: dhliu@tsinghua.edu.cn (D. Liu).
atmospheric pressure has received more and more atten-
tions (Yu, 1982; Shiraishi et al., 1992). Products from mild
liquefaction can be applied as fuels and fuel additives (Yu,
1982; Demirbas, 2000), or materials to make resins (Lin
et al., 1995; Lee et al., 2002) and polyurethane films
(Kurimoto et al., 2001).
Some developments on the analyses of liquefied prod-
ucts under mild liquefaction have been achieved (Yamada
and Ono, 1999, 2001; Yamada et al., 1996, 2001; Chen
et al., 2003). Yamada et al. (1996) liquefied cellulose in
phenol and water and found that the products were mainly
5-hydroxymethyl furfural (HMF), glucose and oligosac-
charides. Yamada et al. (2001) pointed out that HMF
derivatives, which originated from the degradation of cellu-
lose, might partly polymerize to produce residue when liq-
uefaction reaction time was prolonged. Yamada and Ono
(2001) also studied the products from cellulose liquefaction
with ethylene glycol (EG), and separated the products into

0960-8524/$ - see front matter  2006 Elsevier Ltd. All rights reserved.
doi:10.1016/j.biortech.2006.03.029
 T. Zhang et al. / Bioresource Technology 98 (2007) 1454–1459
a chloroform extract, a water extract and a residue. He
found that monomer saccharides and EG-glucoside were
mainly present in the aqueous layer, and formic acid, levu-
linic acid (LAc) and 2-hydroxyethyl levulinate, which was
the ester of LAc and EG, could be found in the chloroform
extract layer. 3-(2-Methyl-[1,3]dioxolan-2-yl)-propionic
acid ethyl ester was detected as the main degradation prod-
uct of cellulose by Chen et al. (2003). Lignin liquefaction
products are difficult to identify and characterize, because
most of them have high molecular weights and complex
structures. Only the degradation mechanism of a b-O-4 lig-
nin model compound in phenol had been studied with/
without catalyst (Lin et al., 1997a,b,c, 2001a,b). In this arti-
cle, compositions of liquefied products from bagasse,
instead of pure cellulose or lignin model compounds, were
systematically investigated in detail. Three separated frac-
tions of crude product were analyzed, including a water-
soluble fraction, an acetone-soluble fraction and a residue.
2. Methods
2.1. Materials
Bagasse from Guangxi province in Southern China was
used as raw material. Particles in the size range of 0.90 mm
to 0.45 mm (20–40 mesh) were used in the experiments.
Chemical and elemental composition data of this bagasse
are given in Table 1. All chemicals used were analytical
reagent grade.
2.2. Liquefaction of bagasse
Air-dry bagasse (10 g), 100–120 g EG and 1.25–5.0 g
97% sulfuric acid were adequately premixed. Then they
were transferred into a 250-mL three-necked flask equipped
with a mechanical agitation system and a globular reflux
Table 1
Chemical and elemental composition of bagasse
Component or element wt (%)
Chemical composition:
Klason lignin 17.82
Cellulose 42.91
Hemicellulose 32.34
Ethanol–benzene solubles 2.57
Cold water solubles 2.15
Ash 2.09
Elemental composition:
C 40.09
H 5.02
N 0.70
O 54.19
Notes: Klason lignin, holocellulose, ethanol–benzene solubles, cold water
solubles and ash content were analyzed (National Standards of People’s
Republic of China, 1993). Cellulose content was determined by the nitric
acid-ethanol method (Shi, 2003). Hemicellulose is calculated by difference
between hollocellulose and cellulose. All of the data were based on dry raw
material.
1455
condenser. The flask was heated in an oil bath at 130–
190 ± 1 C. After a preset time, the reactor was cooled to
room temperature using a cold water bath of about 5 C.
2.3. Separation of the liquefied products
The procedure for liquefied products separation is
shown in Fig. 1. The liquefied products were separated in
three fractions: a water-soluble fraction, an acetone-soluble
fraction and a residue.
2.4. Fourier transformed infrared (FTIR) measurements
IR spectra of samples with equal weights molded in KBr
pellets were analyzed by a Perkin–Elmer Spectrum GX
spectrometer.
2.5. Elemental analysis
C, H, N contents of samples were determined by an EA
I4401 element analyzer. Oxygen content was estimated
based on an assumption that the samples only contain
the elements of C, H, N and O. The Higher Heating Value
(HHV) of the sample was calculated based on the Dulong
formula.
HHV ðMJ=kgÞ ¼ 0:3383  C þ 1:442  ðH-O=8Þ ð1Þ
In which C, H and O represent the weight percentages of
carbon, hydrogen and oxygen, respectively.
2.6. Gel permeation chromatography (GPC)
The acetone-soluble fractions were analyzed by GPC on
a SHIMADZU High Performance Liquid Chromatograph
(HPLC), equipped with a SPD-M10A Diode Array Detec-
tor at 254 nm and a SHIMPACK GPC-8025 column. The
column temperature was 27 C, and the mobile phase was
tetrahydrofuran (THF), the flow rate of which was 1 mL/
min. The concentration of the tested samples was 0.5–
1 wt% in THF, and the injection size was 20 lL. The
molecular weight of the samples were calibrated by mono-
disperse polystyrene standards.The molecular weight distri-
butions were plotted as differential curves. The x-axis was
the logarithm of molecular weight (log [M]), and the y-axis
was the differential area percentage on the basis of the total
absorbance area.
2.7. Gas chromatography and mass spectrometry (GC-MS)
The liquefied products in the aqueous solution were
extracted with dichloromethane. After concentration in a
rotary evaporator at 50 C, the sample was silylated (i.e.
converted to the trimethylsilyl derivative). In the sylilation
procedure, 1 mL of pyridine was added to 10 mg sample.
Thereafter, 0.2 mL hexamethyldisilazane and 0.1 mL trim-
ethylchlorosilane were added as well, and the mixture
reacted at 70 C for 1 h. During the heating period the mix-
1456 T. Zhang et al. / Bioresource Technology 98 (2007) 1454–1459

Liquefied products

Washing with water

Filtration
Water insoluble fraction

Extracting with acetone

Filtration

Aqueous solution Acetone solution Acetone insoluble fraction

80°C rotary evaporation in vacuum 70˚C rotary evaporation Drying

Water-soluble fraction Acetone-soluble fraction Residue

Fig. 1. Procedure for liquefied products separation.

ture was concentrated using a N2 purge. A Turbmass GC-

MS was used to analyze the liquefied products qualita-
tively. Dichloromethane extracts were directly analyzed
using a DB-wax capillary column (polar). Temperature of
the column was programmed from 60 to 300 C at a rate
of 10 C/min. A DB-5 capillary column (apolar) was also
used, with a temperature program of 60–300 C at a rate
of 3 C/min. Silylethers of compounds with hydroxyl
groups were analyzed on a DB-5 column using the same
temperature program.

2.8. High performance liquid chromatography (HPLC)

A SHIMADZU High Performance Liquid Chromato-

graph (HPLC) was used, equipped with a CTO-10vp
refractive index detector and an Aminex HPX-87H col-
umn. The column temperature was 65 C, and the mobile
phase was 0.005 mol/L H2SO4 solution, the flow rate of
which was 0.8 mL/min.
3. Results and discussion
3.1. Infrared (IR) spectroscopy
Fig. 2 gives the IR spectra of bagasse, the residue, the
water-soluble fraction and the acetone-soluble fraction. It
showed that the IR spectrum of the residue (b) had charac-
teristic bands of cellulose (3403 cm1, 1064 cm1,
798 cm1), benzene rings (1614 cm1, 1513 cm1,
1427 cm1, 1368 cm1, 1234 cm1) and carbonyl groups
(1711 cm1). The spectrum of the residue (b) was quite sim-
ilar to that of bagasse (a), but its bands of cellulose were
stronger and the bands of lignin were much weaker than
those of bagasse. This indicated that under those liquefac-
tion conditions, the residue mainly contained undissolved
Fig. 2. IR spectra of bagasse and its liquefaction products (a) bagasse, (b)
residue, (c) water-soluble part, (d) acetone-soluble part. Note: the mass of
bagasse/EG = 1/12, H2SO4 0.5%, 190 C, 2 h.
cellulose and some lignin or lignin derivatives. The phe-
nomenon that lignin is easier liquefied in ethylene glycol
than cellulose, was also observed by Yamada and Ono
(1999).
The IR spectrum of the water-soluble fraction (c)
included stretching vibration of hydroxyl groups
(3386 cm1), stretching vibration of C–O (1085 cm1,
1042 cm1), which might be from alcohols or ethers. And
it also had stretching vibration of carbonyl groups
(1715 cm1), plane deviational vibration of –OH in carbox-
ylic groups (1409 cm1) and out-of-plane deforming vibra-
tion of O–H in carboxylic groups (882 cm1), which might
be from carboxylic acids. The alcohol bands mainly origi-
nated from EG, and the ethers bands were mainly from
EG ethers. Moreover, carboxylic acids might be the degra-
dation products of cellulose or hemicellulose.
 T. Zhang et al. / Bioresource Technology 98 (2007) 1454–1459 1457

The IR spectrum of the acetone-soluble fraction (d) Table 3

showed that the bands of cellulose had disappeared. How- M n , M w and M w =M n of the acetone-soluble fraction
ever, the bands of benzene rings (1607 cm1, 1514 cm1, Total Peak 1 Peak 2 Peak 3 Peak 4
1459 cm1, 1242 cm1, 1118 cm1, 837 cm1), and car- Mn 151 1233 321 67 18
bonyl groups (1708 cm1) were very strong, especially the Mw 1136 1714 363 76 21
bands of syringyl rings (1326 cm1, 1242 cm1, M w =M n 7.51 1.39 1.133 1.13 1.15
Area% – 59.90 23.56 7.62 7.53
1118 cm1), which indicated that the acetone-soluble frac-
tion mainly contained the degradation products of lignin. Notes: Liquefaction conditions: 190 C, mass of bagasse/EG = 1:10,
H2SO4 5%, 1 h.

3.2. Elemental analysis

Bagasse, residue and the acetone-soluble fraction were
analyzed using an element analyzer to obtain their C, H,
N, O contents, as shown in Table 2. After liquefaction,
the C content of the residue increased, and the O content
decreased. The Higher Heating Value (HHV) of the residue
was higher than that of bagasse, but close to the HHV of
cellulose, because the undissolved cellulose was the main
component in the residue confirmed by IR analysis. More-
over, the C content and HHV of the acetone-soluble frac-
tion increased considerably, and the O content was much
lower than that of bagasse and the residue, because deoxy-
genation happened by a series of dehydration and conden-
sation reactions to remove water in ethylene glycol
catalyzed by sulfuric acid. Due to the much milder liquefac-
tion conditions, the HHV of acetone-soluble fraction was
lower than that of heavy oil (Qu et al., 2003) and the
upgraded oil (Rezzoug and Capart, 2002) produced by
the liquefaction under high pressure and high temperature.
However, the obvious increment of the HHV of the ace-
tone-soluble fraction still indicated its promising applica-
tion as biofuels.
3.3. Gel permeation chromatography (GPC)
GPC was applied to obtain the molecular weight distri-
bution of the acetone-soluble fraction (190 C, H2SO4 5%,
1 h). The number average molecular weight ðM n Þ, the
weight average molecular weight ðM w Þ and the dispersion
ðM w =M n Þ of the whole acetone-soluble fraction and Peak
1, Peak 2, Peak 3 and Peak 4 were listed in Table 3, which
were the peaks of main fractions. M w of the whole acetone-
soluble fraction was 1136, and the dispersion was 7.51. The
main fraction, Peak 1, included components with high
molecular weights, whose M w was 1714, and Peak 2 were
relatively low molecular weight components, whose M w
was 363. M w of Peak 3 was only 76, which possibly
included a little remnant EG, and M w of Peak 4 was only
21, which could be a small amount of water. Therefore,
the acetone-soluble fraction mainly contained high molec-
ular weight products, which were partially from lignin
degraded products and hard to be detected by GC and
GC-MS.
3.4. GC-MS
GC-MS was used to obtain more detailed information of
the water-soluble liquefied products with lower boiling
points and lower molecular weights. The liquefaction of
bagasse was carried out at 190 C in the presence of 5
%wt H2SO4 for 3 h, with a bagasse vs EG mass ratio equal
to 1:10. The liquefied products were separated by the
method shown in Fig. 1. The dichloromethane extract of
the aqueous solution was analyzed using GC-MS with a
DB-wax column. Mainly two groups of substances were
detected, ethylene glycol (EG) derivatives and the degrada-
tion products of cellulose and hemicellulose. The main EG
derivatives were EG condensation products and their
monoesters or diesters of formic acid and acetic acid. The
main byproducts of EG were 2-(2-hydroxy-ethoxy)-ethanol
(DEG, diethylene glycol), [1,4]dioxane and 2-[2-(2-
hydroxy-ethoxy)-ethoxy]-ethanol (TEG, triethylene glycol).

Table 2
Elemental analysis of bagasse and its liquefaction productsa
C (%) H (%) N (%) O (%) H/C O/C N/C HHV (MJ kg1)
Bagasse 40.09 5.02 0.70 54.19 0.13 1.35 0.018 11.04
Celluloseb 44.44 6.17 0.00 49.39 0.14 0.11 0.000 15.03
Residue 50.17 5.50 0.45 43.88 0.11 0.87 0.009 16.99
Acetone-soluble 62.96 5.88 0.15 31.01 0.09 0.49 0.002 24.19
Heavy oilc 74.71 5.90 0.00 19.38 0.08 0.26 0.000 30.29
Heavy oild 84.90 8.30 0.00 6.10 0.10 0.07 0.000 39.59
Notes: HHV (MJ kg1) = 0.3383 C+1.442(H–O/8).
a
Liquefaction conditions: the mass of bagasse/EG = 1/12, H2SO4 0.5%, 190 C, 2 h.
b
Denoted as (C6H10O5)n.
c
Liquefaction conditions of Heavy oil: 340 C, 10 min, 8 g biomass and 100 ml water (Qu et al., 2003).
d
Upgrading conditions of Heavy oil: 350 C, 1 h, NiMo (15% by wt in primary oil), initial H2 pressure 3 MPa, mass of tetralin/primary oil = 3. Primary
oil was made at 250 C for 10 min, using 8 g biomass and 100 ml water (Rezzoug and Capart, 2002).
1458 T. Zhang et al. / Bioresource Technology 98 (2007) 1454–1459

Another group of liquefied products included Levulinic
acid (LAc) and an ester named 3-(2-methyl-[1,3]dioxolan-
2-yl)-propionic acid ethyl ester, from LAc, EG and
ethanol. Chen et al. (2003) also found 3-(2-methyl-
[1,3]dioxolan-2-yl)-propionic acid ethyl ester in the lique-
fied products of cellulose, using EG in the presence of sul-
furic acid and phenol as catalyst. LAc had been reported to
be an important chemical material to produce medicine,
pesticides, spices, cosmetics, resins and fuel additives (Lei
et al., 2004). A condensation product from EG and 2,5-
hexanedione, 4-(2-methyl-[1,3]dioxolan-2-yl)-butan-2-one,
was also found. However, the structures of several prod-
ucts probably originating from cellulose and hemicellulose
were uncertain yet.
The dichloromethane extract was also analyzed using a
DB-5 column. Some other degradation products were
detected such as phenol, 2-methoxy-phenol, 4-ethyl-phe-
nol, 2,6-dimethoxy-phenol and hexahydro-[1,4]diox-
ino[2,3-b][1,4] dioxine, the product from EG and glyoxal.
Some liquefied products above were confirmed by GC-
MS analysis of trimethylsilylated dichloromethane extract.
The silylethers of LAc, methanol, oxalic acid and 4-
hydroxy-butyric acid were found. Meanwhile, some fatty
acids were detected, such as hexadecanoic acid, linoleic
acid and octadecanoic acid, which might have already
existed in bagasse before liquefaction.
3.5. High performance liquid chromatography (HPLC)
The water-soluble fraction were analyzed by HPLC, as
shown in Fig. 3. Some monosaccharides such as glucose
and xylose were detected, which retention times were
respectively 6.87 min and 7.27 min. Glucose originates
from the hydrolysis of cellulose and xylose is from hemicel-
lulose. At the same time, levulinic acid was also detected,
which retention time was 11.46 min. Ethylene glycol, dieth-
ylene glycol and triethylene glycol were eluted at 12.16 min,
12.45 min and 12.65 min, respectively, but they could not
be separated completely by HPLC when mixed up, which
was confirmed by a blank run of the reaction products with
only EG and sulfuric acid. The substances eluted at
10.24 min might be formic acid.
3.6. Discussion
IR analysis showed that the water-soluble fraction
included a lot of alcohols, ethers derived from EG and
some acids, which was confirmed by GC-MS and HPLC
analysis. The water-soluble fraction mainly included fol-
lowing substances (some of them could not be directly
detected, but their derivatives reacted with EG or their sil-
ylethers were found):
• EG and its derivatives: EG, DEG, TEG, [1,4]dioxane,
etc.
• Saccharides: glucose, xylose, etc.
• Acids and their esters: levulinic acid (LAc) and its deriv-
atives such as 3-(2-methyl-[1,3]dioxolan-2-yl)-propionic
acid ethyl ester; formic acid, acetic acid, oxalic acid,
2-hydroxy-butyric acid, fatty acids, etc.
• Alcohols: methanol, ethanol, etc.
• Aldehydes and ketones: acetaldehyde, 2,5-hexanedione,
glyoxal, etc.
• Phenols: phenol, 2-methoxy-phenol, 4-ethyl-phenol, 2,6-
dimethoxy phenol, etc.
Acids are mainly produced by the degradation of cellu-
lose and hemicellulose. Levulinic acid and formic acid are
formed by degradation of cellulose via glucose and 5-
hydroxymethyl furfural. Furthermore, 3-(2-methyl-
[1,3]dioxolan-2-yl)-propionic acid ethyl ester is formed
from LAc, EG and ethanol. Acetaldehyde and glyoxal

Fig. 3. PLC chromatogram of the water-soluble fraction of the liquefied products.

 T. Zhang et al. / Bioresource Technology 98 (2007) 1454–1459
could also be the degradation products of glucose (Gharieb
et al., 1998). Methanol is mainly formed by cleavage of the
methoxy group of uronic acid units in hemicellulose, while
acetic acid is formed by cleavage of the acetyl group of
xylose units in hemicellulose. Phenols are chiefly from the
low molecular weight degradation products of lignin. How-
ever, structures of several products probably from cellulose
and hemicellulose were uncertain yet.
4. Conclusions
Liquefaction residue mainly consisted of undissolved
cellulose and some lignin or lignin derivatives, whose
HHV was higher than that of bagasse. Based on IR and
GPC analyses, the acetone-soluble fraction mainly con-
tained lignin degradation products with high molecular
weights. Its predicted HHV value was much higher than
that of bagasse, therefore the dissolved products in this
fraction could be interesting as fuel components. The water
soluble fraction mainly contained saccharides, alcohols,
aldehydes, ketones, phenols and especially some acids
and their esters, which are promising to be separated and
used as chemicals.
Acknowledgement
This work was supported by the SHELL Corporation.
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