Appl Microbiol Biotechnol (2015) 99:611–622
DOI 10.1007/s00253-014-6242-1
MINI-REVIEW
Pyroligneous acid—the smoky acidic liquid from plant biomass
Sindhu Mathew & Zainul Akmar Zakaria
Received: 29 August 2014 / Revised: 15 November 2014 / Accepted: 17 November 2014 / Published online: 3 December 2014
# Springer-Verlag Berlin Heidelberg 2014
Abstract Pyroligneous acid (PA) is a complex highly oxy-
genated aqueous liquid fraction obtained by the condensation
of pyrolysis vapors, which result from the thermochemical
breakdown or pyrolysis of plant biomass components such as
cellulose, hemicellulose, and lignin. PA produced by the slow
pyrolysis of plant biomass is a yellowish brown or dark brown
liquid with acidic pH and usually comprises a complex mix-
ture of guaiacols, catechols, syringols, phenols, vanillins, fu-
rans, pyrans, carboxaldehydes, hydroxyketones, sugars, alkyl
aryl ethers, nitrogenated derivatives, alcohols, acetic acid, and
other carboxylic acids. The phenolic components, namely
guaiacol, alkyl guaiacols, syringol, and alkyl syringols, con-
tribute to the smoky odor of PA. PA finds application in
diverse areas, as antioxidant, antimicrobial, antiinflammatory,
plant growth stimulator, coagulant for natural rubber, and
termiticidal and pesticidal agent; is a source for valuable
chemicals; and imparts a smoky flavor for food.
Keywords Pyroligneous acid . Wood vinegar . Plant
biomass . Chemical constituents and phenolics
Introduction
Biomass production in the world was estimated to be 146
billion metric tons a year (Demirbas 2002). Currently, much of
the plant biomass especially forestry and agricultural residues
such as drift wood, corncobs, rice husks, etc. are discarded at
random or just burnt inefficiently. Burning of agricultural
S. Mathew (*) : Z. A. Zakaria
Institute of Bioproduct Development, Universiti Teknologi Malaysia
(UTM), 81310 Johor Bahru, Johor, Malaysia
e-mail: sindhumathew@hotmail.com
Z. A. Zakaria
e-mail: zainul@ibd.utm.my
residues in open fields often leads to environmental pollution
and health hazards due to the formation of aerosols (black
carbon, volatile organic carbon (VOC), semi-volatile organic
carbons (SVOC), and organic matter); trace gases like CO2,
CH4, CO, N2O, NOx, SO2, and NH3; and large amounts of
particulates (Gadde et al. 2009; Ferek et al. 1998). Polycyclic
aromatic hydrocarbons (PAHs), polychlorinated dibenzo-p-
dioxins, and polychlorinated dibenzofurans (PCDD/Fs) were
detected in gaseous-phase emissions, in the particulate matter,
and in the residual ash (Estrellan and Iino 2010). It is therefore
important to reduce the biomass waste, to curtail the environ-
mental and toxicological risks (Lemieux et al. 2004) associat-
ed with their disposal.
Pyrolysis is a thermochemical process, which results in the
thermal degradation of materials in the absence or near ab-
sence of oxygen (Balat et al. 2009). During slow pyrolysis, the
plant biomass is converted into organic vapors and solid
charcoal. The organic bonds such as C–C, H–O, C–H, and
C–O bonds are decomposed by dehydration, hydrolysis, oxi-
dation, decarboxylation, and depolymerization to produce
gaseous products, water vapor, tar, and volatiles which are
condensed and collected using filter and cold traps (Mansur
et al. 2013). The condensed organic vapors form a crude
reddish brown aqueous liquid fraction rich in oxygenated
compounds (Mathew et al., personal communication;
Mathew et al. 2014a) called pyroligneous acid (PA) or wood
vinegar, while the non-condensable vapors leave the system as
pyrolytic gases (Fig. 1). The term pyroligneous comes from
the words “pyrolysis” indicating the process involved; “lig-
nin,” one of the components of the plant biomass from which
it is derived; and the acidic nature of the liquid.
PA is commonly known as “Mokusaku-eki” in South
Korea and Japan. Interestingly, most of the work reported on
the production and application of PA has been from Asian
countries especially Japan (Yatagai et al. 2002; Watarai and
Tana 2005; Mansur et al. 2013; Imamura and Watanabe 2005),
612
Fig. 1 Schematic representation of the production of pyroligneous acid from lignocellulose-based biomass feedstocks
Korea (Lee et al. 2011; Kook and Kim 2003; Kook et al. 2002;
Choi et al. 2009; Li and Ryu 2001), China (Ma et al. 2011;
Xiwei and Enchen 2014; Xiwei et al. 2013; Wang et al. 2012,
2010; Wei et al. 2010a; Cai et al. 2012), Thailand (Baimark
and Niamsa 2009; Wititsiri 2011; Rakmai 2009; Rungruang
and Junyapoon 2010), Taiwan (Ho et al. 2013), Malaysia
(Ibrahim et al. 2013; Jain et al. 2007; Loo 2008; Mathew
et al. 2014a), Indonesia (Oramahi and Yoshimura 2013), and
few from countries such as Finland (Fagernas et al. 2012),
France (Paraud et al. 2011), Sweden, Norway (Wendin et al.
1999), Spain (Guillen and Manzanos 2002, 2005), Brazil
(Steiner et al. 2008; Petter et al. 2013; Ferreira et al. 2005),
and the USA (French 1915). Much of the work on PA in Asia
and Brazil is due to the abundance of charcoal production in
these countries (Daroit et al. 2013), while in USA and Europe,
biomass is used more for the production of bio-oil which has
higher market value, demand, and commercialization poten-
tial. In Brazil, legalization regarding the production of PA is
very generic (Daroit et al. 2013). Works on the production
and use of bio-oil, an alternative biofuel with low water
content obtained usually by fast pyrolysis of plant bio-
mass, have been extensively studied and reviewed (Kim
et al. 2012; Okutucu et al. 2011; Moraes et al. 2012;
Vitasari et al. 2011; Bridgwater 2012; Luo et al. 2004;
Appl Microbiol Biotechnol (2015) 99:611–622
Mohan et al. 2006) all across the globe due to its potential
demand in the energy market.
Plant biomass in the production of PA
Chemical composition of plant biomass
The plant biomass comprises three basic polymers, namely
cellulose, hemicellulose, and lignin, as well as inorganic min-
erals and organic extractives such as lipids, proteins, simple
sugars, starches, glycosides, alkaloids, resins, phenolics, and
essential oils (Balat et al. 2009). The plant cell wall is a
network of cellulose microfibrils interlocked and coated by
cross-linking hemicelluloses while lignin, a complex
phenylpropanoid network, is associated with hemicellulose
through arabinoxylans or galactoarabinoxylans (Mathew and
Abraham 2004). Cellulose is a homopolymer of β-(1-4)
linked glucose units, while hemicellulose is a
heteropolysaccharide composed of monosaccharides such as
glucose, xylose, mannose, galactose, arabinose, 4-O-methyl
glucuronic, or galacturonic acid residues (Carpita and
McCann 2000). Lignin is formed by the polymerization of
three hydroxyphenylpropanoid monomers namely p-
Appl Microbiol Biotechnol (2015) 99:611–622
coumaryl, coniferyl, and sinapyl alcohols (Fig. 2) that give
rise to p-hydroxyphenyl, guaiacyl, and syringyl lignin units
(Harris and DeBolt 2010).
Typically, agricultural lignocellulosic biomass comprises
40–50 % cellulose, 20–30 % hemicellulose, and 10–25 %
lignin (Iqbal et al. 2011). The proportion of these components
varies in the different plant species and accounts for the
differences in the composition of PA produced. The lignocel-
lulose contents of certain plant biomass materials that have
been used in the past and that can serve as potential raw
material for PA production are given in Table 1.
Degradation of plant biomass during pyrolysis
Increase in temperature during pyrolysis causes the depoly-
merization and fragmentation of the plant biomass compo-
nents, resulting in the production of PA. Hemicellulose de-
composes at a lower temperature range (200–320 °C), while
cellulose undergoes degradation at 280–360 °C and lignin
from 140 to 600 °C. The narrow decomposition temperature
range for cellulose is due to the homogenous, unbranched
crystalline structure of β-(1-4) linked glucose units. The
amorphous nature of xylan with many branched units that
Fig. 2 Major chemical
components in plant biomass
613
have low activation energy (Yang et al. 2007) is responsible
for the lower decomposition temperature of hemicellulose,
while the thermal stability of lignin is due to the cross-linked
aromatic molecules. At high temperatures (500 °C), the py-
rolysis vapors of xylan undergo secondary cracking and give
rise to high yields of water (Stefanidis et al. 2014).
Potential plant biomass sources for the production of PA
Besides wood and bamboo, the biomass feedstock that can be
employed for the production of PA is abundant and ranges
from agricultural residues such as straw, corncobs, sugarcane
fiber, coconut fiber, coconut shell, pistachio shell, cashew nut
shell, olive pits, peanut shells, rapeseed cake, peach pit, fruit
stone, orange peel, and rice hulls; nuts, seeds, grasses, and
aquatic plants, to forestry residues such as barks, thinnings,
pine cone, drift wood, and residues from wood-processing
industries (Wei et al. 2010a; Mathew et al. 2014b). Only
2 % of the plant cell wall-based biomass is currently utilized
by humans, and there has been an increasing interest in the
utilization of these resources in the last couple of years (Pauly
and Keegstra 2008).
614 Appl Microbiol Biotechnol (2015) 99:611–622

Table 1 Lignocellulose contents

of plant materials Lignocellulosic plant materials Cellulose (%) Hemicellulose (%) Lignin (%) References

Switch grass 45 31.4 12 Sun and Cheng 2002

Wheat straw 30 50 15 Sun and Cheng 2002
Eucalyptus 45–51 11–18 29 Alves et al. 2010
Corncobs 45 35 15 Sun and Cheng 2002
Corn stover 38 26 19 Zhu et al. 2005
Hardwood 40–55 24–40 18–25 Sun and Cheng 2002
Softwood 45–50 25–35 25–35 Sun and Cheng 2002
Tea factory waste 30.2 19.9 40.0 Demirbas 2002
Hazelnut shell 25.9 29.9 42.5 Demirbas 2002
Rice straw 41.6 31.5 12.5 Jin and Chen 2007
Sugarcane 48.6 31.1 19.1 Sanjuan et al. 2001
Miscanthus 41.9 26.6 13.3 Magid et al. 2004
Olive husk 24 23.6 48.4 Hossain et al. 2013
Nutshells 25–30 25–30 30–40 Howard et al. 2003
Banana waste 13.2 14.8 14 John et al. 2006
Barley hull 34 36 19 Kim et al. 2008
Bamboo 49–50 18–20 23 Alves et al. 2010
Olive tree 25.2 15.8 19.1 Cara et al. 2008
Empty fruit bunch 44.2 33.5 20.4 Hamzah et al. 2009
Coconut fiber 17.7 2.2 34 Dijkerman et al. 1997
Rosemary 22.8 24.7 20.5 Ma et al. 2013

Woody plant biomass and formic acid which are used commonly as coagulating
agents.
A wide range of woody biomass has been used in the past for
the production of PA. PA has been reported from oakwood
Agricultural waste biomass
(Quercus accutissima) (Lee et al. 2011), Japanese chestnut
(Castanea crenata), East Asian cherry (Prunus jamaskura)
In many parts of Brazil, rice hulls are carbonized to produce
(Kimura et al. 2002), Vitex pubescens (Oramahi and
charcoal and distillation of PA is often part of the process
Yoshimura 2013), Eucalyptus wood (Mungkunkamchao
(Steiner et al. 2008). Agricultural waste residues such as
et al. 2013), walnut (Juglans regia) tree branches (Wei et al.
walnut shells (Wei et al. 2010b); hickory shell (Cai and He
2010a), Japanese cedar (Cryptomeria japonica) (Hwang et al.
2011); Camellia oleifera shell, a by-product of tea oil process-
2005), bark free birch wood (Betula pendula) (Fagernas et al.
ing (Xu et al. 2013); and pineapple waste biomass (leaf and
2012), rubber wood (Ratanapisit et al. 2009), and mangrove
stem) left behind after the harvesting of fruit (Mathew et al.,
plant (Rhizophora sp.) (Chan et al. 2012; Jain et al. 2007; Loo
personal communication) have been used for the production
et al. 2007; Zulkarami et al. 2011).
of PA.

Bamboo biomass Herbaceous biomass

The commercial production of bamboo vinegar is being in-
creased in China and Japan owing to its diverse applications.
Zhang et al. (2003) reported the production of bamboo vinegar
by heating dried bamboo (Phyllostachys) in a charcoal kiln
with flame tunnel, at temperatures ranging from 600 to 900 °C
for 4 days. Baimark and Niamsa (2009) showed that PA from
bamboo exhibited natural rubber-coagulating property and
their antifungal efficiency was higher than that of acetic acid
Rosemary (Rosmarinus officinalis) is a well-known aromatic
evergreen shrubby herb indigenous to the Mediterranean re-
gion. The dichloromethane extract of PA from rosemary
leaves exhibited superior antioxidant characteristics with
1S-α-Pinene and Eucalyptol as major components
representing 11 % and 15.7 % of the total amount (Ma et al.
2013). Wititsiri (2011) used holy basil along with coconut coir
and coconut shell in a 1:1:1 ratio (w/w) and produced PA in a
Appl Microbiol Biotechnol (2015) 99:611–622 615

charcoal brazier, and it exhibited high pesticidal activity water in PA samples from bamboo, white popinac, eucalyptus,
against striped mealy bugs. and rubber wood. The boiling point of rubber wood PA was
reported to be in the range of 96–108 °C (Ratanapisit et al.
2009). The physicochemical properties and yield of PA from
different plant sources are given in Table 2.
Characterization of PA

Physicochemical properties of PA Chemical nature and composition of PA

PA is light yellow to dark brown and has a smoky aroma
which may differ depending on the nature of the biomass
employed. The flavor compounds, namely phenolic deriva-
tives, furan and pyran derivatives, ketones, esters, and nitrog-
enous derivatives, contribute to the aroma of PA (Guillen and
Manzanos 2005). Phenolic compounds, namely phenol (pun-
gent), alkyl phenol derivatives (pungent and cresolic flavor),
guaiacol (sweet smoky somewhat pungent), alkyl guaiacol
derivatives (sweet, smoky, woody), syringol (smoky), and
alkyl syringol derivatives (mild, heavy, burnt), contribute to
the aroma and flavor of PA (Kim et al. 1974).
PA from bark free heartwood birch consisted of 74.7 %
water and 25.3 % organic matter (Hagner et al. 2013). PA from
C. oleifera had a viscosity of 1.08 cSt and 84 % water content
(Xu et al. 2013), while Rakmai (2009) reported 78–88 %
Slow pyrolysis often results in a raw distillate which separates
into an aqueous phase termed PA and a dark non-aqueous oily
bottom phase called pyroligneous tar which also has various
applications (Amen Chen et al. 1997; Souza et al. 2012; FAO
2012; Fagernas et al. 2012). The ratio of these fractions
depends on the feedstock, process, and storage conditions
(Rakmai 2009). Due to the presence of PAHs, utilization of
tars for purposes other than energy may be difficult; however,
they can be used as wood preservatives (Fagernas et al. 2012).
The composition of PA varies depending on the heating
rate, temperature, and nature of raw material used in pyrolysis.
In general, PA comprises a complex mixture of guaiacols,
catechols, syringols, vanillins, isoeugenol, phenol, furans,
pyrans, carboxaldehydes, hydroxyketones, sugars, methanol,
acetic acid, and other carboxylic acids (Zulkarami et al. 2011;

Table 2 Physicochemical characteristics of pyroligneous acid produced from different plant sources

Biomass pH Density Organic acid content (%) Yield (%) References

Rubber wood 2.9–3.8 1.009–1.027 23–29 Ratanapisit et al. 2009

Birch heartwood 1.8–2.9 – 38–43 (including tar) Fagernas et al. 2012
Wallnut tree branches
WP1 3.49 1.034 2.73 11.4 Wei et al. 2010a
WP2 3.32 1.050 3.01 31.4
WP3 2.76 1.072 3.12 1.45
Moso bamboo 2.5 1.090 3.80 – Lin and Shiah 2006
Wallnut shell
SP1 3.02 1.013 6.31 – Wei et al. 2010b
SP2 2.98 1.045 2.85
SP3 3.32 1.035 2.07
Mixed biomass (wood+bamboo) 4.0–4.3 – – – Manu and Sangsricha 2009
Eucalyptus – – – 45.5 Souza et al. 2012
Mixed chips of Quercus sp. <2.5 – 4.6–5.5 – Choi et al. 2012
Camellia oleifera shell 3.5 – – 30 Xu et al. 2013
Rosemary leaves
Fresh – – – 65 Ma et al. 2013
Air dried – – – 25
Coconut shell 2.9 1.020 – – Wititsiri 2011
Coconut shell+coir+basil 2.5 1.030 – –
Coconut shell+basil 3.4 1.010 – –
Wallnut shell 2.81 1.443 – – Ma et al. 2011

WP1 wallnut tree branch PA collected at 90–230 °C, WP2 wallnut tree branch PA collected at 230–370 °C, WP3 wallnut tree branch PA collected at 370–
450 °C, SP1 wallnut shell PA collected at 90–150 °C, SP2 wallnut shell PA collected at 151–310 °C, wallnut shell PA collected at 311–550 °C
616
Guillen and Manzanos 2005). The dichloromethane extract of
PA from pineapple plant waste biomass had high content of
phenolic compounds especially 2,6-dimethoxy phenol, phe-
nol, 1,2-benzenediol (catechol), and 3-methoxy 1,2-
benzenediol. Phenols (69.5 %), alkyl aryl ethers (9.33 %),
and ketones (7.76 %) were identified as the major constituents
in PA from pineapple waste biomass comprising pineapple
leaf and stem remaining in the fields after the harvesting of
fruit, while furan and pyran derivatives (3.57 %), sugars
(2.85 %), acids (2.67 %), esters (1.81 %), aldehydes
(1.05 %), alcohols (0.9 %), and nitrogenous derivatives
(0.14 %) were the minor constituents (Mathew et al. 2014a).
Some of the major phenolic and non-phenolic components
detected in PA are given in Table 3.
Possible sources of origin for the chemical constituents in PA
The components in PA can be traced back to the lignocellu-
losic backbone in plant cell walls. Lactones and furans found
in PA are derived primarily from the degradation of hemicel-
lulose. Ketones and phenolic acids have been identified as the
main products from the thermal pyrolysis of xylan. These
include 1-hydroxy-2-propanone and various cyclopentenones
with methyl and ethyl substituents and simple phenols with
methyl substituents. In addition, acetic acid, propanoic acid,
and few aromatic hydrocarbons are also formed (Stefanidis
et al. 2014). Much of the acetic acid in PA comes from the
acetyl groups linked to the xylose units in hemicellulose.
Degradation of xylan yields water, methanol, acetic acid,
propionic acid, 1-hydroxy-2-propanone, 1-hydroxy-2-
butanone, and 2-furfaraldehyde. Methanol mainly arises from
the methoxyl groups of uronic acid and from the breakdown
of methyl esters or ethers from the decomposition of pectin-
like plant materials (Demirbas 2002), while some phenols are
likely to be derived from the cleavage of the ferulic acid ester
branch of xylan as well as the gas-phase polymerization of
unsaturated light species (Evans and Milne 1987).
Cellulose degradation on the other hand liberates
anhydrocellulose, levoglucosan (1,6-anhydro-β-D-glucopyra-
nose), and 1,4:3,6-dianhydro-α-D-glucopyranose (Stefanidis
et al. 2014). Under pyrolytic conditions at temperatures above
300 °C, cellulose depolymerizes to glucose followed by the
removal of a molecule of water to give rise to levoglucosan
(Balat 2008). 1,4:3,6-Dianhydro-α-D-glucopyranose could
arise by the primary pyrolysis of cellulose or by secondary
pyrolysis of levoglucosan (Kawamoto et al. 2006). Simple
phenols, cyclic ketones, aldehydes, and alcohols were also
detected in small amounts from cellulose pyrolysis (Stefanidis
et al. 2014).
Smoky flavor compounds like guaiacol, phenol, 4-methyl
guaiacol, and syringol result from the thermal degradation of
lignin (Balat 2008). Thermal decomposition of lignin results
in the cleavage of weak α-ether and β-ether bonds in lignin
Appl Microbiol Biotechnol (2015) 99:611–622
structure, releasing guaiacyl- and syringyl-type aromatics.
These aromatics further react, either by homolysis of the O–
CH3 bonds to produce catechols and pyrogallols or by radical
induced rearrangement reactions to produce cresols and
xylenols (Asmadi et al. 2011a). Further decomposition of
cresols yields phenol by demethylation (Asmadi et al. 2011b).
Pyrolysis setup for the production of PA
Several kinds of setup are employed for the production of PA
by slow pyrolysis, such as the traditional carbonization pro-
cess performed in charcoal kilns and more advanced pyrolytic
reactors (Fig. 1). Slow pyrolysis of wood resulted in the
production of char (35 %), liquid (30 %), and gas (35 %) in
nearly equal proportions (Bridgwater 2004) and will vary
depending on the feedstock, temperatures employed, heating
rate, and production technology.
Charcoal kilns
Billions of people use charcoal for cooking in developing
nations, and its large-scale production without recovery of
volatile products causes serious harm to the environment
(Kammen and Lew 2005). Generation of PA from smoke will
help to reduce the impact of carbonization on the environ-
ment. Slow pyrolysis of biomass in charcoal kiln favors char
production and is often performed in igloo-shaped masonry
kilns. The biomass feedstock such as debarked wood is
stacked in the kilns and burnt at low temperature to remove
the moisture and water content (Loo 2008). Debarking has
been reported to reduce the ash content of charcoal and
thereby improve its combustion characteristics (Hazeltine
2003). However, in studies by Fagernas et al. (2012), no such
effect was observed. This is then followed by a higher tem-
perature, at which stage the entrance of the kiln is partially
sealed to prevent complete combustion of wood. The smoke
emerging from the orifices of the kiln is allowed to pass
through collectors installed at the exit of the kiln which are
long tubes which direct the smoke towards the exit which
promotes cooling and condensation into container flasks
(Daroit et al. 2013). Jain et al. (2007) allowed the smoke from
charcoal kiln to condense by passing through a 30-m-long air-
cooled stainless steel pipe. The distillate obtained is allowed to
sediment for a few weeks and separate into PA and tar.
PA has been produced in charcoal kilns (Mathew et al.
2014a; Mungkunkamchao et al. 2013; Zhang et al. 2003)
using many plant sources. Mungkunkamchao et al. (2013)
produced PA in an iwate charcoal kiln, while Wititsiri (2011)
performed carbonization in a 200-l fuel tank as charcoal
brazier in air-closed condition to produce PA from coconut
shell, coir, and holy basil at temperatures from 300 to 400 °C.
Appl Microbiol Biotechnol (2015) 99:611–622 617

Table 3 Some of the major non-phenolic and phenolic constituents identified in PA from different plant biomass sources

Chemical class Compounds References

Aldehydes 2-Ethyl butanal Guillen and Manzanos 2005, 2005

Furan and pyran derivatives 2-Furancarboxaldehyde (furfural)
Ketones
Diketones
Carbohydrate derivatives
Alcohols, esters, and acids
Nitrogenated compounds
3-Methylbutanal (isovaleraldehyde) Guillen and Manzanos 2002, 2005
2-Butenal dimethyl acetal Mathew et al. 2014a, b
Acetaldehyde Maschio et al. 1992; Guillen and Manzanos 2005
Mungkunkamchao et al. 2013; Guillen and Manzanos 2005
4-Furancarboxaldehyde Velmurugan et al. 2009
2(5H)-Furanone (γ-crotonolactone) Guillen and Manzanos 2002; Wei et al. 2010b
Furfuryl alcohol Wang et al. 2012; Guillen and Manzanos 2005
5-Methylfurfural Guillen and Manzanos 2002; Hwang et al. 2005
3-Methyl-2(5H)-furanone Guillen and Manzanos 2002; Loo 2008
3-Hydroxy-2-methyl-4H-pyran-4-one (maltol) Wei et al. 2010a
1-Hydroxy-2-propanone Demirbas 2002
1-Hydroxy-2-butanone Wang et al. 2012; Wei et al. 2010a
3-Methyl-2-cyclopenten-1-one Guillen and Manzanos 2002; Loo 2008
2-Methyl-2-cyclopenten-1-one Marumoto et al. 2012
1-Acetoxy-propan-2-one Guillen and Manzanos 2002
2,3-Dimethyl-2-cyclopenten-1-one Wang et al. 2012
Ethanone Mungkunkamchao et al. 2013
2-Hexanone Guillen and Manzanos 2002
2-Cyclopenten-1-one Wei et al. 2010a
3-Ethyl-2-hydroxy-2-cyclopenten-1-one Wei et al. 2010a
Acetone Maschio et al. 1992
Butyrolactone Mathew et al. 2014a; Wang et al. 2012
Cyclopentanone Maschio et al. 1992; Wei et al. 2010a
1-(4-Hydroxy-3,5-dimethoxyphenyl)-ethanone Mathew et al. 2014a
3-Methyl-1,2-cyclopentanedione (cyclotene) Guillen and Manzanos 2002; Mathew et al. 2014a
2,5-Hexanedione Guillen and Manzanos 2002
3-Methyl-1,2-cyclopentanedione Mathew et al. 2014a; Wei et al. 2010a
1,6-Anhydro-β-D-glucopyranose (levoglucosan) Wei et al. 2010a
1,4:3,6-Dianhydro-α-D-glucopyranose Mathew et al. 2014a, b; Wei et al. 2010a
1,6-Anhydro-β-D-glucofuranose Fagernas et al. 2012; Guillen and Manzanos 2002
Anhydro-D-mannosan Mathew et al. 2014a
Ethyl butyrate Guillen and Manzanos 2002, 2005
Propanoic acid Mungkunkamchao et al. 2013; Wei et al. 2010b
Methyl-3-methoxy-4-acetoxybenzoate Mathew et al. 2014a
2,4-Pentanediol Guillen and Manzanos 2002
Acetic acid Yatagai et al. 2002; Mungkunkamchao et al. 2013;
Wei et al. 2010a
Pentanoic acid Guillen and Manzanos 2002; Mathew et al. 2014b
Butanoic acid Yatagai et al. 2002; Wei et al. 2010b
Dehydroacetic acid Velmurugan et al. 2009
Methanol Maschio et al. 1992; Hwang et al. 2005
Vanillic acid Maschio et al. 1992
3,6,9,12,15-Pentaoxanonadecan-1-ol Mungkunkamchao et al. 2013
Methylbenzene (toluene) Guillen and Manzanos 2002
1-Methyl-2,5-pyrrolidinedione Mathew et al. 2014a, b
618
Table 3 (continued)
Chemical class Compounds
Alkyl aryl ethers 1,2,4-Trimethoxybenzene
1,4-Dimethoxybenzene
1,2,4-Trimethoxyphenol
2,3,5-Trimethoxy toluene
Phenol and derivatives Phenol
4-Methylphenol
3-Methylphenol
2-Methylphenol
3-Ethylphenol
4-Ethylphenol
2,5-Dimethylphenol
Vanillin
Syringol and derivatives 2,6-Dimethoxyphenol (syringol)
4-Methyl-2,6-dimethoxyphenol (4-methylsyringol)
1-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propanone
(syringylacetone)
4-Vinyl-2,6-dimethoxyphenol (4-vinylsyringol)
4-Hydroxy-3,5-dimethoxy benzaldehyde (syringaldehyde)
Guaiacol and derivatives 4-Methyl-2-methoxyphenol (4-methyl guaiacol)
4-Ethyl-2-methoxyphenol (4-ethyl guaiacol)
4-Vinyl-2-methoxyphenol (4-vinyl guaiacol)
2-Methoxyphenol (guaiacol)
Pyrocatechol and derivatives 1,2-Benzenediol (pyrocatechol)
1,4-Benzenediol (hydroquinone)
3-Methyl-1,2-benzenediol
3-Methoxy-1,2-benzenediol (3-methoxypyrocatechol)
4-Methyl-1,2-benzenediol
Pyrolysis reactors
Retort ovens were used for the production of charcoal on a
commercial scale and for the recovery of by-products. The
retort process yielded 40–45 wt% distillate, 35–40 % charcoal,
and 15–25 % non-condensable gases (Antal 2003). Wei et al.
(2010a) produced PA from walnut in a vertical pyrolytic
retort, heated it up to 450 °C at 1 °C/min, and collected it at
three different temperature ranges: 90–230, 230–370, and
370–450 °C. The PA fraction obtained at 230–370 °C showed
the highest yield (Table 2) and strongest antimicrobial activity
owing to the presence of phenols and organic acids (63.4 %).
Wei et al (2010b) used a pyrolytic retort with a dimension of
130 mm (dia)×270 mm (ht) equipped with a water-cooled
condenser for the production of PA from walnut shell, while
Appl Microbiol Biotechnol (2015) 99:611–622
References
Mathew et al. 2014a; Loo 2008
Guillen and Manzanos 2002
Wei et al. 2010a
Velmurugan et al. 2009
Mathew et al. 2014a; Mungkunkamchao et al. 2013;
Velmurugan et al. 2009
Velmurugan et al. 2009; Loo 2008
Mathew et al. 2014a; Guillen and Manzanos 2005
Wang et al. 2012; Guillen and Manzanos 2002; Velmurugan
et al. 2009
Guillen and Manzanos 2002; Wei et al. 2010b
Marumoto et al. 2012
Zulkarami et al. 2011
Hwang et al. 2005; Wang et al. 2012
Mathew et al. 2014a; Fagernas et al. 2012; Zulkarami
et al. 2011
Guillen and Manzanos 2002, 2005
Guillen and Manzanos 2002, 2005
Guillen and Manzanos 2005
Loo 2008; Wei et al. 2010b
Mungkunkamchao et al. 2013; Mathew et al. 2014a;
Velmurugan et al. 2009
Guillen and Manzanos 2002; Velmurugan et al. 2009
Guillen and Manzanos 2002
Wang et al. 2012; Fagernas et al. 2012; Mungkunkamchao
et al. 2013
Fagernas et al. 2012; Mathew et al. 2014a
Wang et al. 2012; Loo 2008; Wei et al. 2010a
Wang et al. 2012
Guillen and Manzanos 2002; Wei et al. 2010b
Guillen and Manzanos 2002; Wei et al. 2010a
pyrolysis of rosemary leaves (200 g) was performed in a
pyrolysis kettle equipped with condensers (Ma et al. 2013).
Three kinds of PA were obtained based on the heating power
and temperature employed, namely PA1 (heating power
200 W, maximum temperature 310 °C), PA2 (heating power
700 W, maximum temperature 440 °C), and PA3 (heating
power 1200 W, maximum temperature 530 °C). A high yield
(60 % of the total pyrolysis products) was obtained for PA
from fresh leaves of Rosmarinus owing to the high moisture
content in them. However, the yield from air-dried leaves and
air-dried leaves after distillation of essential oil was much
lower (25 % of the total pyrolysis products) (Ma et al. 2013).
The optimum condition of pyrolysis was obtained at the
heating rate of 1.4 °C/min to a final temperature of 550 °C in a
horizontal cylindrical furnace with a yield of 27.4 % for rubber
Appl Microbiol Biotechnol (2015) 99:611–622
wood PA (Ratanapisit et al. 2009). PA collected from room
temperature to 400 °C (RW1) is reddish brown, while the one
collected above 400 °C (RW2) is dark brown because wood-
destructive reactions at higher temperature tend to increase the
tar formation. A higher heating rate was found to favor the
yields (23.2 % at 0.6 °C/min vs 29 % at 2 °C/min). Moreover,
RW1 was more acidic than RW2 as higher temperature tends
to favor phenolics and their derivatives rather than carboxylic
acids. Heating rate did not have any significant effect on pH,
specific gravity, or boiling range. Laboratory samples of
PA from Eucalyptus were produced using a muffle
furnace with a round-bottom flask and a fractionating
column inside the furnace, connected in turn to a con-
denser and glass flask to collect the PA. The furnace
was heated to 100 °C, and a gradual increase of 10 °C
was given at 10-min intervals until liquid condensation.
The physical characteristics of the distillate were found
to differ at different temperatures being colorless at
160 °C, yellow at 260 °C, and viscous black liquid at
360 °C. They separated the aqueous phase (crude PA)
from the insoluble tar by decantation process and
employed simple distillation to separate PA from soluble
tar (Souza et al. 2012). The soluble tar can also be
precipitated and separated by the addition of water
(Fagernas et al. 2012). Souza et al. (2012) obtained
91 g (45.5 % of wood mass) of PA on pyrolysing
200 g of Eucalyptus wood. This is relatively high, and
depending on the wood, it is usual to obtain 30–36 %
of condensate liquid (Amen Chen et al. 1997).
Slow pyrolysis of bark free and birch wood with
barks was performed in batch retorts at temperatures
raised up to 450 °C using thermocouples for 23 h
(Fagernas et al. 2012). The retorts were heated indirect-
ly by using a combustion chamber to heat the inner
chamber or retort in the absence of air. Distillation
began at 150 °C and tar formation commenced from
270 °C. By 400 °C, more than 80 % of the distillate
was formed and yields amounted to 38–43 % distillate,
34 % charcoal, and 18–22 % gases. Wood meals from
Vitex sp. obtained by passing through 40–60-mesh
screens and having 15 % moisture content were heated
in a closed reactor of 2-g capacity to temperatures of
350, 400, and 450 °C at a heating rate of 5 °C/min.
The smoke produced was channeled into a cooling
column through a pipeline to recover the condensed
vinegar (Oramahi and Yoshimura 2013).
Mansur et al. (2013) produced PA from Japanese cedar
wood chips by slow pyrolysis in a horizontal screw conveyor
reactor with a yield of 14 mol%. The chips had an average size
of 10×10×2 mm and 3 % moisture content. The feeding rate,
average residence time, heating rate, peak temperature, and
gas pressure in the reactor were 270 g/h, 47 s, 5–5.5 °C/s,
500 °C, and 1 atm., respectively.
619
Uses of PA
PA finds application in diverse areas. It possesses antimicro-
bial (Jain et al. 2007), antioxidant (Cai et al. 2012),
antiinflammatory (Ho et al. 2013), and antitermitic properties
(Wititsiri 2011) and can be used to improve the productivity in
agricultural crops and vegetables due to its growth-stimulating
(Mu et al. 2006) and pesticidal activity (Kim et al. 2008). It
imparts much-appreciated organoleptic properties to smoked
food (Wendin et al. 1999) and is safe to be used as animal feed
additives (Kook and Kim 2003). PA also exhibited the ability
to coagulate natural rubber due to its acidic properties (Baimark
and Niamsa 2009). Many value-added chemicals such as
syringol, catechol, acetol, levoglucosan, ketones, alcohols,
and acids can also be obtained from PA (Mansur et al. 2013;
Bridgwater 2003; Loo 2008; Scott 1989). However, there is a
lack of awareness among the public and small-scale producers
about the potential applications of PA, and delay in the imple-
mentation of standard testing procedures for monitoring the
quality of the product has kept the market demand of PA low.
Conclusion
Pyrolysis of plant biomass allows access to plant cell wall
components, and biomass conversion by pyrolysis helps in the
management of agricultural and industrial residues, providing
route for the production of PA with antioxidant, antimicrobial,
antidermatitic, pesticidal, termiticidal, and plant growth-
stimulating properties and a source for many value-added
chemicals. Moreover, the utilization of the abandoned agri-
cultural wastes could help to mitigate the environmental pol-
lution arising from their burning or disposal. Therefore, re-
search on the utilization of plant biomass, a renewable
bioresource for the production of PA with diverse applications,
has been gaining momentum over the last couple of years, and
the latest breakthroughs in thermochemical science could
increase the efficiency of utilization of lignocellulosic compo-
nents making the process more economical. More awareness
and technical know-how is required among small-scale pro-
ducers of PA. Constant quality monitoring and consistency
need to be maintained for the widespread commercialization
of PA obtained from different plant sources.
Acknowledgments The first author acknowledges the Universiti
Teknologi Malaysia (UTM) for the post-doctoral fellowship. The authors
are thankful to UTM for the Research University Grant Scheme
(Q.J130000.2509.03H84 and 06H37), and thanks are due also to the
Ministry of Higher Education (MOHE) and the Malaysian Pineapple
Industry Board for the collaboration and financial assistance (4B072
and 4B096).
Conflict of interest The authors state that there are no conflicts of
interest.
620
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