Thermochimica Acta 579 (2014) 40–44

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Thermochimica Acta
journal homepage: www.elsevier.com/locate/tca

Photothermal characterization of citrus essential oils and their

derivatives
G.A. López-Muñoz a,b,∗ , J.A. Balderas-López b
a
Química Aromática SA, Río Grande S/N, Santa Catarina Acolman, Mexico State, Mexico
b
UPIBI-IPN, Av. Acueducto S/N, Barrio la Laguna Ticoman, Mexico City, Mexico

a r t i c l e i n f o a b s t r a c t

Article history: Photothermal techniques were used to study thermal diffusivity, thermal effusivity, thermal conductiv-
Received 4 September 2013 ity and specific heat of folded and non-folded citrus essential oils and their corresponding terpenes; the
Received in revised form latter are derivatives of the folding process. Experimental results show that thermal properties of all
22 December 2013
citrus essential oils are comparable. However due to a decrease on d-limonene and other monoterpenes
Accepted 10 January 2014
with the folding process, thermal properties of folded citrus oils are higher than those for unfolded citrus
Available online 30 January 2014
oils. Moreover, thermal properties of various citrus terpenes are lower than those of folded and unfolded
citrus oils. Analysis of variance (ANOVA) reveals significant differences (p < 0.05) among means for ther-
Keywords:
Citrus essential oils
mal data with the folding degree and fruit type for citrus oils. Valued obtained in this work, most of
Heat transfer them not available in the literature thus far, together with values expected to emerge from future photo-
Photoacoustic thermal calorimetric experiments, might be used in the modelling and design of distillation columns,
Photopyroelectric reboilers and heat exchangers all being parts of equipment used for citrus oils processing at industrial
Thermal diffusivity scale.
Thermal effusivity © 2014 Elsevier B.V. All rights reserved.

1. Introduction
Essential oils, major by-products of citrus juice processing; are
important flavoring ingredients in food and beverage products with
a yearly word consumption of citrus essential oils estimated in
56,200 t/year for the last decade [1]. Being complex mixtures of
chemical compounds they can be classified in to three main groups:
monoterpenes, sesquiterpenes, and oxygenates. Natural pigments
(mainly carotenoids and chlorophylls) are also present in the citrus
essential oils [2].
Essential oils are mainly obtained from the pericarp of citrus
peel by scrapping or breaking the oil cells near the fruit’s surface
and using water to drag the oil in the form of an emulsion which is
then centrifuged to obtain the cold pressed oil [3].
Citrus essential oils are mainly folded (concentrated) using high
vacuum fractional distillation [4], the monoterpenes mainly d-
limonene (the d-limonene represents on average more than the 80%
of the composition for the citrus essential oils) are partly removed
∗ Corresponding author at: Quimica Aromatica, S.A., Research and Development,
Río Grande S/N, Santa Catarina 55875 Acolman, Mexico State, Mexico.
Tel.: +52 594 1040182; fax: +52 594 1040182..
E-mail addresses: info@quimicaaromatica.com, gerardolm85@gmail.com
(G.A. López-Muñoz).
in this process, depending on the folding degree [5]. Such mixture of
d-limonene and other monoterpenes is known commercially under
the name “terpenes”.
The main folding degrees commercially available are: 2-fold to
5-fold for lime and mandarin oils, 2-fold to 10-fold for lemon and
grapefruit oils and 2-fold to 20-fold for orange oil. Folded oils are
less prone to oxidation, their solubility in water increases and they
also have high organoleptic qualities [6,7].
With the folding process, the amount of high organoleptic
sesquiterpenes (e.g. nootkatone, valencene, myrcene) and oxy-
genates (e.g. decanal, octanal, citral) in the citrus oils increases
[8]; these citrus constituents are sensitive to heat and oxidation;
the application of suitable heat transfer processes is therefore
indispensable to minimize thermal stress and thus partial decom-
position of this oil’s constituents which can result in undesired taste
and odor [1].
Thermal properties are necessary for the modeling and design
of heat transfer operations in food processing; the design of
heat transfer processes is critical, due to the heat-sensitivity of
foods. The design of heat transfer equipment depends largely
on the physical characteristics of the fluids involved, including
thermal properties like specific heat, thermal diffusivity and con-
ductivity [9–11]. The availability of the thermal properties for
citrus oils and their derivatives allow modeling and design of
heat transfer equipment (e.g. distillation columns, reboilers and

0040-6031/$ – see front matter © 2014 Elsevier B.V. All rights reserved.
http://dx.doi.org/10.1016/j.tca.2014.01.009
 G.A. López-Muñoz, J.A. Balderas-López / Thermochimica Acta 579 (2014) 40–44 41

heat exchangers), suitable forcitrus oils processing at industrial

level.
Hot wire, the laser flash and the photothermal methods are
among techniques commonly used for the determination of ther-
mal properties in liquids.
The hot wire method is a standard technique based on the mea-
surement of the temperature rise in a defined distance from a linear
heat source (hot wire) embedded in the test sample. It has been
used to determine of thermal diffusivity and conductivity of edi-
ble oils [12]. This technique is non-destructive and relative simple;
however, it requires a considerable amount of sample.
The laser flash is another conventional technique for measur-
ing thermal diffusivity and thermal conductivity mainly of solids
although it also can be used in liquids. The method is based on the
illumination of one face of the sample with a laser pulse; the tem-
perature rise on the backside of the sample due to the absorption
of the laser energy on the front place is detected in the time with
an infrared sensor [13]. This technique is non-invasive and suitable
for determinations at high temperatures; however, laser intensity
must be constant to avoid convective heat transport in liquids and
in addition the investment cost is substantial.
Finally, Photothermal techniques are widely used for determin-
ing thermal properties of liquids; for example, in the determination
of thermal diffusivity and effusivity of edible oils [14,15]. The basic
principle of these techniques relies on measuring the temperature
fluctuations in a sample as a result of the de-excitation process Fig. 1. Schematic view of the experimental set-up for photopyroelectric measure-
ments.
that takes place following the absorption of modulated radiation.
In particular, the Photoacoustic (PA) and Photopyroelectric (PPE)
techniques are non-destructive, have a moderate cost of instru- 2.2.1. Thermal diffusivity
mentation and require a small amount of sample without any The photopyroelectric experimental setup for thermal diffusiv-
previous preparation. ity measurements using sample’s thickness scan is shown in Fig. 1.
Thermal diffusivity measurements by PA techniques have been Sample’s thickness scan consists on recording the PPE signal for
previously reported for a limited number of citrus essential oils different liquid sample’s thicknesses, ls , at fixed modulation fre-
[16,17]. quency. It involves the use of a micro-linear stage to change liquid’s
This study is concerned with determination of thermal diffu- thickness in the sample’s container.
sivity and other thermophysical properties: specific heat, thermal As it has been shown elsewhere [19], the photopyroelectric
effusivity and conductivity; by PP and PA techniques for a wide (PPE) phase signal in the transmission configuration for this PPE
number of folded and unfolded citrus essential oils. setup (with fixed modulation frequency, f), in the thermally thick
regime for the liquid sample ((2f/˛s )1/2 ls > >1), is a linear function
of the sample’s thickness with the slope, B, expressed as
2. Materials and methods
 f  12
2.1. Citrus essential oil samples B= , (1)
as

The samples studied, supplied by Química Aromática
S.A.(Acolman, Mexico State, Mexico) include USP grade essen-
tial oils [18] from orange (Citrus sinensis), bitter orange (Citrus
aurantium), Persian lime (Citrus latifolia), Mexican lime (Citrus
aurantifolia), California lemon (Citrus limon), pink grapefruit (Citrus
paradise), white grapefruit (Citrus x paradise), mandarin (Citrus
reticulata blanco var. mandarin) and green mandarin (Citrus retic-
ulate) together with folded citrus essential oils: 2,4,5-fold Persian
lime, 2, 4, 5, 10-fold pink grapefruit and 2, 5, 10, 20-fold orange.
Likewise, thermal properties of samples of orange, pink grapefruit
and Persian lime terpenes derivatives of the folding process are
reported as well.
2.2. Photopyroelectric and photoacoustic methods: Theoretical
and experimental schemes
The determination of thermal diffusivity in liquids by pho-
topyroelectric method using sample’s thickness scan and the
measurement of thermal effusivity by means of the photoacous-
tic method using modulation frequency scan are well documented
[19,20].
from which the sample’s thermal diffusivity ˛s can be obtained.
The experimental procedure implies recording the PPE signal as
a function of the sample’s thickness and fit the experimental phase
to a linear model to obtain the slope B. The pyroelectric sensor is a
PVDF film (25 ␮m thickness) with metal electrodes (Ni–Al) on both
sides and accommodated in a stainless steel body. A silicon foil was
attached to the top surface of the pyroelectric sensor in order to
prevent damage to the sensor due to the liquid environment. The
resultant pyroelectric signals were processed by a lock-in ampli-
fier (Stanford Research Systems, California, USA, model SR830) for
amplification and de-modulation. Transistor–transistor logic out-
put of the lock-in was used for the modulation control of a 660 nm
laser diode system (Qioptiq Photonics Ltd., Hampshire, UK, model
IFLEX-2000) at a fixed modulation frequency of 1 Hz.
The photopyroelectric signal was recorded as a function of the
sample thickness, for 20 experimental points at 10 ␮m steps using
a micro-linear stage model T-LSM025A (Zaber Technologies, Inc.,
Vancouver, Canada). Linear fits to photopyroelectric phase were
conducted to obtain parameter B, from which, as described before,
the sample’s thermal diffusivity was obtained by means of the rela-
tion ˛s = /B2 . Measurements were repeated 10 times per sample
and performed at room temperature, or 22 ◦ C.
42 G.A. López-Muñoz, J.A. Balderas-López / Thermochimica Acta 579 (2014) 40–44

Fig. 2. Schematic view of the experimental set-up for photoacoustic measurements.

2.2.2. Thermal effusivity

The photoacoustic (PA) cell for thermal effusivity measurements
using modulation frequency scan is shown in Fig. 2. As shown else-
where [20] thermal effusivity of liquid sample can be obtained by
means of a self-normalization photoacoustic methodology. This lat-
ter implies recording the PA signal amplitude as a function of the
modulation frequency f, for a solid material (thermal diffusivity ˛m
and thickness L) in the light surface absorption model, using the
front PA configuration with liquid acting as the backing material
(␦Ps ). The PA signal (␦Pg ) from empty cell was used for normaliza- Fig. 3. Typical photopyroelectric and photoacoustic curves. >(A) Photopyroelectric
curves as a function of the sample’s thickness for deionized water, glycerol and
tion: The self-normalized PA signal amplitude is
  ethanol.(B) Photoacoustic curves as a function of modulation frequency for deion-
 ıPs  1 ized water as reference sample and without sample.

Rtt (f ) =  =  (2)
␦Pg     2
Ps
√ Ps
1+2 +2 √
f f (Qioptiq Photonics Ltd., Hamble, Hampshire, UK, model IFLEX-
2000) at a variable modulation frequency.
where
√ The photoacoustic signals were recorded as a function of the
˛m es modulation frequency from 5 to 91 Hz in 2 Hz incremental steps
Ps = √ (3)
2 L em using a stainless steel foil (30 ␮m thickness) as light’s absorber.
It is however simpler to obtain this thermal parameter when a Curve fits were made to amplitude of PA signal to obtain parameter
substance (of known thermal effusivity) is introduced. (Ps /PR ), as described before, from which sample’s thermal effusivity
was obtained from eS = (PS /PR )eR . Measurements for each sample
Ps were performed ten times at room temperature, or 22 ◦ C.
es = eR (4)
PR
√ √
where PR = ˛m × eR /2 L × em is the fitting parameter corre- 2.2.2.1. Thermal conductivity and specific heat. As shown else-
sponding to the reference liquid. where [15], the thermal conductivity and the specific heat
The PA experimental procedure for obtaining the sample’s ther- can be expressed as a function of the thermal diffusiv-
mal effusivity consists in recording the PA signal, as a function of the ity and effusivity according to: k = e·˛1/2 and c = e/˛1/2 . The
modulation frequency f for the liquid sample, the liquid reference uncertainties were estimated by using usual expressions for
sample and without the sample to carry out the self-normalized error propagation, given as k = ˛1/2 ·|e| + e·(2˛−1/2 )·|˛| and
procedure for the PA signal amplitudes and fit them to Eq. (2) to (c) = ˛−1/2 |e| + e/(2˛3/2 )|˛|, respectively.
obtain parameter P for both cases, the liquid sample and the refer-
ence liquid sample. 3. Results and discussion
The photoacoustic cell consisted of a cylindrical cavity in a stain-
less steel body connected with a commercial electret microphone Analytical grade chemicals; deionized water, glycerol and
by means of a straight round channel.The resultant photoacoustic ethanol from Sigma-Aldrich Corporation (St. Louis, MO, USA)
signals were processed by a lock-in amplifier (Stanford Research, were used as reference samples to test the operation of the
Menlo Park, CA, USA, model SR830) for amplification and de- system. The obtained thermal diffusivity and thermal effusiv-
modulation. Transistor–transistor logic output of the lock-in was ity values were 1.432 × 10−7 ± 0.003 × 10−7 cm2 s−1 , 0.159 ±
used for the modulation control of a 660 nm laser diode system 0.002 × 104 W s1/2 m−2 K−1 , 0.929 × 10−7 ± 0.04 × 10−7 cm2 s−1 ,
 G.A. López-Muñoz, J.A. Balderas-López / Thermochimica Acta 579 (2014) 40–44 43

Table 1
Thermal properties values obtained for the different citrus essential oils.

Citrus essential oil ˛ (10−7 m2 s−1 ) e (104 W s1/2 m−2 K−1 ) k (W m−1 K−1 ) c (106 J m−3 K−1 )

Orange 0.758 ± 0.003 0.048 ± 0.002 0.132 ± 0.001 1.76 ± 0.01

Bitter orange 0.762 ± 0.003 0.049 ± 0.002 0.135 ± 0.001 1.77 ± 0.01
Persian lime 0.761 ± 0.004 0.048 ± 0.003 0.132 ± 0.002 1.74 ± 0.02
Mexican lime 0.756 ± 0.003 0.049 ± 0.002 0.136 ± 0.001 1.79 ± 0.02
California lemon 0.753 ± 0.002 0.049 ± 0.003 0.134 ± 0.001 1.78 ± 0.02
White grapefruit 0.767 ± 0.003 0.048 ± 0.002 0.134 ± 0.001 1.74 ± 0.01
Pink grapefruit 0.771 ± 0.003 0.049 ± 0.003 0.137 ± 0.002 1.78 ± 0.02
Mandarin 0.769 ± 0.003 0.048 ± 0.02 0.133 ± 0.01 1.73 ± 0.01
Green mandarin 0.774 ± 0.004 0.048 ± 0.003 0.134 ± 0.002 1.74 ± 0.02

Table 2
Thermal properties values obtained for the different folded citrus essential oils and their derivative terpenes.

Citrus essential oil ˛ (10−7 m2 s−1 ) e (104 W s1/2 m−2 K−1 ) k (W m−1 K−1 ) c (106 J m−3 K−1 )

Persian lime 2× 0.765 ± 0.002 0.049 ± 0.003 0.136 ± 0.001 1.78 ± 0.01
Persian lime 4× 0.769 ± 0.002 0.051 ± 0.003 0.141 ± 0.001 1.84 ± 0.01
Persian lime 5× 0.771 ± 0.003 0.052 ± 0.002 0.143 ± 0.001 1.86 ± 0.01
Pink grapefruit 2× 0.769 ± 0.002 0.048 ± 0.003 0.135 ± 0.001 1.77 ± 0.01
Pink grapefruit 4× 0.771 ± 0.003 0.049 ± 0.004 0.137 ± 0.002 1.78 ± 0.01
Pink grapefruit 5× 0.773 ± 0.003 0.050 ± 0.003 0.138 ± 0.002 1.81 ± 0.01
Pink grapefruit 10× 0.781 ± 0.002 0.052 ± 0.003 0.145 ± 0.001 1.82 ± 0.01
Orange 2× 0.760 ± 0.002 0.048 ± 0.003 0.134 ± 0.001 1.81 ± 0.01
Orange 5× 0.764 ± 0.003 0.050 ± 0.003 0.138 ± 0.002 1.82 ± 0.02
Orange 10× 0.772 ± 0.002 0.051 ± 0.002 0.141 ± 0.001 1.86 ± 0.01
Orange 20× 0.788 ± 0.003 0.053 ± 0.002 0.147 ± 0.001 1.94 ± 0.02
Terpenes
Orange 0.734 ± 0.003 0.045 ± 0.002 0.122 ± 0.001 1.74 ± 0.01
Persian lime 0.731 ± 0.003 0.046 ± 0.002 0.125 ± 0.001 1.74 ± 0.01
Pink grapefruit 0.735 ± 0.002 0.046 ± 0.003 0.125 ± 0.001 1.73 ± 0.01

Fig. 4. Thermophysical parameters for citrus essential oils as a function of folding degree. (A) Thermal diffusivity, (B) thermal effusivity, (C) thermal conductivity and (D)
specific heat.
44 G.A. López-Muñoz, J.A. Balderas-López / Thermochimica Acta 579 (2014) 40–44
0.915 ± 0.003 × 104 W s1/2 m−2 K−1 , 0.835 × 10−7 ± 0.04 ×
10−7 cm2 s−1 and 0.621 ± 0.003 × 104 W s1/2 m−2 K−1 for deion-
ized water, glycerol and ethanol, respectively; these values are
averaged from 10 measurements and are close to data reported
in the literature [21,22]. The plots on Fig. 3 show the phase of the
photopyroelectric signal as a function of the sample thickness for
different solvents used to test the system and the amplitude of
the photoacoustic signal as a function of modulation frequency for
deionized water as a reference sample and air (empty cell).
Values for thermal diffusivity, thermal effusivity, thermal
conductivity and specific heat obtained for the different cit-
rus essential oils are summarized in Table 1. All of the values
reported are averages of 10 measurements for each sample;
for thermal diffusivity and effusivity values, the standard devia-
tion was calculated as an estimation of uncertainty. An analysis
of variance (ANOVA) by Origin Pro software (OriginLab, ver-
sion 8.6) was carried out for all the data with the following
variables: folding degree and fruit type. The ANOVA analysis
revealed significant differences (p < 0.05) among means for ther-
mal diffusivity, conductivity and specific heat data with the
folding degree and fruit type for citrus oils; however, in some
cases the analysis revealed not significant differences (p > 0.1) for
thermal effusivity data. The difference in photothermal method-
ologies (sample’s thickness scan and modulation frequency scan)
involves, of course, difference in precision on the measurements
[23].
Thermal properties of citrus essential oils are close to each other,
independently of the fruit type. This similarity is related to their
likely chemical composition; they have similar proportions of ter-
penes, sesquiterpenes and oxygenates [24].
The corresponding thermal properties obtained for different
folded citrus essential oils and their terpenes are summarized in
Table 2. All of the values reported are averages of 10 measurements
for each sample and the standard deviation was calculated as an
estimated uncertainty. Values obtained for different citrus terpenes
are close to data reported in the literature for the d-limonene, but
lower compared with the thermal properties of the different citrus
essential oils [16,17,25]. This similarity in thermal properties values
among different citrus terpenes is associated with the fact that the
d-limonene and some others monoterpenes represent more than
98% of their composition. They have lower thermal properties val-
ues compared with the sesquiterpenes and oxygenates present in
different citrus essential oils [16,17,26]. Fig. 4 shows values of ther-
mal properties for different folded citrus essential oils as a function
of the folding degree. As the folding degree increases, their ther-
mal properties values increase; this increase is due to a decrease of
mainly d-limonene and some other monoterpenes, and the increase
in the amount of sesquiterpenes and oxygenated with the folding
process.
4. Conclusions
The Photopyroelectric and Photoacoustic techniques were used
to study the thermal diffusivity, thermal effusivity, thermal con-
ductivity and specific heat of folded and non-folded citrus essential
oils and their corresponding terpenes which are derivatives of the
folding process. The values obtained in this study, most of them
unavailable in the literature so far, together with those obtained
in future photothermal calorimetric experiments, might be used
in the modeling and design of distillation columns, reboilers and
heat exchangers which are heat transfer equipment often used for
the citrus oils processing at industrial level. Experimental efforts
will now focus on the determination of thermal properties under
relevant industrial temperature conditions.
Acknowledgments
The authors acknowledge Química Aromática S.A. for financial
support to this work.
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