Polymer Degradation and Stability 107 (2014) 178e183

Contents lists available at ScienceDirect

Polymer Degradation and Stability

journal homepage: www.elsevier.com/locate/polydegstab

Alcoholysis of PET to produce dioctyl terephthalate by isooctyl alcohol

with ionic liquid as cosolvent
Jinyang Chen a, b, *, Jingxiao Lv a, Yimei Ji a, Junying Ding b, Xuanyu Yang a, Mihua Zou a,
Luyao Xing a
a
b

School of Environmental and Chemical Engineering, Shanghai University, Shanghai 200444, China
State Key Laboratory for Mineral Deposit Research, School of Earth Sciences and Engineering, Nanjing University, Nanjing 210093, China

a r t i c l e i n f o

a b s t r a c t

Article history:
Received 10 February 2014
Received in revised form
14 May 2014
Accepted 15 May 2014
Available online 2 June 2014

Ionic liquid (IL) as cosolvent is a new way to accelerate polymer solvation degradation, and thus several
common imidazole ILs have been studied as cosolvent to improve the alcoholysis of PET with isooctyl
alcohol (2-EH) to produce dioctyl terephthalate (DOTP) at the reux temperature (190200
C). Owing
to its best effect and relatively inexpensiveness, [Bmim]Cl has been adopted to assist the alcoholysis. Both
tetrabutyl titanate (Ti(OC4H9)4) and zinc acetate (ZA) have good catalysis for the alcoholysis, but because
ZA is solid and difcultly dissolved in alcohol and IL, it is easily to be separated out and more feasible to
be used as catalyst. With [Bmim]Cl and ZA as cosolvent and catalyst, the optimal alcoholysis of PET has
been determined to be as follows: reux temperature, reaction time 5 h, weight ratio of IL:2-EH:PET
2:2:1 and weight ratio of catalyst/PET 1.2%, and then the degradation rate of PET is almost 100% and the
yield of DOTP is 93.1%. Comparing with traditional alcoholysis without IL as cosolvent, the reaction time
decreases greatly from more than 10 h to several hours. Furthermore, the IL has been repeated four times
and the degradation rate of PET and the yield of DOTP nearly have not been changed.
2014 Elsevier Ltd. All rights reserved.

Keywords:
Waste PET
Ionic liquid
Alcoholysis
Dioctyl terephthalate
Isooctyl alcohol

1. Introduction
In recent years, with the increase of the production of polyester,
the treatment of waste PET gets more and more attention. Now the
main method of recycling of waste PET is direct physical regeneration, but the regenerating material has impurities which decrease
physical properties, therefore, new highly effective methods should
be developed. PET is composed of ester groups, which can be
cleaved by hydrolysis [1e3], alcoholysis [4e7] and aminolysis [8] to
obtain high value low molecule products. Thus, recycling of waste
PET with chemical method for recovery of some low molecules will
not only benet to the disposition of the waste solid but also obtain
commercial advantage.
Now it is known that a very excellent plasticizer of dioctyl
terephthalate (DOTP) can be produced by alcoholysis of PET with
2-EH at reux temperature [4,9e12]. But the boiling point of 2-EH

* Corresponding author. School of Environmental and Chemical Engineering,

Shanghai University, Shanghai 200444, China. Tel.: 86 21 66137729; fax: 86 21
66137725.
E-mail address: chenjy@shu.edu.cn (J. Chen).
http://dx.doi.org/10.1016/j.polymdegradstab.2014.05.013
0141-3910/ 2014 Elsevier Ltd. All rights reserved.

at the atmospheric pressure is about 180
C and the efciency of

alcoholysis is very low. In order to increase efciency, we studied
alcoholysis of PET with sub- and supercritical 2-EH. Although it is a
very effective method [13], the need of high pressure vessel is a
disadvantage to industrial application. Thus, it is necessary to
develop a new method at the atmospheric pressure for the alcoholysis of PET to produce DOTP.
The method of cosolvent is a new way to accelerate chemical
reaction and addition some cosolvents to 2-EH can change solution
characteristics [14] to improve its reaction efciency. For example,
as for the alcoholysis of plant oil, the efciency increases greatly
when adding some water into the system [15]. Recently ionic liquids (ILs) have been extensively used as solvents in the degradation
of waste polymers because of their characteristics of chemical and
thermodynamic stability, non-volatility, strong dissolving ability
and so on [16e18]. The physical and chemical characteristics of ILs
can be easily adjusted with choice of composition of different ions
to change mutual solubility with other solvents and even to play
catalytic role to increase reaction rate and selectivity. In addition,
the non-volatility of ILs can reduce vapor pressure of the whole
mixed system and increase the reux temperature. Liu et al. studied
hydrolysis of PET with mixture of ionic liquid [Bmim]Cl and water,

J. Chen et al. / Polymer Degradation and Stability 107 (2014) 178e183

179

and then PET was efciently hydrolyze at the temperature of

150e170
C, whereas if without [Bmim]Cl the hydrolysis rate
decreased from 100% to 20% [19]. Recently Nunes et al. reported
that robust conversion of 98 wt% from PET to diethylterephthalate
(DET) with supercritical ethanol was obtained by adding [Bmim]
[BF4] as catalyst, accompanied by reduction of depolymerization
time from ca. 6 h to 45 min [20].
Therefore, in order to enhance the alcoholysis efciency of PET
with 2-EH at reux temperature under the atmosphere pressure,
we studied ILs to mix with 2-EH as cosolvent for improving the
alcoholysis. Up to date, the type of ILs with imidazole cation have
been studied to have excellent effect on the degradation of PET to
high value low molecules [19e23]. Thus in the study, several
imidazole ILs were studied with 2-EH to alcoholyze PET to produce
DOTP.
2. Experimental
2.1. Materials
The sample of PET slice (diameter 2 mm) was obtained from
Tianjin Letai chemical industry Co. LTD (Tianjin, China). PET
was cleaned with distilled water and heated at 318 K for 12 h
before use. Anhydrous 2-EH, DOTP, zinc acetate (ZA), tetrabutyl
titanate (Ti(OC4H9)4), N-methylimidazolium, 3-chloropropene,
1-chlorobutane and 1-bromobutane were purchased from Sinopharm Chemical Reagent Co. LTD (Shanghai, China). All reagents
were used as purchased without further purication.
ILs [Amim]Cl, [Bmim]Cl and [Bmim]Br were prepared with onestep as the equations shown in Fig. 1. ILs [Bmim]BF4, [Bmim]PF6,
[Bmim]NO3, [Hmim]CF3SO3 and [Bsmim]HSO4 (1-Sulfobutyl-3methylimidazolium hydrogen sulfate) were purchased from
Shanghai Cheng Jie Chemical Co. LTD (China).

Fig. 2. The schematic diagram of the alcoholysis process.

2.3. Analysis of alcoholysis products

After alcoholysis reaction, the residual solid phase was separated from the liquid phase and washed with distilled water to
obtain residual PET. The degradation rate of PET is dened by
Eq. (1):

Degradation rate percentage of PET W0  Wt =W0  100%

(1)

2.2. Alcoholysis of PET

The schematic diagram of the reaction equipment for the alcoholysis of PET is shown in Fig. 2. The alcoholysis reaction was at
atmospheric pressure using a 100 mL round-bottom three-necked
ask equipped with a thermometer and a reux condenser. At the
reux temperatures of 190200
C, the solvent and reactant of 2EH and product of ethylene glycol (EG) will be reuxed. The densities of 2-EH and EG are 0.84 and 1.12, respectively, and owing to
the immiscibility of the two compounds, the mixture will become
two levels with heavy EG at the bottom. Thus, the reux product of
EG in the condenser of Fig. 2 will separate to the bottom of reux
vessel and it can be discharged to the alcoholysis reaction. Then the
reactant of 2-EH is reuxed to reaction system to cause the alcoholysis of PET to produce DOTP.

where W0 is the initial weight of PET and Wt is the weight of residual PET.
Meanwhile, the liquid products were added distilled water to
wash out water-soluble components such as EG and IL. Then the oil
phase was distilled to remove the 2-EH and the residual liquid was
analyzed by HPLC to give amount of DOTP. The measuring condition
is the same described in the former paper [13]. The yield of DOTP is
dened by Eq. (2):

Yield percentage of DOTP Wt =W0  100%

(2)

where W0 is the initial weight of PET and Wt is the weight of

DOTP.
2.4. Separation of the IL and DOTP

Fig. 1. Preparation equations of the ILs.

Owing to high price, non-volatility and thermal stability of ILs,

the IL should be recycled. After the ltrate of residual solid PET and
catalyst, the liquid phase mainly containing ethylene glycol, 2-EH,
IL and DOTP were added deionized water to wash out water-soluble
components such as ethylene glycol and ionic liquid. Then the IL
was recovered from the water-soluble liquid phase with reduced
pressure distillation to evaporate water, ethylene glycol and residual volatile impurity. The IL after recycling was analyzed by FTIR
and 1H NMR as the former paper [13].
The residual liquid products after removal of water-solubility
components and 2-EH were further puried by SiO2 column
chromatograph to obtain pure DOTP. The puried liquid DOTP was
analyzed by FTIR and 1H NMR as the former paper [13].

180

J. Chen et al. / Polymer Degradation and Stability 107 (2014) 178e183

3. Results and discussions

Table 2
The alcoholysis of PET with different catalystsa.

3.1. Selection of ILs

Based on recent studies [19e23], several common imidazole ILs
were selected as cosolvent with 2-EH to alcoholyze PET and the
result was given in Table 1. Owing to the complex intermolecular
effects of PET, the benet to destroy the effects will facilitate the
dispersion of PET in the liquid and alcoholysis. As for the several
anions of ILs (Cl, Br, NO-3, CF3SO-3, HSO-4, BF4 and BF6), the diffusion into solid PET will benet to the dispersion. Halogen has less
molecular size and more electronegativity, thus they are easy
penetration into the solid PET to cause the dispersion, thus halogen
ILs ([Amim]Cl, [Bmim]Cl and [Bmim]Br) greatly accelerate the
alcoholysis and [Bmim]PF6 has the worst result.
Cl has stronger electronegativity than Br, so the IL of [Bmim]Cl
has a little better effect than [Bmim]Br. As for [Amim]Cl and [Bmim]
Cl with almost same effect, the preparing materials of 3chloropropene and 1-chlorobutane for the [Amim]Cl and [Bmim]
Cl, 1-chlorobutane is cheaper. Therefore, [Bmim]Cl is more feasible
as cosolvent with 2-EH to enhance alcoholysis of PET and it is
adopted in the following studies.
3.2. Catalyst
In order to improve alcoholysis efciency, some catalysts should
be used. It is known that Ti(OC4H9)4 and ZA have excellent catalytic
effect on the alcoholysis of PET. The result of the two compounds is
shown in Table 2 and both of them have good acceleration of the
alcoholysis. The degradation rate of PET increases to more than 95%
from 57% and the corresponding yield of DOTP increases to more
than 85% from 43% with them as catalyst.
Ti(OC4H9)4 is liquid and will cause difcult to the separation of
products and recycle of IL, whereas ZA is solid and difcultly dissolved in alcohol and IL. Thus ZA is easy to be separated from the
products and IL and more feasible to be used as catalyst. In addition,
ZA is cheaper and with it as catalyst the cost of the process can be
decreased. Then ZA is used in the following studies as catalyst.
The different dosages of ZA are studied to obtain appropriate
amount at the reux temperature (190200
C), 4 h and weight
ratio of IL: 2-EH: PET 2:2:1. The degradation rate of PET and yield of
DOTP are given in Fig. 3. It shows that with increasing dosage of ZA,
the alcoholysis of PET to DOTP is improved.
The weight ratio of catalyst/PET increases from 0.3 to 1.2%, the
degradation rate of PET increases from 60 to 96% and the corresponding yield of DOTP from 46 to 85%. Whereas when the dosage
increases from 1.2% to 2.1%, the degradation rate of PET and yield of
DOTP increase very little, thus the appropriate dosage of ZA is 1.2%
of the weight ratio of ZA/PET.

Catalyst

Degradation rate of PET (%)

Yield of DOTP (%)

e
Ti(OC4H9)4
ZA

57.3
98.1
97.5

43.2
86.7
85.9

a
Reaction conditions: reux temperature, 4 h, weight ratio of IL: 2-EH: PET 2:2:1
and weight ratio of catalyst/PET 1.2%.

3.3. The weight ratio of IL/2-EH

The 2-EH is both reactant and solvent for the alcoholysis of PET.
Because the viscosity of ionic liquid is very high, the low content of
2-EH will result in disadvantage of alcoholysis owing to high viscosity. In addition, as a reactant, 2-EH should be increased to a
certain level to benet the reaction. Whereas when the content of
2-EH is high and the IL is low, it will be disadvantageous to destroy
the interactions of PET molecular and result in difcult dispersion
of PET into liquid phase to slow down its alcoholysis. Therefore, the
appropriate ratio of IL/2-EH should be determined.
Fig. 4 gives the effect of different weight ratio of IL/2-EH on the
alcoholysis of PET to DOTP at the reux temperature (190200
C),
4 h, weight ratio of 2-EH/PET 2 and weight ratio of catalyst/PET
1.2%. It shows that with the increase of weight ratio from 0.25 to
0.75, the degradation rate of PET increases from 70 to 90% and the
corresponding yield of DOTP from 58 to 85%. When the weight ratio
increases to 1, both the degradation rate and yield of DOTP attain
the maximum. Whereas with increasing weight ratio further, both
the degradation rate and yield of DOTP decrease. According to the
result, the weight ratio of IL/2-EH 1 is appropriate and the higher or
the lower weight ratio is disadvantage to the alcoholysis of PET to
obtain DOTP.
3.4. Weight ratio of 2-EH/PET
The weight ratio of 2-EH/PET has effect on the cost of the process and the higher treatment of PET is more efcient. The result of
alcoholysis of PET with weight ratio of 2-EH/PET is given in Fig. 5 at
the reux temperature (190200
C), 4 h, weight ratio of IL/PET 2
and weight ratio of catalyst/PET 1.2%. It shows that the degradation
rate of PET and yield of DOTP increase with the increase of weight
ratio of 2-EH/PET at relative low value, that is, when the weight

Table 1
The alcoholysis of PET in different ILsa.
IL

Degradation rate of PET (%)

Yield of DOTP (%)

e
[Amim]Cl
[Bmim]Cl
[Bmim]Br
[Bmim]NO3
[Hmim]CF3SO3
[Bsmim]HSO4
[Bmim]BF4
[Bmim]PF6

1.7
56.1
57. 3
46. 2
10.5
5.2
28.6
4.3
3.7

1.2
42.4
43.2
37.3
6.5
3.7
20.5
3.1
2.2

a
Reaction conditions: reux temperature, 4 h, weight ratio of ionic liquid: 2-EH:
PET 2:2:1.

Fig. 3. The result of the alcoholysis of PET with the weight ratio of catalyst/PET (reux
temperature, 4 h, weight ratio of IL: 2-EH: PET 2:2:1).

J. Chen et al. / Polymer Degradation and Stability 107 (2014) 178e183

181

Fig. 4. The result of the alcoholysis of PET with the weight ratio of IL/2-EH (reux
temperature, 4 h, weight ratio of IL: PET 2:1 and weight ratio of catalyst/PET 1.2%).

Fig. 6. The result of the alcoholysis of PET with reaction time (reux temperature, 4 h,
weight ratio of IL: 2-EH: PET 2:2:1 and weight ratio of catalyst/PET 1.2%).

ratio of 2-EH/PET increases from 1.0 to 2.0, the degradation rate of

PET and yield of DOTP increase greatly. Whereas when the weight
ratio of 2-EH/PET increases from 2.0 to 3.0, the increase of degradation rate of PET and yield of DOTP is very little. Owing to the little
change of degradation rate of PET and yield of DOTP with increasing
weight ratio more than 2, the weight ratio of 2-EH/PET of 2 is
appropriate with considering the process cost.

95% at 6 h. The difference of reaction time on the degradation rate

and yield of DOTP is resulted from that PET is rstly degraded to
oligomers and then the oligomers degraded to DOTP.
With increasing time further after 6 h, the yield of DOTP decreases, which should be the result that the longer time will result
in decomposition of DOTP. Thus, the optimal time to obtain DOTP
should be no longer than 6 h. Therefore, if the degradation rate of
PET, yield of DOTP and the time cost are considered, the appropriate
reaction time should be 5 h.

3.5. Reaction time

At the reux temperature 190200
C, the weight ratio of IL:2EH:PET 2:2:1 and weight ratio of catalyst/PET 1.2%, the alcoholysis
of PET with time is given in Fig. 6. It shows that with increasing
time, the degradation rate of PET and yield of DOTP increase at
relatively short time. At the time of 4 h, the degradation rate of PET
is almost 98%, but the yield of DOTP is only 85%. With increasing
time further, the degradation rate has very little change, but the
yield of DOTP increases to 93% at 5 h and attains the maximum of

Fig. 5. The result of the alcoholysis of PET with the weight ratio of 2-EH/PET (reux
temperature, 4 h, weight ratio of IL/PET 2:1 and weight ratio of catalyst/PET 1.2%).

Table 3
The reusability results of ILa.
Recycle

Degradation rate of PET (%)

Yield of DOTP (%)

98.1
86.8

97.6
85.1

97.8
87.1

98.0
85.9

a
Reaction conditions: reux temperature, 4 h, weight ratio of IL: 2-EH: PET 2:2:1
and weight ratio of catalyst/PET 1.2%.

Fig. 7. The IR spectral of the IL of no use and recovery.

182

J. Chen et al. / Polymer Degradation and Stability 107 (2014) 178e183

Fig. 8. The 1H NMR spectrum of the recovered IL after 4 times.

3.6. Reusability of IL
The recovered IL was directed reused and the results of the
degradation of PET and yield of DOTP are shown in Table 3. It shows
that the recovered IL remains good activity at least four times in the
study.
In order to understand if the structure and composition of the
recovered IL had been changed, the recovered IL after 4 times was
analyzed by FTIR and 1H NMR. The IR spectral of no use and the
recovery are given in Fig. 7 and the result shows that the two
spectral are almost the same. Fig. 8 is the 1H NMR spectrum of the
recovered IL. Except that the peak of d7.34 ppm is the solvent CDCl3,
the peaks of d0.94e0.98 (A), 1.34e1.43 (B), 1.87e1.95 (C), 4.13 (F),
4.32e4.36 (D), 7.52 (G), 7.68 (H) and 10.62 (E) ppm are accorded
with the molecular structure of the IL [Bmim]Cl.
According to the FTIR and 1H NMR, it can conclude that the
recovered IL is almost not changed with high stability and purity,
indicating that the recycling of the IL in the process is completely
feasible.
3.7. Separation and purication of DOTP
In the process, the catalyst of ZA is solid and easily separated by
ltration. The IL and one product of EG are water-solubility and can
be extracted with washing of water. Then the oil phase is distilled to
remove the 2-EH and further puried by SiO2 column chromatograph to obtain pure DOTP. As for the puried DOTP, the FTIR and 1H
NMR spectrum are almost the same of former paper [13] and the
result indicates that the puried DOTP is pure DOTP. Thus the DOTP
obtained from waste PET alcoholysis of the process can be used as
with DOTP produced from common chemical materials.
4. Conclusions
The imidazole IL [Bmim]Cl can assist PET alcoholysis by 2-EH as
cosolvent to obtain DOTP and the IL can be recycled to reduce
process cost. With ZA as catalyst, the yield of DOTP can attain 93% at
reux temperature, 5 h, weight ratio of IL: 2-EH: PET 2:2:1 and
weight ratio of catalyst/PET 1.2%, and the degradation rate of PET is

almost 100%. The method with ILs as cosolvent has greatly higher
efciency than the traditional reux temperature alcoholysis of PET
without ILs because the similar result obtained from the traditional
method should have at least 10 h.
Comparing with the former method [13] about alcoholysis of
PET with sub-critical 2-EH to produce DOTP, although its efciency
is slightly lower, the mild reaction condition at the atmospheric
pressure without need of high pressure cause it more feasible to
industrial application. Thus the method is a high efcient way for
industrial application to obtain high value plasticizer by chemical
recovery of waste PET.
In addition, the imidazole IL is very common and relatively
inexpensive, which is also an important advantage to cause the
method feasible to industrial application because high cost of ILs is
indeed an great disadvantage for the application recently.

Acknowledgments
This research was supported by the National Natural Science
Foundation of China (No. 20777048), the Program for Innovative
Research Team in University (No. IRT13078), and the Opening
Project of State Key Laboratory for Mineral Deposit Research (No.
17-1112-9).

References
[1] Carvalho GM, Muniz EC, Rubira AF. Hydrolysis of post-consume poly(ethylene
terephthalate) with sulfuric acid and product characterization by WAXD, 13C
NMR and DSC. Polym Degrad Stab 2006;91:1326e32.
[2] Wan BZ, Kao CY, Cheng WH. Kinetics of depolymerization of poly(ethylene
terephthalate) in a potassium hydroxide solution. Ind Eng Chem Res 2001;40:
509e14.

[3] Gl G, Yalnyuva T, Ozgms

S, Orbay M. Simultaneous glycolysis and
hydrolysis of polyethylene terephthalate and characterization of products by
differential scanning calorimetry. Polymer 2003;44:7609e16.
[4] Pingale ND, Palekar VS, Shukla SR. Glycolysis of postconsumer polyethylene
terephthalate waste. J Appl Polym Sci 2010;115:249e54.
[5] Pardal F, Tersac G. Comparative reactivity of glycols in PET glycolysis. Polym
Degrad Stab 2006;91:2567e78.
[6] Pardal F, Tersac G. Kinetics of poly(ethylene terephthalate) glycolysis by
diethylene glycol. I. Evolution of liquid and solid phases. Polym Degrad Stab
2006;91:2840e7.

J. Chen et al. / Polymer Degradation and Stability 107 (2014) 178e183

[7] Pardal F, Tersac G. Kinetics of poly(ethylene terephthalate) glycolysis by
diethylene glycol. Part II: effect of temperature, catalyst and polymer
morphology. Polym Degrad Stab 2007;92:611e6.
[8] Zenda K, Funazukuri T. Depolymerization of poly(ethylene terephthalate) in
dilute aqueous ammonia solution under hydrothermal conditions. J Chem
Technol Biotechnol 2008;83:1381e6.
[9] Troev K, Grancharov G, Tsevi R, Gitsov I. A novel catalyst for the glycolysis of
poly(ethylene terephthalate). J Appl Polym Sci 2003;90:1148e52.
[10] Dupont LA, Gupta VP. Degradative transesterication of terephthalate polyesters to obtain DOTP plasticizer for exible PVC. J Vinyl & Addit Technol
1993;15:100e4.
[11] Shukla SR, Kulkarni KS. Depolymerization of poly(ethylene terephthalate)
waste. J Appl Polym Sci 2002;85:1765e70.
[12] Shukla SR, Harad AM. Glycolysis of polyethylene terephthalate waste bers.
J Appl Polym Sci 2005;97:513e7.
[13] Liu F, Chen J, Li Z, Ni P, Ji Y, Meng Q. Alcoholysis of poly(ethylene terephthalate) to produce dioctyl terephthalate with sub- and super-critical isooctyl alcohol. J Anal Appl Pyrolysis 2013;99:16e22.
[14] Ono T, Kobayashi S, Hoshina T, Sato Y, Inomata H. Volumetric behavior and
solution microstructure of methanolewater mixture in sub- and supercritical
state via density measurement and MD simulation. Fluid Phase Equilibria
2010;302:55e9.
[15] Vieitez I, Silva C, Alckmin I, Borges GR, Corazza FC, Oliveira JV, et al. Continuous catalyst-free methanolysis and ethanolysis of soybean oil under supercritical alcohol/water mixtures. Renew Energy 2010;35:1976e81.

183

[16] Kamimura A, Yamamoto S. An efcient method to depolymerize polyamide

plastics: a new use of ionic liquids. Org Lett 2007;9:2533e5.
[17] Wang H, Li Z, Liu Y, Zhang X, Zhang S. Degradation of poly(ethylene terephthalate) using ionic liquids. Green Chem 2009;11:1568e75.
[18] Wang J, Li C, Wang Z, Li Z, Jiang Y. Vapor pressure measurement for water,
methanol, ethanol, and their binary mixtures in the presence of an ionic liquid
1-ethyl-3-methylimidazolium dimethylphosphate. Fluid Phase Equilibria
2007;255:186e92.
[19] Liu F, Cui X, Yu S, Li Z, Ge X. Hydrolysis reaction of poly(ethylene terephthalate) using ionic liquids as solvent and catalyst. J Appl Polym Sci
2009;114:3561e5.
[20] Nunes CS, da Silva MJV, da Silva DC, dos Reis Freitas A, Rosa FA, Rubira AF,
et al. PET depolymerisation in supercritical ethanol catalysed by [Bmim][BF4].
RSC Adv 2014;4:20308e16.
[21] Wang H, Yan R, Li Z, Zhang X, Zhang S. Fe-containing magnetic ionic liquid as
an effective catalyst for the glycolysis of poly(ethylene terephthalate). Catal
Commun 2010;11:763e7.
[22] Wang H, Liu Y, Li Z, Zhang X, Zhang S, Zhang Y. Glycolysis of poly(ethylene
terephthalate) catalyzed by ionic liquids. Eur Polym J 2009;45:1535e44.
[23] Kamber NE, Tsujii Y, Keets K, Waymouth RM, Pratt RC, Nyce GW, et al. The
depolymerization of poly(ethylene terephthalate) (PET) using N-heterocyclic
carbenes from ionic liquids. J Chem Educ 2010;87:519e21.