Thermal Stability of 4-tert-Butyl Diphenyl Oxide

Article abstract of DOI:10.1134/S0036024419110244

Abstract: In the temperature range of 703–763 K, the thermal stability of 4-tert-butyl diphenyl oxide (4?TBDPO) has been studied, the components of the thermolysis reaction mass have been identified, a kinetic model of the process has been proposed, and the rate constants and parameters of the Arrhenius equation for all reactions under consideration have been calculated. The predominant role of isomerization transformations of 4-TBDPO has been found. A mechanism for the radical isomerization of the tert-butyl substituent has been proposed.

Full text of DOI:10.1134/S0036024419110244

ISSN 0036-0244, Russian Journal of Physical Chemistry A, 2019, Vol. 93, No. 11, pp. 2123–2130. © Pleiades Publishing, Ltd., 2019.
Russian Text © The Author(s), 2019, published in Zhurnal Fizicheskoi Khimii, 2019, Vol. 93, No. 11, pp. 1644–1651.
ON THE 90th ANNIVERSARY OF THE DEPARTMENT
OF CHEMISTRY OF THE LOMONOSOV MOSCOW STATE UNIVERSITY
Thermal Stability of 4-tert-Butyl Diphenyl Oxide
V. A. Shakuna,*, T. N. Nesterovaa, S. V. Tarazanovb, and S. A. Spiridonova
a Samara State Technical University, Samara, 443100 Russia
b All-Russian Research Institute of Oil Refining, Moscow, 111116 Russia
*е-mail: ShakyH@mail.ru
Received February 11, 2019; revised February 11, 2019; accepted May 14, 2019
Abstract―In the temperature range of 703–763 K, the thermal stability of 4-tert-butyl diphenyl oxide
(4-TBDPO) has been studied, the components of the thermolysis reaction mass have been identified, a
kinetic model of the process has been proposed, and the rate constants and parameters of the Arrhenius equa-
tion for all reactions under consideration have been calculated. The predominant role of isomerization trans-
formations of 4-TBDPO has been found. A mechanism for the radical isomerization of the tert-butyl substit-
uent has been proposed.
Keywords: 4-tert-butyl diphenyl oxide, thermal stability, thermal degradation, isomerization, kinetics
DOI: 10.1134/S0036024419110244
Diphenyl oxide (DPO) and its alkyl derivatives are the mutual transformations of thermolysis products,
and it has been shown that the isomerization of
4-TBDPO plays a decisive role in the decomposition
process.
of scientific interest and of great practical importance
in the development of modern industry.
It is well known that DPO mixed with biphenyl is
used as a high-temperature coolant [1, 2]. Based on
DPO derivatives, polymers are created that possess
unique mechanical and optical properties [3]; some of
alkyl DPOs, including those containing C4 substitu-
ents, exhibit the properties of liquid crystals [4].
This information is of great importance in the
research and development of thermostable and heat-
resistant polymers. It is known [11] that aromatic
polyethers have high thermal stability and heat resis-
tance, and the presence of an alkyl substituent in the
core gives the polymer additional properties; for
example, an increased glass transition temperature.
Polyphenylene oxides and their alkyl derivatives are
used at temperatures up to 623 K; therefore, the results
obtained are relevant for developing understandings of
their properties.
However, information on the thermal stability of
diphenyl oxide and its derivatives is limited. The most
extensive studies [5, 6] have been devoted to determin-
ing the initial temperatures and minimum decomposi-
tion energies of alkyl aromatic esters in order to deter-
mine promising hydraulic fluids and lubricants.
EXPERIMENTAL
Recently, interest has increased in the study of the
thermal stability of alkylbenzenes in the production of
promising fuels. Among other compounds, much
attention is paid to butylbenzenes [7–10] as model
structures. These studies are united by the fact that in
reactors of various materials (gold, steel, and glass) in
the temperature range 500–800 K, the decay of n-but-
Starting materials. 4-TBDPO was synthesized, iso-
lated, and purified according to the known procedure
[12]. The concentration of the main substance was
99.93 wt % according to GLC.
Procedure for studying 4-TBDPO thermolysis.
Thermolysis was studied in the gas phase in glass cap-
illaries (l = 23–25 mm; dn = 0.95–1.05 mm) made of
ylbenzene (NBB) and tert-butylbenzene (TBB) by the Pyrex, in which the test substance was placed. The
capillary was flushed with helium (purity 99.999%)
and sealed. The degree of filling was 25–27% of the
volume, which corresponded to a substance mass of
0.8–1.0 mg. Samples were weighted on an Shimadzu
AUW 120D analytical balance with an accuracy of
10‒4 g. The capillary with the substance was thermo-
statted in a laboratory pyrolysis furnace, which
radical mechanism was accompanied by the formation
of sec-butylbenzene (SBB) and isobutylbenzene
(IBB), respectively.
In this work, 4-tert-butyl diphenyl oxide
(4-TBDPO) was chosen as the object of study as a
compound that combines the properties of alkylarenes
and aromatic ethers. We have carried out an analysis of ensured the accuracy of maintaining the temperature
2123

2124
SHAKUN et al.
5
−
I × 10
9 10
22
20
18
16
14
12
10
8
Solvent
373 К
473 К
5 К/min
5
8
Standard
7
1
6
6
4
11121314
22 24
2
4
2
3
2
4
6
8
10
12
14
16
18
20
26
28
30 32
τ, min
Fig. 1. Chromatogram of the mixture of products of the 4-TBDPO thermal decomposition (T = 728 K, t
= 40 min): (1) phe-
cont
nol, (2) 4-tert-butylphenol (4-TBP), (3) 4-isobutylphenol (4-IBP), (4) diphenyl oxide (DPO), (5) 4-methyldiphenyl oxide
(4-MeDPO), (6) 4-ethyl diphenyl oxide (4-EDPO), (7) 4-isopropyl diphenyl oxide (4-IPDPO), (8) 4-n-propyl diphenyl oxide
(4-NPDPO), (9) 4-tert-butyl diphenyl oxide (4-TBDPO), (10) 4-isobutyl diphenyl oxide (4-IBDPO), (11–14) undefined com-
ponents X –X .
1
4
in the isothermal zone to be 1 K; the device was pre- (30 m × 0.25 mm × 0.25 μm) and an Agilent 5975C
viously reported [13]. The time to reach the isothermal VL MSD mass-selective detector. The reaction prod-
mode after the capillary was placed in the furnace did ucts were identified using the rules and approaches
not exceed 60 s. The pyrolysis process was completed described by Lebedev [14], Pretsch, Buhlmann, and
by quenching in a tube cooled to –15°С. The thermal Affolter [15] as well as data from the NIST 2017 library
stability of 4-TBDPO was studied in the temperature [16].
range 703–763 K with a step of 5 K. The conversion of
4-TBDPO did not exceed 25%; the number of moles
in the process increased by no more than 5%.
The identity of 4-IBDPO (10) was approved by the
synthesis of its sample. 4-IBDPO was obtained by the
Würz–Fittig reaction from 4-bromodiphenyl ether
and isobutyl bromide on sodium chips in n-hexane at
room temperature. 4-Bromodiphenyl ether was
obtained by bromination of DPO with liquid bromine
at room temperature; the DPO/Br2 ratio was
20/1 mol/mol. The retention time of synthesized
4-IBDPO corresponded to component (10) in Fig. 1.
Overlaying chromatograms are not given because this
reduces the information content.
Alkyl DPOs have no positional isomers and were
identified in accordance with the rules for the deter-
mination of alkyl aromatic structures [14, 15]. 4-TBP
was identified by comparing its retention time with the
standard sample. 4-IBP was identified by comparing
the retention times and mass spectra of component (3)
and 4-n-butylphenol (>98 wt % according to GLC),
which was added to the mixture to be analyzed.
Analysis and identification of components of the
thermolysis reaction mixture. GLC was used as the
main method for the analysis of reaction mixtures.
The analysis was performed on a Crystal 2000 M chro-
matograph equipped with a SE-30 quartz capillary
column (60 m × 250 μm × 0.25 μm). The temperature
profile of the analysis is shown in the chromatogram
(Fig. 1). The temperature of the evaporator was
250°С, while that of the detector was 280°С.
A quantitative analysis of the composition of the
reaction mixture was performed by the internal stan-
dard method using n-С20Н42 as the internal standard
(98.0 wt % according to GLC), the value of the cali-
bration coefficient with respect to 4-TBDPO was
0.9625 0.067.
Identification of the components of the mixtures
included directed chemical synthesis and chromatog-
raphy-mass spectrometric analysis (70 eV) performed
on an Agilent 6850 gas chromatograph equipped with
an HP-5MS Agilent 19091S-433E capillary column
In the reaction mass, under conditions of deep
conversion, trace amounts (>0.1 mol %) of isopropyl-
benzene and tert-butylbenzene were also observed.
The concentration of unidentified components X1–X4
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THERMAL STABILITY OF 4-tert-BUTYL DIPHENYL OXIDE
2125
Table 1. Characterization of mass spectra of the reaction mass of thermolysis of 4-TBDPO
Compound
Mass spectrum 70 eV (m/z, intensity, rel. %)
Phenol
94 (M+, 100), 66 (46), 39 (43)
4-TBP
150 (M+, 23), 135 (100), 107 (42), 91 (10), 77 (10)
4-IBP
150 (M+, 14), 107 (100), 91 (1), 77 (12)
DPO
170 (M+, 45), 141 (72), 115 (26), 94 (4), 77 (60)
4-МеDPO
4-EDPO
4-IPDPO
4-NPDPO
4-TBDPO
4-IBDPO
Х1
184 (M+, 100), 169 (4), 141 (15), 91 (100), 77 (50)
198 (M+, 58), 183 (100), 169 (5), 153 (10), 105 (16), 91 (15), 77 (57)
212(M+, 37), 197 (100), 178 (4), 169 (2), 119 (6), 104 (14), 91 (36), 77 (38)
212(M+, 32), 183 (100), 165 (1), 153 (8), 107 (8), 91 (6), 77 (35)
226 (M+, 31), 211 (100), 183 (6), 171 (1), 165 (2), 91 (8), 77 (12)
226 (M+, 20), 183 (100), 165 (1), 115 (5), 107 (8), 91 (4), 77 (22)
224 (M+, 100), 209 (22), 194 (4), 181 (7), 169 (3), 153 (10), 147 (5), 131 (92), 116 (72), 115 (58), 107 (14),
91 (48), 77 (84), 65 (13), 51 (52)
Х2
Х3
Х4
210 (M+, 100), 195 (3), 184 (2), 181 (4), 165 (10), 152 (6), 141 (4), 133 (8), 117 (100), 115 (80), 103 (16),
91 (24), 77 (68), 65 (16), 51 (48)
224 (M+, 100), 209 (7), 194 (4), 183 (5), 181 (6), 165 (5), 153 (4), 147 (6), 131 (50), 116 (68), 115 (64),
107 (5), 91 (50), 77 (72), 65 (20), 51 (44)
224 (M+, 26), 209 (100), 194 (2), 181 (40), 169 (20), 152 (6), 139 (14), 126 (1), 115 (5), 104 (2), 98 (3),
90 (18), 76 (6), 63 (5), 51 (2)
Table 2. Change in concentrations of components of reaction mass of 4-TBDPO thermolysis at 728 K
Molar concentration of components, mol %
Time,
min
phenol
4-TBP
4-IBP
DPO 4-MeDPO 4-EDPO 4-IPDPO 4-NPDPO 4-TBDPO 4-IBDPO
0.0
2.0
0.00
0.04
0.09
0.19
0.10
0.30
0.53
0.75
1.11
0.00
0.03
0.06
0.13
0.10
0.19
0.25
0.31
0.37
0.41
0.45
0.54
0.56
0.66
0.00
0.00
0.01
0.02
0.01
0.02
0.03
0.03
0.05
0.07
0.07
0.11
0.11
0.12
0.00
0.05
0.10
0.18
0.16
0.24
0.28
0.35
0.42
0.45
0.51
0.58
0.63
0.76
0.00
0.04
0.10
0.30
0.27
0.43
0.77
1.13
0.00
0.00
0.00
0.03
0.02
0.07
0.09
0.16
0.36
0.46
0.53
0.76
1.04
1.51
0.00
0.03
0.09
0.28
0.25
0.49
0.63
0.93
1.08
1.26
1.31
1.41
1.68
1.74
0.00
0.00
0.01
0.05
0.04
0.10
0.24
0.50
0.75
0.97
1.09
1.44
1.73
2.27
100.00
99.16
97.93
95.44
95.60
92.34
91.12
0.00
0.65
1.61
5.0
7.0
3.38
3.45
5.82
6.06
7.97
8.64
8.92
9.14
10.0
15.0
20.0
25.0
30.0
32.5
35.0
40.0
45.0
50.0
87.87
85.48
84.28
83.35
81.00
78.84
75.52
1.74
1.88
2.16
2.94
3.47
4.25
1.30
1.39
1.60
1.89
2.52
9.62
10.05
10.65
RUSSIAN JOURNAL OF PHYSICAL CHEMISTRY A Vol. 93 No. 11 2019

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SHAKUN et al.
4-IBDPO is 3.45 mol % when the degree of conver-
CH3
C
CH3
CH2
CH3
CH2
sion of 4-TBDPO is 4.40 mol %, i.e., the selectivity of
the formation of 4-IBDPO was 78%. In general, under
the experimental conditions, with the conversion of
4-TBDPO equal to 0–10%, the selectivity for the for-
mation of 4-TBDPO is 70–80%. The destruction of
4-TBDPO is manifested to a much lesser extent and
contributes to the formation of 4-TBP, phenol, and
DPO as a result of the cleavage of the СAr–Cquater and
CAr–O bonds. In this case, the decomposition practi-
cally has no effect on the alkyl substituent, since the
concentration of 4-MeDPO and 4-IPDPO, for exam-
ple, has an adequate relationship only with 4-IBDPO.
H3C
H3C
H3C
O
O
O
Fig. 2. Possible mechanism of isomerization of 4-TBDPO.
did not exceed 0.5 mol % in the most severe experi-
mental conditions. When constructing the kinetic
decay model, IPB, TBB, and components X1–X4 were
not included in the processing.
The characteristics of the mass spectra of the com- of 4-n-butyl DPO and 4-sec-butyl DPO were found.
ponents are given in Table 1.
This direction of decay looks rather unexpected. Of
particular interest is the fact that in the thermolysis
products of 4-TBDPO, regardless of temperature or
contact time (within the study conditions), no traces
Obviously, this results from the mechanism of conver-
sion of the tert-butyl substituent. Presumably, isomer-
ization, which promotes the conversion of the tert-
butyl substituent exclusively to iso-butyl, can occur
through the formation of a three-membered ring
between Cprim of the tert-butyl substituent and CAr of
the aromatic nucleus (Fig. 2).
RESULTS AND DISCUSSION
Possible Mechanism of Radical Isomerization
of 4-TBDPO
Table 2 shows the change in the concentrations of
the components of the reaction mixture at T = 728 K
as a function of time.
The above mechanism adequately explains why
secondary and normal butylarenes are absent in the
products of the 4-TBDPO thermolysis.
Our analysis of the experimental data presented
showed that during the thermolysis of 4-TBDPO, the
isomerization of the tert-butyl substituent occurs most
readily to form 4-IBDPO. For example, at 728 K and
A similar result was obtained in the course of the
thermolysis of 4-TBP [13]. The data obtained for
a contact time of 10 min, the concentration of 4-TBDPO and 4-TBP suggest the general nature of
O
HO
k7
k6
O
k3
O
HO
HO
k10
k1
k11
k4
O
O
k5
k9
k8
k2
O
O
Fig. 3. Scheme of transformations during thermolysis of 4-TBDPO.
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THERMAL STABILITY OF 4-tert-BUTYL DIPHENYL OXIDE
2127
Table 3. Values of rate constants (ki × 105, s–1) for transformations accompanying thermolysis of 4-TBDPO in the range
703–763 K
k1
k2
k3
k4
k5
k6
k7
k8
k9
k10
k11
T, K
703
708
713
718
723
728
733
738
743
748
753
758
763
2.16
3.26
0.07
0.11
0.15
0.21
0.21
0.28
0.56
0.77
0.89
1.44
1.81
2.64
3.25
0.04
0.06
0.09
0.11
0.12
0.16
0.30
0.42
0.47
0.78
0.95
1.43
1.97
0.06
0.10
0.13
0.18
0.20
0.28
0.46
0.63
0.67
1.15
1.35
2.06
2.80
8.54
10.44
13.90
19.56
20.90
25.20
48.55
65.20
75.85
116.20
167.55
6.12
8.02
2.32
3.51
27.37
37.59
4.85
7.36
8.01
10.44
11.68
18.65
20.19
30.73
43.24
56.79
76.26
3.82
5.29
3.92
11.08
14.68
16.02
19.76
35.27
46.86
52.11
81.80
101.32
5.02
43.98
8.57
6.82
5.21
6.59
62.38
13.67
17.68
24.88
33.48
44.76
55.18
8.99
5.52
7.82
72.56
9.92
8.19
9.66
104.18
129.98
164.91
179.88
278.71
291.40
437.01
537.93
13.18
19.42
24.92
27.18
40.65
42.18
70.70
93.18
13.63
17.02
19.83
29.84
32.25
49.47
62.39
16.39
22.02
25.35
39.30
48.39
69.07
93.66
84.85 103.73
89.68 108.56
146.91 173.64
175.68 208.72
203.96 140.71
277.93 205.26
the radical isomerization of the tert-butyl substituent
associated with various substituted arenes.
(iii) By processing the dependencies obtained in (i)
and (ii) combined with the optimization criterion (2)
2
Development of Kinetic Model of 4-TBDPO Thermolysis
(2)
− r
)
(r
n
i,exp
i,calc
When developing a kinetic model of thermolysis of
4-TBDPO from a number of theoretically possible
transformations in the system under study, a number
of transformations of the greatest significance were
identified (Fig. 3).
Obviously, during thermolysis, the reactions shown
in the scheme (Fig. 3) proceed in several stages. It is
also known that in the course of radical chain pro-
cesses, the presence of free radicals provide no hin-
drances to implement monomolecular reactions [17].
Therefore, we assumed that all reactions selected for
kinetic analysis are monomolecular. Accordingly, the
rate constants indicated in the reaction scheme are a
combination of rate constants of all stages of the reac-
tion. The values of the rate constants of individual
transformations were calculated in accordance with
the following algorithm.
(where n is the number of measurements), we
excluded insignificant reactions and calculated the
rate constants kj (Table 3). The error in determining
the values of the rate constants was <10%.
(iv) Using the rate constants given in Table 3, the
calculated values of the concentrations of 4-TBDPO
thermolysis products were obtained by the Runge–
Kutta method.
(v) Over the entire range of temperatures studied,
the adequacy of the proposed model was tested by
mathematical statistics methods using the Pearson cri-
terion, the value of which exceeded 0.99, and the
Fisher criterion, the calculated value of which at a sig-
nificance level of 0.05 was many times higher than the
tabulated value.
(i) For all reaction products, the actual rates of
concentration change (ri, exp) were calculated, that is
we calculated the differential from Сi, exp = f(τ).
(ii) Rates (ri, exp) of the accumulation of products
were calculated taking into account 38 most likely
reactions according to Eq. (1):
Figure 3 shows that the rate constant k1 for the
isomerization 4-TBDPO → 4-IBDPO is an order of
magnitude higher than the rate constants of destruc-
tive processes (k2–k4) affecting the tert-butyl substitu-
ent and the CAr–O and CAr–Cquater bonds. In particu-
lar, at 728 K, the total value of the rate constants k2–k4
is 7.20 × 10–6 s–1, which is 11.4 times less than k1 =
8.19 × 10–5 s–1.
(1)
r
k C .
j j
= (
)
i,calc
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SHAKUN et al.
C, mol %
100
(a)
4-TBDPO
10
8
80
60
40
20
4-IBDPO
6
4-MeDPO
4
4-NPDPO
4-IPDPO
2
0
4-EDPO
0
10
20
30
40
50
60
τ, min
C, mol %
(b)
2.4
2.0
1.6
1.2
0.8
0.4
Phenol
DPO
4-TBP
4-IBP
0
10
30
50
τ, min
Fig. 4. Comparison of experimental (markers) and calculated (lines) concentrations of the products of thermal transformations
of 4-TBDPO at 728 K: (a) ( ) 4-TBDPO, ( ) 4-IBDPO, ( ) 4-IPDPO, ( ) 4-NPDPO, ( ) 4-EDPO, ( ) 4-MeDPO;
j
m
d
s
h
e
(b) (+) phenol, ( ) DPO, (×) 4-TBP, ( ) 4-IBP.
n
r
In addition, it should be noted that the rate con-
stant for the conversion 4-TBDPO → 4-IPDPO in all
calculations tended to zero. According to our model,
the source of 4-IPDPO and 4-MeDPO is 4-IBDPO,
which undergoes active decomposition of the alkyl
substituent (at 728 K, k5 = 2.52 × 10–4 and k6 = 1.98 ×
Calculation of Parameters
of the Arrhenius Equation
The kinetic analysis of the experimental data in the
range 703–763 K was performed for the reaction 4-
TBDPO → products according to the equations for
calculating the first-order rate constant. By linearizing
the Arrhenius equation in the coordinates “lnki–
10–4 s–1).
1000/T”, it was found that k0 = 1014.3 0.5, Ea = 255.2
6.8 kJ/mol. The values of the decay rate constants of
4-TBDPO are given in Table 4.
The results of the model description of the compo-
sition of the reaction mass of the 4-TBDPO thermol-
ysis at 728 K are presented in Fig. 4.
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THERMAL STABILITY OF 4-tert-BUTYL DIPHENYL OXIDE
2129
Table 4. Values of rate constants for the reaction
CONCLUSIONS
4-TBDPO → products proceeding during thermolysis of
4-TBDPO in the range 703–763 K
In summary, it was found that during the ther-
molysis of 4-tert-butyl diphenyl oxide, the main con-
version is the isomerization to 4-isobutyl diphenyl
oxide. The mechanism of this reaction has been pro-
posed.
ki, s–1
–ln(ki)
T, K
1000/Т
703
708
713
718
723
728
733
738
743
748
753
758
763
1.42
1.41
1.40
1.39
1.38
1.37
1.36
1.36
1.35
1.34
1.33
1.32
1.31
2.33 × 10–5
3.56 × 10–5
4.55 × 10–5
5.53 × 10–5
6.59 × 10–5
9.03 × 10–5
1.55 × 10–4
2.05 × 10–4
2.24 × 10–4
3.48 × 10–4
3.88 × 10–4
5.84 × 10–4
7.38 × 10-4
10.665
10.243
9.998
9.803
9.627
9.312
8.770
8.493
8.402
7.962
7.855
7.445
7.211
In the temperature range 703–763 K, the parame-
ters of the Arrhenius equation have been calculated for
the reaction 4-TBDPO → products, namely, the pre-
0.5
exponential factor k0 = 1014.3
energy Ea = 255.2 6.8 kJ/mol.
and the activation
A kinetic model of the process has been proposed,
according to which 4-IBDPO is the main source of the
decay products in the temperature range of the study,
namely 4-MeDPO, phenol, and 4-IPDPO. In this
case, 4-NPDPO is formed by isomerization of
4-IPDPO, while 4-EDPO is the product of the
destruction of these two components. The destruction
of the initial 4-TBDPO proceeds to a small extent and
is expressed in the breaking of the CAr–O and
CAr‒Cquater bonds to form DPO, 4-TBP, and phenol.
The information obtained can be used in the devel-
opment of promising thermostable and heat-resistant
polymer compositions, since it suggests the behavior
For the reactions included in the kinetic model of of their structure at elevated temperatures. The
the process in the temperature range 703–763 K, the revealed regularities, in general, can serve as the basis
rate constants and parameters of the Arrhenius equa- for further studies of the thermal stability of com-
tion were calculated. The data are given in Table 5.
pounds of the class of alkyl diphenyl oxides.
Table 5. Values of parameters of the Arrhenius equation for transformations accompanying thermolysis of 4-TBDPO in the
range 703–763 K
ki
logk0
Ea, kJ/mol
Reaction
R
4-TBDPO
4-TBDPO
4-TBDPO
4-TBDPO
4-IBDPO
4-IBDPO
4-IBDPO
4-IPDPO
4-IPDPO
4-NPDPO
4-TBP
4-IBDPO
DPO
k1
k2
k3
k4
k5
k6
k7
k8
k9
k10
k11
13.8 0.5
15.1 0.7
15.1 0.6
14.3 0.5
15.7 0.6
14.9 0.6
15.3 0.4
12.6 0.3
15.3 0.4
14.3 0.6
12.5 0.5
248.6 7.0
286.6 9.5
289.4 8.1
276.6 7.3
267.3 9.0
257.7 7.7
268.0 5.7
218.0 4.7
264.0 5.5
247.7 9.1
228.3 6.6
0.99
0.98
0.99
0.99
0.98
0.99
0.99
0.99
0.99
0.99
0.99
Phenol
4-TBP
4-IPDPO
4-MeDPO
Phenol
4-NPDPO
4-EDPO
4-EDPO
4-IBP
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2130
SHAKUN et al.
9. J. Yu and S. Eser, Ind. Eng. Chem. Res. 37, 4591
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Vol. 93
No. 11
2019