Materials and Manufacturing Processes

ISSN: 1042-6914 (Print) 1532-2475 (Online) Journal homepage: http://www.tandfonline.com/loi/lmmp20

An experimental study on operating conditions of

2-ethylhexanol manufacturing process

Ahad Ghaemi & Mohammad Hadi Zerehsaz

To cite this article: Ahad Ghaemi & Mohammad Hadi Zerehsaz (2017): An experimental study
on operating conditions of 2-ethylhexanol manufacturing process, Materials and Manufacturing
Processes, DOI: 10.1080/10426914.2017.1388515

To link to this article: http://dx.doi.org/10.1080/10426914.2017.1388515

Accepted author version posted online: 04

Oct 2017.

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 An experimental study on operating conditions of 2-ethylhexanol

manufacturing process

Ahad Ghaemi

Department of Chemical Engineering, Iran University of Science and Technology, Tehran, Iran
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Mohammad Hadi Zerehsaz

Department of Chemical Engineering, Iran University of Science and Technology, Tehran, Iran

Address correspondence to Ahad Ghaemi, Department of Chemical Engineering, Iran University

of Science and Technology, Tehran 16844, Iran. E-mail: aghaemi@iust.ac.ir

ABSTRACT

In this work, hydrogenation of 2-Ethyl-3-Propylacrolein (EPA) was investigated

experimentally using a laboratory-scale plug flow reactor. In this process, 2-ethylhexanol was

synthesized using a 2-Ethyl-3-Propylacrolein aldehyde in the presence of vinylpyruvate hydratase

(VPH) catalyst. Next, the effects of operating conditions including temperature, pressure, and

species flow rates on its performance were studied within temperature and pressure ranges of 110-

160℃ and 1-6 bars, respectively. The hydrogen and 2-Ethyl-3-Propylacrolein flow rates were

measured to be 150-240ml /hr and 0.03-0.11ml /hr, respectively. The results showed that the

optimum yield of 2-ethylhexanol production is achieved at a temperature of 155℃, the pressure of

4.4 bars, and hydrogen flow rate of 192.4ml /min. Employing optimum operating conditions, the

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 process yield was 99.86%, with hydrogen flow rate identified as the most effective parameter on

the process yield.

KEYWORDS: 2-ethylhexanol, 2-ethyl-3-propylacrolein, hydrogenation, vinylpyruvate

hydratase catalyst

ARTICLE HISTORY

Received 26 August 2016

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Accepted 14 September 2017

Introduction

2-Ethylhexanol is an Oxo alcohol composed of eight carbon atoms with C8H18O chemical

formula. This alcohol is poorly soluble in water but soluble in most organic solvents. The main

applications of this alcohol are in plasticizer production,[1,2] the chemical industries, production of

plastics, solvent extraction, and chemical synthesis.[3,4] About 72% of the total global consumption

of 2-ethylhexanol is in phthalate softeners, which are used in softening the PVC compounds.

Because of the hydrophobicity characteristics of 2-Ethylhexanol, it is also used in hydrophobic

applications.[5] Moreover, it is used in producing low foam surfactants.[6]

There are mainly two kinds of chemical processes in the synthesis of 2-ethylhexanol (i.e.,

Oxo and Guerbet reaction processes) that are performed under different operating conditions.[7–9]

Through the well-known organic chemistry Guerbet reaction, a primary or secondary

alcohol is condensed to form the basic material of a higher alcohol. This product can also be

obtained by combining two lighter alcohols of butanol and 4 alcohols of methanol. Miller and

Bennett (1961) investigated producing 2-ethylhexanol by employing the Guerbet reaction.[10]

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 Through this process, they used 2-ethylhexanol as a solvent and dispersing agent, tripotassium

phosphate to enhance the catalyst activity, and sodium sulfate derivative of 2-ethylhexanol as a

wetting agent.[11]

Poe (1987) presented a procedure for producing 2-ethylhexanol using the Guerbet

reaction,[10] which takes place at a temperature range of 200-300℃. The process, depending on the

alcohol, the catalyst, and the presence of potassium hydroxide, occurs at a temperature range of

240-270℃. Since pressure is an essential controller of the process, primarily as a means of

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maintaining the reactants in the desired physical state, an adequate pressure is employed to

maintain the starting alcohol in the liquid state. It has to be noted that this pressure will vary

depending on the reaction temperature.[10] Due to consuming large amounts of catalyst in the

Guerbet reaction, the undesirable reactions would be also accelerated.[10] Regarding the lower

output of this process and creation of different byproducts, producing 2-ethylhexanol is neither

cost-effective nor applied industrially.[10]

The ease of access to precursors of the Oxo process (i.e., methane, propylene, hydrogen,

and sodium hydroxide) makes this method more feasible in industrial scales compared to other

processes.[8,9] Kessen et al. (1987) investigated the synthesis of 2-ethylhexanol using the Oxo

process, through which propane reacted with carbon monoxide and hydrogen in the presence of a

catalyst containing Rhodium. The process was carried out under temperature and pressure ranges

of 50-140℃ and 0.1 to 30MPa, respectively. Ratio of Rhodium to sulfonated triaryl phosphine and

ratio of organic phase to aqueous phase were adjusted between 1:3 to 1:300, and 1:1 to 1:100,

respectively.[12]

Lueken et al. (1990) presented a two-step procedure for producing 2-ethylhexanol by the

liquid-phase catalytic hydrogenation of 2-Ethylhexyl and a catalyst for performing this catalytic

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 hydrogenation.[13] In the first step, the aldehyde was hydrogenated in the presence of a copper-

containing catalyst using Cu catalyst supplied from Hoechst AG and SiO2 as the carrier at a

temperature range of 140-160℃. The second step was carried out in a temperature range of 120-

140℃ and a pressure range of 2-2.5MPa.[13]

Thurman and Harris reduced the concentration of 2-ethyl-4-methylpentanol in the

producing 2-ethylhexanol[14] by adding the distilled n-butyraldehyde to produce 2-ethylhex-2-enal

and, eventually, hydrogenated 2-ethylhex-2-enal with a catalyst to produce 2-ethylhexanol.[14]

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Table 1 shows the operating conditions of 2-ethylhexanol production. Evidently, in Oxo

method, the process occurs at a lower temperature compared to that of the Guerbet method.

Regarding the high economic value of the Oxo process, further investigations are required

to obtain the optimum operating conditions of 2-ethylhexanol production. The present work was

conducted to evaluate different process conditions of Oxo process (as a commonly applied method

in the industry) using the desired catalysts. Also, the effects of operating conditions including

temperature, pressure, and species flow rates were investigated on the process yield.

Materials and Methods

Kinetics and mechanism of 2-ethylhexanol production

The 2-ethylhexanol production process via the Oxo process is shown in the following

stages:

Refforming  Oxo process  Aldolization  Hydrogenation

In the reforming step, methane is converted to carbon monoxide and hydrogen. Then, in

the Oxo section, the synthesized carbon monoxide and hydrogen react with propylene and generate

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 normal butyl aldehyde. Next, in the aldolization step, the produced normal butyl aldehyde reacts

with sodium hydroxide and produce ethyl propylacroline (EPA). Finally, in the hydrogenation

section, the EPA is converted to 2-ethylhexanol in the presence of a catalyst as follow:[15]

2C3 H6  2CO  4H2  C4 H8O  H2O

Propylene Carbon monoxide Hydrogen (2  EH ) Water (1)

2-ethylhexanol is produced through two reaction steps. In the first step, normal-

butyraldehyde is converted to 2-ethyl-3-propylacroline while in the second step 2-ethyl-3-

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propylacrolein is converted to 2-ethylhexanol as follows:[16]

C8 H14O  2H 2  C8 H18O
( EPA) Hydrogen (2  EH ) (2)

This reaction can take place in either the liquid phase or gas phase in the presence of a

catalyst.[17] Although gas phase reaction is characterized by a high energy consumption, it has the

possibility to regenerate the catalyst. Low energy consumption and small amounts of catalyst are

the advantages of the liquid phase reaction. However, the disadvantage of this process is the

impossibility of catalyst regeneration.[17] Industrial-scale liquid phase hydrogenation is a

predominant technique in the chemical industries.

The hydrogenation catalyst plays an important role in the process. In the present work, the

vinylpyruvate hydrates catalyst was used in the hydrogenation process. Kinetics and mechanism

of the hydrogenation process were presented by several researchers.[17–20] Figure 1 shows the

process stages by details. These stages are presented as follow:

Stage 1: the transport of hydrogen from the gas phase to the interface;

Stage 2: the transport of hydrogen from the interface to the liquid phase;

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 Stage 3: the transport of reactants from the liquid phase to the liquid-solid interface;

Stage 4: adsorption of reactants on the catalyst sites and reaction between species;

Stage 5: the transport of productions to the liquid phase.

The reaction mechanisms are expressed as follows[21]:

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The hydrogenation reactions may occur in both liquid and gas phases. In the liquid phase,

the reactions occur over a catalyst at a temperature of about 160℃ and at a pressure below 30 bars.

In the gas phase, the hydrogenation reactions take place over a catalyst at a temperature of

approximately 170℃ and at a pressure below 6 bars. Regarding the studies conducted in this area,

reaction kinetics based on the species concentration can be presented as below[15,16]:

r  k.CH2 .CA
(3)

where k is the reaction constant and CA and CH2 are the aldehyde concentration and

hydrogen concentration, respectively. The reaction constant is shown as below[22]:

9000
ln k  19.5 
RT (4)

Pilot plant of 2-ethylhexanol production

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 Hydrogenation process is applied in a variety of oil and gas, petrochemical, and chemical

industries and plays an important role in the production of alcohols, hydrogenated oils, and

processes for removal of sulfur from refinery products. However, some problems may occur during

the implementation of the process. For instance, an improper combination of materials in the

reactor leads to a non-uniform distribution of reactants in the hydrogenation reactor and finally

causes the low process yield. In some cases, the poor distribution of temperature in the reactor

leads to non-accurate hydrogenation process. Also, using improper catalysts coupled with the
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improper conditions of catalysts leads to a lower conversion, selectivity, and output of final

products. Impurities and heavy components in the feed may result in precipitation or generation of

heavy components leading to higher pressure drop in the reactor and decrease of catalyst lifetime.

Non-adjustment of process optimum conditions, including temperature, pressure, and

concentration may also lead to a decrease in process yield and selectivity of the process. In

addition, improper catalyst size causes a lower process yield due to the diversion of the optimum

ratio of surface area/volume. The uncertainty involved in the kinetics of many hydrogenation

reactions would highlight the need for the optimum design of industrial reactors for different

materials. The constructed pilot is designed such that to investigate the mentioned problems most

effectively. Moreover, it enables optimizing the catalytic reaction process regarding the process

parameters. This pilot study was conducted for hydrogenation processes and for a vast range of

liquid-gas chemical processes. Figure 2 shows the equipment used in the pilot plant for conducting

the hydrogenation reactions of 2-Ethylhexanal.

The reciprocating piston pump can pump a variety of corrosive and toxic liquids up to 200

bars and 0.01-20 cm3 of flow rate. The storage vessels of hydrogen and nitrogen were about 20

liters and 50 bars, each one connected to a mass flow controller that can show the flow rate and

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 pressure of the gas phase. The static mixer is in the form of a cylinder with 200mm of length and

50mm in diameter, applied for a better combination of nitrogen and hydrogen. Moreover, the

reactor consists of 500mm in length and 25.4mm in diameter, covered by a heater supplying the

reactor temperature from 50 to 300℃.

Materials and catalyst specifications

The raw materials used in this work are hydrogen, nitrogen, and 2-ethyl-3-propylacrolein
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(EPA) or 2-ethyl 2-hexenal with a purity of 99.5%. The hydrogen and nitrogen gases, both with

99.995% purity, were purchased from Sabalan Gas Co. The catalyst used in the hydrogenation

process was vinylpyruvate hydratase, which mainly includes Zinc oxide, Alumina, and Copper

oxide. The chemical and physical specifications of the catalyst are presented in Tables 2 and 3,

respectively.

Experimental

The acquired experimental data were tested via the one factor at a time (OFAT) and Box-

Behnken methods. First, the reactor was loaded with 3 gr of the PVH catalyst in the middle of the

reactor, followed by filling the rest of the upper and lower sections of the reactor with glass

granulates for a better combination. Then, the reactor temperature was set at the definite target

using the ceramic heater elements and temperature controllers. Six sets of RTD were used for a

better temperature recording. The reactor is divided into 3 areas, with one RTD installed at their

outer layer and one RTD installed at their inner layer. After temperature adjustment, liquid EPA

was pumped to the reactor, which could record and show the outlet flow rate. Next, hydrogen and

nitrogen gases were conducted into the reactor via mass flow controller systems. After the reaction

of materials in the reactor, the output was tested using a gas chromatography analyzer. To increase

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 the process accuracy and decrease the error coefficient, liquid EPA was poured in a burette and

the outlet liquid entered into the pump. Next, the internal EPA was pumped into the reactor using

a reciprocating piston embedded in the pump. The placement of this burette leads to an increase in

the accuracy of the pumped flow rate.

Results and Discussions

The OFAT and Box-Behnken methods were applied in the experimental design of the
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hydrogenation process. In the OFAT method, first, the pressure was set at 5 bars and then

hydrogen, nitrogen, and EPA flow rates were adjusted to 198ml /min, 30ml /min, and 0.04ml /min,

respectively. The process was performed within the temperature range of 120-160℃. Table 4

shows the conversion of EPA at different temperatures. As shown in Table 4, the optimum

temperature of EPA hydrogenation to achieve suitable conversion is 155℃.

At the optimum temperature, the process pressure was varied in the range of 1-5.4 bars.

Based on the conversion variation with pressure presented in Table 5, it is seen that the optimum

pressure is 4.4 bars.

At the optimum temperature and pressure, the hydrogen flow rate was varied in the range

of 150-220ml /min. From Table 6, it is seen that the hydrogen flow rate with 192.4ml /min gives

the highest conversion of EPA hydrogenation in the reactor.

Table 7 shows the experimental results of producing 2-ethylhexanol at different

conditions. The results show that the optimum temperature for the reaction is 155℃, which

supplies a proper activation energy as the best conversion percentage. At higher temperatures,

despite the very low improvement of the reaction conversion percentage, there is no economic

feasibility for the reaction. Since this reaction is endothermic, the conversion percentage increases

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 with increasing temperature, suggesting that reactants require higher temperatures to have better

reaction conditions.

Figures 3 and 4 show the effects of hydrogen and EPA flow rates on the conversion

percentage, respectively. It is clear that at lower EPA values, no change in the conversion

percentage is observed. Therefore, low EPAs do not affect the conversion percentage. Figure 3

indicates that by an increase in the hydrogen flow rate, the conversion percentage is raised and

became constant thereafter. At the beginning, the reaction requires a specific amount of hydrogen
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followed by a lower conversion percentage at lower hydrogen flow rates. Moreover, the results

showed that hydrogen flow rate is more effective on the EPA conversion compared with the other

process parameters.

Figure 5 shows the effect of pressure on the EPA conversion. It is seen that by increasing

the pressure, the EPA conversion would also increase. Besides, when the pressure exceeds 4.4

bars, the EPA conversion would not change and reach its peak. In this process, the energy required

for bond breaking and forming is supplied by the positive pressure. Because the reaction occurred

in the reactor was endothermic, at the different concentration of reactants, the process yield

increases with increasing temperature.

Figures 6 and 7 show the effect of species flow rates on 2-ethylhexanol production yield.

It was found that at a constant temperature and pressure, the process yield would decline by

increasing the EPA concentration. This behavior is explained by the fact that at values lower than

this specific level EPAs react with the other reactants. Figure 7 shows the effect of hydrogen flow

rates on 2-ethylhexanol yield; first, the process yield rises by increasing hydrogen flow rate and

then remains constant. At the beginning of the reaction, the process requires some hydrogen

content and if the actual value is lower than the desired value, the process yield would decrease.

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 The effect of hydrogen concentration on the selectivity varies by output rhythm. Selectivity

would be also increased by increasing the hydrogen flow rate, which implies that the low reaction

of hydrogen content would lead to more side reactions, leading to more byproducts. In addition, a

higher EPA content leads to the lower selectivity of reaction due to producing more byproducts.

The higher temperature results in the reaction improvement in the desired direction, producing

lower contents of byproducts, which finally affects the selectivity. Figure 8 shows the effect of

hydrogen flow rate on the selectivity.

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The yield of producing 2-ethylhexanol obtained in this work and from previous works is

presented in Table 8. Overall, two processes (Oxo and the Guerbet reaction methods) were applied

for producing 2-ethylhexanol. The results indicate that the yield of the present work is higher

(99.83%) at the optimum operating conditions compared to that of the previous works.

Conclusion

In this research, the operating conditions of EPA hydrogenation were investigated

experimentally using a laboratory-scale pilot plant. The hydrogenation process was performed

using the Oxo process and found that it is a suitable method for producing 2-ethylhexanol in terms

of economic justifications and operating conditions. The result also showed that hydrogenation in

the liquid phase is an endothermic reaction. Since the economic concept and advantages of the

liquid phase hydrogenation, it is predominantly considered in the chemical industries. The

optimum conversion of the hydrogenation process was obtained at a temperature of 155℃, the

pressure of 4.4 bars, and hydrogen flow rate of 192.4ml /min. Eventually, the results show that

hydrogen flow rate is the most effective parameter on producing 2-ethylhexanol.

References

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 Table 1. Experimental conditions of different processes for 2-Ethylhexanol production.

Author Year Process T (C) P (Mpa) Ref.

Miller and Bennett 1961 Guerbet reaction 218–228 4.1–4.5 [11]

Ronald 1967 Guerbet reaction 200–300 0.1 [10]

Kessen et al. 1987 Oxo process 50–140 0.1–30 [12]

Lueken et al. 1990 Oxo process 120–180 2–2.5 [13]

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Thurman and Harris 1993 Oxo process 70–90 – [14]

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 Table 2. Composition of vinylpyruvate hydratase (VPH) catalyst.

Component Value (%)

CuO 39.0

ZnO 45.0

Ce2O3 2.0

Al2O3 8.0

Na2O 0.3
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Graphite 2.5

H2O2 & CO2 3.2

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 Table 3. Physical specifications of VPH catalyst.

Nominal diameter 6 mm

Nominal length 5 mm

BET surface area > 80 m2/g

Tapped bulk 800 Kg/m3

Density (approx.) 50 ib/ft3

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Mean horizontal Crash strength > 20 kgf

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 Table 4. Experimental conversion results at different temperatures.

Temperature (°C) Conversion (%)

130 87.00

140 98.80

145 98.75

150 99.67

155 99.85
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160 99.86

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 Table 5. Variation of EPA conversion at different pressures.

Pressure (psi) Conversion (%) Yield (%)

78 99.85 99.85

65 99.88 99.88

51 99.65 99.75

36 66.86 89.78

16 47.10 66.46
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 Table 6. The hydrogenation process yield and conversion at different hydrogen flow rates.

H2 flow (ml/min) Conversion (%) Yield (%)

150.0 96.05 85.27

170.0 97.61 90.01

192.4 99.86 99.86

220.0 99.81 99.81

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 Table 7. Experiments of 2-Ethylhexanol producing at different operational conditions.

EPA flow rate H2 flow rate Temperature (°C) Conversion (%)

(ml/hr) (ml/hr)

0.07 240 130 89.71

0.10 240 145 90.29

0.10 195 160 98.96

0.04 195 160 99.21

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0.04 150 145 99.46

0.07 240 160 99.70

0.07 195 145 98.64

0.04 240 145 99.23

0.07 195 145 96.06

0.07 195 145 97.87

0.04 195 130 99.10

0.10 195 130 84.02

0.07 150 130 92.76

0.07 150 160 99.83

0.10 150 145 94.08

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 Table 8. Comparison the yield of 2-Ethylhexanol production with the previous works.

Author Process T (C) P (Mpa) Yield %

Miller and Bennett[11] Guerbet reaction 218–228 4.1–4.5 83.00

Poe[10] Guerbet reaction 200–300 0.1 89.90

Kessen et al.[12] Oxo process 50–140 0.1–30 97.70

Lueken et al.[13] Oxo process 120–180 2–2.5 99.90

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Thurman and Harris[14] Oxo process 70–90 – 99.80

This work Oxo process 110–160 0.1–0.6 99.86

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 Downloaded by [Southern Cross University] at 21:07 04 October 2017

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Figure 1. The schematic of process stages of EPA hydrogenation.
 Figure 2. Schematic of the pilot plant for production of 2-ethylhexanol.
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Figure 3. Effects of hydrogen flow rate on the EPA conversion.
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Figure 4. Effects of EPA flow rate on the EPA conversion.
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Figure 5. Effect of pressure on the EPA conversion.
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Figure 6. Effect of EPA flow rate on the 2-ethylhexanol yield.
 Figure 7. Effect of hydrogen flow rate on the 2-ethylhexanol yield.
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Figure 8. Effect of hydrogen flow rate on the 2-EH selectivity.