**3. Results and discussion**

**Table 4** shows the results of the ethanol absolutization using tetraethoxytitanium. As can be seen from the table, absolutized ethanol can be obtained with the ethanol concentration, which increases from 92.5 to 93–96 wt% (or 95.41–99.50 vol%), but does not reach 100 wt%.

Therefore, at the second stage of our research, we used a more reactive dehydrator—calcium oxide which was calcined at 1123 K; its characteristics are presented in **Table 2**. We selected a sample no. 1 with a minimum content of magnesium oxide (MgO—5%), carbonates (CaCO3 + MgCO33%) and other impurities (SiO2 + Al2O3–1%). As can be seen from the results presented in **Table 4**, the CaO consumption decreases to 17 wt%, compared with 25 wt% of (C2H5O)4Ti, and the concentration of absolutized ethanol increases to 99.5–100.0 wt %, or 99.7– 100.0 vol%. In addition, the loss of alcohol decreases. After absolutization with (C2H5O)4Ti these losses reaches 15–25% C2H5OH (**Table 3**), while for CaO they decrease to 8–13% relative to the initial C2H5OH (**Table 4**). So we can say that calcium oxide as a chemically binding water reagent is much more effective dehydrator. As can be seen from **Figure 1**, the ethanol concentration after treatment with

calcined calcium oxide (17.5% CaO) reaches 99.95 wt%, while the absolutization with tetraethoxytitanium increases the concentration of ethanol only to 96.5 wt%. At the same time, the non-absolutized 95% ethanol contains an admixture of MTBE (0.09531 wt %). In this case, the low-boiling impurity in the non-absolute

*Dependence of the ethyl alcohol concentration after absolutization with tetraethoxytitanium (25%*

According to the chromatogram (**Figure 2**), the concentration of nonabsolutized ethanol reaches 97.8499 vol % against 95.0%, as it was measured by the weight pycnometer method (**Tables 4** and **5**). At the same time, the concentration of ethanol absolutized with calcium oxide (**Figure 3**) is 97.5724 vol %. Taking into account 2.3432% of unidentified low-boiling impurity (*Tb* = 308–310 K) and 0.03433% of MTBE (according to the chromatogram in **Figure 3**), the total concentration of absolutized ethanol is 99.95 vol %, as it was determined by the

Taking into account the chromatogram data in **Figure 3** and its interpretation, we determine the qualitative composition of one of the unknown components (X = 2.3432%), which appears in the chromatogram of ethyl alcohol (99.95%), absolutized with CaO for 2.8 min. At the same time, the chromatographic analysis of 99.99% ethyl alcohol absolutized by industrial method [43] (**Figure 4**), shows 100.03 vol % of ethanol. The difference of 0.03% might be a mistake of the device

Unfortunately, this impurity is not identified by graded chromatograms of alcohols and ethers, therefore, an IR spectral analysis of this alcohol is performed, which

*Chromatogram of the initial, non-absolutized ethanol (95.0 vol%) with corresponding interpretation.*

ethanol is absent (**Figure 2**).

*(C2H5O)4Ti) and calcium oxide (20% CaO).*

*Improving the Technology of Synthesis Absolutized Bioethanol*

*DOI: http://dx.doi.org/10.5772/intechopen.92332*

**Figure 1.**

**Figure 2.**

**227**

pycnometric method (**Tables 4** and **5**).

or an alcohol supplier analysis method.


#### **Table 4.**

*Properties of ethanol after absolutization with tetraethoxytitanium.*


#### **Table 5.**

*Properties of ethanol after absolutization by CaO (90%).*

#### **Figure 1.**

**3. Results and discussion**

**Initial ethanol amount, SSU 4221:200 95 vol%, 92.5 wt %**

**Table 4.**

**Table 5.**

**226**

**The initial ethanol amount, 95 vol%, 92.5% mas.**

**The amount of ethanol obtained after absolutization**

*Properties of ethanol after absolutization with tetraethoxytitanium.*

**The amount of ethanol obtained after absolutization**

*Properties of ethanol after absolutization by CaO (90%).*

(or 95.41–99.50 vol%), but does not reach 100 wt%.

*Analytical Chemistry - Advancement, Perspectives and Applications*

**Table 4** shows the results of the ethanol absolutization using tetraethoxytitanium. As can be seen from the table, absolutized ethanol can be obtained with the ethanol concentration, which increases from 92.5 to 93–96 wt%

Therefore, at the second stage of our research, we used a more reactive dehydrator—calcium oxide which was calcined at 1123 K; its characteristics are presented in **Table 2**. We selected a sample no. 1 with a minimum content of magnesium oxide (MgO—5%), carbonates (CaCO3 + MgCO33%) and other impurities (SiO2 + Al2O3–1%). As can be seen from the results presented in **Table 4**, the CaO consumption decreases to 17 wt%, compared with 25 wt% of (C2H5O)4Ti, and the concentration of absolutized ethanol increases to 99.5–100.0 wt %, or 99.7– 100.0 vol%. In addition, the loss of alcohol decreases. After absolutization with (C2H5O)4Ti these losses reaches 15–25% C2H5OH (**Table 3**), while for CaO they decrease to 8–13% relative to the initial C2H5OH (**Table 4**). So we can say that calcium oxide as a chemically binding water reagent is much more effective dehydrator. As can be seen from **Figure 1**, the ethanol concentration after treatment with

> **Ethanol yield after absolutization**

**Ethanol yield after absolutization**

**The amount of Ti (OC2H5)4**

> **The amount of СаО**

*V***, ml** *m***, g** *V***, ml** *m***, g wt%** *m***, g % g/cm<sup>3</sup> vol% wt%** 100 82.15 96 75.77 92.23 18 17.9 0.7893 100.0 100.0 100 82.16 93 73.42 89.36 17.8 17.8 0.7894 99.97 99.95 100 82.10 93 73.42 89.43 17.5 17.5 0.7895 99.93 99.89 100 82.10 90 71.69 87.32 17 17.1 0.7899 99.72 99.51

*V***, ml** *m***, g** *V***, ml** *m***, g wt%** *m***, g % g/cm<sup>3</sup> vol% wt%** 100 82.15 85 69.07 84.08 26.65 25 0.8126 95.41 93.0 100 82.16 85.1 70.72 86.08 27.55 25.11 0.8065 95.85 93.5 100 82.10 77.59 62.1 75.14 29.15 26.20 0.8014 97.49 96.0 100 82.10 77.59 62.1 75.14 29.15 26.20 0.8014 99.50 96.0

**Ethanol density after absolutization**

**Ethanol density after absolutization**

**Ethanol concentration after absolutization**

**Ethanol concentration after absolutization**

*Dependence of the ethyl alcohol concentration after absolutization with tetraethoxytitanium (25% (C2H5O)4Ti) and calcium oxide (20% CaO).*

calcined calcium oxide (17.5% CaO) reaches 99.95 wt%, while the absolutization with tetraethoxytitanium increases the concentration of ethanol only to 96.5 wt%.

At the same time, the non-absolutized 95% ethanol contains an admixture of MTBE (0.09531 wt %). In this case, the low-boiling impurity in the non-absolute ethanol is absent (**Figure 2**).

According to the chromatogram (**Figure 2**), the concentration of nonabsolutized ethanol reaches 97.8499 vol % against 95.0%, as it was measured by the weight pycnometer method (**Tables 4** and **5**). At the same time, the concentration of ethanol absolutized with calcium oxide (**Figure 3**) is 97.5724 vol %. Taking into account 2.3432% of unidentified low-boiling impurity (*Tb* = 308–310 K) and 0.03433% of MTBE (according to the chromatogram in **Figure 3**), the total concentration of absolutized ethanol is 99.95 vol %, as it was determined by the pycnometric method (**Tables 4** and **5**).

Taking into account the chromatogram data in **Figure 3** and its interpretation, we determine the qualitative composition of one of the unknown components (X = 2.3432%), which appears in the chromatogram of ethyl alcohol (99.95%), absolutized with CaO for 2.8 min. At the same time, the chromatographic analysis of 99.99% ethyl alcohol absolutized by industrial method [43] (**Figure 4**), shows 100.03 vol % of ethanol. The difference of 0.03% might be a mistake of the device or an alcohol supplier analysis method.

Unfortunately, this impurity is not identified by graded chromatograms of alcohols and ethers, therefore, an IR spectral analysis of this alcohol is performed, which

#### **Figure 2.**

*Chromatogram of the initial, non-absolutized ethanol (95.0 vol%) with corresponding interpretation.*

#### **Figure 3.**

*Chromatogram of the ethanol (99.95 vol%), absolutized with calcium oxide with corresponding interpretation.*

#### **Figure 4.**

*Chromatogram of the ethanol (99.99 vol%), absolutized by industrial method [43] with corresponding interpretation.*

is compared with the IR spectra of the original (95%) and pure absolute (100%) ethyl alcohol (**Figure 5**). As can be seen from **Figure 5**, the IR spectra of all three samples do not differ significantly from each other. Only in two absorption regions 3320–3330 and 1630–1640 cm<sup>1</sup> , there is a noticeable difference in the absorption intensity of the fluctuations of the corresponding groups, which significantly decrease from the maximum in the original non-absolutized 95% C2H5OH (curve 1, **Figure 5**) to a minimum in absolute 100% C2H5OH (curve 3, **Figure 5**).

First of all, the amount of water in samples of ethanol decreases from 4–5% in the initial non-absolutized alcohol (*curve* 1, **Figure 5**) to 0.1–0.05% in the absolutized with CaO ethanol (*curve* 2, **Figure 5**) and up to 0% in the absolutized 100% C2H5OH (*curve* 3, **Figure 5**). Therefore, the absorption intensity in the region of 3320–3330 cm<sup>1</sup> , which corresponds to the valence fluctuations of the hydroxyl groups of the H2O molecules, decreases by 20% (according to the spectrograms in **Figure 5**). This is noticed in the transition from the non-absolutized 95% C2H5OH (*curve* 1, **Figure 5**) to the absolutized with CaO ethanol (*curve* 2, **Figure 5**) and to the absolute 100% ethanol (*curve* 3, **Figure 5**). In addition, in the spectrograms of the absolutized with CaO 99.95% C2H5OH (*curve* 1, **Figure 5**) and absolute 100% ethanol (*curve* 3, **Figure 5**) absorption disappears in the region of deformation oscillations 1630–1640 cm<sup>1</sup> of double bonds C]C or C]O [10] compared with non-absolutized 95% alcohol (*curve* 1, **Figure 5**), which can be identified as the presence of ketones, aldehydes, complex esters and ethers, and corresponds to the

presence of MTBE in ethyl alcohol, which is identified in chromatograms of nonabsolutized 95% and absolutized with CaO 99.95% ethyl alcohol (**Figures 2** and **3**)

*Mass spectra of initial 95% ethanol (a) and absolutized with CaO 99.95% ethanol (b).*

*Infrared spectra of different ethyl alcohols: 95.0 vol% non-absolutized C2H5OH (1); 99.95 vol% C2H5OH*

*absolutized with CaO (2) and 100% C2H5OH of industrial product (3).*

*Improving the Technology of Synthesis Absolutized Bioethanol*

*DOI: http://dx.doi.org/10.5772/intechopen.92332*

For identification and more proper determination of the composition and structure of the impurity (*X* = 2.3432%) in ethanol, which is identified in the chromatogram of the absolutized with CaO ethanol at 2.845 min (**Figure 5**), we carried out a mass spectrometric analysis of our samples of non-absolutized 95% and absolutized with CaO 99.95% ethanol by the mass spectroscope MX-7304A, AO.SELMI shown

in the range of 0.034–0.095%.

in **Figure 6**.

**229**

**Figure 6.**

**Figure 5.**

*Improving the Technology of Synthesis Absolutized Bioethanol DOI: http://dx.doi.org/10.5772/intechopen.92332*

is compared with the IR spectra of the original (95%) and pure absolute (100%) ethyl alcohol (**Figure 5**). As can be seen from **Figure 5**, the IR spectra of all three samples do not differ significantly from each other. Only in two absorption regions

*Chromatogram of the ethanol (99.99 vol%), absolutized by industrial method [43] with corresponding*

*Chromatogram of the ethanol (99.95 vol%), absolutized with calcium oxide with corresponding interpretation.*

*Analytical Chemistry - Advancement, Perspectives and Applications*

intensity of the fluctuations of the corresponding groups, which significantly decrease from the maximum in the original non-absolutized 95% C2H5OH (curve 1,

First of all, the amount of water in samples of ethanol decreases from 4–5% in the initial non-absolutized alcohol (*curve* 1, **Figure 5**) to 0.1–0.05% in the absolutized with CaO ethanol (*curve* 2, **Figure 5**) and up to 0% in the absolutized 100% C2H5OH (*curve* 3, **Figure 5**). Therefore, the absorption intensity in the region of

groups of the H2O molecules, decreases by 20% (according to the spectrograms in **Figure 5**). This is noticed in the transition from the non-absolutized 95% C2H5OH (*curve* 1, **Figure 5**) to the absolutized with CaO ethanol (*curve* 2, **Figure 5**) and to the absolute 100% ethanol (*curve* 3, **Figure 5**). In addition, in the spectrograms of the absolutized with CaO 99.95% C2H5OH (*curve* 1, **Figure 5**) and absolute 100% ethanol (*curve* 3, **Figure 5**) absorption disappears in the region of deformation oscillations 1630–1640 cm<sup>1</sup> of double bonds C]C or C]O [10] compared with non-absolutized 95% alcohol (*curve* 1, **Figure 5**), which can be identified as the presence of ketones, aldehydes, complex esters and ethers, and corresponds to the

, which corresponds to the valence fluctuations of the hydroxyl

**Figure 5**) to a minimum in absolute 100% C2H5OH (curve 3, **Figure 5**).

, there is a noticeable difference in the absorption

3320–3330 and 1630–1640 cm<sup>1</sup>

3320–3330 cm<sup>1</sup>

**228**

**Figure 3.**

**Figure 4.**

*interpretation.*

*Infrared spectra of different ethyl alcohols: 95.0 vol% non-absolutized C2H5OH (1); 99.95 vol% C2H5OH absolutized with CaO (2) and 100% C2H5OH of industrial product (3).*

**Figure 6.** *Mass spectra of initial 95% ethanol (a) and absolutized with CaO 99.95% ethanol (b).*

presence of MTBE in ethyl alcohol, which is identified in chromatograms of nonabsolutized 95% and absolutized with CaO 99.95% ethyl alcohol (**Figures 2** and **3**) in the range of 0.034–0.095%.

For identification and more proper determination of the composition and structure of the impurity (*X* = 2.3432%) in ethanol, which is identified in the chromatogram of the absolutized with CaO ethanol at 2.845 min (**Figure 5**), we carried out a mass spectrometric analysis of our samples of non-absolutized 95% and absolutized with CaO 99.95% ethanol by the mass spectroscope MX-7304A, AO.SELMI shown in **Figure 6**.

As can be seen in the mass spectrogram of non-absolutized 95% ethyl alcohol (**Figure 6a**), radical composition of the impurity is formed by the electron action of the mass spectrometer, there can be three types of free radicals with molecular weights such as 32.01 m.u.—C2H5• = 29 m.u.; 76.99 m.u.—(CH3)3O• = 73 m.u.; 105.1 m.u.—C(CH3)3OOCH2• = 103 m.u. They may be formed by the action of electrons of the mass spectrometer on ethyl alcohol C2H5OH and methyl *tret*-butyl ether C(CH3)3OOCH2, which are identified in the chromatograms of the initial nonabsolutized 95% alcohol (**Figure 2**). At the same time, for absolutized with calcium oxide 99.95% ethanol (**Figure 6b**) in the composition of the impurity radicals formed by the action of electrons of the mass spectrometer, there can be only two types of free radicals with molecular weights such as 45.15 m.u.—C2H5O• = 44 m.u. and 73.16 m.u.—(C2H5)2O• = 74 m.u. They can be formed by the electron influence of the mass spectrometer on ethyl alcohol C2H5OH and diethyl ether (C2H5)2O, which are identified in a chromatogram of the 99.95% ethanol absolutized with CaO (**Figure 3**) [44, 45].

Taking into account that we know the retention time of the impurity (*X* = 2.3432% at 2.845 min), which is not identified in the chromatogram of 99.95% ethanol, absolutized with CaO (**Figure 3**), therefore, we have constructed dependence the retention time of three kinds of alcohol: *i*-propanol, ethanol, methanol and diethyl ether (DEE) depending on the boiling points of this substances in the chromatogram, shown in **Figure 7**.

temperature (below 263 K). Thus, the diethyl ether presence improves the gasoline combustion efficiency, which we have checked by adding 10–95% absolutized (97.5%) alcohol containing 2.34% of diethyl ether, which is presented

*octane number) of oxygen-generating additives (DME—dimethyl ether, DEE—diethyl ether, methanol,*

numbers of gasoline, in which ethanol with diethyl ether is added.

number of initial gasoline; Ce—ethanol content [48].

*Physico-chemical characteristics (1, boiling temperature <sup>o</sup>*

*ethanol) in comparison with the characteristics of gasoline A-95.*

*Improving the Technology of Synthesis Absolutized Bioethanol*

*DOI: http://dx.doi.org/10.5772/intechopen.92332*

Octane numbers of A-80 gasoline with absolute ethanol additives (gasolineethanol mixture) are counted according to the authorship formula which is derived from experimental data [47]. These octane numbers are compared with the octane

where ONGE—octane number of gasoline-ethanol mixture; ON0—octane

and compared with the octane number of gasoline-ethanol mixtures to which

*Dependence of the octane number of gasoline A-80 on the amount and kind of added ethanol: theoretically calculated ON (1) of gasoline-ethanol mixtures from the formula [46] and experimentally obtained ON (2) of gasoline-ethanol mixtures with the addition of absolutized ethyl alcohol containing 2.34% of diethyl ether.*

Obtained data of the octane number dependence is performed in **Figure 9** (*curve* 1)

ONGE ¼ ½ � 26*:*44—0*:*29 ON0 ð Þ lnCe þ ½ � 1*:*32 ON0 ð Þ—29*:*49 (5)

*C; 2, density g/sm3* � *10; 3, molecular weight; 4,*

in **Figure 9** [46].

**Figure 8.**

**Figure 9.**

**231**

The analysis of the curves shows that the diethyl ether retention time at the boiling point of 307.6 K (34.6°C) is 2.85 min, which coincides with the chromatogram data (2.845 min). In this way, we confirm the assumption that during the absolutization of 95% ethanol with calcium oxide, ethyl alcohol containing 2.3432% of diethyl ether and 97.5724% C2H5OH can be obtained.

We checked how 2.3432% of diethyl ether influences the ethanol octane number and the gasoline octane number. Previously, the physico-chemical characteristics of some oxygen-generating additives for gasoline, shown in **Figure 8**, were analyzed. As can be seen from **Figure 8**, the density and molecular mass of diethyl ether are close to those of gasoline A-95. The boiling point of the diethyl ether 307.6 K is lower than that of gasoline. It is approaching the boiling point of the first fraction of gasoline, which is 307.6 K. These properties are especially useful for accelerated engines of gasoline cars in winter, when ignition is hampered by a lowered ambient

#### **Figure 7.**

*Dependence of retention time (min) of* i*-propanol (355.4°K), ethanol (351.37°K), methanol (337.6°K), and diethyl ether (DEE) (307.6°K), and the boiling points of these substances from the chromatogram (Figure 3).*

*Improving the Technology of Synthesis Absolutized Bioethanol DOI: http://dx.doi.org/10.5772/intechopen.92332*

#### **Figure 8.**

As can be seen in the mass spectrogram of non-absolutized 95% ethyl alcohol (**Figure 6a**), radical composition of the impurity is formed by the electron action of the mass spectrometer, there can be three types of free radicals with molecular weights such as 32.01 m.u.—C2H5• = 29 m.u.; 76.99 m.u.—(CH3)3O• = 73 m.u.; 105.1 m.u.—C(CH3)3OOCH2• = 103 m.u. They may be formed by the action of electrons of the mass spectrometer on ethyl alcohol C2H5OH and methyl *tret*-butyl ether C(CH3)3OOCH2, which are identified in the chromatograms of the initial nonabsolutized 95% alcohol (**Figure 2**). At the same time, for absolutized with calcium oxide 99.95% ethanol (**Figure 6b**) in the composition of the impurity radicals formed by the action of electrons of the mass spectrometer, there can be only two types of free radicals with molecular weights such as 45.15 m.u.—C2H5O• = 44 m.u. and 73.16 m.u.—(C2H5)2O• = 74 m.u. They can be formed by the electron influence of the mass spectrometer on ethyl alcohol C2H5OH and diethyl ether (C2H5)2O, which are identified in a chromatogram of the 99.95% ethanol absolutized with CaO

*Analytical Chemistry - Advancement, Perspectives and Applications*

Taking into account that we know the retention time of the impurity

(*X* = 2.3432% at 2.845 min), which is not identified in the chromatogram of 99.95% ethanol, absolutized with CaO (**Figure 3**), therefore, we have constructed dependence the retention time of three kinds of alcohol: *i*-propanol, ethanol, methanol and diethyl ether (DEE) depending on the boiling points of this substances in the

The analysis of the curves shows that the diethyl ether retention time at the boiling point of 307.6 K (34.6°C) is 2.85 min, which coincides with the chromatogram data (2.845 min). In this way, we confirm the assumption that during the absolutization of 95% ethanol with calcium oxide, ethyl alcohol containing 2.3432%

We checked how 2.3432% of diethyl ether influences the ethanol octane number and the gasoline octane number. Previously, the physico-chemical characteristics of some oxygen-generating additives for gasoline, shown in **Figure 8**, were analyzed. As can be seen from **Figure 8**, the density and molecular mass of diethyl ether are close to those of gasoline A-95. The boiling point of the diethyl ether 307.6 K is lower than that of gasoline. It is approaching the boiling point of the first fraction of gasoline, which is 307.6 K. These properties are especially useful for accelerated engines of gasoline cars in winter, when ignition is hampered by a lowered ambient

*Dependence of retention time (min) of* i*-propanol (355.4°K), ethanol (351.37°K), methanol (337.6°K), and diethyl ether (DEE) (307.6°K), and the boiling points of these substances from the chromatogram (Figure 3).*

(**Figure 3**) [44, 45].

**Figure 7.**

**230**

chromatogram, shown in **Figure 7**.

of diethyl ether and 97.5724% C2H5OH can be obtained.

*Physico-chemical characteristics (1, boiling temperature <sup>o</sup> C; 2, density g/sm3* � *10; 3, molecular weight; 4, octane number) of oxygen-generating additives (DME—dimethyl ether, DEE—diethyl ether, methanol, ethanol) in comparison with the characteristics of gasoline A-95.*

temperature (below 263 K). Thus, the diethyl ether presence improves the gasoline combustion efficiency, which we have checked by adding 10–95% absolutized (97.5%) alcohol containing 2.34% of diethyl ether, which is presented in **Figure 9** [46].

Octane numbers of A-80 gasoline with absolute ethanol additives (gasolineethanol mixture) are counted according to the authorship formula which is derived from experimental data [47]. These octane numbers are compared with the octane numbers of gasoline, in which ethanol with diethyl ether is added.

$$\text{ONGE} = [\text{26.44} \underline{\text{--0.29}}(\text{ON0})] \text{lnCe} + [\text{1.32}(\text{ON0}) - \text{29.49}] \tag{5}$$

where ONGE—octane number of gasoline-ethanol mixture; ON0—octane number of initial gasoline; Ce—ethanol content [48].

Obtained data of the octane number dependence is performed in **Figure 9** (*curve* 1) and compared with the octane number of gasoline-ethanol mixtures to which

#### **Figure 9.**

*Dependence of the octane number of gasoline A-80 on the amount and kind of added ethanol: theoretically calculated ON (1) of gasoline-ethanol mixtures from the formula [46] and experimentally obtained ON (2) of gasoline-ethanol mixtures with the addition of absolutized ethyl alcohol containing 2.34% of diethyl ether.*

ethanol containing 2.34% of diethyl ether was added (*curve* 2). Thus, it was shown that ethyl alcohol containing diethyl ether can more effectively increase the octane number of gasoline A-80 [49], The content of 20–40% of such ethanol in gasoline A-80 increases its octane number to 91–95 U. While conventional 99.95% ethanol increases the octane number of gasoline A-80 only to 85–88 U. In the case of the maximum possible absolutized ethanol content up to 80–90% in gasoline A-80, the octane number reaches 91–93 U, and the introduction of the same amount of 99.95% ethanol containing 2.34% of diethyl ether in gasoline A-80, the octane number reaches 97–97.5 U [50].

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