Measurement and correlation of liquid–liquid equilibria and partition coefficients of benzothyophene and benzothyophene 1,1-dioxide for acetonitrile+n-octane system

Furuya, Takeshi; Yamagami, Souko; Yazu, Kazumasa; Saito, Ikuo; Miki, Keiji

doi:10.1016/j.fluid.2004.09.028

Cited by 11 publications

(18 citation statements)

References 7 publications

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“…There is a significant difference in the partition coefficients of unoxidized and oxidized sulfur compounds in two-phase liquids systems. For example, the partition coefficients of dibenzothiophene and dibenzothiophene-1,1-dioxide in an n -octane–acetonitrile system at 25 °C are 0.55:1 and 0.0043:1, respectively …”

Section: Resultsmentioning

confidence: 99%

“…For example, the partition coefficients of dibenzothiophene and dibenzothiophene-1,1-dioxide in an n-octaneÀ acetonitrile system at 25 °C are 0.55:1 and 0.0043:1, respectively. 65 (c) Biological desulfurization may be improved by oxidative pretreatment. 12 (d) Oxidized sulfur-containing compounds are more readily desulfurized during subsequent thermal treatment, including mild thermal cracking, such as encountered in visbreaking processes.…”

Section: Articlementioning

confidence: 99%

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Desulfurization of Heavy Oil–Oxidative Desulfurization (ODS) As Potential Upgrading Pathway for Oil Sands Derived Bitumen

Javadli

Klerk

2011

Energy Fuels

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Heavy oil usually contains percentage levels of sulfur. Most of the sulfur in heavy oil is found in bulky thiophenic structures. Thiophenic sulfur is difficult to remove by catalytic hydrodesulfurization, but it can readily be oxidized. The sulfoxides and sulfones produced from sulfur oxidation can be solvent extracted from the heavy oil as a result of their increased polarity. Oxidative desulfurization of heavy oil was studied using Canadian Cold Lake bitumen (5% S, 1100 kg/m3), with air as oxidant. At the conditions investigated, namely, autoxidation at 145–175 °C followed by water washing, 46–47% of the sulfur in the bitumen could be removed. This is equivalent to >20 kg sulfur per ton oil. Part of the sulfur was removed as SO2 and part as water extracted sulfur-containing compounds. Lower autoxidation temperatures led to better desulfurization. The main challenge was to prevent free radical addition reactions that cause a viscosity increase and bitumen hardening. Autoxidation of undiluted bitumen and bitumen–water mixtures resulted in hardening. Hardening was prevented when bitumen was diluted with naphtha (n-heptane). However, the oxidized sulfur compounds could not be extracted with water from the bitumen–heptane phase, and some material was precipitated as a result of solvent deasphalting. Oxidation selectivity was studied using a model dibenzothiophene and n-heptane mixture. Some precipitation was also observed, and the chemistry was analogous to the precipitation chemistry (gum formation) that undermines storage stability of transportation fuels.

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Section: Resultsmentioning

confidence: 99%

Section: Articlementioning

confidence: 99%

Desulfurization of Heavy Oil–Oxidative Desulfurization (ODS) As Potential Upgrading Pathway for Oil Sands Derived Bitumen

Javadli

Klerk

2011

Energy Fuels

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“…A detailed description of the measuring procedure has been presented elsewhere [4,10], so only a brief explanation is given here. The experiments were carried out in a magnetically stirred, jacketed equilibrium cell with a working volume of 100 cm 3 and the cell was sealed to prevent the evaporation of solvent.…”

Section: Procedures and Equipmentmentioning

confidence: 99%

Partition behaviour of benzoic acid in (water+n-dodecane) solutions at T=(293.15 and 298.15)K

Long

Wang

Yang

2008

The Journal of Chemical Thermodynamics

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“…Furuya et al , have reported experimental data of the liquid−liquid equilibria for acetonitrile + octane, + decane, and + hexadecane systems. The partition coefficients of benzothiophene and benzothiophene 1,1-dioxide in the octane/acetonitrile system have been also measured at 298−343 K . In addition to these measurements, the correlations or predictions can be a highly useful tool for the design and development of oxidative desulfurization processes.…”

Section: Introductionmentioning

confidence: 99%

“…It is very important for the oxidative desulfurization process design to recognize the liquid-liquid equilibria for fuel oil/ acetonitrile systems and the partitions of the sulfur compounds and their oxides in fuel oil/acetonitrile biphasic systems as fundamental knowledge. Furuya et al 5,6 have reported experimental data of the liquid-liquid equilibria for acetonitrile + octane, + decane, and + hexadecane systems. The partition coefficients of benzothiophene and benzothiophene 1,1-dioxide in the octane/acetonitrile system have been also measured at 298-343 K. 5 In addition to these measurements, the correlations or predictions can be a highly useful tool for the design and development of oxidative desulfurization processes.…”

Section: Introductionmentioning

confidence: 99%

Prediction of Partition Coefficients of Benzothiophene and Benzothiophene 1,1-Dioxide in Octane/Acetonitrile System Using COSMO Theory

Shimoyama

Iwai

Yoda

et al. 2008

Ind. Eng. Chem. Res.

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The partition coefficients of benzothiophene (BT) and benzothiophene 1,1-dioxide (BTDO) in the octane/ acetonitrile system were predicted using the COSMO (conductor-like screening model) based activity coefficient models COSMO-SAC (segment activity coefficient) and COSMO-UNIQUAC. In COSMO-UNIQUAC, a segment activity coefficient was described in a UNIQUAC-type equation. The results with COSMO-UNIQUAC were compared with those from the COSMO-SAC model. It was found that COSMO-UNIQUAC reproduced the experimental data more accurately than COSMO-SAC. The surface charge density profiles (σ-profiles) of functional groups on BT and BTDO molecules were utilized to determine that the partition coefficients of BTDO are much lower than those of BT. A hypothetical molecule with the volume and surface area of BTDO was conducted by using the σ-profiles of functional groups on BT and BTDO. The partition coefficients of the hypothetical component were predicted by COSMO-UNIQUAC. It was revealed that the partitions of BTDO in the octane/acetonitrile system were influenced from the charge density changes by the oxidation on not only the sulfur atom but also on the carbon and hydrogen atoms.

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Measurement and correlation of liquid–liquid equilibria and partition coefficients of benzothyophene and benzothyophene 1,1-dioxide for acetonitrile+n-octane system

Cited by 11 publications

References 7 publications

Desulfurization of Heavy Oil–Oxidative Desulfurization (ODS) As Potential Upgrading Pathway for Oil Sands Derived Bitumen

Desulfurization of Heavy Oil–Oxidative Desulfurization (ODS) As Potential Upgrading Pathway for Oil Sands Derived Bitumen

Partition behaviour of benzoic acid in (water+n-dodecane) solutions at T=(293.15 and 298.15)K

Prediction of Partition Coefficients of Benzothiophene and Benzothiophene 1,1-Dioxide in Octane/Acetonitrile System Using COSMO Theory

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