Synthesis of fatty monoester lubricant base oil catalyzed by Fe-Zn double-metal cyanide complex

Raut, Ravindra K.; Shaikh, Mehejabeen; Srinivas, D.

doi:10.1007/s12039-014-0669-x

Cited by 10 publications

(4 citation statements)

References 20 publications

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“…For example, Co–Zn double-metal cyanides show a shift of this band from 2133 to 2187 cm –1 , compared to the precursor K 3 Co(CN) 6 . The ν(CN) shift to higher frequencies demonstrates that the CN ion acts as not only a σ-donor by donating electrons to Fe but also as a π-electron donor by chelating to Mn metal. , Additionally, the existence of complexing agent ( tert -BuOH) in the Fe–Mn catalyst was confirmed from the characteristic bands at 1440.7 cm –1 –1261.4 cm –1 (symmetric and antisymmetric C–H deformation and out-of-plane C 3 C–O antisymmetric stretching vibrations) and 1103.2 cm –1 (CH 3 rocking vibrations). ,, Furthermore, a broad band attributed to OH in H 2 O and tert -butanol was detected around 3650 cm –1 . , …”

Section: Results and Discussionmentioning

confidence: 85%

“…30,40 Additionally, the existence of complexing agent (tert-BuOH) in the Fe−Mn catalyst was confirmed from the characteristic bands at 1440.7 cm −1 −1261.4 cm −1 (symmetric and antisymmetric C−H deformation and out-of-plane C 3 C−O antisymmetric stretching vibrations) and 1103.2 cm −1 (CH 3 rocking vibrations). 21,41,42 Furthermore, a broad band attributed to OH in H 2 O and tert-butanol was detected around 3650 cm −1 . 21,42 Diffuse-Reflectance UV−Visible Spectra.…”

Section: ■ Introductionmentioning

confidence: 98%

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Transesterification of Propylene Carbonate with Methanol Using Fe–Mn Double Metal Cyanide Catalyst

Song

Subramaniam

Chaudhari

2019

ACS Sustainable Chem. Eng.

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A highly active and selective heterogeneous catalyst consisting of Fe–Mn double metal cyanide is reported for the transesterification of cyclic carbonates with methanol. Fe–Mn double metal cyanide complex with a Fe/Mn metal ratio of 8 was found to provide significantly higher TOF and stability for transesterification of propylene carbonate with methanol to dimethyl carbonate. The experimental results showed that Mn content has a significant influence on the catalytic activity. TEM and XRD analyses suggested that Fe–Mn complex represents a cubic crystalline structure. XPS analysis showed that all Fe exists in Fe2+ state. However, for the Mn element, 86.8% of Mn exists in Mn2+ state with only 13.2% in Mn4+ state. Furthermore, FTIR and DRIFT UV–vis results verified the formation of a new mixed-metal complex of ferrocyanide moiety and Mn ions via bridging cyanide ligands. NH3-TPD results showed that Fe–Mn double metal cyanide has a strong acidity, which correlates to the high activity of Fe–Mn double metal cyanide complex. The effects of catalyst loading, methanol/PC ratio, temperature, and different cyclic carbonate substrates (ethylene carbonate, propylene carbonate, and 1,2-butylene carbonate) on the initial reaction rate as well as concentration–time profiles are reported. Unique feature of this catalyst is also nonleaching characteristics during reaction and higher TOF unlike the conventional catalysts such as CaO. Compared with the results from Fe and Mn alone as catalysts, Mn in this complex was proposed to be acting as active species, while Fe acting as a metal-dispersing agent and a stabilizer of the cyano-bridged complex and ensures a truly heterogeneous catalyst. On the basis of this, a possible reaction mechanism was proposed. The results presented in this work provide useful insights on the reaction mechanism of transesterification using Fe–Mn double metal cyanide catalysts, which may also be useful to guide rational design of improved catalysts and process for transesterification of cyclic carbonates.

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Section: Results and Discussionmentioning

confidence: 85%

Section: ■ Introductionmentioning

confidence: 98%

Transesterification of Propylene Carbonate with Methanol Using Fe–Mn Double Metal Cyanide Catalyst

Song

Subramaniam

Chaudhari

2019

ACS Sustainable Chem. Eng.

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“…2-Ethylhexyl oleate is a commercially attractive emollient ester that finds application in the production of cosmetics, lubricants, drugs, foods, and chemicals. − Emollient esters are nontoxic and biodegradable, with good solubility in oils and fats. These compounds are used in the formulation of creams, lotions, antiperspirants, makeup, and sunscreen to maintain skin hydration and plasticity. ,, …”

Section: Introductionmentioning

confidence: 99%

Continuous Enzymatic Synthesis of 2-Ethylhexyl Oleate in a Fluidized Bed Reactor: Operating Conditions, Hydrodynamics, and Mathematical Modeling

Silva

Rangel

Aguiar

et al. 2020

Ind. Eng. Chem. Res.

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The continuous synthesis of 2-ethylhexyl oleate catalyzed by Candida antarctica lipase immobilized on magnetic poly(styrene-co-divinylbenzene) particles was performed in a solvent-free fluidized bed reactor (FBR). The effects of space time (6, 12, and 18 h) and bed porosity (0.866, 0.892, and 0.916) were investigated to determine the best operating conditions. Experimental results showed that high ester productivity (0.73 mmol g–1 h–1) and a satisfactory esterification yield (48.24%) were achieved at a space time of 12 h and a bed porosity of 0.892. It was also observed that the higher the bed porosity, the higher the mass transfer coefficient and, consequently, the reactor productivity. This finding can be explained by the high interstitial velocity of the fluidized bed bioreactor, which increases the mixing degree and improves mass transfer. A mathematical model accounting for internal and external particle transfer effects was proposed based on ping-pong bi–bi enzyme kinetics. The FBR was described in a simplified manner, considering an agitated tank reactor, a strategy that provided good correlation (R 2 = 0.991) between experimental and model results. Immobilized lipase showed high operational stability (half-life of 1716 h) qualifying as a promising biocatalyst for industrial-scale applications.

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“…Kleinaitė, Jaška, Tvaska, and Matijošytė (2014) synthesized 2-ethyl-1-hexyl oleate with 100% conversion in 10 hours at 60 C and a reduced pressure of 100-150 mmHg using Lipozyme TL IM lipase as the catalyst. Raut, Shaikh, and Darbha (2014) investigated the transesterification of methyl oleate with 2-EH using a solid Fe-Zn double-metal cyanide (DMC) complex catalyst, and up to 96.7% conversion was obtained at 180 C in about 4 hours. However, these catalysts are usually expensive, and in most of the experiments, the transesterification proceeded at a relatively slow rate.…”

Section: Introductionmentioning

confidence: 99%

Biolubricant Production of 2‐Ethylhexyl Palmitate by Transesterification Over Unsupported Potassium Carbonate

Zheng

Xie

et al. 2018

J Americ Oil Chem Soc

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Owing to the decrease of global oil price, development of downstream value-added products is important to biodiesel industry. In this study, we used palmitic acid methyl ester (PAME) as a starting material to produce 2-ethylhexyl palmitate (2-EHP), an environmentally friendly biolubricant product, which was derived from the transesterification of fatty acid methyl esters and long chain fatty alcohols. Conventional synthetic routes of 2-EHP have disadvantages, including high catalyst price, low conversion efficiency, and pollution issues. To solve these problems, in situ transesterification of PAME with 2-ethylhexanol (2-EH) was conducted over unsupported potassium carbonate as heterogeneous catalyst. The optimal reaction temperature, 2-EH to PAME molar ratio, and catalyst to PAME mass ratio were 180 C, 3:1, and 3.0 wt%, respectively. The PAME conversion reached up to 100% within 1 hour under the optimal conditions. In addition, a kinetic model describing the experimental data over a temperature range of 160-180 C was developed. The dependence of kinetic rate constant (k) on temperature was evaluated, and the activation energy (E a ) for the transesterification of PAME with 2-EH was calculated to be 57.04 kJ mol Nomenclature PAME palmitic acid methyl ester 2-EHP 2-ethylhexyl palmitate 2-EH 2-ethylhexanol WCO waste cooking oil DMC double-metal cyanide complex catalyst GC gas chromatography IC ion chromatography A 2-EHP the peak area of 2-EHP A PAME the peak area of PAME f 2-EHP the response factor of 2-EHP to PAME X i the concentration of potassium ions in sample c i the concentration of potassium ions in the measured solution c 0 the concentration of potassium ions in the blank solution V the dilution coefficient m the mass of the sample X PAME degree of PAME conversion t time (min) m cat the mass ratio of catalyst (g) cat catalyst T reac reaction temperature ( C) reac reaction r PAME reaction rate (mol L

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Synthesis of fatty monoester lubricant base oil catalyzed by Fe-Zn double-metal cyanide complex

Cited by 10 publications

References 20 publications

Transesterification of Propylene Carbonate with Methanol Using Fe–Mn Double Metal Cyanide Catalyst

Transesterification of Propylene Carbonate with Methanol Using Fe–Mn Double Metal Cyanide Catalyst

Continuous Enzymatic Synthesis of 2-Ethylhexyl Oleate in a Fluidized Bed Reactor: Operating Conditions, Hydrodynamics, and Mathematical Modeling

Biolubricant Production of 2‐Ethylhexyl Palmitate by Transesterification Over Unsupported Potassium Carbonate

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