research article preparation of novel high-temperature...

Research ArticlePreparation of Novel High-Temperature Polyol Esters fromVegetable Oils

Can Liu12 Jing Liu1 Lanqing Ma2 and Long Rong1

1 School of Biological Science and Medical Engineering Beihang University Room 417 Yifu Scientific Center 37 Xueyuan RoadHaidian District Beijing 100191 China

2 School of Biological Science and Engineering Beijing University of Agriculture Beinong Road 7 HuilongguanChangping District Beijing 102206 China

Correspondence should be addressed to Long Rong ronglong64163com

Received 31 March 2014 Revised 23 May 2014 Accepted 25 May 2014 Published 16 June 2014

Academic Editor Lorenzo Cerretani

Copyright copy 2014 Can Liu et al This is an open access article distributed under the Creative Commons Attribution License whichpermits unrestricted use distribution and reproduction in any medium provided the original work is properly cited

The aim of this work was to synthesize a high-temperature polyol ester from Jatropha oil The synthesis process was accomplishedvia chemical modifications involving epoxidation to remove the double bonds in Jatropha oil hydrolysis to add hydroxyl groupsand then esterification with pentaerythritol to form the saturated polyol ester The high decomposition temperature 359∘C of thepolyol ester was determined by thermogravimetric analysisThe lower peroxide value 007meqkg and iodine value 002mg I

2

100 gof the polyol esters were also determined

1 Introduction

There are significant concerns regarding the current practiceof using mineral oils as the primary raw materials in thelubricants industry One major problem is that such oilschiefly derived from petroleum distillates are not necessarilysustainable in the long term Furthermore due to the inherenttoxicity and nonbiodegradable nature of some mineral oilbased lubricants they may present a contamination hazardwith respect to ecosystems agricultural land and groundwater reserves [1] As a result of these concerns there hasbeen increasing interest in the development of biolubri-cants derived from renewable resources such as vegetableoils [2 3] Vegetable oils are not only biodegradable andnontoxic but also possess properties which tend to makethem excellent lubricants These characteristics include highviscosity indexes low volatility good lubricity and highmiscibility with other fluids [4 5] However vegetable oilstypically exhibit poor thermal and oxidative stability [6]These drawbacks presently restrict the use of vegetable oilsas lubricants

Polyol esters exhibit extraordinary stability due to theabsence of hydrogen in the beta position as well as the

presence of a central quaternary carbon (1) Thereforethe thermal stability of vegetable oils can be improved byreplacing the glyceride moiety in the original moleculewith a polyhydric alcohol (such as trimethylolpropane orpentaerythritol) [7]

There are reports in the literature on the synthesisof polyol esters from vegetable oils [7 8] However suchpolyol esters retain unsaturated bonds in their fatty acidchain portions which represent sites where the compoundsmay still react with atmospheric oxygen (2) Therefore thecarbon-carbon double bond structure of the oil must becleaved by chemical modifications to improve its thermalcharacteristics

Previous research has shown that castor oil shows excel-lent stability due to its hydroxyl group and can formhydrogenbonding and prevent the formation of hydroperoxides [9] Itwas suggested that the existence of hydroxyl groups also playsa key role in improving the thermal stability of oils (3)Thusattaching hydroxyl groups to the polyol ester may be anotherway of improving its thermal stability

In accordance with the above-mentioned three methodsof improving the stability of vegetable oil the aim of thiswork was to design a high thermal polyol ester from Jatropha

Hindawi Publishing CorporationJournal of ChemistryVolume 2014 Article ID 802732 6 pageshttpdxdoiorg1011552014802732

2 Journal of Chemistry

+

OH

OH OH

OH

OH

O

C

C C C

CCC C

C

C

C C

H HO O H H O

O

OH

H O

O

O

HH H

H

H H

H H

H

O

O

FA

HFA

EFA

EFA

Formic acid Hydrogen peroxide+

+

+

+

H+

H+

H2O

H2O

Figure 1 Synthetic route of HFA from FA

oil via chemical modifications involving (1) epoxidation toremove the double bonds of Jatropha oil (2) hydrolysis toadd hydroxyl groups (3) esterification with pentaerythritolto form saturated polyol ester Moreover the structure andphysicochemical properties of the novel polyol ester were alsodetermined

2 Materials and Methods

21 Materials Jatropha oil was obtained from JiangsuDonghu Bio-energy Co Ltd Jiangsu China Formic acid(88) hydrogen peroxide (30) phosphotungstic acid(98) and pentaerythritol (98) were purchased fromSinopharm Chemical Reagent Co Ltd Shanghai China Allthe other reagents were of analytical grade

22 Methods The overall synthesis of saturated polyol estersfrom Jatropha oil involved three main steps These were asfollows saponification of the oil to produce the free fatty acidsubsequent synthesis of the corresponding hydroxylated fattyacid (HFA) and finally esterification to give the saturatedpolyol ester

221 Preparation of the Fatty Acid of Jatropha Oil The fattyacid (FA) of Jatropha oil was prepared via a two-step processThe initial step consisted of saponification of the oil in aNaOH solution at 50∘C for three hoursThe resulting alkalinesolutionwas then held at 55∘Candneutralized by the additionof a sufficient quantity of acid followed by washing withwater After washing the water was removed via rotaryevaporator under reduced pressure at 80∘C

222 Preparation of theHydroxylated FattyAcid Preparationof the hydroxylated fatty acid (HFA) involved sequentialoxidization and hydrolysis steps [10ndash12] The synthetic routeof HFA was represented in Figure 1 The oxidization reactionconditions were as follows 200 g FA and 30 g formic acid(88wt) were combined in a 500mL four-neck roundbottom flask equipped with a thermometer dropping funnelwater cooling condenser and mechanical stirrer A total of

180 g of hydrogen peroxide solution (30wt) were addedto the flask dropwise over 30min The reaction mixturewas continually stirred subsequent to the addition of theperoxide maintaining the temperature at 50∘C and sampleswere removed periodically and an iodine test for unsaturationwas applied The reaction was considered complete when theiodine test gave a value of zero meaning all double bonds inthe oil had been completely reactedThe subsequent step washydrolysis of the epoxidized fatty acid (EFA)Water (200mL)was added dropwise to the epoxide solution following whichthe mixture was heated to approximately 90∘C and stirred forfive hours This sequence of reactions very efficiently cleavesthe FA double bond and attaches hydroxyl groups at theformer site of unsaturation

223 Preparation of Polyol Esters Polyol esters were syn-thesized by the esterification reaction of either HFA or FAwith pentaerythritol (PE) [6 8] The synthesis of saturatedpolyol esters (SPE) was shown in Figure 2 The reaction wascarried out in a three-neck round bottom flask equippedwith a Dean-Stark water separator with constant stirringPhosphotungstic acid was employed as a catalyst at a con-centration of 2 wt (relative to the mass of the HFA) Thespecific reaction conditions included a temperature of 220∘Ca reaction time of 7 hours and amolar ratio ofHFAor FA PEof 43 1 Water formed as a byproduct of the reaction wascontinuously removed and the quantity of captured waterwas used to gauge the progress of the reaction When thereaction was complete portions of the reaction mixture wereremoved neutralizedwith alkaline solution and thenwashedwith warm (60∘C) water The resulting polyol esters weredried using a rotary evaporator under reduced pressure at85∘CThe reaction equation was as follows

4HFA + PE 999447999472 4SEP + 4H2O (1)

The esterification conversion can be calculated approxi-mately by the ratio of the amount of water actually generatedto that theoretically generated During the esterification pro-cess the amount of fatty acids is excessive and assuming thatthe PE reaction is completed the mole of water theoretically

Journal of Chemistry 3

O

R OH

OH

OH

OH OH

OH OH

OHOH

OHOH

OHOH

OH

OHOH

OHHFA

Esterification

PE

C

CH2OH

CH2OH

CH2OH

HOH2C

R4HCndashCHmiddot middot middotH2CCOOH2C

HO HO

CH2OOCCH2 middot middot middotHCndashCHR1

CH2OOCCH2 middot middot middotHCndashCH CH2 middot middot middotHCndashCHR2 + H2O

CH2OOCCH2 middot middot middotHCndashCH CH2 middot middot middotHCndashCH CH2 middot middot middotHCndashCHR3

Figure 2 Synthesis of SEP over a phosphotungstic acid catalyst

generated is four times the amount of PE For example if theamount of reactant PE is 02mol in theory the amount ofwater generated is 08mol in this reaction The relationshipbetween the mole of initial PE and the mole of watertheoretically generated could be expressed as follows

1198722=1198721

4 (2)

where 1198721is the mole of the generated water and 119872

2is the

mole of initial PEThe esterification conversion was calculated by the next

equation as follows

119862 =119872

181198722

times 100 = 211987219 (3)

where 119862 is the conversion and119872 is the actual mass of waterobtained after the esterification process

23 Physicochemical Properties Determination Fouriertransform infrared (FTIR) spectroscopy was used forstructural characterization Spectra were recorded with aFTIR spectroscope (Gangdong 650) over 500ndash4000 cmminus1using 32 scans at a resolution of 4 cmminus1 The thermalstability of each sample was examined using a STA 449Cthermogravimetric analysis (TGA) apparatus (NetzschWaldkraiburg Germany)

The iodine values of samples were determined in accor-dance with the ASTM D5554-95 standard method The

Tran

smitt

ance

()

(a)

(b)

(c)

344424

301014

84035

Wavenumbers (cmminus1)4000 3500 3000 2500 2000 1500 1000 500

Figure 3 FTIR spectra of FA (a) EFA (b) and HFA (c)

peroxide values of samples were determined according to theAOCS Cd 8-53 standard method

3 Results and Discussion

FTIR analysis was used to identify the products at differentreaction stages Figure 3 shows the spectra of the FA EFA


174226

344424

Tran

smitt

ance

()

(a)

(b)

(c)301014

344424

171055

174226


Figure 4 FTIR spectra of HFA (a) SPE (b) and UPE (c)

OH

OH OH

OHOH

OH

CR4HCndashCHmiddot middot middotH2CCOOH2C

HO HO



CH2OOCCH2 middot middot middotHCndashCHR 3

100

80

60

40

20

0

95

359∘C

Mas

s (

)

100 200 300 400 500 600 700

Temperature (∘C)

Figure 5 TGA thermogram of the SPE

and HFA products It is evident that following the oxidiza-tion reaction the peak at 3010 cmminus1 corresponding to thedouble bond stretching vibration is lost while a small peakat 840 cmminus1 due to the epoxide group appears [13] Thisconfirms the reaction of the double bond to the epoxide

As the subsequent hydroxylation reaction progressed itwas observed that the epoxide peak gradually diminishedwhile a hydroxyl band at approximately 3444 cmminus1 becameincreasingly prominent [14] At the completion of the reac-tion the complete disappearance of both the double bond


Table 1 Iodine and peroxide test data for Jatropha oil UPE andSPE

Parameter Jatropha oil UPE SPEIodine value (mg I2100 g) 10052 8943 002Peroxide value (meqkg) 1639 2352 007

(3010 cmminus1) and epoxide peaks (840 cmminus1) indicated thatall of the double bonds were successfully converted via theaddition of hydroxyl groups

The synthesis of SPE was accomplished by an esterifica-tion reaction between HFA and PE and 935 conversionwas obtained Initially unsaturated polyol esters (UPE) weresynthesized by the esterification of FA with PE As shownin Figure 4 after esterification there is a shift in the peak at1710 cmminus1 which is characteristic of FAs to 1742 cmminus1 whichcorresponds to the ester linkage confirming the formationof ester groups Comparing the spectra of SPE with UPE itis evident that there are significant differences in the peakscorresponding to both the hydroxyl group and the doublebond As expected the SPE is characterized by a broadhydroxyl stretching peak around 3444 cmminus1 and the completedisappearance of the double bond peak at 3010 cmminus1 whilethe UPE exhibits a peak for the double bond but not thehydroxyl group

The weight loss (TGA) curve acquired under a heliumatmosphere for the saturated polyol ester (SPE) is presentedin Figure 5 The starting temperature for thermal decompo-sition is taken as the temperature at which samples showed afive-percent weight loss It can be seen that the SPE displayedexcellent thermal stability and began to degrade at 359∘CThehigh decomposition temperature of the SPE can be explainedby the following reasons (1) the SPE has no hydrogen inthe beta position [8] (2) the SPE has hydroxyl groups andhence additional hydrogen bonding [15] (3) the SPE has nounsaturated bonds

Table 1 provides data concerning the values of iodineand peroxide tests for both the UPE and SPE as well asfor unmodified Jatropha oil Since the iodine value is ameasure of the unsaturation of fats and oils the SPE hasthe lowest value The peroxide value of an oil is consideredone of its most important parameters as it measures thetotal amount of peroxide in the oil and hence the extent towhich it has undergone oxidation As such since oxidativestability of oils can be defined as resistance to oxidationa low peroxide value for lubricants corresponds to betteroxidative resistance Table 1 shows that the peroxide valueof SPE is much lower than that of either pure Jatropha oilor the UPE since the SPE is saturated while the othersboth have a significant number of unsaturated sites whichare very sensitive to autoxidation and can be rapidly trans-formed into peroxides [16 17] These results confirm thatthe SPE has much better oxidative stability Vegetable oilbased lubricants however typically exhibit poor thermal andoxidative stability since the beta hydrogen on the glyceridemoiety is readily eliminated leading to subsequent cleavageof the ester into the corresponding acid and olefinThis workwas attempted to improve both the thermal and oxidative

stability of Jatropha vegetable oil This was accomplishedvia a series of chemical modifications involving epoxidationhydroxylation and finally esterification with pentaerythritolThis sequence of reactions works efficiently to add hydroxylgroups across the double bond within the Jatropha oil fattyacid as well as to eliminate the beta hydrogen on the glycerideportion of the molecule Compared to UPE (unsaturatedpolyol esters) SPE (saturated polyol ester) showsmuch loweriodine value and peroxide value

4 Conclusions

In this work a novel high-temperature polyol ester from Jat-ropha oil was successfully synthesized The high decomposi-tion temperature 359∘C of the polyol ester was determined bythermogravimetric analysis Compared with the rawmaterialJatropha oil the lower peroxide value 007meqkg and iodinevalue 002mg I

2100 g of the polyol esters were also obtained

Considering its high thermal stability the polyol ester mayprovide the conditions and potential for the development ofnew high-temperature lubricants

Conflict of Interests

The authors declare that there is no conflict of interestsregarding the publication of this paper

Acknowledgment

This work was supported by foundation of ldquoDa Bei Nongrdquo no13Z K001

References

[1] D R Kodali ldquoHigh performance ester lubricants from naturaloilsrdquo Industrial Lubrication and Tribology vol 54 no 4 pp 165ndash170 2002

[2] S Z Erhan and S Asadauskas ldquoLubricant basestocks fromvegetable oilsrdquo Industrial Crops and Products vol 11 no 2-3 pp277ndash282 2000

[3] HWagner R Luther and TMang ldquoLubricant base fluids basedon renewable raw materials their catalytic manufacture andmodificationrdquo Applied Catalysis A General vol 221 no 1-2 pp429ndash442 2001

[4] H-S Hwang and S Z Erhan ldquoSynthetic lubricant basestocksfrom epoxidized soybean oil and Guerbet alcoholsrdquo IndustrialCrops and Products vol 23 no 3 pp 311ndash317 2006

[5] R N M Kamil and S Yusup ldquoModeling of reaction kinetics fortransesterification of palm-based methyl esters with trimethy-lolpropanerdquo Bioresource Technology vol 101 no 15 pp 5877ndash5884 2010

[6] N H Arbain and J Salimon ldquoSynthesis and characterization ofester trimethylolpropane based Jatropha Curcas oil as biolubri-cant base stocksrdquo Journal of Science Technology vol 2 no 2 pp47ndash58 2011

[7] R N M Kamil S Yusup and U Rashid ldquoOptimization ofpolyol ester production by transesterification of Jatropha-basedmethyl ester with trimethylolpropane using Taguchi design ofexperimentrdquo Fuel vol 90 no 6 pp 2343ndash2345 2011


[8] S Gryglewicz W Piechocki and G Gryglewicz ldquoPreparationof polyol esters based on vegetable and animal fatsrdquo BioresourceTechnology vol 87 no 1 pp 35ndash39 2003

[9] D Ogunniyi ldquoCastor oil a vital industrial raw materialrdquoBioresource Technology vol 97 no 9 pp 1086ndash1091 2006

[10] P Tran D Graiver and R Narayan ldquoOzone-mediated polyolsynthesis from soybean oilrdquo Journal of the American OilChemists Society vol 82 no 9 pp 653ndash659 2005

[11] P Meyer N Techaphattana S Manundawee S Sangkeaw WJunlakan and C Tongurai ldquoEpoxidation of soybean oil andJatropha oilrdquo Thammasat International Journal of Science andTechnology vol 13 pp 1ndash5 2008

[12] A Adhvaryu and S Erhan ldquoEpoxidized soybean oil as apotential source of high-temperature lubricantsrdquo IndustrialCrops and Products vol 15 no 3 pp 247ndash254 2002

[13] L K Jia L X Gong W J Ji and C Y Kan ldquoSynthesis ofvegetable oil based polyol with cottonseed oil and sorbitolderived from natural sourcerdquo Chinese Chemical Letters vol 22no 11 pp 1289ndash1292 2011

[14] R Briones L Serrano R Llano-Ponte and J Labidi ldquoPolyolsobtained from solvolysis liquefaction of biodiesel productionsolid residuesrdquo Chemical Engineering Journal vol 175 no 1 pp169ndash175 2011

[15] Z S Petrovic W Zhang and I Javni ldquoStructure and propertiesof polyurethanes prepared from triglyceride polyols by ozonol-ysisrdquo Biomacromolecules vol 6 no 2 pp 713ndash719 2005

[16] HAzeredo J A F Faria andMAA P da Silva ldquoMinimizationof peroxide formation rate in soybean oil by antioxidantcombinationsrdquo Food Research International vol 37 no 7 pp689ndash694 2004

[17] A Dhaouadi L Monser S Sadok and N Adhoum ldquoFlow-injectionmethylene blue-based spectrophotometricmethod forthe determination of peroxide values in edible oilsrdquo AnalyticaChimica Acta vol 576 no 2 pp 270ndash274 2006

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Organic Chemistry International

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CatalystsJournal of


+

OH

OH OH

OH

OH

O

C

C C C

CCC C

C

C

C C

H HO O H H O

O

OH

H O

O

O

HH H

H

H H

H H

H

O

O

FA

HFA

EFA

EFA

Formic acid Hydrogen peroxide+

+

+

+

H+

H+

H2O

H2O

Figure 1 Synthetic route of HFA from FA

oil via chemical modifications involving (1) epoxidation toremove the double bonds of Jatropha oil (2) hydrolysis toadd hydroxyl groups (3) esterification with pentaerythritolto form saturated polyol ester Moreover the structure andphysicochemical properties of the novel polyol ester were alsodetermined

2 Materials and Methods

21 Materials Jatropha oil was obtained from JiangsuDonghu Bio-energy Co Ltd Jiangsu China Formic acid(88) hydrogen peroxide (30) phosphotungstic acid(98) and pentaerythritol (98) were purchased fromSinopharm Chemical Reagent Co Ltd Shanghai China Allthe other reagents were of analytical grade

22 Methods The overall synthesis of saturated polyol estersfrom Jatropha oil involved three main steps These were asfollows saponification of the oil to produce the free fatty acidsubsequent synthesis of the corresponding hydroxylated fattyacid (HFA) and finally esterification to give the saturatedpolyol ester

221 Preparation of the Fatty Acid of Jatropha Oil The fattyacid (FA) of Jatropha oil was prepared via a two-step processThe initial step consisted of saponification of the oil in aNaOH solution at 50∘C for three hoursThe resulting alkalinesolutionwas then held at 55∘Candneutralized by the additionof a sufficient quantity of acid followed by washing withwater After washing the water was removed via rotaryevaporator under reduced pressure at 80∘C

222 Preparation of theHydroxylated FattyAcid Preparationof the hydroxylated fatty acid (HFA) involved sequentialoxidization and hydrolysis steps [10ndash12] The synthetic routeof HFA was represented in Figure 1 The oxidization reactionconditions were as follows 200 g FA and 30 g formic acid(88wt) were combined in a 500mL four-neck roundbottom flask equipped with a thermometer dropping funnelwater cooling condenser and mechanical stirrer A total of

180 g of hydrogen peroxide solution (30wt) were addedto the flask dropwise over 30min The reaction mixturewas continually stirred subsequent to the addition of theperoxide maintaining the temperature at 50∘C and sampleswere removed periodically and an iodine test for unsaturationwas applied The reaction was considered complete when theiodine test gave a value of zero meaning all double bonds inthe oil had been completely reactedThe subsequent step washydrolysis of the epoxidized fatty acid (EFA)Water (200mL)was added dropwise to the epoxide solution following whichthe mixture was heated to approximately 90∘C and stirred forfive hours This sequence of reactions very efficiently cleavesthe FA double bond and attaches hydroxyl groups at theformer site of unsaturation

223 Preparation of Polyol Esters Polyol esters were syn-thesized by the esterification reaction of either HFA or FAwith pentaerythritol (PE) [6 8] The synthesis of saturatedpolyol esters (SPE) was shown in Figure 2 The reaction wascarried out in a three-neck round bottom flask equippedwith a Dean-Stark water separator with constant stirringPhosphotungstic acid was employed as a catalyst at a con-centration of 2 wt (relative to the mass of the HFA) Thespecific reaction conditions included a temperature of 220∘Ca reaction time of 7 hours and amolar ratio ofHFAor FA PEof 43 1 Water formed as a byproduct of the reaction wascontinuously removed and the quantity of captured waterwas used to gauge the progress of the reaction When thereaction was complete portions of the reaction mixture wereremoved neutralizedwith alkaline solution and thenwashedwith warm (60∘C) water The resulting polyol esters weredried using a rotary evaporator under reduced pressure at85∘CThe reaction equation was as follows

4HFA + PE 999447999472 4SEP + 4H2O (1)

The esterification conversion can be calculated approxi-mately by the ratio of the amount of water actually generatedto that theoretically generated During the esterification pro-cess the amount of fatty acids is excessive and assuming thatthe PE reaction is completed the mole of water theoretically


O

R OH

OH

OH

OH OH

OH OH

OHOH

OHOH

OHOH

OH

OHOH

OHHFA

Esterification

PE

C

CH2OH

CH2OH

CH2OH

HOH2C


HO HO






1198722=1198721

4 (2)


2is the


equation as follows

119862 =119872

181198722

times 100 = 211987219 (3)




Tran

smitt

ance

()

(a)

(b)

(c)

344424

301014

84035







174226

344424

Tran

smitt

ance

()

(a)

(b)

(c)301014

344424

171055

174226



OH

OH OH

OHOH

OH


HO HO




100

80

60

40

20

0

95

359∘C

Mas

s (

)

100 200 300 400 500 600 700

Temperature (∘C)












4 Conclusions






Acknowledgment


References




























Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of


O

R OH

OH

OH

OH OH

OH OH

OHOH

OHOH

OHOH

OH

OHOH

OHHFA

Esterification

PE

C

CH2OH

CH2OH

CH2OH

HOH2C


HO HO






1198722=1198721

4 (2)


2is the


equation as follows

119862 =119872

181198722

times 100 = 211987219 (3)




Tran

smitt

ance

()

(a)

(b)

(c)

344424

301014

84035







174226

344424

Tran

smitt

ance

()

(a)

(b)

(c)301014

344424

171055

174226



OH

OH OH

OHOH

OH


HO HO




100

80

60

40

20

0

95

359∘C

Mas

s (

)

100 200 300 400 500 600 700

Temperature (∘C)












4 Conclusions






Acknowledgment


References




























Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of


174226

344424

Tran

smitt

ance

()

(a)

(b)

(c)301014

344424

171055

174226



OH

OH OH

OHOH

OH


HO HO




100

80

60

40

20

0

95

359∘C

Mas

s (

)

100 200 300 400 500 600 700

Temperature (∘C)












4 Conclusions






Acknowledgment


References




























Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of









4 Conclusions






Acknowledgment


References




























Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of





















Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of

research article preparation of novel high-temperature...

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