Crystalline Manganese Carbonate a Green Catalyst for Biodiesel Production

doi:10.4236/gsc.2012.21003

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Green and Sustainable Chemistry, 2012, 2, 14-20

http://dx.doi.org/10.4236/gsc.2012.21003 Published Online February 2012 (http://www.SciRP.org/journal/gsc)

Crystalline Manganese Carbonate a Green Catalyst for

Biodiesel Production

Yerraguntla Rajeshwer Rao1, Pudukulathan Kader Zubaidha2, Jakku Narender Reddy1,

Dasharath Dattatraya Kondhare2, Deshmukh Shivagi Sushma2

1Department of Chemis try, Govt. City College , Hyderabad, Indi a

2School of Chemical Sciences, Swami Ramanand Teerth Marathwada University, Nanded, India

Email: [email protected]

Received December 19, 2011; revised January 26, 2012; accepted February 7, 2012

ABSTRACT

Crystalline manganese carbonate was found to be a versatile green, non corrosive and environmental friendly catalyst

for transesterification of vegetable oils. Its use as catalyst in the transesterification process involving methanol and

vegetable oils (palm, rapeseed, groundnut, coconut and caster oils) resulted in a conversion rate of 80% - 95% in the

production of biodiesel. The chemical composition of the obtained biodiesel was studied by GC-MS analysis and

showed the presence of linoleic, oleic, palmitic, and stearic acids methyl esters to be the major compounds. Manganese

carbonate in comparison with other solid catalysts was found to decrease the reaction time and temperature concomitant

with an increase of biodiesel yield. Finally, the effect of various parameters including methanol quantity, catalyst

amount, reaction time and temperatures on the production of biodiesel was investigated.

Keywords: Biodiesel; Vegetable Oils; Manganese Carbonate; Green Catalyst; Transesterification

1. Introduction

Rising petroleum prices and continuous increase of pe-

troleum usage may drive the world, in near future, to feel

the pinch of deficiency of transportation fuels. Biodiesel

as an alternative fuel for diesel engines is becoming in-

creasingly important due to diminishing petroleum re-

source [1,2]. Various attempts are being made for the

search of new catalysts and vegetable oil sour ces, in trans-

esterification reactions, for the production of biodiesel [3-

5]. Biodiesel synthesis using solid catalysts instead of ho-

mogeneous catalysts could potentially lead to cheaper pro-

duction cost by enablingreu se of the catalyst. Biodiesel is

produced by the transesterification of triglycerides of re-

fined or edible and non-edible oils by using alcohol and

alkaline catalyst. The transest eri fi cati on process consists of

seq uences of three consecutive reversible reactions, which

includes conversion of triglycerides to diglycerides, fol-

lowed by diglycerides to monoglycerides. The glycerides

are converted in to glycerol and yield one ester molecule

in each step [6]. The overall transesterification reaction

can be represented by the following Scheme 1. The reac-

tion is normally performed at reflux temperature; the gly-

cerol and FAME (fatty acid methyl ester) are separated

by settling after catalyst neutralization. The crude biodie-

sel and glycerol obtained are then purified. There are dif-

ferent transesterification processes that can be applied to

Scheme 1. Transesterification of triglycerides with alcohol.

Y. RAJESHWER RAO ET AL. 15

synthesize biodiesel like base catalyzed transesterifica-

tion, acid catalyzed transesterification and enzyme cata-

lyzed transesterification [4]. Biodiesel is currently syn-

thesized using homogeneous acid catalysts, the rate of

reaction much slower than the base catalyzed reaction.

There are several comprehensive studies of base catalyzed

transesterification. The most common basic catalysts are

potassium hydroxide (KOH) and sodium hydroxide

(NaOH) [7,8]. Even though homogeneous catalyzed bio-

diesel production process are relatively fast and show high

conversion with minimal side reactions, they are still no t

very cost effective with petrodiesel. The transesterifica-

tion reaction can also be catalyzed by Bronsted acids pre-

ferably sulphonic and sulphuric acids, but the reaction

rates are very low and require relatively high temperatur e

to get the high product yield [9]. According to an acid ca-

talyzed mechanism for esterification, carboxylic acid can

be readily formed by hydrolysis of the carbocation inter-

mediate formed upon protonation of the ester. This sug-

gests that acid catalyzed transesterification should be car-

ried out in the absence of the water to avoid the compete-

tive formation of carboxylic acids and concomitant re-

duction in the yields of alkyl ester [10]. The most com-

mon acid catalysts used are H2SO4 and HCl. The scientist

Freedman et al showed that the methanolysis of soybean

oil, in the presence of 1 mol% of H2SO4 with an alco-

hol/oil molar ratio of 30:1 at 65˚C, takes 50 hrs to reach

complete conversion of the vegetable oil [11]. The trans-

esterification of oils is also carried out by solid super

acids such as tungustated zirconia-alumina (WZA), sul-

phated tin oxide (STA) and sulphated zirconia-alumina

(SZA), of which the WZA catalyst was the most effect-

tive achieving conversion >90% at temperature above

250˚C after 20 h [12]. Current industrial catalysts for bio-

diesel are based on the basic catalyst mentioned above

require pretreatment of the feedstock to remove impuri-

ties, water and the free fatty acids (which precludes the

use of low quality feedstocks such as waste oils) [13,14].

They also lead to saponification (i.e. soap formation) of

vegetable oil, which occur as an undesired side reaction

and necessities lengthy after process separation proce-

dures. These productio n steps negate the low price of the

catalyst and are energy intensive. It is therefore necessary

to develop new environmentally benign, inexpensive and

effective catalysts which avoid the costly saponification

reaction. A wide range of alternatives have been propo-

sed but to date none are ideal. In this work, manganese

carbonate (MnCO3) was found to be a versatile catalyst

in transesterifiction reaction to produce monoalkyl ester

(biodiesel). In this communication manganese carbonate

was found to be a versatile catalyst with 80% - 95% con-

version rate in the production of biodiesel involving, ve-

getable oils like palm oil, rapeseed oil, groundnut o il, co-

conut oil and castor oil. Although palm oil and rapeseed

oil are extensively used for biodiesel production the other

oils mentioned are studied for comparison purposes.

2. Experimental Details

2.1. Materials

All chemicals used in the experiments such as methanol

(99.5%), chloroform, petroleum ether, sodium sulphate,

sulphuric acid were of analytical regent grade and silica

gel G LR for TLC were purchased from Sarabhai Divi-

sion Fine Chemicals (Mumbai, India). Refined palm, sun-

flower, groundnut, coconut, rapeseed and castor oils were

purchased from local food store. Pure, ash colored, crys-

talline manganese carbonate was purchased fro m Chemi-

cal Corporation (Mumbai, India).

2.2. Transesterification

Transesterification process was performed in 25 ml round

bottom flask with reflux condenser and a magnetic stirrer.

Stirring was set at constant speed throughout the experi-

ment. The manganese carbonate in methanol ( 0.5% - 3%

w/v) was used for the conversion of oil to fatty acid me-

thyl ester (FAME), other oil to methanol ratio varied

from 5:1 to 12:1 v/v. A known amount of catalyst was

added in the required amount of methanol and was hea-

ted separately at desired temperature. This methanolic ca-

talyst was added to the preheated oil and the reaction was

kept under reflux condition. Formation of methyl ester

from vegetable oil was monitored by thin layer chroma-

tography. After reaction completion, the formed methyl

esters mixture was extracted with chloroform dried over

sodium sulphate. Chloroform was evaporated using a ro-

tary evaporator and the obtained methyl esters mixture

was then subjected to GC-MS analysis.

2.3. Analysis of Fatty Acid Methyl Esters

Gas chromatography has been to date the most widely

used method for the analysis of biodiesel due to its hi-

gher accuracy in unifying minor components [15]. The

sample was analyzed with shimadzu GC-2010 gas chro-

matograph equipped with splitless injection system. He-

lium was used as carrier gas. The cond ition of instrument

were: column oven temperature 75˚C, injection tempera-

ture set at 280˚C, the detection was made with a flame

ionization detector (FID) at 310˚C, flow control mode in

linear velocity with 26.0 cm/sec, total flow 14.0 ml/min,

column flow 1.0 ml/min, purge flow 3.0 ml/min, pressu r e

131.6 Kpa where as the split ratio 10.0. Samples were

prepared for analysis by adding approximately 0.05 gm

of oil phase to 5 ml of n-hexane. About 1 ml of this mix-

ture was put in to GC auto sampler vials. Two micro li-

ters of the sample were injected in to the column.

Y. RAJESHWER RAO ET AL.

2.4. Recovery of Catalyst

The catalyst thoroughly washed 4 - 5 times with water

for 35 hrs. After complete drying, the catalyst was re-used

for transesterification reaction. The obtained results showed

a catalytic efficiency of 95% and decreased after 7 times

uses.

2.5. Fuel Properties of Fatty Acid Methyl Esters

The product of above transesterification was analyzed,

taking into consideration specifications for biodiesel as

fuel in diesel engines. The following properties of the

biodiesel produced were determined: Density, Acid value,

Cloud point, Pour point, Viscosity (By Redwood vis-

cometer), Flash point (By Cleveland’s open cup appara-

tus). Most of these parameters comply with the limits

prescribed in the ASTM D6751-02 standards for bio-

diesel. Each experiment was conducted in triplicate and

the data reported as mean.

3. Results and Discussion

3.1. Composition of Oil

The palm oil was found to give the highest oil yield with

5000 kg oil per hectare; this value is far higher than other

oils which are in th e range of hund reds to 200 0 kg oil p er

hectare. The oil yield from the crops itself is always the

key factor to decide the sustainability of feed stock for

biodiesel production. Oil crops with higher oil yield are

more preferable in the biodiesel indu stry because it redu-

ces the production cost. The important criteria to deter-

mine the sustainability o f oil as feedstock for biodiesel is

its composition which will subsequently determine the pro-

perties of the obtained biodiesel. The composition of the

palm, sunflower, groundnut, coconut, rapeseed and castor

oils are well reported in literature as shown in

Table 1 The results showed that the Palm oil contains

the 85% saturated acids (palmitic and stearic) and 15%

unsaturated acids (linoleic, oleic). Rapeseed oil contains

86.4% unsaturated acids and only 4.4% saturated acid.

Sunflower and castor oil showed high content of linoleic

73% and ricinoleic acid 89% respectively. The different

results obtained in the properties of biodiesel is due to

the variation of compositions of oils. The palm oil has

40% oleic and 45% palmitic acid as major components

and the composition of sunflower, coconut, rapeseed, cas-

tor oils differ in th e fatty acid compositions. The rapeseed

oil has 64% of oleic acid as major component. This could

be the reason why this is preferred oil for the production

of biodiesel in Europe. In contrast castor oil has 89.5% of

recinoleic acid as major component which forms resins

as effects transesterification and so is not a preferred oil

for the producing biodiesel. By an d large the oils studied

exhibit 85% and above composition of saturated acids

and facilitate the pro duction of biod iesel in large q u antity.

The oil composition of palm, sunflower, groundnut, co-

conut, rapeseed and castor oils is shown in Table 1.

3.2. Analytical Results

In order to study the obtained biodiesels composition,

GC-MS analysis was used for the determination of the

composition of the ob tained fatty acid methyl esters. The

retention times in minute for palm, sunflower, coconut

and rapeseed oils are 10.763 - 26.885, 10.893 - 27.300,

14.739 - 26.380 and 10.763 - 26.885 respectively. The

percentage for palm, sunflower, coconut and rapeseed

oils are 100.01%, 99.99%, 100%, and 100.01% respect-

tively. The obtained qualitative and quantitative analysis

and the result of methyl ester components in palm and

sunflower transesterification products are presented in

Table 2.

The Table 2 indicates that the FAME from sunflower

oil contained mainly methyl linoleate (47.43%) and me-

thyl oleate (32.49%), which are comparable to fatty acid

composition of same feedstock. While palm oil methyl

esters consisted mainly of methyl p almitate (42.42 %) an d

oleate (47.04 %).

Table 1. Composition of various oils in %.

Fatty acid

composition (%) Molecular formula Palm Sunflower Coconut Rapeseed Castor

Oleic C18H34O2 40.0 16.93 0.3 64.1 3.0

Linoleic C18H32O2 10.0 73.73 0.2 22.3 4.2

Palmitic C16H32O2 45.0 6.8 0.2 3.5 1.0

Stearic C18H36O2 5.0 3.26 0.2 0.9 1.0

Linolenic C18H30O2 - 00 - - 0.3

Eicosenoic C20H38O2 - - - - 0.3

Ricinoleic C18H34O3 - - - - 89.5

Dihydroxysteric C18H36O4 - - - - 0.7

Palmitoleic C16H30O2 - - - 0.1 -

Myristic 0.3

Others - - - - 9.1 -

Y. RAJESHWER RAO ET AL. 17

Table 2. The analytical results of components of FAME from various vegetable oils using MnCO3 catalyst.

Methyl ester Palmoil % Sunflower % Coconutoil % Rapeseed oil %

Methyl laurate 0.41 0.06 54.39 0.41

Methyl myristate 1.24 0.10 21.40 1.24

Methyl palmitate 42.42 14.96 10.58 42.42

Methyl palmitoleate 0.28 1.10 0.24 0.28

Methyl stearate 3.30 3.85 1.69 3.30

Methyl oleate 47.04 32.49 6.41 47.04

Methyl linoleate 5.32 47.43 5.29 5.32

3.3. Fuel Properties of Methyl Esters

The fuel properties of the obtained biodiesel are sum-

marized in Table 3 together with the relevant specifica-

tions in the ASTM biodiesel standards [16-19]. The pro-

perties of methyl esters obtained from different oils were

compared with ASTM biodiesel standards. The results

are shown in Table 3. Viscosity of the methyl esters ob-

ta ined from the different stud ied oils was wit hin the stand-

ard range of 3.5 - 5.0 mm2/s at 40˚C. Hence no negative

impact on fuel injector’s system performance means pro-

duced biodiesel can be use in existing diesel engine. Flash

point measures the tendency of the sample to form flam-

mable mixture with air under controlled laboratory con-

ditions. This is the only p roperty that must be considered

on assessing the inflammability hazard of the material.

The flash point of methyl esters of studied oils is above

the specification limits and is safe for transpor t.

In comparison with other solid catalysts such as KF/

MgAl hydrotalcite, CaO-supported catalysts (Li/Cao, Na/Cao,

K/Cao) was the effective achieving conversion more than

85% [12,16,20-23]. Manganese carbonate was found to

be a green versatile catalyst which gives high biodiesel

yield at low temperatures. Use of manganese carbonate

may lead to cheaper production cost by enabling reuse of

the catalyst and opportun ities to op erate in fixed bed con -

tinuous process. The process offers advantages in terms

of mild conditions, high conversion and practical viabil-

ity and may find commercial application for the biodiesel

production.

3.4. Effect of Methanol to Oil Ratio

The amount of alcohol added to vegetable oil is one of

the important factors that affect conversion efficiency as

well as production cost of biodiesel. The conversion effi-

ciency is defined as the yield of the process represented

in terms of percentage. Generally the amount of alcohol

required for transesterification reaction is analyzed in

terms of volumetric ratio. Stoichiometriclly, the alcohol/

oil molar ratio is 3:1. Higher amount of alcohol is re-

quired to drive the reaction to completion at faster rate. It

is observed that lower amount of alcohol requires longer

reaction periods. The conversion efficiency of transeste-

rification reaction with increasing amount of alcohol ob-

tained during present study is shown in Figure 1. The tran-

sesterifiction reaction was studied for different molar

ratios. The methanol to oil molar ratio varied from oil to

oil. The maximum ester conversion for palm oil was

found to be 90% - 95% with a methanol to oil ratio of 5:1.

In the case of sunflower and rap eseed oil maximum yield

of 90% was obtained at 7:1 methanol oil ratio. The ground-

nut oil requires 9:1 ratio for the maximum conversion,

while in case of coconut and castor yield achieved was

75% at 12:1 methanol to oil ratio which gives highest

conversion of oil to methyl ester. Figure 1 depicts the

effect of alcohol to oil molar ratio on the conversion of

oil to methyl ester.

3.5. Effect of Catalyst Amount

The catalyst amount in the range 0.5% - 3.0% (Weight of

catalyst/volume of oil) is used in the present experiment-

tal analysis. The effect of catalyst amount on conversion

efficiency is shown in Figure 2. The obtained results

showed that the yield of palm and rapeseed oil was 95%

and 90% obtained with a 1% of catalyst amount while

sunflower and groundnut oil gave better yields, 90% and

85% respectively with 1.5% catalyst amount. Finally, th e

yield of 75% was obtained in the case of castor and co-

conut oils with 1.5% and 2.0% catalyst amount - respec-

tively.

3.6. Effect of Reaction Temperature

Although the reflux temperature was in general 600˚C -

80˚C, the reactions temperature and the obtained results

are shown in Figure 3 and showed that the temperature

required for the complete conversion of oil to fatty acid

methyl esters varied from oil to oil. In the case of palm

and sunflower oils, highest yield of 95% and 90% were

obtained at 60˚C respectively, while for groundnut, co-

conut, rapeseed and castor oils, the optimum yields ob-

tained were 85%, 75%, 90% and 75% respectively and

were obtained at 70˚C. It was observed that for reaction

temperature below 60˚C, saponification of glycerides oc-

curs very fast.

Y. RAJESHWER RAO ET AL.

Table 3. Fuel properties of produced fatty acid methyl esters.

Properties Palm oil Sunflower Coconut Rapeseed Castor

ASTM biodiesel

standard

Viscosity mm2/s at 40˚C 4.42 3.26 3.9 3.51 5.0 3.5 - 5.0

flash point (˚C) 162 180 171 150 190 130 min

Cloud point (˚C) 5 4 6 –4 –3 –3 - 12

Pour point (˚C) 10 9 9 –12 –8 –15 - 10

Density Kg/m3 0.92 0.92 0.91 0.91 0.96 0.87- 0.90

Acid value mg KOH/g 0.1 0.15 0.3 0.89 2.0 0.5

Figure 1. Effect of methanol/oil molar ratio.

Figure 2. Effect of amount of catalyst.

Figure 3. Effect of reaction temperature.

Figure 4. Effect of reaction time.

3.7. Effect of Reaction Time

In order to study the effect of reaction of reaction time,

experiments were carried out between 30 to 210 min for

the studied oils and the obtained results are depicted in

Figure 4. The obtained results showed that palm and sun-

flower oils achieved highest yield of 95% and 90% re-

spectively at 60 min under reflux conditions. Groundnut

and rapeseed oil gives 85% and 90% yield at 120 and

150 min respectively; while the transesterifiction yield of

75% was obtained in case of coconut and castor oils

maximum time of 180 minutes was sufficient for the

completion of reaction with highest yield of biodiesel .

3.8. Recovery and Reuse of Catalyst

Recovery of catalyst from the reaction mixture is an im-

portant operational parameter. From a financial economic

point of view, the use of heterogeneous catalyst in bio-

diesel production could reduce its price becoming com-

petitive with diesel. The used catalyst was recovered and

reused for further transesterification reactions. Th e obtai-

ned results showed the recovered catalyst was still effici-

ent even after seven successive uses. This suggests that

the use of manganese carbonate could be a fruitful ap-

proach for biod iesel production.

Y. RAJESHWER RAO ET AL. 19

4. Conclusion

In this paper, we have evaluated the catalytic activity of

crystalline MnCO3 as green catalyst since MnCO3 is non

corrosive, easy to handle and environmentally friendly

and an alternative low cost catalyst. MnCO3 efficiently

promote the transesterification in methanol solutions and

in the presence of vegetable oils. The high yields achiev-

able under mild reaction conditions are comparable to

those obtained with a common acid catalyst such as acid

and base. Therefore it is demonstrated that, MnCO3 is a

potential catalyst for the produ ction of biodiesel which is

a low-cost raw materials. The advantage of this protocol

is the use of an available low-cost catalyst, which is easy

to manipulate and potentially less corrosive. The results

of this work suggest MnCO3 as a promising alternative

catalyst for the produ ction of biodiesel. As a final remark ,

we believe that the application of MnCO3 potentially

promote a reduction of the costs related to biodiesel pro-

duction.

5. Acknowledgements

The financial support provided by University Grants Com-

mission, New Delhi, F.No.34-316/2008 (SR) is gratefully

acknowledged. The authors also thank the Principal, Dr.

C.S.N.Sharma, Govt. City College, Hyderabad-500002 for

kind cooperation and encouragement.

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