Reactor Pt Proces Continuu Biodiesel

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An ASAE/CSAE Meeting Presentation Paper Number: 046071

A Continuous-flow Reactive Distillation Reactor forBiodiesel Preparation from Seed Oils

Arvinder P. Singh, Joe C. Thompson, B. Brian He

Biological & Agricultural Engineering Department, University of IdahoMoscow, ID 83844-2060,USA

Written for presentation at the2004 ASAE/CSAE Annual International Meeting

Sponsored by ASAE/CSAEFairmont Chateau Laurier, The Westin, Government Centre

Ottawa, Ontario, Canada1 - 4 August, 2004

Abstract.In biodiesel preparation from vegetable oils and alcohol through transesterification processin the presence of a catalyst, excess alcohol, typically 100% more than the theoretical molarrequirement, is used in existing batch and continuous-flow processes in order to drive the reversibletransesterification reaction to a high enough conversion rate. The excess alcohol needs to berecovered in a separate process which involves additional operating and energy costs. In this study,a novel reactor system using reactive distillation (RD) technique was developed and studied forbiodiesel preparation from yellow mustard seed oil. The main objective was to dramatically reducethe use of excess alcohol in the feeding steam, which reduces the cost in downstream alcoholrecover processes, and meanwhile maintain a high alcohol-to-oil molar ratio inside of the RD reactor,which ensures the completion of the transesterification of seed oil to biodiesel. A lab scale sieve-trayRD reactor system was developed and used in this study. Process parameters were studied on theeffect of reduced alcohol to oil ratio on the overall quality of biodiesel product and the efficiency ofsuch an RD reactor. Product parameters such as methyl ester content, viscosity, total glycerol, andmethanol content were analyzed as per ASTM methods. Preliminary results showed that processparameters of methanol-to-oil ratio of 4:1 (molar) and a column temperature of 65C produced abiodiesel that met the ASTM standards for total glycerol and viscosity.

Keywords. Biodiesel, Reactive Distillation, Transesterification, Seed Oils


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ACONTINUOUS-FLOW REACTIVE DISTILLATION REACTOR FORBIODIESEL PREPARATION FROM SEED OILS

Arvinder P. Singh, Joe C. Thompson, B. Brian He 1

IntroductionIt has necessitated the governments, research communities, and private organizations aroundthe world to look for alternative and renewable sources of energy due to the depletion ofpetroleum reserves, increase in energy demands, unpredictability of fossil oil production, andincreased concerns of rising greenhouse gas emissions. To date, many alternatives have beenresearched and demonstrated but only a few have been proven to be practically feasible interms of availability, economics, public and environmental safety, and simplicity of use. Onesuch possible alternative is biodiesel from vegetable oils, used at 100% or blended with dieselfuel for compression-ignition type engines. Several studies have showed that biodiesel is abetter fuel than fossil-based diesel in terms of engine performance, emissions reduction,lubricity, and environmental benefits (Peterson et al., 1997; Canakci and VanGerpen, 2000).

Biodiesel can be made from vegetables oils or animal fats though transesterification oralcoholysis, enzymatic or lipase conversion, and thermal cracking or pyrolysis. In pyrolysismethod, fatty oils molecules were thermally or catalytically converted into hydrocarbons mainlyalkanes and alkenes, which are further fractionated to produce biogasoline and biodiesel. Theequipment and operating cost for pyrolysis is expensive. The most commonly used method istransesterification of vegetable oils or fats with methanol or ethanol in the presence of acatalyst. The reaction is shown in fig. 1.

Figure 1. Transesterification of seed oils to produce fatty acid esters

Because the reaction is reversible, excess alcohol is used to the shift the equilibrium to theproducts side. The completion of the transesterification reaction involves multiple parametersincluding the molar ratio of oil-to-alcohol, catalysts, reaction temperature, reaction time, and freefatty acids and water content of oils or fats. The mechanism and kinetics of biodiesel productionhave been studied by many researchers (Noureddini, 1997; Darnoko et al., 2000; Freedman etal., 1986). These studies show that transesterification consists of a number of consecutive,

reversible reactions. Triglycerides are first reduced to diglycerides. The diglycerides aresubsequently reduced to mono-glycerides. Lastly, the mono-glycerides are reduced to fatty acidesters and glycerol. The order of the reaction changes with the reaction conditions.

Alkali-catalyzed batch transesterification process is simple and, therefore, was often used incommercial processes (Ma and Hanna, 1999). The reaction mechanism and effects of process

1 Corresponding Author, Biological and Agricultural Engineering, University of Idahom,81A JML, Moscow, ID 83844-2060; Phone:208-885-7435; Fax: 208-885-8923; Email: [email protected]

R2OOCCH

CH2OOCR1

CH2OOCR3

HOCH

CH2OH

CH2OH

R1COOR4

+ R2COOR4

R3COOR4

+ 3R4OHCatal s

Seed oil Alcohol Glycerol Esters

(triglycerides)


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parameters have been widely studied. Most of the studies were published as patents. At theUniversity of Idaho, Peterson et al. (1991) characterized a batch transesterification process ofwinter rapeseed oil. A 6:1 molar ratio of methanol to oil or 100% excess gave the bestconversions in 60 min in a batch system. Ma et al. (1998a) reported the reaction proceeded veryfast from one to 5 min then slowed down and reached the maximum conversion at about 15 minwhen a ratio of 6 moles of methanol per mole of oil and 0.3% NaOH were used. Freedman et al.

(1984) transesterified peanut, cottonseed, and sunflower oils used the same methanol to oilratio and 0.5% sodium methoxide as catalyst at 60C. A yield of about 80% on soybean andsunflower oils was observed after 1 min.

Batch methods for biodiesel production are slow, tedious, labor intensive, and low inproductivity. Continuous transesterification processes are preferred over batch processes incommercial production. The basic advantages of continuous-flow process are a greaterproductivity and a consistent product quality. Continuous transesterification of seed oils wasstudied as early as the 1940s (Trent, 1945; Allen et al., 1945). It involves transesterification,separation of the co-product glycerol, washing of the ester product, and the recovery/recycle ofthe excessive alcohol. Such a continuous process usually involves an elevated temperature(120C to 160C). Recently, Noureddini et al. (1998), Peterson et al. (1999c), and Darnoko andCheryan (2000) have also investigated continuous transesterification processes using differentfeedstocks. At the University of Idaho, a continuous biodiesel process using ladder typeretention reactor was demonstrated (Peterson et al., 2000). The process utilized rapeseed oiland ethanol input at 1:6 molar ratio. An optimization study for biodiesel production by sunfloweroil transesterification conducted by Antolin et al. (2002) used three times the stoichiometricquantity of methanol (0.28% w/w of potassium hydroxide to oil), 70C temperature and twowashings, one with slightly acidic (phosphoric) water and the other with pure water. Almost all ofthe existing processes utilize excess alcohol, which must be recovered in additional separationprocess. This recovery process generally involves distillation, which increases energyconsumption and process time.

This research explores the applicability of homogenous reactive distillation (RD) technique fortransesterification of seed oils for biodiesel preparation. Reactive distillation is a technique of

simultaneous implementation of chemical reactions and distillation in a counter-current column.This process has less recycle streams and a reduced need for waste handling, which translatesinto lower investment and operating costs. In some applications particularly when reversiblereaction equilibrium prevents high conversions, the RD technique can be employed to removethe reaction products from the reaction zone thus improves overall conversion rate andselectivity. In other applications, reactions are utilized to overcome the separation problemscaused by azeotropes. Some of the representative applications of RD techniques are in theproduction of methyl tertiary butyl ether (MTBE), ethyl tertiary butyl ether (ETBE), tertiary amylmethyl ether (TAME), methyl acetate, ethyl acetate, and butyl acetate.

The operation of RD process is quite complicated and its performance is influenced by severalparameters including the size of reaction and separation zones, reflux ratio, and feed rate andtray location (Solokhin, 1996; Tuchlenski et al., 2001). A conceptual design of catalytic reactivedistillation for fatty acid esterification was discussed by Omata et al. (2003). The RD processcan be performed in either tray or packed columns, however, tray columns are recommendedfor homogenous systems because of the greater holdup and the associated longer residencetime. For reactions that are not severely equilibrium-limited, the initial reaction rate is high, butdeclines abruptly when compositions and temperatures approaches equilibrium. For such casesa pre-reactor should be used upstream of the reactive column to handle a substantial part of thereaction duty, which greatly enhances the RD technique.


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There is a large difference in the boiling points of alcohol (either methanol or ethanol) and theseed oils or their fatty acid esters involved in the transesterification reaction (table 1). During theoperation, most of the methanol would be in a vapor phase while the conversion to biodieselwould happen in a liquid phase.

Table1. Boiling points (at 1 atm) of chemical components involved during the transesterificationreaction (aGoodrum, 2002; bMerck Index, 9th ed.)

Component Bioling Point (C)

Rapeseed methyl ester 369.0a

Canola methyl ester 338.1a

Methanol 64.7b

Glycerol 290.0b

Figure 2 illustrates the general setup of RD technique applied to biodiesel preparation in a

trayed-column. The feed stream of oil and methanol/catalyst was introduced at the upper tray ofthe column and, combining with the condensed alcohol vapor, flows downward; while themethanol vapors from the reboiler flask rises upwards causing a counter-current gas-liquidcontact. Each tray in the column forms a reactive zone, or a mini-reactor. Each mini-reactorcontains alcohol which is much more concentrate than that in the feeding stream, forming a highalcohol to oil ratio and resulting in a more uniform and higher reaction rate.

Figure 2. Reactive distillation column operated counter-currently.

The ultimate goal of this research is to explore a technically and economically sound reactortechnology for biodiesel production, which applies the reactive distillation technique. Theobjectives of this study were to (1) construct a lab-scale continuous-flow reactive distillationprocess system, and (2) determine the effect of oil-to-alcohol ratio on the fatty ester yield bytargeting at a molar ratio close to the theoretical ratio of 3:1.

Product

Condenser

Reboiler

Feed Alcohol Vapors

Partially reacted

mixture


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Materials and Methods

The crude canola oil used in this research was obtained from the oil seed processing plant atthe Department of Biological and Agricultural Engineering of the University of Idaho. Analytical

grade methanol and potassium hydroxide were of obtained from J.T. Baker (Phillipsburg, NJ).GPO-trinder Reagent and reference standards such as triolien, diolien, methyl olieate andglycerol were purchased from Sigma-Aldrich Co. (St.Louis, MO).

Table 2. Fatty Acid Profile of Canola Oil used in this research

Fatty Acid Composition (% wt.)

Palmitic (16:0) 3.9

Stearic (18:0) 2.1

Oleic (18:1) 59.3

Linoleic (18:2) 18.4

Linolenic (18:3) 7.8

Eicosic (20:1) 2.1

Erucic (22:1) 4.4

Equipment and Experimental Setup

A laboratory-scale continuous-flow RD system (fig. 3) was developed and tested on overallprocess parameters. The central system component is a vacuum jacketed, Oldershawperforated plate distilling column (Chemglass, Vineland, NJ). This 10-plate column has an innerdiameter of 23 mm, a weir height of 4 mm, and a distance of 25 mm between plates.

Figure 3. Experimental setup of the laboratory-scale continuous-flow RD reactor system.


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Feed mixer/

Pre-reactor Decanter

Biodiesel

Glycerol

T1

T2

T3

T4

T5

Oil FeedMethanol &

KOH

RD

Column

Recycle Methanol

A short 3 ml in-line static mixer (Cole-Parmer, IL) was used as a feed mixer and a pre-reactorprior to the RD column. The lower end of the column was fitted to a 500 ml three-neck round-bottom flask was used as a reboiler. A water-cooled condenser was fitted to the top of thecolumn to recover alcohol, which is combined with reactants and pumped back into the column.The product mixture was withdrawn from the reboiler and send to the separation column.Biodiesel/glycerol separation was carried out by gravity in a continuous decanter (70300 mm)

with an adjustable feed-in point. The input and output streams of methanol/KOH solution, oil,and product mixture were handled simultaneously with three Masterflex peristaltic pumps (Cole-Parmer, IL) which were calibrated and adjusted to achieve the desired flow rates ranging from0.5ml/min to 8.0ml/min. Temperature monitoring and feedback controls were accomplished withFuji PXR3 and PXR4 PID/feedback controllers (distributed by TTI Inc., VT).

Experimental Procedures

Two sets of preliminary trials with and without a pre-reactor were conducted with the RD setupas shown in fig. 3. The main process parameters examined in this study were: oil-to-alcoholratio, flow rates, and reaction time and temperature. In preparation for each trial, stock alcoholicKOH was prepared on a stirring plate at a ratio that corresponded to 1% KOH w/w of oil for eachgiven methanol-to-oil molar ratio, and placed in a holding reservoir next to the RD column.Likewise canola oil was held in a separate heated reservoir maintained at 50C. Thesereactants were fed through separate calibrated peristaltic pumps into the pre-reactor or directlyinto the column where the reaction began. The methanol-to-oil molar ratios used were 3.0, 3.5,4.0 and 4.5. These various ratios were achieved by adjusting the alcohol/catalyst flow raterelative to the flow rate of the oil. For this column, residence (reaction) time can be related tooverall flow rate. Additionally a suitable flow rate had to be maintained to avoid operationalproblems such as column flooding and weeping. From several trials, it was found that an overallflow rate of 5-6 ml/min with the column temperature at 65C provided residence time of about 5min without any significant operational difficulties. The column temperature was maintained bycontrolling the reboiler heat input. Temperatures above 65C caused excessive entrainment and

a reduction in methanol concentrations in the liquid phase. Lower temperatures causedsignificant reduction in the methanol vapor flow which directly affected the ester conversion.Excess methanol vapors were condensed and recycled back to the column while the productmixture was continuously drawn from the bottom flask. It was separated into biodiesel andglycerol layer by the continuous gravity decanter with feed-point at the middle of the column.Temperatures were monitored and controlled at various strategic locations, as shown in fig. 4.

Figure 4. Schematic diagram of the RD reactor system


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Actual flow rates and temperature profiles used for each run, with varying methanol-to-oil ratio,were averaged and are shown in table 3.

Table 3. Process parameters used in different trials

Trials Molar Ratio 1Qoil1Qmethanol

2T1 2T2 2T3 2T4 2T5

1) With Pre-reactorRun 1 3.0:1 6.67 0.8 50 65 150 24.6 25.0Run 2 3.5:1 5.67 0.8 50 65 125 24.8 25.3Run 3 4.0:1 4.95 0.8 50 65 115 24.6 25.1Run 4 4.5:1 4.45 0.8 50 65 110 24.0 25.4

2) Without Pre-reactorRun 5 3.0:1 6.67 0.8 50 65 135 24.3 N/ARun 6 3.5:1 5.71 0.8 50 65 126 24.1 N/ARun 7 4.0:1 5.00 0.8 50 65 123 24.7 N/A

Run 8 4.5:1 4.45 0.8 50 65 95 24.0 N/A1Qoil & Qmethanol areOil flow rate and methanol-catalyst flow rate, respectively, in ml/min.2 T1, T2, T3, T4 & T5 are feed oil temperature, Column operating temperature, Reboiler temperature,column feed inlet temperature and pre-reactor feed inlet temperature, respectively, in degree Celsius.

Product Characterization

The product obtained from each run was analyzed for the contents of methyl esters, methanol,total glycerol, and the product viscosity and density. An HPLC (HP 1090 series) withChemStation software and an evaporative light scattering detector (Altech2000; Deerfield, IL)was used to analyze the total methyl esters. The column was a Luna 5 CN 100A, 2504.6mm

I.D (Phenomonex, Torrance, CA). The method, developed by Bruns (1989) was slightly modifiedfor our purposes. It is a linear gradient method with mobile phase steps: 99.8% iso-octane +0.2% 2-propanol initial 5 min hold up, 95% octane+5% 2-propanol in 15 min and held till 20 min,then finally 90% octane+10% 2-propanol in 30 min. Twenty milligram samples were diluted witha 10 ml solution of 96% octane+4% 2-propanol for a working sample dilution of 2mg/ml. Sampleinjection size was 20l and both temperatures of the column and detector drift tube were

maintained at 40C. Mobile phase flow rate was 1 ml/min and nebulizer gas flow rate was set at1.5 l/min.

The Greenhill method issued by National Biodiesel Accreditation Commission, BQP02(03),was used to measured total glycerol content in biodiesel samples. It is a spectroscopicdetermination and was set up as an alternative to ASTM D 6584, which is specified under the

standard specification for biodiesel fuel (ASTM D 6751).The specific gravity was measured using a 20-ml Bingham Pycnometer (Fischer Scientific, PA)

at 20C under the guidelines of ASTM method D 1217. Viscosity measurements were made at40C using a #100 Cannon-Fenske viscometer (Fischer Scientific, PA) set in a Koehler ModelK-23300 oil bath (Koehler, Bohemia, NY). The methanol content in biodiesel samples was

determined by the difference of a sample before and after heating to 70C for 30 min to drive offthe alcohol.


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Results and Discussions

The process sensitive characteristics, such as total methyl esters, total glycerin, methanol, andviscosity, of samples obtained under different experimental runs were cited in table 4.

Table 4. The effect of methanol-to-oil ratio on the product parameters.

TrialsMolarRatio

Methyl esters(%wt)

Total Glycerol(% wt)

Methanol(%wt)

Viscosity(cst)

Specificgravity

1) With Pre-reactorRun 1 3.0:1 76.5 0.26 1.99 6.18 0.85Run 2 3.5:1 84.0 0.33 1.38 5.01 0.85

Run 3 4.0:1 91.7 0.15 0.90 4.63 0.82Run 4 4.5:1 93.2 0.30 1.51 4.23 0.87

2) Without Pre-reactorRun 5 3.0:1 66.2 0.11 3.74 8.44 0.82Run 6 3.5:1 79.5 0.19 2.19 6.32 0.83Run 7 4.0:1 83.3 0.18 1.98 5.96 0.81

Run 8 4.5:1 85.9 0.28 4.84 5.50 0.82

As expected, the setup with a pre-reactor gave better reaction yield compared to correspondingruns without a pre-reactor. The methyl ester content increase with molar ratio justifies the needfor excess alcohol to drive the reaction to a higher yield (fig. 5). Since, the reaction rates arequite high at the beginning, a major part of the reaction conversion can be achieved in the in-line static mixer. The use of a pre-reactor also reduces the size of reactive zone and ultimately

the size of the column and the cost of production.

Figure 5. Effect of methanol-to-oil ratio on methyl esters content in product.

Methyl Esters Content

50

60

70

80

90

100

3 3.5 4 4.5 5Methanol-to-Oil ratio

M

ethylEsters(%wt

without pre-reactor with pre-reactor


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A significant amount (approx. 10%) of unreacted methanol flowed out of the column with theproducts. About 30% of this methanol ended up in the biodiesel layer while the remainder wasfound in the glycerol layer. Figure 6 shows the trend followed by methanol content in thebiodiesel layer. Biodiesel obtained without the pre-reactor had higher methanol content. Thiswas most likely due to incomplete reaction due to less residence time. At a 4:1 molar ratio,methanol content in the product was found to be the lowest for both experimental setups under

the tested conditions. The methanol content rose if the ratio was increased to 4.5:1 due to agreater excess of methanol and its incomplete vaporization from the reboiler.

Methanol Content

0

1

2

3

4

5

6

3 3.5 4 4.5 5

Methanol-to-Oil ratio

Methanol(%wt

without pre-reator with pre-reactor

Figure 6. Effect of methanol-to-oil ratio on methanol content in product.

There is a correlation between the viscosity and the amount of unreacted glycerides present inthe biodiesel. It can be seen in table 3 that as the molar ratio increased, the percent esterincreased while the unreacted glycerides correspondingly decreased. This is reflected in fig. 7

whcih illustrates a decrease in viscosity with a higher molar ratio. Additionally, samples obtainedwith the pre-reactor setup have higher ester percentages and hence lower viscosity ascompared to corresponding runs without the pre-reactor.

Viscosity Profile

3

5

7

9

3 3.5 4 4.5 5Methanol-to-Oil ratio

KinematicViscosity@4

0C

cst

with pre-reactor without pre-reactor

Figure 7. Effect of methanol-to-oil ratio on product viscosity.


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SummaryThe reactive distillation process as it was set up and described in this paper, has been found tobe feasible for the continuous production of biodiesel from seed oils. The original objective to

make the process more efficient by reducing the alcohol-to-oil molar ratio was realized. A 66%reduction to the industrial standard of 6:1 was achieved with good results. From the datacollected it can be concluded that the operating the RD system at 65C with a 4:1 molar ratioand with a pre-reactor was near the optimum point for producing biodiesel from among theparameters examined in this study. The biodiesel obtained under these conditions met thenational standards (ASTM D 6751) for total glycerol and viscosity. Testing with this system willcontinue to in an attempt to reduce the energy and material inputs to improve the efficiencyfurther while maintaining fuel quality.

Acknowledgments

This study was financially supported by the National Institute of Advanced TransportationTechnology (NIATT) of the University of Idaho, and Idaho Rapeseed/Canola Commission. Theauthors would express appreciation to Andrej Paszczynski and David Christian for theirassistance in the development of HPLC method for biodiesel product analysis.

References

Allen, H.D., G. Rock, and A. Kline. 1945. Process for treating fats and fatty oils. U.S. Patent No.2383579.

Antolin, G., F.V. Tinaut, Y. Briceno, V. Castano, C. Perez, and A.I. Ramirez. 2002. Optimisationof biodiesel production by sunflower oil transesterification, Bioresource Technology. 83:111114

Bruns, A., H. Waldhoff, and W. Winkle. 1989. Applications of HPLC with evaporative lightscattering detection in fat and carbohydrate chemistry. Chromatographia27(7/8):340-343.

Canakci, M., and Jon VanGerpen. 2000. The Effect of Yellow Grease Methyl Ester on EnginePerformance and Emisssions. Final Report: Recycling and Reuse Technology TransferCenter. Publication #2000-134.

Darnoko, D., and Munir Cheryan. 2000. Kinetics of Palm Oil transesterification in a batchreactor, JAOCS 77(12):1263-1267.

Freedman, B., E.H. Pryde, and T.L. Mounts. 1984. Variable affecting the yields of fatty estersfrom transesterified vegetable oils. JAOCS61:1638-1643.

Freedman, B., R.O. Butterfield, and E.H. Pryde. 1986. Transesterification kinetics of soybeanoil. JAOCS:63:1375-1380.

Goodrum, J.W. 2002. Volatility and boiling points of biodiesel from vegetable oils and tallow.Biomass and Bioenergy 22:205 211.

Jackson, M.A. and J.W. King. 1985. Methanolysis of seed oil in flowing supercritical carbondioxide. JAOCS61:1009-1013.


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Ma. F., and M.A. Hanna. 1999. Biodiesel production: a review. Bioresource Technology70:1-15.

Ma. F., L.D. Clements, and M.A. Hanna. 1998a. The effects of catalyst, free fatty acids andwater on transesterification of beef tallow. Trans. ASAE41:1261-1264.

NBAC Designationation: BQP-02 (03). Standard Test Method for Free and Total Glycerol inBiodiesel (Greenhill Method).

Noureddini, H., D. Harkey, and V. Medikonduru. 1998. Continuous process for the conversionof vegetable oils into methyl esters of fatty acids. J. Am. Oil Chem. Soc. 75(12):1775-1783.

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Trent, W. R. 1945. Process of treating fatty glycerides. U.S. Patent No. 2383632.

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Reactor Pt Proces Continuu Biodiesel