Finall PP Oral Presentation SrDesign

Process Design and Technoeconomic Analysis for the

Downstream Recovery and Purification of Diethyl Malonate

Team 7Chris Bilham

Brian CoventryMark Kelsic

Yekaterina PokhilchukDan Sriratanasathavorn

Matthew Lipscomb, PhD.CEO & Founder

DMC Limited

❖ Agenda

• Introduction• Project Goals• Purification Method 1 • Purification Method 2• Environmental• Economics• Conclusions• Acknowledgements

diethyl malonate

Image from: http://www.sigmaaldrich.com/catalog/product/aldrich/d97754?lang=en&region=US

http://www.directindustry.com/prod/solaris-biotechnology/product-54387-443440.html https://en.wikipedia.org/wiki/Malonic_acidhttp://culmotrialattorneys.com/bpa-may-alter-gene-regulation/ https://en.wikipedia.org/wiki/Continuous_stirred-tank_reactor

Uses● pharmaceuticals● fragrances● dyes● adhesives

❖ Diethyl Malonate (DEM)

❖ Project Goal Statement

Two methods for purification of diethyl malonate (DEM) from a fermentation reactor are to be designed and economically analyzed.

Deliverables● Economical, environmental, and safety analysis

DEM production specifications● 10,000,000 kg/year● >99% purity

Image from: http://www.sigmaaldrich.com/catalog/product/aldrich/d97754?lang=en&region=US

❖ Experimental Data and Solvent Selection

Models:● Decanter● LLE & distillation

Solvent Selection:● Separation factor● Boiling point● Cost

Solvent of choice - Pentane

K = 2.64 (DEM in petane-water solution)

❖ Method 1 - Decant

Assumptions:● No salts entrain with the water to the

evaporator● No salts entrain with the DEM product● All salts leave with waste stream

❖ Method 1 - Decant

❖ Method 2 - Liquid-Liquid Extraction (LLE)

Assumptions:● Salts do not enter pentane phase● Water does not enter pentane phase● Pentane does not enter water phase

❖ Method 2 - Liquid-Liquid Extraction (LLE)

❖ Series Process - Decanting followed by LLE

❖ Environmental and Safety

Hazardous Waste● Listed by the EPA● Ignitability● Corrosivity● Reactivity● Toxicity

Safety ● 12 M HCl is extremely corrosive ● 1 M NaOH

Image from: http://rapidwasteenviro.com/wp-content/uploads/2014/12/hazardous-waste-types.png

❖ Wastewater

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Industrial Wastewater for Boulder● Permit $7,050 per year ● Publicly owned treatment works

(POTW)● Specific pollutant limitation● pH 5.5- 10● $70 per 1000 gallons

❖ Operating expense sensitivity analysis parameters

Parameters that were investigated:

● Feed DEM production price● Feed stream DEM %● LLE column stages● LLE column solvent to feed ratio● Decanter pH● Decanter temperature

Note: The following slides to not take into account waste disposal fees which did not vary during sensitivity analysis

❖ Sensitivity to feed composition and price

• Series Process is cheapest at every condition

• Solid line shows low DEM production price ($1.90/kg)

• Dotted line shows high DEM production price ($3.10/kg)

❖ Operating cost breakdown

Series Process Only LLE Only Decant

99.95% DEM recovery 99.96% DEM recovery 94.76% DEM recovery

• Distillation represents the biggest operational expense

• DEM sent to waste considered an operational expense

❖ Liquid-Liquid Extraction sensitivity

• Careful balance between losing DEM and distillation costs

• Increasing LLE stages lowers operating costs but increases capital costs

• Series Process most economical at 99.1% recovery in LLE unit

Increasing DEM recovery

Increasing distillation costs

Series Process

❖ Decanter sensitivity

• Most economical to not change temperature of feed

• Decreasing pH lowers DEM solubility in water

• Process economics may continue to improve at lower pH

Series Process

❖ Effect of wastewater treatment

• Boulder has very expensive wastewater prices

• Wastewater increases the unit operating cost by a constant amount for each process

Series Process Only LLE Only Decant

+$0.11/kg+$0.11/kg +$0.14/kg

❖ Economics

• Lowest initial capital investment is for LLE only process.

• Lowest operational cost is for the Series process

Adding in capital costs for equipment and installation...

❖ Economics

• Fastest return on investment is always the LLE only, when considering all associated costs.

❖ Conclusion

• Decanting alone is a poor choice.

• Series and LLE have similar operational costs

• Our model suggests that LLE is the best option including all costs.

• Plant should be considered somewhere with lower waste disposal costs.

• Capital costs should be further investigated to determine tradeoff of long term operation against initial investment

• Further investigation into salting and pH effects on the solubility of DEM is warranted.

❖ Acknowledgements

● Professor Thomas Belval - University of Colorado Boulder● Dr. Mathew Lipscomb - DMC Limited● Professor Rainer Volkamer - CU● Dr. Molly Larsen - CU● Zachary Finewax - CU● Theodore Koenig - CU

❖ ReferencesBMU (Bundesministerium für Umwelt, Naturschutz und Reaktorsicherheit),. (2016). Malonic Acid Diesters. Paris, France:

SIAM. Retrieved from http://www.inchem.org/documents/sids/sids/malonates.pdfCharacteristics of Hazardous Waste (CHW)) Subpart C- 261.32 (Hazardous wastes from specific sources.) .2012

https://www.gpo.gov/fdsys/pkg/CFR-2012-title40-vol27/xml/CFR-2012-title40-vol27-part261.xml#seqnum261.21Dietrich, J., Fortman, J., & Steen, E. (2016). Recombinant host cells for the production of malonate. US.Henley, E. J., Seader, J. D., & Roper, D. K. (2011). Separation process principles. Hoboken, NJ: Wiley.Hernandez, M., & Abu-Dalo, M. (2016). Removing metals from solution using metal binding compounds and sorbents therefor.

US.Lyons, J., White, C. W., & Loh, H. P. (2002). Process Equipment Cost Estimation Final Report (Rep.). NETL.National Center for Biotechnology Information (NCBI). PubChem Compound Database; CID=6097028,

https://pubchem.ncbi.nlm.nih.gov/compound/6097028 (March 21, 2006).National Center for Biotechnology Information (NCBI 2). PubChem Compound Database; CID=24450,






https://pubchem.ncbi.nlm.nih.gov/compound/5284359 (March 15, 2006).Product and Process Design Principles: Synthesis, Analysis and Design. (2009). S.l.: John Wiley and Sons.Protection of Environment. Code of Federal Regulations (CoFR), Title 40 - (n.d.). 2012, from

https://www.gpo.gov/fdsys/pkg/CFR-2012-title40-vol27/xml/CFR-2012-title40-vol27-part261.xml#seqnum261.21

http://www.inchem.org/documents/sids/sids/malonates.pdf

http://www.inchem.org/documents/sids/sids/malonates.pdf





❖ ReferencesSusan E. Bailey, Trudy J. Olin, R.Mark Bricka, D.Dean Adrian, A review of potentially low-cost sorbents for heavy metals,

Water Research, Volume 33, Issue 11, August 1999, Pages 2469-2479, ISSN 0043-1354, http://dx.doi.org/10.1016/S0043-1354(98)00475-8.

(http://www.sciencedirect.com/science/article/pii/S0043135498004758)Yaws, Carl L.. (2012). Yaws' Handbook of Properties for Aqueous Systems. Knovel. Online version available at:

http://app.knovel.com/hotlink/toc/id:kpYHPAS006/yaws-handbook-properties/yaws-handbook-propertiesZeppieri, S., Rodriguez, J., & Lopez de Ramos, A. L. (2001). Interfacial Tension of Alkane and Water Systems. J. Chem. Eng.

Data, 1086-1088. Retrieved April/May, 2016, from http://pubs.acs.org/doi/pdf/10.1021/je000245r

http://www.sciencedirect.com/science/article/pii/S0043135498004758

http://app.knovel.com/hotlink/toc/id:kpYHPAS006/yaws-handbook-properties/yaws-handbook-properties

http://app.knovel.com/hotlink/toc/id:kpYHPAS006/yaws-handbook-properties/yaws-handbook-properties

http://pubs.acs.org/doi/pdf/10.1021/je000245r

http://pubs.acs.org/doi/pdf/10.1021/je000245r

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