Finall PP Oral Presentation SrDesign

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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

❖ 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

Finall PP Oral Presentation SrDesign

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