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Phosgene-Free Dimethyl Carbonate Production University of Pennsylvania ScholarlyCommons Department of Chemical & Biomolecular Senior Design Reports (CBE) Engineering 4-14-2009 PHOSGENE-FREE DIMETHYL CARBONATE PRODUCTION Alex Fick University of Pennsylvania Dong Lin University of Pennsylvania Rob Vavra University of Pennsylvania Follow this and additional works at: https://repository.upenn.edu/cbe_sdr Part of the Chemical Engineering Commons Fick, Alex; Lin, Dong; and Vavra, Rob, "PHOSGENE-FREE DIMETHYL CARBONATE PRODUCTION" (2009). Senior Design Reports (CBE). 6. https://repository.upenn.edu/cbe_sdr/6 This paper is posted at ScholarlyCommons. https://repository.upenn.edu/cbe_sdr/6 For more information, please contact [email protected]. PHOSGENE-FREE DIMETHYL CARBONATE PRODUCTION Abstract A novel, phosgene-free approach to producing 100 MMlb/yr of dimethyl carbonate (DMC) was designed using a two step catalytic reaction of methanol and urea to produce DMC and ammonia. The methanol and urea were mixed and heated to drive the first step of the eaction,r conversion of urea to methyl carbamate (MC). The MC and methanol mixture was fed to a high pressure reactive distillation column containing the catalyst. The reactive distillation tower strips off ammonia as it is produced, forcing the reaction forward. The ammonia vapor is then sold to an adjacent plant, which uses it to produce urea. The components of the liquid stream leaving the reactive distillation tower are separated by simple distillation towers. Excess methanol and MC are recycled back to the reactive distillation tower, leaving only the purified ammonia and DMC streams as products. Several assumptions are made in the design of this process. First, due to the lack of readily-available data or binary coefficients, the interactions of DMC and MC in a vapor-liquid equilibrium environment are estimated using ASPEN Plus. Second, the exact yield of DMC is unknown under the process conditions, though the reactive distillation tower was designed in conjunction with the chosen catalyst in such a way as to guarantee a good, predictable lower bound on the production of DMC. Finally, due to the nature in which urea is mixed with methanol at high temperature and pressure, an entirely custom solids handling system is necessary to adequately mix and react the urea and methanol. As the full details of this system are not known, the design uses an approximation of the equipment and utilities required. Based on these assumptions, the design gives a DMC production scheme that is reliable, economically feasible, and environmentally neutral. Disciplines Chemical Engineering This article is available at ScholarlyCommons: https://repository.upenn.edu/cbe_sdr/6 Phosgene-Free Dimethyl Carbonate Production Fick, Lin, Vavra PHOSGENE-FREE DIMETHYL CARBONATE PRODUCTION Alex Fick Dong Lin Rob Vavra Senior Design Report Spring 2009 Department of Chemical and Biomolecular Engineering University of Pennsylvania Faculty Advisor: Dr. Wen Shieh, University of Pennsylvania Recommended by: Mr. Bruce Vrana, DuPont Engineering Technologies Phosgene-Free Dimethyl Carbonate Production Fick, Lin, Vavra Phosgene-Free Dimethyl Carbonate Production Fick, Lin, Vavra Letter of Transmittal April 7, 2009 Department of Chemical & Biomolecular Engineering University of Pennsylvania 220 South 33rd Street Philadelphia, PA 19104 Dear Professors Shieh and Fabiano, As per our senior design problem statement, we have successfully completed our analysis of a new phosgene-free route to produce dimethyl carbonate from urea and methanol. We believe that we have created a both technically and economically feasible design, after evaluating many design alternatives. Enclosed you will find our design to produce 100 million pounds of dimethyl carbonate per year. At a dimethyl carbonate price of $0.40, the plant as designed has a net present value of $50.7 million and an internal rate of return of 35.7%. Based upon these measures, we conclude that the project is both economically feasible and environmentally neutral. We recommend that the project proceeds as designed. Sincerely, ______________________ ____________________ ______________________ Alex Fick Dong Lin Rob Vavra Phosgene-Free Dimethyl Carbonate Production Fick, Lin, Vavra Table of Contents Abstract .................................................................................................... 1 Section 1—Introduction ........................................................................... 3 Section 2—Process Flow Diagram, Block Diagram, and Process Description ............................................................................................... 9 Section 3 – Utilities ................................................................................ 17 Section 4 – Unit Descriptions................................................................. 21 Section 5 – Specification Sheets ............................................................ 33 Section 6 – Equipment Costs and Capital Investment ........................... 51 Section 7 – Other Considerations ........................................................... 57 Section 8 – Operating Cost and Economic Analysis .............................. 61 Section 9 – Conclusions and Recommendations .................................... 71 Acknowledgements ................................................................................ 75 Bibliography ........................................................................................... 76 Appendix A – Problem Statement .......................................................... 79 Appendix B – Detailed Design Calculations .......................................... 83 Appendix C – Predicting the Properties of DMC and MC in Aspen Plus .............................................................................................................. 117 Appendix D – Profitability Analysis Worksheet .................................. 119 Appendix E – Patents ........................................................................... 149 Appendix F – Material Safety Data Sheets .......................................... 157 Phosgene-Free Dimethyl Carbonate Production Fick, Lin, Vavra Phosgene-Free Dimethyl Carbonate Production Fick, Lin, Vavra Abstract A novel, phosgene-free approach to producing 100 MMlb/yr of dimethyl carbonate (DMC) was designed using a two step catalytic reaction of methanol and urea to produce DMC and ammonia. The methanol and urea were mixed and heated to drive the first step of the reaction, conversion of urea to methyl carbamate (MC). The MC and methanol mixture was fed to a high pressure reactive distillation column containing the catalyst. The reactive distillation tower strips off ammonia as it is produced, forcing the reaction forward. The ammonia vapor is then sold to an adjacent plant, which uses it to produce urea. The components of the liquid stream leaving the reactive distillation tower are separated by simple distillation towers. Excess methanol and MC are recycled back to the reactive distillation tower, leaving only the purified ammonia and DMC streams as products. Several assumptions are made in the design of this process. First, due to the lack of readily-available data or binary coefficients, the interactions of DMC and MC in a vapor-liquid equilibrium environment are estimated using ASPEN Plus. Second, the exact yield of DMC is unknown under the process conditions, though the reactive distillation tower was designed in conjunction with the chosen catalyst in such a way as to guarantee a good, predictable lower bound on the production of DMC. Finally, due to the nature in which urea is mixed with methanol at high temperature and pressure, an entirely custom solids handling system is necessary to adequately mix and react the urea and methanol. As the full details of this system are not known, the design uses an approximation of the equipment and utilities required. Based on these assumptions, the design gives a DMC production scheme that is reliable, economically feasible, and environmentally neutral. 1 Phosgene-Free Dimethyl Carbonate Production Fick, Lin, Vavra 2 Phosgene-Free Dimethyl Carbonate Production Fick, Lin, Vavra Section 1—Introduction 3 Phosgene-Free Dimethyl Carbonate Production Fick, Lin, Vavra The purpose of this project is to design a chemical process which employs a new phosgene-free reaction to produce 100 million pounds of dimethyl carbonate (DMC). DMC is an industrial chemical with many uses. It is primarily produced and polymerized to form polycarbonates, which are a type of plastics known for their optical transparency, impact resistance, and high dielectric strength. For example, polycarbonates are found in DVD and Blu- ray discs, safety goggles, eyeglass lenses, bullet-resistant windows, electrical insulators, aircraft, and missile components. This abundance and variety of applications generates substantial demand for DMC and makes production a viable investment. This project aims to design a practical process to create DMC without the use of phosgene. Although most of the current DMC production employs phosgene, there are significant disadvantages to doing so. Phosgene is a highly toxic chemical that can cause death or severe health issues in even low concentrations, meaning that any process design incorporating phosgene will incur extra costs to ensure a safe environment. Current DMC production schemes using phosgene also create sodium chloride as a byproduct. Disposal of this sodium chloride can cause environmental damage, especially
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