Wilmington, DE, United States

Compact Membrane Systems, Inc.

www.compactmembrane.com
Wilmington, DE, United States
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Patent
Compact Membrane Systems, Inc. | Date: 2016-03-23

A highly fluorinated polymer is very useful as an acid catalyst. The highly fluorinated polymer has at least two repeating unit types that are the polymerized derivatives of a perfluorinated cyclic or cyclizable compound and a highly fluorinated vinyl ether compound having a sulfur containing functional group. The polymer can be formed by radical copolymerization of the fluorinated monomers with the sulfur-containing functional group in sulfonyl fluoride form (SO_(2)F) that is subsequently converted to sulfonic acid form (SO_(3)H). The highly fluorinated polymer can be used to advantage in a solution comprising an aprotic, polar organic solvent that has a dielectric constant of at least 15 and preferably is free of hydroxyl functional groups. Suitable solvents are those in which the polymer is soluble to at least 1 wt %. Hydroxyl group-containing protic, polar organic solvents are less preferred. The highly fluorinated polymer can be an effective heterogeneous catalysts when used in form of solid, fine particles insolubly suspended in or in contact with a fluid reaction mass.


Grant
Agency: Department of Health and Human Services | Branch: National Institutes of Health | Program: SBIR | Phase: Phase II | Award Amount: 859.47K | Year: 2016

DESCRIPTION provided by applicant In the manufacture of pharmaceutical compounds organic syntheses are often carried out in organic solvents These solvents must then be separated from high value intermediates and active pharmaceutical ingredients APIs in order to produce the final product medications Many intermediate compounds and APIs are thermally labile and thermal separation processes such as distillation thermal evaporation are not preferred In addition distillation and evaporation processes are energy intensive making them costly to operate Nanofiltration NF is a superior alternative to phase change based separation processes such as distillation and evaporation In contrast to phase change separations nanofiltration is a molecular level size sieving based separation process and can be operated at ambient or sub ambient temperatures In NF driven by the applied pressure gradient low molecular weight compounds such as solvents permeate through the nanofiltration membrane while higher molecular weight compounds are retained Although nanofiltration technology for aqueous systems is well established the technology for organic solvent nanofiltration OSN systems is still under development There are very few examples of pilot and industrial scale applications of OSN in the pharmaceutical industry The primary limitation of OSN in API purification is low product yield due to loss of the product through the membrane Stated another way the high loss of product hinders the widespread application of membranes in the pharmaceutical industry and solvent resistant OSN membranes that are more selective and or more selective solvent resistant OSN membrane processes are needed The broad objective for the phase II program is to develop nanofiltration membrane processes that provide clear economic advantages over distillation and evaporation processes for separating solvents from APIs with the molecular weights in the range of to g mol Compact Membrane Systems will develop OSN membrane technology with superior membrane performance solvent flux and solute rejection and superior membrane stability in pharmaceutical solvent systems compared to currently commercial OSN membranes These membranes will be the key component of OSN systems that can be used as stand alone unit operations or combined with other unit operations for the separation of solvents from intermediates and APIs in commercial pharmaceutical manufacturing processes In addition to solvent API separation these OSN membranes may be useful in solvent exchange genotoxic impurity separation crystallization and chemical synthesis operations PUBLIC HEALTH RELEVANCE Compact Membrane Systems will develop membrane technology with superior performance and stability for the pharmaceutical industry These membranes will lower the cost of separation of solvents from intermediates and active pharmaceutical ingredients in commercial manufacturing processes


Grant
Agency: Department of Energy | Branch: | Program: SBIR | Phase: Phase I | Award Amount: 150.00K | Year: 2015

Currently there is great interest in the development of renewable fuels, such as biodiesel. Algae is one source of oil feedstock for biodiesel production that has been extensively investigated in recent years. Unlike vegetable oil crops, such as soybeans, algae grows very fast, can be grown on land of limited agricultural value, and can be grown in seawater or wastewater which are not suitable for agricultural crops. Despite the many advantages algae offers over more conventional oil feedstock crops, algae sourced biodiesel has not developed into a commercial process due to its high operating costs. One of the steps in the process that has a high operating cost is the dewatering step. Development of a membrane filter that will reduce the cost of the dewatering step is the focus of this proposal. This program develops a new low-cost fouling resistant composite filtration membrane that is not currently available commercially. The nonstick perflouoropolymer layer is combined to the porous filtration membrane in a manner that does not blind the pores or significantly reduce the water transport rate across the membrane, while simultaneously dramatically improving the fouling and chemical resistance of the membrane. During the Phase I project, Compact Membrane Systems will identify the proper membrane support pore size for algae slurry concentration, develop a method to coat the support with the polymeric membrane, design a lab scale concentration system, run the system for a prolonged period of time, and obtain data for flow and water removal rates. The cost of harvesting along with the other major cost components must be substantially reduced in order to make algae oil a viable source of biodiesel fuel. Introduction of a durable fouling resistant filtration membrane will substantially reduce the cost of dewatering, thereby substantially reducing the cost of the harvesting process. The current biodiesel market in United Sates is approximately 1,400 million gallons/year. Assuming conservatively that 10% of the total biodiesel market will be served by algae oil processed by this technology, the anticipated market for algae oil processing in United States is 140 million gallons/year. Based on cost savings of $0.40/gallon from the proposed membrane, the total annual cost savings for processing algae oil in the U.S. is estimated as 56 million dollars.


Grant
Agency: Department of Energy | Branch: | Program: SBIR | Phase: Phase I | Award Amount: 150.00K | Year: 2015

Fossil fuels currently supply more than 85% of the worlds energy needs and combustion of these fuels is the source of 80% of all anthropogenic emissions of carbon dioxide. Carbon dioxide is a greenhouse gas and is considered to be a major contributor to global warming. There is considerable interest in capturing carbon dioxide at large sources, electric power plants, and sequestering the gas. However, application of the existing technologies for carbon dioxide capture would significantly increase the cost of electric power generation.This program combines two novel technologies, the amorphous perfluoropolymer membrane gas/liquid contactor and ionic liquid absorbents, to create a novel system for a selectively separating carbon dioxide from flue gas and concentrating it for sequestration. The proposed system will be capable of capturing greater than 90% of the carbon dioxide emissions at electric power plants at a cost of less than $40 per tonne, substantially less than the currently available technologies. Earlier work has demonstrated the feasibility of capturing 90% of the carbon dioxide in a simulated flue gas stream. This program will focus on increasing the efficiency of the membrane contactor by improving the contactor design and selection of an ionic liquid absorbent with superior properties. Parallel CMS data suggests excellent fouling resistance. In Phase I we will first evaluate candidate Ionic Liquids and then test compatibility with our membrane system. Using the best Ionic Liquid CMS membrane candidate based on sorption capacity, complexity, stability, viscosity, CO2 diffusivity, and compatibility) we will customize system design followed by measuring sorption and desorption rates. Finally, using this above data we will conduct an engineering and economic evaluation to see if we project meeting our target. $30/ton with 90% carbon dioxide capture). While the focus of this program is on capturing carbon dioxide at electric power plants, many other applications can be considered. This is a platform technology for removing carbon dioxide gas from other gases. Two significant applications of interest are: separation of carbon dioxide from natural gas and upgrading of landfill gas.


Grant
Agency: Department of Energy | Branch: | Program: SBIR | Phase: Phase II | Award Amount: 998.25K | Year: 2014

Industrial hydrogen production relies primarily on natural gas and hydrocarbon feedstocks to drive the various reaction chemistries that lead to hydrogen generation. Carbon dioxide, the ultimate co- product when such feedstocks and processes are employed, necessarily becomes a major contaminant of the generated hydrogen. Thus, carbon dioxide isolation and removal is an important process step in the efficient, low cost purification and recovery of hydrogen from the intermediate reformed and synthesis gases. A new proprietary, chemically resistant and highly durable membrane being developed in this project will improve the separation efficiency and dramatically reduce energy requirements for the separation of carbon dioxide and hydrogen. In the Phase I program, membranes with CO2/H2 selectivities as high as 15 were developed. When compared to both amine scrubbers and pressure swing absorption processes, the CMS membrane process has dramatically lower capital and operating costs. Costs for a typical CMS membrane system is $58/MM SCF H2 while PSA and amine scrubber costs are between $162 and $1,072 MM SCF H2 for the same 99% H2 purity. In the Phase II program CO2/H2 selectivities up to 40 have been achieved. While membranes with more than adequate selectivity have been demonstrated, there is still significant room for improvement in CO2 permeance. This program will develop a high performance (both high selectivity and high permeance), robust membrane for the purification of hydrogen. The proposed membrane will employ a novel material with a high permeability for CO2. While this material can easily be formed into a membrane, making the material thin enough to provide high CO2 permeance is much more difficult. CMS has identified a means of forming this material into a thin, high permeance membrane. This membrane fabrication method will be developed to enable fabrication of prototype membranes for pilot tests. Besides the hydrogen generation processes mentioned already, the new membrane promises to have broad application in the hydrogen economy, hydrogen processing, synthesis gas production, hydrotreating, and sulfur removal processes. Improvements in hydrogen purification and separation efficiencies and the ready isolation of a concentrated carbon dioxide co-product will have direct benefits in emissions reductions, energy independence, and carbon management.


Grant
Agency: Department of Agriculture | Branch: | Program: SBIR | Phase: Phase I | Award Amount: 100.00K | Year: 2015

The current dependence of the United States on foreign oil has sparked enormous interest in the use of biofuels, specifically cellulosic biofuels. Cellulosic biofuels are a carbon neutral, renewable resource, and their use could drastically curtail total carbon dioxide emissions while also reducing U.S. dependence on foreign oil. Worldwide biomass energy resources are estimated at 2 x 1021 J per year; this compares to the total worldwide energy reserve of about 2 x 1022 J stored in crude oil. Therefore, biomass grown over the course of a decade sequesters the energetic equivalent to the entire worldwide reserve of crude oil and represents an enormous reserve of energy that has yet to be significantly tapped. In addition, the United States itself has large reserves of cellulosic biomass, and it presents a potential route to energy independence.Compact Membrane Systems (CMS) has identified a potential attractive alternative pretreatment process. Pretreatment costs are typically very high. CMS proposes to enhance Ionic Liquid pretreatment process. Key to success of the CMS innovative Ionic Liquid (IL) pretreatment process is very high recovery of IL. CMS has identified and provided preliminary data for successful membrane recovery of IL at potentially low cost.In Phase I CMS will both demonstrate the pretreatment process and also using novel membrane process the needed recovery of key IL starting materials. Using basic data from these tasks we will quantify cost savings of CMS process. Target costs are being less than 70% of best available biomass pretreatment.


Grant
Agency: Department of Energy | Branch: | Program: SBIR | Phase: Phase II | Award Amount: 1.01M | Year: 2016

Ethylene and propylene are major chemical industry raw materials and consume a great deal of energy related to their production. It is estimated that 250 trillion BTU/yr are consumed in olefin/paraffin separations. In 2011 worldwide ethylene and propylene production was about 140 and 70 million tons respectively. Historically, membrane processes for separating olefins and paraffins have been demonstrated with somewhat encouraging results but stability problems have led to systems that have been unable to maintain performance. In many cases the use of silver (Ag+) salts were used to preferentially transport the ethylene or propylene.


Grant
Agency: Department of Agriculture | Branch: | Program: SBIR | Phase: Phase II | Award Amount: 600.00K | Year: 2016

The current dependence of the United States on fossil fuels has sparked enormous interest in the development of biomaterials derived from biomass, specifically cellulosic biomaterials. Cellulosic biomaterials are a carbon neutral, renewable resource, and their use could drastically curtail total carbon dioxide emissions while also reducing U.S. dependence on fossil fuels. Biofuels is one example of biomaterials that can be derived from biomass. Worldwide biomass energy resources are estimated at 2 x 1021 J per year; this compares to the total worldwide energy reserve of about 2 x 1022 J stored in crude oil. Therefore, biomass grown over the course of a decade sequesters the energetic equivalent to the entire worldwide reserve of crude oil and represents an enormous reserve of energy that has yet to be significantly tapped. In addition, the United States itself has large reserves of cellulosic biomass, and it presents a potential route to energy independence.The Joint BioEnergy Institute (JBEI) has identified a potentially attractive cellulose pretreatment process. Key to success of the CMS innovative pretreatment process is very high recovery of key starting materials. CMS has identified and provided preliminary data for successful membrane recovery of key starting materials. In Phase I CMS and JBEI demonstrated the pretreatment process and a novel membrane process for recovering the valuablekey starting materials. Using the basic datawe have quantified cost savings of CMS process being more than 60% relative to alternative process.CMS has put together a strong team of experts to demonstrate the CMS process. In Phase II we will scale up and optimize the CMS system and build a pilot test system to demonstrate the concept at larger scale. Using the pilot scale data we will conduct an engineering and economic analysis to highlight the economic advantage of the proposed concept vs. conventional technologies. This research and development project, if successful, will not only lead to a non-fossil fuel source of less-costly bio-fuels, but will also provide apractical routeto high value bio-chemicals. We expect alarge commercialization potential with this project.


Grant
Agency: Department of Energy | Branch: | Program: SBIR | Phase: Phase I | Award Amount: 150.00K | Year: 2016

Oxygen enriched air (OEA) is a valuable tool to enhance combustion processes and improve the energy efficiency. OEA reduces the presence of parasitic nitrogen and therefore flame temperature and associated heat transfer is higher with OEA. A membrane process is the most energy efficient way to make low end OEA (25-35%). Studies show that using 35% OEA reduces fuel consumption and CO2 generation by upwards of 60%. The resulting exhaust stream is dramatically more concentrated in CO2 which enhances CO2 sequestering. Often, cryogenic oxygen is diluted with air to provide target OEA level for combustion process. The use of 99+% oxygen mixed with air is thermodynamically inefficient. Traditionally membrane systems are more superior in small to intermediate size applications. Therefore, our initial focus will be combustion sites (e.g. furnaces) where demand for oxygen beyond 21% oxygen (e.g. air) is 5-20 tons/day. The program hypothesis is to successfully develop high selectivity oxygen/nitrogen separation membranes using high flux, chemically and thermally resistant amorphous fluorinated polymer membranes as the base matrix. Based on our unique fluoropolymer synthesis technique, CMS proposes to develop a group of fluorinated polymeric membranes which have high gas permeance and selectivity. The proposed membrane can produce OEA at a much lower cost than conventional oxygen/nitrogen separation membranes. This program develops a novel membrane which produces low cost oxygen enriched air. This program will 1) reduce energy requirements for small or medium size furnaces by up to 60% and 2) provide high CO2 concentration exhaust streams for enhanced concentrating of CO2 for CO2 sequestering. Commercial Application and Other Benefits: Oxygen is one of the top five chemicals used domestically. Small to medium size furnaces, which represent approximately 40% of the nation’s furnaces, consume less than 5 tons/day of oxygen. These 5 tons small to medium size furnaces would be ideal for low cost 25-35% OEA. Parallel CMS preliminary studies suggest if successful this program can produce 25-35% OEA with an EPO2 of $40/ton which is 50% less than conventional processes.


Grant
Agency: Department of Agriculture | Branch: | Program: SBIR | Phase: Phase I | Award Amount: 100.00K | Year: 2016

Every year over 1 billion tons of fresh animal manure is produced in US and it raises pollution concerns. "Anaerobic digestion" is an environmental friendly and energy efficient way to dispose animal manure. Animal manure is converted to biogas and digestate through this process. The animal manure digestate has a much less pollution potential than untreated animal manure and can be used as a chemical fertilizer replacement. Biogas is a mixture of 60% methane, 40% carbon dioxide and trace amounts of other contaminant gasses. After non-methane component removal, biogas is chemically identical to natural gas. Biogas cannot be injected into the natural gas grid directly because pipeline natural gas requires less than 2% carbon dioxide (CO2). Currently there is no low cost and reliable method to remove such a high percentage of CO2 from biogas, especially for small farm-run anaerobic digesters. The most common use of biogas is to burn it directly and use its energy to generate electricity through microturbines, which limits the economic value of biogas.Compact Membrane Systems is proposing a membrane separation technology which can efficiently remove CO2 from biogas. The proposed fluorinated polymer membrane exhibits preliminary data showing very high CO2 permeation and good CO2/methane selectivity. Parallel data shows that the CMS fluorinated membrane has excellent sulfur (e.g. H2S) resistance and excellent hydrocarbon fouling resistance. Preliminary economic analysis suggest improvements in the economics of carbon dioxide removal of at least 30% compared to water scrubbing or other membrane separation processes. The CMS membrane separation system is a perfect fit for small size biogas upgrading requirements. With this carbon dioxide removal technology, farmers can sell the upgraded biogas directly through the natural gas grid as a renewable natural gas and the economics of anaerobic digestion will be greatly improved.

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