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BioRenewable Chemicals and Solvents

National Renewable Energy Laboratory

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Technology Marketing SummaryAs a spin-off of NREL’s long history of renewable energy research, alternatives to chemicals and solvents have been developed from renewable feedstocks. Traditionally, household and industrial chemicals and solvents are made from the limited petroleum sources. These chemicals and solvents play a major role in many areas of technology and in turn represent a large portion of volatile organic compounds released into the air. By using renewable sources in the production of these chemicals and solvents, emissions can be reduced. The renewable chemicals and solvents listed here may be used for plastics manufacturing, chemical processes, herbicides, adhesives or ingredients of household products.Description99-19 & 98-03: Synthesis of DALA.HCl for herbicides and antitumor compounds from waste paper and other cellulosic materials
NREL scientists have developed a synthesis method for delta-aminolevulinic acid from 5-bromo levulinic acid esters. Delta-aminolevulinic acid in the salt form (DALA.HCl) is known to have potent herbicidal activity against a broad spectrum of weeds and plants and also is being studied as an antitumor compound in humans. The known synthesis of DALA. HCl is difficult to carry out because of the use of toxic and expensive reagents.

The present technology represents a novel and less expensive method for synthesis of delta-aminolevulinic acid as its hydrochloride salt (DALA.HCl), starting from levulinic acid, which is a product that can be produced from cellulosic materials such as waste paper.

98-21 and 98-22: Selective removal of fermentation inhibitors from aqueous biomass hydrolyzate allows for fuel and chemical production
NREL has developed an improved process for the removal of lignin-derived phenolic compounds from dissolved sugars in aqueous biomass hydrolyzate. The process is enabled by adjusting the reaction solution pH, contacting a metal oxide having an affinity for guaiacyl or syringyl functional groups, removing the adsorption complex, and using a fermentative microorganism to convert the sugar fraction into fuels or chemicals.

92-52: Woody Biomass derived pyrolysis oil treated to form levoglucosan for adhesives
Recently, increased attention has been given to finding more affordable feedstocks for bio-renewable adhesives. Researchers at NREL have developed a method for producing high purity levoglucosan from lignocellulosic pyrolysis oils derived from waste biomass, including sources such as newsprint. The method developed is scalable, high yielding and is based on characterized processes of an emerging renewable energy technology platform.

92-42: Process to convert biomass and refuse derived fuel to ethers and/or alcohols
Technology has been developed at NREL that represents a novel and efficient process for converting biorenewable fuels and solvents derived from heterogeneous wastes into ethers and/or alcohols for reformulated gasoline. This invention discloses a method for drying biomass based feedstock, then subjecting it to fast pyrolysis, catalytically cracking vapors from the pyrolysis, condensing any aromatic byproducts, and reacting iso-olefins with an alcohol to form ethers or with water to form alcohols.

89-13: Waste plastics recovered after their useful life and converted into valuable monomers or chemicals
The United States generates about 31 million tons of plastics waste every year. This method provides a controlled, sequential pyrolysis and hydrolysis to convert plastic waste streams from numerous sources into monomers that can be recycled into new plastics or chemicals. Such waste streams can be derived from the manufacture of plastics or from existing sources of nylon, polyolefins, and polycarbonates. The method uses molecular beam mass spectrometry to identify process parameters such as catalytic treatment and differential heating. Once these conditions are identified, engineering processes can be designed based on these conditions. This minimizes disposal requirements for non-biodegradable materials and conserves non-renewable resources.
BenefitsBy making chemicals and goods from renewable sources, NREL technologies will help to develop cleaner, more economical methods and products.Applications and IndustriesBio-fuels
Bio-polymers
Bio-chemicals
Pulp & paper
Detergents
Herbicides
Food & Feed processing
Textile processes
More InformationROI: 89-13 Patent: 5,216,149
ROI: 92-42 Patent: 5,504,259
ROI: 92-52 Patent: 5,432,276
ROI: 98-03 Patent: 5,907,058
ROI: 98-21 Patent: 6,719,908
ROI: 98-22 Patent: 6,737,258
ROI: 99-19 Patent: 6,583,317
Patents and Patent Applications
ID Number
Title and Abstract
Primary Lab
Date
Patent 5,216,149
Patent
5,216,149
Controlled catalytic and thermal sequential pyrolysis and hydrolysis of mixed polymer waste streams to sequentially recover monomers or other high value products
A process of using fast pyrolysis in a carrier gas to convert a plastic waste feedstream having a mixed polymeric composition in a manner such that pyrolysis of a given polymer to its high value monomeric constituent occurs prior to pyrolysis of other plastic components therein comprising: selecting a first temperature program range to cause pyrolysis of said given polymer to its high value monomeric constituent prior to a temperature range that causes pyrolysis of other plastic components; selecting a catalyst and support for treating said feed streams with said catalyst to effect acid or base catalyzed reaction pathways to maximize yield or enhance separation of said high value monomeric constituent in said temperature program range; differentially heating said feed stream at a heat rate within the first temperature program range to provide differential pyrolysis for selective recovery of optimum quantities of the high value monomeric constituent prior to pyrolysis of other plastic components; separating the high value monomeric constituents; selecting a second higher temperature range to cause pyrolysis of a different high value monomeric constituent of said plastic waste and differentially heating the feedstream at the higher temperature program range to cause pyrolysis of the different high value monomeric constituent; and separating the different high value monomeric constituent.
National Renewable Energy Laboratory 06/01/1993
Issued
Patent 5,432,276
Patent
5,432,276
Isolation of levoglucosan from lignocellulosic pyrolysis oil derived from wood or waste newsprint
A method is provided for preparing high purity levoglucosan from lignocellulosic pyrolysis oils derived from wood or waste newsprint. The method includes reducing wood or newsprint to fine particle sizes, treating the particles with a hot mineral acid for a predetermined period of time, and filtering off and drying resulting solid wood or newsprint material; pyrolyzing the dried solid wood or newsprint material at temperatures between about 350.degree. and 375.degree. C. to produce pyrolysis oils; treating the oils to liquid-liquid extraction with methyl isobutyl ketone to remove heavy tar materials from the oils, and to provide an aqueous fraction mixture of the oils containing primarily levoglucosan; treating the aqueous fraction mixtures with a basic metal salt in an amount sufficient to elevate pH values to a range of about 12 to about 12.5 and adding an amount of the salt in excess of the amount needed to obtain the pH range to remove colored materials of impurities from the oil and form a slurry, and freeze-drying the resulting slurry to produce a dry solid residue; and extracting the levoglucosan from the residue using ethyl acetate solvent to produce a purified crystalline levoglucosan.
National Renewable Energy Laboratory 07/11/1995
Issued
Patent 5,504,259
Patent
5,504,259
Process to convert biomass and refuse derived fuel to ethers and/or alcohols
A process for conversion of a feedstock selected from the group consisting of biomass and refuse derived fuel (RDF) to provide reformulated gasoline components comprising a substantial amount of materials selected from the group consisting of ethers, alcohols, or mixtures thereof, comprising: drying said feedstock; subjecting said dried feedstock to fast pyrolysis using a vortex reactor or other means; catalytically cracking vapors resulting from said pyrolysis using a zeolite catalyst; condensing any aromatic byproduct fraction; catalytically alkylating any benzene present in said vapors after condensation; catalytically oligomerizing any remaining ethylene and propylene to higher olefins; isomerizing said olefins to reactive iso-olefins; and catalytically reacting said iso-olefins with an alcohol to form ethers or with water to form alcohols.
National Renewable Energy Laboratory 04/02/1996
Issued
Patent 5,907,058
Patent
5,907,058
Synthesis of an acid addition salt of delta-aminolevulinic acid from 5-bromo levulinic acid esters
A process of preparing an acid addition salt of delta-aminolevulinic acid comprising: dissolving a lower alkyl 5-bromolevulinate and an alkali metal diformylamide in an organic solvent selected from the group consisting of acetonitrile, methanol, tetrahydrofuran, 2-methyltetrahydrofuran and methylformate or mixtures thereof to form a suspension of an alkyl 5-(N,N-diformylamino) levulinate ester; and hydrolyzing said alkyl 5-(N,N-diformylamino) levulinate with an inorganic acid to form an acid addition salt of delta-amino levulinic acid.
National Renewable Energy Laboratory 05/25/1999
Issued
Patent 6,583,317
Patent
6,583,317
Synthesis of acid addition salt of delta-aminolevulinic acid from 5-bromo levulinic acid esters
A process of preparing an acid addition salt of delta-aminolevulinc acid comprising: a) dissolving a lower alkyl 5-bromolevulinate and hexamethylenetetramine in a solvent selected from the group consisting of water, ethyl acetate, chloroform, acetone, ethanol, tetrahydrofuran and acetonitrile, to form a quaternary ammonium salt of the lower alkyl 5-bromolevulinate; and b) hydrolyzing the quaternary ammonium salt with an inorganic acid to form an acid addition salt of delta-aminolevulinic acid.
National Renewable Energy Laboratory 06/24/2003
Issued
Patent 6,719,908
Patent
6,719,908
Phenol removal pretreatment process
A process for removing phenols from an aqueous solution is provided, which comprises the steps of contacting a mixture comprising the solution and a metal oxide, forming a phenol metal oxide complex, and removing the complex from the mixture.
National Renewable Energy Laboratory 04/13/2004
Issued
Patent 6,737,258
Patent
6,737,258
Process for the conversion of and aqueous biomass hydrolyzate into fuels or chemicals by the selective removal of fermentation inhibitors
A process of making a fuel or chemical from a biomass hydrolyzate is provided which comprises the steps of providing a biomass hydrolyzate, adjusting the pH of the hydrolyzate, contacting a metal oxide having an affinity for guaiacyl or syringyl functional groups, or both and the hydrolyzate for a time sufficient to form an adsorption complex; removing the complex wherein a sugar fraction is provided, and converting the sugar fraction to fuels or chemicals using a microorganism.
National Renewable Energy Laboratory 05/18/2004
Issued
Technology Status
Development StageAvailabilityPublishedLast Updated
DevelopmentAvailable09/24/201004/06/2011

Contact NREL About This Technology

To: Eric Payne<Eric.Payne@nrel.gov>