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WO2016022201A1 - Procédés de conversion de glucides en oxo-hydrocarbures et furanes - Google Patents

Procédés de conversion de glucides en oxo-hydrocarbures et furanes Download PDF

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Publication number
WO2016022201A1
WO2016022201A1 PCT/US2015/034139 US2015034139W WO2016022201A1 WO 2016022201 A1 WO2016022201 A1 WO 2016022201A1 US 2015034139 W US2015034139 W US 2015034139W WO 2016022201 A1 WO2016022201 A1 WO 2016022201A1
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calcium
carbohydrate
combination
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heating
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Thomas Tao
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C27/00—Processes involving the simultaneous production of more than one class of oxygen-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • C07C45/60—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in six-membered rings

Definitions

  • the present invention relates to methods for converting carbohydrates into hydrocarbons and heterocyclic compounds, especially oxo hydrocarbons and furans, with reduced formation of char.
  • the methods of the invention include reacting a carbohydrate with reactant having a strong chemical affinity for carbon dioxide.
  • the present invention has applications in the fields of organic chemistry, petroleum chemistry, and bio-chemicals.
  • Carbohydrates also known as saccharides, are the dominant chemical constituents of the most abundant and dominant biomasses on earth, which comprise more than 60 % of the total known plant mass. Common carbohydrates include sugars, starches, cellulose and hemicelluloses, and their various chemical derivatives. Carbohydrates have the general chemical formula C m (H 2 0) n , where m and n can be equal or not, and the hydrogen and oxygen are in a ratio of 2:1 as for water (whence the name "hydrate of carbon” , since the constituents of water, hydrogen (H) and hydroxyl (OH), are bound to each carbon atom). Carbohydrates are neither chemical hydrates nor fatty acids; instead, they are polyhydroxyl-, aldehyde-, and ketone-containing compounds.
  • the carbohydrates are divided into four chemical families: monosaccharides, disaccharides, oligosaccharides, and polysaccharides.
  • the monosaccharides and disaccharides are commonly referred to as "sugars" .
  • a common example of a monosaccharide is glucose; common examples of disaccharides are sucrose and lactose.
  • Oligosaccharides are chains of fewer than ten saccharides; polysaccharides are chains longer than ten saccharides.
  • Biologically, polysaccharides store chemical energy (e.g., starch and glycogen) and provide structural support (e.g., cellulose and hemicellulose in plants and chitin in arthropods) .
  • Cellulose has the chemical formula (C 6 H 10 O 5 ) n ; it is a polysaccharide consisting of a linear chain of several hundred to over ten thousand ⁇ (1 — > 4)-linked D-glucose units.
  • Cellulose is the primary structural component of the cell wall of green plants and in many forms of algae and the oomycetes. Cellulose also is both abundant and renewable: About one-third of the mass of all plant matter is cellulose (the percentage may be higher in some plants, such as 90% in cotton and 40-50% in trees).
  • Another major carbohydrate is hemicellulose. Hemicellulose is a polysaccharide consisting of various sugars. About 20% of all plant biomass is hemicellulose. As such, hemicellulose too is both abundant and renewable.
  • Hydrocarbons so named because they formally correspond to "hydrogenated carbon” (C m H 2n ) , and oxygen-containing derivatives ( “oxo hydrocarbons” ) , are also derived from carbohydrates by a variety of geological processes, operating over “geological" time scales, that are still not well understood.
  • the utility of hydrocarbons is well understood. Nevertheless, many scientists fear that global hydro- carbon production will soon peak, and may already peaked, thus leaving the world with the prospect of dwindling supplies of hydrocarbon fuel stocks and feedstocks for nearly all of the most important chemical building blocks.
  • the present invention provides methods and materials for the efficient conversion of carbohydrates into various oxo hydrocarbons and furans.
  • the present invention provides methods for converting sucrose into acetone, acetol, furfural alcohol, and 2,5-bis(hydroxymethyl)furan.
  • the present invention provides methods for converting carbohydrates into oxo hydrocarbons and furans.
  • the methods provided by the present invention comprise combining a carbohydrate with a carbon dioxide-scavenging agent, and heating the combination under conditions effective to cause the production of at least one oxo hydrocarbon or furan with an exothermicty of less than about 100 kcal mol -1 .
  • the carbohydrate includes at least one saccharide, and more specifically one selected from the group consisting of mono-, di-, and tri-saccharides. Still more specific embodiments are those for which the carbohydrate is a mono- or di-saccharide.
  • Two particular embodiments are those for which the carbohydrate is a di-saccharide, and those for which the carbohydrate is a mono-saccharide. Of the latter, yet more specific embodiments are those for which the carbohydrate is selected from the group consisting of sucrose, glucose, and fructose.
  • Other embodiments of the invention comprise combining a carbohydrate with a carbon dioxide-scavenging agent, and heating the combination under conditions effective to cause the production of at least one oxo hydrocarbon or furan with an exothermicty of less than about 100 kcal mol -1 , as described above, and further wherein the conditions effective to cause the production of at least one oxo hydrocarbon include heating the combination.
  • the reactants are combined at a temperature less than about 300 °C.
  • the combination is heated to a temperature less than about 250 °C.
  • the combination is heated to a temperature less than about 200 °C.
  • the combination is heated to a temperature between about 150 °C and about 200 °C.
  • inventions comprise combining a carbohydrate with a carbon dioxide-scavenging agent, and heating the combination under conditions effective to cause the production of at least one oxo hydrocarbon or furan with an exother- micty of less than about lOO kcal mol -1 , as described above, and further wherein the carbon dioxide-scavenging agent is selected from the group consisting of magnesium oxide, calcium formate, calcium acetate, calcium oxalate, calcium hydroxide, calcium glycolate, and l-butyl-3-methylimidazole.
  • the carbon dioxide-scavenging agent is selected from the group consisting of calcium formate, calcium acetate, calcium oxalate, calcium hydroxide, calcium glycolate.
  • Other embodiments of the invention comprise combining a carbohydrate with a carbon dioxide-scavenging agent, and heating the combination under conditions effective to cause the production of at least one oxo hydrocarbon or furan with an exothermicty of less than about lOO kcal mol -1 , as described above.
  • the exothermicty is less than about 50 kcal mol more specifically less than about 25 kcal mol -1 , still more specifically less than about 10 kcal mol -1 , and still more specifically less than about 5 kcal mol -1 .
  • Char refers to a charcoal-like material produced by cooking organic matter in a low-oxygen environment. Char is produced commercially by pyrolysis reactions in amounts ranging from 15%-50% of the initial feedstock. Char contains varying amounts of carbon, hydrogen, and oxygen as well as ash and other impurities that, together with the structure, determine the properties.
  • Carbon Dioxide-Scavenging Agent refers to a material that has a high affinity to bind with, or otherwise sequesters or scavenges, C0 2 , and does not chemically or otherwise interfere with the conversion of carbohydrate to or- ganics, in particular oxo hydrocarbons.
  • suitable C0 2 scavenging agents include: (i) a metal oxide or metal hydroxide of the alkaline, alkaline earth, or rare alkaline earth metals, which is basic with a strong chemical affinity for carbon dioxide; (ii) a nitrogen-containing-heterocyclic- containing compound, such as imidazole, pyrazole, pyrrole, pyrazine, pyridazine, pyrimidine, pyridine, and their derivatives and ionic salts; (iii) basic chemicals of NaA10 2 , Na 2 Si0 3 ; and (iv) any combination thereof.
  • a metal oxide or metal hydroxide of the alkaline, alkaline earth, or rare alkaline earth metals which is basic with a strong chemical affinity for carbon dioxide
  • a nitrogen-containing-heterocyclic- containing compound such as imidazole, pyrazole, pyrrole, pyrazine, pyridazine, pyrimidine,
  • Furan and Furans include both the specific heterocyclic compound furan (C 4 H 4 0) derivatives thereof, either individually or in combination, unless specifically referring to the compound furan per se.
  • the present invention provides methods and materials for the efficient conversion of carbohydrates into various oxo hydrocarbons and furans.
  • the present invention provides methods for converting carbohydrates into oxo hydrocarbons and furans.
  • the methods provided by the present invention comprise combining a carbohydrate with a carbon dioxide- scavenging agent, and heating the combination under conditions effective to cause the production of at least one oxo hydrocarbon or at least one furan, or combination thereof, with an exothermicty of less than about lOO kcal mol -1 .
  • the carbohydrate includes at least one saccharide; in a more specific embodiment, the carbohydrate is selected from the group consisting of mono-, di-, and tri-saccharides. Still more specific embodiments are those for which the carbohydrate is a mono- or di-saccharide. Two particular embodiments are those for which the carbohydrate is a di-saccharide, and those for which the carbohydrate is a mono-saccharide. Of the latter, yet more specific embodiments are those for which the carbohydrate is selected from the group consisting of sucrose, glucose, and fructose.
  • Other embodiments of the invention comprise combining a carbohydrate with a carbon dioxide-scavenging agent, and heating the combination under conditions effective to cause the production of at least one oxo hydrocarbon or at least one furan, or combintion thereof, with an exothermicty of less than about lOO kcal mol -1 , as described above, and further wherein the conditions include heating the combination.
  • the combination is heated to a temperature less than about 300 °C. In still more specific embodiments, the combination is heated to a temperature less than about 250 °C. In yet more specific embodiments, the combination is heated to a temperature less than about 200 °C. And in still more specific embodiments, the combination is heated to a temperature between about 150 °C and about 200 °C.
  • Other embodiments of the invention comprise combining a carbohydrate with a carbon dioxide-scavenging agent, and heating the combination under conditions effective to cause the production of at least one oxo hydrocarbon or at least one furan, or combination thereof, with an exothermicty of less than about lOO kcal mol -1 , as described above, and further wherein the carbon dioxide-scavenging agent is selected from the group consisting of magnesium oxide, calcium formate, calcium acetate, cal- cium oxalate, calcium hydroxide, calcium glycolate, and l-butyl-3-methylimidazole.
  • the carbon dioxide-scavenging agent is selected from the group consisting of calcium formate, calcium acetate, calcium oxalate, calcium hydroxide, calcium glycolate, and l-butyl-3-methylimidazole.
  • Other embodiments of the invention comprise combining a carbohydrate with a carbon dioxide-scavenging agent, and heating the combination under conditions effective to cause the production of at least one oxo hydrocarbon or at least one furan, or combination thereof, with an exothermicty of less than about 100 kcal mol -1 , as described above, and further wherein the at least one oxo hydrocarbon or at least one furan, or combination thereof, is selected from the group consisting of acetone, acetol, furfuryl alcohol, 2,5-bis(hydroxymethyl)furan and combinations thereof.
  • the at least one oxo hydrocarbon or at least one furan, or combination thereof is a mixture of acetone, acetol, and furfuryl alcohol.
  • the exothermicty is less than about 50 kcal mol and more specifically less than about 25 kcal mol -1 , and still more specifically less than about 10 kcal mol -1 , and still more specifically less than about 5 kcal mol -1 .
  • reaction conditions for the chemical reactions described herein are substantially non-aqueous. In still other embodiments, the reaction conditions for the chemical ractions described herein are without any significant amount of solvent. In still more specific embodiments, the reaction conditions for the chemical reactions described herein are substantially solid-state reaction conditions.
  • a particular embodiment of the method of the invention comprises combining a carbohydrate selected from the group consisting of sucrose, glucose, and fructose with a carbon dioxide-scavenging agent selected from the group consisting of magnesium oxide, calcium formate, calcium acetate, calcium oxalate, calcium hydroxide, calcium glycolate, and l-butyl-3-methylimidazole, and heating the combination at a temperature of between about 130 °C and about 220 °C.
  • a carbohydrate selected from the group consisting of sucrose, glucose, and fructose
  • a carbon dioxide-scavenging agent selected from the group consisting of magnesium oxide, calcium formate, calcium acetate, calcium oxalate, calcium hydroxide, calcium glycolate, and l-butyl-3-methylimidazole
  • the carbon dioxide-scavenging agent is selected from the group consisting of calcium formate, calcium acetate, calcium oxalate, calcium hydroxide, calcium glycolate, and l-butyl-3-methylimidazole, and the combination with the carbohydrate listed above is heated at a temperature of between about 130 °C and about 220 °C.
  • a starting material suitable for making a C0 2 scavenging material is made.
  • Typical starting materials include calcium oxide (CaO) and limestone powder, which can be purchased from commercial sources as indicated below.
  • CaO the starting material is mixed with water to first make calcium hydroxide (Ca(OH) 2 ), which is then rigorously dried.
  • Ca(OH) 2 calcium hydroxide
  • limestone powder the powder is first calcined and then mixed with water. Still other materials and methods for making suitable scavengers will be apparent to those having ordinary skill in the art.
  • Suitable scavengers include magnesium oxide, calcium formate, calcium acetate, calcium oxalate, calcium hydroxide, calcium glycolate, and l-butyl-3-methylimidazole.
  • the scavenger can be used individually or in combniation. The preparation of these materials to make suitable scavengers will be understood by those having ordinary skill in the art.
  • the reactants are heated at a temperature less than about 300 °C, more particularly less than about 250 °C, and still more particularly less than about 200 °C. Still more specific embodiments are those in which the reactants are heated at a temperature between about 130 °C and about 300 °C, more particularly, between about 150 °C and about 250 °C, still more particularly between about 150 °C and about 220 °C, and yet still more particularly between about 150 °C and about 200 °C.
  • heating of the reactants is heating of reactants can be achieved in various ways that will be familiar to those having ordinary skill in the art.
  • heating can be direct or indirect means.
  • Non-limiting examples of direct heating include using a pre-heated carrier gas such as N 2 or product components such as acetone vapor, or a combination thereof, passing through the reactants.
  • Non- limiting examples of indirect heating include contact heating by placing reactants in contact with a surface of retaining walls heated by a heat source such as resistance electric heating, high pressure steam, a preheated media such as oils, or by radiation (solar, artificial lighting, etc.)
  • the heating can also be provided by microwave, direct radiations, dielectric at high frequency electric field. The determination of heating rates will be familiar to those having ordinary skill in the art.
  • the crucible was placed in a tubular furnace (Carbolite, six-inch diameter) and was heated to 360 °C while held for 30 min. The sample was then cooled down to room temperature in a desiccator.
  • a modified tubular furnace (Carbolite, 6-inch in diameter) was used as the heating mantel. It was set up horizontally and electrically heated.
  • a 100 niL round bottom modified Schlenk reactor from LaBoy was used as the liquid-phase solid-state reactor.
  • the reactor system was set up to allow little or no reflux or no condensate flowing back into the reactor during the reaction.
  • a second thermal couple ( "TC" ) was inserted inside the reactant mixture to monitor the reaction temperature during the reaction.
  • the heating mantel was set to 250 °C at the maximum heating rate possible.
  • the reaction temperature was monitored by a second thermal couple inserted inside of the reactant mixture. Substantial difference in temperature readings between the heating mantel and the monitor was observed. It only took 9 min for the heating mantel to reach the pre-set temperature of 250 °C, while at the same time the reactant mixture (second TC) was merely at 68.4 °C. When the temperature inside the reactant mixture reached 155.3 °C, a colorless condensate was formed.
  • Lime stone powder was purchased from online kelp41ess.com which contained 98% calcium carbonate.
  • the powder was a low cost grade lime with green hue and its main use was for balancing pH and supplementing calcium for soil. 1000 g of the powder was added to a ceramic crucible (A1 2 0 3 ) which was further placed in a box furnace (Vulcan model 3-550) for calcination. Alternatively a Carbolite tube furnace with six-inch diameter was used for calcination of samples less than 300 g.
  • the lime powder was heated to 1050 °C and held for two hours.
  • the calcined sample was cooled down to ambient temperature inside the box furnace with its door closed. Alternatively for samples less than 300 g they were transferred to and cooled down in a desiccator.
  • a water cooled condenser with a three-way cow-type receiver was used for collecting condensates.
  • Nitrogen gas (99.99 %) was installed to flush or to purge the reactor before, during and after reaction.
  • a second thermal couple was inserted inside the reactant mixture to monitor the reaction temperature.
  • Nitrogen gas at a flow rate of 200 rriL min -1 was used to flush the reactor for 30 min before the heating, then reduced to 100 rriL min -1 during heating and further reduced to lO mL min -1 during the peak of the reaction.
  • the reactor was heated at a preset rate of 40 °C per hour till 230 °C.
  • the reaction temperature was monitored by a second thermal couple inserted about 2 cm beneath the surface of the reactant mixture. Substantial difference of temperature readings between the heating mantel and the monitor was observed. When the heating mantel temperature reached 202 °C, the second TC monitor inside the reactant mixture only read 151.9 °C— at which noticeable condensates were formed with faint greenish tint.
  • Example 3 Sugar cane, Scavenger Made From Lime Stone Powder and a 20-cm Long Tubular Reactor
  • Lime stone powder was purchased from online kelp41ess.com which contained 98% calcium carbonate.
  • the powder was a low cost grade lime with green hue and its main use was for balancing pH and supplementing calcium for soil. 1000 g of the powder was added to a ceramic crucible (A1 2 0 3 ) which was further placed in a box furnace (Vulcan model 3-550) for calcination. Alternatively a Carbolite tube furnace with 6-inch diameter was used for calcination of samples less than 300 g.
  • the lime powder was heated to 1050 °C and held for two hours.
  • the calcined sample was cooled down to ambient temperature inside the box furnace with its door closed. Alternatively for samples less than 300 g they were transferred to and cooled down in a desiccator.
  • the aged cane as it is was mechanically cut into pieces less than 1 cm long and was further crushed into fine dust (like saw dust) in a 16-speed kitchen food blender made by Oster at the highest setting.
  • the sugar cane dust was then measured for its water content, its sugar content, and its bagasse (fiber) content and they were estimated to be 14.8 wt.-%, 29.7 wt.- %, and 55.5 wt.-% respectively.
  • the water content was estimated by its weight loss after drying the cane dust at 150 °C for 24 h till no measurable weight changes.
  • the sugar content was estimated by its weight loss after repeated de-ionized water washings, vacuum nitrations and subsequent dryings at 150 °C till no measurable weight changes.
  • Equal weight of C0 2 scavenger powder and cane dust was prepared by mechanical mixing and grinding in pestle and mortar.
  • a stock of the reactant mixture thus made consisted of 20.47g of C0 2 scavenger and 20.76 g of the cane dust.
  • Step 4 Horizontally Oriented Liquid-Phase Solid-State Reactor System
  • a Carbolite tube furnace as the heating mantel was set horizontally.
  • a 20 cm- long tubular Pyrex reactor was inserted half way into the hot zone of the furnace with the opening end tilted downward preventing condensates from flowing back into the hot zone of the reactor during reaction.
  • An air cooled elbow and a 5-ml collection flask was used to collect the liquid product. No nitrogen blank gas was used.
  • the reactor was first heated at the fastest possible heating rate till 150 °C (less than 5 min from the start). It was then manually and incrementally raised by 10 °C at every 5 min to 300 °C. At 160 °C colorless condensate was formed on the cold side of walls of the reactor and the elbow. At 210 °C to 220 °C the liquid collected appeared to show a faint greenish tint, and soon after a pleasant and sweet aroma resembling food processing such as cooking of Jasmin rice appeared. The heating was manually stopped when it reached 290 °C and the reactor was immediately cooled down.
  • the charged reactant mixture contained 2.052 g of the cane dust that was estimated to be 0.303 g of water, 0.609 g of sugar and 1.139 g of bagasse (fiber).
  • the total amount of volatile formed during reaction plus water from the cane dust (about 0.303 g) was measured at 0.701 g.
  • Lime stone powder was purchased from online kelp41ess.com which contained 98 % calcium carbonate.
  • the powder was a low cost grade lime with green hue and its main use was for balancing pH and supplementing calcium for soil. 1000 g of the powder was added to a ceramic crucible (A1 2 0 3 ) which was further placed in a box furnace (Vulcan model 3-550) for calcination. Alternatively a Carbolite tube furnace with 6 inch diameter was used for calcination of samples less than 300 grams.
  • the lime powder was heated to 1050 °C and held for two hours.
  • the calcined sample was cooled down to ambient temperature inside the box furnace with its door closed. Alternatively for samples less than 300 g they were transferred to and cooled down in a desiccator. For 1000 g of lime stone powder, after calcination, 595 g of the calcined powder was obtained.
  • a tubular furnace (Carbolite one-inch in diameter) was used as the heating mantel and it was placed horizontally.
  • a 10 rriL tubular reactor from Ace was used as the liquid-phase solid-state reactor.
  • the heating mantel was set to 250 °C at a heating rate of 3.33 °C min -1 . Condensate on the walls of the elbow and the collector flask was observed when the temperature reached 135 °C and the reaction was stopped when it reached 250 °C. [0088] The total amount of volatiles and condensates formed during the reaction was weighed to be 0.498 gram per 0.998 g fructose charged, giving a yield of 49.9 weight-% of based on sugar charged.
  • Lime stone powder was purchased from online kelp41ess.com which contained 98 % calcium carbonate.
  • the powder was a low cost grade lime with green hue and its main use was for balancing pH and supplementing calcium for soil. 1000 g of the powder was added to a ceramic crucible (A1 2 0 3 ) which was further placed in a box furnace (Vulcan model 3-550) for calcination. Alternatively a Carbolite tube furnace with 6 inch diameter was used for calcination of samples less than 300 g.
  • the lime powder was heated to 1050 °C and held for two hours.
  • the calcined sample was cooled down to ambient temperature inside the box furnace with its door closed. Alternatively for samples less than 300 g they were transferred to and cooled down in a desiccator.
  • a tubular furnace (Carbolite one- inch in diameter) was used as the heating mantel and it was placed horizontally.
  • a 10 rriL tubular reactor from Ace was used as the liquid-phase solid-state reactor.
  • the heating mantel was set to 250 °C at a heating rate of 3.33 °C min _1 . Condensate on the walls of the elbow and the collector flask was observed when the temperature reached 135 °C and the reaction was manually stopped when it reached 250 °C.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Saccharide Compounds (AREA)

Abstract

Cette invention concerne des procédés et des matériaux permettant de convertir des glucides en oxo-hydrocarbures et furanes. Dans certains modes de réalisation, un glucide choisi dans le groupe constitué par le saccharose, le glucose, et le fructose est combiné à un agent d'épuration de dioxyde de carbone choisi dans le groupe constitué par l'oxyde de magnésium, le formiate de calcium, l'acétate de calcium, l'oxalate de calcium, l'hydroxyde de calcium, le glycolate de calcium, et le 1-butyl-3-méthylimidazole. La combinaison est chauffée à une température comprise entre environ 130 et environ 220°C.
PCT/US2015/034139 2014-08-07 2015-06-04 Procédés de conversion de glucides en oxo-hydrocarbures et furanes Ceased WO2016022201A1 (fr)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4153514A (en) * 1975-02-27 1979-05-08 Occidental Petroleum Corporation Pyrolysis process for solid wastes
US4523928A (en) * 1980-04-28 1985-06-18 Battelle Development Corporation Gasohol production from thermochemical conversion of biomass to ethanol
US20130178617A1 (en) * 2011-09-28 2013-07-11 Ronald Raines Catalytic conversion of cellulose to fuels and chemicals using boronic acids
US9045448B1 (en) * 2013-01-03 2015-06-02 Thomas Tao Methods for converting carbohydrates into oxygenated hydrocarbons

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4153514A (en) * 1975-02-27 1979-05-08 Occidental Petroleum Corporation Pyrolysis process for solid wastes
US4523928A (en) * 1980-04-28 1985-06-18 Battelle Development Corporation Gasohol production from thermochemical conversion of biomass to ethanol
US20130178617A1 (en) * 2011-09-28 2013-07-11 Ronald Raines Catalytic conversion of cellulose to fuels and chemicals using boronic acids
US9045448B1 (en) * 2013-01-03 2015-06-02 Thomas Tao Methods for converting carbohydrates into oxygenated hydrocarbons

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
ASSARY ET AL.: "Glucose and fructose to platform chemicals: understanding the thermodynamic landscapes of acid-catalysed reactions using high-level ab initio methods.", PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2012, Retrieved from the Internet <URL:http://www.researchgate.net/profile/Rajeev_Assary/publication/230762756_Glucose_and_fructose_to_platform_chemicals_understanding_the_thermodynamic_landscapes_of_acid-catalysed_reactions_using_high-level_ab_initio_methods/links/0deec51b00b581f6ff000000.pdf> [retrieved on 20150916] *

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