Classifications

• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
  • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
  • C10G2300/10—Feedstock materials
  • C10G2300/1011—Biomass
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
  • C10L1/183—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
  • C10L1/183—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom
  • C10L1/1832—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom mono-hydroxy
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
  • C10L1/183—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom
  • C10L1/1835—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom having at least two hydroxy substituted non condensed benzene rings
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/22—Organic compounds containing nitrogen
  • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
  • C10L1/223—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond having at least one amino group bound to an aromatic carbon atom
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/22—Organic compounds containing nitrogen
  • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
  • C10L1/223—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond having at least one amino group bound to an aromatic carbon atom
  • C10L1/2235—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond having at least one amino group bound to an aromatic carbon atom hydroxy containing
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
  • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
  • Y02E50/00—Technologies for the production of fuel of non-fossil origin
  • Y02E50/10—Biofuels, e.g. bio-diesel
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
  • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
  • Y02P30/00—Technologies relating to oil refining and petrochemical industry
  • Y02P30/20—Technologies relating to oil refining and petrochemical industry using bio-feedstock

Definitions

• Biodiesel is one way to achieve diversification.
• Biodiesel is a generic name for mono-alkyl esters of long-chain fatty acids derived from renewable lipid sources such as vegetable oils, animal fats, or used cooking oils and fats.
• Biodiesel fuels have many names, depending on the feedstocks used to produce them, for example, fatty acid methyl ester (FAME), rapeseed methyl ester (RME), used vegetable oil methyl ester (UVOME), soybean oil methyl ester (SOME) or palm oil methyl ester (POME).
• FAME fatty acid methyl ester
• RME rapeseed methyl ester
• UVOME used vegetable oil methyl ester
• SOME soybean oil methyl ester
• POME palm oil methyl ester
• Biodiesel feedstocks vary widely in their fatty acid compositions (chain length and saturation).
• Biodiesel is typically produced by the reaction of a vegetable oil or an animal fat with an alcohol, such as methanol, in the presence of a catalyst to yield methyl esters (the biodiesel) and glycerine.
• a catalyst such as methanol
• the most commonly used catalyst, potassium hydroxide, is used in transesterification of a wide range of oils and fats, from vegetable to animal, from virgin to used, including those with the highest acid contents.
• the thus produced biodiesel can be distilled to remove excess alcohols and other impurities.
• Other methods for production of biodiesel are known.
• Freshly produced vegetable oils are protected from oxidation by the presence of naturally occurring antioxidants (for example, tocopherols).
• antioxidants for example, tocopherols
• the manufacturing process for biodiesel tends to remove some of the natural antioxidants, leaving the fuel less protected from oxidative degradation.
• distillation of the biodiesel tends to remove essentially all the natural antioxidants leaving the fuel even further unprotected from oxidative degradation.
• Oxidation of biodiesel by contact with air and metal surfaces results in the formation of hydroperoxides. These induce free-radical chain reactions that lead to decomposition into low-molecular-weight, highly oxidized species (aldehydes, ketones, acids) and high-molecular-weight polymeric materials (gums).
• aldehydes, ketones, acids aldehydes, ketones, acids
• high-molecular-weight polymeric materials gums
• These gums tend to cause poor combustion and other engine problems such as deposits on injectors and piston
• the RANCIMAT test is a widely accepted method for measuring the oxidation stability of biodiesel. This test consists of bubbling air through biodiesel that has been heated to 110° C. The amount of short-chain acids present in the distillate (the cleavage products of the fatty acid oxidation) is a direct indication of the oxidation stability of the biodiesel.
• biodiesel has to fulfill a six-hour RANCIMAT test requirement at the production plant and at the pump when refueling vehicles, irrespective of the age of the biodiesel. Other countries may institute similar requirements. Although freshly produced biodiesel may show an oxidation stability (measured by the RANCIMAT method) of more than six hours, this value will decrease over time under common storage conditions if no antioxidants are present.
• Antioxidants are used in hydrocarbon fuels to increase oxidation stability.
• the oxidation stability of biodiesel can also be increased by the addition of antioxidants.
• antioxidant technology for biodiesel is not as well-developed.
• compositions derived from biodiesel mono- or bis-hindered phenolic derived from 2,6-di-tert-butylphenol, and N,N′-di-substituted para-phenylene diamine, wherein the combined amount of the mono- or bis-hindered phenolic and the N,N′-di-substituted para-phenylene diamine is from about 50 ppm to about 5000 ppm based on the biodiesel.
• compositions wherein the biodiesel is crude biodiesel, and wherein the crude biodiesel is derived from soybean oil, canola oil, palm oil, coconut oil, rapeseed oil, corn oil, or used vegetable oil, and wherein the crude biodiesel is a fatty acid methyl ester.
• the biodiesel is distilled biodiesel, and wherein the distilled biodiesel is derived from soybean oil, canola oil, palm oil, coconut oil, rapeseed oil, corn oil, or used vegetable oil.
• compositions wherein the combined amount of the mono- or bis-hindered phenolic and the N,N′-di-substituted para-phenylene diamine is from about 100 ppm to 2500 ppm based on the biodiesel. Further, such compositions are provided wherein the ratio of the mono- or bis-hindered phenolic to N′N-di-substituted para-phenylene diamine varies from about 10:1 to about 1:10 by weight, in particular varies from about 5:1 to about 1:5 by weight.
• compositions derived from biodiesel, 2,4,6-tri-tert-butylphenol, and N,N′-di-substituted para-phenylene diamine wherein the ratio of the 2,4,6-tri-tert-butylphenol to the N,N′-di-substituted para-phenylene diamine varies from about 10:1 to about 1:10 by weight.
• compositions prepared by combining, or comprising, biodiesel, mono- or bis-hindered phenolic derived from 2,6-di-tert-butylphenol, and N,N′-di-substituted para-phenylene diamine, wherein the combined amount of the mono- or bis-hindered phenolic and the N,N′-di-substituted para-phenylene diamine is from about 50 ppm to about 5000 ppm based on the biodiesel.
• This invention also provides methods of improving oxidation stability of a composition comprising biodiesel by combining the composition and mono- or bis-hindered phenolic derived from 2,6-di-tert-butylphenol, and N,N′-di-substituted para-phenylene diamine such that the combined amount of the mono- or bis-hindered phenolic and the N,N′-di-substituted para-phenylene diamine is from about 50 ppm to 5000 ppm based on the biodiesel.
• biodiesel is crude biodiesel, and wherein the crude biodiesel is derived from soybean oil, canola oil, palm oil, coconut oil, rapeseed oil, corn oil, or used vegetable oil, and wherein the crude biodiesel is a fatty acid methyl ester. Also provided are such methods wherein the biodiesel is distilled biodiesel, and wherein the distilled biodiesel is derived from soybean oil, canola oil, palm oil, coconut oil, rapeseed oil, corn oil, or used vegetable oil.
• such methods are provided wherein the combined amount of the mono- or bis-hindered phenolic and the N,N′-di-substituted para-phenylene diamine is from about 100 ppm to 2500 ppm based on the biodiesel. Further, such methods are provided wherein the ratio of the mono- or bis-hindered phenolic to N′N-di-substituted para-phenylene diamine is varies from about 10:1 to about 1:10 by weight, in particular varies from about 5:1 to about 1:5 by weight.
• the mono- or bis-hindered phenolic derived from 2,6-di-tert-butylphenol can comprise ortho-tert-butylphenol, 2,6-di-tert-butylphenol, 2,4,6-tri-tert-butylphenol, 4,4′-methylenebis(2,6-di-tert-butylphenol), 3,5-di-tert-butyl-4-hydroxyphenylhydrocinnamicacid, methyl ester, 3,5-di-tert-butyl-4-hydroxyphenylhydrocinnamicacid, C7-C9 branched alkyl esters, 2,6-di-tert-butyl-alpha-dimethylamino-p-cresol; butylated hydroxytoluene, or 2,4,6-tri-tert-butylphenol; and the N,N′-di-substituted para-phenylene diamine can comprise N,N′-di-sec-butyl
• the weight ratio of the 2,4,6-tri-tert-butylphenol to the N,N′-di-substituted para-phenylene diamine is greater than about 1, in some embodiments, greater than about 1.25, and in other embodiments, greater than about 1.5.
• Suitable mono or bis-hindered phenolics derived from 2,6-di-tert-butylphenols can comprise 2,6-di-tert-butylphenol (e.g., the product comprising 2,6-di-tert-butylphenol sold under the trademark ETHANOX 4701); 2,4,6-tri-tert-butylphenol; combinations of ortho-tert-butylphenol, 2,6-di-tert-butylphenol, and 2,4,6-tri-tert-butylphenol (e.g., the product comprising ortho-tert-butylphenol, 2,6-di-tert-butylphenol, and 2,4,6-tri-tert-butylphenol sold under the trademark ETHANOX 4733); combinations of 2,6-di-tert-butylphenol and 2,4,6-tri-tert-butylphenol (e.g., the product comprising 2,6-di-tert-butylphenol and 2,4,6-tri-tert-
• Suitable N,N′-di-substituted para-phenylene diamines can comprise N,N′-di-sec-butyl-p-phenylenediamine (PDA), N,N′-diisopropyl-p-phenylenediamine, N,N′-bis-(1,4-dimethylpentyl)-p-phenylenediamine, or combinations thereof.
• concentration of the N,N′-dis-substituted para-phenylene diamine can be from about 0.0025 wt % to about 0.25 wt % of the total biodiesel.
• biodiesel comprises crude biodiesel, distilled biodiesel, or any individual chemical component of either.
• Crude biodiesel comprises 8 carbon to 22 carbon saturated, mono-unsaturated, di-unsaturated, or tri-unsaturated methyl ester, or fatty acid methyl ester derived from a vegetable or animal source. Processes for producing crude biodiesel are well know to those skilled in the art.
• Example individual chemical components of fatty acid methyl ester include methyl stearate (n-octadecanoic acid, methyl ester), methyl oleate (9-octadecenoic acid, methyl ester), methyl vaccenate (11-octadecenoic acid methyl ester), methyl linoleate (9,12-octadecadienoic acid, methyl ester), or methyl linoleniate (9,12,15-octadecatrienoic acid, methyl ester), caprylic acid methyl ester, capric acid methyl ester, lauric acid methyl ester, myristic acid methyl ester, palmitic acid methyl ester, arachidic acid methyl ester, behenic acid methyl ester, lauroleic acid methyl ester, myristoleic acid methyl ester, palmitoleic acid methyl ester, elaidic acid methyl ester, gadoleic acid
• Distilled biodiesel comprises crude biodiesel that has been subjected to at least one distillation step, e.g., to remove excess alcohols, residual glycerine, and other impurities, and includes biodiesel obtained as a specific cut or fraction produced during the distillation of crude biodiesel. Methods of distilling crude biodiesel are well known to those skilled in the art.
• Crude biodiesel can be derived from any suitable vegetable or animal source, including for example soybean oil, low erucic acid rapeseed oil (Canola Oil), high erucic acid rapeseed oil, palm oil, used cooking oil, vegetable oil, coconut oil, corn oil, cottonseed oil, safflower oil, sunflower oil, peanut oil, sugar cane oil, lard, tallow, poultry fat, yellow grease, and the like.
• Fatty acid methyl ester in crude biodiesel can be produced, e.g., by a transesterification reaction between a vegetable or animal based triglyceride and methanol using a catalyst, as is familiar to those skilled in the art.
• Crude biodiesel or distilled biodiesel can be subjected to additional chemical treatment, e.g., to reduce unsaturation.
• compositions according to this invention comprising, or prepared by combining, biodiesel, mono or bis-hindered phenolic derived from 2,6-di-tert-butylphenol (component (2)), and N,N′-di-substituted para-phenylene diamine (component (3)), can comprise, or be prepared by combining, from about 50 ppm to about 5000 ppm of components (2) and (3), based on the amount of the biodiesel, and can comprise, or be prepared by combining, from about 100 ppm to about 2500 ppm of components (2) and (3), based on the amount of the biodiesel.
• Methods of improving oxidation stability of biodiesel according to this invention can comprise combining the biodiesel and from about 50 ppm to about 5000 ppm of antioxidant component comprising mono or bis-hindered phenolic derived from 2,6-di-tert-butylphenol and N,N′-di-substituted para-phenylene diamine.
• Such methods can also comprising combining the biodiesel component and from about 100 ppm to about 2500 ppm of antioxidant component comprising mono or bis-hindered phenolic derived from 2,6-di-tert-butylphenol and N,N′-di-substituted para-phenylene diamine.
• the identified biodiesel sample and antioxidant composition were combined. In some of the comparative examples, no antioxidant composition was added to the identified biodiesel. In the examples in which the biodiesel was distilled, the biodiesel was distilled using standard techniques known to those skilled in the art. In each example, the oxidation stability of the combination (or of just the biodiesel in certain of the comparative examples) was tested with the RANCIMAT test using RANCIMAT test method (DIN EN 14112). In each instance the sample size was 3 grams, the temperature was 110° C., the air source was purified dry air, and the flow rate was 10 L/hr. The data in Table 1 clearly shows the benefits of this invention.
• reactants and components referred to by chemical name or formula anywhere in the specification or claims hereof, whether referred to in the singular or plural, are identified as they exist prior to being combined with or coming into contact with another substance referred to by chemical name or chemical type (e.g., another reactant, a solvent, or etc.). It matters not what chemical changes, transformations and/or reactions, if any, take place in the resulting combination or solution or reaction medium as such changes, transformations and/or reactions are the natural result of bringing the specified reactants and/or components together under the conditions called for pursuant to this disclosure.
• the reactants and components are identified as ingredients to be brought together in connection with performing a desired chemical reaction or in forming a combination to be used in conducting a desired reaction.
• Biodiesel comprises crude biodiesel, distilled biodiesel, or any individual chemical component of either.
• Crude biodiesel comprises 8 carbon to 22 carbon saturated, mono-unsaturated, di-unsaturated, or tri-unsaturated methyl ester, or fatty acid methyl ester derived from a vegetable or animal source.
• Distilled biodiesel comprises crude biodiesel that has been subjected to at least one distillation step, e.g., to remove excess alcohols, residual glycerine, and other impurities, and includes biodiesel obtained as a specific cut or fraction produced during the distillation of crude biodiesel.
• TTBP comprises essentially 100% 2,4,6-tri-tert-butylphenol.

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• Chemical & Material Sciences (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Engineering & Computer Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Fats And Perfumes (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Lubricants (AREA)
• Liquid Carbonaceous Fuels (AREA)

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• 2008
  • 2008-03-13 CA CA002681753A patent/CA2681753A1/en not_active Abandoned
  • 2008-03-13 WO PCT/US2008/056763 patent/WO2008121526A1/en active Application Filing
  • 2008-03-13 BR BRPI0809615A patent/BRPI0809615A8/pt not_active IP Right Cessation
  • 2008-03-13 JP JP2010501053A patent/JP2010522809A/ja not_active Withdrawn
  • 2008-03-13 EP EP08732069A patent/EP2137283A1/en not_active Withdrawn
  • 2008-03-13 CN CN200880010251A patent/CN101688137A/zh active Pending
  • 2008-03-13 AU AU2008232984A patent/AU2008232984A1/en not_active Abandoned
  • 2008-03-13 RU RU2009139760/05A patent/RU2009139760A/ru unknown
  • 2008-03-13 KR KR1020097022265A patent/KR20100015881A/ko not_active Application Discontinuation
  • 2008-03-13 US US12/593,383 patent/US20100107481A1/en not_active Abandoned
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