WO2008121526A1 - Antioxidant blends for fatty acid methyl esters (biodiesel) - Google Patents

Antioxidant blends for fatty acid methyl esters (biodiesel) Download PDF

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Publication number
WO2008121526A1
WO2008121526A1 PCT/US2008/056763 US2008056763W WO2008121526A1 WO 2008121526 A1 WO2008121526 A1 WO 2008121526A1 US 2008056763 W US2008056763 W US 2008056763W WO 2008121526 A1 WO2008121526 A1 WO 2008121526A1
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WIPO (PCT)
Prior art keywords
tert
butylphenol
biodiesel
bis
phenylene diamine
Prior art date
Application number
PCT/US2008/056763
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English (en)
French (fr)
Inventor
Vincent J. Gatto
Gangkai Zhao
Emily Schneller
Original Assignee
Albemarle Corporation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Albemarle Corporation filed Critical Albemarle Corporation
Priority to AU2008232984A priority Critical patent/AU2008232984A1/en
Priority to CA002681753A priority patent/CA2681753A1/en
Priority to CN200880010251A priority patent/CN101688137A/zh
Priority to JP2010501053A priority patent/JP2010522809A/ja
Priority to BRPI0809615A priority patent/BRPI0809615A8/pt
Priority to US12/593,383 priority patent/US20100107481A1/en
Priority to EP08732069A priority patent/EP2137283A1/en
Publication of WO2008121526A1 publication Critical patent/WO2008121526A1/en

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    • 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 potassium hydroxide
  • 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.
  • 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 0 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 In Europe and Brazil, 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. [0005] Antioxidants are used in hydrocarbon fuels to increase oxidation stability. The oxidation stability of biodiesel can also be increased by the addition of antioxidants. However, given the relative youth of biodiesel fuels as compared to hydrocarbon fuels, antioxidant technology for biodiesel is not as well-developed. [0006] Thus, there is a need for improved antioxidant compositions for use in biodiesel fuels and for biodiesel compositions comprising such antioxidant compositions that are economically suited for commercial use.
  • 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 biodiesei, 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.
  • 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 biodiese!, 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-d i-tert-b utyl-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-p- phenylenediamine, N, N'- diisopropyl-p-phenylenediamine, or N,N'-bis-(1 ,4- dimethylpentyl)-p-phenylenediamine.
  • the weight ratio of the 2,4,8-tri-tert-butyIphenol 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.
  • 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- (i ⁇ -dimethylpenty ⁇ -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
  • 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.
  • 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. Accordingly, even though the claims hereinafter may refer to substances, components and/or ingredients in the present tense ("comprises”, “is”, etc.), the reference is to the substance, component or ingredient as it existed at the time just before it was first contacted, combined, blended or mixed with one or more other substances, components and/or ingredients in accordance with the present disclosure. Whatever transformations, if any, which occur in situ as a reaction is conducted is what the claim is intended to cover.
  • 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)
PCT/US2008/056763 2007-03-28 2008-03-13 Antioxidant blends for fatty acid methyl esters (biodiesel) WO2008121526A1 (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
AU2008232984A AU2008232984A1 (en) 2007-03-28 2008-03-13 Antioxidant blends for fatty acid methyl esters (biodiesel)
CA002681753A CA2681753A1 (en) 2007-03-28 2008-03-13 Antioxidant blends for fatty acid methyl esters (biodiesel)
CN200880010251A CN101688137A (zh) 2007-03-28 2008-03-13 脂肪酸甲酯(生物柴油)的抗氧化剂混合物
JP2010501053A JP2010522809A (ja) 2007-03-28 2008-03-13 脂肪酸メチルエステル（バイオディーゼル）のための抗酸化物質混合物
BRPI0809615A BRPI0809615A8 (pt) 2007-03-28 2008-03-13 Misturas antioxidantes para ésteres metílicos de ácido graxo (biodiesel)
US12/593,383 US20100107481A1 (en) 2007-03-28 2008-03-13 Antioxidant blends for fatty acid methyl esters (biodiesel)
EP08732069A EP2137283A1 (en) 2007-03-28 2008-03-13 Antioxidant blends for fatty acid methyl esters (biodiesel)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US90855107P 2007-03-28 2007-03-28
US90854607P 2007-03-28 2007-03-28
US60/908,546 2007-03-28
US60/908,551 2007-03-28

Publications (1)

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WO2008121526A1 true WO2008121526A1 (en) 2008-10-09

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US (1) US20100107481A1 (pt)
EP (1) EP2137283A1 (pt)
JP (1) JP2010522809A (pt)
KR (1) KR20100015881A (pt)
CN (1) CN101688137A (pt)
AU (1) AU2008232984A1 (pt)
BR (1) BRPI0809615A8 (pt)
CA (1) CA2681753A1 (pt)
RU (1) RU2009139760A (pt)
TW (1) TW200848502A (pt)
WO (1) WO2008121526A1 (pt)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010097640A1 (en) 2009-02-26 2010-09-02 Dorivale Holdings Limited Biodiesel containing non-phenolic additives and thereby possessing enhanced oxidative stability and low acid number
US20120233912A1 (en) * 2011-03-18 2012-09-20 Otkrytoe Aktsionernoe Obschestvo "Sterlitamaxky Neftekhimichesky Zavod" Antioxidant additive composition, a solution thereof, and a method for improving the storage stability of biodiesel fuel (variants)
US8367593B2 (en) 2009-10-02 2013-02-05 Exxonmobil Research And Engineering Company Method for improving the resistance to one or more of corrosion, oxidation, sludge and deposit formation of lubricating oil compositions for biodiesel fueled engines
US8680029B2 (en) 2009-10-02 2014-03-25 Exxonmobil Research And Engineering Company Lubricating oil compositions for biodiesel fueled engines
US9056268B2 (en) 2010-02-12 2015-06-16 Donaldson Company, Inc. Liquid filtration media, filter elements and methods

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8663344B2 (en) * 2007-08-24 2014-03-04 Albemarle Corporation Antioxidant blends suitable for use in biodiesels
US20110023351A1 (en) * 2009-07-31 2011-02-03 Exxonmobil Research And Engineering Company Biodiesel and biodiesel blend fuels
CN105985865B (zh) * 2015-02-02 2019-07-05 中国石油天然气股份有限公司 一种非食用动植物油的储存方法
CN106367138B (zh) * 2016-10-29 2018-04-17 重庆众商众信科技有限公司 一种抗氧化耐腐蚀型清洁燃料的制备方法
CN114436886B (zh) * 2022-01-12 2023-07-21 烟台新特路新材料科技有限公司 一种长链酰胺类化合物及其应用和复合润滑剂及制备方法

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US20100107481A1 (en) 2010-05-06
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TW200848502A (en) 2008-12-16
CN101688137A (zh) 2010-03-31
BRPI0809615A8 (pt) 2017-02-21
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CA2681753A1 (en) 2008-10-09

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