WO2017054921A1 - Compositions d'antioxydants stables au stockage contenant de l'acide ascorbique - Google Patents

Compositions d'antioxydants stables au stockage contenant de l'acide ascorbique Download PDF

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WO2017054921A1
WO2017054921A1 PCT/EP2016/001608 EP2016001608W WO2017054921A1 WO 2017054921 A1 WO2017054921 A1 WO 2017054921A1 EP 2016001608 W EP2016001608 W EP 2016001608W WO 2017054921 A1 WO2017054921 A1 WO 2017054921A1
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cas
composition
fatty acid
formula
antioxidant
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Axel Ingendoh
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Inachem Gmbh
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Priority to DE112016004456.9T priority Critical patent/DE112016004456T5/de
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    • C—CHEMISTRY; METALLURGY
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    • 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
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    • C10L1/188—Carboxylic acids; metal salts thereof
    • C10L1/1881—Carboxylic acids; metal salts thereof carboxylic group attached to an aliphatic carbon atom
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    • C10L1/188—Carboxylic acids; metal salts thereof
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    • C10L1/00—Liquid carbonaceous fuels
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    • C10L1/18—Organic compounds containing oxygen
    • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
    • C—CHEMISTRY; METALLURGY
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    • C10L1/00—Liquid carbonaceous fuels
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    • 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
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    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10L1/00—Liquid carbonaceous fuels
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    • C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
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    • C10L2200/00—Components of fuel compositions
    • C10L2200/04—Organic compounds
    • C10L2200/0461—Fractions defined by their origin
    • C10L2200/0469—Renewables or materials of biological origin
    • C10L2200/0476—Biodiesel, i.e. defined lower alkyl esters of fatty acids first generation biodiesel
    • C—CHEMISTRY; METALLURGY
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    • C10L2230/00—Function and purpose of a components of a fuel or the composition as a whole
    • C10L2230/08—Inhibitors
    • C10L2230/081—Anti-oxidants
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10L2300/00—Mixture of two or more additives covered by the same group of C10L1/00 - C10L1/308
    • C10L2300/20—Mixture of two components

Definitions

  • the present invention relates to storage-stable compositions comprising ascorbic acid and an antioxidant, and preferably a suitable solvent, to the use of the composition for improving the oxidation resistance of fatty acid esters such as biodiesel, as well as to compositions comprising a fatty acid ester and the storage-stable composition.
  • Liquid formulations of phenolic antioxidants used as additives to improve the oxidation stability of e.g. biodiesel are e.g. disclosed in US 8,075,804 and EP 2,896,682.
  • WO 2007/062304 discloses a composition comprising biodiesel, which may include more than one antioxidant wherein the antioxidants may be phenolic antioxidants, as well as non-phenolic antioxidants.
  • the antioxidants may be phenolic antioxidants, as well as non-phenolic antioxidants.
  • fatty acids of ascorbic acid may be used as non-phenolic antioxidants.
  • WO 2007/102948 discloses a composition containing phenolic antioxidant solutions. This application further discloses compositions containing both biodiesel and at least one antioxidant concentrate solution and blended fuel compositions containing both biodiesel blended with other fuels.
  • phenolic antioxidants are for example BHT (CAS no. 128-37-0), TBHQ (CAS no. 1948-33-0), BKF (CAS no. 1 19-47-1), TBC (CAS no. 98-29-3), propyl gallate (CAS no. 121-79-9), gallic acid (CAS no. 149-91-7), pyrogallol (CAS no. 87-66-1), hydroquinone (CAS no. 123-31- 9) and pyrocatechol (CAS no. 120-80-9).
  • BHT CAS no. 128-37-0
  • TBHQ CAS no. 1948-33-0
  • BKF CAS no. 1 19-47-1
  • TBC CAS no. 98-29-3
  • propyl gallate CAS no. 121-79-9
  • gallic acid CAS no. 149-91-7
  • pyrogallol CAS no. 87-66-1
  • hydroquinone CAS no. 123-31-9
  • pyrocatechol
  • Liquid formulations of phenolic antioxidants used as additives to improve the oxidation stability of oils and fats used in human and animal nutrition are e.g. disclosed in WO 2004/090062.
  • aminic antioxidants are sensitive to oxidation by atmospheric oxygen.
  • compositions of antioxidants in which this loss of effectiveness by oxidation with atmospheric oxygen during storage does not take place or occurs comparatively slowly.
  • Such formulations could then be advantageously used as additives to improve the oxidative stability of fatty acid esters, preferably fatty acid esters such as biodiesel.
  • compositions may be used for improving the oxidation resistance of fatty acid esters such as preferably biodiesel.
  • the invention relates to the following items:
  • composition comprising at least ascorbic acid, an antioxidant and a glycerol acetal or glycerol ketal of the general Formula 1
  • Ri and R 2 are independently hydrogen or CMO - alkyl, or R-i and R 2 together form a carbon chain having from 2 to 5 carbon atoms; wherein said antioxidant is a phenolic antioxidant or an aminic antioxidant, or a mixture of a phenolic antioxidant and an aminic antioxidant.
  • composition of item 1 wherein the compound of Formula 1 is isopropylidene glycerol (CAS No. 100-79-8).
  • Composition of item 1 or 2 further comprising one or more of: water; an alcohol of the general formula R3-OH, wherein R3 is a Ci.io - alkyl group; or a glycol or glycol ether of the general Formula 2,
  • Formula 2 wherein R 4 , R 5 , R 6 and R 7 are independently H, a CMO - alkyl, phenyl or benzyl, and n is an integer from 0 to 100.
  • Composition according to any one of items 1 to 4 wherein the composition comprises ascorbic acid and the compound of Formula 1 in a weight ratio of from 1 :50 to 1 :1 ,000.
  • composition according to any one of items 1 to 5 wherein the composition comprises said antioxidant and the compound of Formula 1 in a weight ratio of from 1 :0.25 to 1 :10.
  • Composition according to any one of items 3 to 6 comprising a mixture of a glycerol acetal or glycerol ketal of the Formula 1 and a glycol ether of the Formula 2 in any desired mixing ratio.
  • composition according to item 8 wherein the composition comprises TBHQ.
  • composition according to item 9 wherein the composition comprises hydroquinone.
  • said aminic antioxidant is selected from the group consisting of: N-(1 ,3-dimethylbutyl)-N'-phenyl-p- phenylenediamine (CAS no.
  • N-isopropyl-N'-phenyl-p-phenylenediamine (CAS No. 101-72-4), N,N-di-sec-butyl-p-phenylendiamine (CAS no. 101-96-2), N'- bis(1 ,4-dimethylpentyl)-p-phenylendiamine (CAS no. 003081-14-9), N-isopropyl-N'- phenyl-p-phenylenediamine (CAS no. 101 -72-4), N-(1 ,3-dimethylbutyl)-N'-phenyl-p- phenylenediamine (CAS no.
  • composition according to any one of items 1 to 11 further comprising one or more compounds selected from the group consisting of: dyes; inorganic or organic acids, in particular citric acid; heavy metal inhibitors, in particular an aryltriazole or a salicylidendiamine; and biocides.
  • composition comprising at least one fatty acid ester and a composition as in any of items 1 to 12.
  • Composition of item 16 wherein the fatty acid ester is a fatty acid methyl ester
  • Composition of item 16 or 17, wherein the fatty acid is a biodiesel.
  • the invention further relates to the following items: Composition comprising at least ascorbic acid, an aminic antioxidant and a glycol or glycol ether of the general Formula 2,
  • Composition of item 1 further comprising one or more of: water; an alcohol of the general formula R 3 -OH, wherein R 3 is a Ci -10 - alkyl group; or a glycerol acetal or glycerol ketal of Formula 1
  • Formula 1 wherein and R 2 are independently hydrogen or C-i -10 - alkyl, or Ri and R 2 together form a carbon chain having 2 to 5 carbon atoms.
  • Composition according to any one of items 1 to 3 wherein the composition comprises ascorbic acid and the compound of Formula 2 in a weight ratio of from 1 :50 to 1 :1 ,000.
  • composition according to any one of items 1 to 4 wherein the composition comprises said antioxidant and the compound of Formula 2 in a weight ratio of from 1 :0.25 to 1 :10.
  • Composition according to any one of items 2 to 5 comprising a mixture of a glycerol acetal or glycerol ketal of the Formula 1 and a glycol ether of the Formula 2 in any desired mixing ratio.
  • Composition according to one of items 1 to 6 wherein said aminic antioxidant is selected from the group consisting of: N-(1 ,3-dimethylbutyl)-N'-phenyl-p- phenylenediamine (CAS no. 793-24-8), N-isopropyl-N'-phenyl-p-phenylenediamine (CAS no.
  • N,N-di-sec-butyl-p-phenylendiamine (CAS no. 101-96-2), N'- bis(1 ,4-dimethylpentyl)-p-phenylendiamine (CAS no. 003081-14-9), N-isopropyl-N'- phenyl-p-phenylenediamine (CAS no. 101 -72-4), N-(1 ,3-dimethylbutyl)-N'-phenyl-p- phenylenediamine (CAS no. 128-37-0), and N,N'-di-sec-butyl-p-phenylenediamine (CAS no. 101 -96-2), or two or more thereof.
  • Composition according to any one of items 1 to 7, further comprising one or more compounds selected from the group consisting of: dyes; inorganic or organic acids, in particular citric acid; heavy metal inhibitors, in particular an aryltriazole or a salicylidendiamine; and biocides.
  • the invention further relates to the following items: Composition comprising at least ascorbic acid, a phenolic antioxidant and a first and a second solvent, said first solvent is selected from water or an alcohol of the general formula R 3 -OH, wherein R 3 is a Ci -10 - alkyl group, or a mixture of water and alcohol; and the second solvent is selected from a glycerol acetal or glycerol ketal of the general Formula 1
  • R 2 are independently hydrogen or Ci - 0 - alkyl, or R and R 2 together form a carbon chain having 2 to 5 carbon atoms, or a glycol or glycol ether of the general Formula 2,
  • Composition according to item 1 or 2 wherein the composition comprises ascorbic acid and water in a weight ratio of from 1 :1 to 1 :5.
  • Composition according to any one of items 1 to 3 wherein the composition comprises ascorbic acid and an alcohol in a weight ratio of 1 :1 to 1 :5.
  • the composition according to item 4 wherein the alcohol is selected from methanol, ethanol or isopropanol, or a mixture of two or three thereof.
  • the phenolic antioxidant is selected from the group consisting of: BHT (CAS no. 128-37-0), TBHQ (CAS no. 1948-33-0), BKF (CAS no. 119-47-1), TBC (CAS no. 98-29-3), propyl gallate (CAS no. 121-79-9), gallic acid (CAS no. 149-91-7), pyrogallol (CAS no. 87-66-1 ), hydroquinone (CAS no. 123-31-9), catechol (CAS no. 120-80-9), bisphenol A (CAS no. 80-05-7), or two or more thereof.
  • composition comprising at least one fatty acid ester and a composition as in any of items 1 to 8.
  • composition of item 1 wherein the fatty acid ester is a biodiesel.
  • the invention relates to a method of improving the oxidation resistance of a biodiesel, comprising step (C):
  • C contacting biodiesel with a composition comprising ascorbic acid and a phenolic antioxidant or an aminic antioxidant, or a phenolic antioxidant and an aminic antioxidant; or use of a composition comprising ascorbic acid and a phenolic antioxidant or an aminic antioxidant, or a phenolic antioxidant and an aminic antioxidant for improving the oxidation resistance of a biodiesel.
  • composition according to the invention it is possible with the composition according to the invention, not only to reduce or prevent the sensitivity of phenolic antioxidants to oxidation, but also to bring both the highly hydrophilic ascorbic acid as well as the very hydrophobic (lipophilic) phenolic antioxidant in solution and to keep the compounds dissolved.
  • This is due to the selection of the solvent, i.e. the glycerol acetal or ketal of Formula 1 as used in the composition according to the first aspect, the glycol or glycol ether of Formula 2 as defined in the composition as used according to the second aspect, or the solvent combination as defined in the composition according to the third aspect.
  • This is extremely important for the application. This applies even if the composition according to the invention is used for the oxidative stabilization of fatty acid esters, preferably of biodiesel.
  • the active ingredient content of the phenolic antioxidant remains also stable over a long time. There is little or even no oxidation in the presence of air upon storage. This becomes also apparent from a composition containing, for example, hydroquinone, which discolors yellow or red when no ascorbic acid is added. This discoloration can be suppressed by the addition of ascorbic acid.
  • composition of the present invention is generally liquid, even at low storage temperatures ranging from 0 °C to 4 °C and does also not tend to crystallize immediately. This property is particularly advantageous for use in fatty acid esters such as biodiesel, since the products can be transported and stored at low temperatures without increased expense in terms of heating or isolating.
  • the invention relates to a composition
  • a composition comprising at least ascorbic acid, an antioxidant and a glycerol acetal or glycerol ketal of the general Formula 1
  • R- ⁇ and R 2 are independently hydrogen or C 1-10 - alkyl, or R- ⁇ and R 2 together form a carbon chain having 2 to 5 carbon atoms; wherein said antioxidant is a phenolic antioxidant or an aminic antioxidant, or a mixture of a phenolic antioxidant and an aminic antioxidant.
  • the invention relates to a composition
  • a composition comprising at least ascorbic acid, an aminic antioxidant and a glycol or glycol ether of the general Formula 2,
  • R 4 , R 5 , R 6 and R 7 are independently H, C 1-10 - alkyl, phenyl or benzyl, and n is an integer of from 0 to 100.
  • the invention relates to a composition
  • a composition comprising at least ascorbic acid, a phenolic antioxidant and a first and a second solvent
  • said first solvent is selected from water or an alcohol of the general formula R 3 -OH, wherein R 3 is a Ci -10 - alkyl group, or a mixture of water and alcohol
  • the second solvent is selected from a glycerol acetal or glycerol ketal of the general Formula 1
  • R- ⁇ and R 2 are independently hydrogen or C -10 - alkyl, or R ⁇ and R 2 together form a carbon chain having 2 to 5 carbon atoms, or a glycol or glycol ether of the general Formula 2,
  • ascorbic acid is used synonymously with the term “vitamin C”.
  • vitamin C vitamin C
  • the ascorbic acid (CAS no. 50-81 -7) is preferably used as L-ascorbic acid.
  • the composition contains neither salts of ascorbic acid nor the reaction products of fatty acids with ascorbic acid.
  • phenolic antioxidant means any phenol which can slow down or prevent the oxidation of a chemical compound such as preferably a fatty acid ester.
  • the phenolic antioxidant is selected from the group consisting of: BHT (2,6-di-tert-butyl-4-methylphenol; 2,6-bis(1 ,1 -dimethylethyl)-4-methylphenol; CAS no. 128-37-0), TBHQ (tert-butylhydroquinone; CAS no. 1948-33-0), BKF (6,6'-di-tert-butyl- 2,2'-methylenedi-cresol; CAS no. 1 19-47-1 ), TBC (p-tert-butylcatechol; CAS no. 98-29- 3), propyl gallate (CAS no. 121-79-9), gallic acid (CAS no.
  • BHT 2,6-di-tert-butyl-4-methylphenol
  • 2,6-bis(1 ,1 -dimethylethyl)-4-methylphenol CAS no. 128-37-0
  • TBHQ tert-butylhydroquinone
  • the phenolic antioxidant is a disubstituted or trisubstituted hydroxy-substituted benzene.
  • the composition comprises TBHQ.
  • the composition comprises TBHQ and hydroquinone.
  • the weight ratio of TBHQ and hydroquinone ranges from 1 :5 to 5:1 .
  • aminic antioxidant means any aromatic, aliphatic or cyclic amine which can slow down or prevent the oxidation of a chemical compound such as preferably a fatty acid ester.
  • said aminic antioxidant is selected from the group consisting of: N- (1 ,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine (CAS no. 793-24-8), N-isopropyl-N'- phenyl-p-phenylenediamine (CAS No. 101-72-4), N,N-di-sec-butyl-p-phenylendiamine (CAS no.
  • N'-bis(1 ,4-dimethylpentyl)-p-phenylendiamine (CAS no. 003081-14- 9)
  • N-isopropyl-N'-phenyl-p-phenylenediamine (CAS no. 101-72-4)
  • N-(1 ,3- dimethylbutyl)-N'-phenyl-p-phenylenediamine (CAS no. 128-37-0)
  • N,N'-di-sec-butyl- p-phenylenediamine CAS no. 101-96-2
  • the amount of ascorbic acid is a range of from 0.1 to 5 wt.-%.
  • the composition comprises ascorbic acid and the compound of Formula 1 in a weight ratio of from 1 :50 to 1 :1 ,000, or 1 :100 to 1 :800, provided the composition comprises ascorbic acid and said compound of Formula 1.
  • the composition comprises said antioxidant and the compound of Formula 1 in a weight ratio of from 1 :0.25 to 1 :10, or 1 :0.5 to 1 :5, provided the composition comprises ascorbic acid and said compound of Formula 1.
  • the composition comprises ascorbic acid and the compound of Formula 2 in a weight ratio of from 1 :50 to 1 :1 ,000, or 1 :100 to 1 :800, provided the composition comprises ascorbic acid and said compound of Formula 2.
  • the composition comprises said antioxidant and the compound of Formula 2 in a weight ratio of from 1 :0.25 to 1 :10, or 1 :0.5 to 1 :5, provided the composition comprises ascorbic acid and said compound of Formula 2.
  • the composition comprises a mixture of a glycerol acetal or glycerol ketal of the Formula 1 and a glycol ether of the Formula 2 in any desired mixing ratio, provided the composition comprises a compound off Formula 1 and Formula 2.
  • the composition comprises ascorbic acid and water in a weight ratio of 1 :1 to 1 :5, provided the composition comprises water.
  • the composition comprises ascorbic acid and the alcohol R 3 -OH in a weight ratio of 1 :1 to 1 :5, provided the composition comprises an alcohol.
  • the alcohol is selected preferably from methanol, ethanol or isopropanol.
  • the glycerol acetals or glycerol ketals of Formula 1 are known or can be prepared by known processes by reacting glycerol with the respective aldehydes or ketones.
  • the glycerol acetals or glycerol ketals of Formula 1 can also be present as structurally isomeric 6-membered ring, wherein the alcohol function is acetalized or ketalized in position 1 and 3 of glycerol.
  • Technical products are usually present as mixtures of both structural isomers in varying proportions.
  • the composition comprises isopropylidene glycerol, provided the composition comprises a compound of Formula 1.
  • C 1-i0 - alkyl residue as used herein, e.g. in connection with a compound of Formula 1 or an alcohol of the general formula R3-OH, means a straight, a branched, a cyclic or a cycloaliphatic alkyl residue.
  • glycols and glycol ethers of Formula 2 are also known and can be prepared by known methods.
  • Suitable products of Formula 2 are preferably ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monobutyl ether, ethylene glycol monophenyl ether, ethylene glycol monohexyl ether, ethylene glycol monobenzyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-butyl ether, diethylene glycol mono-n-hexyl ether, propylene glycol monomethyl ether, propylene glycol monobutyl ether, propylene glycol monohexylether, dipropylene glycol monomethyl ether, dipropylene glycol monobutyl ether, dipropylene glycol monohexylether, polyethylene glycol ether and polypropylene glycol ether.
  • composition of the invention may also comprise further compounds.
  • compounds are selected from the group: dyes, inorganic or organic acids, in particular citric acid, heavy metal inhibitors, in particular aryltriazoles and salicylidendiamines, and biocides.
  • fat-soluble dyes are used as dyes, from which the Macrolex® types of company Lanxess are particularly suitable.
  • the inventive composition may be prepared by mixing the components, if necessary applying heat.
  • the invention further relates to the use of a composition as defined in the first aspect, second or third aspect to improve the oxidative stability of fatty acid esters.
  • the invention relates to a method of improving the oxidation resistance of a fatty acid ester, comprising step (C):
  • fatty acid ester means esters of fatty acids preferably having from 10 to 40 carbon atoms with any mono- or polyhydric alcohol.
  • the fatty acid ester is a biodiesel.
  • biodiesel refers to a fatty acid methyl ester, obtained by alkaline or acid transesterification of vegetable oils such as rapeseed oil, soya bean oil or palm oil with methanol.
  • biodiesel also includes fatty acid methyl esters obtained from used vegetable oils and fats and animal oils and fats.
  • biodie encompasses C 8- 36 fatty acid methyl esters.
  • said fatty acid glycerides may be animal fatty acid glycerides.
  • An example is tallow such as beef tallow or pork tallow.
  • said fatty acid glycerides may be vegetable fatty acid glyce rides.
  • Examples are rapeseed oil, soy bean oil, sunflower oil, palm oil, coconut oil, or algae oil
  • said fatty acid glycerides are waste oils and fats, i.e. oils and fats which are not suitable for human consumption.
  • the invention further relates to a composition comprising at least a fatty acid ester and a composition as defined in the first aspect, the second or the third aspect.
  • the fatty acid ester is a methyl ester.
  • the fatty acid ester is a biodiesel.
  • the inventive composition containing a fatty acid ester can be prepared by mixing the fatty acid ester, which preferably is liquid at room temperature, with the composition in as defined in the first aspect, the second aspect or the third aspect, if necessary applying heat.
  • a composition produced in this manner could be stained by adding, for example, 500 ppm Macrolex® Green (Fa. Lanxess).
  • Example 2
  • a composition produced in this manner could be stained by adding, for example, 500 ppm Macrolex® Green (Fa. Lanxess).
  • a composition produced in this manner could be stained by adding, for example, 500 ppm Macrolex® Green (Fa. Lanxess).
  • compositions containing L-ascorbic acid were significantly longer storage stable than the same formulation without L-ascorbic acid.
  • the formulation according to Example 1 when stored in an air-permeable bottle consisting of polypropylene or polyethylene, after 6 months at temperatures of 20 to 25 °C, still a content of 20 % of hydroquinone could be found since the preparation of the composition.
  • compositions according to the invention were further evidenced by means of the following tests:
  • ascorbic acid provides for a synergistic effect. This is shown in Table 3.
  • Table 6 lists examples with an aminic antioxidant.
  • the aminic antioxidants were distilled prior to the formulation.
  • the compositions were prepared according to the method of Example 1.

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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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)
  • Fats And Perfumes (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne des compositions comprenant de l'acide ascorbique et un antioxydant phénolique ou aminique, de préférence dans un solvant approprié, pour améliorer la résistance à l'oxydation d'un ester d'acide gras, tel qu'un ester méthylique d'acide gras (biodiesel).
PCT/EP2016/001608 2015-09-30 2016-09-26 Compositions d'antioxydants stables au stockage contenant de l'acide ascorbique WO2017054921A1 (fr)

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Cited By (1)

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US12091624B2 (en) 2021-07-06 2024-09-17 Happyfuel, Llc Fuel stabilizer

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US3752832A (en) * 1970-09-08 1973-08-14 Kongo Yakuhin K K Process for anti oxidation against lipid
US20040139649A1 (en) * 2002-11-13 2004-07-22 Axel Ingendoh Process for increasing the storgage stability of biodiesel and the use of 2,4-di-tert-butylhydroxytoluene for increasing the storage stability of biodiesel
WO2004090062A2 (fr) 2003-04-04 2004-10-21 Kemin Industries, Inc. Formulations liposolubles contenant des melanges d'antioxydants
WO2007062304A2 (fr) 2005-11-23 2007-05-31 Novus International, Inc. Compositions combustibles de biodiesel presentant une meilleure tenue a l'oxydation
WO2007102948A2 (fr) 2006-02-03 2007-09-13 Eastman Chemical Company Compositions antioxydantes utiles dans des compositions à base de biodiesel et d'autres d'esters d'acides gras et d'acides
EP2896682A1 (fr) 2014-01-17 2015-07-22 LANXESS Deutschland GmbH Biodiesel stabilisé contre l'oxydation

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US3752832A (en) * 1970-09-08 1973-08-14 Kongo Yakuhin K K Process for anti oxidation against lipid
US20040139649A1 (en) * 2002-11-13 2004-07-22 Axel Ingendoh Process for increasing the storgage stability of biodiesel and the use of 2,4-di-tert-butylhydroxytoluene for increasing the storage stability of biodiesel
WO2004090062A2 (fr) 2003-04-04 2004-10-21 Kemin Industries, Inc. Formulations liposolubles contenant des melanges d'antioxydants
WO2007062304A2 (fr) 2005-11-23 2007-05-31 Novus International, Inc. Compositions combustibles de biodiesel presentant une meilleure tenue a l'oxydation
WO2007102948A2 (fr) 2006-02-03 2007-09-13 Eastman Chemical Company Compositions antioxydantes utiles dans des compositions à base de biodiesel et d'autres d'esters d'acides gras et d'acides
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US12091624B2 (en) 2021-07-06 2024-09-17 Happyfuel, Llc Fuel stabilizer

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