US20070113467A1 - Biodiesel fuel compositions having increased oxidative stability - Google Patents

Biodiesel fuel compositions having increased oxidative stability Download PDF

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Publication number
US20070113467A1
US20070113467A1 US11/559,974 US55997406A US2007113467A1 US 20070113467 A1 US20070113467 A1 US 20070113467A1 US 55997406 A US55997406 A US 55997406A US 2007113467 A1 US2007113467 A1 US 2007113467A1
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oil
tert
antioxidant
ethoxy
trimethylquinoline
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Ibrahim Abou-Nemeh
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Novus International Inc
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Novus International Inc
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Assigned to NOVUS INTERNATIONAL, INC. reassignment NOVUS INTERNATIONAL, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: ABOU-NEMEH, IBRAHIM
Publication of US20070113467A1 publication Critical patent/US20070113467A1/en
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    • C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
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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
    • C10L1/1883—Carboxylic acids; metal salts thereof carboxylic group attached to an aliphatic carbon atom polycarboxylic acid
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    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/188—Carboxylic acids; metal salts thereof
    • C10L1/189—Carboxylic acids; metal salts thereof having at least one carboxyl group bound to an aromatic carbon atom
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    • C10L1/00—Liquid carbonaceous fuels
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    • C10L1/14—Organic compounds
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    • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
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    • C10L1/00—Liquid carbonaceous fuels
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    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
    • C10L1/1905—Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polycarboxylic acids
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    • C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
    • C10L1/2425—Thiocarbonic acids and derivatives thereof, e.g. xanthates; Thiocarbamic acids or derivatives thereof, e.g. dithio-carbamates; Thiurams
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    • C10L1/2633—Organic compounds containing phosphorus phosphorus bond to oxygen (no P. C. bond)
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Definitions

  • biodiesel is produced through the transesterifcation of vegetable oils, spent cooking oils, or animal fats.
  • Such methods typically include base catalyzed transesterification of the oil or fat with an alcohol, and direct acid catalyzed esterification of the oil or fat with methanol, conversion of the oil or fat to fatty acids, and then to alkyl esters with an acid catalyst.
  • the antioxidant may be a synthetic or natural antioxidants selected from the group comprising of Vitamin C and derivatives (ascorbic acid); Vitamin E and derivatives (tocopherols, tocotrienols, acetate); sage extract; eugenol; rosemary; flavonoids and derivatives (including catechins); phenolic acids and derivatives; 2-tert-butylhydroquinone (TBHQ); mixtures of TBHQ, glyceryl oleate, propylene glycol, vegetable oil, and citric acid such as TENOX 20® and TENOX 21® by the company Eastman Chemical Company; imidazolidinyl urea, quaternary ammoniums, diazolidinyl urea; erythorbic acid; sodium erythorbate, lactic acid, calcium ascorbate, sodium ascorbate, potassium ascorbate, ascorbyl stearate, erythorbin acid; sodium erythorbin; butyl
  • the antioxidant may be a water soluble antioxidants selected from the group comprising of ascorbic acid, sodium metabisulfite, sodium bisulfite, sodium thiosulfite, sodium formaldehyde sulfoxylate, isoascorbic acid, thioglyerol, thiosorbitol, thiourea, thioglycolic acid, cysteine hydrochloride, 1,4-diazobicyclo-(2,2,2)-octane, malic acid, fumaric acid, and licopene.
  • ascorbic acid sodium metabisulfite, sodium bisulfite, sodium thiosulfite, sodium formaldehyde sulfoxylate, isoascorbic acid, thioglyerol, thiosorbitol, thiourea, thioglycolic acid, cysteine hydrochloride, 1,4-diazobicyclo-(2,2,2)-octane, malic
  • R 1 , R 2 , R 3 and R 4 are independently selected from the group consisting of hydrogen and an alkyl group having from 1 to about 4 carbons;
  • R 5 is an alkoxy group having from 1 to about 4 carbons.
  • the substituted 1,2-dihydroquinoline will be 6-ethoxy-1,2-dihydro-2,2,4-trimethylquinoline having the formula: 6-ethoxy-1,2-dihydro-2,2,4-trimethylquinoline, commonly known as ethoxyquin, is sold under the trademark SANTOQUIN® or AGRADO®.
  • the present invention also encompasses salts of ethoxyquin and other compounds having formula (I). Ethoxyquin and other compounds having formula (I) may be purchased commercially from Novus International, Inc. or made in accordance with methods generally known in the art, for example, as detailed in U.S. Pat. No. 4,772,710, which is hereby incorporated by reference in its entirety.
  • the antioxidant of the present invention is an antioxidant mixture comprising at least two antioxidants as described in Part II(a).
  • the antioxidant mixture comprises a first antioxidant of substituted 1,2-dihydroquinoline compound of Formula (I) and a second antioxidant that does not have the Formula (I).
  • the second antioxidant may be any of the antioxidants described in Part II(a) above other than the antioxidant of Formula (I).
  • the antioxidant mixture may include at least three different antioxidants.
  • the combination may include four or more antioxidants.
  • suitable antioxidant mixtures are set-forth in Table A.
  • a preferred composition comprises 6-ethoxy-1,2-dihydro-2,2,4-trimethylquinoline (ethoxyquin) and 2-tert-butylhydroquinone.
  • Other preferred compositions comprise 6-ethoxy-1,2-dihydro-2,2,4-trimethylquinoline, as well as one or more of the following: 2-tert-butylhydroquinone, 3,4,5-trihydroxybenzoic acid n-propyl ester, 1,2,3-trihydroxybenzene, butylated hydroxyanisole, 2,6-Di-tert-Butyl-1-Hydroxy-4-Methylbenzene, alpha-tocopherol acetate, alpha-tocopherol, gamma-tocopherol, delta-tocopherol, dilauryl thiodipropinate, isopropyl 2-hydroxy-4-methylthio butanoate, propyl gallate, dodecyl gallate, gallic acid, octyl gallate
  • the antioxidant composition may further comprise a polar solvent.
  • the polar solvent solubilizes the water-soluble antioxidants.
  • Suitable examples of polar solvents include, but are not limited to, glycerol, isopropyl alcohol, ethyl alcohol, propylene glycol, erythritol, xylitol, sorbitol, maltitol, mannitol, water, polyol, or combinations thereof.
  • the polar solvent is glycerol.
  • the polar solvent is propylene glycol.
  • the concentration of the polar solvent will vary depending upon the combination of antioxidants in the composition. In general, the percent by volume of the polar solvent may range from about 5% to about 50%. The percent by volume of glycerol may be about 5%, 10%, 15%, 20%, or 25%. The percent by volume of propylene glycol may be about 5%, 10%, 15%, 20%, or 25%.
  • the antioxidant composition may further comprise a nonpolar solvent.
  • the nonpolar solvent solubilizes the lipid-soluble antioxidants, and helps make the antioxidant composition miscible in an oil or fat sample.
  • the nonpolar solvent is a biodiesel as described in Part I above.
  • Suitable examples of other nonpolar solvents include, but are not limited to, vegetable oils, monoglycerides, diglycerides, triglycerides, and combinations thereof.
  • the vegetable oil may be corn oil, soybean oil, canola oil, cottonseed oil, palm oil, peanut oil, safflower oil, and sunflower oil.
  • the monoglycerides and diglycerides may be isolated and distilled from vegetable oils, or the monoglycerides and diglycerides may be synthesized chemically via an esterification reaction.
  • the nonpolar solvent may be corn oil.
  • the nonpolar solvent may comprise corn oil and monoglycerides.
  • the concentration of the nonpolar solvent will vary depending upon the combination of antioxidants in the composition. In general, the percent by volume of the nonpolar solvent may range from about 5% to about 50%.
  • the percent by volume of monoglycerides may be 10%, 15%, 20%, or 25%.
  • the percent by volume of corn oil may be 5%, 10%, 15%, 20%, or 25%. In one embodiment, percent by volume of corn oil may be 15-25%. In another embodiment, the percent by volume of monoglycerides may be 15-20% and the percent by volume of corn oil may be about 5-10%.
  • the present invention is also directed to a fuel composition
  • a fuel composition comprising a biodiesel and an antioxidant mixture comprising at least two antioxidants and optionally, a polar solvent, a nonpolar solvent, and/or a petroleum based diesel.
  • the fuel composition comprises any of the biodiesels as described in Part I and an antioxidant mixture comprising at least two antioxidant as described in Part II of the specification above.
  • the fuel composition comprises a first antioxidant having Formula (I), a second antioxidant not having Formula (I), a polar solvent, and a nonpolar solvent, as described in Part II of the specification above, wherein the two solvents form a homogeneous liquid.
  • the nonpolar solvent is a biodiesel as described in Part I of the specification above.
  • the fuel composition comprises a biodiesel produced from soybean oil, a first antioxidant, preferably 6-ethoxy-1,2-dihydro-2,2,4-trimethylquinoline, a second antioxidant, preferably a mixture of natural mixed tocopherols, ascorbyl palmitate, propyl gallate, 2-tert-butylhydroquinone, and lecithin, and a second nonpolar solvent, preferably corn oil.
  • a first antioxidant preferably 6-ethoxy-1,2-dihydro-2,2,4-trimethylquinoline
  • a second antioxidant preferably a mixture of natural mixed tocopherols, ascorbyl palmitate, propyl gallate, 2-tert-butylhydroquinone, and lecithin
  • a second nonpolar solvent preferably corn oil.
  • the fuel composition comprises a biodiesel produced from soybean oil and an antioxidant mixture comprising about 40 ppm of 6-ethoxy-1,2-dihydro-2,2,4-trimethylquinoline, about 40 ppm of a mixture of Butylated Hydroxyanisole and 2,6-Di-tert-Butyl-1-Hydroxy-4-Methylbenzene, and about 50 ppm of 2-tert-butylhydroquinone.
  • the concentration of antioxidants will also vary in accordance with the oxidative stability desired for the fuel.
  • concentration of antioxidants will also vary in accordance with the oxidative stability desired for the fuel.
  • OSI Oxidative Stability Index
  • AOM Active Oxygen Method
  • ASTM D-2274 Standard Test Method for Oxidation Stability of Distillate Fuel oil
  • the ASTM Method measures the insolubles of fuels under specified oxidizing conditions at 95° C. In particular, the method calculates the total insoluble mass (mg/100 mL) as the sum of the filterable insolubles and the adherent insolubles. The calculations are further described in the examples.
  • a fuel composition comprising a biodiesel produced from yellow grease and 6-ethoxy-1,2-dihydro-2,2,4-trimethylquinoline has a total insoluble mass of 0.9 mg/mL, as shown in Example 3.
  • a fuel composition of the invention comprises a biodiesel and a petroleum based diesel wherein the fuel composition has improved oxidative stability.
  • the fuel composition comprises any of the composition of Table A and a petroleum based diesel fuel wherein the fuel composition has improved oxidative stability.
  • the fuel composition comprises any of the compositions of Table C and a petroleum based diesel fuel.
  • the method of increasing the oxidative stability of a fuel composition comprises contacting a biodiesel with an antioxidant mixture that increases the oxidative stability of the fuel.
  • the biodiesel fuel compositions of the invention may contain additional agents that enhance one or more characteristics of the fuel.
  • additional agents that enhance one or more characteristics of the fuel.
  • these additives may be particularly beneficial when the fuel composition comprises a biodiesel and a petroleum based diesel.
  • Suitable additives may include, but are not limited to, cetane improvers and/or ignition accelerator agent, corrosion inhibitors and/or metal deactivators, cold flow improvers, and the like, as described below.
  • hindered phenolic antioxidants that also exhibit a thermal stability effect include 2,6-di-t-butyl-4-methylphenol; 2,6-di-t-butylphenol; 2,2′-methylene-bis(6-t-butyl-4-methylphenol); n-octadecyl 3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate; 1,1,3-tris(3-t-butyl-6-methyl-4hydroxyphenyl)butane; pentaerythrityl tetrakis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate]; di-n-octadecyl(3,5-di-t-butyl-4-hydroxybenzyl)phosphonate; 2,4,6-tris(3,5-di-t-butyl-4-hydroxybenzyl)mesitylene; and tris(3,5-di-t-butyl-4-
  • thermal stabilizers include: pentaerythritol co-esters derived from pentaerythritol, (3-alkyl-4-hydroxyphenyl)-alkanoic acids and alkylthioalkanoic acids or lower alkyl esters of such acids which are useful as stabilizers of organic material normally susceptible to oxidative and/or thermal deterioration.
  • pentaerythritol co-esters derived from pentaerythritol, (3-alkyl-4-hydroxyphenyl)-alkanoic acids and alkylthioalkanoic acids or lower alkyl esters of such acids which are useful as stabilizers of organic material normally susceptible to oxidative and/or thermal deterioration.
  • U.S. Pat. No. 4,806,675 and U.S. Pat. No. 4,734,519 to Dunski, et al. hindered phenyl phosphites
  • Examples of compounds known in the art as providing some degree of both oxidation resistance and thermal stability include diphenylamines, dinaphthylamines, and phenylnaphthylamines, either substituted or unsubstituted, e.g., N,N′-diphenylphenylenediamine, p-octyldiphenylamine, p,p-dioctyldiphenylamine, N-phenyl-1-naphthylamine, N-phenyl-2-naphthylamine, N-(p-dodecyl)phenyl-2-naphthylamine, di-1-naphthylamine, and di-2naphthylamine; phenothazines such as N-alkylphenothiazines; imino(bisbenzyl); and hindered phenols such as 6-(t-butyl)phenol, 2,6-di-
  • the oxidation instabilities normally associated with vegetable oils are generally due to a high content of linoleic and linolenic fatty acids. Moreover, the degree of unsaturation (or double bonds) in the fatty acids in vegetable oils correlates with sensitivity to oxidation, with a greater number of double bonds resulting in a material more sensitive to and prone to rapid oxidation.
  • Esters of C20 or higher acids are preferred, e.g., gondoic acid, eicosadienoic acid, eicosatrienoic acid, eicosatetraenoic acid, eicosapentanoic acid, arachidic acid, arachidonic acid, behenic acid, erucic acid, docosapentanoic acid, docosahexanoic acid, or ligniceric acid.
  • an alkylated aromatic may be utilized in the fuel compositions of the invention.
  • Alkylated aromatics are formed by the reaction of olefins or alkyl halides with aromatic compounds, such as benzene.
  • Thermal stability is similar to that of polyalphaolefins, and additives are typically used to provide oxidative stability.
  • Polyalkylene glycols are polymers of alkylene oxides exhibiting good thermal stability, but are typically used in combination with additives to provide oxidation resistance.
  • Phosphate esters are synthesized from phosphorus oxychloride and alcohols or phenols and also exhibit good thermal stability.
  • any of a number of different types of suitable detergent additives can be included in diesel fuel compositions of various embodiments.
  • These detergents include succinimide detergent/dispersants, long-chain aliphatic polyamines, and long-chain Mannich bases.
  • Use of fuel-soluble long chain aliphatic polyamines as induction cleanliness additives in distillate fuels is described, for example, in U.S. Pat. No. 3,438,757.
  • Use of fuel-soluble Mannich base additives formed from a long chain alkyl phenol, formaldehyde (or a formaldehyde precursor thereof), and a polyamine to control induction system deposit formation in internal combustion engines is described, for example, in U.S. Pat. No. 4,231,759.
  • the detergent additives for example, are effective in reducing carburetor deposits and fuel injector deposits.
  • a particularly effective amine is oleyl amine obtainable from Akzo Nobel Surface Chemistry LLC of Chicago, Ill. under the name ARMEEN® O or ARMEEN® OD.
  • Other suitable amines which are generally mixtures of aliphatic amines include ARMEEN® T and ARMEEN® TD, the distilled form of ARMEEN® T which contains a mixture of 0-2% of tetradecyl amine, 24% to 30% of hexadecyl amine, 25% to 28% of octadecyl amine and 45% to 46% of octadecenyl amine.
  • ARMEEN® T and ARMEEN® TD are derived from tallow fatty acids.
  • Lauryl amine is also suitable, as is ARMEEN® 12D obtainable from the supplier indicated above. This product is about 0-2% of decylamine, 90% to 95% dodecylamine, 0-3% of tetradecylamine and 0-1% of octadecenylamine.
  • Amines of the types indicated to be useful are well known in the art and may be prepared from fatty acids by converting the acid or mixture of acids to its ammonium soap, converting the soap to the corresponding amide by means of heat, further converting the amide to the corresponding nitrile and hydrogenating the nitrile to produce the amine.
  • AGRADO R® refers to a form of ethoxyquin and TBHQ.
  • Acid Number refers to the milligrams of KOH required in tests to neutralize all the acidic constituents present in a 1 gram sample of fuel product. This property is often used to indicate the extent of contamination or oxidation of fuels.
  • Induction time stands one the measure of the resistance to oxidation.
  • PETGUARD® refers to an antioxidant mixture of BHA, BHT, and vegetable oil.
  • PV peroxide value
  • PPM parts per million
  • yellow grease refers to waste grease from restaurants and low-grade fats from rendering plants; yellow grease is a mixture of vegetable oils and animal fats.
  • a stream of air is passed through a lipid sample and the effluent air from the lipid sample is bubbled through a test vessel containing deionized water, whose conductivity is continuously monitored.
  • deionized water whose conductivity is continuously monitored.
  • conductivity tubes were filled with 50 ml of deionized water and probes were attached. The conductivity of the water in the tubes was verified to be constant with a reading of 25 ⁇ S/cm or less. Twenty ml of (liquefied) sample ( ⁇ antioxidant) was placed directly into the bottom of the reaction tube.
  • the standard test method for oxidation stability of distillate fuel oil (ASTM D2274; accelerated method) was also used to rate the effectiveness of the different antioxidant blends. This method measures the filterable insolubles, the adherent insolubles, and the total insolubles after an accelerated oxidative process.
  • ASTM D2274 oxidation stability of distillate fuel oil
  • This method measures the filterable insolubles, the adherent insolubles, and the total insolubles after an accelerated oxidative process.
  • 400 ml of fuel was filtered through a cellulose ester surfactant-free membrane filter having a nominal pore size of 0.8 ⁇ m.
  • a clean oxygen delivery tube was placed in each clean oxidation test cell, and 350 ml of the filtered fuel was added to the test cell.
  • the test cell was placed in a 95° C. heating bath, and oxygen was bubbled through the test sample at a rate of 3 I/h for 16 hr.
  • the tare mass of the blank (W 3 ) and sample (W 4 ) beakers were subtracted from the final mass (after evaporation) of the blank (W 5 ) and sample (W 6 ) beakers.
  • Antioxidant blends were tested and the filterable insolubles, adherent insolubles, and total insolubles were determined.
  • the following antioxidant blends were tested: 1-6, 1-8, 1-14, and 1-16 from Example 4 (see Table 4); 2-4 and 2-12 from Example 5 (see Table 5); and 3-12 from Example 6 (see Table 6).
  • Each blend was tested at 500 ppm, 1000 ppm, and 2000 ppm.
  • Controls included biodiesel, and biodiesel containing 1000 ppm of TBHQ or 1000 ppm of TENOX-21 (TNX21). The results are presented in Table 8. All of the antioxidant blends, with the exception of the lowest concentration of blend 3-12, reduced the amount of insolubles in the biodiesel.

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BRPI0618942A2 (pt) 2011-09-13

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