EP0626442A1 - Mit einem Stockpunkterniedrigtem behandelte Fettsäureester, als biologisch abbaubare Verbrennungsmotorkraftstoffe - Google Patents

Mit einem Stockpunkterniedrigtem behandelte Fettsäureester, als biologisch abbaubare Verbrennungsmotorkraftstoffe Download PDF

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Publication number
EP0626442A1
EP0626442A1 EP94303590A EP94303590A EP0626442A1 EP 0626442 A1 EP0626442 A1 EP 0626442A1 EP 94303590 A EP94303590 A EP 94303590A EP 94303590 A EP94303590 A EP 94303590A EP 0626442 A1 EP0626442 A1 EP 0626442A1
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Prior art keywords
carbon atoms
oil
parts
ester
composition
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EP94303590A
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English (en)
French (fr)
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EP0626442B1 (de
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Kasturi Lal
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Lubrizol Corp
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Lubrizol Corp
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Definitions

  • a natural oil comprising animal fat or vegetable oils is reacted with an alcohol to obtain the transesterified esters.
  • These natural oils include triglycerides of the formula wherein R1, R2 and R3 are aliphatic hydrocarbyl groups containing from about 6 to about 24 carbon atoms.
  • the term "hydrocarbyl group” as used herein and throughout this specification and claims denotes a radical having a carbon atom directly attached to the remainder of the molecule.
  • the aliphatic hydrocarbyl groups include the following:
  • Example A-9 The procedure of Example A-9 is essentially followed except that beef tallow oil is utilized instead of cottonseed oil.
  • the product obtained is the transesterified ethyl ester of beef tallow oil.
  • Example A-10 The procedure of Example A-10 is essentially followed except that menhaden oil is utilized instead of corn oil.
  • the product obtained is the transesterified n-butyl ester of menhaden oil.
  • low molecular weight groups include methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, sec-butyloxy, iso-butyloxy, n-pentyloxy, neo-pentyloxy, n-hexyloxy, cyclohexyloxy, xyxlopentyloxy, 2-methyl-butyl-1-oxy, 2,3-dimethyl-butyl-1-oxy, etc.
  • alkoxy groups of suitable size comprise the preferred high and low molecular weight ester groups.
  • Polar substituents may be present in such ester groups. Examples of polar substituents are chloro, bromo, ether, nitro, etc.
  • the ratio is from about 2.5:1 to about 5:1. More than one high molecular weight alcohol or low molecular weight alcohol may be used in the process; so also may be used commercial alcohol mixtures such as the so-called Oxoalcohols which comprise, for example mixtures of alcohols having from 8 to about 24 carbon atoms.
  • a particularly useful class of alcohols are the commercial alcohols or alcohol mixtures comprising decylalcohol, dodecyl alcohol, tridecyl alcohol, tetradecyl alcohol, pentadecyl alcohol, hexadecyl alcohol, heptadecyl alcohol and octadecyl alcohol.
  • Other alcohols useful in the process are illustrated by those which, upon esterification, yield the ester groups exemplified above.
  • Example (B-10) The following example is similar to Example (B-10) but employs different alcohols and different levels in a different order of addition.
  • Component (B) may be at least one hydrocarbon-soluble acrylate polymer of the formula wherein R5 is hydrogen or a lower alkyl group containing from 1 to about 4 carbon atoms, R6 is a mixture of alkyl, cycloalkyl or aromatic groups containing from about 4 to about 24 carbon atoms, and x is an integer providing a weight average molecular weight (Mw) to the acrylate polymer of about 5000 to about 1,000,000.
  • R5 is hydrogen or a lower alkyl group containing from 1 to about 4 carbon atoms
  • R6 is a mixture of alkyl, cycloalkyl or aromatic groups containing from about 4 to about 24 carbon atoms
  • x is an integer providing a weight average molecular weight (Mw) to the acrylate polymer of about 5000 to about 1,000,000.
  • alkyl groups R6 which may be included in the polymers of the present invention include, for example, n-butyl, octyl, decyl, dodecyl, tridecyl, octadecyl, hexadecyl, octadecyl.
  • the mixture of alkyl groups can be varied so long as the resulting polymer is hydrocarbon-soluble.
  • the reaction is held at 100°C for 16 hours after which the temperature is increased to 120°C to remove toluene and added is 216 parts of Sunyl® 80. Volatiles are removed by vacuum distillation at 20 millimeters mercury at 140°C. The contents are filtered to give the desired product.
  • Component (B) may also be a nitrogen-containing polyacrylate prepared by reacting an acrylate ester of the formula wherein R9 is hydrogen or an alkyl group containing from 1 to about 4 carbon atoms and R10 is an alkyl, cycloalkyl or aromatic group containing from 4 to about 24 carbon atoms with a nitrogen containing compound. For each mole of the acrylate ester from 0.001 - 1.0 moles of the nitrogen containing compound is employed. The reaction is carried out at a temperature of from 50°C up to about 250°C.
  • the components (a'), (b'), (c'), (d') and (e') might be present in weight ratios of (a'):(b'):(c'):(d'):(e') in the ranges of about (1):(.01-1):(0.5-6):(0.5-22):(1-40) and most preferably (1):(0.2):(3):(11):(20); all ratios are in parts by weight.
  • the additive (C) may be selected from
  • the carboxylic dispersant composition is characterized by the presence within its molecular structure of (i) at least one polar group selected from acyl, acyloxy or hydrocarbyl-imidoyl groups, and (ii) at least one group in which a nitrogen or oxygen atom is attached directly to said group (i), and said nitrogen or oxygen atom also is attached to a hydrocarbyl group.
  • the structures of the polar group (i), as defined by the International Union of Pure and Applied Chemistry, are as follows (R27 representing a hydrocarbon or similar group): Acyl: Acyloxy: Hydrocarbylimidoyl:
  • the carboxylic dispersants can be prepared by the reaction of a hydrocarbon-substituted succinic acid-producing compound (herein sometimes referred to as the "succinic acylating agent") with at least about one-half equivalent, per equivalent of acid-producing compound, of an organic hydroxy compound, or an amine containing at least one hydrogen attached to a nitrogen group, or a mixture of said hydroxy compound and amine.
  • a hydrocarbon-substituted succinic acid-producing compound herein sometimes referred to as the "succinic acylating agent”
  • the carboxylic dispersants (C-4) obtained in this manner are usually complex mixtures whose precise composition is not readily identifiable.
  • the nitrogen- containing carboxylic dispersants are sometimes referred to herein as "acylated amines”.
  • a convenient route for the preparation of the nitrogen-containing carboxylic dispersants (C-3) comprises the reaction of a hydrocarbon-substituted succinic acid-producing compound ("carboxylic acid acylating agent") with an amine containing at least one hydrogen attached to a nitrogen atom (i.e., H-N ⁇ ).
  • the hydrocarbon-substituted succinic acid-producing compounds include the succinic acids, anhydrides, halides and esters.
  • the number of carbon atoms in the hydrocarbon substituent on the succinic acid-producing compound may vary over a wide range provided that the nitrogen-containing composition (C-3) is soluble in the lubricating compositions of the present invention.
  • Another source of the substantially hydrocarbon group comprises saturated aliphatic hydrocarbons such as highly refined high molecular weight white oils or synthetic alkanes such as are obtained by hydrogenation of high molecular weight olefin polymers illustrated above or high molecular weight olefinic substances.
  • olefin polymers having molecular weights (Mn) of about 700-10,000 are preferred.
  • Higher molecular weight olefin polymers having molecular weights (Mn) from about 10,000 to about 100,000 or higher have been found to impart also viscosity index improving properties to the final products of this invention.
  • the use of such higher molecular weight olefin polymers often is desirable.
  • the substituent is derived from a polyolefin characterized by an Mn value of about 700 to about 10,000, and an Mw/Mn value of 1.0 to about 4.0.
  • an equivalent weight of chlorinated polyalkene is the weight corresponding to the Mn value divided by the average number of chloro groups per molecule of chlorinated polyalkene while the equivalent weight of a maleic reactant is its molecular weight.
  • the ratio of chlorinated polyalkene to maleic reactant will normally be such as to provide about one equivalent of maleic reactant for each mole of chlorinated polyalkene up to about one equivalent of maleic reactant for each equivalent of chlorinated polyalkene with the understanding that it is normally desirable to provide an excess of maleic reactant; for example, an excess of about 5% to about 25% by weight. Unreacted excess maleic reactant may be stripped from the reaction product, usually under vacuum, or reacted during a further stage of the process as explained below.
  • Chlorine may be introduced continuously or intermittently during the one-step process.
  • the rate of introduction of the chlorine is not critical although, for maximum utilization of the chlorine, the rate should be about the same as the rate of consumption of chlorine in the course of the reaction.
  • the introduction rate of chlorine exceeds the rate of consumption, chlorine is evolved from the reaction mixture. It is often advantageous to use a closed system, including superatmospheric pressure, in order to prevent loss of chlorine so as to maximize chlorine utilization.
  • the upper limit of the useful temperature in the one-step process is determined primarily by the decomposition point of the components in the reaction mixture including the reactants and the desired products.
  • the decomposition point is that temperature at which there is sufficient decomposition of any reactant or product such as to interfere with the production of the desired products.
  • the amines may also contain non-hydrocarbon substituents or groups as long as these groups do not significantly interfere with the reaction of the amines with the acylating reagents of this invention.
  • non-hydrocarbon substituents or groups include lower alkoxy, lower alkyl mercapto, nitro, interrupting groups such as -O- and -S- (e.g., as in such groups as -CH2CH2-X-CH2CH2- where X is -O- or -S-).
  • the amines ordinarily contain less than about 40 carbon atoms in total and usually not more than about 20 carbon atoms in total.
  • Aliphatic monoamines include mono-aliphatic and dialiphatic substituted amines wherein the aliphatic groups can be saturated or unsaturated and straight or branched chain. Thus, they are primary or secondary aliphatic amines. Such amines include, for example, mono- and dialkyl-substituted amines, mono- and di-alkenyl-substituted amines, and amines having one N-alkenyl substituent and one N-alkyl substituent and the like. The total number of carbon atoms in these aliphatic monoamines will, as mentioned before, normally not exceed about 40 and usually not exceed about 20 carbon atoms.
  • Such monoamines include ethylamine, diethylamine, n-butylamine, di-n-butylamine, allylamine, isobutylamine, cocoamine, stearylamine, laurylamine, methyllaurylamine, oleyl-amine, N-methyl-octylamine, dodecylamine, octadecylamine, and the like.
  • Cycloaliphatic monoamines are those monoamines wherein there is one cycloaliphatic substituent attached directly to the amino nitrogen through a carbon atom in the cyclic ring structure.
  • Examples of cycloaliphatic monoamines include cyclohexylamines, cyclopentylamines, cyclohexenylamines, cyclopentenylamines, N-ethyl-cyclohexylamine, dicyclohexylamines, and the like.
  • aliphatic-substituted, cycloaliphatic-substituted, and heterocyclic-substituted aromatic monoamines are para-ethoxyaniline, para-dodecylaniline, cyclohexyl-substituted naphthylamine, and thienyl-substituted aniline.
  • substantially neutral or acidic dispersants are preferred, and a typical method of producing mixed oxygen- and nitrogen-bridged dispersants of this type (which are especially preferred) is to react the acylating agent with the hydroxy reagent first and subsequently react the intermediate thus obtained with a suitable nitrogen-containing reagent in an amount to afford a substantially neutral or acid product.
  • Example (C-3)-1 The procedure of Example (C-3)-1 is repeated using 55.0 grams (1.5 equivalents) of triethylene tetramine as the amine reactant. The resulting product has a nitrogen content of 2.9%.
  • a mixture is prepared by the addition of 57 parts (1.38 equivalents) of a commercial mixture of ethylene polyamine having from about 3 to 10 nitrogen atoms per molecule to 1067 parts of mineral oil and 893 parts (1.38 equivalents) of the substituted succinic acylating agent at 140-145°C.
  • the reaction mixture is heated to 155°C in 3 hours and stripped by blowing with nitrogen.
  • the reaction mixture if filtered to yield the filtrate as an oil solution of the desired product.
  • the fuel compositions of the present invention contain a major amount of a normally liquid fuel comprising
  • Synthetic ester base oils that comprise the reaction of a monocarboxylic acid of the formula R19COOH or a dicarboxylic acid of the formula with an alcohol of the formula R21(OH) n wherein R19 is a hydrocarbyl group containing from about 4 to about 24 carbon atoms, R20 is hydrogen or a hydrocarbyl group containing from about 4 to about 50 carbon atoms, R21 is a hydrocarbyl group containing from 1 to about 24 carbon atoms, m is an integer of from 0 to about 6 and n is an integer of from 1 to about 6.
  • Alcohols that may be employed are methyl alcohol, ethyl alcohol, butyl alcohol, the isomeric pentyl alcohols, the isomeric hexyl alcohols, dodecyl alcohol, 2-ethylhexyl alcohol, ethylene glycol, diethylene glycol, propylene glycol, neopentyl glycol, pentaerythritol, dipentaerythritol, trimethololpropane, bis-trimethololpropane, etc.
  • a non-exhaustive list of companies that produce synthetic esters and their trade names are BASF as Glissofluid, Ciba-Geigy as Reolube, JCI as Emkarote, Oleofina as Radialube and the Emery Group of Henkel Corporation as Emery 2964, 2911, 2960, 2976, 2935, 2971, 2930 and 2957.
  • Synthetic lubricating oils include hydrocarbon oils and halosubstituted hydrocarbon oils such as polymerized and interpolymerized olefins (e.g., polybutylenes, polypropylenes, propyleneisobutylene copolymers, chlorinated polybutylenes, etc.); poly(1-hexenes), poly(l-octenes), poly(1-decenes), etc.
  • hydrocarbon oils and halosubstituted hydrocarbon oils such as polymerized and interpolymerized olefins (e.g., polybutylenes, polypropylenes, propyleneisobutylene copolymers, chlorinated polybutylenes, etc.); poly(1-hexenes), poly(l-octenes), poly(1-decenes), etc.
  • alkylbenzenes e.g., dodecylbenzenes, tetradecylbenzenes, dinonylbenzenes, di-(2-ethylhexyl)benzenes, etc.
  • polyphenyls e.g., biphenyls, terphenyls, alkylated polyphenyls, etc.
  • Unrefined, refined and rerefined oils can also be used in the present invention.
  • Unrefined oils are those obtained directly from a natural or synthetic source without further purification treatment.
  • a shale oil obtained directly from retorting operations a petroleum oil obtained directly from primary distillation or ester oil obtained directly from an esterification process and used without further treatment would be an unrefined oil.
  • Refined oils are similar to the unrefined oils except they have been further treated in one or more purification steps to improve one or more properties. Many such purification techniques are known to those skilled in the art such as solvent extraction, secondary distillation, acid or base extraction, filtration, percolation, etc.
  • Vegetable oils having utility as a fuel in this invention are those vegetable oils obtained without genetic modification, i.e., their monounsaturation content (as oleic acid) is below 60 percent.
  • Vegetable oils having utility are canola oil, peanut oil, palm oil, corn oil, soybean oil, sunflower oil, cottonseed oil, safflower oil and coconut oil.
  • these fuel compositions contain an amount of the (A), (B) composition or (A), (B), (C) composition sufficient to improve one or more properties of the fuel such as rust-inhibition, dispersancy, etc., usually this amount is about 0.005 to about 0.5% by volume, preferably about 0.01 to about 0.1% by volume, based on the volume of such fuel compositions.
  • the fuel additive compositions of this invention can be added directly to the fuel, or they can be diluted with a substantially inert, normally liquid organic diluent such as naphtha, benzene, toluene, xylene or a normally liquid fuel as described above, to form an additive concentrate.
  • a substantially inert, normally liquid organic diluent such as naphtha, benzene, toluene, xylene or a normally liquid fuel as described above
  • These concentrates generally contain from about 20% to about 90% by weight of the composition of this invention and may contain, in addition, one or more other conventional additives known inthe art or described hereinabove.
  • the (A) : (B) weight ratio is generally from 90:10 to 99.5:0.5, preferably from 95:5 to 99.5:0.5 and most preferably from 98:2 to 99.5:0.5.
  • composition comprises components (A) and (B) or (A), (B) and (C) with (D) the following states the ranges of these components in parts by weight: Component Generally Preferred Most Preferred (A) 10-90 20-90 20-50 (B) 0.1-20 0.1-10 0.5-5 (C) zero or 0.001-1.0 zero or 0.01-0.5 zero or 0.01-0.1 (D) 10-90 20-90 20-50

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WO2004044104A1 (de) * 2002-11-13 2004-05-27 Lanxess Deutschland Gmbh Verfahren von 2,4-di-tert.-butylhydroxytoluol zur erhöhung der lagerstabilität von biodiesel
WO2005028597A1 (en) * 2003-09-15 2005-03-31 The Lubrizol Corporation Low temperature operable fatty acid ester fuel composition and method thereof
EP1736528A3 (de) * 2005-04-04 2007-01-10 Degussa GmbH Verfahren zur Erhöhung der Oxidationsstabilität von Biodiesel
WO2007076203A3 (en) * 2005-12-02 2007-08-16 Lubrizol Corp Low temperature stable fatty acid composition
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DE19529846A1 (de) * 1995-08-12 1997-02-13 Guenther Dr Boehmke Verfahren zur Herstellung von Kraftstoffen aus natürlichen Rohstoffen
WO1999027037A1 (de) * 1997-11-21 1999-06-03 Rohmax Additives Gmbh Additiv für biodiesel und biobrennstofföle
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CN100392048C (zh) * 2002-11-13 2008-06-04 兰爱克谢斯德国有限责任公司 用2,6-二叔丁基对甲酚提高生物柴油储存稳定性的方法
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WO2007076203A3 (en) * 2005-12-02 2007-08-16 Lubrizol Corp Low temperature stable fatty acid composition
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WO2007102948A2 (en) * 2006-02-03 2007-09-13 Eastman Chemical Company Antioxidant compositions useful in biodiesel and other fatty acid and acid ester compositions
US8075804B2 (en) * 2006-02-03 2011-12-13 Eastman Chemical Company Antioxidant compositions useful in biodiesel and other fatty acid and acid ester compositions
WO2007113035A1 (de) * 2006-04-06 2007-10-11 Evonik Rohmax Additives Gmbh Kraftstoffzusammensetzungen umfassend nachwachsende rohstoffe
WO2007115844A1 (de) * 2006-04-10 2007-10-18 Oxiris Chemicals S.A. Verfahren zur erhöhung der oxidationsstabilität von biodiesel
JP2007291391A (ja) * 2006-04-21 2007-11-08 Infineum Internatl Ltd バイオ燃料における改善
EP1847584A2 (de) * 2006-04-21 2007-10-24 Infineum International Limited Verbesserungen bei Biokraftstoffen
EP1847584A3 (de) * 2006-04-21 2008-10-22 Infineum International Limited Verbesserungen bei Biokraftstoffen
CN101058753B (zh) * 2006-04-21 2012-08-08 英菲诺姆国际有限公司 生物燃料的改进
EP2052061A2 (de) * 2006-07-11 2009-04-29 Innospec Fuel Specialties LLC Stabilisatorzusammensetzungen für mischungen von erdölbrennstoffen und erneuerbaren brennstoffen
EP2052061A4 (de) * 2006-07-11 2012-01-25 Innospec Fuel Specialties Llc Stabilisatorzusammensetzungen für mischungen von erdölbrennstoffen und erneuerbaren brennstoffen
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JP2018515661A (ja) * 2015-05-22 2018-06-14 アクゾ ノーベル ケミカルズ インターナショナル ベスローテン フエンノートシャップＡｋｚｏ Ｎｏｂｅｌ Ｃｈｅｍｉｃａｌｓ Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｂ．Ｖ． 二環式（メタ）アクリレート及びアルキル（メタ）アクリレートのコポリマー、並びに燃料におけるレオロジー調整剤としてのその使用
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AU5901694A (en) 1994-12-01
ES2135542T3 (es) 1999-11-01
DE69419456D1 (de) 1999-08-19
EP0626442B1 (de) 1999-07-14
CA2117278A1 (en) 1994-11-25
DE69419456T2 (de) 2000-01-05
AU674052B2 (en) 1996-12-05

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