EP0626442B1 - Esters d'acide gras, traités par un agent d'abaissement du point d'écoulement, comme carburants biodégradables - Google Patents

Esters d'acide gras, traités par un agent d'abaissement du point d'écoulement, comme carburants biodégradables Download PDF

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EP0626442B1
EP0626442B1 EP19940303590 EP94303590A EP0626442B1 EP 0626442 B1 EP0626442 B1 EP 0626442B1 EP 19940303590 EP19940303590 EP 19940303590 EP 94303590 A EP94303590 A EP 94303590A EP 0626442 B1 EP0626442 B1 EP 0626442B1
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oil
carbon atoms
ester
parts
group
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EP0626442A1 (fr
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Kasturi Lal
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Lubrizol Corp
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Lubrizol Corp
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Claims (9)

  1. Une composition comprenant :
    (A) des esters résultant de la trans-estérification d'au moins un triglycéride d'huile animale ou végétale de la formule
    Figure 00800001
    avec un alcool R4OH, où R1, R2 et R3 sont des groupes aliphatiques contenant de 6 à 24 atomes de carbone et R4 est un groupe aliphatique contenant de 1 à 10 atomes de carbone ;
    (B) un abaisseur de point d'écoulement ; et
    (C)(4) un anti-oxydant comprenant :
    (a) au moins un alcoyl phénol de la formule
    Figure 00800002
    où R22 est un groupe t-butyle ; et
    (b) un benzotriazole de la formule
    Figure 00810001
    où R23 est un groupe méthyle ; et
    (c) au moins une amine aromatique de la formule
    Figure 00810002
    où R24 est
    Figure 00810003
    et R25 et R26 sont des groupes nonyle.
  2. La composition selon la revendication 1, dans laquelle le triglycéride d'huile végétale comprend de l'huile de tournesol, de l'huile de carthame, de l'huile de maïs, de l'huile de soja, de l'huile de colza, de l'huile de pâturin ou l'une de ces huiles modifiée génétiquement.
  3. La composition selon la revendication 1 ou 2, dans laquelle la trans-estérification est effectuée en présence d'un catalyseur comprenant des alcoolates de métaux alcalins ou alcalino-terreux et à une température comprise entre la température ambiante et la température de décomposition de l'un quelconque des corps en réaction ou des produits.
  4. La composition selon l'une quelconque des revendications précédentes, dans laquelle l'abaisseur de point d'écoulement est un ester mixte ayant des propriétés de modification à basse température d'un interpolymère carboxylé, cet interpolymère ayant une viscosité spécifique réduite comprise entre 0,05 et 2 et étant dérivé d'au moins deux monomères, un de ces monomères étant une oléfine aliphatique de bas poids moléculaire, du styrène ou un styrène substitué dans lequel le substituant est un groupe hydrocarbyle contenant de 1 à 18 atomes de carbone, et l'autre de ces monomères étant un acide aliphatique insaturé en alpha, bêta ou un anhydride ou ester de cet acide, cet ester étant substantiellement exempt d'acidité titrable et étant caractérisé par la présence dans sa structure polymère d'au moins un de chacun de trois groupes polaires pendants qui sont dérivés des groupes carboxy de cet ester :
    (i) un groupe ester carboxylique de poids moléculaire relativement élevé, ce groupe ester carboxylique ayant de 8 à 24 atomes de carbone aliphatiques dans le radical ester,
    (ii) un groupe ester carboxylique de poids moléculaire relativement bas ayant de 3 à 7 atomes de carbone aliphatiques dans le radical ester, où le rapport molaire de (i) à (ii) est compris entre 1:1 et 20:1, et éventuellement
    (iii) un groupe carbonyl-amino dérivé d'un composé aminé ayant un groupe amino primaire ou secondaire, où le rapport molaire de (i) : (ii) : (iii) est de (50-100) : (5-50) : (0,1-15).
  5. La composition selon la revendication 4, dans laquelle l'interpolymère carboxylé est un terpolymère d'une proportion molaire de styrène, une proportion molaire d'anhydride maléique et moins de 0,3 proportion molaire d'un monomère vinylique.
  6. La composition selon l'une quelconque des revendications 1 à 3, dans laquelle l'abaisseur de point d'écoulement est un polymère d'acrylate de la formule
    Figure 00830001
    où R5 est de l'hydrogène ou un groupe alcoyle inférieur contenant de 1 à environ 4 atomes de carbone, R6 est un mélange de groupes alcoyle contenant de 4 à 24 atomes de carbone et x est un nombre entier fournissant au polymère d'acrylate un poids moléculaire moyen en poids compris entre 5 000 et 1 000 000.
  7. La composition selon l'une quelconque des revendications 1 à 3, dans laquelle l'abaisseur de point d'écoulement est un mélange de composés ayant la formule de structure générale Ar-(R7)-[-Ar'(R8)]nAr'' où Ar, Ar' et Ar" sont chacun indépendamment une portion aromatique contenant 1 à 3 noyaux aromatiques et le mélange comprend des composés dans lesquels sont présentes des portions avec 0 substituant, 1 substituant, 2 substituants et 3 substtuants, R7 et R8 sont chacun indépendamment un groupe alcoylène contenant de 1 à 100 atomes de carbone et n est un nombre de 0 à 1 000.
  8. La composition selon l'une quelconque des revendications 1 à 3, dans laquelle l'abaisseur de point d'écoulement est un polyméthacrylate azoté préparé en faisant réagir un ester méthacrylate de la formule
    Figure 00830002
    dans laquelle R9 est de l'hydrogène ou un groupe alcoyle contenant de 1 à 4 atomes de carbone et R10 est un groupe alcoyle contenant de 1 à 24 atomes de carbone, avec un ester contenant de l'azote à raison de 0,1 à 20 moles de l'ester contenant de l'azote pour chaque mole de l'ester méthacrylate.
  9. Une composition combustible comprenant une quantité majeure de (D) un combustible normalement liquide, où le combustible comprend
    (1) un distillat de pétrole ;
    (2) une huile synthétique à base d'ester comprenant la réaction d'un acide monocarboxylique de la formule R19COOH ou d'un acide dicarboxylique de la formule
    Figure 00840001
    avec un alcool de la formule R21(OH)t où R19 est un groupe hydrocarbyle contenant de 4 à 24 atomes de carbone, R20 est de l'hydrogène ou un groupe hydrocarbyle contenant de 4 à 50 atomes de carbone, R21 est un groupe hydrocarbyle contenant de 1 à 24 atomes de carbone, m est 0 ou un nombre entier de 1 à 6 et t est un nombre entier de 1 à 6 ;
    (3) une huile minérale ;
    (4) une poly-alpha-oléfine ; et/ou
    (5) une huile végétale ;
    et une quantité mineure de la composition selon l'une quelconque des revendications précédentes.
EP19940303590 1993-05-24 1994-05-19 Esters d'acide gras, traités par un agent d'abaissement du point d'écoulement, comme carburants biodégradables Expired - Lifetime EP0626442B1 (fr)

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US8075804B2 (en) 2006-02-03 2011-12-13 Eastman Chemical Company Antioxidant compositions useful in biodiesel and other fatty acid and acid ester compositions
US9447342B2 (en) 2005-12-02 2016-09-20 The Lubrizol Corporation Low temperature stable fatty acid composition

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CN107636127A (zh) 2015-05-22 2018-01-26 国际壳牌研究有限公司 燃料组合物
BR112017024508A2 (pt) 2015-05-22 2018-07-24 Akzo Nobel Chemicals Int Bv copolímero solúvel para pelo menos 2% em peso em diesel a 25ºc, pacote aditivo para combustíveis, método de preparação de copolímero, método de preparação de um pacote de aditivos para combustível, e uso de polímero
JP6688322B2 (ja) 2015-05-22 2020-04-28 シエル・インターナシヨネイル・リサーチ・マーチヤツピイ・ベー・ウイＳｈｅｌｌ Ｉｎｔｅｒｎａｔｉｏｎａｌｅ Ｒｅｓｅａｒｃｈ Ｍａａｔｓｃｈａｐｐｉｊ Ｂｅｓｌｏｔｅｎ Ｖｅｎｎｏｏｔｓｈａｐ 燃料組成物
CN108603131B (zh) 2016-02-05 2022-01-21 国际壳牌研究有限公司 燃料组合物
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US9447342B2 (en) 2005-12-02 2016-09-20 The Lubrizol Corporation Low temperature stable fatty acid composition
US8075804B2 (en) 2006-02-03 2011-12-13 Eastman Chemical Company Antioxidant compositions useful in biodiesel and other fatty acid and acid ester compositions
US9422508B2 (en) 2006-02-03 2016-08-23 Eastman Chemical Company Antioxidant compositions useful in biodiesel and other fatty acid and acid ester compositions

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DE69419456T2 (de) 2000-01-05
AU5901694A (en) 1994-12-01
CA2117278A1 (fr) 1994-11-25
DE69419456D1 (de) 1999-08-19
AU674052B2 (en) 1996-12-05
EP0626442A1 (fr) 1994-11-30

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