公开(公告)号：US07566794B2

公开(公告)日：2009-07-28

申请号：US11523735

申请日：2006-09-20

申请人： Gérard Hillion ,  Bruno Delfort

发明人： Gérard Hillion ,  Bruno Delfort

IPC分类号： C11C3/00

CPC分类号： C07C67/03 ,  C11C3/003 ,  Y02E50/13 ,  C07C69/24 ,  C07C69/52

摘要： A method allowing, from natural fat or oils, or from other glyceride mixtures, to obtain fatty acid ethyl esters that can be used as gas oil substitutes, comprises: stage (a) oil, fat or a glyceride mixture is transesterified by ethanol using a soluble catalyst or a catalyst that becomes soluble during the reaction; stage (b) resultant glycerin is decanted and removed, without requiring an excess ethanol evaporation operation, stage (c) a second transesterification is conducted to obtain a product whose ester content is at least 97% by mass, stage (d) evaporation of excess ethanol is carried out in the presence of the catalyst under suitable conditions preventing a reverse transesterification reaction, the resultant ethanol being practically anhydrous, stage (e) the ester undergoes purification by water wash sequences, and stage (f) the ester is dried under reduced pressure.

摘要翻译： 一种允许天然脂肪或油或其它甘油酯混合物获得可用作瓦斯油替代物的脂肪酸乙酯的方法包括：（a）将油，脂肪或甘油酯混合物用乙醇酯交换，使用 可溶性催化剂或在反应期间变得可溶的催化剂; 阶段（b）将得到的甘油滗析并除去，而不需要过量的乙醇蒸发操作，阶段（c）进行第二次酯交换以获得酯含量为至少97质量％的产物，阶段（d）蒸发过量 乙醇在催化剂存在下在合适的条件下进行，防止反向酯交换反应，所得乙醇实际上是无水的，阶段（e）酯通过水洗涤顺序进行纯化，并且阶段（f）将酯在还原条件下干燥 压力。

公开(公告)号：US06476081B1

公开(公告)日：2002-11-05

申请号：US09573559

申请日：2000-05-19

申请人： Gérard Hillion ,  Isabelle Durand ,  Anne Sinquin ,  Marie Velly

发明人： Gérard Hillion ,  Isabelle Durand ,  Anne Sinquin ,  Marie Velly

IPC分类号： B01F1722

CPC分类号： B01F17/005 ,  Y10S516/915

摘要： In order to manufacture a composition mainly containing compounds with ester and amide functions, in particular in the form of ester-amides, as well as compounds with amine functions, such as ester-amines, the salts of amines, monoglycerides and diglycerides, formed from monomeric, dimeric, trimeric and/or tetrameric fatty acids contained in a polymerized polyunsaturated oil, a process is implemented which comprises the following stages: a) use (or preparation) of a polymerized oil by polymerization of a polyunsaturated vegetable or animal oil; b) treatment of said polymerized oil by entrainment with water vapor; and c) reaction of the polymerized oil thus treated with an excess of at least one aminoalcohol, in the presence or not of a catalyst. This composition can be used as an emulsifying and dispersing surfactant, in particular as an additive for dispersing hydrates in oil effluents.

摘要翻译： 为了制备主要含有具有酯和酰胺官能团的化合物的组合物，特别是酯 - 酰胺形式的化合物，以及具有胺官能团的化合物，例如酯 - 胺，胺，单甘油酯和甘油二酯的盐，由 包含在聚合多不饱和油中的单体，二聚，三聚和/或四聚脂肪酸，实施包括以下步骤的方法：a）通过多不饱和植物油或动物油的聚合使用（或制备）聚合油; b ）通过夹带水蒸气处理所述聚合油; 在这种催化剂的存在或不存在下，这样处理的聚合油与过量的至少一种氨基醇的反应。该组合物可用作乳化和分散表面活性剂，特别是作为用于将水合物分散在油污水中的添加剂 。

公开(公告)号：US06221920B1

公开(公告)日：2001-04-24

申请号：US09160290

申请日：1998-09-25

申请人： Gérard Hillion ,  Isabelle Durand ,  Robert Stern ,  Marie Velly

发明人： Gérard Hillion ,  Isabelle Durand ,  Robert Stern ,  Marie Velly

IPC分类号： B01F304

CPC分类号： C07C233/20 ,  B01F17/0042 ,  Y10S516/915

摘要： The following are described herein: a composition that consists of a mixture that comprises at least amides, amines, ester-amides, ester-amines, amine salts and monoglycerides, that are all derived from monomeric, dimeric, trimeric and/or tetrameric fatty acids; a process for the production of said composition which comprises the transamidification reaction of a polyunsaturated vegetable oil that is polymerized thermally, with an excess of at least one amino alcohol, which may or may not be in the presence of a catalyst; and the uses of this composition particularly as an emulsifying agent that allow it, depending on the nature of the oil, to form an oil-in-water or water-in-oil emulsion, as a solid-dispersing agent, or as an agent for the stabilization of foams in a liquid or an emulsion.

摘要翻译： 本文描述了以下：由至少包含酰胺，胺，酯 - 酰胺，酯 - 胺，胺盐和单甘油酯的混合物组成的组合物，其全部衍生自单体，二聚，三聚和/或四聚脂肪酸 ; 一种用于生产所述组合物的方法，其包括热聚合的多不饱和植物油与过量的至少一种氨基醇的酰胺化反应，其可以或不在催化剂存在下; 以及该组合物的特别用作乳化剂的用途，根据油的性质，其可以形成水包油或油包水乳液，作为固体分散剂或作为试剂 用于稳定液体或乳液中的泡沫。

公开(公告)号：US07906663B2

公开(公告)日：2011-03-15

申请号：US11626077

申请日：2007-01-23

申请人： Hélène Olivier-Bourbigou ,  Christophe Vallee ,  Gérard Hillion

发明人： Hélène Olivier-Bourbigou ,  Christophe Vallee ,  Gérard Hillion

IPC分类号： C07C51/00

CPC分类号： C07C51/347 ,  C07C1/213 ,  C07C6/04 ,  C07C67/333 ,  C07C67/475 ,  C07C2531/24 ,  C07C11/04 ,  C07C11/02 ,  C07C57/13 ,  C07C69/533 ,  C07C69/593

摘要： In order to produce both an olefinic fraction and a composition of diacids or diesters of fats, a process is carried out which comprises, in succession: a) metathesis of an unsaturated fat with ethylene in the presence of at least one non-aqueous ionic liquid; b) separating and recycling the ionic liquid used in the first step; c) separating, by distillation, the olefinic fraction (fraction A) from the unsaturated fat mono-ester or mono-basic acid fraction (fraction B) formed in step a); d) homometathesis of the mono-unsaturated fat ester or acid cut (fraction B) which allows the co-production of unsaturated fat diesters or diacids (fraction C) and ethylene which is recycled to the first methathesis step of the process; and e) optionally, recycling the ionic liquid containing the catalyst used in step d). Of particular application to an oleic sunflower oil, an oleic rapeseed oil or to a mixture of mono-alcohol esters of said oils, whereupon the process can produce both an olefinic fraction (mainly composed of 1-decene) and a composition of diesters or diacids wherein, in general, over half of the chains is constituted by unsaturated C18 chains (mainly composed of octadecene-9 1,18-iacid or diester) and to recycle the ethylene employed.

摘要翻译： 为了产生烯烃级分和脂肪二酸或二酯的组合物，进行了以下过程：a）在至少一种非水离子液体的存在下，不饱和脂肪与乙烯的复分解 ; b）分离和再循环第一步中使用的离子液体; c）通过蒸馏从步骤a）中形成的不饱和脂肪单酯或单碱性酸部分（级分B）分离出烯烃级分（级分A）; d）单不饱和脂肪酯或酸切割（B馏分）的同位素，其允许共生产不饱和脂肪二酯或二酸（馏分C）和乙烯，其被再循环到该方法的第一个复分解步骤; 和e）任选地，循环含步骤d）中使用的催化剂的离子液体。 特别适用于油酸向日葵油，油菜菜籽油或所述油的单醇酯的混合物，于是该方法可以产生烯​​烃级分（主要由1-癸烯组成）和二酯或二酸的组合物 其中通常一半以上的链由不饱和C18链（主要由十八碳烯-9,18-酸或二酯组成）构成，并循环使用乙烯。

公开(公告)号：US07652156B2

公开(公告)日：2010-01-26

申请号：US11523737

申请日：2006-09-20

申请人： Gérard Hillion ,  Bruno Delfort

发明人： Gérard Hillion ,  Bruno Delfort

IPC分类号： C11C3/00

CPC分类号： C11C3/003 ,  C10L1/026 ,  Y02E50/13

摘要： A method allowing, from natural fat or oils, vegetable or animal, or from other glyceride mixtures, to obtain in a quasi-quantitative way fatty acid ethyl esters that can be used as gas oil substitutes, comprises the succession of stages as follows: a stage (a) wherein the oil, the fat or the glyceride mixture is transesterified by ethanol using a soluble catalyst or a catalyst that becomes soluble during the reaction, a stage (b) wherein the glycerin formed is decanted and removed, without requiring an excess ethanol evaporation operation, a stage (c) wherein a second transesterification reaction is carried out so as to obtain a product whose ester content is at least 97% by mass, a stage (d) wherein controlled neutralization of the catalyst is carried out, a stage (e) wherein the excess ethanol is removed by distillation, a stage (f) wherein the ester undergoes purification by means of water wash sequences, and a stage (g) wherein the ester mixture is dried under reduced pressure.

摘要翻译： 从天然脂肪或油，植物或动物或其他甘油酯混合物中获得可以用作准油替代物的脂肪酸乙酯的准定量方法的方法包括以下连续步骤：a 阶段（a）其中油，脂肪或甘油酯混合物通过乙醇使用可溶性催化剂或在反应期间变得可溶的催化剂进行酯交换，其中将形成的甘油倾析并除去而不需要过量的阶段（b） 乙醇蒸发操作，其中进行第二酯交换反应以获得其酯含量为至少97质量％的产物的阶段（c），进行催化剂的控制中和的阶段（d）， 通过蒸馏除去过量乙醇的阶段（e），其中酯通过水洗涤顺序进行纯化的阶段（f）和其中酯混合物在减压下干燥的阶段（g）。

公开(公告)号：US07420073B2

公开(公告)日：2008-09-02

申请号：US10802042

申请日：2004-03-17

申请人： Gérard Hillion ,  Dominique Le Pennec

发明人： Gérard Hillion ,  Dominique Le Pennec

IPC分类号： C07C51/09

CPC分类号： C07C67/03 ,  C11C3/10 ,  C07C69/24 ,  C07C69/52

摘要： A process that employs a heterogeneous catalyst comprising a zinc aluminate mixed oxide and having the following formula: ZnAl2O4, xZnO, yAl2O3 in which x and y each represent a number in the range 0 to 2, and in which the zinc aluminate is more particularly of the spinel type, makes it possible, by means of C1 to C5 monoalcohols, to: transesterify vegetable or animal oils having a natural free acidity, such as unrefined degummed rapeseed, soya, sunflower oils or exotic oils of the African oil, palm nut oil or coconut oil type, which are naturally rich in fatty acids; and simultaneously esterify their free acidity; so as to use phospholipid free and/or degummed unrefined acid oil with an acid number in the range 0.5 to 20, for example 1 to 15 and preferably 2 to 12, to produce esters, for example methyl esters, for use as fuels.

摘要翻译： 使用包含铝酸锌混合氧化物并具有下式的多相催化剂的方法：<？在线公式描述=“在线配方”末端=“铅”→ZnAl 2 λ-in-line-formula description =“In-line Formulas”end =“tail” 其中x和y各自表示0至2范围内的数字，其中铝酸锌更特别是尖晶石型，可以通过C1至C5一元醇：将植物或动物进行酯交换 具有天然游离酸度的油，例如天然富含脂肪酸的非精油脱胶油菜籽，大豆，向日葵油或非洲油，棕榈仁油或椰子油型的异国油; 并同时酯化其游离酸度; 以便使用酸值为0.5至20，例如1至15，优选2至12的无磷酸和/或脱胶的未精制酸性油，以生产用作燃料的酯，例如甲酯。

公开(公告)号：US06452029B1

公开(公告)日：2002-09-17

申请号：US09362217

申请日：1999-07-28

申请人： Gérard Hillion ,  Hélène Olivier ,  Katja Siepen ,  Dominique Commereuc ,  Robert Stern

发明人： Gérard Hillion ,  Hélène Olivier ,  Katja Siepen ,  Dominique Commereuc ,  Robert Stern

IPC分类号： C09F706

CPC分类号： C10M105/34 ,  C07C67/303 ,  C07C67/347 ,  C07C69/24 ,  C07C69/587

摘要： A nickel catalytic system that makes it possible to obtain branched compounds from fatty substances by reacting simple olefins on polyunsaturated esters, which may or may not be conjugated, is described. The compounds that are obtained may be hydrogenated and used as lubricant bases or may be transformed according to known procedures into compounds of acid, alcohol, amine or amide type, used in varied applications.

摘要翻译： 描述了一种镍催化体系，其可以通过在多不饱和酯上反应简单的烯烃从脂肪物质获得支链化合物，其可以或可以不共轭。 获得的化合物可以被氢化并用作润滑剂基质，或者可以根据已知的方法转化成用于各种应用的酸，醇，胺或酰胺型的化合物。

公开(公告)号：US07851643B2

公开(公告)日：2010-12-14

申请号：US11521613

申请日：2006-09-15

申请人： Gérard Hillion ,  Bruno Delfort

发明人： Gérard Hillion ,  Bruno Delfort

IPC分类号： C11C3/00 ,  C10L1/18

CPC分类号： C11C3/003 ,  C07C67/03 ,  Y02E50/13 ,  C07C69/24 ,  C07C69/52

摘要： A method of manufacturing an ester composition comprising ethyl esters of linear monocarboxylic acids having 6 to 26 carbon atoms from a vegetable or an animal oil, neutral or acid, virgin or recycled, the method comprising: a stage 1 of reaction of vegetable or animal oil with methanol, in the presence of a heterogeneous catalyst comprising a combination of at least one metallic oxide and alumina or a combination of at least two metallic oxides and possibly alumina, and a stage 2 of reaction of the product from stage 1 with ethanol in the presence of a heterogeneous catalyst as defined for stage 1, so as to obtain from vegetable or animal oils, a mixture of fatty acid esters rich in fatty acid ethyl esters and a glycerin of high purity.

摘要翻译： 一种制备酯组合物的方法，所述酯组合物包含来自植物或动物油，中性或酸性，原始或再循环的具有6至26个碳原子的直链单羧酸的乙酯，所述方法包括：植物或动物油的反应阶段1 在含有至少一种金属氧化物和氧化铝的组合的多相催化剂或至少两种金属氧化物和可能的氧化铝的组合的非均相催化剂的存在下，以及来自阶段1的产物与乙醇的反应阶段2 存在为阶段1定义的多相催化剂，从而获得植物油或动物油，富含脂肪酸乙酯的脂肪酸酯和高纯度甘油的混合物。

公开(公告)号：US06492430B1

公开(公告)日：2002-12-10

申请号：US09573558

申请日：2000-05-19

申请人： Gérard Hillion ,  Isabelle Durand ,  Anne Sinquin ,  Marie Velly

发明人： Gérard Hillion ,  Isabelle Durand ,  Anne Sinquin ,  Marie Velly

IPC分类号： B01F304

CPC分类号： B01F17/005 ,  Y10S516/914 ,  Y10S516/915

摘要： A process for preparing a composition comprising a mixture with ester and amine function in the form of ester-amines, amines, salts of amines, monoglycerides and diglycerides all derived from monomeric, dimeric, trimeric, and/or tetrameric fatty acids contained in polymerized polyunsaturated oil comprising: (a) polymerizing a polyunsaturated vegetable or animal oil to form a polymerized oil, (b) treating the polymerized oil with water vapor, and (c) reacting the polymerized oil with an excess of at least one compound containing at least one hydroxyl function and at least one tertiary amine function, optionally in the presence of a catalyst. Said methods further comprise adding the compositions to an oil effluent as dispersing agents for hydrates.

摘要翻译： 制备包含酯和胺的混合物的组合物的方法以酯 - 胺，胺，胺，单酸甘油酯和甘油二酸酯的形式起作用，其全部衍生自聚合多不饱和物中所含的单体，二聚，三聚和/或四聚脂肪酸 油包括：（a）聚合多不饱和植物油或动物油以形成聚合油，（b）用水蒸汽处理聚合的油，和（c）使聚合的油与过量的至少一种含至少一种 羟基官能团和至少一种叔胺官能团，任选地在催化剂存在下。 所述方法还包括将组合物加入油流出物中作为水合物的分散剂。

公开(公告)号：US07754904B2

公开(公告)日：2010-07-13

申请号：US11626082

申请日：2007-01-23

申请人： Hélène Olivier-Bourbigou ,  Gérard Hillion ,  Christophe Vallee

发明人： Hélène Olivier-Bourbigou ,  Gérard Hillion ,  Christophe Vallee

IPC分类号： C11C1/00

CPC分类号： C07C1/2078 ,  C07C51/347 ,  C07C67/475 ,  C07C2523/46 ,  C07C11/02 ,  C07C57/13 ,  C07C69/593

摘要： A process is described in which an unsaturated fat is reacted in a homometathesis reaction in the presence of at least one non-aqueous ionic liquid to produce both an olefinic fraction and a composition of monoalcohol diesters or diacids.Particular application to a mixture of esters of an oleic sunflower seed oil or an oleic rapeseed oil, the process producing both an olefinic fraction and a composition of monoalcohol diesters or diacids wherein, in general, more than half of its chains is constituted by unsaturated C18 chains.

摘要翻译： 描述了一种方法，其中不饱和脂肪在同位素反应中在至少一种非水离子液体的存在下反应，以产生烯烃级分和单醇二酯或二酸的组合物。 特别适用于油酸向日葵籽油或油菜菜籽油的酯的混合物，该方法生产烯烃级分和单醇二酯或二酸的组合物，其中通常一半以上的链由不饱和C18 链条