公开(公告)号：US5880298A

公开(公告)日：1999-03-09

申请号：US186483

申请日：1994-01-14

申请人： Gerard Hillion ,  Robert Stern ,  Odile Le Borgne

发明人： Gerard Hillion ,  Robert Stern ,  Odile Le Borgne

IPC分类号： C07C67/465 ,  C09F7/00 ,  C07B35/08

CPC分类号： C07C67/465

摘要： For the oligomerization of a fatty ester or fatty acid containing conjugated double bonds, the reaction uses a catalyst consisting of an activated earth, e.g., montmorillonite, at a temperature of from 100.degree.-180.degree. C., preferably from 130.degree.-160.degree. C. The process can be carried out continuously or in a batch process on a fixed bed and is particularly applicable to conjugated methyl esters obtained by conjugating and transesterifying sunflower seed oil. The oligomerized products obtained are particularly useful as lubricants or polycondensation reactants.

摘要翻译： 对于含有共轭双键的脂肪酸酯或脂肪酸的低聚反应，使用由活化土如蒙脱石组成的催化剂，温度为100-180℃，优选130-160℃。 C.该方法可以在固定床上连续进行或以间歇方式进行，特别适用于通过将向日葵籽油接合和酯交换得到的共轭甲酯。 获得的低聚产物特别可用作润滑剂或缩聚反应物。

公开(公告)号：US5476956A

公开(公告)日：1995-12-19

申请号：US232984

申请日：1994-04-25

申请人： Gerard Hillion ,  Robert Stern ,  Abakar Kotoko ,  Yves Chauvin

发明人： Gerard Hillion ,  Robert Stern ,  Abakar Kotoko ,  Yves Chauvin

IPC分类号： B01J27/13 ,  B01J31/16 ,  C07B37/02 ,  C07B61/00 ,  C07C2/04 ,  C07C2/38 ,  C07C11/12 ,  C07C67/347 ,  C07C69/65 ,  C09F7/06

CPC分类号： C07C2/04 ,  C07B37/02 ,  C07C67/347 ,  C07C2531/22

摘要： Co dimerization is conducted of at least one monoolefin, for example a monoolefinic hydrocarbon such as ethylene, propylene or 1-butene, a halogenated monoolefin such as vinyl chloride, or an olefinic functional compound such as methyl acrylate, acrylonitrile, allyl acetate or vinyl acetate, with at least one polyolefin containing at least two conjugated or unconjugated ethylene bonds, for example a diene hydrocarbon such as 1,3-butadiene, piperylene, or isoprene or a polyolefin containing a carboxylic function, such as a fatty acid or a fatty acid ester having 14 to 24 carbon atoms in the fatty chain derived, for example, from a natural oil. The reaction is carried out in the presence of a catalytic system having general formula [RhX.sub.4 ][YR.sub.4 ] where X represents a halogen ion or a SO.sub.4.sup.--, SO.sub.3.sup.-, OH.sup.-, OR.sup.- or R.sup.- group, at least one X being a halogen ion, Y represents a nitrogen atom or a phosphorous atom, and R represents an alkyl, cycloalkyl, alkenyl, aryl, alkylaryl, polystyryl, alkyl polystyryl or acyl radical.

摘要翻译： Co二聚化由至少一种单烯烃，例如单烯烃如乙烯，丙烯或1-丁烯，卤代单烯烃如氯乙烯或烯属官能化合物如丙烯酸甲酯，丙烯腈，乙酸烯丙酯或乙酸乙烯酯 与至少一种含有至少两个共轭或非共轭的乙烯键的聚烯烃，例如二烯烃如1,3-丁二烯，戊间二烯或异戊二烯或含有羧酸官能团的聚烯烃如脂肪酸或脂肪酸 在脂肪链中具有14至24个碳原子的酯衍生自例如天然油。 该反应在具有通式[RhX4] [YR4]的催化体系存在下进行，其中X表示卤素离子或SO 4 - ，SO 3 - ，OH-，OR-或R-基团，至少一个X 作为卤素离子，Y表示氮原子或磷原子，R表示烷基，环烷基，烯基，芳基，烷基芳基，聚苯乙烯基，烷基聚苯乙烯基或酰基。

公开(公告)号：US4554397A

公开(公告)日：1985-11-19

申请号：US643936

申请日：1984-08-24

申请人： Robert Stern ,  Gerard Hillion

发明人： Robert Stern ,  Gerard Hillion

IPC分类号： B01J25/02 ,  B01J31/12 ,  B01J31/28 ,  C07C1/207 ,  C07C1/213 ,  C07C1/00

CPC分类号： C07C1/2078 ,  B01J25/02 ,  B01J31/122 ,  C07C1/213 ,  C07C2523/755 ,  C07C2523/835 ,  C07C2525/02 ,  C07C2531/26

摘要： A linear olefin is manufactured by contacting a fatty acid or ester with a catalyst comprising nickel and at least one metal from the group consisting of tin, germanium and lead at 200.degree.-400.degree. C.

摘要翻译： 线性烯烃是通过在200-400℃下使脂肪酸或酯与包含镍和至少一种金属的催化剂与锡，锗和铅接触来制造的。

公开(公告)号：US4695411A

公开(公告)日：1987-09-22

申请号：US830169

申请日：1986-02-18

申请人： Robert Stern ,  Gerard Hillion ,  Paul Gateau ,  Jean-Claude Guibet

发明人： Robert Stern ,  Gerard Hillion ,  Paul Gateau ,  Jean-Claude Guibet

IPC分类号： C10G3/00 ,  C10L1/02 ,  C10L1/14 ,  C10L1/18 ,  C11C3/04 ,  C11C3/10

CPC分类号： C11C3/04 ,  C10L1/026 ,  C10L1/143 ,  C10L1/18 ,  C10G2300/1003 ,  C10G2300/1011 ,  C10G2400/04 ,  Y02E50/13 ,  Y02P30/20

摘要： The invention concerns a process for manufacturing a composition of fatty acid esters useful as gas oil substitute motor fuel, said composition containing at least one hydrated ethyl alcohol.The process comprises:(A) A first acid transesterification step in the presence of at least one aliphatic, linear or branched monoalcohol of 1 to 5 carbon atoms, consisting at least partly of hydrated ethyl alcohol containing 1 to 60% by weight of water, said step leading to the formation of a phase mainly containing ethyl esters after removal of the produced glycerol phase,(B) A second step wherein the initial free acidity or that formed during the first step in the phase containing the esters is decreased to a value at most equal to about 2%; and(C) A third step of basic transesterification of the phase resulting from step B, in the presence of at least one aliphatic, linear or branched monoalcohol of 1 to 5 carbon atoms, with the recovery of the so-formed ester composition.The composition of the invention can be used for combustion in Diesel engines.

摘要翻译： 本发明涉及制备用作瓦斯油替代运动燃料的脂肪酸酯组合物的方法，所述组合物含有至少一种水合乙醇。 该方法包括：（A）在至少一种含有1至5个碳原子的脂肪族，直链或支链一元醇存在下的第一酸酯交换步骤，至少部分由至少部分含有1至60重量％水的水合乙醇， 所述步骤导致在除去产生的甘油相后主要含有乙酯的相的形成，（B）第二步，其中初始游离酸度或在含有酯的相中的第一步中形成的第一步降低至值 最多等于约2％; 和（C）在至少一种具有1至5个碳原子的脂肪族，直链或支链一元醇存在下，由步骤B产生的相进行碱性酯交换的第三步骤，回收如此形成的酯组合物。 本发明的组合物可用于柴油发动机的燃烧。

公开(公告)号：US6013817A

公开(公告)日：2000-01-11

申请号：US852737

申请日：1997-05-07

申请人： Robert Stern ,  Gerard Hillion ,  Mohammed Neguib Eisa

发明人： Robert Stern ,  Gerard Hillion ,  Mohammed Neguib Eisa

IPC分类号： C07C67/03 ,  C11C3/04 ,  C11C3/10 ,  C07C51/00

CPC分类号： C11C3/003 ,  C07C67/03 ,  C11C3/04 ,  C11C3/10

摘要： For the production of ethyl esters of fatty acids from fatty acid glycerides such as vegetable or animal oil or fat or other mixtures of glycerides, the process comprises the following stages: (a) transesterifying fatty acid glycerides with hydrated ethyl alcohol using an alkaline catalyst to form a medium comprising ethyl esters and excess ethyl alcohol; (b) adding a glycerine phase to said medium, and evaporating the excess ethyl alcohol to produce two immiscible phases, an ester phase and a glycerine phase A, and recycling said excess ethyl alcohol to stage (a); (c) separating said glycerine phase A and said ester phase to obtain the desired ethyl esters; (d) neutralizing said glycerine phase A with acid, and separating resultant "fatty acids+esters" phase and a glycerine phase B, and drying the latter phase; (e) subjecting the "fatty acids+esters" phase to glycerolysis with at least a fraction of the dried glycerine phase B in the presence of an alkaline catalyst to form a mixture of glycerides and esters, and passing said mixture into transesterification stage (a).

摘要翻译： 为了从脂肪酸甘油酯如植物油或动物油或脂肪或甘油酯的其它混合物生产脂肪酸乙酯，该方法包括以下步骤：（a）使用碱性催化剂将脂肪酸甘油酯与水合乙醇酯交换成 形成包含乙酯和过量乙醇的介质; （b）向所述介质中加入甘油相，并蒸发过量的乙醇以产生两个不混溶相，酯相和甘油相A，并将所述过量的乙醇再循环到步骤（a）; （c）分离所述甘油相A和所述酯相以获得所需的乙酯; （d）用酸中和所述甘油相A，分离所得的“脂肪酸+酯”相和甘油相B，并干燥后一相; （e）在碱性催化剂存在下，使至少一部分干燥的甘油相B对“脂肪酸+酯”相进行甘油分解，形成甘油酯和酯的混合物，并将所述混合物通入酯交换反应阶段 ）。

公开(公告)号：US5434282A

公开(公告)日：1995-07-18

申请号：US231706

申请日：1994-04-22

申请人： Robert Stern ,  Gerard Hillion ,  Abakar Kotoko ,  Yves Chauvin

发明人： Robert Stern ,  Gerard Hillion ,  Abakar Kotoko ,  Yves Chauvin

IPC分类号： B01J31/22 ,  B01J31/24 ,  C07B61/00 ,  C07C51/353 ,  C07C51/36 ,  C07C53/126 ,  C07C57/03 ,  C07C67/303 ,  C07C67/347 ,  C07C69/24 ,  C07C69/30 ,  C07C69/533 ,  C07C69/587 ,  C10M105/24 ,  C10M105/34 ,  C10M105/38 ,  C07C67/03

CPC分类号： C07C69/587 ,  C07C51/353 ,  C07C53/126 ,  C07C67/347

摘要： A novel family of chemical compounds derived from fatty compounds has two branches of two carbon atoms on the linear chain and general formula C.sub.21 H.sub.39 COOR where R represents a hydrogen atom, a lower alkyl radical or a glyceryl radical. Particular compounds for consideration have the following formulae:(C.sub.2 H.sub.5).sub.2 C.sub.17 H.sub.29 COOR (I)(C.sub.2 H.sub.5)(C.sub.2 H.sub.4)C.sub.17 H.sub.30 COOR (II)and(C.sub.2 H.sub.5)(C.sub.2 H.sub.3)C.sub.17 H.sub.31 COOR (III)also compounds with the following formulae derived from partial or total hydrogenation of the above:(C.sub.2 H.sub.5).sub.2 C.sub.17 H.sub.31 COOR (IV)(C.sub.2 h.sub.5)(C.sub.2 h.sub.4)C.sub.17 H.sub.32 COOR (V)andti (C.sub.2 H.sub.5).sub.2 C.sub.17 H.sub.33 COOR (VI)Compounds with formulae (I), (II) and (III) may be produced by addition of ethylene to compositions comprising mainly diunsaturated C.sub.18 fatty acids; or to lower alkyl or glyceryl esters of these acids, originating in particular from natural oils, in the presence of a catalytic system containing anionic rhodium of the type [RhX.sub.4 ].sup.- YR'.sub.4 where X is preferably a halide anion; Y is a nitrogen N.sup.+ or phosphorous P.sup.+ atom and R.sup.' is preferably a hydrocarbon group.Compositions in accordance with the invention can be used as base compositions for lubricants or emulsifying agents.

摘要翻译： 衍生自脂肪族化合物的化学化合物的新型家族在直链上具有两个碳原子的分支，通式为C 21 H 39 COOR，其中R表示氢原子，低级烷基或甘油基。 考虑的具体化合物具有下式：（C 2 H 5）2 C 17 H 29 COOR（I）（C 2 H 5）（C 2 H 4）C 17 H 30 COOR（II）和（C 2 H 5）（C 2 H 3）C 17 H 31 COOR 上述:( C2H5）2C17H31COOR（Ⅳ）（C2h5）（C2h4）C17H32COOR（Ⅴ）和（C2H5）2C17H33COOR（VI）式（Ⅰ），（Ⅱ）和（Ⅲ）化合物可以通过加入乙烯 主要包含二不饱和C18脂肪酸的组合物; 或者在含有[RhX4] -YR'4类型的阴离子铑的催化体系存在下，将这些酸的烷基或甘油酯特别地衍生自天然油，其中X优选为卤化物阴离子; Y是氮N +或磷P +原子，R'优选为烃基。 根据本发明的组合物可用作润滑剂或乳化剂的基础组合物。

公开(公告)号：US5424466A

公开(公告)日：1995-06-13

申请号：US125824

申请日：1993-09-24

申请人： Robert Stern ,  Gerard Hillion ,  Jean-Jacques Rouxel

发明人： Robert Stern ,  Gerard Hillion ,  Jean-Jacques Rouxel

IPC分类号： C10L1/02 ,  C11B13/02 ,  C11C3/04 ,  C11C3/06 ,  C11B3/10

CPC分类号： C11C3/06 ,  C10L1/026 ,  C11C3/04 ,  Y02E50/13

摘要： A description is given of an improved process for the production of esters from fatty substances having a natural origin (animal and vegetable oils) and low molecular weight alcohols, in which the soaps and oily compounds entrained in the alkaline phases are recycled by treating them, following acidification and separation, with a fraction of the glycerol phase produced, in the presence of an alkaline catalyst and for forming preferably a triglyceride or a partly substituted glyceride.This process makes it possible to quantitatively obtain methyl, ethyl, propyl or butyl esters usable as a substitute for gas oil.

摘要翻译： 对由天然来源的脂肪物质（动植物油）和低分子量醇生产酯的改进方法进行了说明，其中通过处理它们将带在碱性相中的皂和油性化合物再循环， 在酸化和分离之后，在碱性催化剂存在下，产生一部分甘油相，并优选形成甘油三酯或部分取代的甘油酯。 该方法使得可以定量地获得可用作瓦斯油替代物的甲基，乙基，丙基或丁基酯。

公开(公告)号：US6153772A

公开(公告)日：2000-11-28

申请号：US121851

申请日：1998-07-24

申请人： Gerard Hillion ,  Helene Olivier ,  Katja Siepen ,  Robert Stern

发明人： Gerard Hillion ,  Helene Olivier ,  Katja Siepen ,  Robert Stern

IPC分类号： C07C67/347 ,  C07C2/08 ,  C07B37/02 ,  C07C2/38 ,  C11C3/12

CPC分类号： C07C67/347

摘要： A cobalt 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.

摘要翻译： 描述了一种钴催化体系，其可以通过在多不饱和酯上将单烯烃反应从脂肪物质中获得支链化合物，其可以或可以不共轭。 得到的化合物可以被氢化并用作润滑剂基质。

公开(公告)号：US6147196A

公开(公告)日：2000-11-14

申请号：US213286

申请日：1998-12-17

申请人： Robert Stern ,  Gerard Hillion ,  Jean-Jacques Rouxel

发明人： Robert Stern ,  Gerard Hillion ,  Jean-Jacques Rouxel

IPC分类号： C07C67/03 ,  C11C1/00

CPC分类号： C11C3/003 ,  C07C67/03

摘要： In order to produce a composition of esters of linear monocarboxylic acids containing 6 to 26 carbon atoms and glycerine simultaneously with high degrees of purity, the following is carried out:a step a) in which a plant or animal oil, which may or may not be acidic, is reacted with an excess of at least one aliphatic mono-alcohol containing 1 to 4 carbon atoms in the presence of a heterogeneous catalyst, eliminating the excess mono-alcohol and separating out glycerine, this step producing a crude ester containing residual mono-glycerides;a step b) in which the crude ester obtained undergoes transesterification or esterification of the residual mono-glycerides to di- and tri-glycerides, in the presence of a heterogeneous catalyst; anda step c) in which the ester composition is evaporated under reduced pressure, recycling the evaporation residue to the starting oil of step a). The ester compositions obtained, which are of high purity, are of particular use as gas oil substitutes.

摘要翻译： 为了以高纯度同时生产含有6至26个碳原子的直链单羧酸酯和甘油的组合物，进行以下操作：步骤a）其中植物或动物油可以或不可以 在多相催化剂存在下与过量的至少一种含有1至4个碳原子的脂肪族一元醇反应，除去过量的单醇并分离出甘油，该步骤产生含有残留单体的粗酯 甘油酯 步骤b）其中所得粗酯在多相催化剂存在下进行酯交换反应或将残留的单甘油酯酯化为二 - 和三 - 甘油酯; 和步骤c），其中酯组合物在减压下蒸发，将蒸发残余物再循环到步骤a）的起始油中。 获得的具有高纯度的酯组合物特别用作瓦斯油替代物。

公开(公告)号：US5908946A

公开(公告)日：1999-06-01

申请号：US908983

申请日：1997-08-08

申请人： Robert Stern ,  Gerard Hillion ,  Jean-Jacques Rouxel ,  Serge Leporq

发明人： Robert Stern ,  Gerard Hillion ,  Jean-Jacques Rouxel ,  Serge Leporq

IPC分类号： C07C67/03 ,  C10L1/02 ,  C11C3/10 ,  C07C51/00

CPC分类号： C11C3/003 ,  C07C67/03 ,  C10L1/02

摘要： For the production of linear monocarboxylic acid esters with 6 to 26 carbon atoms vegetable oils or animal oils, which may or may not be neutral, are reacted with monoalcohols having a low molecular weight, for example 1 to 5 carbon atoms, in the presence of a catalyst that is selected from among zinc oxide, mixtures of zinc oxide and aluminum oxide, and the zinc aluminates that correspond to the formula:ZnAl.sub.2 O.sub.4, x ZnO, y Al.sub.2 O.sub.3(with x and y each being in the range of 0-2) and having more particularly a spinel type structure, thereby enabling the direct production in one or more stages, of an ester that can be used as a fuel or combustible and a pure glycerine.

摘要翻译： 对于具有6至26个碳原子的线性单羧酸酯的生产，可以是或可以不是中性的植物油或动物油与具有低分子量，例如1-5个碳原子的一元醇在存在 选自氧化锌，氧化锌和氧化铝的混合物的催化剂和对应于下式的ZnAl 2 O 4，x ZnO，y Al 2 O 3（x和y各自在0-2范围内）的铝酸锌， 并且更具体地具有尖晶石型结构，从而能够在一个或多个阶段直接生产可用作燃料或可燃物的酯和纯甘油。