Abstract: There is disclosed a process for the separation of long chain amino acid and long chain dibasic acid, comprising: (1) adding an ammonium salt to the mixture of alkali salts of long chain amino acid and long chain dibasic acid; (2) heating to remove ammonia; and (3) separating long chain amino acid by solid-liquid separation; and (4) acidifying the salt of long chain dibasic acid with an acid to separate long chain dibasic acid.

Abstract: There is disclosed a process for the production of dodecanedioic acid and 11-aminoundecanoic acid, comprising: (1) reacting castor oil with a primary or secondary amine to form a amide; (2) isomerizing the amide in the presence of a catalyst to form ketoamide; (3) reacting the ketoamide with hydroxylamine to form the oximeamide; (4) subjecting the oximeamide to Beckmann rearrangement to yield a mixture of two diamides; and (5) hydrolyzing the mixed diamides to produce dodecanedioic acid, 11-aminoundecanoic acid, hexylamine and heptanoic acid.

Abstract: There is disclosed a process for the production of long chain amino acid and long chain dibasic acid, comprising: (1) reacting long chain keto fatty acid with hydroxylamine or subjecting keto fatty acid to an ammoximation reaction to yield an oxime fatty acid; (2) reacting the oxime fatty acid with an alcohol or a primary amine or a secondary amine to prepare an ester or amide; (3) subjecting the oxime fatty acid ester or amide to the Beckmann rearrangement to yield a mixture of two amide fatty acids; (4) hydrolyzing the mixed amide fatty acids to produce long chain amino acid, long chain dibasic acid, short chain alkylamine, and alkanoic acid.

Abstract: There is disclosed a process for the purification of long chain amino acids by recrystallization in an aqueous solution of organic carboxylic acid in the absence or presence of solvent, comprising: (1) dissolving a long chain amino acid in an aqueous solution of organic carboxylic acid by heating; (2) cooling the solution of step (1) to crystallize the long chain amino acid; and (3) recovering the long chain amino acid of step (2) by means of solid-liquid separation.

Abstract: There is disclosed a process for the separation of long chain dibasic acid and fatty acid, comprising: (1) reacting a mixture of long chain dibasic acid and fatty acid with ammonium hydroxide to form an insoluble ammonium salt of fatty acid and a soluble ammonium salt of long chain dibasic acid; (2) recovering the insoluble ammonium salt of fatty acid; and (3) adding an acid to the mother liquor of step (2) to obtain the long chain dibasic acid.

Abstract: There is disclosed a process for the purification of long chain amino acids by recrystallization in an aqueous solution of organic carboxylic acid in the absence or presence of solvent, comprising: (1) dissolving a long chain amino acid in an aqueous solution of organic carboxylic acid by heating; (2) cooling the solution of step (1) to crystallize the long chain amino acid; and (3) recovering the long chain amino acid of step (2) by means of solid-liquid separation.

Abstract: A concise method of producing nylon 11, 12, or 13 precursors from oleic acid or an ester of oleic acid is described. The method involves cross-metathesis reactions as the key C—C bond formation step. Subsequent steps are provided to convert the metathesis product to the corresponding nylon precursors. Also provided are the products of the method.

Abstract: There is disclosed a process for the production of long chain amino acid and long chain dibasic acid, comprising: (1) reacting long chain keto fatty acid with hydroxylamine or subjecting keto fatty acid to an ammoximation reaction to yield an oxime fatty acid; (2) subjecting the oxime fatty acid to the Beckmann rearrangement to yield a mixture of two amide fatty acids; (3) hydrolyzing the mixed amide fatty acids to produce long chain amino acid, long chain dibasic acid, short chain alkylamine, and alkanoic acid.

Abstract: There is disclosed a process for the separation of long chain amino acid and long chain dibasic acid, comprising: (1) mixing the mixed amide derivatives with an aqueous solution of ammonia or ammonium hydroxide in the presence or absence of solvent or catalyst; (2) subjecting the solution or suspension of step (1) to an hydrolysis reaction; and (3) recovering excess ammonia and solvent in the presence of solvent in step (1) by evaporation to provide a mixture of long chain amino acid and alkylamine or ammonium salts of long chain dibasic acid and alkanoic acid.

Abstract: There is disclosed a process for the separation of long chain amino acid and long chain dibasic acid, comprising: (1) adding water and an extractant solvent to the aqueous suspension of an acid hydrolysis of the mixed amide derivatives to yield an aqueous solution and an extractant phase; (2) separating the mixture of step (1) into an aqueous phase containing the acid salt of long chain amino acid and alkylamine and an extractant phase containing long chain dibasic acid, short chain alkanoic acid, and impurities; (3) neutralizing the aqueous phase of step (2) with a basic agent to obtain a crystalline suspension of the long chain amino acid; (4) recovering the long chain amino acid by solid-liquid separation to yield an aqueous mother liquor; and (5) in the extractant phase of step (2), separating the long chain dibasic acid, short chain alkanoic acid, and impurities.

Abstract: There is disclosed a process for the separation of long chain amino acid and long chain dibasic acid, comprising: (1) recovering alkylamine by distilling or by extracting with an extractant solvent; (2) adding an acid an extractant solvent to the aqueous solution of step (1) to form an acidic salt of long chain amino acid to extract long chain dibasic acid; (3) separating the mixture of step (2) into an aqueous phase and an extractant phase; (4) neutralizing the aqueous phase of step (3) with an alkali hydroxide or ammonium hydroxide to obtain a crystalline solid of long chain amino acid; (5) cooling the extractant phase of step (3) to crystallize the long chain dibasic acid and recovering the dibasic acid by solid-liquid separation; and (6) recovering the extractant solvent of step (5) and isolating the alkanoic acid by distillation.

Abstract: A method for producing a cationic lipid, wherein a cationic lipid represented by formula (1) is mixed with a tetraalkylammonium salt having X? in an organic solvent, and a filtrate obtained by separating a tetraalkylammonium iodide deposited by filtration is concentrated to deposit a tetraalkylammonium iodide, thereby obtaining a cationic lipid represented by formula (2): wherein R1 to R5 and X? are as defined herein.

Abstract: A method of synthesising an amino acid from an unsaturated fatty compound I that includes at least the following steps: cross-metathesis with a short unsaturated compound II, one of compounds I or II comprising a nitrile function and the other of these compounds II or I an ester function, so as to obtain and recover at least one monounsaturated nitrile ester NEU; hydrolysis of the NEU in unsaturated acid nitrile NAU; hydrogenation of the NAU to saturated amino acid AA; and then purification of the AA, if applicable, in particular by crystallisation. Also, a polymer obtained by polymerisation using the amino acid synthesised according to the method.

Abstract: The invention features a cationic lipid of formula I, an improved lipid formulation comprising a cationic lipid of formula I and corresponding methods of use. Also disclosed are targeting lipids, and specific lipid formulations comprising such targeting lipids.

Abstract: The present invention provides processes for producing amine compounds. The amine compounds include diammonium compounds and amino acid derivatives.

Abstract: The invention relates to a method for removing an organic compound having one or more positive charges from an aqueous solution. Said method consists of the following steps a) the aqueous solution containing the organic compound, and a hydrophobic organic solution which contains a hydrophobic liquid cation exchanger having one or more negative charges and a negative total charge, are provided, b) the aqueous solution and the organic solution are brought into contact with each other and c) the organic solution is separated from the aqueous solution.

Abstract: Described herein are nitrated lipids and methods of making and using the nitrated lipids.

Abstract: The invention is directed to methods of making organic compounds by metathesis and hydrocyanation. Hydrocyanation functions to introduce a nitrile group into the organic compound. The nitrile group may be converted into an amine group, an aldehyde group, an alcohol group, or a carboxylic acid group. The method of the invention may be used, for example, to make industrial important organic compounds such as diacids, diesters, acid-amines, acid-alcohols, acid-nitriles, ester-amines, ester-alcohols, and ester-nitriles.

Abstract: The present invention relates to a chemocatalytic liquid-phase process for the direct one-stage amination of alcohols to primary amines by means of ammonia in high yields using a catalyst system containing at least one transition metal compound and a xantphos ligand.

Abstract: The subject matter of the invention is a process for synthesizing ?-functionalized acids of formula R—(CH2)n—COOH in which R is COOH or NH2CH2, from a feedstock of natural origin containing hydroxylated fatty acids.

Abstract: A method for synthesizing ?-amino-alkanoic acids or the esters thereof from natural unsaturated fatty acids passing through an intermediate ?-unsaturated nitrile compound. The method is simple to implement and, relative to known methods, avoids the environmental constraints and economic disadvantages resulting from the reaction by-products. The method includes synthesizing an ?-amino acid (ester) of formula R3OOC—(CH2)q-CH2NH2, in which R3 is H or an n-butyl radical and q is an integral index of between 2 and 13, from a monounsaturated fatty acid (ester) of formula (R1-CH?CH—(CH2)p-COO)xR2, in which x represents 1, 2 or 3, R1 is H or a hydrocarbon radical comprising from 4 to 11 carbon atoms and, where appropriate, a hydroxyl function, R2 is H or an alkyl radical comprising from 2 to 4 carbon atoms, and may contain one or more heteroatoms, and p is an integral index of between 2 and 11, including a reaction step of ammoniation.

Abstract: Chemically-modified fatty acids are prepared by reacting epoxidized fatty acids, their esters or triglyceride oils with amines of cyclic or aromatic hydrocarbons. The fatty acid derivatives produced are of the formula: wherein R is an H, branched or straight chain alkyl or alkenyl group, aromatic-containing group, glycerol, or glyceride, R? is a C3 to C29 aliphatic chain comprising one or more of the derivatized methylene groups of the formula: wherein R1 and R2 are independently selected from the group consisting of H, cyclic hydrocarbons, substituted cyclic hydrocarbons, and aryl groups, with the proviso that only one of said R1 and R2 may be H. These fatty acid derivatives have utility as antiwear/antifriction additives for industrial oils and automotive applications.

Abstract: A process for the synthesis of C11 and C12 ?-amino-alkanoic acid esters including a step of continuous nitrilation in the gas phase or in a mixed gas-liquid phase, a step of metathesis and a step of reduction by hydrogenation, using, as raw material, C10 and C11 ?-alkenoic acid esters.

Abstract: A method for synthesizing ?-amino-alkanoic acids or the esters thereof from natural unsaturated fatty acids passing through an intermediate ?-unsaturated nitrile compound. The method is simple to implement and, relative to known methods, avoids the environmental constraints and economic disadvantages resulting from the reaction by-products. The method includes synthesizing an ?-amino acid (ester) of formula R3OOC—(CH2)q—CH2NH2, in which R3 is H or an n-butyl radical and q is an integral index of between 2 and 13, from a monounsaturated fatty acid (ester) of formula (R1-CH?CH—(CH2)p-COO) xR2, in which x represents 1, 2 or 3, R1 is H or a hydrocarbon radical comprising from 4 to 11 carbon atoms and, where appropriate, a hydroxyl function, R2 is H or an alkyl radical comprising from 2 to 4 carbon atoms, and may contain one or more heteroatoms, and p is an integral index of between 2 and 11, including a reaction step of ammoniation.

Abstract: A process for synthesizing a long-chain saturated ?,?-amino ester (acid) including from 6 to 17 carbon atoms, said process including a first step of cross metathesis between a first acrylic compound chosen from acrylonitrile, acrylic acid or an acrylic ester and a second monounsaturated compound including at least one nitrile, acid or ester trivalent function, one of these compounds including a nitrile function and the other an acid or ester function, in the presence of a ruthenium carbene metathesis catalyst, and a second step of hydrogenation of the monounsaturated nitrile-ester (acid) obtained, wherein said monounsaturated compound including at least one nitrile, acid or ester trivalent function has previously been subjected to a purification by thermal and/or chemical treatment.

Abstract: The subject matter of the invention is a process for synthesizing ?-functionalized acids of formula R—(CH2)n—COOH in which R is COOH or NH2CH2, from a feedstock of natural origin containing hydroxylated fatty acids.

Abstract: Provided are methods for decreasing the reaction time between an alkanolamine such as triethanolamine and a fatty acid alkyl ester such as, a triglyceride, a vegetable oil, a methyl ester, an ethyl ester, etc., a fatty acid, or a mixture thereof. The methods utilize a divalent zinc catalyst to facilitate and accelerate an esterification or transesterification reaction between the alkanolamine and the fatty acid, or fatty acid alkyl ester.

Abstract: The invention relates to a method for removing an organic compound having one or more positive charges from an aqueous solution. Said method consists of the following steps a) the aqueous solution containing the organic compound, and a hydrophobic organic solution which contains a hydrophobic liquid cation exchanger having one or more negative charges and a negative total charge, are provided, b) the aqueous solution and the organic solution are brought into contact with each other and c) the organic solution is separated from the aqueous solution.

Abstract: The invention relates to a method for the synthesis of amino acids/esters of general formula NH2—(CH2)n—COOR in which n is an integer between 5 and 14, and R is either H or an alkyl radical including from 1 to 4 carbon atoms, from natural long-chain mono-unsaturated fatty acids or esters including at least 10 adjacent carbon atoms per molecule, said method comprising: first converting, if necessary, said natural long-chain fatty acid or ester into a monounsaturated fatty acid/ester of general formula R1—(CH2)m—CH?CH—(CH2)p—COOR in which R1 is H, CH3 or a COOR radical, m is an integer between 0 and 14 and p is an integer between 2 and 11, then submitting the latter to a crossed catalytic metathesis reaction with a compound of formula R2—CH?CH—R3 in which R2 is either H or CN and R3 is CN or CH2NH2, provided that if R2 is CN, R3 can be only CN, and finally converting the resulting product of the general formula R3—CH?CH—(CH2)p—COOR into an amino-acid, either by hydrogenation, or by hydrogenation of the triple t

Abstract: The invention relates to a process for synthesizing a nitrile-fatty acid (heminitrile) from unsaturated fatty acids, in the form of an acid or a simple ester or a “complex” ester of triglyceride type, which is first of all converted into an unsaturated fatty nitrile which is subjected to oxidative cleavage using H2O2 as oxidizing agent. This process can be used for preparing polyamide monomers, such as ?-amino acids or diamines or diacids equivalent to said heminitrile and for obtaining polyamides from raw materials which are of natural origin and from a renewable source.

Abstract: The present invention relates to a chemocatalytic liquid-phase process for the direct one-stage amination of alcohols to primary amines by means of ammonia in high yields using a catalyst system containing at least one transition metal compound and a xantphos ligand.

Abstract: The present invention relates to a process for preparing primary amines comprising the process steps A) provision of a solution of a primary alcohol in a fluid, nongaseous phase, B) contacting of the phase with free ammonia and/or at least one ammonia-releasing compound and a homogeneous catalyst and optionally C) isolation of the primary amine formed in process step B), characterized in that the volume ratio of the volume of the liquid phase to the volume of the gas phase in process step B is greater than 0.05 and/or in that process step B is carried out at pressures greater than 10 bar.

Abstract: The invention relates to a method for producing a mixture containing hydroxy- and aldehyde functional compounds by a cross-metathesis reaction of at least one at least monounsaturated fatty acid or at least one at least monounsaturated fatty acid derivative with an olefinic compound having at least one hydroxy group and at least one C—C double bond, in the presence of a metathesis catalyst at a maximum temperature of 180° C.

Abstract: The invention relates to a method for synthesizing 9-aminononanoic acid or the esters thereof from natural unsaturated fatty acids, comprising at least one step of metathesis of the natural fatty acid and an oxidation step by oxidative cleaving. Said synthetic method uses widely available renewable starting materials and hence economical.

Abstract: The subject matter of the invention is a process for synthesizing a saturated long-chain o.,0)-amino ester (acid) obtained in a first step by cross-metathesis between an acrylic first compound and a monounsaturated second compound comprising at least one nitrile, acid or ester trivalent function, one of these compounds comprising a nitrile function and the other an acid or ester function, in the presence of a ruthenium carbene metathesis catalyst, and in a second step by hydrogenation of the monounsaturated nitrile ester (acid) obtained in the presence of the metathesis catalyst of the preceding stop, acting as a hydrogenation catalyst.

Abstract: The invention relates to a process for the ammonolysis of 11-aminoundecanoic acid, carried out under conditions that make it possible to limit secondary reactions that produce impurities, especially secondary amine type reactions, while considerably reducing the reaction time. According to the invention, the process comprises the following steps: i) a step of dispersing 11-bromoundecanoic acid, molten or non-molten, in an aqueous solution of ammonia, and ii) an ammonolysis step comprising the reaction of 11-bromoundecanoic acid with excess ammonia water under conditions whereby the reaction medium is stirred and heated gradually so as to obtain 11-aminoundecanoc acid with total consumption of the 11-bromoundecanoic acid.

Abstract: The invention relates to novel quaternary ammonium compounds of the esterquat type, to a method for the production thereof, and to the use thereof in formulations.

Abstract: The invention relates to a method for producing aldehyde functional compounds by a cross-metathesis reaction of an olefinic compound having at least one hydroxy group and at least one C—C double bond with at least one at least monounsaturated fatty acid or at least one at least monounsaturated fatty acid derivative, in the presence of a metathesis catalyst at a maximum temperature of 180° C. and in the presence of at least one reagent that acts as a protective group-forming compound in relation to the aldehyde group of the aldehyde functional compounds.

Abstract: Provided are methods for decreasing the reaction time between an alkanolamine such as triethanolamine and a fatty acid alkyl ester such as, a triglyceride, a vegetable oil, a methyl ester, an ethyl ester, etc., a fatty acid, or a mixture thereof The methods utilize a divalent zinc catalyst to facilitate and accelerate an esterification or transesterification reaction between the alkanolamine and the fatty acid, or fatty acid alkyl ester.

Abstract: The invention relates to a method for producing aldehyde functional compounds by a cross-metathesis reaction of an olefinic compound having at least one hydroxy group and at least one C—C double bond with at least one at least monounsaturated fatty acid or at least one at least monounsaturated fatty acid derivative, in the presence of a metathesis catalyst at a maximum temperature of 180° C. and in the presence of at least one reagent that acts as a protective group-forming compound in relation to the aldehyde group of the aldehyde functional compounds.

Abstract: The invention relates to a process for the ammonolysis of 11-aminoundecanoic acid, carried out under conditions that make it possible to limit secondary reactions that produce impurities, especially secondary amine type reactions, while considerably reducing the reaction time. According to the invention, the process comprises the following steps: i) a step of dispersing 11-bromoundecanoic acid, molten or non-molten, in an aqueous solution of ammonia, and ii) an ammonolysis step comprising the reaction of 11-bromoundecanoic acid with excess ammonia water under conditions whereby the reaction medium is stirred and heated gradually so as to obtain 11-aminoundecanoc acid with total consumption of the 11-bromoundecanoic acid.

Abstract: The invention relates to a method for synthesizing 9-aminononanoic acid or the esters thereof from natural unsaturated fatty acids, comprising at least one step of metathesis of the natural fatty acid and an oxidation step by oxidative cleaving. Said synthetic method uses widely available renewable starting materials and hence economical.

Abstract: The present invention relates to drugs consisting of unsaturated fatty amino-acid derivatives of the general formula (I), and to their pharmaceutically acceptable acid addition salts, in which: X is oxygen or NH, Rn are independently hydrogen or a (C1-C6)alkyl optionally substituted by halogen; R1 is hydrogen, fluorine, chlorine or bromine, or a CF3 or CHF2 or a (C1-C6)alkyl, (C1-C6)alkenyl or (C1-C6)alkynyl, optionally substituted by one or more halogen atoms; R is hydrogen or a (C1-C6)alkyl or (C3-C6)cycloalkyl optionally substituted by one or more halogen atoms; Ra and Rb are independently hydrogen (C1-C6)alkyl or (C1-C6)acyl, and Ra and Rb a hydrocarbonated cycle containing 4 to 6 carbon atoms; and n is an integer between 2 and 14.

Abstract: A process for preparing esterquats with asymmetric side chains, including the steps of: (a) reacting one or more alkanolamines with a mixture, including: (i) 30:70% b.w. of one or more C6-C10 monocarboxylic acids, and (ii) 70:30% b.w. of one or more C12-C22 monocarboxylic acids, and (b) quaternizing the resulting esters with one or more alkylation agents is provided. A process for preparing esterquats with asymmetric side chains, including the steps of: esterifying a mixture of carboxylic acids with one or more alkanolamines to form a mixture of mono-, di- and trialkanolamine esters, where the mixture of carboxylic acids comprises (i) 30:70% b.w. of one or more C6-C10 monocarboxylic acids, and (ii) 70:30% b.w. of one or more C12-C22 monocarboxylic acids; and quaternizing the esters with one or more alkylation agents is also provided.

Abstract: Described herein are nitrated lipids and methods of making and using the nitrated lipids.

Abstract: The invention relates to a method for the synthesis of amino acids/esters of general formula NH2—(CH2)n—COOR in which n is an integer between 5 and 14, and R is either H or an alkyl radical including from 1 to 4 carbon atoms, from natural long-chain mono-unsaturated fatty acids or esters including at least 10 adjacent carbon atoms per molecule, said method comprising: first converting, if necessary, said natural long-chain fatty acid or ester into a monounsaturated fatty acid/ester of general formula R1—(CH2)m—CH?CH—(CH2)p—COOR in which R1 is H, CH3 or a COOR radical, m is an integer between 0 and 14 and p is an integer between 2 and 11, then submitting the latter to a crossed catalytic metathesis reaction with a compound of formula R2—CH?CH—R3 in which R2 is either H or CN and R3 is CN or CH2NH2, provided that if R2 is CN, R3 can be only CN, and finally converting the resulting product of the general formula R3—CH?CH—(CH2)p—COOR into an amino-acid, either by hydrogenation, or by hydrogenation of the triple t

Abstract: The present invention relates to a process for producing (2R)-2-propyloctanoic acid, which comprises subjecting (2R)-2-hexyloxirane to a two-carbon adding reaction with ring-opening reaction, followed by a protecting reaction of a hydroxyl group to convert it to a compound represented by formula (I): (wherein X represents an optionally protected hydroxyl group) and then subjecting the compound to a one-carbon adding reaction to convert it to (2R)-2-propyloctanamide, followed by recrystallization and hydrolysis. According to the process of the present invention, (2R)-2-propyloctanoic acid can be produced by less steps as compared with the conventional method without a dangerous reaction.

Abstract: Disclosed relates to a method for improving a conversion rate of oil soluble unsaturated lipids into water-soluble lipids and, more particularly, to a method for improving a conversion rate of oil soluble unsaturated lipids into water-soluble lipids that forms an unsaturated lipid-chloride derivative having an increased reaction activity by using a pyridine-thionyl chloride as a catalyst, not directly causing a reaction between the unsaturated lipids and amino acids, or that applies an emulsifier to cause a reaction between the unsaturated lipids and amino acids so as to minimize the size of lipid particles to a nano-size of less than 50 nm, thus improving the reaction conversion rate to more than 99%.

Abstract: A process for preparing esterquats with asymmetric side chains, including the steps of: (a) reacting one or more alkanolamines with a mixture, including: (i) 30:70% b.w. of one or more C6-C10 monocarboxylic acids, and (ii) 70:30% b.w. of one or more C12-C22 monocarboxylic acids, and (b) quaternizing the resulting esters with one or more alkylation agents is provided. A process for preparing esterquats with asymmetric side chains, including the steps of: esterifying a mixture of carboxylic acids with one or more alkanolamines to form a mixture of mono-, di- and trialkanolamine esters, where the mixture of carboxylic acids comprises (i) 30:70% b.w. of one or more C6-C10 monocarboxylic acids, and (ii) 70:30% b.w. of one or more C12-C22 monocarboxylic acids; and quaternizing the esters with one or more alkylation agents is also provided.

Abstract: Disclosed are improved methods for the synthesis of N-(8-[2-hydroxybenzoyl]-amino)caprylic acid. Certain compounds have been found useful for preventing the formation of a colored impurity when included in an ester hydrolysis reaction. Conducting ester hydrolysis in anaerobic conditions has also been found to minimize the formation of the color impurity. Also disclosed are improved methods for synthesizing the sodium salt of N-(8-[2-hydroxybenzoyl]-amino)caprylic acid.