AR085717A1 - PROCESS TO PRODUCE ADIPIC ACID AND DIESTERS OF THE SAME IN A CARBONILATION PROCESS USING LIGANDOS BIFOSFATO BIDENTADOS DE PALADIO - Google Patents

PROCESS TO PRODUCE ADIPIC ACID AND DIESTERS OF THE SAME IN A CARBONILATION PROCESS USING LIGANDOS BIFOSFATO BIDENTADOS DE PALADIO

Info

Publication number
AR085717A1
AR085717A1 ARP120101032A AR085717A1 AR 085717 A1 AR085717 A1 AR 085717A1 AR P120101032 A ARP120101032 A AR P120101032A AR 085717 A1 AR085717 A1 AR 085717A1
Authority
AR
Argentina
Prior art keywords
pentenoate
methyl
optionally substituted
formula
independently represent
Prior art date
Application number
Other languages
Spanish (es)
Inventor
Sereinig Natascha
Gerardus De Vries Johannes
Catherine Christianne Janssen Michele
Wilhelmina Maria Van De Vondervoort Elisabeth
Original Assignee
Dsm Ip Assets Bv
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dsm Ip Assets Bv filed Critical Dsm Ip Assets Bv
Publication of AR085717A1 publication Critical patent/AR085717A1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
    • C07C209/48—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/10—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
    • C07C51/14—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on a carbon-to-carbon unsaturated bond in organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/31—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/41—Preparation of salts of carboxylic acids
    • C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/36—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates
    • C07C67/38—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates by addition to an unsaturated carbon-to-carbon bond

Abstract

La presente se relaciona con un proceso de carbonilación para la preparación de un compuesto de fórmula (1): XOOC-(CH₂)₄-COOY (1) en donde X e Y pueden representar independientemente H y/o alquilo, dicho proceso de carbonilación comprendiendo la reacción de: (a) una composición que contiene al menos un metil pentenoato isomérico; (b) una fuente de Pd; (c) una difosfina bidentada de fórmula (2): R¹R²P-R³-R-R⁴-PR⁵R⁶ (2) en donde P representa un átomo de fósforo; R¹, R², R⁵ y R⁶ pueden representar independientemente los mismos grupos orgánicos o diferentes opcionalmente sustituidos que contienen un átomo de carbono terciario a través del cual el grupo está enlazado al átomo de fósforo; R³ y R⁴ representan independientemente opcionalmente grupos alquileno inferiores sustituidos; y R representa un grupo aromático opcionalmente sustituido; (d) una fuente de aniones derivada de un ácido con un pKa < 3; (e) monóxido de carbono; y (f) un compuesto que contiene un grupo OH, bajo condiciones en donde se produce el compuesto de fórmula (1), caracterizado porque al menos un metil pentenoato isomérico contiene metil 2-pentenoato. El proceso que tiene convenientemente una tasa alta de conversión y puede ser utilizado sin necesidad de separar el metil 2-pentenoato de las mezclas también contiene metil 3- y/o 4-pentenoato con el propósito de isomerizar el metil 2-pentenoato. El proceso es adecuado para la producción de adipato de dimetilo, ácido adípico y hexametilén diamina y productos derivados de los mismos tales como nylon 6,6 de fuentes renovables tales como residuos vegetales, aguas residuales, etc. en vez de utilizar fuentes fósiles.This relates to a carbonylation process for the preparation of a compound of formula (1): XOOC- (CH₂) CO-COOY (1) wherein X and Y can independently represent H and / or alkyl, said carbonylation process the reaction comprising: (a) a composition containing at least one isomeric methyl pentenoate; (b) a source of Pd; (c) a bidentate diphosphine of formula (2): R¹R²P-R³-R-R⁴-PR⁵R⁶ (2) wherein P represents a phosphorus atom; R¹, R², R⁵ and R⁶ can independently represent the same or different optionally substituted organic groups containing a tertiary carbon atom through which the group is linked to the phosphorus atom; R³ and R⁴ independently represent optionally substituted lower alkylene groups; and R represents an optionally substituted aromatic group; (d) a source of anions derived from an acid with a pKa <3; (e) carbon monoxide; and (f) a compound containing an OH group, under conditions where the compound of formula (1) is produced, characterized in that at least one isomeric methyl pentenoate contains methyl 2-pentenoate. The process that conveniently has a high conversion rate and can be used without separating the methyl 2-pentenoate from the mixtures also contains methyl 3- and / or 4-pentenoate for the purpose of isomerizing the methyl 2-pentenoate. The process is suitable for the production of dimethyl adipate, adipic acid and hexamethylene diamine and products derived therefrom such as nylon 6,6 from renewable sources such as plant residues, wastewater, etc. instead of using fossil sources.

ARP120101032 2011-04-01 2012-03-27 PROCESS TO PRODUCE ADIPIC ACID AND DIESTERS OF THE SAME IN A CARBONILATION PROCESS USING LIGANDOS BIFOSFATO BIDENTADOS DE PALADIO AR085717A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201161470652P 2011-04-01 2011-04-01
EP11160909 2011-04-01

Publications (1)

Publication Number Publication Date
AR085717A1 true AR085717A1 (en) 2013-10-23

Family

ID=44146292

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP120101032 AR085717A1 (en) 2011-04-01 2012-03-27 PROCESS TO PRODUCE ADIPIC ACID AND DIESTERS OF THE SAME IN A CARBONILATION PROCESS USING LIGANDOS BIFOSFATO BIDENTADOS DE PALADIO

Country Status (2)

Country Link
AR (1) AR085717A1 (en)
WO (1) WO2012131028A1 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017135898A1 (en) * 2016-02-02 2017-08-10 Agency For Science, Technology And Research Process for preparing mono and dicarboxylic acids

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2368366A (en) 1942-08-21 1945-01-30 Monsanto Chemicals Process for the production of lactones
US3065263A (en) 1959-11-17 1962-11-20 Rayonier Inc Process for the manufacture of levulinic acid
DE3609139A1 (en) 1986-03-19 1987-09-24 Basf Ag METHOD FOR PRODUCING 4-PENTENIC ACID ESTERS
US4897497A (en) 1988-04-26 1990-01-30 Biofine Incorporated Lignocellulose degradation to furfural and levulinic acid
FR2684099B1 (en) * 1991-11-21 1994-10-28 Rhone Poulenc Chimie PROCESS FOR THE PREPARATION OF ALKYL ADIPATES.
US5608105A (en) 1995-06-07 1997-03-04 Biofine Incorporated Production of levulinic acid from carbohydrate-containing materials
US6706912B2 (en) 2000-03-14 2004-03-16 Shell Oil Company Process for the carbonylation of ethylenically unsaturated compounds
DE10060313A1 (en) 2000-12-04 2002-06-13 Basf Ag Process for the carbonylation of pentenoic acid and its derivatives
CZ20031616A3 (en) 2000-12-11 2004-01-14 E. I. Du Pont De Nemours And Company Process for preparing 5-cyanovaleric acid, adipic acid or dimethyladipate
US6835849B2 (en) 2002-07-15 2004-12-28 E. I. Du Pont De Nemours And Company Synthesis of alkenoate esters from lactones and alcohols
US20070142664A1 (en) 2003-12-19 2007-06-21 Shell Oil Company Process for the preparation of an alkyl alkenoate
WO2006125801A1 (en) 2005-05-27 2006-11-30 Shell Internationale Research Maatschappij B.V. Process for the preparation of adipic acid from n-pentenoic acid
GB0713624D0 (en) 2007-07-13 2007-08-22 Lucite Int Uk Ltd Improved solvent for catalyst system

Also Published As

Publication number Publication date
WO2012131028A1 (en) 2012-10-04

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