ES2613722T3 - Éster vinílico de ácido de isononano obtenido a partir de 2-etilohexanol, método para su producción, así como su uso - Google Patents

Éster vinílico de ácido de isononano obtenido a partir de 2-etilohexanol, método para su producción, así como su uso Download PDF

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ES2613722T3
ES2613722T3 ES13730491.1T ES13730491T ES2613722T3 ES 2613722 T3 ES2613722 T3 ES 2613722T3 ES 13730491 T ES13730491 T ES 13730491T ES 2613722 T3 ES2613722 T3 ES 2613722T3
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Prior art keywords
ethylhexanol
vinyl ester
mixture
production
isononanic
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Leif Johnen
Guido D. Frey
Matthias Eisenacher
Kristina KOCKRICK
Heinz Strutz
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OQ Chemicals GmbH
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Oxea GmbH
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
    • C07C1/24—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by elimination of water
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
    • C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
    • 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
    • C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
    • 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
    • C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
    • C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
    • C07C51/235—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups of —CHO groups or primary alcohol groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/62—Monocarboxylic acids having ten or more carbon atoms; Derivatives thereof
    • C08F220/68—Esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
    • C07C2521/02—Boron or aluminium; Oxides or hydroxides thereof
    • C07C2521/04—Alumina
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
    • C07C2521/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
    • C07C2521/08—Silica
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
    • C07C2523/74—Iron group metals
    • C07C2523/755—Nickel
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/14—Phosphorus; Compounds thereof
    • C07C2527/16—Phosphorus; Compounds thereof containing oxygen
    • C07C2527/167—Phosphates or other compounds comprising the anion (PnO3n+1)(n+2)-
    • C07C2527/173—Phosphoric acid or other acids with the formula Hn+2PnO3n+1

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)

Abstract

Método para la producción de un éster vinílico de una mezcla de ácidos de isononano obtenido a partir de 2- etilohexanol, que se caracteriza por que (a) 2-etilohexanol se deshidrata en presencia de un catalizador a una mezcla de octeno; (b) la mezcla de octeno obtenida según el paso a) se transforma en presencia de un compuesto de metal de transición del grupo VIII del sistema periódico de los elementos con monóxido de carbono e hidrogeno a una mezcla de isononanales isoméricos y a continuación se oxida a una mezcla de ácidos de isononanos, y (c) la mezcla obtenida según el paso b) de ácidos de isononano se transforma al correspondiente éster vinílico mediante la transformación de acetilos o mediante la transformación con un éster vinílico de otro ácido carbónico.

Description

imagen1
imagen2
imagen3
imagen4
imagen5
imagen6
imagen7
imagen8
de 2-etilohexanol están indicados en la siguiente tabla 1. Antes del empleo, el octeno en bruto se destiló en un puente de Claisen para la separación de la cola a una temperatura de cabeza de 119-122ºC y a una presión normal. El octeno empleado, así como los productos de reacción obtenidos fueron analizados por vía cromatográfica en fase gaseosa (referencias en Fl.-%, según DIN 51405).
Tabla 1: Hidroformilación de octenos, obtenidos mediante la deshidratación de 2-etilohexanol
Ejemplo
IIa IIb
Empleo educto
destilado destilado
Análisis cromatógrafo de gas Educto (%)
Cabeza/Hidrógeno carburado C4-C7
0,3 0,4
Otras olefinas C8
5,9 7,7
2-etilo-1-hexeno
9,3 9,2
cis-3-metilo-3-hepteno
15,2 15,0
trans-3-metilo-3-hepteno
27,4 27,1
cis-3-metilo-2-hepteno
16,1 15,6
trans-3-metilo-2-hepteno
25,2 24,7
n-octeno
0,5 0,2
Cola
0,1 0,1
Condiciones del ensayo
Concentración Rh [ppm], referido al empleo de octeno
20 10
Presión [MPa]
19 27
Temperatura [ºC]
140 140
Tiempo de reacción [h]
2 2
Análisis cromatógrafo de gas Producto (%)
Cabeza
0,1 0,1
Hidrógeno carburado C8
2,5 1,1
Fase intermedia
0,3 0,1
iso-nonanales
90,8 94,7
n-nonanal
2,0 1,4
Cola
4,3 2,6
(0067) Los ensayos de hidroformilación llevados a cabo usando fosfina de trifenilo como ligandos complejos con el
10 octeno obtenido a través de la deshidratación de 2-etilohexanol están expuestos en la siguiente tabla 2. Se empleó un producto no destilado. Los octenos empleados, así como los productos de reacción obtenidos fueron analizados por vía cromatográfica en fase gaseosa (referencias en Fl.-%, según DIN 51405).
Tabla 2: Hidroformilación de octenos, obtenidos mediante la deshidratación de 2-etilohexanol, adición de fosfina de 15 trifenilo
Ejemplo
IIc IId lle llf
Empleo Educto
No destilado, en bruto No destilado, en bruto No destilado, en bruto No destilado, en bruto
Análisis cromatógrafo de gas Educto (%)
Hidrógeno carburado C4-C7
0,3 0,3 0,3 0,4
Otras olefinas C8
19,1 19,1 19,1 11,6
2-etilo-1-hexeno
7,9 7,9 7,9 8,6
3-metilo-3-hepteno
36,5 36,5 36,5 40,0
3-metilo-2-hepteno
36,2 36,2 36,2 39,3
Cola
<0,01 <0,01 <0,01 0,1
Condiciones del ensayo
Concentración Rh [ppm], referido al empleo de octeno
10 10 10 10
Equivalente TPP
3 50 100 3
Presión [MPa]
18 27 18 14
Temperatura [ºC]
140 140 140 160
Tiempo de reacción [h]
1 2 1 2
Análisis cromatógrafo de gas Producto (%)
Cabeza
0,1 0,1 0,1 0,1
Hidrógeno carburado C8
52,2 70,9 81,7 14,1
Fase intermedia
0,8 0,1 0,1 1,9
Iso-nonanales
45,7 28,3 17,6 76,1
n-nonanal
0,5 0,1 0,1 0,5
Cola
0,7 0,4 0,4 7,3
10
imagen9
imagen10
imagen11
imagen12
imagen13

Claims (1)

  1. imagen1
ES13730491.1T 2012-07-13 2013-06-19 Éster vinílico de ácido de isononano obtenido a partir de 2-etilohexanol, método para su producción, así como su uso Active ES2613722T3 (es)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE102012014396 2012-07-13
DE102012014396.6A DE102012014396B4 (de) 2012-07-13 2012-07-13 Verfahren zur Herstellung eines Vinylestergemisches aus einem Gemisch stellungsisomerer aliphatischer Isononansäuren ausgehend von 2-Ethylhexanol
PCT/EP2013/001803 WO2014008977A1 (de) 2012-07-13 2013-06-19 Vinvlester der isononansäure ausgehend von 2-ethvlhexanol, verfahren zu seiner herstellung sowie seine verwendung

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ES2613722T3 true ES2613722T3 (es) 2017-05-25

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Country Link
US (1) US9334225B2 (es)
EP (1) EP2872478B1 (es)
JP (1) JP6153271B2 (es)
KR (1) KR20150030239A (es)
CN (1) CN104411675B (es)
DE (1) DE102012014396B4 (es)
ES (1) ES2613722T3 (es)
PL (1) PL2872478T3 (es)
TW (1) TWI452034B (es)
WO (1) WO2014008977A1 (es)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102012013969B4 (de) * 2012-07-13 2017-09-14 Oxea Gmbh Verfahren zur Herstellung eines Gemisches stellungsisomerer aliphatischer Isononansäuren ausgehend von 2-Ethylhexanol
DE102012013968A1 (de) * 2012-07-13 2014-04-03 Oxea Gmbh Carbonsäureester der Isononansäure ausgehend von 2-Ethylhexanol, Verfahren zu ihrer Herstellung sowie ihre Verwendung
CN111470962A (zh) * 2020-04-28 2020-07-31 浙江师范大学 一种由混合异构辛烯制备异壬酸的方法

Family Cites Families (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB313426A (en) 1928-03-08 1929-06-10 Ig Farbenindustrie Ag Improvements in carrying out organic dehydration reactions
US2468764A (en) 1941-05-26 1949-05-03 Laurent Pierre Alfred Method for dehydrating amyl alcohols
DE950007C (de) 1951-09-26 1956-10-04 Basf Ag Verfahren zur Herstellung von ª‡-verzweigten gesaettigten Carbonsaeuren
US2919973A (en) 1956-10-18 1960-01-05 William D Stillwell Method of preparing catalytically active alumina
US3527809A (en) 1967-08-03 1970-09-08 Union Carbide Corp Hydroformylation process
US4148830A (en) 1975-03-07 1979-04-10 Union Carbide Corporation Hydroformylation of olefins
DE2604545C3 (de) 1976-02-06 1978-08-17 Basf Ag, 6700 Ludwigshafen Verfahren zur Herstellung von Alkylcarbonsäuren
US4247486A (en) 1977-03-11 1981-01-27 Union Carbide Corporation Cyclic hydroformylation process
US4283562A (en) 1979-10-26 1981-08-11 Union Carbide Corporation Hydroformylation process using stable rhodium catalyst
US5210207A (en) 1991-01-31 1993-05-11 Union Carbide Chemicals & Plastics Technology Corporation Transvinylation process by reactive distillation
ZA933123B (en) 1992-05-06 1993-11-30 Shell Res Ltd Saturated, monocarboxylic acids, the preparation thereof, and derivatives therefrom
MY130983A (en) * 1996-10-15 2007-07-31 Shell Int Research A process for the preparation of vinylesters
DE19906518A1 (de) 1999-02-17 2000-08-31 Oxeno Olefinchemie Gmbh Verfahren zur Fraktionierung von Dibuten
DE19908320A1 (de) 1999-02-26 2000-08-31 Oxeno Olefinchemie Gmbh Verfahren zur Herstellung von Vinylestern aus Butenoligomeren
DE19925385A1 (de) 1999-06-02 2000-12-07 Oxeno Olefinchemie Gmbh Verfahren zur katalytischen Durchführung von Mehrphasenreaktionen, insbesondere Vinylierungen von Carbonsäuren
DE19940991B4 (de) 1999-08-28 2007-04-05 Celanese Chemicals Europe Gmbh Verfahren zur Herstellung von Esterweichmachern
DE10010771C1 (de) 2000-03-04 2001-05-03 Celanese Chem Europe Gmbh Verfahren zur Herstellung aliphatischer Carbonsäuren aus Aldehyden
JP2002322127A (ja) * 2001-04-26 2002-11-08 Japan Vam & Poval Co Ltd カルボン酸ビニルエステルの製造方法
EP1281700A1 (en) 2001-07-31 2003-02-05 Resolution Research Nederland B.V. Manufacturing process for the preparation of alpha, alpha-branched alkane carboxylic acids providing esters with an improved softness
AU2002327859B2 (en) * 2001-09-26 2007-08-09 Evonik Degussa Gmbh Phthalic acid alkylester mixtures with controlled viscosity
US9051419B2 (en) * 2002-06-14 2015-06-09 Richard H. Hall Polymer
US6774093B2 (en) 2002-07-12 2004-08-10 Hatco Corporation High viscosity synthetic ester lubricant base stock
DE102004055252A1 (de) * 2004-11-16 2006-05-24 Celanese Chemicals Europe Gmbh Verfahren zur Herstellung von aliphatischen geradkettigen und ß-alkylverzweigten Carbonsäuren
DE102006022168B4 (de) 2006-05-12 2014-02-27 Oxea Gmbh Katalytisches Verfahren zur Herstellung von aliphatischen geradkettigen und ß-alkylverzweigten Carbonsäuren
WO2010093208A2 (ko) 2009-02-12 2010-08-19 (주) 엘지화학 하이드로포밀화 반응용 촉매 조성물 및 이를 이용하는 알데히드의 제조방법
EP2566841A1 (en) 2010-05-04 2013-03-13 Celanese International Corporation Process for the semi-continuous transvinylation of carboxylic acids with vinyl acetate
DE102012002282A1 (de) 2012-02-06 2013-08-08 Oxea Gmbh Verfahren zur Herstellung von Vinylestern
DE102012014395B3 (de) * 2012-07-13 2013-08-22 Oxea Gmbh Isononylamine ausgehend von 2-Ethylhexanol, Verfahren zu ihrer Herstellung sowie ihre Verwendung
DE102012013968A1 (de) * 2012-07-13 2014-04-03 Oxea Gmbh Carbonsäureester der Isononansäure ausgehend von 2-Ethylhexanol, Verfahren zu ihrer Herstellung sowie ihre Verwendung
DE102012013969B4 (de) * 2012-07-13 2017-09-14 Oxea Gmbh Verfahren zur Herstellung eines Gemisches stellungsisomerer aliphatischer Isononansäuren ausgehend von 2-Ethylhexanol

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Publication number Publication date
US20150166456A1 (en) 2015-06-18
DE102012014396B4 (de) 2018-01-11
TW201406718A (zh) 2014-02-16
PL2872478T3 (pl) 2017-05-31
DE102012014396A1 (de) 2014-01-16
JP2015527990A (ja) 2015-09-24
JP6153271B2 (ja) 2017-06-28
US9334225B2 (en) 2016-05-10
KR20150030239A (ko) 2015-03-19
CN104411675B (zh) 2016-10-12
TWI452034B (zh) 2014-09-11
EP2872478A1 (de) 2015-05-20
WO2014008977A1 (de) 2014-01-16
CN104411675A (zh) 2015-03-11
EP2872478B1 (de) 2016-12-07

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