ES2953133T3 - Ester trimetílico del ácido 3,3',3''-(ciclohexano-1,2,4-triil)tripropiónico - Google Patents

Ester trimetílico del ácido 3,3',3''-(ciclohexano-1,2,4-triil)tripropiónico Download PDF

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ES2953133T3
ES2953133T3 ES20193080T ES20193080T ES2953133T3 ES 2953133 T3 ES2953133 T3 ES 2953133T3 ES 20193080 T ES20193080 T ES 20193080T ES 20193080 T ES20193080 T ES 20193080T ES 2953133 T3 ES2953133 T3 ES 2953133T3
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triyl
cyclohexane
trimethyl ester
acid trimethyl
tripropionic acid
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Kaiwu Dong
Robert Franke
Ralf Jackstell
Matthias Beller
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Evonik Operations GmbH
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Abstract

Éster trimetílico del ácido 3,3',3"(ciclohexano-1,2,4-triil)tripropiónico. (Traducción automática con Google Translate, sin valor legal)

Description

DESCRIPCIÓN
Éster trimetílico del ácido 3,3',3''-(ciclohexano-1,2,4-triil)tripropiónico
La presente invención se refiere al éster trimetílico del ácido 3,3',3''-(ciclohexano-1,2,4-triil)tripropiónico.
La alcoxicarbonilación de compuestos etilénicamente insaturados es un proceso de creciente importancia. Por alcoxicarbonilación se entiende la reacción de compuestos etilénicamente insaturados, tales como olefinas, con monóxido de carbono y alcoholes en presencia de un metal o, respectivamente, un complejo metálico y un ligando para formar los ésteres correspondientes:
Figure imgf000002_0003
Mediante un procedimiento de este tipo se pueden convertir los tres grupos vinilo del trivinilciclohexano en ésteres. El documento EP0495 175 A2 describe la hidrocarboxialquilación de 1,2,4-trivinilciclohexano con alcoholes C1-C10 en presencia de un catalizador de cobalto, obteniéndose mezclas de los ésteres correspondientes, que se utilizan como monómeros y comonómeros.
El objeto de la presente invención es proporcionar un plastificante de gelificación rápida para plásticos, en particular para PVC, que permita una baja temperatura de procesamiento.
Este objeto se logra mediante un compuesto según la fórmula (1):
Figure imgf000002_0001
Preferentemente, el compuesto se produce según el procedimiento descrito en el presente documento.
Figure imgf000002_0002
Figure imgf000003_0001
Se dispusieron [Pd(acac)2] (15,2 mg, 0,1% en moles), L (103 mg, 0,4% en moles) y ácido p-toluenosulfónico (PTSA) (143 mg, 1,5% en moles) en atmósfera de argón en un autoclave de acero de 100 ml. Después se inyectaron MeOH (30 ml) y trivinilciclohexano (i) (8,1 g, 50 mmol) mediante una jeringa. El autoclave se purgó tres veces con CO y después se aplicó una presión de CO de 40 bares. La reacción se realizó a 110 °C durante 10 h. A continuación, el autoclave se enfrió a temperatura ambiente y se despresurizó. El producto deseado se purificó por destilación (165 °C a 10-3 bares) y se caracterizó mediante RmN de 1H, RMN de 13C y HR-MS (15,6 g, 91% de rendimiento).
RMN de 1H (300 MHz, C6D6) 5 = 3,39-3,37 (m, 9H), 2,24-1,86 (m, 7H), 1,48-0,27 (m, 14H). RMN de 13C (75 MHz, C6D6) 5 = 173,68-173,54 (m), 51,04, 40,60-40,47 (m), 38,24, 38,14, 37,51,37,07, 36,54, 36,10, 35,52, 35,14, 33,87, 32,70, 32,55, 32,51,32,38, 32,29, 32,23, 32,08, 31,97, 31,86, 31,76, 31,68, 31,63, 31,43, 30,98, 30,79, 30,75, 29,31, 28,52, 28,47, 28,34, 28,13, 28,11,27,13, 26,58, 25,12, 20,79, 19,74.
EM (EI): 311 (13,40), 293 (3,65), 269 (75,76), 237 (60,40), 219 (25,13), 205 (100), 191 (17,62), 177 (14,83), 145 (24,59). HR-MS (ESI): calculado C18H30O6 [M H]+ : 343,21152, hallado: 343,21113.
Síntesis de 3,3',3"-(ciclohexano-1,2,4-triil)tris(propan-1-ol) (2) ("triol") (no según la invención)
Figure imgf000003_0002
Se dispusieron Ru-MACHO-BH (59 mg, 2% en moles) y NaOMe (27 mg, 10% en moles) en atmósfera de argón en un autoclave de acero de 25 ml. Después se inyectaron MeOH (8 ml) y el triéster (1) (1,93 g, 5,67 mmol) mediante una jeringa. El autoclave se purgó tres veces con H2 y después se aplicó una presión de H2 de 50 bares. La reacción se realizó a 100 °C a lo largo de 10 h. A continuación, el autoclave se enfrió a temperatura ambiente y se despresurizó. El producto deseado se purificó por filtración a través de gel de sílice y se caracterizó mediante RMN de 1H, RMN de 13C y HR-MS (1,4 g, 96% de rendimiento). RMN de 1H (400 MHz, CD3OD) 5 = 3,32-3,30 (m, 6H), 1,85-1,77 (m, 2H), 1,63-0,62 (m, 19H). RMN de 13C (100 MHz, CD3OD) 5 = 63,53-63,29 (m), 42,69, 42,53, 42,39, 42,31, 40,34, 40,24, 39,28, 38,89, 38,12, 38,02, 37,58, 37,27, 35,89, 34,78, 34,72, 34,53, 34,37, 33,17, 31,52, 31,50, 31,40, 31,38, 31,05, 30,60, 30,48, 30,41,30,32, 30,24, 30,17, 28,77, 28,22, 26,61,22,53, 21,45. EM (EI): 222 (1,06), 194 (1,14), 181 (2,96), 163 (11,54), 135 (9,81), 121 (17,04), 107 (15,25), 93 (32,69).
HR-MS (ESI): calculado C15H30O3 [M H]+ : 259,22677, hallado: 259,2269.
Producción de plastisoles
Se produjeron plastisoles de PVC, tales como los que se utilizan, por ejemplo, para producir películas de cubrición para revestimientos de suelos. Los datos en la formulación de plastisol se indican en partes en masa. La formulación de la composición polimérica se presenta en la tabla 1.
Tabla 1 Formulación de plastisol
Figure imgf000004_0001
En primer lugar se pesan los componentes líquidos y después los componentes en polvo en un vaso de PE. La mezcla se remueve a mano con una espátula para pomadas de forma que no quede polvo sin humedecer. A continuación, el vaso de mezcla se sujeta en el dispositivo de sujeción de un agitador de disolvente. Después de conectar el agitador, la velocidad se aumenta lentamente a aproximadamente 2000 rpm. Mientras tanto, el plastisol se desairea cuidadosamente, la presión no debe superar 20 mbar.
Tan pronto como el plastisol haya alcanzado una temperatura de aproximadamente 30 °C, la velocidad se reduce a aproximadamente 350 rpm. A partir de ahora, el plastisol se desairea durante 9 minutos a esta velocidad y a una presión inferior a 20 mbar. Esto aseguró que la homogeneización del plastisol se lograra con un aporte de energía definido. A continuación, el plastisol se calienta inmediatamente a 25,0 °C en una cabina climática para investigaciones adicionales.
Comportamiento de gelificación de los plastisoles
La investigación del comportamiento de gelificación de las pastas se llevó a cabo con un aparato Physica MCR 101 en modo de oscilación con un sistema de medición placa-placa (PP25), que se operó bajo control de esfuerzo cortante. Se conectó una campana de control de temperatura adicional al aparato para lograr una distribución homogénea del calor y una temperatura uniforme de la muestra.
Se establecieron los parámetros siguientes:
Figure imgf000004_0002
Realización de la medición
Se aplican algunos gramos de la pasta que hay que medir con la espátula en la placa inferior del sistema de medición sin burbujas de aire. A este respecto, se debe tener en cuenta que después de que el sistema de medición se haya ensamblado, un poco de pasta puede derramarse uniformemente desde el sistema de medición (no más de 6 mm en cualquier dirección). Después se coloca la campana de control de temperatura sobre la muestra y se inicia la medición. La viscosidad compleja de la pasta se determina después de 24 horas (almacenamiento de la pasta a 25 °C en una cabina de control de la temperatura Memmert) en función de la temperatura.
Un aumento significativo en la viscosidad del complejo se toma como medida de gelificación. Por lo tanto, se utiliza como valor comparativo la temperatura a la que se alcanza una viscosidad de la pasta de 1000 Pas.
El ensayo se repitió con tres plastisoles comparativos, cada uno de los cuales usaba un plastificante diferente.
Tabla 2: Gelificación de los plastisoles después de 24 horas, temperatura en °C a la que se alcanza una viscosidad de la pasta de 103 Pa s
Figure imgf000005_0001
El valor deseado de 1000 Pa*s ya se pudo alcanzar a 65 °C con el compuesto (1) según la invención. Estas bajas temperaturas de gelificación representan una ventaja para el proceso de fabricación. Permiten el procesamiento del plastisol a temperaturas más bajas.

Claims (1)

REIVINDICACIONES
1. Compuesto según la fórmula (1):
Figure imgf000006_0001
ES20193080T 2019-12-17 2019-12-17 Ester trimetílico del ácido 3,3',3''-(ciclohexano-1,2,4-triil)tripropiónico Active ES2953133T3 (es)

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EP19216884.7A EP3838886B1 (de) 2019-12-17 2019-12-17 Alkoxycarbonylierung von trivinylcyclohexan
EP20193080.7A EP3842411B1 (de) 2019-12-17 2019-12-17 3,3',3''-(cyclohexan-1,2,4-triyl)tripropionsäuretrimethylester

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EP4703346A1 (de) 2024-09-03 2026-03-04 Evonik Oxeno GmbH & Co. KG Weichmacherzusammensetzung enthaltend trimethylester der 1,2,4-cyclohexantripropionsäure und 1,2-dialkylcyclohexandicarbonsäureester
EP4703348A1 (de) 2024-09-03 2026-03-04 Evonik Oxeno GmbH & Co. KG Mischester der 1,2,4-cyclohexantripropionsäure und eine weichmacherzusammensetzung enthaltend die mischester
EP4703418A1 (de) 2024-09-03 2026-03-04 Evonik Oxeno GmbH & Co. KG Weichmacherzusammensetzung enthaltend trimethylester der 1,2,4-cyclohexantripropionsäure und dialkylphthalsäureester
EP4703419A1 (de) 2024-09-03 2026-03-04 Evonik Oxeno GmbH & Co. KG Weichmacherzusammensetzung enthaltend trimethylester der 1,2,4-cyclohexantripropionsäure und ein trialkyltrimellitat
EP4703421A1 (de) 2024-09-03 2026-03-04 Evonik Oxeno GmbH & Co. KG Weichmacherzusammensetzung enthaltend trimethylester der 1,2,4-cyclohexantripropionsäure und einen dialkylterephthalsäureester
EP4703422A1 (de) 2024-09-03 2026-03-04 Evonik Oxeno GmbH & Co. KG Weichmacherzusammensetzung enthaltend trimethylester der 1,2,4-cyclohexantripropionsäure und einen 1,4-dialkylcyclohexandicarbonsäureester
EP4703423A1 (de) 2024-09-03 2026-03-04 Evonik Oxeno GmbH & Co. KG Weichmacherzusammensetzung enthaltend trimethylester der 1,2,4-cyclohexantripropionsäure und deren längerkettige derivate
EP4703420A1 (de) * 2024-09-03 2026-03-04 Evonik Oxeno GmbH & Co. KG Weichmacherzusammensetzung enthaltend c4- bis c9-alkylester der 1,2,4-cyclohexantripropionsäure und dibutylterephthalat oder dipentylterephthalat

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