ES2527746T3 - Método de extracción con disolventes usando trifluoro, monocloropropeno - Google Patents

Método de extracción con disolventes usando trifluoro, monocloropropeno Download PDF

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Publication number
ES2527746T3
ES2527746T3 ES06785612.0T ES06785612T ES2527746T3 ES 2527746 T3 ES2527746 T3 ES 2527746T3 ES 06785612 T ES06785612 T ES 06785612T ES 2527746 T3 ES2527746 T3 ES 2527746T3
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Prior art keywords
compositions
compounds
trifluoro
solvent extraction
present
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Rajiv R. Singh
Hang T. Pham
David P. Wilson
Raymond H. Thomas
Mark W. Spatz
David A. Metcalf
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Honeywell International Inc
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Honeywell International Inc
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Abstract

Un método de extracción con disolventes que comprende extraer con disolventes un sabor o fragancia poniendo en contacto dicho sabor o fragancia con HFCO-1233 (trifluoro, monocloropropeno).

Description

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DESCRIPCIÓN
Método de extracción con disolventes usando trifluoro, monocloropropeno
CAMPO DE LA INVENCIÓN
Esta invención se refiere a métodos de extracción con disolventes. La presente invención se refiere a métodos de extracción con disolventes que comprenden al menos un trifluoro, monocloropropeno.
ANTECEDENTES
Los fluidos a base de fluorocarbonos han encontrado un uso generalizado en muchas aplicaciones comerciales e industriales, incluyendo como fluido de trabajo en sistemas tales como aire acondicionado, bomba de calor y sistemas de refrigeración, como propelentes de aerosoles, como agentes de soplado, como medios de transferencia de calor, y como dieléctricos gaseosos. Debido a ciertos problemas medioambientales sospechosos, incluyendo los potenciales de calentamiento global relativamente elevados, asociados con el uso de algunas de las composiciones que se han usado hasta ahora en estas aplicaciones, se ha hecho cada vez más deseable usar fluidos que tengan un potencial de agotamiento del ozono bajo o incluso nulo, tales como hidrofluorocarbonos (“HFCs”). De este modo, es deseable el uso de fluidos que no contengan clorofluorocarbonos (“CFCs”) o hidroclorofluorocarbonos (“HCFCs”). Además, algunos fluidos de HFC pueden tener potenciales de calentamiento global relativamente elevados asociados con ellos, y es deseable usar fluidos hidrofluorocarbono u otros fluidos fluorados que tengan potenciales de calentamiento global tan bajos como sea posible a la vez que mantengan el comportamiento deseado en propiedades de uso. Adicionalmente, el uso de fluidos de un solo componente o mezclas semejantes a azeotropos, que no se fraccionen sustancialmente al hervirlos y en la evaporación, es deseable en ciertas circunstancias.
Ciertos fluorocarbonos han sido un componente preferido en muchos fluidos de intercambio de calor, tales como refrigerantes, durante muchos años en muchas aplicaciones. Por ejemplo, los fluoroalcanos, tales como derivados de clorofluorometano y de clorofluoroetano han ganado uso generalizado como refrigerantes en aplicaciones que incluyen acondicionamiento del aire y aplicaciones en bombas de calor, dada su combinación única de propiedades químicas y físicas. Muchos de los refrigerantes utilizados habitualmente en sistemas de compresión de vapor son fluidos de un solo componente o mezclas azeotrópicas.
Como se sugiere anteriormente, ha aumentado la preocupación en años recientes sobre el daño potencial a la atmósfera y clima de la Tierra, y a este respecto se han identificado como particularmente problemáticos ciertos compuestos a base de cloro. El uso de composiciones que contienen cloro (tales como clorofluorocarbonos (CFC’s), hidroclorofluorocarbonos (HCF’s) y similares) como el fluido de trabajo en sistemas de transferencia de calor, tales como en sistemas de refrigeración y de acondicionamiento de aire, se ha visto desfavorecido debido a las propiedades de agotamiento del ozono asociadas con muchos de tales compuestos. De este modo, ha habido una necesidad creciente de nuevos compuestos y composiciones de fluorocarbonos e hidrofluorocarbonos que sean alternativas atractivas para las composiciones usadas hasta ahora en estas y en otras aplicaciones. Por ejemplo, se ha hecho deseable modernizar sistemas de refrigeración que contienen cloro sustituyendo refrigerantes que contienen cloro por compuestos refrigerantes que no contienen cloro que no agotarán la capa de ozono, tales como hidrofluorocarbonos (HCF’s). La industria en general, y la industria de transferencia de calor en particular, están continuamente buscando nuevas mezclas a base de fluorocarbonos que ofrezcan alternativas a, y sean consideradas sustitutos medioambientalmente más seguros para, CFCs y HCFCs. Sin embargo, se considera generalmente importante, al menos con respecto a fluidos de transferencia de calor, que cualquier sustituto potencial deba poseer también aquellas propiedades presentes en muchos de los fluidos más ampliamente usados, tales como propiedades de transferencia de calor excelentes, estabilidad química, baja o ninguna toxicidad, inflamabilidad nula y/o compatibilidad con lubricantes, entre otras.
Se ha observado que la compatibilidad con el lubricante es de particular importancia en muchas de las aplicaciones. Más particularmente, es altamente deseable que los fluidos de refrigeración sean compatibles con el lubricante utilizado en la unidad compresora, usado en la mayoría de los sistemas de refrigeración. Desafortunadamente, muchos fluidos de refrigeración que no contienen cloro, incluyendo HFC’s, son relativamente insolubles y/o inmiscibles en los tipos de lubricantes usados tradicionalmente con CFC’s y HFC’s, incluyendo, por ejemplo, aceites minerales, alquilbencenos o poli(alfa-olefinas). A fin de que una combinación de fluido de refrigeración y lubricante trabaje a un nivel deseable de eficiencia en un sistema de refrigeración por compresión, acondicionamiento de aire y/o bomba de calor, el lubricante debería ser suficientemente soluble en el líquido de refrigeración a lo largo de un amplio intervalo de temperaturas de funcionamiento. Tal solubilidad reduce la viscosidad del lubricante y permite que fluya más fácilmente a través del sistema. En ausencia de tal solubilidad, los lubricantes tienden a atascarse en los serpentines del evaporador del sistema de refrigeración, de acondicionamiento de aire o de bomba de calor, así como en otras partes del sistema, y de este modo reducen la eficiencia del sistema.
Con respecto a la eficiencia en el uso, es importante señalar que una pérdida en el comportamiento termodinámico del refrigerante o en la eficiencia energética puede tener impactos medioambientales secundarios a través de un mayor uso de combustibles fósiles que surge de una mayor demanda de energía eléctrica.
Además, generalmente se considera deseable que los sustitutos de los refrigerantes de CFC sean eficaces sin
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cambios de ingeniería importantes para la tecnología de compresión de vapor convencional usada actualmente con refrigerantes de CFC.
La inflamabilidad es otra propiedad importante para muchas aplicaciones. Esto es, se considera importante o esencial en muchas aplicaciones, incluyendo particularmente en aplicaciones de transferencia de calor, usar composiciones que no sean inflamables. De este modo, frecuentemente es beneficioso usar en tales composiciones compuestos que no sean inflamables. Como se usa aquí, la expresión “no inflamable” se refiere a compuestos o composiciones que se determina que no son inflamables según se determina de acuerdo con el estándar de ASTM E-681, fechado el 2002, que se incorpora aquí como referencia. Desafortunadamente, muchos HFC’s que pueden ser de otro modo deseables para uso en composiciones refrigerantes no son no inflamables. Por ejemplo, el fluoroalcano difluoroetano (HFC-152a) y el fluoroalqueno 1,1,1-trifluropropeno (HFO-1243zf) son cada uno inflamable, y por lo tanto no son viables para uso en muchas aplicaciones.
Los fluoroalquenos superiores, esto es, alquenos sustituidos con flúor que tienen al menos cinco átomos de carbono, se han sugerido para uso como refrigerantes. La patente U.S. nº 4.788.352 – Smutny se refiere a la producción de compuestos de C5 a C8 fluorados que tienen al menos cierto grado de insaturación. La patente de Smutny identifica tales olefinas superiores que se sabe que tienen utilidad como refrigerantes, plaguicidas, fluidos dieléctricos, fluidos de transferencia de calor, disolventes, e intermedios en diversas reacciones químicas. (Véase la columna 1, líneas 11-22).
Aunque las olefinas fluoradas descritas en Smutny pueden tener cierto nivel de eficacia en aplicaciones de transferencia de calor, se cree que tales compuestos también pueden tener ciertas desventajas. Por ejemplo, algunos de estos compuestos pueden tender a atacar sustratos, particularmente plásticos para fines generales tales como resinas acrílicas y resinas ABS. Además, los compuestos olefínicos superiores descritos en Smutny también pueden ser indeseables en ciertas aplicaciones debido al nivel potencial de toxicidad de tales compuestos, que puede surgir como resultado de la actividad plaguicida señalada en Smutny. También, tales compuestos pueden tener un punto de ebullición que es demasiado elevado para hacerlos útiles como un refrigerante en ciertas aplicaciones.
Los derivados de bromofluorometano y bromoclorofluorometano, particularmente bromotrifluorometano (Halon 1301) y bromoclorodifluorometano (Halon 1211), han ganado uso generalizado como agentes de extinción de incendios en áreas cerradas tales como cabinas de aviones y habitaciones de ordenador. Sin embargo, el uso de diversos halones se está eliminando gradualmente debido a su capacidad elevada de agotamiento del ozono. Además, puesto que los halones se usan frecuentemente en áreas en las que están presentes seres humanos, las sustituciones adecuadas deben ser también seguras para los seres humanos a las concentraciones necesarias para suprimir o extinguir el incendio.
El documento US 2004/0256594 describe el uso de tetrafluoropropenos, particularmente HFO-1234, en una variedad de aplicaciones, incluyendo la extracción con disolventes.
De este modo, se aprecia una necesidad de composiciones, y particularmente composiciones de disolventes, que sean útiles en métodos de extracción con disolventes, a la vez que se evitan una o más de las desventajas señaladas anteriormente.
SUMARIO
La presente invención se refiere a un método de extracción con disolventes que comprende extraer con disolventes un sabor o fragancia poniendo en contacto dicho sabor o fragancia con HCFO-1233 (trifluoro, monocloropropeno). El método comprende particularmente extraer jasmona con disolventes.
Los trifluoro, monocloropropenos (HFCO-1233), e incluso más preferiblemente CF3CCl=CH2 (HFO-1233xf) y CF3CH=CHCl (HFO-1233zd)), son especialmente preferidos.
El término “HFO-1233” se usa aquí para referirse a todos los trifluoro, monocloropropenos. Entre los trifluoro, monocloropropenos se incluyen 1,1,1,trifluoro-2,cloro-propeno (HFCO-1233xf), tanto cis-como trans-1,1,1-trifluoro3,cloropropeno (HFCO-1233zd). El término HFCO-1233zd se usa aquí genéricamente para referirse a 1,1,1-trifluoro3,cloro-propeno, independientemente de si está en forma cis o trans. Los términos “cisHFCO-1233zd” y “transHFCO1233zd” se usan aquí para describir las formas cis y trans de 1,1,1-trifluoro,3-cloropropeno, respectivamente. El término “HFCO-1233zd” incluye por lo tanto dentro de su alcance cisHFCO-1233zd, transHFCO-1233zd, y todas las combinaciones y mezclas de estos.
La presente invención proporciona métodos de extracción con disolventes que utilizan las composiciones de la presente invención, que comprenden la extracción de un sabor y fragancia.
DESCRIPCIÓN DETALLADA DE REALIZACIONES PREFERIDAS
LAS COMPOSICIONES
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Las realizaciones preferidas de la presente invención se refieren a métodos de extracción con disolventes usando composiciones que comprenden al menos un trifluoro, monocloropropeno.
Se cree que, en general, los compuestos de trifluoro, monocloropropeno encuentran uso como fragancias, formulaciones de sabor y composiciones disolventes. Sin embargo, se ha encontrado sorprendente e inesperadamente que algunos de los compuestos descritos anteriormente muestran un nivel bajo muy deseable de toxicidad en comparación con otros de tales compuestos. Como se puede apreciar fácilmente, este descubrimiento es de ventaja y beneficio potencialmente enorme para la formulación de no sólo composiciones refrigerantes, sino también cualesquiera y todas las composiciones que de otro modo contuviesen compuestos relativamente tóxicos que satisfagan las fórmulas descritas anteriormente.
Se cree que las presentes composiciones poseen propiedades que son ventajosas por un número de razones importantes. Por ejemplo, se cree, basándose al menos en parte en modelos matemáticos, que las fluoroolefinas de la presente invención no tendrán un efecto sustancialmente negativo sobre la química de la atmósfera, siendo contribuyentes despreciables al agotamiento del ozono en comparación con otras especies halogenadas. Las composiciones preferidas de la presente invención tienen así la ventaja de no contribuir sustancialmente al agotamiento del ozono. Las composiciones preferidas tampoco contribuyen sustancialmente al calentamiento global en comparación con muchos de los hidrofluoroalcanos actualmente en uso.
Por supuesto, otros compuestos y/o componentes que modulan una propiedad particular de las composiciones (tal como por ejemplo el coste) también se pueden incluir en las presentes composiciones, y la presencia de todos los citados compuestos y componentes está dentro del alcance amplio de la invención.
En ciertas formas preferidas, las composiciones de la presente invención tienen un Potencial de Calentamiento Global (GWP) no mayor que alrededor de 1000, más preferiblemente no mayor que alrededor de 500, incluso más preferiblemente no mayor que alrededor de 150. En ciertas realizaciones, el GWP de las presentes composiciones no es mayor que alrededor de 100, e incluso más preferiblemente no mayor que alrededor de 75. Como se usa aquí, “GWP” se mide con respecto al del dióxido de carbono y a lo largo de un horizonte de tiempo de 100 años, como se define en “The Scientific Assessment of Ozone Depletion, 2002, a report of the World Meteorological Association’s Global Ozone Research and Monitoring Project”, que se incorpora aquí como referencia.
En ciertas formas preferidas, las presentes composiciones también tienen preferiblemente un Potencial de Agotamiento del Ozono (ODP) no mayor que 0,05, más preferiblemente no mayor que 0,02, e incluso más preferiblemente alrededor de cero. Como se usa aquí, “ODP” es como se define en “The Scientific Assessment of Ozone Depletion, 2002, a report of the World Meteorological Association’s Global Ozone Research and Monitoring Project”, que se incorpora aquí como referencia.
La cantidad de los compuestos contenidos en las presentes composiciones puede variar ampliamente, dependiendo de la aplicación particular, y las composiciones que contienen más de cantidades en trazas y menos de 100% del compuesto están dentro del amplio alcance de la presente invención. Además, las composiciones de la presente invención pueden ser azeotrópicas, semejantes a azeotropos, o no azeotrópicas. En realizaciones preferidas, las presentes composiciones comprenden compuestos de trifluoro, monocloropropeno, en cantidades de alrededor de 5% en peso a alrededor de 99% en peso, e incluso más preferiblemente de alrededor de 5% a alrededor de 95%. En las presentes composiciones se pueden incluir muchos compuestos o componentes adicionales, incluyendo lubricantes, estabilizantes, pasivadores de metales, inhibidores de la corrosión, supresores de la inflamabilidad, y otros compuestos y/o componentes que modulan una propiedad particular de las composiciones (tales como por ejemplo el coste), y la presencia de todos los citados compuestos y componentes está dentro del amplio alcance de la invención. En ciertas realizaciones preferidas, las presentes composiciones incluyen, además del trifluoro, monocloropropeno, uno o más de los siguientes:
Triclorofluorometano (CFC-11)
Diclorodifluorometano (CFC-12)
Difluorometano (HFC-32)
Pentafluoroetano (HFC-125)
1,1,2,2-tetrafluoroetano (HFC-134)
1,1,1,2-Tetrafluoroetano (HFC-134a)
Difluoroetano (HFC-152a)
1,1,1,2,3,3,3-Heptafluoropropano (HFC-227ea)
1,1,1,3,3,3-Hexafluoropropano (HFC-236fa)
1,1,1,3,3-Pentafluoropropano (HFC-245fa)
E06785612
13-01-2015
1,1,1,3,3-Pentafluorobutano (HFC-365mfc)
agua
CO2
La cantidad relativa de cualquiera de los compuestos de la presente invención señalados anteriormente, así como
5 cualesquiera componentes adicionales que se pueden incluir en las presentes composiciones, puede variar ampliamente dentro del alcance amplio general de la presente invención según la aplicación particular para la composición, y todas las citadas cantidades relativas se consideran dentro del alcance de la misma.
En consecuencia, se ha reconocido que las composiciones de la presente invención se pueden usar ventajosamente en gran medida en aplicaciones de fragancia y de sabores, y en aplicaciones de disolventes. Se cree que los
10 expertos en la técnica serán capaces fácilmente de adaptar las presentes composiciones para uso en cualesquiera y todas las aplicaciones sin experimentación innecesaria.
SABORIZANTES Y FRAGANCIAS
Las composiciones de la presente invención también proporcionan ventaja cuando se usan como parte de, y en particular como un vehículo para, formulaciones de sabor y formulaciones de fragancias. La idoneidad de las 15 olefinas fluoradas para este fin se demuestran mediante un procedimiento de ensayo en el que se colocaron 0,39 gramos de jasmona en un tubo de vidrio de paredes gruesas. Se añadieron 1,73 gramos de R-1234ze al tubo de vidrio. El tubo de vidrio se congeló entonces y se cerró herméticamente. Al descongelar el tubo, se encontró que la mezcla tuvo una fase líquida. La disolución contenía 20% en peso de jasmona y 80% en peso de R-1234ze, estableciendo así el uso favorable como vehículo para formulaciones de sabor y fragancias. También establece su
20 potencial como un extrayente de compuestos biológicamente activos (tales como biomasa) y fragancias, incluyendo de materia vegetal. En ciertas realizaciones, se puede preferir usar la presente composición para aplicaciones de extracción con el presente fluido en estado supercrítico.

Claims (5)

  1. E06785612
    13-01-2015
    REIVINDICACIONES
    1.
    Un método de extracción con disolventes que comprende extraer con disolventes un sabor o fragancia poniendo en contacto dicho sabor o fragancia con HFCO-1233 (trifluoro, monocloropropeno).
  2. 2.
    El método de la reivindicación 1, que comprende extraer jasmona con disolventes.
  3. 3.
    El método de la reivindicación 1, en el que el HFCO-1233 es HFCO-1233zd.
  4. 4.
    El método de la reivindicación 1, en el que el HFCO-1233 es cis HFCO-1233zd, trans HFCO-1233zd, o una mezcla de estos.
  5. 5.
    El uso de HFCO-1233 en un método de extracción con disolventes como se define en cualquier reivindicación anterior.
    6
ES06785612.0T 2005-06-24 2006-06-26 Método de extracción con disolventes usando trifluoro, monocloropropeno Active ES2527746T3 (es)

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US69385305P 2005-06-24 2005-06-24
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PCT/US2006/024886 WO2007002625A2 (en) 2005-06-24 2006-06-26 Compositions containing fluorine substituted olefins

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ES10014887T Active ES2746501T3 (es) 2005-06-24 2006-06-26 Composiciones que contienen olefinas sustituidas con flúor
ES10014927.7T Active ES2693291T3 (es) 2005-06-24 2006-06-26 Composiciones que contienen olefinas sustituidas con flúor
ES06785612.0T Active ES2527746T3 (es) 2005-06-24 2006-06-26 Método de extracción con disolventes usando trifluoro, monocloropropeno
ES10014872T Active ES2819051T3 (es) 2005-06-24 2006-06-26 Uso de composiciones que comprenden HFCO-1233zd
ES10014923T Active ES2761950T3 (es) 2005-06-24 2006-06-26 Uso de composiciones que comprenden 1,1,1-trifluoro-3-cloropropeno (HFCO-1233zd) como disolvente
ES10014853T Active ES2700988T3 (es) 2005-06-24 2006-06-26 Composiciones que contienen oleofinas sustituidas por fluor

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ES10014887T Active ES2746501T3 (es) 2005-06-24 2006-06-26 Composiciones que contienen olefinas sustituidas con flúor
ES10014927.7T Active ES2693291T3 (es) 2005-06-24 2006-06-26 Composiciones que contienen olefinas sustituidas con flúor

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ES10014872T Active ES2819051T3 (es) 2005-06-24 2006-06-26 Uso de composiciones que comprenden HFCO-1233zd
ES10014923T Active ES2761950T3 (es) 2005-06-24 2006-06-26 Uso de composiciones que comprenden 1,1,1-trifluoro-3-cloropropeno (HFCO-1233zd) como disolvente
ES10014853T Active ES2700988T3 (es) 2005-06-24 2006-06-26 Composiciones que contienen oleofinas sustituidas por fluor

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