CATALISIS.

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Transcripción de la presentación:

CATALISIS

COMPARACION ENTRE CATALISIS HOMOGENEA Y HETEROGENEA

IVERMECTINA: reducción con catalizador Rh/PPh3 ESTEROIDE

PROCESOS INDUSTRIALES valores en miles de toneladas

TONs y TOFs ENZIMAS Turn-over 0.5 100 300 80000 600000 25 °C (moleculas de sustrato/sitio activo.s) Lisozima 0.5 Quimiotripsina 100 Hexocinasa 300 Catalasa 80000 Anhidrasa Carbonica 600000 CATALIZADORES HOMOGENEOS 25 °C (calculado) Turn-over (°C) Hidroformilación (HCo) 2.4 x 10-6 0.04 (165) Hidrogenación (RhCl(PR3)3) 25 17 (3) Metátesis (WCl6/EtOH/C2H5AlCl2) 120 Ziegler Natta – Pol. etileno Cp2Ti(CH3)2/Al(CH3)3/H2O 400 200 (12) Dimerización de propeno η3-C3H5NiBr(PR3/C2H5AlCl2) 60000 230 (-55)

METATESIS AB + CD = AD + CB

LA DANZA DE LOS ALQUENOS (o intercambio de parejas)

METATESIS: CATALIZADORES Schrock 1990 Muy reactivo Menos reactivo Estable al aire, y solventes próticos PCy3 = triciclohexilfosfina ángulo de cono: 170° PPH3: ángulo de cono: 145°

METATESIS: APLICACIONES

METATESIS: APLICACIONES

METATESIS: APLICACIONES

METATESIS: APLICACIONES

ROMP The catalysts used for ROMP are the same catalysts used for olefin metathesis. However, one has to be a little more careful when selecting a ROMP catalyst. If the catalyst is too active, it can metathesize the unstrained olefinic bonds in the growing polymer chain (a process called "back-biting"), thereby reducing the molecular weight and increasing the molecular weight distribution (polydispersity). For example, consider the synthesis of polyacetylene by ROMP of cyclooctatetraene shown below. Backbiting occurs when the growing polymer chain can orient to undergo an intramolecular metathesis and generate benzene, a thermodynamic sink. To prevent backbiting in this or other systems you must make sure your catalyst does not react with internal olefins!

ROMP: TERMINACION REACCION CON ALDEHIDOS TRANSFERENCIA DE CADENA

HIDROGENACION DE WILKINSON

HIDROGENACION DE WILKINSON: catiónicos -C7H12

LIGANDOS ASIMETRICOS BINAP

Al hidrolizar la amida (NH2): L-Dopa (mal de Parkinson) ESTEREOSELECTIVIDAD Al hidrolizar la amida (NH2): L-Dopa (mal de Parkinson)

Rh / CHIRAFOS

POLIMERIZACION DE ALQUENOS ZIEGLER-NATTA

POLIMERIZACION DE ALQUENOS – ZIRCONOCENOS/MAO

POLIMERIZACION DE ALQUENOS

TACTICIDAD

Coordinación re versus si

Coordinación re versus si

Science, 1995, 267, 217

HIDROFORMILACION REACCIONES COMPETITIVAS

HIDROFORMILACION: COBALTO 18 e- SUSTITUCION DE LIGANDO (MECANISMO DISOCIATIVO) AdOx-ElRed INSERCION 1,2 INSERCION 1,1 Anti-Markovnikov Markovnikov

HIDROFORMILACION: RODIO

HIDROFORMILACION

CARBONILACION DE METANOL (MONSANTO)

ACOPLAMIENTO DE HECK

REGIOSELECTIVIDAD

ESTEREOSELECTIVIDAD INDUCCION ASIMETRICA E

ACOPLAMIENTO DE SONOGASHIRA

ACOPLAMIENTO DE SONOGASHIRA

COMPLEJOS DE NITROGENO ACOPLAMIENTO DE SONOGASHIRA Ligandos y complejos FOSFINAS COMPLEJOS DE NITROGENO

CARBOCICLOS y HETEROCICLOS ACOPLAMIENTO DE SONOGASHIRA Aplicaciones sintéticas ALQUINILACIÓN DE HETEROCICLOS Y ARENOS SÍNTESIS DE ENINAS CARBOCICLOS y HETEROCICLOS

MATERIALES ELECTRÓNICOS Y ELECTRO-ÓPTICOS ACOPLAMIENTO DE SONOGASHIRA Aplicaciones sintéticas SÍNTESIS DE PRODUCTOS NATURALES SÍNTESIS DE MATERIALES ELECTRÓNICOS Y ELECTRO-ÓPTICOS