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Diseño Y Síntesis De Líquidos Iónicos Para Aplicaciones Específicas

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Diseño Y Síntesis De Líquidos Iónicos Para Aplicaciones Específicas Facultade de Química Departamento de Química Orgánica Diseño y síntesis de Líquidos Iónicos para aplicaciones específicas Se opta al título de DOCTOR INTERNACIONAL Memoria presentada por Pedro Verdía Barbará por la que se opta al Grado de Doctor por la Universidade de Vigo Agradecimientos: A mi directora, la profesora Emilia Tojo Suárez, por haberme dado la oportunidad de trabajar en su grupo de investigación y por todo el apoyo que me ha dado durante estos años. Al resto de profesores del grupo de investigación QO-2, Yag, Gelu, Men, Marta, Pedro, a todos los compañeros que han pasado por el laboratorio, especialmente a Miguel Vilas, compañero de fatigas, a Manolo, Zoila, Andrea, Tamara, Massene, etc… y a Candi, técnica de laboratorio del departamento de Química Orgánica. A las personas del grupo PROSEPAV del departamento de ingeniería química de la Universidad de Vigo, sobre todo a Emilio y Ana Belen, por su colaboración en la realización de este trabajo. Al centro tecnológico Tekniker por su colaboración en la realización de este trabajo. A la vicerrectoría de investigación de la Universidade de Vigo por la concesión de una beca pre-doctoral. Al ministerio de educación, cultura y deporte del gobierno de España por la concesión de una beca de movilidad. Al profesor Tom Welton del Imperial College London, por haberme dado la oportunidad de realizar una estancia en su grupo de investigación, y a toda la gente de su grupo, especialmente a Agnieszka Brandt y Trang Quynh To, que me guiaron y dieron toda su ayuda. A mi familia y amigos. Y para acabar por el principio, a Hilda y Borja, quienes me empujaron a empezar esto. “Felix qui potuit rerum cognoscere causas” ("feliz quien pudo conocer las causas de las cosas") Virgilio Abreviaturas: % - tanto por ciento ºC – grados centígrados β - coeficiente de distribución de soluto ∆β - error medio del coeficiente de distribución de soluto δ – desplazamiento químico (en ppm) η – viscosidad ν – frecuencia σx - desviación media cuadrática de la composición 1-BrBu – 1-bromobutano Å –ångström(s) AcOEt – acetato de etilo AcOH – ácido acético atm. – atmósfera(s) bibl. – bibliografía Bn – bencil(o) c – cuartete Calcd. – calculado c.c.f. – cromatografía de capa fina CDCl 3 – cloroformo deuterado CH 2Cl 2 – diclorometano cm – centímetro Cp – capacidad calorífica CPK – Corey-Pauling Koltun Disolv. – disolvente DMF – dimetilformamida DMSO – dimetilsulfóxido DSC - calorimetría diferencial de escaneado (Differential Scanning Calorimetry) d – doblete dd – doble doblete ELL – equilibrio líquido-líquido EEUU – estados unidos eq. – equivalente(s) et al . – y otros FAB – bombardeo por átomos rápidos (fast atom bombardment) g – gramo h – hora(s) HDS – hidrodesulfuración Hex – hexano HR-MS – espectrometria de masas de alta resolución ∆HVap - entalpía de vaporización Hz – hertzios IR – infrarrojo J – constante de acoplamiento J – julios K – grados Kelvin kJ – kilo Julios l – longitud LI(s) – líquido(s) iónico(s) m – multiplete m/z – relación masa - carga MeI – iodometano MeOD – metanol deuterado MeOH – metanol MHz – mega hertzios min. – minutos mL – mililitro(s) mmol – milimole(s) mPa·s – milipascales por segundo MS – espectrometria de masas n-BuLi - n-butillitio nm – nanómetros NRTL – modelo de dos líquidos no aleatorio (Non-Random Two Liquid model) o- - orto- OOT – temperatura de descomposición oxidativa (Oxidation Onset Temperature) p- – para- p.f. – punto de fusión Pa – pascal(es) PDSC - calorimetría de escaneado diferencial Ph – fenil(o) pH – potencial de hidrógeno ppm – partes por millón PTFE – politetrafluoroetileno (teflón) pv - presión de vapor ref. – referencia Rend. – rendimiento RMN – resonancia magnética nuclear s – segundo(s) s - singlete S – selectividad t – tiempo t- triplete t.a. – temperatura ambiente Tª – temperatura Tdecomp - temperatura de descomposición Tfus - punto de fusión Tg - temperatura de transición vítrea TGA – análisis termogravimétrico (ThermoGravimetric Analysis) THF – tetrahidrofurano Tol. – tolueno TS – tiofeno U-HDS – ultra hidrodesulfuración UV (u.v.) – ultravioleta x – fracción molar Abbreviations: % R ave. sugar - average recovery of a specific component % T 45 - percent total solids of a sample oven dried at 45ºC. ε – Absorptivity µl – microlitre(s) A - area AFEX - ammonia fiber expansion AIL – acid insoluble lignin AIR – acid insoluble residue ASL – acid soluble lignin C - concentration Fc - fraction of sugar in untreated biomass as determined by compositional analysis. FHPLC (S) - calibration factor for substance S FT - molecular mass transformation factor GHs - glycosyl hydrolases HMF – hydroxymethyl furfural HPLC – high performance liquid chromatography IL(s) – ionic liquid(s) l - lenght LAP – laboratory analytical procedure LSIMS – liquid secondary ion mass spectrometry M (m) – mass mg – milligram ml – mililitre(s) mm – millimetre mM – millimolar ODW - oven dried weight PRG - perennial rhizomatous grasses rpm – revolutions per minute UK – United kingdom USA (U. S.) – United States of America V – volume vol – volume VPL - total volume of pretreatment liquor wt – weight Relación de compuestos: 1.- 1-metilimidazol ( N-metilimidazol) 2.- 1,3-propanosultona 3.- 3-(1-metilimidazolio-3-il)propano-1-sulfonato 4.- imidazol 5.- tartrato de tetrabutilfosfonio, [(C 4)4P][(R,R)-Trtr] 6.- bis(trifluorometanosulfonil)amiduro de tetrabutilfosfonio, [[(C 4)4P][NTf 2] 7.- metilsulfato de 1,3.dimetilimidazolio, [C 1C1Im][C 1SO 4] 8.- etilsulfato de 1-etil-3-metilimidazolio, [C 2C1Im][C 2SO 4] 9.- metilsulfato de 1-butil-3-metilimidazolio, [C 4C1Im][C 1SO 4] 10.- etilsulfato de 1-butil-3-etilimidazolio, [C 4C2Im][C 2SO 4] 11.- metilsulfato de 1-bencil-3-metilimidazolio, [(C 6H5)C 1C1Im][C 1SO 4] 12.- etilsulfato de 1-bencil-3-etilimidazolio, [(C 6H5)C1C2Im][C 2SO 4] 13.- benzaldehído 14.- malononitrilo 15.- 2-(fenilmetilen)malononitrilo 16.- 4-clorobenzaldehído 17.- 4-dimetilaminobenzaldehido 18.- 4-metoxibanzaldehido 19.- 4-metilbenzaldehído 20.- 2-nitrobenzaldehido 21.- cianoacetato de metilo 22.- fenilmetilencianoacetato de metilo 23.- 2-[( p-clorofenil)metilen]malononitrilo 24.- 2-[( p-dimetilaminofenil)metilen]malononitrilo 25.- 2-[( p-metoxifenil)metilen]malononitrilo 26.- 2-[( p-metilfenil)metilen]malononitrilo 27.- 2-[( o-nitrofenil)metilen]malononitrilo 28.- 2,3,5-colidina 29.- 2-etil-3,5-dimetilpiridina 30.- 3,5-dimetil-2-pentilpiridina 31.- 1-butilimidazol 32.- hidrógenosulfato de 1-butilimidazolio, [C 1HIm][HSO 4] 33.- hexafluorofosfato de 1-hexil-3-metilimidazolio, [C6C1Im][PF 6] 34.- glicina 35.- ácido de Meldrum 36.- ácido barbitúrico 37.- ácido tiobarbitúrico 38.- tetrafluoroborato de 1-butil-3-metilimidazolio 39.- 3-metil-1-fenilpirazolin-5-(4 H)-ona 40.- nitrato de etilamonio, [C 2NH 3][NO 3] 41.- dimetilsulfato 42.- dietilsulfato 43.- N-bencilimidazol 44.- salicilaldehido 45.- malonato de dimetilo 46.- 3-metoxicarbonilcumarina 47.- L-prolina 48.- metil acetoacetato 49.- etil benzoilacetato 50.- malonato de dietilo 51.- acetato de etilmetilsulfonilo 52.- acetato de metilfenilsulfonilo 53.- 3-acetilcumarina 54.- 3-cianocumarina 55.- 3-benzocarbonilcumarina 56.- 3-etoxicarbonilcumarina 57.- 3-metilsulfonilcumarina 58.- 3-fenilsulfonilcumarina 59.- 2-hidroxi-5-metilbenzaldehido 60.- 2-hidroxi-3-metilbenzaldehido 61.- 2-hidroxi-5-metoxibenzaldehido 62.- 2-hidroxi-4-metoxibenzaldehido 63.- 2-hidroxi-3-metoxibenzaldehido 64.- 5-bromo-2-hidroxi-3-metoxibenzaldehido 65.- 2-hidroxi-1-naphtaldehído 66.- 2,4-dihidroxibenzaldehído 67.- 4-bromo-2-hidroxibenzaldehído 68.- 6-metil-3-etoxicarbonilcumarina 69.- 6-metil-3-metoxicarbonilcumarina 70.- 8-metil-3-metoxicarbonilcumarina 71.- 6-metil-3-metoxicarbonil-cumarina 72.- 6-metil-3-metoxicarbonilcumarina 73.- 8-metoxi-3-metoxicarbonilcumarina 74.- 6-bromo-8-metoxi-3-metoxicarbonilcumarina 75.- 5,6-benzo-3-metoxicarbonilcumarina 76.- 7-hidroxi-3-metoxicarbonilcumarina 77.- 7-bromo-3-metilsulfonilcumarina 78.- tiofeno 79.- benzotiofeno 80.- dibenzotiofeno 81.- benozo[b]nafto-[2,3-d]tiofeno 82.- 4-metildibenzotiofeno 83.- 4,6-dimetildibenzotiofeno 84.- 2,8-dimetildibenzotiofeno 85.- 3,7-dimetildibenzotiofeno 86.- tetrafluroborato de 1-octilpiridinio, [C 8Py][BF 4] 87.- tetrafluroborato de 1-hexilpiridinio, [C 6Py][BF 4] 88.- tetrafluroborato de 1-butilpiridinio, [C 4Py][BF 4] 89.- tetralina 90.- bis(trifluorometanosulfonil)amiduro de 1-hexil-3,5-dimetilpiridinio, 1 3 5 [C 6 C1 C1 Py][NTf 2] 91.- sal de litio de bis(trifluorometanosulfonil)amiduro, LiNTf 2 92.- 2,3,5-colidina 93.- 2-etil-3,5-dimetilpiridina 94.- 2,4-dimetilpiridina 95.- 3,5-dimetil-2-pentilpiridina 1 2 3 5 96.- bromuro de 1-hexil-2,3,5-trimetilpiridinio, [C 6 C1 C1 C1 Py][Br] 1 2 3 5 97.- ioduro de 1-hexil-2,3,5-trimetilpiridinio, [C 6 C1 C1 C1 Py][I] 2 1 3 5 98.- ioduro de 2-etil-1-hexil-3,5-dimetilpiridinio, [C 2 C6 C1 C1 Py][I] 2 1 3 5 99.- bromuro de 2-etil-1-hexil-3,5-dimetilpiridinio, [C2 C6 C1 C1 Py][Br] 1 3 5 2 100.- bromuro de 1-etil-3,5-dimetil-2-pentilpiridinio, [C 2 C1 C1 C5 Py][Br] 1 3 5 2 101.- bromuro de 1-butil-3,5-dimetil-2-pentilpiridinio, [C 4 C1 C1 C5 Py][Br] 1 3 5 2 102.- bromuro de 1-hexil-3,5-dimetil-2-pentilpiridinio, [C 6 C1 C1 C5 Py][Br] 103.- bis(trifluorometanosulfonil)amiduro de 1-hexil-2,3,5-trimetilpiridinio, 1 2 3 5 [C 6 C1 C1 C1 Py][NTf 2] 104.- bis(trifluorometanosulfonil)amiduro de 2-etil-1-hexil-3,5-dimetilpiridinio, 2 1 3 5 [C 2 C6 C1 C1 Py][NTf 2] 105.- bis(trifluorometanosulfonil)amiduro de 1-etil-3,5-dimetil-2-pentilpiridinio, 1 3 5 2 [C 2 C1 C1 C5 Py][NTf 2] 106.- bis(trifluorometanosulfonil)amiduro de 1-butil-3,5-dimetil-2-
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