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首页> 外文期刊>Journal of Chemical Technology & Biotechnology >Catalytic conversions in water .5. Carbonylation of 1-(4-isobutylphenyl)ethanol to ibuprofen catalysed by water-soluble palladium-phosphine complexes in a two-phase system
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Catalytic conversions in water .5. Carbonylation of 1-(4-isobutylphenyl)ethanol to ibuprofen catalysed by water-soluble palladium-phosphine complexes in a two-phase system

机译：在水中的催化转化率.5。两相体系中的水溶性钯-膦配合物催化1-（4-异丁基苯基）乙醇羰基化为布洛芬

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摘要

1-(4-Isobutylphenyl)ethanol (IBPE) was carbonylated to 2-(4-isobutylphenyl)propionic acid (ibuprofen) in an aqueous/organic two phase system using the water-soluble Pd(tppts)(3) catalyst [tppts = P(C6H4-m-SO3Na)(3)] in the presence of p-CH3C6H4SO3H at 363 K, 15 MPa CO pressure and a palladium concentration of 150 ppm without addition of organic solvents. Under these conditions the conversion of IBPE was 83% and the selectivity to ibuprofen 82% with no decomposition of the Pd(tppts)(3) catalyst. Both the activity and selectivity were strongly influenced by the tppts/Pd molar ratio and the nature of the added Bronsted acid. Maximum efficiency was observed for P/Pd = 10. Acids of weakly or non-coordinating anions, such as p-CH3C6H4SO3H, CF3COOH or HPF6 afforded carbonylation. No catalytic activity was observed in the presence of acids of strongly coordinating anions, such as HI. The water-soluble Pd/dppps catalyst [dppps = Ar2-nPhnP-(CH2)(3)-PPhnAr2-n; Ar = C6H4-m-SO3Na; n = n = 0: 86% and n = 0, n = 1: 14%] exhibited low catalytic activity and the major product obtained was the linear isomer of ibuprofen, 3-(4-isobutylphenyl) propionic acid (3-IPPA) with selectivities up to 78%. Replacement of tppts by a ligand containing less -SO3Na groups such as monosulphonated triphenylphosphine (tppms) gives rise to a dramatic drop in the catalytic activity and selectivity to ibuprofen. No catalytic activity was observed using palladium catalysts modified with 2-pyridyldiphenylphosphine (PyPPh2) and tris(2-pyridyl) phosphine (PPy3) which are both water soluble in their protonated form. A catalytic cycle is proposed to explain the observed results.
机译：使用水溶性Pd（tppts）（3）催化剂在水/有机两相系统中将1-（4-异丁基苯基）乙醇（IBPE）羰基化为2-（4-异丁基苯基）丙酸（布洛芬） [P（C6H4-m-SO3Na）（3）]在存在p-CH3C6H4SO3H的情况下，在363 K，CO压力为15 MPa和钯浓度为150 ppm的情况下，不添加有机溶剂。在这些条件下，IBPE的转化率为83％，对布洛芬的选择性为82％，而Pd（tppts）（3）催化剂没有分解。 tppts / Pd摩尔比和添加的布朗斯台德酸的性质强烈影响活性和选择性。对于P / Pd = 10，观察到最大效率。弱或非配位阴离子的酸（例如p-CH3C6H4SO3H，CF3COOH或HPF6）提供羰基化作用。在强配位阴离子的酸（例如HI）的存在下未观察到催化活性。水溶性Pd / dppps催化剂[dppps = Ar2-nPhnP-（CH2）（3）-PPhnAr2-n; Ar = C6H4-m-SO3Na; n = n = 0：86％，n = 0，n = 1：14％]表现出较低的催化活性，得到的主要产物是布洛芬，3-（4-异丁基苯基）丙酸（3-IPPA）的线性异构体选择性高达78％。用包含较少-SO3Na基团的配体（例如单磺酸三苯膦（tppms））代替tppts会导致催化活性和对布洛芬的选择性急剧下降。使用2-吡啶基二苯基膦（PyPPh2）和三（2-吡啶基）膦（PPy3）改性的钯催化剂均未观察到催化活性，它们均以质子化形式溶于水。建议使用催化循环来解释观察到的结果。

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