CN1127584C - 有机化合物的电化学还原方法 - Google Patents
有机化合物的电化学还原方法 Download PDFInfo
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- CN1127584C CN1127584C CN97182366.9A CN97182366A CN1127584C CN 1127584 C CN1127584 C CN 1127584C CN 97182366 A CN97182366 A CN 97182366A CN 1127584 C CN1127584 C CN 1127584C
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Abstract
一种通过有机化合物与阴极接触、使有机化合物电化学还原的方法,其中阴极包括一种由导电材料制成的载体和一种用冲积法在载体上原位形成的导电的阴极极化层。
Description
技术领域
本发明涉及一种有机化合物电化学还原的方法。
背景技术
迄今,有机化合物的电化学还原仅在个别情况下能在工业规模上应用,例如用于丙烯腈的阴极二聚。因为就经济性而言,电流密度不够高,这就意味着其空时产率(STY)太低、日产率太低、产生氢气,由于有许多可能的还原步骤而使选择性太低,特殊的催化活性的阴极不能大规模得到和/或催化活性阴极的操作时间太短,因此迄今还不可能在工业上应用阴极电化学还原。
V.Anantharaman等在电化学会志,141期(1994)第2742-2752页描述了葡萄糖电化学加氢的计算机辅助模拟,并将这一模拟的结果与K.Park等的实验数据进行了比较,后者发表在电化学会志,132期(1985)第1850页及以后几页以及应用电化学杂志,16期(1986)第941页及以后几页。从该文献可以推测出,这一反应同样产生氢气,该反应用连续反应器进行,反应器有烧结的玻璃盘以及浸入其中作为阴极导电物质的粉状阮内镍。
从有关制备有机电化学方面的文献(例如电化学学报,39期(1994)第2109-2115页)还知道,用于制备电化学的阳极和阴极必须有一些特殊的电化学特性。这样的电极常常用已用适合的涂覆方法涂覆了的金属载体电极和碳质载体电极来制造,这些方法例如是等离子体喷涂、浸渍和烘烤、热压等(参见EP-B 0435434)。
这些常规制造方法的一个缺点是,催化活性层失活后的电极常常必须从电解设备中取出并进行器外再生,因此催化剂短的操作时间使得电化学合成系统的应用不经济。另一个缺点是催化活性层的制备很费事,并且难以达到对载体电极有足够粘合。在许多情况下,就经济性而言,经典的电极涂覆方法的开发努力仅仅在几个主要的工业过程、例如氯碱电解过程或丙烯腈的阴极二聚是合理的。工业多相催化剂的应用常常不是一种现实的选择,因为在热涂覆过程中的热转换或在冷粘合过程中活性区域的掩蔽不能被排除。
按照EP-B 0479052,在一种从工艺用水和流出液中分离金属离子的方法中使用这样一种催化活性电极,它被制成一种在多孔基体上有细分散催化剂材料悬浮液的灌注过滤层。
发明内容
鉴于上述现有技术,本发明的一个目的是提供这样一种还原有机化合物的方法,一方面该方法有高的空时产率,在多种可还原化合物的情况下有高的选择性,另一方面在还原过程中该方法不成生氢气,并可以工业规模应用。
根据本发明,这一目的用这样一种有机化合物电化学还原的方法来达到,它使有机化合物与一种阴极接触,其中该阴极包括一种导电材料制成的载体以及一种用冲积法在载体上原位形成的导电性阴极化层,在操作状态中,通过所述层的压力降来稳定所述电极。
在新方法的范围内,在操作状态中,它涉及在用冲积法形成的导电阴极极化层处,通过压力降来稳定的催化活性电极。为了进行再生,可通过物流反向而使催化活性电极再次悬浮,例如可用过滤的方法卸出或用抽吸的方法取出。所以,有机化合物的还原在这样一系统中进行,该系统适合于在过程内形成和卸除催化活性电极,这仅仅需要已在化学装置的操作实践中建立的一些干预手段,例如切换泵和最终的控制元件。
导电材料用作导电的阴极极化层的载体,可提到的例子是这样一些材料,例如合金钢、钢、镍、镍合金、钽、镀铂的钽、钛、镀铂的钛、石墨、电极炭和类似的材料及其混合物。
载体最好为可渗透的多孔材料,即载体有许多孔。它们可由金属丝或碳纤维纺织成商业上可购得的过滤织物形成。常见的一些例子包括平纹组织型、斜纹组织型、经面斜纹组织型、链形组织型和缎纹组织型的过滤织物。也可使用有孔的金属箔、金属毡、石墨毡、流线式过滤器、筛网或多孔的烧结体作为板形或烛形的大面积载体。载体的孔径通常为5至300微米,优选50至200微米。总是应这样来设计载体,以便得到最大的开孔面积,使得在进行本发明的方法中要克服的压降仅是很小的。通常,准备用于本方法的载体的开孔面积优选至少约30%,更优选至少约20%、特别优选约50%,开孔面积至多约70%。
用于导电的阴极极化层的导电材料可为任何一种导电材料,只要它们能用冲积法在上面规定的载体上形成一层就行。
阴极极化层最好包含金属、导电的金属氧化物或碳质材料,例如炭(特别是活性炭)、炭黑或石墨或其中两种或两种以上的混合物。
所用的金属优选包括所有典型的加氢金属,特别是元素周期表第I族、第II族和第VIII副族的金属,特别是Co、Ni、Fe、Ru、Rh、Re、Pd、Pt、Os、Ir、Ag、Cu、Zn、Pb和Cd,其中Ni、Co、Ag和Fe优选用阮内镍、阮内钴、阮内银和阮内铁,其中所有的都可用杂质金属搀杂,这些杂质金属例如是Mo、Cr、Au、Mn、Hg、Sn或元素周期表的其他元素,特别是S、Se、Te、Ge、Ga、P、Pb、As、Bi和Sb。
本发明所用的金属优选以细分散形式和/或活化了的形式存在。
也可使用导电的金属氧化物,例如磁铁石。
此外,阴极极化层也可只通过上面规定的碳质材料冲积而成。
另外,阴极可通过在碳质材料、特别是活性炭上将上述金属和导电氧化物冲积在载体上而原位制成。
所以,本发明还涉及这里提及的一类方法,在所有情况下,将含有一种金属或一种导电性的金属氧化物或其两种或两种以上的混合物的阴极极化层涂覆到活性炭上。
其中特别值得提到的是含有Pd/C、Pt/C、Ag/C、Ru/C、Re/C、Rh/C、Ir/C、Os/C和Cu/C的阴极极化层,它们也可任选用杂质金属或元素周期表其他元素,优选S、Se、Te、Ge、Ga、P、Pb、As、Bi和Sb搀杂。
此外,冲积到载体上的上述金属可呈毫微簇团形式,其制备方法例如在DE-A-4408512中公开,它们冲积在例如金属和碳质材料表面上。
另外,阴极极化层还可含有导电的辅剂,该辅剂可提高上述金属、金属氧化物或毫微簇团对载体的粘合力以及增大阴极、导电氧化物例如磁铁石和碳的表面积,特别值得提及的碳是活性炭、炭黑、碳纤维和石墨。
在本方法的另一实施方案中,使用这种一种阴极,它用以下方法制得:首先将导电的辅剂冲积到载体上,然后用这样一些金属原位搀杂在涂覆了的电极上的辅剂,这些金属用第I族、第II族/或第VIII副族金属的盐还原得到。优选使用的上述金属盐为金属卤化物、金属磷酸盐、金属硫酸盐、金属氯化物、金属碳酸盐、金属硝酸盐以及有机酸的金属盐,优选甲酸盐、乙酸盐、丙酸盐和苯甲酸盐、特别优选乙酸盐。
在这种情况下,本发明使用的阴极通过上述金属或金属氧化物直接冲积到载体上、或在导电的辅剂涂覆后再冲积到载体上原位制成。
总是这样来选择形成上面规定的层的颗粒平均粒度以及层的厚度,以便确保过滤压力降和水力流通量的最佳比例以及最佳的传质。平均粒度通常为约1至约400微米、优选约30至150微米,层厚通常为约0.05至约20毫米、优选约0.1至约5毫米。
在本文中应该注意的是,在本发明的方法中,载体的孔径通常大于形成层的颗粒的平均粒度,以致在载体上形成层时,两个或两个以上的颗粒通过空隙形成桥,其优点是,在载体上形成层不会使含有要还原的有机化合物的溶液流动受到任何明显的阻碍。优选的是,载体的孔径为形成层的颗粒的平均粒度的大约2至4倍。当然,在本发明的范围内,也可使用孔径小于形成层的颗粒的平均粒度的载体,虽然在这种情况下应密切注意所形成的层对物流的阻碍程度。
正如上面已经提到的,本发明所用的阴极是通过形成层的组分对导电载体的冲积而原位制成的,即含有形成层的颗粒的溶液灌注载体,一直到所述溶液中所有的固体冲积或保留在载体上为止。
还原完成后或催化活性层报废后,可通过简单改变流向的方法将它与载体分开,并可独立于还原过程而进行处理或再生。将废催化剂层从系统中完全除去后,可用形成层的颗粒多次涂覆载体,当所述的颗粒已完全冲积后,再继续有机化合物的还原。
本发明方法中的电流密度通常为约100至约10000安培/米2,优选约1000至约4000安培/米2。
含有要还原的有机化合物的溶液的流量通常为约1至约4000米3/(米2×小时),优选约50至约1000米3/(米2×小时)。对于通常为约1×104帕(绝压)至约4×106帕、优选约4×104帕至约1×106帕的系统压力来说,在本发明所用的流量下,层的压降为约1×104帕至约2×105帕,优选约2.5×104至约7.5×104帕。
本发明的方法通常在约-10℃至溶剂或溶剂混合物的沸点下进行,但是20至约50℃、特别是接近室温的温度是优选的。
视待还原的化合物而定,本发明的方法可在酸性介质中进行,即pH值小于7、优选为-2至5、更优选0至3;可在中性介质中进行,即pH值为约7;也可在碱性介质中进行,即pH值大于7、优选为9至14,特别是12至14。
特别优选的是,反应在常温和常压下进行。
在本发明的方法范围内,所用的电解池的类型、电极的形状和排列无任何决定性影响,以致在原则上可使用任何一种通常在电化学中使用的电解池。
作为例子,可提及以下两种设备:
a)
未分隔的电解池
有平行板电极排列或有烛型电极的无分隔电解池优选用于这样一些情况,在这些情况下,无论原料或是产物都不受阳极过程的不良影响,或者不会相互反应。电极优选按平行板排列,因为这一实施方案使电极间狭窄的间隙(1至10毫米、优选3毫米)与均匀的电流分布相结合起来。
b)
分隔的电解池
有平行板电极排列或有烛型电极的分隔电解池优选用于这样一些情况,在这些情况下,阴极电解液必须与阳极电解液分开,以便防止化学副反应或以便简化随后的材料分离。可以用离子交换膜、微孔膜、隔膜、不导电的材料制成的过滤器织物、烧结玻璃盘和多孔陶瓷形式分开所使用的介质。优选使用离子交换膜,特别是阳离子交换膜,反过来优选使用这样一些膜,它们由四氟乙烯和含有磺基的全氟单体的共聚物制成。优选的是,电极在分隔的电解池中均匀地作平行板排列,因为这一实施方案使电极间狭窄的间隙(两间隙都为0至10毫米、优选阳极为0毫米、阴极为3毫米)与均匀的电流分布相结合起来。优选的是,起分开作用的介质直接取决于阳极。
两种设备的共同点是阳极的设计。通常,所用的适合电极材料为有孔的材料,例如网、金属丝网、薄片、成型的丝网、格栅和平滑的金属片。在平行板电极排列的情况下,制作成平板片形式;而在烛型电极的实施方案中,制作成圆柱形排列形式。
阳极材料及其涂料的选择取决于阳极电解液溶剂。在有机系统中,优选使用石墨电极;而在含水系统中,优选使用有低氧超电势的材料或涂料。在本文中,所提及的酸性阳极电解液的例子是有导电夹层的钛或钽载体,而第IV族第VI副族的导电混合氧化物涂覆到该夹层中,它们用铂族金属和金属氧化物搀杂。
对于碱性的阳极电解液来说,优选使用铁阳极或镍阳极。
原则上,可用于本发明方法的溶剂包括所有的质子溶剂,即含有或释放质子的溶剂和/或能形成氢键的溶剂,例如水、醇类、胺类、羧酸类等,溶剂中也可混有非质子传递极性溶剂,例如THF。在本文中,优选使用低碳醇,例如甲醇、乙醇、1-丙醇、异丙醇、1-丁醇、仲丁醇或叔丁醇和醚类,例如乙醚、1,2-二甲氧基乙烷、呋喃、四氢呋喃以及二甲基甲酰胺,因为它们能保持导电性。还优选使用水,可能与上述醇类、醚类和二甲基甲酰胺中的一种或多种混合,其中水与甲醇、THF或DMF的混合物是特别优选的。
作为上述醇类的替代物,还可使用相应的酸类或胺类。
所用的羧酸优选为脂肪酸,其中可提及以下的酸:
甲酸、乙酸、丙酸、丁酸、戊酸、己酸、庚酸、辛酸、壬酸、癸酸、十一烷酸、月桂酸、十三烷酸、肉豆蔻酸、十五烷酸、棕榈酸、十七烷酸、硬脂酸、十九烷酸、异丁酸、异戊酸。
如果使用不溶于上述溶剂中的有机化合物,则它们可借助表面活性物质、特别是高碳醇作为溶剂或溶剂添加剂不难引入溶液中,特别值得提到的是脂肪醇。在本文中,脂肪醇指的是以下醇类:
1-己醇、1-庚醇、1-辛醇、1-壬醇、1-癸醇、1-十一烷醇、10-十一烷-1-醇、1-十二烷醇、1-十三烷醇、1-十一烷醇、1-十五烷醇、1-十六烷醇、1-十七烷醇、1-十八烷醇。
当然,根据本发明,在不同碳原子上带有羟基的相应醇类同样也可使用。
如果使用高碳醇或高碳羧酸或高碳胺,应考虑到转化必须在相对较高的温度下进行,以便使得到的溶液粘度维持在为进行这一转化可接受的范围内。
本发明的还原通常在支持性电解质的存在下进行。加入它以便调节电解质溶液的导电率和/或控制反应的选择性。电解质的浓度通常为约0.1至约10、优选约1至5%(重量),在每一情况下都按反应混合物计。可能使用的支持性电解质包括质子酸,例如有机酸,其中可以提到的是甲磺酸、苯磺酸或甲苯磺酸;以及包括无机酸、例如硫酸和磷酸。此外,所用的支持电解质也可为中性盐。在本文中,适合的阳离子为锂、钠、钾金属阳离子,也可为四烷基铵阳离子,例如四甲基铵、四乙基铵、四丁基铵和二丁基二甲基铵。要提到的阴离子为:氯根、四氟硼酸根、磺酸根类,例如甲磺酸根、苯磺酸根、甲苯磺酸根、硫酸根,例如硫酸根、甲基硫酸根、乙基硫酸根、磷酸根,例如甲基磷酸根、乙基磷酸根、二甲基磷酸根、二苯基磷酸根、六氟磷酸根、膦酸根,例如甲基膦酸甲酯根和苯基膦酸甲酯根。
碱性化合物也是适用的,例如氢氧化物类、碳酸盐类、碳酸氢盐类和碱金属或碱土金属的醇盐类,醇盐类阴离子中优选使用甲醇盐、乙醇盐、丁醇盐和异丙醇盐。
在这些碱性化合物中适合的阳离子仍包括上述的阳离子。
从上述可直接得知,本发明的方法不仅使用待还原有机化合物在适合溶剂中的均相溶液,而且也可在两相系统中进行,该两相系统由含有至少一种上面规定的有机溶剂和待还原的有机化合物的第一相以及含水的第二相组成。
本发明的电化学还原既可连续进行,也可间歇进行。在两种反应方式中,首先通过冲积法在载体上形成催化活性层来原位制成阴极。为此,用细分散的金属和/或导电的金属氧化物和/或毫微簇团和/或碳质材料的悬浮液灌注载体,即材料冲积,一直到基本上悬浮液中所有的材料都保留在载体上为止。可用肉眼观察到是否发生这种情况,例如借助悬浮液,在冲积开始时悬浮液是混浊的,后来变得透明。
另外,如果要冲积夹层,则用形成夹层的材料的悬浮液灌注载体,一直到基本上所用的材料都保留在载体上为止。用上述步骤使形成阴极极化层的材料冲积。
如果使用夹层,存在另一种灌注载体的选择,即向夹层提供一种待向载体层掺杂的金属盐的溶液或悬浮液,还存在另一种还原的选择,即将适合的电压施加到电解池上,使上述溶液或悬浮液中存在的金属阳离子在阴极处原位还原。
阴极的制备完成后,将要还原的有机化合物送入系统,并通过将预先精确规定的电量送入系统,使有机化合物还原。在本发明方法的范围内,送入电量的准确控制使得可能平稳地分离部分还原的化合物。
在用作原料的有机化合物的完全还原的情况下,对于特别平稳进行的还原来说,选择性为至少70%、通常大于80%以及大于95%。
在制成的产物的分离过程中,存在这样的选择余地,即通过使电解池中的流向反向来替换可能报废了的催化剂,其结果是冲积层不再与载体接触,催化剂例如可通过抽吸或过滤含有催化剂的悬浮液而除去。
当新的层再次象上述那样制在以后,可送入新的原料,并进行转化。
而且,转化步骤(还原)、催化剂的更换以及重新转化(还原)也可交替进行,如上所述,阴极首先用冲积法原位制备,然后将要还原的有机化合物送入,并进行转化,转化完成后改变电解池内的流向,例如用过滤的方法除去废催化剂,然后再用形成阴极极化层的新材料再次制成阴极,随后继续还原。
当然,在转化、废催化剂层的除去和阴极的再制作之间的交替可重复任何次数,其结果是,本发明的方法不仅可间歇进行,而且可连续进行,特别是使再生时间或催化剂更换时间明显缩短。
在本发明方法的另一优选实施方案中,有至少一个阴极和共用的阴极电解液回路的电解装置在类似均相连续反应器一样的稳态中操作。这就意味着,催化剂一旦冲积以后,就可维持一定的原料和产物浓度。为此,反应溶液通过泵经过电化学活性阴极连续循环,原料连续供给循环回路,产物连续从该循环回路取出,以致反应器中的物料在整个时间内保持不变。
与间歇操作的反应相比,这一工艺控制方式的优点在于简化了工艺控制,减少了复杂的设备。
可以用以下的设备结构来抵消与转化有关的缺点,需要提及的缺点是不利的浓度条件(即在转化的终点处有低的原料浓度和高的产物浓度)或在原处理过程中有更繁杂的分离,特别优选的设备结构是:
将至少两个电解装置串联,原料送入第一个装置,而产物从最后一个装置取出。这一操作方式确保第一个装置比最后一个装置在更加有利的浓度分布下操作。这就意味着,就所有的电解装置平均来说,比并联操作电解装置的反应得到更高的空时产率。
电解装置的这一串联安排在以下这样一些情况下是特别有优点的,其中在任何情况下所需的生产能力都要求装许多电解装置。
原则上,适合用于本发明方法的有机化合物包括任何一种含有可还原基团的有机化合物作为原料。可在这一方法中,得到的产物包括部分还原的化合物和完全还原的化合物,它与送入的总电荷有关。例如,从炔烃出发,可能得到相应的烯烃以及相应的完全加氢或还原的烷烃。
优选的是,有至少一个以下的可还原基团或键的有机化合物被还原:C-C双键、C-C三键、芳族C-C键、羰基、硫代羰基、羧基、酯基、C-N三键、C-N双键、芳族C-N键、硝基、亚硝基、碳-卤素单键,更优选的要还原的有机化合物选自:腈类、二腈类、硝基化合物、亚硝基化合物、饱和的和不饱和的酮类、氨基羧酸类。
具体地说,本发明的方法特别是使以下类型有机化合物的还原成为可能。
含有以下结构单元的有机化合物:
C=C (I)
上述定义包括含有至少一个C-C双键的所有有机化合物,例如不饱和的羧酸、被一个或多个烯基取代的芳族化合物以及分子式(A)的化合物式中,R1、R2、R3和R4各自独立为氢、烷基、芳基、芳烷基、烷芳基、烷氧基烷基、烷氧基或酰基。
含有结构单元(II)的有机化合物:
C≡C (II)
上述定义包括含有至少一个C-C三键的所有有机化合物,例如分子式(B)的化合物
R1-≡-R2 (B)式中,R1和R2规定如上。
上述定义包括含有至少一个上式芳环的所有有机化合物,例如所有芳族单环或环烃类以及分子式(C)的单环取代的芳族化合物式中,R1规定如上,X1可为卤素、烷氧基、NR′R″、SR′和P(R′)2,其中,R′和R″可为相同的或不同的,为如上对R1-R4所规定的。
含有结构单元(IV)的有机化合物式中,Y为NR′、P(R′)3、氧和/或硫,R′规定如上,R5可为如上对R1-R4规定的,另外还可为卤素,n为1-6中的一个整数,m为1-4中的一个整数,o和p为1-3中的一个整数,环上原子的最大数目为12。
含有结构单元(V)的有机化合物式中,X可为NR、氧和/或硫,其中R可为烷基、芳基、烷氧基、氢或羟基。
上述定义包括含有至少一个碳-杂原子双键的所有有机化合物,例如醛类、酮类和相应的硫代化合物和亚胺类,它可用以下分子式(E)表示式中,X、R1和R2规定如上,另外也可为脂族或芳族、饱和的或不饱和的羧酸衍生物,因为它有结构式R1COOR2,式中R1和R2也规定如上。
含有结构式(VI)的有机化合物
C≡N (VI)
上述定义包括含有至少一个C-N三键的所有有机化合物,例如二腈类和单腈类,后者用以下分子式(F)表示
R1-C≡N (F)式中,R1规定如上。
含有结构单元(VII)的有机化合物:
C-X2-OXRY 2 (VII)
上述定义包括含有至少一个上述类型键的所有有机化合物,即任何上述类型的杂羰基类似物,其中特别可提到硝基化合物和亚硝基化合物,所述的杂羰基类似物可用分子式(G)表示
R1-X2-OXRY 2 (G)式中,R1和R2规定如上,X2为氮、磷或硫、X为1-3中的一个整数,Y为0或1。
含结构单元(VIII)的有机化合物
C-Z (VIII)式中,Z为氟、氯、溴、碘和/或烷氧基。
上述定义包括含上述规定的卤原子或氧烷基的所有有机化合物,例如被至少一种上述基团取代的饱和烃或芳烃,例如它们可用以下两个分子式(H)和(I)表示式中,R1和R3和Z规定如上,R6为上述对R1-R4规定的,另外还可为甲酸根、三氟乙酸根、甲磺酸根和甲苯磺酸根。
具体地说,可以转化以下化合物或以下类型的化合物:
有至少一个对应于上述结构单元(I)和(II)的双键和/或三键的不饱和无环烃类可转化得到相应的饱和化合物,或者如果原料含有一个以上C-C双键和/或至少一个C-C三键、另一方面可转化得到有至少一个比原料少的双键或由双键代替三键的相应化合物。
1.在本文中,特别可提到的是有2-20、优选2-10、特别优选2-6个碳原子的烯类,例如乙烯、丙烯、1-丁烯、2-丁烯、异丁烯、1-戊烯、2-戊烯、3-戊烯、2-甲基-1-丁烯、3-甲基-1-丁烯、2-甲基-2-丁烯、1-己烯、2-己烯、3-己烯、1-庚烯、2-庚烯、3-庚烯、1-辛烯、2-辛烯、3-辛烯、4-辛烯、1-壬烯、2-壬烯、3-壬烯、4-壬烯、1-癸烯、2-癸烯、3-癸烯、4-癸烯、5-癸烯、1-十一烯、5-十一烯、1-十二烯、6-十二烯、1-十三烯、1-十四烯、1-十五烯、1-十六烯、1-十七烯和四氢香叶基丙酮。
有2-20、优选2-10、特别优选2-6个碳原子的炔类,例如乙炔、丙炔、丁炔、戊炔、3-甲基-1-丁炔、己炔、庚炔、辛炔、壬炔、癸炔、十一炔、十二炔、十三炔、十四炔、十五炔、十六炔、十七炔、甲基丁炔醇、脱氢里哪醇、部分氢化的脱氢里哪醇(hydrodehydrolinalool)和1,4-丁炔二醇。
有4-20、优选4-10个碳原子的多烯类和多炔类,例如丁二烯、丁二炔、1,3-戊二烯、1,4-戊二烯、戊二炔、1,3-己二烯、1,4-己二烯、1,5-己二烯、2,4-己二烯、己二炔、1,3,5-己三烯、1,3-庚二烯、2,4-庚二烯、1,6-庚二烯、1,3-辛二烯、1,7-辛二烯、2,4-辛二烯、3,5-辛二烯。
2.有至少一个双键和/或三键的不饱和单环烃类。
其中特别要提到的是有5-20、优选5-10个碳原子的环烯类,例如环戊烯、环己烯、环庚烯、环戊二烯、环己二烯、环庚三烯、环辛四烯和4-乙烯基环己烯;
有6-20个碳原子的环炔类,例如环庚炔和环辛二炔;
有6-12个碳原子的单环芳族化合物,例如苯、甲苯、1,2-二甲苯、1,3-二甲苯、1,4-二甲苯、1,2,4-三甲苯、1,3,5-三甲苯、1,2,3-三甲苯、乙苯、1-乙基-3-甲基苯、异丙苯、苯乙烯、芪和二乙烯基苯。
3.有8-20个碳原子的不饱和多环烃类,例如并环戊二烯、茚、萘、甘菊环、庚搭烯、亚联苯、as-indacene、s-indacene、苊、芴、phenalene、菲、蒽、荧蒽、acephenanthrylene、醋蒽烯、苯并[9,10]菲、芘、、并四苯、pleiadene、苉、苝和戊芬。
4.有8-20个碳原子的不饱和多环烃类,其碳原子通过单键或双键相互连接,例如联苯、1,2′-联萘、邻三联苯和对三联苯。
5.含有上述结构单元(IV)的不饱和杂环体系,该结构单元有5-12个环原子,环中含有1-3个氮原子和/或氧原子或硫原子以及至少一个C-C双键,所述不饱和杂环体系可转化得到这样的相应杂环化合物,它们有至少一个比原料少的双键,如果需要的话,还可转化得到相应的饱和杂环化合物,所述不饱和杂环体系例如是噻吩、苯并[b]-噻吩、二苯并[b,d]噻吩、噻蒽、吡喃例如2H-吡喃或4H-吡喃、呋喃、1,4-二氢呋喃和1,3-二氢呋喃、苯并呋喃和异苯并呋喃、4aH-异苯并吡喃、呫吨、1H-呫吨、吩氧硫杂环己二烯、吡咯、2H-吡咯、咪唑、4H-咪唑、吡唑、4H-吡唑、吡啶、吡嗪、嘧啶、哒嗪、中氮茚、异吲哚、3aH-异吲哚、吲哚、3aH-吲哚、吲唑、5H-吲唑、嘌呤、4H-喹啉嗪(4H-guinolizine)喹啉、异喹啉、2,3-二氮杂萘、1,8-二氮杂萘、喹喔啉、喹唑啉、噌啉、蝶啶、咔唑、8aH-咔唑、β-咔啉、菲啶、吖啶、啶、1,7-菲咯啉、吩嗪、吩吡嗪、吩噻嗪、吩噁嗪、噁唑、异噁唑、磷杂吲哚(phosphindole)、噻唑、异噻唑、呋咱、phosphinoline、苯并二氢吡喃、异苯并二氢吡喃、2-吡咯啉、3-吡咯啉、4-咪唑啉、2-吡唑啉、3-吡唑啉、二氮吲哚、异二氮吲哚、磷杂吲哚啉(phosphindoline)、1,2,3-噁二唑、1,2,4-噁二唑、1,3,4-噁二唑、1,2,5-噁二唑、1,2,3-噻二唑、1,2,4-噻二唑、1,3,4-噻二唑、1,2,5-噻二唑、1,2,3-三嗪、1,2,4-三嗪和1,3,5-三嗪。
6.在碳原子和除碳以外另一原子之间有至少一个双键有机化合物,另一原子选自氮、磷、氧和硫,正如上述结构式(V)规定的,氮和磷本身还可任选被取代,该化合物可转化得到相应的加氢化合物,其中特别要提到的是有2-20、优选2-10、特别优选2-6个碳原子的羰基化合物,例如脂肪族和芳族醛类,例如乙醛、丙醛、正丁醛、戊醛、己醛、庚醛、苯乙醛、丙烯醛、丁烯醛、苯甲醛、邻甲苯甲醛、间甲苯甲醛、对甲苯甲醛、水杨醛、肉桂醛、邻茴香醛、问茴香醛、对茴香醛。、烟碱醛、糠醛、甘油醛、乙醇醛、柠檬醛、香草醛、胡椒醛、乙二醛、丙二醛、琥珀醛、戊二醛、己二醛、苯二醛、间苯二醛和对苯二醛;酮类,例如丙酮、甲乙酮、2-戊酮、3-戊酮、2-己酮、3-己酮,甲基异丁基酮、环己酮、苯乙酮、苯基乙基酮、二苯酮、亚苄基丙酮、二亚苄基丙酮、亚苄基乙酰苯、2,3-丁二酮、2,4-戊二酮、2,5-己二酮、脱氧苯偶姻、查耳酮、苯偶酰、2,2′-糠偶酰、2,2′-糠偶姻、乙偶姻、苯偶姻、蒽酮和菲酮;
有1-20、优选2-10、更优选2-6个碳原子的饱和的和不饱和的脂族的和芳族的单羧酸和二元羧酸,例如甲酸、乙酸、丙酸、丁酸、辛酸、癸酸、月桂酸、肉豆蔻酸、棕榈酸、硬脂酸、丙烯酸、丙炔酸、甲基丙烯酸、丁烯酸、异丁烯酸和油酸、环己烷羧酸、苯甲酸、苯乙酸、邻甲苯甲酸、间甲苯甲酸、对甲苯甲酸、邻氯苯甲酸、对氯苯甲酸、邻硝基苯甲酸、对硝基苯甲酸、水杨酸、邻苯二甲酸、萘甲酸、肉桂酸、烟酸;以及取代的无环的环状羧酸,例如乳酸、苹果酸、扁桃酸、水杨酸、茴香酸、香草酸、藜
酸;氧代羧酸,例如二羟乙酸、丙酮酸、乙酰乙酸、乙酰丙酸;α-氨基羧酸,例如所有的α-氨基羧羧酸,如氨基丙酸、精氨酸、半胱氨酸、脯氨酸、色氨酸、酪氨酸和谷氨酰胺,以及其他的氨基羧酸,例如马尿酸、氨茴酸、氨基甲酸、肼基甲酸、脲基乙酸、氨基己酸、3-氨基苯甲酸和4-氨基苯甲酸;有2-20个碳原子的饱和的和不饱和的二元羧酸,例如草酸、丙二酸、琥珀酸、戊二酸、己二酸、庚二酸、辛二酸、壬二酸、癸二酸、马来酸、富马酸、邻苯二甲酸、间苯二甲酸、对苯二甲酸和山梨酸,以及上述羧酸的酯,其中应特别提到的是甲基酯,乙基酯和乙基己基酯。
7.含有结构单元(VI)的有机化合物,即有2-20、优选2-10、更优选2-6个碳原子的单腈和二腈,它们可转化分别得到相应的亚胺、胺或氨基腈和二胺。其中特别提到的是以下的腈:
乙腈、丙腈、丁腈、硬脂腈、丙烯腈、甲基丙烯腈、异巴豆腈、3-丁烯腈、丙炔腈、3-丁炔腈、2,3-丁二烯腈、戊二腈、马来二腈、富马二腈、己二腈、2-己烯-1,6-二腈、3-己烯-1,6-二腈、甲烷三腈、邻苯二甲腈、对苯二甲腈、1,6-二氰基己烷和1,8-二氰基辛烷。
8.含有至少一个上述结构单元(VII)的杂羰基类似物,其中特别应提到硝基化合物和亚硝基化合物,在所有情况下它们都可转化得到相应的还原化合物,例如胺。
其中特别提到的是有1-20、优选2-10、特别优选2-6个碳原子的饱和的或不饱和的、无环的或环状的硝基化合物和亚硝基化合物,例如亚硝基甲烷、亚硝基苯、4-亚硝基苯酚、4-亚硝基-N,N-二甲基苯胺和1-亚硝基萘、硝基甲烷、硝基乙烷、1-硝基丙烷、2-硝基丙烷、1-硝基丁烷、2-硝基丁烷、1-硝基-2-甲基丙烷、2-硝基-2-甲基丙烷、硝基苯、间二硝基苯、邻二硝基苯、对二硝基苯、2,4-二硝基甲苯、2,6-二硝基甲苯、邻硝基甲苯、间硝基甲苯、对硝基甲苯、1-硝基萘、2-硝基萘、1,5-二硝基萘、1,8-二硝基萘、1,2-二甲基-4-硝基苯、1,3-二甲基-2-硝基苯,、2,4-二甲基-1-硝基苯、1,3-二甲基-4-硝基苯、1,4-二甲基-2,3-二硝基苯、1,4-二甲基-2,5-二硝基苯、2,5-二甲基-1,3-二硝基苯、邻氯硝基苯、间氯硝基苯、对氯硝基苯、1,2-二氯-4-硝基苯、1,4-二氯-2-硝基苯、2,4-二氯-1-硝基苯、1,2-二氯-3-硝基苯、2-氯-1,3-二硝基苯、1-氯-2,4-二硝基苯、2,4,5-三氯-1-硝基苯、1,2,4-三氯-3,5-二硝基苯、五氯硝基苯、2-氯-4-硝基甲苯、4-氯-2-硝基甲苯、2-氯-6-硝基甲苯、3-氯-4-硝基甲苯、4-氯-3-硝基甲苯、硝基苯乙烯,1-(2′-呋喃基)-2-硝基乙醇、二硝基聚异丁烯、邻硝基苯胺、间硝基苯胺、对硝基苯胺、2,4-二硝基苯胺、2,6-二硝基苯胺、2-甲基-3-硝基苯胺、2-甲基-4-硝基苯胺、2-甲基-5-硝基苯胺、2-甲基-6-硝基苯胺、3-甲基-4-硝基苯胺、3-甲基-5-硝基苯胺、3-甲基-6-硝基苯胺、4-甲基-2-硝基苯胺、4-甲基-3-硝基苯胺、3-氯-2-硝基苯胺、4-氯-2-硝基苯胺、5-氯-2-硝基苯胺、2-氯-6-硝基苯胺、2-氯-3-硝基苯胺、4-氯-3-硝基苯胺、3-氯-5-硝基苯胺、2-氯-5-硝基苯胺、2-氯-4-硝基苯胺、3-氯-4-硝基苯胺、邻硝基苯酚、对硝基苯酚、间硝基苯酚、5-硝基-邻甲酚、4-硝基间甲酚2-硝基对甲酚、3-硝基对甲酚、4,6-二硝基邻甲酚和2,6-二硝基对甲酚。
9.被烷氧基取代的含卤素的芳族或脂族烃类或化合物(如上述结构单元VIII和分子式G和H规定的),它们可还原成相应的烃类。
作为原料特别提到的是有2-20个碳原子和1-6个、优选1-3个卤素原子的化合物,卤素原子优选为氯、氟、溴或碘、更优选氯、氟、溴、特别优选氯和溴,所述化合物例如是溴苯和三氯乙烯,当然也可为任何一种1-7项中提到的化合物以及一个或多个上述卤素原子或一个烷氧取代的化合物。
10.另外,例如在“Ullmanns工业化学百科全书”第4版(1976),第11卷第99-144页中描述的天然染料和合成染料,其中特别提到的是类胡萝卜素类,例如虾青素、胡萝卜素;醌类染料,例如联醌、紫草素、胭脂红酸、1,8-二羟基-3-甲基蒽醌;茜素染料,例如1,2-二羟基蒽醌、1,3-二羟基蒽醌、1,4-二羟基蒽醌、1,2,4-三羟基蒽醌、1,3-二羟基-2-甲基蒽醌和1,2-二羟基-1-甲氧基蒽醌;靛类染料,例如合成的或天然的靛蓝、靛蓝、anile和6,6′二溴靛蓝;吡喃酮染料,例如黄酮、异黄酮和黄烷酮。
特别优选的是,本发明的方法用于以下的转化过程:
1.饱和的脂族二无羧酸的二腈转化成相应的氨基腈,例如己二腈选择性转化成氨基己腈,同时显著避免完全还原成六亚甲基二胺。
以下形成阴极极化层的材料特别适合于这类转化过程:院内镍、阮内钴和Pd/C,该转化在中性至碱性介质中进行(pH值为7-14)。
2.芳族羧酸的二腈转化成相应的氨基腈也是可能的,例如邻苯二腈转化成2-氨基苄腈,以下形成阴极极化层的材料特别适用于这种情况:阮内镍、阮内钴,该转化也在中性至碱性介质中进行。
3.脂族或芳族羧酸二腈转化成相应的二胺,例如己二腈转化成六亚甲基二胺。
该转化优选用以下材料进行:如第1项规定的形成阴极极化层的那些材料(脂族羧酸的二腈)或如第2项规定的形成阴极极化层的那些材料(芳族羧酸的二腈);在每种情况下,该转化分别在第1项和第2项所述的条件下进行。
4.亚胺基异佛尔腈转化成异佛尔二胺
在这里使用如在第1项中规定的形成阴极极化层的相同材料和相同条件。
5.芳族二硝基化合物转化成相应的二氨基化合物,例如二硝基甲苯转化成二氨基甲苯。
为此,优选使用以一形成阴极极化层的材料:阮内镍和Pd/C,该转化在接近中性的介质中进行(pH值为5-7)。
6.芳族氨基羧酸转化成相应的氨基羟基衍生物,例如2-氨基苯甲酸转化成2-氨基苄醇,这类转化特别使用以下形成阴极极化层的材料:铜催化剂,例如Cu/C,该转化在酸性介质中进行(pH值为0-7)。
7.天然的和合成的染料转化成在一个或多个C-C双键上加氢的化合物,例如靛蓝转化成靛白和1,4-二羟基蒽醌转化成1,4-二羟基-2,3-二氢蒽醌,以下形成阴极极化层的材料特别适用:Pd/C、Pt/C、Rh/C和Ru/C,该转化在酸性介质中进行。
具体实施方式
实施例
实施例1
在阳极面积和阴极面积各为100厘米2的分隔电解池中,安装过滤板,它用50微米合金钢材料NO.1.4571的经面斜纹织物作为阴极覆盖。通过分开的滤液管线,滤液可以过滤织物下面的空腔中排出。
所用的阳极是钛阳极,用于使氧释放,它用Ta/Ir混合氧化物涂覆。所用的分隔介质是Nafion-324阳离子交换膜(从杜邦公司商购)。分隔的电解池装在有泵循环管线的双循环电解设备中。
转化按以下顺序间歇进行:
1100克5%浓度的硫酸水溶液用作阳极电解液。
通过将5克Vinclozoline[(RS)-3-(3,5-二氯苯基)-5-甲基-5-乙烯基-唑啉-2,4-二酮]溶于500克水、375克醇、375克异丁醇和65克乙酸的混合物中来制备阴极电解液。阴极环路装有1200克阴极电解液料。
根据滴定检测,在反应以前阴极电解液料不含氯。
当滤液出口关闭时,将15克石墨粉加到循环的阴极电解液环路中,并分散在循环回路中。通过将阴极电解液循环关闭和打开滤液出口来进行冲积。阴极隔室的压力升至4×105帕,滤液流量为12升/小时。接着用相同的方式再将5克催化剂(Degussa Type E101N/D,10%Pd/C)冲积。在30分钟内,施加20安培的直流电流,实验开始时它需要35伏的电压,而在实验结束时需要7.5伏电压。
根据滴定检测,在反应的产物中检测出850ppm氯,对应于转化率为90%。
用气相色谱对得到产物的分析,确定了以下转化:
以下实施例涉及己二腈(ADN)还原成六亚甲基二胺(HDA),以后的实施例在以下的设备中进行。
电解池:流动池型分隔电解池
膜: Nafion-324
阳极: DeNora DSA(阳极面积:100厘米2)
阴极: 合金钢材料No.1.4571的装甲链(阴极面积:100厘米
2,孔径:50微米)
流量: 通过阴极的流量大约20升/小时。
1200克2%浓度的硫酸用作阳极电解液。
阴极电解液由693克甲醇、330克水、22克NaOH、55克己二腈(0.509摩尔)和7.5克阮内镍(BASF H1-50)的混合物组成。
转化按如下进行:
首先给两个电解池隔室装料,然后将阮内镍对阴极冲洗10分钟。
然后在30-40℃之间,在常压下,用1000安培/米2的电流密度进行电解。在8.5F/摩尔ADN后停止电解。用电解分离出NaOH后,用蒸镏法分离产物。得到56克六亚甲基二胺(95%,按所用的ADN量计)。
实施例3
使用实施例2中相同的反应设备、相同的阳极电解液和相同的阴极电解液,将己二腈转化成6-氨基己腈(ACN),按实施例2中相同的方式制备阴极和进行电解,不同的是在仅4F/摩尔ADN以后中止电解。NaOH分离以后,接着进行蒸馏,分离出38.7克(0.34摩尔,68%ADN)氨基己腈、16%六亚甲基二胺和14%ADN。生成氨基己腈的选择性为79%和生成六亚甲基二胺的选择性的18.6%。
实施例4
使用实施例2中相同的设备和相同的阳极电解液进行以下转化。所用的阴极电解液为110克(0.92摩尔)苯乙酮、638克甲醇、330克水、22克NaOH和7.5克阮内镍的混合物。
按实施例2中相同的方式制备阴极和进行转化,不同的是,在仅2.3F/摩尔苯乙酮以后中止电解。
用1升水稀释后,用5×200毫升MTBE(甲基叔丁基醚)萃取、蒸发和蒸馏的方法分离产物,得到101.3克1-苯基乙醇(产率:90%,按苯乙酮计)。
实施例5
使用实施例2中相同的设备和相同的阳极电解液进行2-环己酮生成环己醇的还原。所用的阴极电解液为737克甲醇、330克水、11克NaOH、22克2-环己酮和7.5克阮内镍的混合物。该转化按实施例2进行,不同的是,在6F/摩尔2-环己酮后中止电解。用蒸馏法将得到的产物浓缩到270克,用500毫升水稀释,并用5×200毫升MTBE萃取。然后蒸馏有机相,得到21.7克环己醇,它对应于产率95%,按2-环己酮计。
实施例6
该实施例在实施例2相同的设备中进行。1100克1%浓度的硫酸用作阳极电解液。阳极电解液由418克甲醇、318克蒸馏水、297克甲基硫酸钠溶液(浓度7.4%,甲醇溶液)、55克环己酮肟(0.487摩尔)和8克铜粉的混合物组成。
转化按如下进行:
首先给电解池隔室装料,然后将铜粉对上述阴极冲洗10分钟。然后在30-50℃之间,在常压下,用1000安培/米2的电流密度进行电解。按所用的肟计,施加12F/摩尔的电荷。
为了处理产物,用氢氧化钠溶液使阴极电解液的pH值为13,过滤出铜粉,将滤液浓缩到639克,每次用100克MTBE萃取5次。干燥和除去溶剂后,蒸馏粗产品。分离出35.2克环己胺(产率73%,按所用的肟计)作为反应产品。
实施例7
该实施例在实施例2相同的设备中进行。1100克1%浓度的硫酸作为阳极电解液。阴极电解液由418克甲醇、330克蒸馏水、297克甲基硫酸钠溶液(浓度7.4%,在甲醇中)、55克2-丁炔-1,4-二醇(0.64摩尔)和15克阮内镍(BASF H1-50)的混合物组成。
转化按类似实施例6的方式进行:施加4.5F/摩尔的电荷,按所用的二醇计。
为了处理产物,过滤阴极电解液,将绝大部分滤液蒸发,然后蒸馏粗产品。可分离出23克丁二醇-1,4和12.4克2-丁烯-1,4-二醇作为反应产品。
实施例8
该实施例在实施例2相同的设备中进行。1100克1%浓度的硫酸用作阳极电解液。阴离电解液由704克甲醇、330克蒸馏水、11克硫酸、55克硝基苯(0.447摩尔)和8克铜粉的混合物组成。
转化按类似实施例6的方式进行:施加6.45F/摩尔的电荷,按基质计。
为了处理产物,用氢氧化钠溶液将阴极电解液的pH值定在13,过滤出铜粉,将滤液浓缩到597克,然后每次用100克MTBE萃取5次。干燥和除去溶剂后,蒸馏粗产品。可分离出26.2克苯胺反应产品。
实施例9
该实施例在实施例2相同的设备中进行,不同的是用合金钢制成的流线式过滤器(孔径100微米)作为阴极。1100克1%浓度的硫酸用作阳极电解液。阴极电解液由806克甲醇、377克蒸馏水、52克氢氧化钠溶液、48克2-噻吩基乙腈(0.391摩尔)和30克阮内镍(BASFH1-50)的混合物组成。
该转化在21℃和电流密度1000安培/米2下进行。原料分14批料加入。施加6.45F/摩尔电荷,按基质计。
为了处理产物,过滤出镍粉,用硫酸中和阴极电解液并用蒸馏法除去甲醇。将pH值调到13后,用MTBE进行萃取。干燥和除去溶剂后,蒸馏粗产品。可分离出37克噻吩基乙胺作为反应产品。
实施例10
该实施例在实施例2相同的设备中进行,不同的是用镀铂的钛制成的流线式过滤器(孔径100微米)作为阴极。1200克1%浓度的硫酸用作阳极电解液。阴极电解液由651克乙二醇二甲醚、651克蒸馏水、28克氢氧化钠溶液、70克2-噻吩基乙腈(0.569摩尔)和50克阮内镍(BASF H1-50)的混合物组成。
该转化在23℃和电流密度1000安培/米2下进行。施加5.5F/摩尔的电荷,按基质计。
为了处理产物,过滤出镍粉,用4%氢氧化钠与滤液混合并用Nacl饱合。相分离后蒸馏。可分离出45克噻吩基乙胺作为反应产品。
实施例11
该实施例在实施例2相同的设备中进行,不同的是,用镀铂的钛制成的流线式过滤器(孔径100微米)作为阴极。1200克1%浓度的硫酸用作阳极电解液。阴极电解液由882克甲醇、420克蒸馏水、28克氢氧化钠溶液、70克藜
基氰化物(0.395摩尔)和50克阮内镍(BASFH1-50)的混合物组成。
该转化在21℃和电流密度1000安培/摩尔下进行。施加4F/摩尔的电荷,按基质计。
为了处理产物,过滤出镍粉,用蒸馏法从滤液中除去甲醇,每次用100克MTBE萃取剩下的粗产品水溶液5次。干燥和除去溶剂后,蒸镏粗产品。可分离出54.5克高藜
基胺作为反应产品。
Claims (8)
1.一种使有机化合物电化学还原的方法,它通过有机化合物与阴极接触而实现,其特征在于,阴极包括一种由导电材料制成的载体和一种用冲积法在载体上原位形成的导电的阴极极化层,在操作状态中,通过在所述层的压力降来稳定所述电极。
2.根据权利要求1的方法,其特征在于,阴极极化层含有一种金属、一种导电的金属氧化物或一种碳质材料或其两种或两种以上的混合物。
3.根据权利要求1或2的方法,其特征在于,阴极极化层含有一种元素周期表第I族、第II族或第VIII副族的金属,为游离的金属、导电的金属氧化物或其两种或两种以上的混合物。
4.根据权利要求1或2的方法,其特征在于,阴极极化层含有涂覆到活性炭上的一种金属或一种导电的金属氧化物或其两种或两种以上的混合物。
5.根据权利要求1或2的方法,其特征在于,阴极极化层含有阮内镍、阮内钴、阮内银或阮内铁。
6.根据权利要求1或2的方法,其特征在于,由导电材料制成的载体有许多孔。
7.根据权利要求1或2的方法,其特征在于,有至少一个下列可还原基团或键的有机化合物被还原:C-C双键、C-C三键、芳族C-C键、羰基、硫代羰基、羧基、酯基、C-N三键、C-N双键、芳族C-N键、硝基、亚硝基、碳-卤素单键。
8.根据权利要求1或2的方法,其特征在于,选自如下的有机化合物被还原:腈类、二腈类、硝基化合物类、二硝基化合物类、饱和的和不饱和的酮类、氨基羧酸类。
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