CN112939783B - 一种氧气选择性氧化醇制备醛或酮的方法 - Google Patents
一种氧气选择性氧化醇制备醛或酮的方法 Download PDFInfo
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Abstract
本发明公开了一种氧气选择性氧化醇类化合物制备醛或酮的新方法。该方法使用醇为反应物,氧气为氧化剂,磁性负载型季鏻盐为非均相催化剂,通过高选择性氧化反应制备醛或酮。反应结束后,通过外磁场即可方便实现催化剂相与产物相的分离,催化剂能够良好回收循环利用。本发明催化效率高、催化剂稳定性好,反应条件温和,操作简便,反应高效与高选择性、氧化过程环境友好。
Description
技术领域
本发明属于化工技术领域,具体涉及一种磁性负载型季鏻盐催化氧气选择性氧化醇类化合物制备醛或酮的方法。
背景技术
醛和酮是重要的化工原料,广泛应用于精细化学品、有机中间体和高分子材料等化合物的生产。目前,国内外生产醛酮的主要方法来源于醇的氧化,传统的氧化方法主要使用金属氧化物如氧化铬、氧化锰、氧化钌或高碘盐、活化DMSO等作为氧化剂,这些方法存在很多缺点,比如大量的金属污染物生成、反应中需要使用大化学计量的氧化剂、反应选择性差、大量副产物的生成导致产品分离与纯化困难、环境污染严重等。因此,醇的选择性氧化为醛酮是一个极具挑战性的课题,开发高效、绿色环保的醇的高选择性氧化方法具有重要的理论和实际意义。
氧气价格便宜,是所能得到的最丰富、廉价、安全及环境友好的氧化剂,不会对环境造成危害,近年来,探索和发展以氧气作为清洁氧化剂的催化反应体系备受关注,以氧气为氧化剂催化氧化醇制备醛或酮被认为是一种很具有发展前景的清洁氧化途径。报道的催化剂或催化体系如Cu(NO3)2/4-HO-TEMPO、(NH4)4[CuMo6O18(OH)6]、CTOHH-DNA、硝酸铁/TEMPO/无机氯化物、(bpy)CuI/TEMPO、CeO2/光催化和其它体系都能实现催化醇类化合物的选择性氧化为醛或酮类化合物。但是这些方法或多或少存在催化剂活性不高、反应选择性较低、操作条件苛刻、反应成本高、工艺复杂等问题。因此研究开发操作简单、高效、高选择性、环境友好的氧气氧化醇类化合物为醛或酮的反应体系具有重要的意义。
发明内容
本发明提供一种操作简单、高效、绿色环保的氧气选择性氧化醇类化合物制备醛或酮的新方法。
本发明的技术方案是,一种氧气选择性氧化醇制备醛或酮的方法,以醇类化合物为原料,磁性负载型季鏻盐为非均相催化剂,氧气为氧化剂,催化下发生高选择性氧化反应,通过外磁场分离回收催化剂相,得到的目标产物。
进一步地,本发明所用催化剂的制备方法参考文献(R.Fehrmann,A.Riisager,M.Haumann,Supported ionic liquids:Fundamentals and applications,Wiley-VCHVerlag,Weinheim,2014;吴海伟,新型季鏻盐和咪唑盐的合成及其抗菌性能研究,暨南大学硕士学位论文,2018;R.S.Cutting,V.S.Coker,N.D.Telling,R.L.Kimber,C.I.Pearce,B.L.Ellis,R.S.Lawson,G.van der Laan,R.A.D.Pattrick,D.J.Vaug,Environ.Sci.Technol.2010,44,7,2577-2584;Z.Rashid,H.Naeimi,A.H.Zarnani,M.Nazari,M.R.Nejadmoghaddamde,R.Ghahremanzadeh,RSC Adv.2016,6,36840-36848)来进行,所述催化剂的结构如下:
载体金属的种类M是Sc,Cr或Mn中的任意一种,季鏻盐阴离子anion为GaCl4,P2W18O62,PMo12O40中的任意一种。
进一步地,所述催化剂为ScFe2O4@SiO2@PIL-GaCl4、CrFe2O4@SiO2@PIL-P2W18O62或ScFe2O4@SiO2@PIL-PMo12O40。
进一步地,所述催化剂用量为醇物料质量的1~30%,优选1~20%。
进一步地,反应温度为20~80℃,优选30~60℃。
进一步地,反应时间为1~12小时,优选1-8小时。
进一步地,反应过程中通入氧气,氧气流量为1-30mL/min,优选1-15mL/min。
进一步地,回收的催化剂进行催化循环使用。
本发明采用磁性负载型季鏻盐催化剂催化氧气选择性氧化醇类化合物制备醛或酮,反应结束后,磁性非均相催化剂沉积在反应器底部,通过外磁场即可分离催化剂相和产物相,得到的产物进行GC分析,回收磁性催化剂不经处理即可进行循环使用,按比例投料进行下一批催化反应。
本发明与现有氧化技术相比,其优点为:(1)磁性负载型季鏻盐催化剂催化活性高,稳定性好,产物相和催化剂相易分离,催化剂可良好的回收循环使用。(2)氧化反应选择性好,醛或酮收率高、反应条件温和。(3)反应体系操作简单、绿色高效,不需要加入有机溶剂和其它助剂,反应过程环境友好。
附图说明
图1为催化剂ScFe2O4@SiO2@PIL-GaCl4、CrFe2O4@SiO2@PIL-P2W18O62和ScFe2O4@SiO2@PIL-PMo12O40的SEM图。
图2是实施例6中得到产品的气相色谱图。
具体实施方式
下面将结合实施例对本发明的实施方案进行详细描述,但是本领域技术人员将会理解,下列实施例仅用于说明本发明,而不应视为限定本发明的范围。
实施例1
在反应器中加入苯甲醇(0.05mol),ScFe2O4@SiO2@PIL-GaCl4(0.3g),通入氧气,氧气流量为8mL/min,后在50℃继续搅拌反应3小时。反应结束后通过外磁场即可分离回收催化剂相,得到产物苯甲醛,产物进行GC分析,收率95.0%,选择性99.4%。
实施例2
在反应器中加入苯甲醇(0.05mol),CrFe2O4@SiO2@PIL-GaCl4(0.35g),通入氧气,氧气流量为10mL/min,后在55℃继续搅拌反应6小时。反应结束后通过外磁场即可分离回收催化剂相,得到产物苯甲醛,产物进行GC分析,收率85.7%,选择性98.1%。
实施例3
在反应器中加入苯甲醇(0.05mol),MnFe2O4@SiO2@PIL-GaCl4(0.5g),通入氧气,氧气流量为12mL/min,后在65℃继续搅拌反应5小时。反应结束后通过外磁场即可分离回收催化剂相,得到产物苯甲醛,产物进行GC分析,收率76.5%,选择性91.6%。
实施例4
在反应器中加入苯甲醇(0.05mol),ScFe2O4@SiO2@PIL-P2W18O62(0.35g),通入氧气,氧气流量为10mL/min,后在55℃继续搅拌反应5小时。反应结束后通过外磁场即可分离回收催化剂相,得到产物苯甲醛,产物进行GC分析,收率89.7%,选择性98.5%。
实施例5
在反应器中加入苯甲醇(0.05mol),CrFe2O4@SiO2@PIL-P2W18O62(0.3g),通入氧气,氧气流量为8mL/min,后在50℃继续搅拌反应4小时。反应结束后通过外磁场即可分离回收催化剂相,得到产物苯甲醛,产物进行GC分析,收率91.5%,选择性98.9%。
实施例6
在反应器中加入苯甲醇(0.05mol),ScFe2O4@SiO2@PIL-PMo12O40(0.3g),通入氧气,氧气流量为8mL/min,后在50℃继续搅拌反应2小时。反应结束后通过外磁场即可分离回收催化剂相,得到产物苯甲醛,产物进行GC分析,收率96.2%,选择性99.8%。
实施例7
在反应器中加入苯甲醇(0.05mol),MnFe2O4@SiO2@PIL-P2W18O62(0.4g),通入氧气,氧气流量为12mL/min,后在60℃继续搅拌反应5小时。反应结束后通过外磁场即可分离回收催化剂相,得到产物苯甲醛,产物进行GC分析,收率85.8%,选择性94.7%。
实施例8
在反应器中加入苯甲醇(0.05mol),CrFe2O4@SiO2@PIL-PMo12O40(0.4g),通入氧气,氧气流量为10mL/min,后在50℃继续搅拌反应4小时。反应结束后通过外磁场即可分离回收催化剂相,得到产物苯甲醛,产物进行GC分析,收率87.0%,选择性98.3%。
实施例9
在反应器中加入苯甲醇(0.05mol),MnFe2O4@SiO2@PIL-PMo12O40(0.3g),通入氧气,氧气流量为10mL/min,后在60℃继续搅拌反应4小时。反应结束后通过外磁场即可分离回收催化剂相,得到产物苯甲醛,产物进行GC分析,收率83.5%,选择性97.0%。
实施例10
在反应器中加入苯甲醇(0.05mol),ScFe2O4@SiO2(1.2g),通入氧气,氧气流量为30mL/min,后在80℃继续搅拌反应10小时。反应结束后,产物苯甲醛进行GC分析,收率70.8%,选择性93.1%。
实施例11
在反应器中加入苯甲醇(0.05mol),PIL-PMo12O40(0.8g),通入氧气,氧气流量为20mL/min,后在70℃继续搅拌反应8小时。反应结束后,产物苯甲醛进行GC分析,收率65.7%,选择性94.5%。
实施例12
在反应器中加入对甲基苯甲醇(0.05mol),ScFe2O4@SiO2@PIL-GaCl4(0.3g),通入氧气,氧气流量为8mL/min,后在50℃继续搅拌反应2小时。反应结束后通过外磁场即可分离回收催化剂相,得到产物对甲基苯甲醛,产物进行GC分析,收率96.2%,选择性99.1%。
实施例13
在反应器中加入对甲氧基苯甲醇(0.05mol),ScFe2O4@SiO2@PIL-PMo12O40(0.3g),通入氧气,氧气流量为8mL/min,后在50℃继续搅拌反应1.5小时。反应结束后通过外磁场即可分离回收催化剂相,得到产物对甲氧基苯甲醛,产物进行GC分析,收率97.5%,选择性99.8%。
实施例14
在反应器中加入对硝基苯甲醇(0.05mol),ScFe2O4@SiO2@PIL-GaCl4(0.35g),通入氧气,氧气流量为10mL/min,后在50℃继续搅拌反应4小时。反应结束后通过外磁场即可分离回收催化剂相,得到产物对硝基苯甲醛,产物进行GC分析,收率90.5%,选择性98.3%。
实施例15
在反应器中加入对氟苯甲醇(0.05mol),ScFe2O4@SiO2@PIL-GaCl4(0.35g),通入氧气,氧气流量为10mL/min,后在55℃继续搅拌反应3小时。反应结束后通过外磁场即可分离回收催化剂相,得到产物对氟苯甲醛,产物进行GC分析,收率91.7%,选择性98.6%。
实施例16
在反应器中加入2-噻吩甲醇(0.05mol),ScFe2O4@SiO2@PIL-PMo12O40(0.4g),通入氧气,氧气流量为10mL/min,后在50℃继续搅拌反应2.5小时。反应结束后通过外磁场即可分离回收催化剂相,得到产物2-噻吩甲醛,产物进行GC分析,收率94.2%,选择性99.0%。
实施例17
在反应器中加入4-吡啶甲醇(0.05mol),ScFe2O4@SiO2@PIL-PMo12O40(0.4g),通入氧气,氧气流量为10mL/min,后在50℃继续搅拌反应3小时。反应结束后通过外磁场即可分离回收催化剂相,得到产物4-吡啶甲醛,产物进行GC分析,收率92.3%,选择性98.8%。
实施例18
在反应器中加入环己醇(0.05mol),ScFe2O4@SiO2@PIL-PMo12O40(0.4g),通入氧气,氧气流量为12mL/min,后在50℃继续搅拌反应4小时。反应结束后通过外磁场即可分离回收催化剂相,得到产物环己酮,产物进行GC分析,收率92.5%,选择性99.2%。
实施例19
将实施例1中的催化剂回收,按实施例1中的各条件进行催化反应,重复使用回收催化剂5次,实验结果显示催化剂活性不减,产物苯甲醛收率为90~94%,选择性为98~99%。
实施例20
将实施例7中的催化剂回收,按实施例7中的各条件进行催化反应,重复使用回收催化剂5次,实验结果显示催化剂活性不减,产物苯甲醛收率为92~96%,选择性为98~99%。
Claims (11)
2.根据权利要求1所述的方法,其特征在于:所述催化剂为ScFe2O4@SiO2@PIL-GaCl4、CrFe2O4@SiO2@PIL-P2W18O62或ScFe2O4@SiO2@PIL-PMo12O40。
3.根据权利要求1所述的方法,其特征在于:所述催化剂用量为醇物料质量的1~30%。
4.根据权利要求1所述的方法,其特征在于:催化剂用量为醇物料质量的1~20%。
5.根据权利要求1所述的方法,其特征在于:反应温度为20~80℃。
6.根据权利要求1所述的方法,其特征在于:反应温度为30~60℃。
7.根据权利要求1所述的氧气选择性氧化醇制备醛或酮的方法,其特征在于,反应时间为1~12小时。
8.根据权利要求1所述的氧气选择性氧化醇制备醛或酮的方法,其特征在于,反应时间为1-8小时。
9.根据权利要求1所述的氧气选择性氧化醇制备醛或酮的方法,其特征在于,反应过程中通入氧气,氧气流量为1-30mL/min。
10.根据权利要求1所述的氧气选择性氧化醇制备醛或酮的方法,其特征在于,反应过程中通入氧气,氧气流量为1-15mL/min。
11.根据权利要求1所述的方法,其特征在于:回收的催化剂进行催化循环使用。
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