CN110606806B - 一种纳米钌催化合成伯胺的方法 - Google Patents
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- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 229910052707 ruthenium Inorganic materials 0.000 title claims abstract description 32
- 238000000034 method Methods 0.000 title claims abstract description 20
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 15
- 238000006555 catalytic reaction Methods 0.000 title claims abstract description 14
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 title claims abstract 7
- 239000003054 catalyst Substances 0.000 claims abstract description 23
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims abstract description 16
- 235000011114 ammonium hydroxide Nutrition 0.000 claims abstract description 16
- 229910021536 Zeolite Inorganic materials 0.000 claims abstract description 14
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000002808 molecular sieve Substances 0.000 claims abstract description 14
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000010457 zeolite Substances 0.000 claims abstract description 14
- -1 aldehyde compound Chemical class 0.000 claims abstract description 13
- 239000002608 ionic liquid Substances 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 6
- 238000000926 separation method Methods 0.000 claims abstract description 5
- 238000009776 industrial production Methods 0.000 abstract description 3
- 238000010189 synthetic method Methods 0.000 abstract description 3
- 230000003197 catalytic effect Effects 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 150000003141 primary amines Chemical class 0.000 description 15
- 238000010438 heat treatment Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 description 1
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
- 238000003917 TEM image Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- OVWYEQOVUDKZNU-UHFFFAOYSA-N m-tolualdehyde Chemical compound CC1=CC=CC(C=O)=C1 OVWYEQOVUDKZNU-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
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Abstract
本发明公开了一种纳米钌催化合成伯胺的方法，包括将醛基化合物在PEG功能化离子液体稳定的纳米钌及HY沸石分子筛催化剂存在下与氨水、氢气一步反应生成伯胺,反应完成后通过温度控制实现催化剂与产物的高效分离。催化剂循环使用5次，催化活性和化学选择性都能得到较好的保持。本发明合成路线简单,合成方法新颖,工艺简便,产品收率和纯度高,催化剂廉价易得,不影响环境,适于工业化生产。
Description
技术领域
本发明涉及一种纳米钌催化合成伯胺的方法。
背景技术
含氮化合物，特别是伯胺类化合物广泛用于合成聚合物，染料，表面活性剂，药物和农用化学品。利用氨作为氮源将醛或酮（尤其是天然产物中容易获取的醛或酮）直接胺化成伯胺是一种绿色环保的伯胺类化合物获取方法。
发明内容
本发明提供了一种纳米钌催化合成伯胺的方法，包括将醛基化合物在PEG功能化离子液体稳定的纳米钌及HY沸石分子筛催化剂存在下与氨水、氢气一步反应生成伯胺,反应完成后通过温度控制实现催化剂与产物的高效分离。催化剂循环使用多次，催化活性和化学选择性都能得到较好的保持。本发明合成路线简单, 合成方法新颖, 工艺简便, 产品收率和纯度高, 催化剂廉价易得, 不影响环境, 适于工业化生产。
所采用的技术方案是：一种纳米钌催化合成伯胺的方法,它包括如下内容：将醛基化合物在PEG功能化离子液体稳定的纳米钌及HY沸石分子筛催化剂存在下与氨水、氢气一步反应生成伯胺,反应完成后通过温度控制实现催化剂与产物的高效分离，回收的催化剂分离干燥后可循环使用。
上述的一种纳米钌催化合成伯胺的方法, 其特征是：它包括如下步骤：在无氧条件下，将醛基化合物在PEG功能化离子液体稳定的纳米钌及HY沸石分子筛催化剂存在下与氨水、氢气一步反应生成伯胺,反应完成后通过温度控制实现催化剂与产物的高效分离，回收的催化剂分离干燥后可循环使用。
上述的一种纳米钌催化合成伯胺的方法, 其特征是：醛基化合物与氨水、氢气一步反应生成伯胺的催化剂为PEG功能化离子液体稳定的纳米钌及HY沸石分子筛，PEG的分子量在200-20000之间，功能化离子液体阴离子为PF6，氨基酸阴离子,NTf2，OTf, BF4，AcO等。
上述的一种纳米钌催化合成伯胺的方法, 其特征是：所制备纳米钌催化剂的粒径在1-100nm之间，温控回收催化剂的温度控制在-50– +100oC 之间。
上述的一种纳米钌催化合成伯胺的方法, 其特征是：醛基化合物包括各种芳环有取代基团的醛基化合物，烷基侧链有取代基团的醛基化合物，醛基与芳环之间有取代基团的醛基化合物。
上述的一种纳米钌催化合成伯胺的方法, 其特征是：氨水的浓度为1%-34%之间，氢气压力为1-100atm之间。
本发明用于解决现有胺类化合物的合成方法路线长、收率低的问题。提出一种合成路线简单、合成方法新颖、工艺简便、收率高、原辅料价廉易得、环保、适用于工业生产的胺类化合物合成方法。
附图说明
图1是在[PEG-2000-BMIM][PF6]2制备的纳米钌的TEM图。
具体实施方式
下面结合实施例对本发明作进一步详细说明。
本专利中所用到的部分PEG功能化离子液体结构。
本专利中在[PEG-2000-BMIM][PF6]2制备的纳米钌的TEM表明，Ru纳米颗粒粒径在1.5-3.0 nm之间(图1)。
本发明通过大量的实验、筛选、优化反应条件优选出下面合成路线：
实施例1
在无氧条件下，向反应器中加入0.2mmol苯甲醛，0.0001mmol 0.3%纳米钌/[PEG-2000-BMIM][PF6]2，0.1g HY沸石分子筛，10equiv 氨水，充入1MPaH2，充分搅拌后升温至90oC反应5h,产物收率90.0%。分离出产物后催化剂进行干燥活化回收利用，第2-5次循环使用中目标产物收率分别为89.5%，92.3%，93.6%，91.5%。
实施例2
在无氧条件下，向反应器中加入0.2mmol苯甲醛，0.0001mmol 0.3%纳米钌/[PEG-2000-BMIM][Pro]2，0.1g HY沸石分子筛，10equiv 氨水，充入1MPaH2，充分搅拌后升温至90oC反应5h, 产物收率93.6%。
实施例3
在无氧条件下，向反应器中加入0.2mmol对甲氧基苯甲醛，0.0001mmol 0.3%纳米钌/[PEG-2000-BMIM][Pro]2，0.1g HY沸石分子筛，10equiv 氨水，充入1MPaH2，充分搅拌后升温至90oC反应5h, 产物收率83.5%。
实施例4
在无氧条件下，向反应器中加入0.2mmol对氯苯甲醛，0.0001mmol 0.3%纳米钌/[PEG-2000-BMIM][Pro]2，0.1g HY沸石分子筛，10equiv 氨水，充入1MPaH2，充分搅拌后升温至90oC反应5h, 产物收率88.6%。
实施例5
在无氧条件下，向反应器中加入0.2mmol间甲基苯甲醛，0.0001mmol 0.3%纳米钌/[PEG-2000-BMIM][Pro]2，0.1g HY沸石分子筛，10equiv 氨水，充入1MPaH2，充分搅拌后升温至90oC反应5h, 产物收率85.5%。
实施例6
在无氧条件下，向反应器中加入0.2mmol呋喃甲醛，0.0001mmol 0.3%纳米钌/[PEG-2000-BMIM][Pro]2，0.1g HY沸石分子筛，10equiv 氨水，充入1MPaH2，充分搅拌后升温至90oC反应5h, 产物收率81.0%。
实施例7
在无氧条件下，向反应器中加入0.2mmol苯乙酮，0.0001mmol 0.3%纳米钌/[PEG-2000-BMIM][Pro]2，0.1g HY沸石分子筛，10equiv 氨水，充入1MPaH2，充分搅拌后升温至100oC反应10h, 产物收率63.5%。
实施例8
在无氧条件下，向反应器中加入0.2mmol2-醛基吡咯化合物，0.0001mmol 0.3%纳米钌/[PEG-2000-BMIM][Pro]2，0.1g HY沸石分子筛，10equiv 氨水，充入1MPaH2，充分搅拌后升温至100oC反应20h, 产物收率60.0%。
Claims (3)
1.一种纳米钌催化合成伯胺的方法,其特征在于,它包括如下步骤：在无氧条件下，将芳香醛基化合物在PEG功能化离子液体稳定的纳米钌及HY沸石分子筛催化剂存在下与氨水、氢气一步反应生成伯胺,反应完成后通过温度控制实现催化剂与产物的分离，回收的催化剂分离干燥后可循环使用，所述PEG功能化的离子液体为：
2.根据权利要求1所述的一种纳米钌催化合成伯胺的方法,其特征是：所制备纳米钌催化剂的粒径在1-100nm之间，温控回收催化剂的温度控制在-50–+100℃之间。
3.根据权利要求1所述的一种纳米钌催化合成伯胺的方法,其特征是：氨水的浓度为1％-34％之间，氢气压力为1-100atm之间。
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