CN117550551B - 一种pncnp-钯钳形过渡金属氢化物催化氨硼烷醇解脱氢的方法 - Google Patents
一种pncnp-钯钳形过渡金属氢化物催化氨硼烷醇解脱氢的方法 Download PDFInfo
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- 238000006356 dehydrogenation reaction Methods 0.000 title claims abstract description 32
- 229910052763 palladium Inorganic materials 0.000 title claims abstract description 29
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 229910000045 transition metal hydride Inorganic materials 0.000 title claims abstract description 27
- 238000006136 alcoholysis reaction Methods 0.000 title claims abstract description 23
- 210000000080 chela (arthropods) Anatomy 0.000 title claims abstract description 21
- 238000000034 method Methods 0.000 title claims abstract description 17
- TVJORGWKNPGCDW-UHFFFAOYSA-N aminoboron Chemical compound N[B] TVJORGWKNPGCDW-UHFFFAOYSA-N 0.000 title claims abstract description 16
- JBANFLSTOJPTFW-UHFFFAOYSA-N azane;boron Chemical compound [B].N JBANFLSTOJPTFW-UHFFFAOYSA-N 0.000 claims abstract description 33
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000003054 catalyst Substances 0.000 claims abstract description 14
- 239000007810 chemical reaction solvent Substances 0.000 claims abstract description 11
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 5
- 239000002994 raw material Substances 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 4
- 229910010082 LiAlH Inorganic materials 0.000 claims description 2
- 101150003085 Pdcl gene Proteins 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims description 2
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- 238000010189 synthetic method Methods 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 25
- 239000001257 hydrogen Substances 0.000 abstract description 25
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 25
- 230000003197 catalytic effect Effects 0.000 abstract description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- -1 and the like Chemical compound 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000011232 storage material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- SIYIAGQBGDVEPK-UHFFFAOYSA-N borane hydrazine Chemical compound B.B.NN SIYIAGQBGDVEPK-UHFFFAOYSA-N 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
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- 235000019253 formic acid Nutrition 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
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- C01B3/00—Hydrogen; Gaseous mixtures containing hydrogen; Separation of hydrogen from mixtures containing it; Purification of hydrogen
- C01B3/02—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1845—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing phosphorus
- B01J31/1875—Phosphinites (R2P(OR), their isomeric phosphine oxides (R3P=O) and RO-substitution derivatives thereof)
- B01J31/188—Amide derivatives thereof
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/824—Palladium
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Abstract
本发明公开了一种PNCNP‑钯钳形过渡金属氢化物催化氨硼烷醇解脱氢的方法,是以氨硼烷为原料、醇为反应溶剂,在PNCNP‑钯钳形过渡金属氢化物的催化作用下进行醇解脱氢反应。所使用的PNCNP‑钯钳形过渡金属氢化物[2,6‑(tBu2PNH)2C6H3]PdH相比于其它钳形配合物作为催化剂的催化体系,具有更高的释氢速率,在反应的前5s内就会释放出2当量的氢气。可以从1当量的氨硼烷中释放完全3当量的H2,本发明的催化体系持续添加氨硼烷可以多次循环释氢。
Description
技术领域
本发明属于催化脱氢技术领域,具体涉及一种PNCNP-钯钳形过渡金属氢化物催化氨硼烷醇解脱氢的方法。
背景技术
氢能燃烧值高、来源广泛、对环境零污染,被誉为21世纪绿色清洁高效的新能源,开发高效的储氢技术对现代社会持续发展意义重大。在甲酸、甲醛、氨硼烷、水合肼等众多化学储氢材料中,氨硼烷 (NH3BH3, AB) 因其易于处理、室温下稳定、无毒、氢含量较高(19.6 wt%) 等优点成为强有力的储氢材料候选者。
开发高效的脱氢催化剂是促进氨硼烷大规模应用的关键因素。在过去的几十年里,研究者们对氨硼烷脱氢的均相催化剂体系进行了广泛的研究,其中过渡金属钳形配合物在均相催化转化中具有优越的热稳定性及化学稳定性,而被引入氨硼烷脱氢的催化反应,但还鲜有报道。在仅有的报道中,钳形配合物的催化脱氢效率可达每个AB释放1-2.5当量的H2,且转化时间较长。具体可参考以下文献:1、Denney, M. C.; Pons, V.; Hebden,T. J.; Heinekey, M.; Goldberg, K. I. Efficientcatalysis of ammonia boranedehydrogenation[J].J. Am. Chem. Soc.2006,128, 12048-12049.
2、Bhattacharya, P.; Krause, J. A.; Guan, H. Mechanistic studies ofammonia borane dehydrogenation catalyzed by iron pincer complexes[J].J. Am. Chem. Soc.2014,136, 11153-11161.
3、Buss, J. A.; Edouard, G. A.; Cheng, C.; Shi, J.; Agapie, T.Molybdenum Catalyzed Ammonia Borane Dehydrogenation: Oxidation StateSpecificMechanisms[J].J. Am. Chem. Soc.2014,136, 11272-11275.
4、Luconi, L.; Demirci, U. B.; Peruzzini, M.; Giambastiani, G.;Rossin, A. Ammonia boraneand hydrazine bis (borane) dehydrogenation mediatedby an unsymmetrical (PNN) ruthenium pincer hydride: metal–ligand cooperationfor hydrogen production[J].Sustainable Energy&Fuels.2019,3, 2583-2596.
5、Nugent, J. W.; García-Melchor, M.; Fout, A. R. Cobalt-catalyzedammonia boranedehydrogenation: Mechanistic insight and isolation of a cobalthydride-amidoborane complex[J].Organometallics.2020,39, 2917-2927.
基于以上论述,本发明提出利用PNCNP-钯钳形氢化物(Pd-H)高效催化AB脱氢的方法。相比于其他方法(以上文献),本发明是钳形配合物催化体系中室温下H2释放程度最高且用时最短的,且可进行多次循环催化释氢。
发明内容
本发明旨在开发利用PNCNP-钯钳形过渡金属氢化物催化氨硼烷高效、快速醇解脱氢。为实现上述目的,本发明提供如下技术方案:
本发明提供一种PNCNP-钯钳形过渡金属氢化物催化氨硼烷醇解脱氢的方法,是以氨硼烷为原料、醇为反应溶剂,在PNCNP-钯钳形过渡金属氢化物的催化作用下进行醇解脱氢反应。
进一步,所述反应溶剂为乙醇、甲醇或异丙醇,用量为氨硼烷的5-10倍,以重量计。
进一步,所述反应溶剂为甲醇,用量为氨硼烷的3-5倍,以重量计。
进一步,所述PNCNP-钯钳形过渡金属氢化物为 [2,6- (tBu2PNH)2C6H3]PdH,可以通过两种不同的途径合成,PNCNP-钯钳形过渡金属氢化物参考文献Chang, J.; Ding, M.;Mao, J. X.; Zhang, J.; Chen, X. Reactionsand catalytic applications of aPNCNP pincer palladium hydride complex[J].Dalton Transactions,2022,51,17602-17608.的方法合成。
具体合成方法如下:
方案一:在无水无氧条件下,537 mg, 1.0 mmol[2,6-(tBu2PNH)2C6H3]PdCl和 76mg, 2.0 mmol LiAlH4 溶于30 mL THF中,室温下搅拌1 h;反应结束后抽干溶剂,然后用甲苯 15 mL×3次萃取,浓缩甲苯并在甲苯里重结晶得到白色结晶固体407 mg,以81%产率获得了 [2,6- (tBu2PNH)2C6H3]PdH ;
方案二:将282 mg,0.5 mmol[2,6- (tBu2PNH)2C6H3]PdNO3、700 mg, 10mmolKOCH3和 20 mLTHF 的混合物在室温下超声处理5 h,离心所得悬浮液在减压条件下蒸发溶剂;用甲苯 15 mL×3次萃取固体残留物;合并萃取液,对溶液进行浓缩并重结晶,以85%的产率获得了[2,6- (tBu2PNH)2C6H3]PdH。
进一步,所述PNCNP-钯钳形过渡金属氢化物的用量为氨硼烷用量的0~5 wt%。
进一步,醇解脱氢反应是在室温条件下进行。
进一步,在反应溶剂为甲醇时,1 mmol氨硼烷可在5s内释放出2 mmol的H2, 17min内释放完全3 mmol的H2。
进一步,在第一次运行后向反应体系中加入更多的氨硼烷,则可以观察到H2继续释放,并且在相同条件下运行多次后催化剂仍保持活性。
与现有技术相比,本发明的有益效果是:
(1)本发明所使用的PNCNP-钯钳形过渡金属氢化物 [2,6- (tBu2PNH)2C6H3]PdH相比于其它钳形配合物作为催化剂的催化体系,具有更高的释氢速率,在反应的前5s内就会释放出2当量的氢气。
(2)本发明可以从1当量的氨硼烷中释放完全3当量的H2,据我们所知,这是钳形配合物催化体系中H2释放程度最高的。
(3)本发明的催化体系持续添加氨硼烷可以多次循环释氢。
附图说明
图1是相同催化体系中不同溶剂的释氢速率图;
图2是相同催化体系中EtOH为溶剂时不同催化剂负载量的释氢速率图。
具体实施方式
实施例1 PNCNP-钯钳形过渡金属氢化物催化氨硼烷醇解脱氢实验步骤
在一个充满水的100 mL量气管内,通过水置换法监测反应期间释放的气体体积。在开始催化醇解释氢反应之前,先检测装置的气密性。然后称取31.5 mg氨硼烷置于带单颈支口的10 mL圆底Schlenk反应瓶中,瓶口用橡胶塞密封,固定于磁力搅拌器上。支口通过皮管连接刻度线装满水的量气管用于收集气体。称取10 mg (2wt%) PNCNP-钯钳形过渡金属氢化物 [2,6- (tBu2PNH)2C6H3]PdH催化剂分散于3 mL甲醇中,用气密注射器通过橡胶塞将溶液加入反应瓶中,保持室温下匀速搅拌,开始催化反应(t:sec)并计时,间隔适当时间记录量气管中液面刻度,记录收集到的氢气体积,直到无气泡冒出,计算出释氢量。
实施例2:不同溶剂对氨硼烷释氢反应的影响
采用实施例1的醇解脱氢方法,改变反应体系中的醇为甲醇、乙醇、异丙醇,结果如表1所示。
从上述表格中可以看出,不同的溶剂对氨硼烷释氢的速率影响较大,其中甲醇可使反应体系中的氨硼烷在前5s内释放2当量的氢气,释氢速率极快。
实施例3:不同催化剂用量对氨硼烷释氢反应的影响
采用实施例1的醇解脱氢方法,其中因甲醇当溶剂时前几秒的反应速率极快,为了便于区分,改用乙醇作为溶剂。在相同的反应体系中改变催化剂PNCNP-钯钳形过渡金属氢化物 [2,6- (tBu2PNH)2C6H3]PdH的负载量,结果如表2所示。
从上述表格可以看出催化剂PNCNP-钯钳形过渡金属氢化物 [2,6- (tBu2PNH)2C6H3]PdH的负载量对氨硼烷醇解释氢具有很大的影响,在氨硼烷醇解反应中,增加催化剂的负载量可以加快氨硼烷脱氢的反应进程。
实施例4 考察催化剂对氨硼烷醇解释氢的循环效率
当反应体系无气泡产出时,立即加入新的一当量氨硼烷于反应体系中,则可以观察到连续的H2释放,并且在相同条件下运行七次后催化剂仍保持活性,尽管后几次运行的反应速率略有减慢,但总体上保持了较好的催化效果,结果如表3所示。
由此可知该PNCNP-钯钳形过渡金属氢化物 [2,6- (tBu2PNH)2C6H3]PdH催化剂能够高效催化氨硼烷醇解脱氢且循环性能优异。
Claims (6)
1.一种PNCNP-钯钳形过渡金属氢化物催化氨硼烷醇解脱氢的方法,其特征在于,是以氨硼烷为原料、醇为反应溶剂,在PNCNP-钯钳形过渡金属氢化物的催化作用下进行醇解脱氢反应;所述反应溶剂为乙醇、甲醇或异丙醇,用量为氨硼烷的50-100倍,以重量计;所述PNCNP-钯钳形过渡金属氢化物为 [2,6- (tBu2PNH)2C6H3]PdH,可以通过两种不同的途径合成,具体合成方法如下:
方案一:在无水无氧条件下,537 mg, 1.0 mmol[2,6-(tBu2PNH)2C6H3]PdCl 和 76 mg,2.0 mmol LiAlH4溶于30 mL THF中,室温下搅拌1 h;反应结束后抽干溶剂,然后用甲苯 15mL×3次萃取,浓缩甲苯并在甲苯里重结晶得到白色结晶固体407 mg,以81%产率获得了[2,6- (tBu2PNH)2C6H3]PdH ;
方案二:将282 mg,0.5 mmol [2,6- (tBu2PNH)2C6H3]PdNO3、700 mg, 10 mmolKOCH3和20 mLTHF 的混合物在室温下超声处理5 h,离心所得悬浮液在减压条件下蒸发溶剂;用甲苯 15 mL×3次萃取固体残留物;合并萃取液,对溶液进行浓缩并重结晶,以85%的产率获得了[2,6- (tBu2PNH)2C6H3]PdH。
2.如权利要求1所述的一种PNCNP-钯钳形过渡金属氢化物催化氨硼烷醇解脱氢的方法,其特征在于,所述反应溶剂为甲醇,用量为氨硼烷的50-75倍,以重量计。
3.如权利要求1所述的一种PNCNP-钯钳形过渡金属氢化物催化氨硼烷醇解脱氢的方法,其特征在于,所述PNCNP-钯钳形过渡金属氢化物的用量为氨硼烷用量的0~5 wt%。
4.如权利要求1所述的一种PNCNP-钯钳形过渡金属氢化物催化氨硼烷醇解脱氢的方法,其特征在于,醇解脱氢反应是在室温条件下进行。
5.如权利要求2所述的一种PNCNP-钯钳形过渡金属氢化物催化氨硼烷醇解脱氢的方法,其特征在于,在反应溶剂为甲醇时,1 mmol氨硼烷可在5s内释放出2 mmol的H2, 17min内释放完全3 mmol的H2。
6.如权利要求5所述的一种PNCNP-钯钳形过渡金属氢化物催化氨硼烷醇解脱氢的方法,其特征在于,在第一次运行后向反应体系中加入更多的氨硼烷,则可以观察到H2继续释放,并且在相同条件下运行多次后催化剂仍保持活性。
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