CN116273181A - 固体高熵催化剂及其制备和应用于制备呋喃丙烯醛的方法 - Google Patents
固体高熵催化剂及其制备和应用于制备呋喃丙烯醛的方法 Download PDFInfo
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- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2213—At least two complexing oxygen atoms present in an at least bidentate or bridging ligand
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Abstract
本发明涉及化工领域,尤其涉及一种固体高熵催化剂及其制备和应用于制备呋喃丙烯醛的方法。固体高熵催化剂的制备过程为,使用乙酰丙酮金属络合物0‑1mol,无水葡萄糖0‑1kg,十二烷基三甲基氯化铵即DTAC0‑1kg,油胺溶液0‑50L,充分搅拌20min待其溶解后,再超声2h,将完全溶解的溶液,在220℃的温度下保持5h,即得高熵催化剂溶液;向高熵催化剂溶液加入环己烷和乙醇混合液,离心洗涤3次后,在60℃真空干燥箱中干燥过夜,烘干后研磨即得高熵催化剂。本发明通过催化串联反应技术实现糠醛的高效、高选择性转化,所用原料廉价易得,反应条件温和,并且催化剂易于回收;与贵金属催化剂相比,具有经济性好、合成方法简单、以及可持续性强等优势。
Description
技术领域
本发明涉及化工领域,尤其涉及一种固体高熵催化剂及其制备和应用于制备呋喃丙烯醛的方法。
背景技术
糠醛作为生物质平台化合物,具有特殊的分子结构,可以发生多种类型的化学反应,制备一系列的生物质衍生品,其下游产品覆盖医药、涂料、树脂等多个行业。
目前,糠醛和脂肪醛的氧化-缩合反应也是一种有效增长碳链的方式,生成更长的碳氢化合物链和高价值的液体燃料。
此外,在之前的研究中,使用贵金属作为催化剂,但其使用成本高,工业应用受到限制。
因此我们设计与开发了实现糠醛高效利用的新型高活性催化剂。该催化剂具有安全高效,转化率高,选择性高,可循环,绿色经济等优点。
发明内容:
本发明的主要目的在于解决上述问题,提供一种固体高熵催化剂促进生物质基糠醛与脂肪醇选择性氧化-缩合制备呋喃丙烯醛的方法,采用固体高熵催化剂,可使糠醛与脂肪醇发生催化串联反应,反应方程式如图1。
为达到上述目的,本发明采用如下技术方案:
一种固体高熵催化剂的制备方法,固体高熵催化剂的制备过程为,使用乙酰丙酮金属络合物0-1mol,无水葡萄糖0-1kg,十二烷基三甲基氯化铵即DTAC0-1kg,油胺溶液0-50L,充分搅拌20min待其溶解后,再超声2h,将完全溶解的溶液,在220℃的温度下保持5h,即得高熵催化剂溶液;向高熵催化剂溶液加入环己烷和乙醇混合液,离心洗涤3次后,在60℃真空干燥箱中干燥过夜,烘干后研磨即得高熵催化剂。
所述的固体高熵催化剂的制备方法中,所使用乙酰丙酮金属络合物为乙酰丙酮铁、乙酰丙酮锰、乙酰丙酮钴、乙酰丙酮镍、乙酰丙酮铂或乙酰丙酮铝中的五种或五种以上,其中以上乙酰丙酮金属络合物均可用金属铜、铬、钒、镧、铈的乙酰丙酮络合物替换。
所述制备方法所制备的固体高熵催化剂,固体高熵催化剂的制备过程为:
使用乙酰丙酮金属络合物0-1mol,无水葡萄糖0-1kg,十二烷基三甲基氯化铵即DTAC质量0-1kg,油胺溶液0-50L;充分搅拌20min待其溶解后,再超声2h,将完全溶解的溶液,在220℃的温度下保持5h,即得高熵催化剂溶液,向高熵催化剂溶液加入环己烷和乙醇混合液,离心洗涤3次后,在60℃真空干燥箱中干燥过夜,烘干后研磨即得高熵催化剂;所使用乙酰丙酮金属络合物为乙酰丙酮铁、乙酰丙酮锰、乙酰丙酮钴、乙酰丙酮镍、乙酰丙酮铂或乙酰丙酮铝中的五种或五种以上,其中以上乙酰丙酮金属络合物均可用金属铜、铬、钒、镧、铈的乙酰丙酮络合物替换。
所述的固体高熵催化剂的应用方法,应用于生物质基糠醛与脂肪醇选择性氧化-缩合制呋喃丙烯醛的反应,其步骤是:将生物质基糠醛作为反应底物,使用醇作溶剂,加入固体高熵催化剂,添加入碱助剂,加热并搅拌,糠醛与脂肪醇发生催化串联反应,该方法以氧气为氧化剂进行。
所述的脂肪醇为乙醇、丙醇、异丙醇、丁醇、异丁醇、正戊醇、正己醇、正庚醇、正辛醇或异辛醇中的一种或几种。
所述的碱助剂为Li2CO3、Na2CO3、K2CO3、Cs2CO3、KHCO3、NaHCO3、LiOH、NaOH、KOH、SrOH、Ca(OH)2、CaO、甲酸钠、乙酸钠、丙酸钠、甲醇钠或乙醇钠中的一种或几种。
加热反应温度为0-240℃,反应时间为0-60h,搅拌速率为0-9000r/min。
所述的催化剂和反应底物糠醛质量百分比为0.0001-50%。
所述的反应氧化剂为氧气、空气、氧气混合气体、双氧水或者叔丁基过氧化氢中的一种。
本发明通过催化串联反应技术实现糠醛的高效、高选择性转化,所用原料廉价易得,反应条件温和,并且催化剂易于回收;与贵金属催化剂相比,具有经济性好、合成方法简单、以及可持续性强等优势。
附图说明:
图1是固体高熵催化剂促进生物质基糠醛与脂肪醇选择性氧化-缩合制备呋喃丙烯醛化学反应式。
具体实施方式:
为了使本发明所要解决的技术问题、技术方案及有益效果更加清楚、明白,以下以实例对本发明做进一步详细说明。
本发明具体操作方式如下:
称取一定量的生物质基糠醛作为反应底物,使用醇作溶剂,加入固体高熵催化剂,添加适量碱助剂,加入磁子,除去体系中的空气,充入一定压力的氧气,加热并搅拌,糠醛与脂肪醇发生催化串联反应。反应结束后通过针管和滤膜将高熵催化剂与溶液分离,再经气相色谱对产物进行分析。
实施例1:
固体高熵催化剂的制备方法及糠醛与乙醇发生催化串联反应时的应用:
将0.6g的无水葡萄糖和0.4g的十二烷基三甲基氯化铵(DTAC)加入到30mL油胺中,加入0.3mmol的乙酰丙酮金属络合物(Fe,Mn,Cu,La,Mg),充分搅拌20min待其溶解后,再超声2h,将完全溶解的溶液,在220℃的温度下保持5h,即得高熵催化剂,将高熵催化剂用环己烷和乙醇混合液,离心洗涤3次后,在60℃真空干燥箱中干燥过夜,烘干后研磨即得高熵催化剂。取0.025g上述催化剂,0.025gCs2CO3,0.1g糠醛加入到聚四氟乙烯高压反应釜中,再加入10mL乙醇溶剂,充入0.3MPaO2,搅拌加热到130℃保持2h。反应液过滤后,气相分析表明糠醛的转化率为73.62%,3-(2-呋喃基)丙烯醛的产率为71.51%。
实施例2:
固体高熵催化剂的制备方法及糠醛与正丙醇发生催化串联反应时的应用:
将0.6g的无水葡萄糖和0.4g的十二烷基三甲基氯化铵(DTAC)加入到30mL油胺中,加入0.3mmol的乙酰丙酮金属络合物(Fe,Mn,Cu,La,Mg),充分搅拌20min待其溶解后,再超声2h,将完全溶解的溶液,在220℃的温度下保持5h,即得高熵催化剂,将高熵催化剂用环己烷和乙醇混合液,离心洗涤3次后,在60℃真空干燥箱中干燥过夜,烘干后研磨即得高熵催化剂。取0.025g上述催化剂,0.025gCs2CO3,0.1g糠醛加入到聚四氟乙烯高压反应釜中,再加入10mL正丙醇溶剂,充入0.3MPaO2,搅拌加热到130℃保持2h。反应液过滤后,气相分析表明糠醛的转化率为81.92%,3-(2-呋喃基)-2-甲基-2-丙烯醛的产率为80.98%。
实施例3:
固体高熵催化剂的制备方法及糠醛与正丙醇发生催化串联反应时的应用:
将0.6g的无水葡萄糖和0.4g的十二烷基三甲基氯化铵(DTAC)加入到30mL油胺中,加入0.3mmol的乙酰丙酮金属络合物(Fe,Mn,Cu,La,Mg),充分搅拌20min待其溶解后,再超声2h,将完全溶解的溶液,在220℃的温度下保持5h,即得高熵催化剂,将高熵催化剂用环己烷和乙醇混合液,离心洗涤3次后,在60℃真空干燥箱中干燥过夜,烘干后研磨即得高熵催化剂。取0.025g上述催化剂,0.025gLiOH,0.1g糠醛加入到聚四氟乙烯高压反应釜中,再加入10mL正丙醇溶剂,充入0.3MPaO2,搅拌加热到80℃保持2h。反应液过滤后,气相分析表明糠醛的转化率为93.97%,3-(2-呋喃基)-2-甲基-2-丙烯醛的产率为92.11%。
实施例4:
固体高熵催化剂的制备方法及糠醛与正丁醇发生催化串联反应时的应用:
将0.6g的无水葡萄糖和0.4g的十二烷基三甲基氯化铵(DTAC)加入到30mL油胺中,加入0.3mmol的乙酰丙酮金属络合物(Fe,Mn,Cu,La,Mg),充分搅拌20min待其溶解后,再超声2h,将完全溶解的溶液,在220℃的温度下保持5h,即得高熵催化剂,将高熵催化剂用环己烷和乙醇混合液,离心洗涤3次后,在60℃真空干燥箱中干燥过夜,烘干后研磨即得高熵催化剂。取0.025g上述催化剂,0.025gLiOH,0.1g糠醛加入到聚四氟乙烯高压反应釜中,再加入10mL正丁醇溶剂,充入0.3MPaO2,搅拌加热到80℃保持2h。反应液过滤后,气相分析表明糠醛的转化率为99.77%,3-(2-呋喃基)-2-乙基-2-丙烯醛的产率为97.55%。
实施例5:
固体高熵催化剂的制备方法及糠醛与正戊醇发生催化串联反应时的应用:
将0.6g的无水葡萄糖和0.4g的十二烷基三甲基氯化铵(DTAC)加入到30mL油胺中,加入0.3mmol的乙酰丙酮金属络合物(Fe,Mn,Cu,La,Mg),充分搅拌20min待其溶解后,再超声2h,将完全溶解的溶液,在220℃的温度下保持5h,即得高熵催化剂,将高熵催化剂用环己烷和乙醇混合液,离心洗涤3次后,在60℃真空干燥箱中干燥过夜,烘干后研磨即得高熵催化剂。取0.025g上述催化剂,0.025gLiOH,0.1g糠醛加入到聚四氟乙烯高压反应釜中,再加入10mL正戊醇溶剂,充入0.3MPaO2,搅拌加热到80℃保持2h。反应液过滤后,气相分析表明糠醛的转化率为99%,3-(2-呋喃基)-2-丙基-2-丙烯醛的产率为88.14%。
实施例6:
固体高熵催化剂的制备方法及糠醛与正己醇发生催化串联反应时的应用:将0.6g的无水葡萄糖和0.4g的十二烷基三甲基氯化铵(DTAC)加入到30mL油胺中,加入0.3mmol的乙酰丙酮金属络合物(Fe,Mn,Cu,La,Mg),充分搅拌20min待其溶解后,再超声2h,将完全溶解的溶液,在220℃的温度下保持5h,即得高熵催化剂,将高熵催化剂用环己烷和乙醇混合液,离心洗涤3次后,在60℃真空干燥箱中干燥过夜,烘干后研磨即得高熵催化剂。取0.025g上述催化剂,0.025gLiOH,0.1g糠醛加入到聚四氟乙烯高压反应釜中,再加入10mL正己醇溶剂,充入0.3MPaO2,搅拌加热到80℃保持2h。反应液过滤后,气相分析表明糠醛的转化率为95%,3-(2-呋喃基)-2-丙基-2-丙烯醛的产率为87.17%。
实施例7:
固体高熵催化剂的制备方法及糠醛与正庚醇发生催化串联反应时的应用:将0.6g的无水葡萄糖和0.4g的十二烷基三甲基氯化铵(DTAC)加入到30mL油胺中,加入0.3mmol的乙酰丙酮金属络合物(Fe,Mn,Cu,La,Mg),充分搅拌20min待其溶解后,再超声2h,将完全溶解的溶液,在220℃的温度下保持5h,即得高熵催化剂,将高熵催化剂用环己烷和乙醇混合液,离心洗涤3次后,在60℃真空干燥箱中干燥过夜,烘干后研磨即得高熵催化剂。取0.025g上述催化剂,0.025gLiOH,0.1g糠醛加入到聚四氟乙烯高压反应釜中,再加入10mL正庚醇溶剂,充入0.3MPaO2,搅拌加热到80℃保持2h。反应液过滤后,气相分析表明糠醛的转化率为94.5%,3-(2-呋喃基)-2-丙基-2-丙烯醛的产率为86.37%。
实施例8:
固体高熵催化剂的制备方法及糠醛与正辛醇发生催化串联反应时的应用:将0.6g的无水葡萄糖和0.4g的十二烷基三甲基氯化铵(DTAC)加入到30mL油胺中,加入0.3mmol的乙酰丙酮金属络合物(Fe,Mn,Cu,La,Mg),充分搅拌20min待其溶解后,再超声2h,将完全溶解的溶液,在220℃的温度下保持5h,即得高熵催化剂,将高熵催化剂用环己烷和乙醇混合液,离心洗涤3次后,在60℃真空干燥箱中干燥过夜,烘干后研磨即得高熵催化剂。取0.025g上述催化剂,0.025gLiOH,0.1g糠醛加入到聚四氟乙烯高压反应釜中,再加入10mL正辛醇溶剂,充入0.3MPaO2,搅拌加热到80℃保持2h。反应液过滤后,气相分析表明糠醛的转化率为94.3%,3-(2-呋喃基)-2-丙基-2-丙烯醛的产率为85.55%。
实施例9:
固体高熵催化剂的制备方法及糠醛与正壬醇发生催化串联反应时的应用:将0.6g的无水葡萄糖和0.4g的十二烷基三甲基氯化铵(DTAC)加入到30mL油胺中,加入0.3mmol的乙酰丙酮金属络合物(Fe,Mn,Cu,La,Mg),充分搅拌20min待其溶解后,再超声2h,将完全溶解的溶液,在220℃的温度下保持5h,即得高熵催化剂,将高熵催化剂用环己烷和乙醇混合液,离心洗涤3次后,在60℃真空干燥箱中干燥过夜,烘干后研磨即得高熵催化剂。取0.025g上述催化剂,0.025gLiOH,0.1g糠醛加入到聚四氟乙烯高压反应釜中,再加入10mL正壬醇溶剂,充入0.3MPaO2,搅拌加热到80℃保持2h。反应液过滤后,气相分析表明糠醛的转化率为92.3%,3-(2-呋喃基)-2-丙基-2-丙烯醛的产率为83.35%。
实施例10:
固体高熵催化剂的制备方法及糠醛与正癸醇发生催化串联反应时的应用:将0.6g的无水葡萄糖和0.4g的十二烷基三甲基氯化铵(DTAC)加入到30mL油胺中,加入0.3mmol的乙酰丙酮金属络合物(Fe,Mn,Cu,La,Mg),充分搅拌20min待其溶解后,再超声2h,将完全溶解的溶液,在220℃的温度下保持5h,即得高熵催化剂,将高熵催化剂用环己烷和乙醇混合液,离心洗涤3次后,在60℃真空干燥箱中干燥过夜,烘干后研磨即得高熵催化剂。取0.025g上述催化剂,0.025gLiOH,0.1g糠醛加入到聚四氟乙烯高压反应釜中,再加入10mL正癸醇溶剂,充入0.3MPaO2,搅拌加热到80℃保持2h。反应液过滤后,气相分析表明糠醛的转化率为90.13%,3-(2-呋喃基)-2-丙基-2-丙烯醛的产率为81.34%。
实施例11:
固体高熵催化剂的制备方法及糠醛与正丙醇发生催化串联反应时的应用:
将0.6g的无水葡萄糖和0.4g的十二烷基三甲基氯化铵(DTAC)加入到30mL油胺中,加入0.3mmol的乙酰丙酮金属络合物(Fe,Mn,Cu,La,Mg),充分搅拌20min待其溶解后,再超声2h,将完全溶解的溶液,在220℃的温度下保持5h,即得高熵催化剂,将高熵催化剂用环己烷和乙醇混合液,离心洗涤3次后,在60℃真空干燥箱中干燥过夜,烘干后研磨即得高熵催化剂。取0.025g上述催化剂,0.025gK2CO3,0.1g糠醛加入到聚四氟乙烯高压反应釜中,再加入10mL正丙醇溶剂,充入0.3MPaO2,搅拌加热到130℃保持2h。反应液过滤后,气相分析表明糠醛的转化率为80.92%,3-(2-呋喃基)-2-甲基-2-丙烯醛的产率为79.84%。
实施例12:
固体高熵催化剂的制备方法及糠醛与正丙醇发生催化串联反应时的应用:
将0.6g的无水葡萄糖和0.4g的十二烷基三甲基氯化铵(DTAC)加入到30mL油胺中,加入0.3mmol的乙酰丙酮金属络合物(Fe,Mn,Cu,La,V),充分搅拌20min待其溶解后,再超声2h,将完全溶解的溶液,在220℃的温度下保持5h,即得高熵催化剂,将高熵催化剂用环己烷和乙醇混合液,离心洗涤3次后,在60℃真空干燥箱中干燥过夜,烘干后研磨即得高熵催化剂。取0.025g上述催化剂,0.025gCs2CO3,0.1g糠醛加入到聚四氟乙烯高压反应釜中,再加入10mL正丙醇溶剂,充入0.3MPaO2,搅拌加热到130℃保持2h。反应液过滤后,气相分析表明糠醛的转化率为76.4%,3-(2-呋喃基)-2-甲基-2-丙烯醛的产率为73.25%。
实施例13:
高固体高熵催化剂的制备方法及糠醛与正丙醇发生催化串联反应时的应用:
将0.6g的壳聚糖和0.4g的十二烷基三甲基氯化铵(DTAC)加入到30mL油胺中,加入0.3mmol的乙酰丙酮金属络合物(Fe,Mn,Cu,La,Mg),充分搅拌20min待其溶解后,再超声2h,将完全溶解的溶液,在220℃的温度下保持5h,即得高熵催化剂,将高熵催化剂用环己烷和乙醇混合液,离心洗涤3次后,在60℃真空干燥箱中干燥过夜,烘干后研磨即得高熵催化剂。取0.025g上述催化剂,0.025gCs2CO3,0.1g糠醛加入到聚四氟乙烯高压反应釜中,再加入10mL正丙醇溶剂,充入0.3MPaO2,搅拌加热到130℃保持2h。反应液过滤后,气相分析表明糠醛的转化率为58.14%,3-(2-呋喃基)-2-甲基-2-丙烯醛的产率为44.52%。
Claims (9)
1.一种固体高熵催化剂的制备方法,其特征在于:固体高熵催化剂的制备过程为,使用乙酰丙酮金属络合物0-1mol,无水葡萄糖0-1kg,十二烷基三甲基氯化铵即DTAC0-1kg,油胺溶液0-50L,充分搅拌20min待其溶解后,再超声2h,将完全溶解的溶液,在220℃的温度下保持5h,即得高熵催化剂溶液;向高熵催化剂溶液加入环己烷和乙醇混合液,离心洗涤3次后,在60℃真空干燥箱中干燥过夜,烘干后研磨即得高熵催化剂。
2.根据权利要求1中所述的固体高熵催化剂的制备方法,其特征在于:所使用乙酰丙酮金属络合物为乙酰丙酮铁、乙酰丙酮锰、乙酰丙酮钴、乙酰丙酮镍、乙酰丙酮铂或乙酰丙酮铝中的五种或五种以上,其中以上乙酰丙酮金属络合物均可用金属铜、铬、钒、镧、铈的乙酰丙酮络合物替换。
3.一种如权利要求1所述制备方法所制备的固体高熵催化剂,其特征在于,固体高熵催化剂的制备过程为:
使用乙酰丙酮金属络合物0-1mol,无水葡萄糖0-1kg,十二烷基三甲基氯化铵即DTAC质量0-1kg,油胺溶液0-50L;充分搅拌20min待其溶解后,再超声2h,将完全溶解的溶液,在220℃的温度下保持5h,即得高熵催化剂溶液,向高熵催化剂溶液加入环己烷和乙醇混合液,离心洗涤3次后,在60℃真空干燥箱中干燥过夜,烘干后研磨即得高熵催化剂;所使用乙酰丙酮金属络合物为乙酰丙酮铁、乙酰丙酮锰、乙酰丙酮钴、乙酰丙酮镍、乙酰丙酮铂或乙酰丙酮铝中的五种或五种以上,其中以上乙酰丙酮金属络合物均可用金属铜、铬、钒、镧、铈的乙酰丙酮络合物替换。
4.一种如权利要求3所述的固体高熵催化剂的应用方法,其特征在于,应用于生物质基糠醛与脂肪醇选择性氧化-缩合制呋喃丙烯醛的反应,其步骤是:将生物质基糠醛作为反应底物,使用醇作溶剂,加入固体高熵催化剂,添加入碱助剂,加热并搅拌,糠醛与脂肪醇发生催化串联反应,该方法以氧气为氧化剂进行。
5.根据权利要求3所述的固体高熵催化剂的应用方法,其特征在于,所述的脂肪醇为乙醇、丙醇、异丙醇、丁醇、异丁醇、正戊醇、正己醇、正庚醇、正辛醇或异辛醇中的一种或几种。
6.根据权利要求3所述的固体高熵催化剂的应用方法,其特征在于:所述的碱助剂为Li2CO3、Na2CO3、K2CO3、Cs2CO3、KHCO3、NaHCO3、LiOH、NaOH、KOH、SrOH、Ca(OH)2、CaO、甲酸钠、乙酸钠、丙酸钠、甲醇钠或乙醇钠中的一种或几种。
7.根据权利要求3所述的固体高熵催化剂的应用方法,其特征在于:加热反应温度为0-240℃,反应时间为0-60h,搅拌速率为0-9000r/min。
8.根据权利要求3所述的固体高熵催化剂的应用方法,其特征在于:所述的催化剂和反应底物糠醛质量百分比为0.0001-50%。
9.根据权利要求3所述的固体高熵催化剂的应用方法,其特征在于:所述的反应氧化剂为氧气、空气、氧气混合气体、双氧水或者叔丁基过氧化氢中的一种。
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