CN115260008A - 一种铌基材料催化芳香醚类物质水解制备酚类的方法 - Google Patents
一种铌基材料催化芳香醚类物质水解制备酚类的方法 Download PDFInfo
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- 238000000034 method Methods 0.000 title claims abstract description 18
- 229910052758 niobium Inorganic materials 0.000 title claims abstract description 14
- 239000010955 niobium Substances 0.000 title claims abstract description 14
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 239000000126 substance Substances 0.000 title claims abstract description 14
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- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910000484 niobium oxide Inorganic materials 0.000 claims description 13
- URLJKFSTXLNXLG-UHFFFAOYSA-N niobium(5+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Nb+5].[Nb+5] URLJKFSTXLNXLG-UHFFFAOYSA-N 0.000 claims description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- CNHRNMLCYGFITG-UHFFFAOYSA-A niobium(5+);pentaphosphate Chemical compound [Nb+5].[Nb+5].[Nb+5].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O CNHRNMLCYGFITG-UHFFFAOYSA-A 0.000 claims description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- CFJRGWXELQQLSA-UHFFFAOYSA-N azanylidyneniobium Chemical compound [Nb]#N CFJRGWXELQQLSA-UHFFFAOYSA-N 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- UNASZPQZIFZUSI-UHFFFAOYSA-N methylidyneniobium Chemical compound [Nb]#C UNASZPQZIFZUSI-UHFFFAOYSA-N 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- KMZHZAAOEWVPSE-UHFFFAOYSA-N glycerol monoacetate Natural products CC(=O)OCC(O)CO KMZHZAAOEWVPSE-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 238000009776 industrial production Methods 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- PXIKRTCSSLJURC-UHFFFAOYSA-N Dihydroeugenol Chemical compound CCCC1=CC=C(O)C(OC)=C1 PXIKRTCSSLJURC-UHFFFAOYSA-N 0.000 description 8
- SCTPZNJTGOGSQD-UHFFFAOYSA-N 4-propylbenzene-1,2-diol Chemical compound CCCC1=CC=C(O)C(O)=C1 SCTPZNJTGOGSQD-UHFFFAOYSA-N 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
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- 125000001424 substituent group Chemical group 0.000 description 3
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 238000007172 homogeneous catalysis Methods 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
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- 239000011973 solid acid Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 2
- UYXMBPVOGLUKIV-UHFFFAOYSA-N (2-methoxyphenyl) propanoate Chemical compound CCC(=O)OC1=CC=CC=C1OC UYXMBPVOGLUKIV-UHFFFAOYSA-N 0.000 description 1
- WSJRZXWNCYLHIX-UHFFFAOYSA-N 2-methoxy-4-propylphenol 2-methoxy-5-propylphenol Chemical compound CCCC1=CC=C(OC)C(O)=C1.CCCC1=CC=C(O)C(OC)=C1 WSJRZXWNCYLHIX-UHFFFAOYSA-N 0.000 description 1
- 229910015845 BBr3 Inorganic materials 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
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- BLQJIBCZHWBKSL-UHFFFAOYSA-L magnesium iodide Chemical compound [Mg+2].[I-].[I-] BLQJIBCZHWBKSL-UHFFFAOYSA-L 0.000 description 1
- 229910001641 magnesium iodide Inorganic materials 0.000 description 1
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
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- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/20—Vanadium, niobium or tantalum
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- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
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- B01J27/14—Phosphorus; Compounds thereof
- B01J27/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J27/195—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with vanadium, niobium or tantalum
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
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Abstract
本发明提供了一种铌基材料催化芳香醚类物质水解制备酚类的方法。以铌基材料为催化剂,在一定的反应条件下,芳香醚类反应物可直接水解制备酚类物质。此方法制备的酚类产物选择性高、收率高,催化剂易回收且可循环使用,反应过程环境友好,操作简单,适于工业化生产。
Description
技术领域
本发明涉及一种采用铌基材料催化芳香醚类物质水解制备酚类的方法。
背景技术
芳香醚可由可再生资源——木质生物质得到,如果使用芳香醚作为原料直接水解得到酚类物质,不仅原料易得、成本较低,而且具有可持续性、绿色环保。通过芳香醚制备的酚类物质可作为杀虫剂、树脂材料、农药和药物等化学品的前驱体,应用前景广泛。
在早期的研究中,人们使用均相催化剂来催化芳香醚的水解,如亲核试剂LiBr、NaCN和Et2N(CH2)2SH·HCl等,Brønsted酸催化剂HBr、HCl和H2SO4等,Lewis酸催化剂BBr3、三甲基碘硅烷(TMSI)和MgI2等(文献[1] Jeroen Bomon et al, Green Chem1995-2009 (2021))。虽然芳香醚的均相催化能取得较好的结果,但是具有一定酸碱性的催化剂会对设备造成腐蚀,产物分离和处理复杂,催化剂的活性位点难以调节且难以回收利用。
近年来,对芳香醚非均相水解反应催化剂的研究有了新的进展,这些催化剂包括:三氟甲磺酸盐(文献[2] Le Yang et al,Journal of Molecular Catalysis A: Chemical368-369 (2013))、杂多酸(文献[3] CN112742475A)和酸性氧化物(文献[4] Xian Wu etal, ChemSusChem, e202102248 (2022))等。
虽然非均相催化解决了均相催化中催化剂不易分离的问题,但是目前采用的固体酸催化剂依然存在稳定性差或制备过程复杂等问题。
因此本领域亟需一种水热稳定性高并且制备过程简单的固体酸催化剂。
发明内容
有鉴于此,本发明的目的在于提供一种采用铌基材料催化芳香醚类物质水解制备酚类的方法。
为此,本发明提供了一种通过芳香醚类物质水解制备酚类物质的方法,所述方法包括:
将芳香醚和水以及铌基催化剂按比例投入至反应器中,在一定条件下进行反应,反应后的混合物进行萃取分离,得到酚类产物。
其中,所述催化剂为铌基催化剂中的一种或两种;所述铌基催化材料为无定形的氧化铌、磷酸铌、氮化铌、碳化铌或掺杂的氧化铌中的一种或两种;所述掺杂的氧化铌为掺杂P、S、N元素中的一种或两种;
所述反应条件为:反应温度200 oC~320 oC,反应压力为3~6 MPa;
所述芳香醚的分子结构通式为Ar-O-R,式中R为烷基;Ar为芳香基,芳香基的邻位、间位或对位可接取代基;
所述萃取剂为乙醇、甘油或乙酸乙酯中的一种;
本发明提供了一种全新的制备酚类物质的方法,可以作为工业化制备有机中间体、医药中间体和环氧树脂等材料的重要环节。
本发明的优势在于:
(1)酚类产物选择性好、收率高;
(2)催化剂水热稳定性好。
具体实施方式
在本发明方法中,使原料、水和催化剂在反应器中搅拌,在一定条件下发生反应,反应后的混合液进行萃取,得到目标产物并将催化剂分离。
优选的,在本发明中,反应条件为:反应温度250 oC ~280 oC,反应压力为3~4MPa。
优选的,在本发明中,所述催化剂为无定形的氧化铌、磷酸铌、氮化铌、碳化铌或掺杂的氧化铌中的一种或两种。
优选的,在本发明中,芳香醚上的取代基选择邻位,取代基选择羟基和氨基中的一种或两种。
优选的,在本发明中,萃取剂选择乙酸乙酯。
实施例
为使本发明的目的、技术方案和优点更加清楚明白,以下结合具体实施例,对本发明进一步详细说明。
实施例1-6
不同铌基催化剂在2-甲氧基-4-丙基苯酚(4-丙基愈创木酚)水解制备4-丙基邻苯二酚反应中的性能评价。评价条件:0.2 g 氧化铌催化剂,1 g 4-丙基愈创木酚,10 ml超纯水,4 MPa氮压,280 oC,分析结果见表1(其中转化率为4-丙基愈创木酚转化率,收率为4-丙基邻苯二酚收率)。
实施例7-10
以磷酸铌为催化剂,在不同温度和氮气压力下4-丙基愈创木酚水解制备4-丙基邻苯二酚反应的性能评价。评价条件:0.2 g 磷酸铌,1 g 丙基愈创木酚,10 ml超纯水,4 MPa氮压,280 oC,分析结果见表2(其中转化率为4-丙基愈创木酚转化率,收率为4-丙基邻苯二酚收率)。
实施例11-17
以氧化铌为催化剂,对不同芳香醚水解的性能评价。评价条件:0.2 g 氧化铌,1 g反应底物,10 ml超纯水,4 MPa氮压,280 oC,分析结果见表3(其中转化率为芳香醚的转化率,收率为酚类产物的收率)。
实施例18-24
以磷掺杂的氧化铌为催化剂,对不同芳香醚水解的性能评价。评价条件:0.2 g 磷掺杂的氧化铌,1 g 反应底物,10 ml超纯水,4 MPa氮压,280 oC,分析结果见表4(其中转化率为芳香醚的转化率,收率为酚类产物的收率)。
所属领域的普通技术人员应当理解:以上任何实施例的讨论仅为示例性的,并非旨在暗示本公开的范围(包括权利要求)被限于这些例子;在本发明的思路下,以上实施例或者不同实施例中的技术特征之间也可以进行组合,步骤可以以任意顺序实现,并存在如上所述的本发明的不同方面的许多其它变化,为了简明它们没有在细节中提供。
尽管已经结合了本发明的具体实施例对本发明进行了描述,但是根据前面的描述,这些实施例的很多替换、修改和变型对本领域普通技术人员来说将是显而易见的。
本发明的实施例旨在涵盖落入所附权利要求的宽泛范围之内的所有这样的替换、修改和变型。因此,凡在本发明的精神和原则之内,所做的任何省略、修改、等同替换、改进等,均应包含在本发明的保护范围之内。
Claims (6)
1.一种铌基材料催化芳香醚类物质水解制备酚类的方法,所述方法包括:将芳香醚和水以及铌基催化剂按比例投入反应器中,在一定温度和压力下进行反应,反应后的混合物进行萃取分离,得到酚类产物。
2.根据权力要求1所述的方法,其特征在于,所述催化剂为铌基材料中的一种或两种,其中铌基材料为无定形的氧化铌、磷酸铌、氮化铌、碳化铌或掺杂的氧化铌。
3.根据权力要求2所述的方法,其特征在于,所述掺杂的氧化铌为掺杂P、S、N元素中的一种或两种。
4.根据权力要求1所述的方法,其特征在于,芳香醚的分子结构通式为Ar-O-R,式中R为烷基;Ar为芳香基,芳香基的邻位、间位或对位可接取代基,优选邻位,取代基包括羟基、氨基、烷氧基以及卤素,优选羟基和氨基中的一种或两种。
5.根据权力要求1所述的方法,其特征在于,所述反应条件为200 oC~320 oC,优选250oC~300 oC;反应压力为3~6 MPa,优选3~4 MPa。
6.根据权力要求1所述的方法,其特征在于,所述萃取剂为乙醇、甘油或乙酸乙酯中的一种,优选乙酸乙酯。
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