CN113072529A - 一种生物基bpa衍生物的合成方法 - Google Patents
一种生物基bpa衍生物的合成方法 Download PDFInfo
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- CN113072529A CN113072529A CN202110291766.XA CN202110291766A CN113072529A CN 113072529 A CN113072529 A CN 113072529A CN 202110291766 A CN202110291766 A CN 202110291766A CN 113072529 A CN113072529 A CN 113072529A
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- 239000003054 catalyst Substances 0.000 claims abstract description 27
- 239000002904 solvent Substances 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 20
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 14
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- 238000001816 cooling Methods 0.000 claims abstract description 12
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- 229930195725 Mannitol Natural products 0.000 claims description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 3
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 3
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- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 claims description 3
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/20—Free hydroxyl or mercaptan
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D321/00—Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
- C07D321/02—Seven-membered rings
- C07D321/04—Seven-membered rings not condensed with other rings
- C07D321/08—1,4-Dioxepines; Hydrogenated 1,4-dioxepines
Abstract
本发明提供了一种生物基BPA衍生物的合成方法,具体步骤包括将生物质衍生醇、羰基化合物和催化剂置于溶剂中混合均匀后密封、对密封混合物搅拌加热至40~100℃反应8~24h,然后自然冷却至室温,取出产物,其中,酸催化剂的用量为羰基化合物质量的1~20%,生物羰基化合物与生物质衍生醇的摩尔比为1:1~1:3,本发明利用简单的生物质衍生醇与羰基化合物在催化条件下脱水缩合生成环缩醛产物,反应成本低,可转化为高附加值的生物基BPA衍生物,具有较高的实际应用价值。
Description
技术领域
本发明涉及化工材料技术领域,特别是一种生物基BPA衍生物的合成方法。
背景技术
双酚A,也称BPA,在工业上被用来合成聚碳酸酯(PC)和环氧树脂等材料。60年代以来就被用于制造塑料瓶、幼儿用的吸口杯、食品和饮料罐内侧涂层。从矿泉水瓶、医疗器械到食品包装的内里,BPA无处不在。每年,全世界约生产2700万吨含有BPA的塑料。但BPA会导致内分泌失调,威胁着胎儿和儿童的健康,甚至可能会导致癌症和肥胖。现全世界已禁止生产含化学物质双酚A(BPA)的婴儿奶瓶。
因此,如何提供一种生物基BPA衍生物的合成方法以取代BPA合成材料是本领域技术人员亟待解决的问题。
发明内容
本发明的目的在于克服现有技术的不足,提供一种生物基BPA衍生物的合成方法,以解决上述技术背景中所提出的问题。
本发明的目的是通过以下技术方案来实现的:
一种生物基BPA衍生物的合成方法,具体包括以下步骤:
S1、将生物质衍生醇、羰基化合物和催化剂置于溶剂中混合均匀后密封;
S2、对密封混合物搅拌加热至40~100℃反应8~24h,然后自然冷却至室温,取出产物;
其中,所述酸催化剂的用量为羰基化合物质量的1~20%,羰基化合物与生物质衍生醇的摩尔比为1:1~1:3。
进一步的,所述生物质衍生醇为乙醇、乙二醇、正丙醇、异丙醇、1,3-丙二醇、1,2-丙二醇、丙三醇、正丁醇、1,2-丁二醇、1,3-丁二醇、1,4-丁二醇、异丁醇、正戊醇、1,2-戊二醇、1,3-戊二醇、1,4-戊二醇、2,4-戊二醇、异戊醇、正己醇、1,2-己二醇或1,3-己二醇和、异戊醇、木糖醇、甘露醇以及山梨醇中的一种。
进一步的,所述羰基化合物为果糖、丙酮、1,3-二羟基丙酮、木酮糖、赤藓酮糖、葡萄糖、木糖、阿拉伯糖、半乳糖、甘露糖、甘油醛、肉桂醛、香草醛、紫苏醛、铃兰醛、月桂醛、乙酰丙酸、乳酸、柠檬酸、苹果酸、酒石酸、草酸、琥珀酸、乳酸以及醋酸中的一种。
进一步的,其特征在于,所述催化剂为HCL、H2SO4、H3PO4、M K10、PTSA、MCM-41、ZSM-5、HY、HUSY、TUD、Si-1、MFI、MCF、SEA、BEA、KIT、AC、HTNT、HPW、HPM、ZrO2、ZrP、SnF2、SnCl2、Amberlyst中的一种。
进一步的,所述溶剂为三氟甲苯、乙腈、甲醇、丁醇、异丙醇、氯仿、丙酮、环氧乙烷以及四氯化碳中的一种。
本发明的有益效果是:
与现有技术相比,本发明提供的一种生物基BPA衍生物的合成方法,利用简单的生物质衍生醇与羰基化合物在催化条件下脱水缩合生成环缩醛产物,反应成本低,可转化为高附加值的生物基BPA衍生物,具有较高的实际应用价值。
具体实施方式
以下通过特定的具体实例说明本发明的实施方式,本领域技术人员可由本说明书所揭露的内容轻易地了解本发明的其他优点与功效。本发明还可以通过另外不同的具体实施方式加以实施或应用,本说明书中的各项细节也可以基于不同观点与应用,在没有背离本发明的精神下进行各种修饰或改变。需说明的是,在不冲突的情况下,以下实施例及实施例中的特征可以相互组合。
实施例1:
一种生物基BPA衍生物的合成方法,具体包括以下步骤:
S1、将生物质衍生醇、羰基化合物和催化剂置于溶剂中混合均匀后密封;
S2、对密封混合物搅拌加热至40~100℃反应8~24h,然后自然冷却至室温,取出产物;
其中,所述酸催化剂的用量为羰基化合物质量的1~20%,羰基化合物与生物质衍生醇的摩尔比为1:1~1:3。
优选的,所述生物质衍生醇为乙醇、乙二醇、正丙醇、异丙醇、1,3-丙二醇、1,2-丙二醇、丙三醇、正丁醇、1,2-丁二醇、1,3-丁二醇、1,4-丁二醇、异丁醇、正戊醇、1,2-戊二醇、1,3-戊二醇、1,4-戊二醇、2,4-戊二醇、异戊醇、正己醇、1,2-己二醇或1,3-己二醇和、异戊醇、木糖醇、甘露醇以及山梨醇中的一种。
优选的,所述羰基化合物为果糖、丙酮、1,3-二羟基丙酮、木酮糖、赤藓酮糖、葡萄糖、木糖、阿拉伯糖、半乳糖、甘露糖、甘油醛、肉桂醛、香草醛、紫苏醛、铃兰醛、月桂醛、乙酰丙酸、乳酸、柠檬酸、苹果酸、酒石酸、草酸、琥珀酸、乳酸以及醋酸中的一种。
优选的,其特征在于,所述催化剂为HCL、H2SO4、H3PO4、M K10、PTSA、MCM-41、ZSM-5、HY、HUSY、TUD、Si-1、MFI、MCF、SEA、BEA、KIT、AC、HTNT、HPW、HPM、ZrO2、ZrP、SnF2、SnCl2、Amberlyst中的一种。
优选的,所述溶剂为三氟甲苯、乙腈、甲醇、丁醇、异丙醇、氯仿、丙酮、环氧乙烷以及四氯化碳中的一种。
实施例2:
一种生物基BPA衍生物的合成方法,具体包括以下步骤:
S1、将生物质衍生醇、羰基化合物和催化剂置于溶剂中混合均匀后密封;
S2、对密封混合物搅拌加热至60℃反应12h,然后自然冷却至室温,取出产物;
酸催化剂的用量为羰基化合物质量的1~20%,羰基化合物与生物质衍生醇的摩尔比为1:1~1:3,其中,生物质衍生醇为山梨醇,羰基化合物为丙酮,溶剂为三氟甲苯。
催化剂为HCL、H2SO4、H3PO4、M K10、PTSA、MCM-41、ZSM-5、HY、HUSY、TUD、Si-1、MFI、MCF、SEA、BEA、KIT、AC、HTNT、HPW、HPM、ZrO2、ZrP、SnF2、SnCl2、Amberlyst中的一种。
催化剂对丙三醇与丙酮反应的影响如下表格所示:
实施例3:
一种生物基BPA衍生物的合成方法,具体包括以下步骤:
S1、将生物质衍生醇、羰基化合物和催化剂置于溶剂中混合均匀后密封;
S2、对密封混合物搅拌加热至60℃反应12h,然后自然冷却至室温,取出产物;
酸催化剂的用量为羰基化合物质量的1~20%,羰基化合物与生物质衍生醇的摩尔比为1:1~1:3,其中,生物质衍生醇为丙三醇,羰基化合物为乙酰丙酸,溶剂为三氟甲苯。
催化剂为HCL、H2SO4、H3PO4、M K10、PTSA、MCM-41、ZSM-5、HY、HUSY、TUD、Si-1、MFI、MCF、SEA、BEA、KIT、AC、HTNT、HPW、HPM、ZrO2、ZrP、SnF2、SnCl2、Amberlyst中的一种。
催化剂对丙三醇与丙酮反应的影响如下表格所示:
实施例4:
一种生物基BPA衍生物的合成方法,具体包括以下步骤:
S1、将生物质衍生醇、羰基化合物和催化剂置于溶剂中混合均匀后密封;
S2、对密封混合物搅拌加热至60℃反应12h,然后自然冷却至室温,取出产物;
酸催化剂的用量为羰基化合物质量的1~20%,羰基化合物与生物质衍生醇的摩尔比为1:1~1:3,其中,生物质衍生醇为乙二醇,羰基化合物为甘油醛,溶剂为三氟甲苯。
催化剂为HCL、H2SO4、H3PO4、M K10、PTSA、MCM-41、ZSM-5、HY、HUSY、TUD、Si-1、MFI、MCF、SEA、BEA、KIT、AC、HTNT、HPW、HPM、ZrO2、ZrP、SnF2、SnCl2、Amberlyst中的一种。
催化剂对乙二醇与甘油醛反应的影响如下表格所示:
实施例5:
一种生物基BPA衍生物的合成方法,具体包括以下步骤:
S1、将生物质衍生醇、羰基化合物和催化剂置于溶剂中混合均匀后密封;
S2、对密封混合物搅拌加热至60℃反应12h,然后自然冷却至室温,取出产物;
酸催化剂的用量为羰基化合物质量的1~20%,羰基化合物与生物质衍生醇的摩尔比为1:1~1:3,其中,生物质衍生醇为1,3-丙二醇,羰基化合物为丙酮,溶剂为三氟甲苯。
催化剂为HCL、H2SO4、H3PO4、M K10、PTSA、MCM-41、ZSM-5、HY、HUSY、TUD、Si-1、MFI、MCF、SEA、BEA、KIT、AC、HTNT、HPW、HPM、ZrO2、ZrP、SnF2、SnCl2、Amberlyst中的一种。
催化剂对丙二醇与丙酮反应的影响如下表格所示:
实施例6:
一种生物基BPA衍生物的合成方法,具体包括以下步骤:
S1、将生物质衍生醇、羰基化合物和催化剂置于溶剂中混合均匀后密封;
S2、对密封混合物搅拌加热至60℃反应12h,然后自然冷却至室温,取出产物;
酸催化剂的用量为羰基化合物质量的5~20%,羰基化合物与生物质衍生醇的摩尔比为1:3,其中,生物质衍生醇为山梨醇,羰基化合物为乙酰丙酸,催化剂为MCM-41,溶剂为三氟甲苯。
MCM-41用量对反应的影响如下表格所示:
实施例7:
一种生物基BPA衍生物的合成方法,具体包括以下步骤:
S1、将生物质衍生醇、羰基化合物和催化剂置于溶剂中混合均匀后密封;
S2、对密封混合物搅拌加热至40~100℃反应12h,然后自然冷却至室温,取出产物;
酸催化剂的用量为羰基化合物质量的15%,羰基化合物与生物质衍生醇的摩尔比为1:3,其中,生物质衍生醇为乙二醇,羰基化合物为甘油醛,催化剂为ZrO2,溶剂为三氟甲苯。
反应温度对反应的影响如下表格所示:
实施例8:
一种生物基BPA衍生物的合成方法,具体包括以下步骤:
S1、将生物质衍生醇、羰基化合物和催化剂置于溶剂中混合均匀后密封;
S2、对密封混合物搅拌加热至60℃反应8~24h,然后自然冷却至室温,取出产物;
酸催化剂的用量为羰基化合物质量的15%,羰基化合物与生物质衍生醇的摩尔比为1:3,其中,生物质衍生醇为丙三醇,羰基化合物为丙酮,催化剂为ZrO2,溶剂为三氟甲苯。
反应时间对反应的影响如下表格所示:
实施例9:
一种生物基BPA衍生物的合成方法,具体包括以下步骤:
S1、将生物质衍生醇、羰基化合物和催化剂置于溶剂中混合均匀后密封;
S2、对密封混合物搅拌加热至60℃反应12h,然后自然冷却至室温,取出产物;
酸催化剂的用量为羰基化合物质量的20%,羰基化合物与生物质衍生醇的摩尔比为1:3,其中,生物质衍生醇为丙三醇,羰基化合物为柠檬酸,催化剂为HPW。
溶剂为三氟甲苯、乙腈、甲醇、丁醇、异丙醇、氯仿、丙酮、环氧乙烷以及四氯化碳中的一种。
溶剂种类对反应的影响如下表格所示:
以上所述实施例仅表达了本发明的具体实施方式,其描述较为具体和详细,但并不能因此而理解为对本发明专利范围的限制。应当指出的是,对于本领域的普通技术人员来说,在不脱离本发明构思的前提下,还可以做出若干变形和改进,这些都属于本发明的保护范围。
Claims (5)
1.一种生物基BPA衍生物的合成方法,其特征在于,包括以下步骤:
S1、将生物质衍生醇、羰基化合物和催化剂置于溶剂中混合均匀后密封;
S2、对密封混合物搅拌加热至40~100℃反应8~24h,然后自然冷却至室温,取出产物;其中,所述酸催化剂的用量为羰基化合物质量的1-20%,羰基化合物与生物质衍生醇的摩尔比为1:1~1:3。
2.根据权利要求1所述的一种一种生物基BPA衍生物的合成方法,其特征在于,所述生物质衍生醇为乙醇、乙二醇、正丙醇、异丙醇、1,3-丙二醇、1,2-丙二醇、丙三醇、正丁醇、1,2-丁二醇、1,3-丁二醇、1,4-丁二醇、异丁醇、正戊醇、1,2-戊二醇、1,3-戊二醇、1,4-戊二醇、2,4-戊二醇、异戊醇、正己醇、1,2-己二醇或1,3-己二醇和、异戊醇、木糖醇、甘露醇以及山梨醇中的一种。
3.根据权利要求1所述的一种生物基BPA衍生物的合成方法,其特征在于,所述羰基化合物为果糖、丙酮、1,3-二羟基丙酮、木酮糖、赤藓酮糖、葡萄糖、木糖、阿拉伯糖、半乳糖、甘露糖、甘油醛、肉桂醛、香草醛、紫苏醛、铃兰醛、月桂醛、乙酰丙酸、乳酸、柠檬酸、苹果酸、酒石酸、草酸、琥珀酸、乳酸以及醋酸中的一种。
4.根据权利要求1所述的一种生物基BPA衍生物的合成方法,其特征在于,其特征在于,所述催化剂为HCL、H2SO4、H3PO4、M K10、PTSA、MCM-41、ZSM-5、HY、HUSY、TUD、Si-1、MFI、MCF、SEA、BEA、KIT、AC、HTNT、HPW、HPM、ZrO2、ZrP、SnF2、SnCl2、Amberlyst中的一种。
5.根据权利要求1所述的一种生物基BPA衍生物的合成方法,其特征在于,所述溶剂为三氟甲苯、乙腈、甲醇、丁醇、异丙醇、氯仿、丙酮、环氧乙烷以及四氯化碳中的一种。
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