CN113429345B - 一种吖啶酮的制备方法 - Google Patents
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- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 title claims abstract description 48
- GDALETGZDYOOGB-UHFFFAOYSA-N Acridone Natural products C1=C(O)C=C2N(C)C3=CC=CC=C3C(=O)C2=C1O GDALETGZDYOOGB-UHFFFAOYSA-N 0.000 title claims abstract description 47
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 239000011831 acidic ionic liquid Substances 0.000 claims abstract description 12
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 6
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- ZWJINEZUASEZBH-UHFFFAOYSA-N fenamic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=CC=C1 ZWJINEZUASEZBH-UHFFFAOYSA-N 0.000 claims description 11
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- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 238000004321 preservation Methods 0.000 claims description 2
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 12
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 4
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- 239000001257 hydrogen Substances 0.000 description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 14
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- BATAOFZEDHPRTM-UHFFFAOYSA-N 9-oxo-10h-acridine-4-carboxylic acid Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C(C(=O)O)=CC=C2 BATAOFZEDHPRTM-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C07D219/06—Oxygen atoms
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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
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
- B01J31/0281—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member
- B01J31/0284—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member of an aromatic ring, e.g. pyridinium
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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
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
- B01J31/0285—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre also containing elements or functional groups covered by B01J31/0201 - B01J31/0274
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明属于有机合成技术领域,具体涉及一种吖啶酮的制备方法,本发明的制备方法中,以酸性离子液体同时作为催化剂和溶剂,其中酸性离子液体以其可回收的优点作为催化剂替代硫酸、对甲苯磺酸等能够解决三废较多的问题;同时以其挥发性小的优点替代甲苯等挥发性有机溶剂,能够解决日益迫切的VOCs防治问题。该方法环境友好,符合绿色化学的要求。
Description
技术领域
本发明属于有机合成技术领域,具体涉及一种吖啶酮的制备方法。
背景技术
吖啶酮(式1)是吖啶氧化后的产物,具有高度平面的刚性分子结构,共轭骨架中的官能团主要是9、10位上易于功能化的羰基和仲胺基,分子间存在显著的氢键和π-π相互作用,研究表明,吖啶酮类药物具有良好的抗肿瘤活性。另一方面,近年来由于小分子荧光探针的迅速发展,以及吖啶酮本身的刚性结构和良好的光学性质,吖啶酮衍生物在生物荧光探针、有机光电器件、荧光传感器等领域的应用引起了人们广泛的关注。
式1
吖啶酮文献制备方法或步骤繁琐或所用溶剂存在环境污染隐患,限制了其在应用领域的研究,因此,环境友好、操作简便且高效的制备吖啶酮的工艺亟待开发。
尽管吖啶酮具有很高的应用价值,但现有文献合成方法大多用H3PO4、H2SO4、对甲苯磺酸等作催化剂,甲苯等作为有机溶剂,这类催化剂的大规模使用带来环境、资源等问题,为响应环保要求和VOCs要求,寻找新型催化剂和溶剂,实现4-羧基吖啶酮的绿色合成具有一定的应用价值和现实意义。
为解决现有的制备方法中产生的环境污染和操作复杂的问题,本发明在此基础上进一步研究,得到环境友好的吖啶酮的制备方法。
发明内容
本发明的目的在于提供一种吖啶酮的制备方法,以解决现有的制备方法中采用H2SO4、对甲苯磺酸等作催化剂,甲苯等最为有机溶剂产生的环境污染或操作复杂的问题。
5、本发明是通过以下技术方案实现的:一种吖啶酮的制备方法,包括以下步骤:
S1:将N-苯基邻氨基苯甲酸和酸性离子液添加至反应容器中;
S2:对步骤S1中的混合物加热至40-65℃,并搅拌均匀;
S3:保温状态下进行反应2-4小时,降温至室温得到粗品;
S4:将步骤S3中的粗品进行纯化。
进一步地,步骤S1中的酸性离子液为1-(丁基-4-磺酸基)-3-甲基咪唑三氟甲磺酸盐([HSO3-bmim]CF3SO3)、1-(丁基-4-磺酸基)-3-甲基咪唑对甲苯磺酸盐([HSO3-bmim]P-TSA)、1-(丁基-4-磺酸基)-3-甲基咪唑硫酸氢盐([HSO3-bmim]HSO4)、1-(丁基-4-磺酸基)-3-甲基咪唑磷酸二氢盐([HSO3-bmim]H2PO4)、1-丁基磺酸-3-甲基咪唑对甲苯磺酸盐([(CH2)4SO3HMIm]TS)中的一种。
进一步地,所述N-苯基邻氨基苯甲酸和酸性离子液的质量比例为1∶(3-10)。
进一步地,步骤S4中纯化步骤为使用粗品2-4倍质量的水洗涤并烘干。
本发明的有益效果在于:1、本发明的制备方法中,以酸性离子液体同时作为催化剂和溶剂,其中酸性离子液体以其可回收的优点作为催化剂替代硫酸、对甲苯磺酸等能够解决三废较多的问题;同时以其挥发性小的优点替代甲苯等挥发性有机溶剂,能够解决日益迫切的VOCs防治问题。该方法环境友好,符合绿色化学的要求。
2、本制备方法中,通过催化剂的加入降低了反应活化能,提高了反应活性,在45-60℃下即可反应,较以往的100℃以上避免了反应剧烈进行,反应更温和、过程可控性好,操作更安全简便且制得的吖啶酮的收率和纯度较高,收率为94%以上,纯度为99%以上,且反应完成后降至室温过滤后处理简便具有较好的工业化应用价值。
附图说明
图1为本发明的实施例1制得的吖啶酮的核磁共振氢谱图。
图2为本发明的实施例2制得的吖啶酮的核磁共振氢谱图。
图3为本发明的实施例3制得的吖啶酮的核磁共振氢谱图。
图4为本发明的实施例4制得的吖啶酮的核磁共振氢谱图。
图5为本发明的实施例5制得的吖啶酮的核磁共振氢谱图。
图6为本发明的实施例6制得的吖啶酮的核磁共振氢谱图。
图7为本发明的实施例7制得的吖啶酮的核磁共振氢谱图。
具体实施方式
实施例1
室温下将(21.3g)N-苯基邻氨基苯甲酸和(213.0g)[HSO3-bmim]CF3SO3搅拌下加入反应器中,升温至45℃,保温搅拌反应4h,降至室温过滤所得固体即为吖啶酮粗品,然后在粗品中加入40g水洗涤,过滤,所得滤液回收,所得滤饼90℃烘干得到黄色固体粉末吖啶酮(18.6g,纯度99.1%,收率94.3%)。
对于实施例1制得的吖啶酮进行核磁共振氢谱测试,测试结果如图1所示。
实施例2
室温下将(21.3g)N-苯基邻氨基苯甲酸和(106.5g)[HSO3-bmim]CF3SO3搅拌下加入反应器中,升温至55℃,保温搅拌反应3h,降至室温过滤所得固体即为吖啶酮粗品,然后在粗品中加入60g水洗涤,过滤,所得滤液回收,所得滤饼90℃烘干得到黄色固体粉末吖啶酮(19.0g,纯度99.2%,收率96.4%)。
对于实施例2制得的吖啶酮进行核磁共振氢谱测试,测试结果如图2所示。
实施例3
室温下将(21.3g)N-苯基邻氨基苯甲酸和(63.9g)[HSO3-bmim]CF3SO3搅拌下加入反应器中,升温至60℃,保温搅拌反应2h,降至室温过滤所得固体即为吖啶酮粗品,然后在粗品中加入80g水洗涤,过滤,所得滤液回收,所得滤饼90℃烘干得到黄色固体粉末吖啶酮(18.8g,纯度99.2%,收率95.5%)。
对于实施例3制得的吖啶酮进行核磁共振氢谱测试,测试结果如图3所示。
实施例4
室温下将(21.3g)N-苯基邻氨基苯甲酸和(85.2g)[HSO3-bmim]P-TSA搅拌下加入反应器中,升温至50℃,保温搅拌反应4h,降至室温过滤所得固体即为吖啶酮粗品,然后在粗品中加入60g水洗涤,过滤,所得滤液回收,所得滤饼90℃烘干得到黄色固体粉末吖啶酮(19.1g,纯度99.0%,收率96.7%)。
对于实施例4制得的吖啶酮进行核磁共振氢谱测试,测试结果如图4所示。
实施例5
室温下将(21.3g)N-苯基邻氨基苯甲酸和(95.8g)[HSO3-bmim]HSO4搅拌下加入反应器中,升温至50℃,保温搅拌反应4h,降至室温过滤所得固体即为吖啶酮粗品,然后在粗品中加入60g水洗涤,过滤,所得滤液回收,所得滤饼90℃烘干得到黄色固体粉末吖啶酮(18.8g,纯度99.3%,收率95.9%)。
对于实施例5制得的吖啶酮进行核磁共振氢谱测试,测试结果如图5所示。
实施例6
室温下将(21.3g)N-苯基邻氨基苯甲酸和(74.6g)[HSO3-bmim]H2PO4搅拌下加入反应器中,升温至55℃,保温搅拌反应4h,降至室温过滤所得固体即为吖啶酮粗品,然后在粗品中加入60g水洗涤,过滤,所得滤液回收,所得滤饼90℃烘干得到黄色固体粉末吖啶酮(18.4g,纯度99.5%,收率94%)。
对于实施例6制得的吖啶酮进行核磁共振氢谱测试,测试结果如图6所示。
实施例7
室温下将(21.3g)N-苯基邻氨基苯甲酸和(63.9g)[(CH2)4SO3HMIm]TS搅拌下加入反应器中,升温至45℃,保温搅拌反应3h,降至室温过滤所得固体即为吖啶酮粗品,然后在粗品中加入60g水洗涤,过滤,所得滤液回收,所得滤饼90℃烘干得到黄色固体粉末吖啶酮(18.5g,纯度99.0%,收率94%)。
对于实施例7制得的吖啶酮进行核磁共振氢谱测试,测试结果如图7所示。
核磁图谱是定性分析,同一种化合物的核磁图谱相同,故补充了相应实施例的纯度检测图谱和检测方法;
总的检测方法:采用高效液相色谱法进行含量检测,主峰位置与标准品出峰时间一致,紫外检测器,流速0.8ml/min,甲醇及磷酸水混合溶液做流动相。
最后应说明的是:以上所述仅为本发明的优选实施例而已,并不用于限制本发明,尽管参照前述实施例对本发明进行了详细的说明,对于本领域的技术人员来说,其依然可以对前述各实施例所记载的技术方案进行修改,或者对其中部分技术特征进行等同替换,凡在本发明的精神和原则之内,所作的任何修改、等同替换、改进等,均应包含在本发明的保护范围之内。
Claims (2)
1.一种吖啶酮的制备方法,其特征在于:包括以下步骤:
S1:将N-苯基邻氨基苯甲酸和酸性离子液添加至反应容器中;
S2:对步骤S1中的混合物加热至40-65℃,并搅拌均匀;
S3:保温状态下进行反应2-4小时,降温至室温得到粗品;
S4:将步骤S3中的粗品进行纯化;
其中,所述N-苯基邻氨基苯甲酸和酸性离子液的质量比例为1∶(3-10);
在步骤S1中,所述酸性离子液为1-(丁基-4-磺酸基)-3-甲基咪唑三氟甲磺酸盐([HSO3-bmim]CF3SO3)、1-(丁基-4-磺酸基)-3-甲基咪唑对甲苯磺酸盐([HSO3-bmim]P-TSA)、1-(丁基-4-磺酸基)-3-甲基咪唑硫酸氢盐([HSO3-bmim]HSO4)、1-(丁基-4-磺酸基)-3-甲基咪唑磷酸二氢盐([HSO3-bmim]H2PO4)、1-丁基磺酸-3-甲基咪唑对甲苯磺酸盐([(CH2)4SO3HMIm]TS)中的一种。
2.根据权利要求1所述的一种吖啶酮的制备方法,其特征在于:步骤S4中纯化步骤为使用粗品2-4倍质量的水洗涤并烘干。
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