CN114532446A - 一种饲料添加剂二酚羟基螯合铜的制备方法及其应用 - Google Patents

一种饲料添加剂二酚羟基螯合铜的制备方法及其应用 Download PDF

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CN114532446A
CN114532446A CN202210078636.2A CN202210078636A CN114532446A CN 114532446 A CN114532446 A CN 114532446A CN 202210078636 A CN202210078636 A CN 202210078636A CN 114532446 A CN114532446 A CN 114532446A
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copper
feed additive
diphenol
hydroxyl
chelated copper
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任伟
葛如兴
范俊兵
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Henan Institute Of Science And Technology Development Strategy
Weishi Vocational And Technical Education Center
Skarn Animal Health Products Shangqiu Co ltd
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Weishi Vocational And Technical Education Center
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Abstract

本发明公开了一种饲料添加剂二酚羟基螯合铜的制备及其应用，属于化学和饲料添加剂领域。本发明一种饲料添加剂二酚羟基螯合铜的制备主要包括：二酚羟基化合物与二价金属铜离子在乙醇‑水为溶剂、催化剂的条件下进行螯合反应，制备饲料添加剂二酚羟基螯合铜，制备工艺简单、成本低、无污染的优点。本发明制备的二酚羟基螯合铜具有抗菌、抗炎、抗氧化的功效，减少动物疾病的发生，提高养殖经济效益。

Description

一种饲料添加剂二酚羟基螯合铜的制备方法及其应用
技术领域
本发明涉及化学和饲料添加剂领域，具体涉及一种饲料添加剂二酚羟基螯合铜的制备方法及其应用。
背景技术
我国中草药资源丰富，历史悠久，有很多具有抗菌、抗炎、抗氧化等功能的中草药，也成为当前中草药研究的热点。
本发明从中草药经过严格筛选、提取出二羟基酚化合物的大黄酸、绿原酸、儿茶酚，通过化学合成技术与二金属铜离子进行螯合反应，提高二羟基酚化合物的抗菌、抗炎、抗氧化功效，减少动物疾病的发生，提高养殖经济效益。
发明内容
有鉴于此，本发明通过化学的方法，将二酚羟基化合物与二价金属铜离子进行螯合反应，制备一出饲料添加剂二酚羟基螯合铜，主要用于抗菌、抗炎、抗氧化的功效，减少动物疾病的发生，提高养殖经济效益。
本发明目的之一从中药提取物中筛选二酚羟基化合物与具有代谢调节功能的二价金属铜离子入手，设计出一种用于抗菌、抗炎、抗氧化的饲料添加剂的制备及其应用。
为达到上述目的，本发明提供如下技术方案：
一种用于抗菌、抗炎、抗氧化的饲料添加剂制备方法，二酚羟基化合物与二价金属铜离子在乙醇-水溶剂、催化剂的条件下进行螯合反应，得到饲料添加剂二酚羟基螯合铜。
优选的，所述二酚羟基化合物为大黄酸、绿原酸和儿茶酚。
优选的，所述二价金属铜离子为硫酸铜、氯化铜和硫化铜中的任一种或两种以上混合物；所述催化剂为乙硫醇、乙硫醚和乙醇钠中的任一种或两种以上混合物。
优选的，所述二酚羟基化合物、二价金属铜离子和催化剂的用量摩尔比为1：2.0～2.8：0.01～0.06。最佳的，所述二酚羟基化合物、二价金属铜离子和催化剂的用量摩尔比为1：2.1～2.6：0.02～0.04。
优选的，所述螯合反应的温度为20～50℃，所述反应的时间为30～60min。
最佳的，所述螯合反应的温度为25～45℃，所述反应的时间为35～55min。
本发明目的之二在于提供上述二酚羟基化合物在动物抗病方面的应用，从而为减少动物疾病发生，提高养殖经济效益。
为达到上述目的，本发明提供如下技术方案：
本发明还提出了所述的饲料添加剂二酚羟基螯合铜用于动物细菌性疾病中的应用。
本发明还提出了所述的饲料添加剂二酚羟基螯合铜用于动物抗炎抗氧化中的应用。
本发明有益效果在于：本发明提出了一种饲料添加剂二酚羟基螯合铜，与二酚羟基化合物、二价金属铜离子相比，其抗菌、抗炎、抗氧化的效果更佳，用于减少动物疾病发生，提高养殖经济效益。
本发明还提供了二酚羟基化合物螯合铜的制备方法，合成工艺简单、成本低、无污染等优点。
具体实施方式
结合以下具体实施例，对本发明作进一步的详细说明，本发明的保护内容不局限于以下实施例。在不背离发明构思的精神和范围下，本领域技术人员能够想到的变化和优点都被包括在本发明中，并且以所附的权利要求书为保护范围。实施本发明的过程、条件、试剂、实验方法等，除以下专门提及的内容之外，均为本领域的普遍知识和公知常识，本发明没有特别限制内容。
实施例1
将大黄酸2.84g(10.0mmoL)和硫酸铜3.39g(21.3mmoL)置500mL圆底烧瓶中，加入200mL的30％乙醇-水溶剂，升温至28℃，搅拌至完全溶解，再缓慢滴加乙硫醇0.0074g(0.12mmoL)和乙硫醚0.013g(0.14mmoL)的混合水溶液，滴加完毕，在28℃反应38min，降温至室温，滴加硫酸水溶液调pH至3.2，静止30分钟，过滤、低温干燥，即得到大黄酸螯合铜。
实施例2
将大黄酸2.84g(10.0mmoL)和硫化铜2.18g(22.9mmoL)置500mL圆底烧瓶中，加入200mL的30％乙醇-水溶剂，升温至32℃，搅拌至完全溶解，再缓慢滴加乙硫醚0.0072g(0.08mmoL)和乙醇钠0.021g(0.30mmoL)的混合水溶液，滴加完毕，在32℃反应43min，降温至室温，滴加硫酸水溶液调pH至3.6，静止30分钟，过滤、低温干燥，即得到大黄酸螯合铜。
实施例3
将绿原酸3.54g(10.0mmoL)和氯化铜3.16g(23.6mmoL)置500mL圆底烧瓶中，加入200mL的30％乙醇-水溶剂，升温至38℃，搅拌至完全溶解，再缓慢滴加乙硫醚0.025g(0.28mmoL)和乙醇钠0.0041g(0.06mmoL)的混合水溶液，滴加完毕，在38℃反应40min，降温至室温，滴加硫酸水溶液调pH至3.0，静止30分钟，过滤、低温干燥，即得到绿原酸螯合铜。
实施例4
将绿原酸3.54g(10.0mmoL)和硫酸铜1.83g(11.5mmoL)、硫化铜1.24g(13.1mmoL)置500mL圆底烧瓶中，加入200mL的30％乙醇-水溶剂，升温至40℃，搅拌至完全溶解，再缓慢滴加乙醇钠0.020g(0.29mmoL)的水溶液，滴加完毕，在40℃反应48min，降温至室温，滴加硫酸水溶液调pH至3.8，静止30分钟，过滤、低温干燥，即得到绿原酸螯合铜。
实施例5
将儿茶酚1.1g(10.0mmoL)和硫酸铜1.99g(12.5mmoL)、氯化铜1.77g(13.2mmoL)置500mL圆底烧瓶中，加入200mL的30％乙醇-水溶剂，升温至42℃，搅拌至完全溶解，再缓慢滴加乙硫醚0.022g(0.24mmoL)的水溶液，滴加完毕，在42℃反应53min，降温至室温，滴加硫酸水溶液调pH至3.1，静止30分钟，过滤、低温干燥，即得到儿茶酚螯合铜。
实施例6
将儿茶酚1.1g(10.0mmoL)和硫化铜1.24g(13.1mmoL)、氯化铜1.55g(11.6mmoL)置500mL圆底烧瓶中，加入200mL的30％乙醇-水溶剂，升温至44℃，搅拌至完全溶解，再缓慢滴加乙硫醇0.022g(0.35mmoL)的水溶液，滴加完毕，在44℃反应50min，降温至室温，滴加硫酸水溶液调pH至3.4，静止30分钟，过滤、低温干燥，即得到儿茶酚螯合铜。
参照上述方法，可以制备出本发明所表述的用于减少动物疾病饲料添加剂二酚羟基螯合铜。以下实施例中所用于减少动物疾病饲料添加剂二酚羟基螯合铜按以上方法制备得到。
实施例7用于动物细菌性疾病中的应用。
试验方法：河南某猪场的仔猪于2020年8月出现剧烈腹泻、排黄色水样稀便、迅速死亡为特征，剖检常有肠炎和败血症。经诊断为仔猪大肠杆菌病，选取病猪80头，分为3组，每组20头，空白组不给药，试验组分别给予实施例1、实施3、实例5制备的用于防治动物细菌疾的饲料添加剂，给药5天后统计试验结果，结果见表1。
试验结果：由表1的结果可见，与空白组相比，试验组均有显著疗效，试验过程中仔猪无任何毒副作用和不良反应，用药后不易产生耐药性。
表1用于防治动物细菌性疾病的效果
组别 病猪头数 治愈头数 死亡头数 治愈率(％)
空白组 20 0 12 0
实施例1 20 19 0 95.0
实施例3 20 17 0 85.0
实施例5 20 18 0 90.0
结果表明：制备一种饲料添加剂二酚羟基螯合铜在防治动物细菌性疾病有很好的效果。
实施例8用于动物抗炎、抗氧化中的应用。
试验方法：河南某蛋鸡场在于2020年11月解剖病鸡以心包积液、肝坏死、肾脏黄染出血肿大、脂肪黄染为主要特征，经诊断为内脏器官、肝脏炎症严重，选取病鸡3000只，分为4组，每组1500只，空白组不给药，试验组分别给予实施例2、实施例4、实施例6制备的二酚羟基螯合铜用于动物抗肝炎、抗氧化，给药10天后统计试验结果，结果见表2。
试验结果：由表2的结果可见，与空白组相比，试验组均有显著疗效，试验过程中鸡只无任何毒副作用和不良反应，用药后不易产生耐药性。
表2二酚羟基螯合铜用于动物抗炎、抗氧化的效果
组别 病鸡只数 治愈只数 死亡只数 治愈率(％)
空白组 1500 0 320 0
实施例2 1500 1230 12 82.0
实施例4 1500 1180 9 78.7
实施例6 1500 1246 10 83.1
结果表明：饲料添加剂二酚羟基螯合铜用于动物抗肝炎、抗氧化有很好的效果。
综上所述，以上实施例仅用以说明本发明的技术方案而非限制，尽管通过参照本发明的某些优选实施例已经对本发明进行了描述，但本领域的普通技术人员应当理解，可以在形式上和细节上对其做出各种各样的改变，而不偏离所附权利要求书所限定的本发明精神和范围。

Claims (9)

1.一种饲料添加剂二酚羟基螯合铜的制备方法，其特征在于：二酚羟基化合物与二价金属铜离子在乙醇-水为溶剂、催化剂的条件下进行螯合反应，制备得到饲料添加剂二酚羟基螯合铜。
2.权利要求1所述的饲料添加剂二酚羟基螯合铜的制备方法，其特征在于：所述二酚羟基化合物为大黄酸、绿原酸和儿茶酚。
3.权利要求1所述的饲料添加剂二酚羟基螯合铜的制备方法，其特征在于：所述二价金属铜离子为硫酸铜、氯化铜和硫化铜中的任一种或两种以上混合物；所述催化剂为乙硫醇、乙硫醚和乙醇钠中的任一种或两种以上混合物。
4.权利要求1所述的饲料添加剂二酚羟基螯合铜的制备方法，其特征在于：所述二酚羟基化合物、二价金属铜离子和催化剂摩尔比为1：2.0～2.8：0.01～0.06。
5.权利要求4所述的饲料添加剂二酚羟基螯合铜的制备方法，其特征在于：所述二酚羟基化合物、二价金属铜离子和催化剂摩尔比为1：2.1～2.6：0.02～0.04。
6.权利要求1所述的饲料添加剂二酚羟基螯合铜的制备方法，其特征在于：所述螯合反应的温度为20～50℃，所述反应的时间为30～60min。
7.权利要求6所述的饲料添加剂二酚羟基螯合铜的制备方法，其特征在于：所述螯合反应的温度为25～45℃，所述反应的时间为35～55min。
8.权利要求1所述的饲料添加剂二酚羟基螯合铜用于动物细菌性疾病中的应用。
9.权利要求1所述的饲料添加剂二酚羟基螯合铜用于动物抗炎抗氧化中的应用。
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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE8204560D0 (sv) * 1981-08-04 1982-08-03 Nitrokemia Ipartelepek Die gewichtszunahme von nutztieren fordernde futtermittel und futtermittelzusetze sowie verfahren zu ihrer herstellung
CN101703151A (zh) * 2009-06-18 2010-05-12 北京华牧伟业科技有限公司 黄酮与微量元素配合物在饲料行业的应用
US20140323745A1 (en) * 2013-04-25 2014-10-30 Shanghai Ai Qi Ecological Technology Co., Ltd. Polyphenolic selenium compound having functional group of alkali metal ion and selenium complex
CN106173194A (zh) * 2015-05-05 2016-12-07 上海邦成生物工程有限公司 一种动物饲料用生物性抗氧化剂
CN109043187A (zh) * 2018-08-09 2018-12-21 湖南百宜饲料科技有限公司 一种富含有机微量元素的饲料添加剂及其制备方法

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE8204560D0 (sv) * 1981-08-04 1982-08-03 Nitrokemia Ipartelepek Die gewichtszunahme von nutztieren fordernde futtermittel und futtermittelzusetze sowie verfahren zu ihrer herstellung
CN101703151A (zh) * 2009-06-18 2010-05-12 北京华牧伟业科技有限公司 黄酮与微量元素配合物在饲料行业的应用
US20140323745A1 (en) * 2013-04-25 2014-10-30 Shanghai Ai Qi Ecological Technology Co., Ltd. Polyphenolic selenium compound having functional group of alkali metal ion and selenium complex
CN106173194A (zh) * 2015-05-05 2016-12-07 上海邦成生物工程有限公司 一种动物饲料用生物性抗氧化剂
CN109043187A (zh) * 2018-08-09 2018-12-21 湖南百宜饲料科技有限公司 一种富含有机微量元素的饲料添加剂及其制备方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
张玉艳,沈生荣,唐德松,陈勋,许重阳: "Cu~(2+)与EGCG络合作用的研究", 浙江大学学报(农业与生命科学版), no. 03, pages 290 - 295 *

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