CN114794314B - 一种硒化油脂的制备方法 - Google Patents
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Abstract
本发明公开了一种硒化油脂的制备方法，在硒氢化钠液中，加入羟基醛酮、有机酸、油脂，其中，投料比为：硒：羟基醛酮：有机酸：油脂=1 mol:0.02～0.06 mol:0.62～0.74 mol:2～8 L；所得混合液搅拌24小时以上，后分液，上层油料水洗干燥后即得硒化油脂。本方法操作简单，产品易分离，且可以避免混入水溶性杂质，制备过程硒利用率高；硒化油脂在水中不溶，可以用于制造鱼、虾、蟹类的富硒饲料，也可应用于化妆品领域。
Description
技术领域
本发明涉及一种硒化油脂的制备方法，属于精细化学品制备领域。
背景技术
含硒化合物具有很好的生物活性。硒是人体所需的微量元素，有着抗癌、抗衰老等多个功能。在饲料中添加含硒化合物，不仅能够提高动物免疫力，还能够产出富硒农副产品，比如富硒鸡蛋，有很好的经济价值。我们课题组之前以糖类为载体，通过硒元素转移技术，成功开发出硒代葡萄糖等一系列硒化糖，可以用于饲料添加剂与肥料领域。然而，该方法有一定局限性，首先，由于糖类是水溶性的，产品硒化糖中的水溶性杂质无法去除，从而限制了该产品在更高要求的领域的应用(比如化妆品领域)。其次，产品的水溶性，导致其无法应用于水生动物的饲料添加剂。因此，开发油溶性硒化分子，有很好的应用意义。
发明内容
本发明的目的是提供一种硒化油脂的制备方法。硒化油脂有广泛的应用前景。
为解决上述技术问题,本发明提供的技术方案是：
一种硒化油脂的制备方法，硒氢化钠的水溶液中，加入羟基醛酮、有机酸、油脂，其中，投料比为：硒：羟基醛酮：有机酸：油脂＝1mol:0.02～0.06mol:0.62～0.74mol:2～8L；所得混合液搅拌24小时以上，后分液，上层油料水洗干燥后即得硒化油脂。
较佳的，利用硼氢化钠还原硒粉制备硒氢化钠。
较佳的，羟基醛酮为甘油醛、1,2-二羟基丙酮、2-羟基丙醛、3-羟基丙醛、葡萄糖、果糖、蔗糖、麦芽糖中的任意一种。其中，优选甘油醛，该分子微溶于水，在硒氢化钠水溶液中会被首先硒化，形成的硒中间体穿梭于水-油层，可以将油料硒化。其它羟基醛酮也有类似效果，但由于其水溶性过大，导致向油层穿梭不利，从而导致硒化油类效果不佳。
较佳的，硒与羟基醛酮的比例优选1mol:0.04mol，羟基醛酮的作用即硒化催化剂，需要有一定的量才能发挥作用，但过量使用，并不会产生更好的效果，反而增加合成成本，实验表明，使用上述用量的羟基醛酮效果最佳。
较佳的，有机酸为柠檬酸、草酸、醋酸、甲酸中的任意一种，其中，优选柠檬酸，有机酸的作用是酸化硒化液，产生硒化氢小分子，向有机相散逸，有利于硒化。其中，柠檬酸作为三元酸，其单位摩尔量内含酸官能团最多，效率最高，而实验也表明，使用柠檬酸做助剂，硒化效果最佳。
较佳的，硒与有机酸的比例优选1mol:0.68mol，在这个酸量下，最有利于硒化反应。
较佳的，油脂为色拉油、橄榄油、葵花籽油、花生油、棕榈油、猪油、牛油、羊油、大豆油、柠檬果皮油、葡萄籽油、野大豆油、油茶籽油、油橄榄果油、霍霍巴籽油、玉米油、玉米胚芽油、芝麻油、油菜籽油、棉籽油中的任意一种，研究表明，油脂类化合物都可以通过本发明的方法硒化，其原理类似，即硒物种作为强亲核试剂与油脂中的羰基反应，从而硒化油脂。
较佳的，硒与油脂的比例优选1mol:5L，油脂用量过低，无法充分吸收散逸的硒物种，导致硒利用率不高。油脂用量过高，则其中硒含量较低，导致使用时的一些操作不变(需要使用更大量的硒化油脂，不适合对产品体积要求小的场合)。
与现有技术相比，本发明具有如下有益效果：
本方法操作简单，产品易分离，且可以避免混入水溶性杂质，制备过程硒利用率高。硒化油脂在水中不溶，可以用于制造鱼、虾、蟹类的富硒饲料，也可应用于化妆品领域。
附图说明
图1为实施例1制备硒化油脂时分液的分层照片。
具体实施方式
下面的实施例对本发明进行更详细的阐述，而不是对本发明的进一步限定。
本发明以各种油类为载体，通过独特的羟基醛酮接力硒化技术，可以高硒利用率地制备硒化油脂。产品的水不溶性质使其中水溶性杂质可以很好地通过水洗涤来去除，还使得产品可以应用于制作鱼饲料，有很好的应用前景。
本发明公开了以硒氢化钠为硒化试剂、羟基醛酮为催化剂、有机酸为酸度调节剂硒化油脂制备硒化油脂的方法。
实施例1
硒氢化钠的制备：在一个装有回流冷凝管的50毫升三颈烧瓶中，加入4mmol硒粉(0.32g)、4.8mmol硼氢化钠(0.18g)和一颗磁力搅拌子，用氮气置换其中的空气后，注入25mL无水乙醇，搅拌，反应后体系温度会逐渐升高。磁力搅拌1小时后，加热回流3小时，即得硒氢化钠乙醇溶液。将其转移到圆底烧瓶中，用旋转蒸发仪蒸干，加入30毫升水，配成硒氢化钠水溶液。
硒化油脂的制备：在上述硒氢化钠水溶液中，加入0.16mmol甘油醛和20mL大豆油，再加入2.72mmol柠檬酸，室温搅拌24小时后分液(图1)，上层油料水洗干燥后即硒化油脂。电感耦合等离子体色谱-质谱(ICP-Ms)测定表明，制备的油料中含硒308.4mg，即整个过程硒利用率(即308.4/320)为96.4％。
实施例2
其他条件同实施例1,检验使用不同羟基醛酮做催化剂制备硒化油脂的效果，实验结果见表1。
表1使用不同羟基醛酮做催化剂制备硒化油脂的效果检验
由上述结果可知，使用甘油醛(实施例1)硒化效果最好，硒利用率最高。
实施例3
其他条件同实施例1，检验不同羟基醛酮用量的效果，实验结果如表2所示。
表2不同羟基醛酮用量的效果研究
由上述结果可知，硒与羟基醛酮用量比为1mol:0.04mol(实施例1)时，硒利用率最高。
实施例4
其他条件同实施例1,检验使用不同有机酸做助剂制备硒化油脂的效果，实验结果见表3。
表3使用不同有机酸做助剂制备硒化油脂的效果检验
由上述结果可知，使用柠檬酸(实施例1)做助剂，硒化效果最好，硒利用率最高。
实施例5
其他条件同实施例1，检验不同有机酸用量的效果，实验结果如表4所示。
表4不同有机酸用量的效果研究
由上述结果可知，硒与有机酸用量比为1mol:0.68mol(实施例1)时，硒利用率最高。
实施例6
其他条件同实施例1,检验使用不同油脂备硒化油脂的效果，实验结果见表5。
表5使用不同油脂制备硒化油脂的效果检验
【注】常温下是固体的油脂，需加热融化后使用。
由上述结果可知，各种油脂都可以通过本方法硒化。
实施例7
其他条件同实施例1，检验不同油脂用量的效果，实验结果如表6所示。
表6不同油脂用量的效果研究
由上述结果可知，硒与油脂用量比为1mol:5L(实施例1)时，硒利用率达到最高。增加油脂用量不能进一步提高硒利用率，而减少油脂用量反而会降低硒利用率。
以上所述，仅是本发明的较佳实施例，并非对本发明作任何形式上的限制，任何熟悉本专业的技术人员，在不脱离本发明技术方案范围内，依据本发明的技术实质，对以上实施例所作的任何简单的修改、等同替换与改进等，均仍属于本发明技术方案的保护范围之内。
Claims (6)
1.一种硒化油脂的制备方法，其特征在于，在硒氢化钠溶液中，加入羟基醛酮、有机酸、油脂，其中，投料比为：硒：羟基醛酮：有机酸：油脂= 1 mol : 0.02～0.06 mol : 0.62～0.74 mol : 2～8 L；所得混合液搅拌24小时以上，后分液，上层油料水洗干燥后即得硒化油脂；羟基醛酮为甘油醛；有机酸为柠檬酸。
2.如权利要求1所述的方法，其特征在于，硒氢化钠是通过硼氢化钠还原硒粉制备。
3. 如权利要求1所述的方法，其特征在于，硒与羟基醛酮的比例为1 mol :0.04 mol。
4. 如权利要求1所述的方法，其特征在于，硒与有机酸的比例为1 mol :0.68 mol。
5.如权利要求1所述的方法，其特征在于，油脂为色拉油、橄榄油、葵花籽油、花生油、棕榈油、猪油、牛油、羊油、大豆油、柠檬果皮油、葡萄籽油、野大豆油、油茶籽油、油橄榄果油、霍霍巴籽油、玉米油、玉米胚芽油、芝麻油、油菜籽油、棉籽油中的任意一种。
6. 如权利要求1所述的方法，其特征在于，硒与油脂的比例为1 mol :5 L。
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