CN111848428A - A kind of preparation method of γ-glycine and γ-glycine - Google Patents
A kind of preparation method of γ-glycine and γ-glycine Download PDFInfo
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- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 title claims abstract description 119
- 238000002360 preparation method Methods 0.000 title claims abstract description 46
- 239000004471 Glycine Substances 0.000 claims abstract description 41
- 238000000498 ball milling Methods 0.000 claims abstract description 37
- 239000000203 mixture Substances 0.000 claims abstract description 26
- 239000003054 catalyst Substances 0.000 claims abstract description 23
- 239000002994 raw material Substances 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 13
- 238000002156 mixing Methods 0.000 claims abstract description 5
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical group [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000000227 grinding Methods 0.000 claims description 6
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 claims description 6
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 claims description 6
- 235000011164 potassium chloride Nutrition 0.000 claims description 4
- 239000001103 potassium chloride Substances 0.000 claims description 4
- 239000011780 sodium chloride Substances 0.000 claims description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 3
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 claims description 3
- 229910000402 monopotassium phosphate Inorganic materials 0.000 claims description 3
- 235000019796 monopotassium phosphate Nutrition 0.000 claims description 3
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 claims description 3
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 claims description 3
- 229910052939 potassium sulfate Inorganic materials 0.000 claims description 3
- 235000011151 potassium sulphates Nutrition 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 3
- 235000011152 sodium sulphate Nutrition 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000000926 separation method Methods 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 231100000252 nontoxic Toxicity 0.000 abstract description 3
- 230000003000 nontoxic effect Effects 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 18
- 239000000243 solution Substances 0.000 description 7
- 238000002441 X-ray diffraction Methods 0.000 description 6
- 239000013078 crystal Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000009916 joint effect Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 230000006911 nucleation Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/38—Separation; Purification; Stabilisation; Use of additives
- C07C227/40—Separation; Purification
- C07C227/42—Crystallisation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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Abstract
本发明提供了一种γ型甘氨酸的制备方法及γ型甘氨酸，涉及工业原料的制备工艺技术领域。该制备方法包括如下步骤：将甘氨酸原料与催化剂混合形成混合物；以及采用球磨法对上述混合物进行球磨处理后得到γ型甘氨酸。本发明的制备方法能够直接将甘氨酸原料α型甘氨酸完全转变为γ型甘氨酸，制备过程中无需对生产过程进行调节，操作简单成熟。另外，本发明实施例的γ型甘氨酸的制备方法中催化剂无毒惰性，制备后无需对产物γ型甘氨酸做后续分离处理，使得制备工艺更加简单。
The invention provides a preparation method of γ-type glycine and γ-type glycine, and relates to the technical field of preparation technology of industrial raw materials. The preparation method comprises the following steps: mixing the glycine raw material and the catalyst to form a mixture; and performing ball milling on the above mixture by a ball milling method to obtain γ-glycine. The preparation method of the invention can directly completely convert the α-type glycine of the glycine raw material into the γ-type glycine, the production process does not need to be adjusted in the preparation process, and the operation is simple and mature. In addition, in the preparation method of γ-glycine of the embodiment of the present invention, the catalyst is non-toxic and inert, and subsequent separation treatment of the product γ-glycine is unnecessary after preparation, which makes the preparation process simpler.
Description
技术领域technical field
本发明涉及一种工业原料的制备工艺技术领域，且特别涉及一种γ型甘氨酸的制备方法及γ型甘氨酸。The invention relates to the technical field of a preparation process of industrial raw materials, and particularly relates to a preparation method of γ-type glycine and γ-type glycine.
背景技术Background technique
甘氨酸是结构最简单的氨基酸，是食品、医药等领域的重要原料。甘氨酸常见晶型有3种：α、β和γ型。其中γ型是稳定相，α型是亚稳定相，β型是不稳定相。α型在低温干燥的条件下稳定存在，但在湿热环境下会发生向稳定相γ型的转变。由于结晶动力学问题，水溶液中制备甘氨酸晶体的过程中一般优先得到亚稳定相α型。α型甘氨酸在储存和运输过程中如果发生晶型转变会造成产品结块，造成使用不便。γ型甘氨酸由于其特殊的非对称的极性结构，是一种先进优良的压电材料和非线性光学材料。因此，γ型甘氨酸能够有效解决甘氨酸产品稳定性差的问题，提升其使用效果。Glycine is the simplest amino acid and an important raw material in the fields of food and medicine. There are three common crystal forms of glycine: α, β and γ. The γ-type is the stable phase, the α-type is the metastable phase, and the β-type is the unstable phase. The α-type exists stably under low temperature and dry conditions, but it will transform to the stable γ-type in a humid and hot environment. Due to the problem of crystallization kinetics, the metastable phase α-type is generally preferentially obtained during the preparation of glycine crystals in aqueous solution. If α-glycine undergoes crystal transformation during storage and transportation, it will cause the product to agglomerate and cause inconvenience to use. Because of its special asymmetric polar structure, γ-glycine is an advanced and excellent piezoelectric material and nonlinear optical material. Therefore, γ-glycine can effectively solve the problem of poor stability of glycine products and improve its use effect.
目前，国外的甘氨酸产品主要为γ型。γ型甘氨酸的成核和生长非常敏感，制备γ型甘氨酸的方法主要是溶液相方法，如在酸化、碱化处理过的或添加碱金属盐的甘氨酸溶液中结晶制备，在指定pH值的甘氨酸水溶液中利用α型甘氨酸加热转化制备，但是该制备工艺过程和条件不容易控制，而且通过溶液相制备的γ型甘氨酸还需将最终产品分离得到。At present, foreign glycine products are mainly γ-type. The nucleation and growth of γ-glycine is very sensitive, and the methods for preparing γ-glycine are mainly solution-phase methods, such as crystallization in acidified, alkalized or alkali metal salt-added glycine solutions, and glycine at a specified pH value. It is prepared by heating and converting α-glycine in an aqueous solution, but the preparation process and conditions are not easy to control, and the γ-glycine prepared by the solution phase needs to be separated from the final product.
发明内容SUMMARY OF THE INVENTION
本发明的目的在于提供一种γ型甘氨酸的制备方法，此γ型甘氨酸的制备方法廉价、操作简便且无需分离。The purpose of the present invention is to provide a preparation method of γ-glycine, which is inexpensive, easy to operate and does not require separation.
本发明的目的还在于提供一种γ型甘氨酸。Another object of the present invention is to provide a γ-glycine.
本发明解决其技术问题是采用以下技术方案来实现的。The present invention solves its technical problems by adopting the following technical solutions.
本发明提出一种γ型甘氨酸的制备方法，其特征在于，其包括如下步骤：The present invention proposes a preparation method of γ-glycine, characterized in that it comprises the following steps:
将甘氨酸原料与催化剂混合形成混合物；以及mixing the glycine feedstock with the catalyst to form a mixture; and
采用球磨法对上述混合物进行球磨处理后得到γ型甘氨酸。γ-glycine is obtained after the above mixture is ball-milled by a ball-milling method.
根据一种优选实施方式，所述混合物中甘氨酸原料与催化剂的质量比为：500：(1-500)。According to a preferred embodiment, the mass ratio of the glycine raw material to the catalyst in the mixture is: 500:(1-500).
根据一种优选实施方式，所述混合物中催化剂的质量百分比为0.2wt％。According to a preferred embodiment, the mass percentage of the catalyst in the mixture is 0.2 wt %.
根据一种优选实施方式，所述催化剂为稳定型无机盐的一种或几种。According to a preferred embodiment, the catalyst is one or more stable inorganic salts.
根据一种优选实施方式，所述催化剂选自氯化钾、溴化钾、硫酸钾、磷酸氢二钾、磷酸二氢钾、氯化钠、溴化钠或硫酸钠中的一种或几种。According to a preferred embodiment, the catalyst is selected from one or more of potassium chloride, potassium bromide, potassium sulfate, dipotassium hydrogen phosphate, potassium dihydrogen phosphate, sodium chloride, sodium bromide or sodium sulfate .
根据一种优选实施方式，所述甘氨酸原料为α型甘氨酸。According to a preferred embodiment, the glycine raw material is α-glycine.
根据一种优选实施方式，所述的采用球磨法对上述混合物进行球磨处理的步骤还包括：加入助磨成分，所述助磨成分为水或乙醇。According to a preferred embodiment, the step of performing ball milling on the above mixture by ball milling further comprises: adding a grinding aid component, wherein the grinding aid component is water or ethanol.
根据一种优选实施方式，球磨处理时间为10min-2h。According to a preferred embodiment, the ball milling treatment time is 10min-2h.
根据一种优选实施方式，球磨处理温度为常温至60℃。According to a preferred embodiment, the ball milling treatment temperature is from normal temperature to 60°C.
本发明还提供了一种γ型甘氨酸，所述γ型甘氨酸是由所述的制备方法制备而成。The present invention also provides a γ-type glycine, the γ-type glycine is prepared by the said preparation method.
基于上述技术方案，本发明的γ型甘氨酸的制备方法至少具有如下技术效果：Based on the above technical solutions, the preparation method of γ-glycine of the present invention has at least the following technical effects:
本发明提供的γ型甘氨酸的制备方法通过将甘氨酸原料和催化剂混合形成混合物，然后采用球磨法对混合物进行球磨处理得到γ型甘氨酸。在物理球磨与催化剂的共同作用下，本发明的制备方法能够直接将甘氨酸原料α型甘氨酸完全转变为γ型甘氨酸，制备过程中无需对生产过程进行调节，操作简单成熟。The preparation method of γ-type glycine provided by the present invention is to obtain γ-type glycine by mixing glycine raw materials and a catalyst to form a mixture, and then performing ball milling on the mixture by a ball milling method. Under the combined action of the physical ball milling and the catalyst, the preparation method of the present invention can directly convert the α-type glycine of the glycine raw material into the γ-type glycine, and the production process does not need to be adjusted in the preparation process, and the operation is simple and mature.
另外，本发明实施例的γ型甘氨酸的制备方法中催化剂无毒惰性，制备后无需对产物γ型甘氨酸做后续分离处理，使得制备工艺更加简单。In addition, in the preparation method of γ-glycine of the embodiment of the present invention, the catalyst is non-toxic and inert, and subsequent separation treatment of the product γ-glycine is unnecessary after preparation, which makes the preparation process simpler.
附图说明Description of drawings
为了更清楚地说明本发明实施例的技术方案，下面将对实施例中所需要使用的附图作简单地介绍，应当理解，以下附图仅示出了本发明的某些实施例，因此不应被看作是对范围的限定，对于本领域普通技术人员来讲，在不付出创造性劳动的前提下，还可以根据这些附图获得其他相关的附图。In order to illustrate the technical solutions of the embodiments of the present invention more clearly, the following briefly introduces the accompanying drawings used in the embodiments. It should be understood that the following drawings only show some embodiments of the present invention, and therefore do not It should be regarded as a limitation of the scope, and for those of ordinary skill in the art, other related drawings can also be obtained according to these drawings without any creative effort.
图1为本发明的实施例1制备产物的XRD图；Fig. 1 is the XRD pattern of the preparation product of embodiment 1 of the present invention;
图2为本发明的实施例2制备产物的XRD图；Fig. 2 is the XRD pattern of the preparation product of embodiment 2 of the present invention;
图3为本发明的实施例3制备产物的XRD图。Fig. 3 is the XRD pattern of the product prepared in Example 3 of the present invention.
具体实施方式Detailed ways
为使本发明实施例的目的、技术方案和优点更加清楚，下面将对本发明实施例中的技术方案进行清楚、完整地描述。实施例中未注明具体条件者，按照常规条件或制造商建议的条件进行。所用试剂或仪器未注明生产厂商者，均为可以通过市售购买获得的常规产品。In order to make the objectives, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be described clearly and completely below. If the specific conditions are not indicated in the examples, it is carried out according to the conventional conditions or the conditions suggested by the manufacturer. The reagents or instruments used without the manufacturer's indication are conventional products that can be purchased from the market.
下面对本发明实施例的γ型甘氨酸的制备方法进行具体说明。The preparation method of γ-glycine according to the embodiment of the present invention will be specifically described below.
本发明提供了一种γ型甘氨酸的制备方法，其包括如下步骤：The invention provides a preparation method of γ-glycine, which comprises the following steps:
将甘氨酸原料与催化剂混合形成混合物；以及mixing the glycine feedstock with the catalyst to form a mixture; and
采用球磨法对上述混合物进行球磨处理后得到γ型甘氨酸。γ-glycine is obtained after the above mixture is ball-milled by a ball-milling method.
优选的，混合物中甘氨酸原料与催化剂的质量比为：500：(1-500)。优选的，混合物中催化剂的质量百分比为0.2wt％。优选的，催化剂为稳定型无机盐的一种或几种。优选的，催化剂选自氯化钾、溴化钾、硫酸钾、磷酸氢二钾、磷酸二氢钾、氯化钠、溴化钠或硫酸钠中的一种或几种。因此混合物中的催化剂含量可以很低，而且无毒，具有惰性，因此无需对制备的γ型甘氨酸进行后续分离处理，简化了处理工艺。Preferably, the mass ratio of the glycine raw material to the catalyst in the mixture is: 500:(1-500). Preferably, the mass percentage of the catalyst in the mixture is 0.2 wt%. Preferably, the catalyst is one or more stable inorganic salts. Preferably, the catalyst is selected from one or more of potassium chloride, potassium bromide, potassium sulfate, dipotassium hydrogen phosphate, potassium dihydrogen phosphate, sodium chloride, sodium bromide or sodium sulfate. Therefore, the catalyst content in the mixture can be very low, and it is non-toxic and inert, so there is no need to carry out subsequent separation treatment on the prepared γ-glycine, which simplifies the treatment process.
优选的，甘氨酸原料为α型甘氨酸。Preferably, the glycine raw material is α-glycine.
优选的，采用球磨法对混合物进行球磨处理的步骤还包括：加入助磨成分，助磨成分为水或乙醇。优选的，球磨处理时间为10min-2h。优选的，球磨处理温度为常温至60℃。本发明的制备方法简单成熟，可以直接将α型甘氨酸原料完全转变为γ型甘氨酸，制备过程中无需对工艺进行调节。Preferably, the step of performing ball milling on the mixture by ball milling further comprises: adding a grinding aid component, and the grinding aid component is water or ethanol. Preferably, the ball milling treatment time is 10min-2h. Preferably, the temperature of the ball milling treatment ranges from normal temperature to 60°C. The preparation method of the invention is simple and mature, can directly convert the α-type glycine raw material into γ-type glycine, and does not need to adjust the process during the preparation process.
本发明还提供了一种γ型甘氨酸，γ型甘氨酸是由前述的制备方法制备而成。通过本发明的制备方法制备的γ型甘氨酸纯度较高。The present invention also provides a γ-type glycine, which is prepared by the aforementioned preparation method. The γ-type glycine prepared by the preparation method of the present invention has higher purity.
以下结合实施例对本发明的特征和性能作进一步的详细描述。The features and performances of the present invention will be further described in detail below in conjunction with the embodiments.
实施例1Example 1
本实施例提供了对比实施例，该实施例的制备方法包括如下步骤：The present embodiment provides a comparative example, and the preparation method of this embodiment comprises the following steps:
将1gα型甘氨酸通过球磨法进行球磨处理，球磨处理时间为1小时，球磨处理温度为常温，得到球磨产物。1 g of α-glycine is subjected to ball milling treatment by ball milling, the ball milling treatment time is 1 hour, and the ball milling treatment temperature is normal temperature to obtain a ball milling product.
如图1所示，图1示出了本实施例的球磨产物的XRD图，从图1可以看出，本实施例制备的球磨产物仍为α型甘氨酸。As shown in FIG. 1 , FIG. 1 shows the XRD pattern of the ball-milled product of this embodiment, and it can be seen from FIG. 1 that the ball-milled product prepared in this embodiment is still α-glycine.
实施例2Example 2
本实施例的制备方法包括如下步骤：The preparation method of the present embodiment comprises the following steps:
将1gα型甘氨酸和1g氯化钾混合形成混合物；Mix 1 g of α-glycine and 1 g of potassium chloride to form a mixture;
采用球磨法对上述混合物进行球磨处理，其中，球磨处理时间为1小时，球磨处理温度为常温，得到球磨产物。The above mixture is subjected to ball milling treatment by a ball milling method, wherein the ball milling treatment time is 1 hour, and the ball milling treatment temperature is normal temperature to obtain a ball milling product.
如图2所示，图2示出了本实施例的球磨产物的XRD图，从图2可以看出，本实施例制备的球磨产物为γ型甘氨酸。As shown in FIG. 2 , FIG. 2 shows the XRD pattern of the ball-milled product of this example, and it can be seen from FIG. 2 that the ball-milled product prepared in this example is γ-glycine.
实施例3Example 3
本实施例的制备方法包括如下步骤：The preparation method of the present embodiment comprises the following steps:
将1gα型甘氨酸和2mg氯化钠混合形成混合物；Mix 1 g of α-glycine and 2 mg of sodium chloride to form a mixture;
采用球磨法对上述混合物进行球磨处理，其中，球磨处理时间为1小时，球磨处理温度为常温，得到球磨产物。The above mixture is subjected to ball milling treatment by a ball milling method, wherein the ball milling treatment time is 1 hour, and the ball milling treatment temperature is normal temperature to obtain a ball milling product.
如图3所示，图3示出了本实施例的球磨产物的XRD图，从图3可以看出，本实施例制备的球磨产物为γ型甘氨酸。As shown in FIG. 3 , FIG. 3 shows the XRD pattern of the ball-milled product of this embodiment, and it can be seen from FIG. 3 that the ball-milled product prepared in this embodiment is γ-glycine.
因此，从实施例1和实施例2以及实施例3的对比可以看出，在催化剂的作用下，能够通过球磨处理使α型甘氨酸向γ型甘氨酸的完全转变，从而通过物理球磨和催化剂的共同作用，制备出γ型甘氨酸，本发明的制备方法具有廉价、操作简便且无需分离的优点。另外，申请人经试验得出，在实施例2和实施例3的基础上将甘氨酸原料和催化剂的用量扩大20倍，结果显示球磨产物仍为γ型甘氨酸，因此，本发明的制备方法可以用于工业生产，对于γ性甘氨酸的生产具有重大的经济价值。Therefore, from the comparison of Example 1, Example 2 and Example 3, it can be seen that under the action of the catalyst, α-glycine can be completely converted to γ-glycine by ball milling, so that the joint effect of physical ball milling and catalyst γ-type glycine is prepared by the action of the method, and the preparation method of the present invention has the advantages of low cost, simple operation and no separation. In addition, the applicant has obtained through experiments that on the basis of Example 2 and Example 3, the consumption of glycine raw materials and catalysts is expanded by 20 times, and the result shows that the ball-milled product is still γ-glycine. Therefore, the preparation method of the present invention can be used For industrial production, it has great economic value for the production of gamma glycine.
以上所描述的实施例是本发明一部分实施例，而不是全部的实施例。本发明的实施例的详细描述并非旨在限制要求保护的本发明的范围，而是仅仅表示本发明的选定实施例。基于本发明中的实施例，本领域普通技术人员在没有作出创造性劳动前提下所获得的所有其他实施例，都属于本发明保护的范围。The embodiments described above are some, but not all, embodiments of the present invention. The detailed descriptions of the embodiments of the invention are not intended to limit the scope of the invention as claimed, but are merely representative of selected embodiments of the invention. Based on the embodiments of the present invention, all other embodiments obtained by those of ordinary skill in the art without creative efforts shall fall within the protection scope of the present invention.
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