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CN111635310A - A kind of salicylic acid amide type corrosion inhibitor for protecting copper from corrosion in weak alkaline medium and preparation method thereof - Google Patents

A kind of salicylic acid amide type corrosion inhibitor for protecting copper from corrosion in weak alkaline medium and preparation method thereof Download PDF

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CN111635310A
CN111635310A CN202010434508.8A CN202010434508A CN111635310A CN 111635310 A CN111635310 A CN 111635310A CN 202010434508 A CN202010434508 A CN 202010434508A CN 111635310 A CN111635310 A CN 111635310A
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salicylic acid
corrosion inhibitor
corrosion
acid amide
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姜文凤
张天保
王慧龙
张淑芬
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Dalian University of Technology
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    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/58—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/60—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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    • C07C235/64—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
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    • C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
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Abstract

一种用于防护铜在弱碱性介质中腐蚀的水杨酸酰胺型缓蚀剂及制备方法，属于精细化工产品开发技术领域。该缓蚀剂的核心结构为

Figure DDA0002501725610000011
该缓蚀剂制备方法简单，设备要求低，易于实现，缓蚀率较高，适合作为紫铜在碳酸氢钠溶液中的缓蚀剂。本发明通过对来源广泛的水杨酸进行结构改性，增加其与金属表面的化学物理作用，从而实现高效的缓蚀作用。同时，其具有良好的溶解性，便于投药操作，适合用于紫铜在碱性条件下的腐蚀防护。A salicylic acid amide type corrosion inhibitor for protecting copper from corrosion in a weak alkaline medium and a preparation method thereof belong to the technical field of fine chemical product development. The core structure of the corrosion inhibitor is
Figure DDA0002501725610000011
The corrosion inhibitor has the advantages of simple preparation method, low equipment requirements, easy realization and high corrosion inhibition rate, and is suitable as a corrosion inhibitor for red copper in sodium bicarbonate solution. The present invention achieves high-efficiency corrosion inhibition by modifying the structure of salicylic acid with a wide range of sources and increasing its chemical and physical interaction with the metal surface. At the same time, it has good solubility, is convenient for drug administration, and is suitable for corrosion protection of red copper under alkaline conditions.

Description

一种用于防护铜在弱碱性介质中腐蚀的水杨酸酰胺型缓蚀剂 及制备方法A salicylic acid amide type corrosion inhibitor for protecting copper from corrosion in weak alkaline medium and preparation method

技术领域technical field

本发明属于精细化工产品开发技术领域，涉及一种用于5％碳酸氢钠溶液中的紫铜件保护的水杨酸酰胺型缓蚀剂及其制备方法。The invention belongs to the technical field of fine chemical product development, and relates to a salicylic acid amide type corrosion inhibitor for protecting red copper pieces in a 5% sodium bicarbonate solution and a preparation method thereof.

背景技术Background technique

在制造业转型升级过程中，金属的腐蚀问题必须需要给予关注。金属腐蚀是一种悄无声息的破坏，每年由于金属材料的腐蚀失效问题所造成的各类经济损失巨大。金属铜是一种常见的有色金属材料，广泛应用于国民经济各个部门。其在大气中，以及中性、弱碱性环境中的腐蚀问题，值得关注。铜基中性、碱性条件下缓蚀剂主要为苯并三氮唑(BTA)，但是近年来，苯并三氮唑被发现有一定的致癌性，欧盟等一些国际组织已经逐步禁止BTA的广泛应用，因此开发新型应用于Cu的缓蚀剂开发成为研究的重点，目前文献中报道仍然以苯并三氮唑、巯基苯并咪唑等为主。它们合成困难，毒性较大，并不适合目前及以后的发展趋势。水杨酸是一种无毒的、常见的原料，被广泛用于医药等领域，以此为母体化合物开发新型缓蚀剂具有很大的意义。In the process of transformation and upgrading of the manufacturing industry, the corrosion of metals must be paid attention to. Metal corrosion is a kind of silent destruction, and various economic losses are caused by the corrosion failure of metal materials every year. Copper metal is a common non-ferrous metal material and is widely used in various sectors of the national economy. Its corrosion in the atmosphere and in neutral and weak alkaline environments is worthy of attention. Under copper-based neutral and alkaline conditions, the corrosion inhibitor is mainly benzotriazole (BTA). However, in recent years, benzotriazole has been found to have certain carcinogenicity. Therefore, the development of new corrosion inhibitors for Cu has become the focus of research. At present, the reports in the literature are still mainly benzotriazole and mercaptobenzimidazole. They are difficult to synthesize, have high toxicity, and are not suitable for current and future development trends. Salicylic acid is a non-toxic and common raw material, which is widely used in medicine and other fields. It is of great significance to develop new corrosion inhibitors as the parent compound.

发明内容SUMMARY OF THE INVENTION

本发明的目的是提供一种在工业应用中少量、高效，适用于弱碱性条件下铜的缓蚀剂，它能够减小铜件的腐蚀速率，并且提供该缓蚀剂的制备方法。The purpose of the present invention is to provide a small amount of high-efficiency corrosion inhibitor suitable for copper under weak alkaline conditions in industrial applications, which can reduce the corrosion rate of copper parts, and provides a preparation method of the corrosion inhibitor.

为了达到上述目的，本发明采用的技术方案为：In order to achieve the above object, the technical scheme adopted in the present invention is:

一种用于防护铜在弱碱性介质中腐蚀的水杨酸酰胺型缓蚀剂，所述水杨酸酰胺型缓蚀剂的结构式为：

Figure BDA0002501725600000011
式中，R代表脂肪基团、芳基、不饱和基团中的任意一种。A salicylic acid amide type corrosion inhibitor for protecting copper from corrosion in a weak alkaline medium, the structural formula of the salicylic acid amide type corrosion inhibitor is:
Figure BDA0002501725600000011
In the formula, R represents any one of aliphatic group, aryl group and unsaturated group.

进一步的，所述脂肪基团包括正丁基、正丙基等，优选为正丁胺；芳基包括苯基、对甲苯基，优选为苯胺；不饱和基团为氰基，优选为氰胺。Further, the aliphatic group includes n-butyl group, n-propyl group, etc., preferably n-butylamine; aryl group includes phenyl group, p-tolyl group, preferably aniline; unsaturated group is cyano group, preferably cyanamide .

一种用于防护铜在弱碱性介质中腐蚀的水杨酸酰胺型缓蚀剂的制备方法，包括以下步骤：A preparation method of a salicylic acid amide type corrosion inhibitor for protecting copper from corrosion in a weak alkaline medium, comprising the following steps:

Figure BDA0002501725600000012
Figure BDA0002501725600000012

(1)在0℃低温下，将水杨酸和酰化试剂按照摩尔比1：1～1：5混合加入溶剂中，低温搅拌3-12h。(1) At a low temperature of 0°C, mix salicylic acid and acylating reagent into a solvent according to a molar ratio of 1:1 to 1:5, and stir at low temperature for 3-12 hours.

所述的溶剂包括1,4-二氧六环、四氢呋喃、二氯甲烷中的一种。所述的酰化试剂包括二氯亚砜、草酰氯、三氯化磷中的一种。The solvent includes one of 1,4-dioxane, tetrahydrofuran and dichloromethane. The acylating reagent includes one of thionyl chloride, oxalyl chloride and phosphorus trichloride.

(2)在步骤(1)的反应混合物中不经分离直接加入胺，在25～60℃温度条件下反应12-24h。所述胺与水杨酸摩尔比为1:1～3:1；所述胺为正丁胺、氰胺、苯胺中的任意一种。(2) The amine is directly added to the reaction mixture of step (1) without separation, and the reaction is carried out at a temperature of 25-60° C. for 12-24 hours. The molar ratio of the amine to the salicylic acid is 1:1 to 3:1; the amine is any one of n-butylamine, cyanamide and aniline.

(3)以盐酸调节体系的pH到6-7，再加入二氯甲烷萃取，置于0-5℃条件下，待沉淀析出后过滤得到产物。(3) Adjust the pH of the system to 6-7 with hydrochloric acid, then add dichloromethane for extraction, place at 0-5°C, and filter to obtain the product after precipitation.

与现有技术相比，本发明的有益效果为：Compared with the prior art, the beneficial effects of the present invention are:

(1)与现有技术相比，分子中引入的酰胺基团能够增强分子与铜的配位能力。分子中引入的烷基、氰基、芳基能够增加分子的作用位点，有利于分子吸附在铜表面，形成稳定的吸附膜。(1) Compared with the prior art, the amide group introduced into the molecule can enhance the coordination ability of the molecule and copper. The alkyl group, cyano group and aryl group introduced into the molecule can increase the action site of the molecule, which is conducive to the adsorption of the molecule on the copper surface to form a stable adsorption film.

(2)本发明缓蚀剂水溶性好，很快溶解于弱碱性溶液中，与现有铜相比，合成路线简单，原料成本较低，具有较好的应用前景。(2) The corrosion inhibitor of the present invention has good water solubility and is quickly dissolved in a weak alkaline solution. Compared with the existing copper, the corrosion inhibitor has a simple synthesis route, a lower cost of raw materials, and a better application prospect.

具体实施方式Detailed ways

下面结合实施例对本发明进一步详细说明，但本发明的保护范围不仅限于这些实施例。The present invention is further described in detail below with reference to the examples, but the protection scope of the present invention is not limited to these examples.

实施例1Example 1

(1)以二氯甲烷为溶剂，将水杨酸(13.8g)和二氯亚砜(11.8g)按1：1的摩尔比在0℃混合在一起，在低温度下搅拌3h。(1) Using dichloromethane as a solvent, salicylic acid (13.8 g) and thionyl chloride (11.8 g) were mixed together in a molar ratio of 1:1 at 0° C., and stirred at low temperature for 3 h.

(2)在反应混合物中加入正丁胺(7.3g)，其中，正丁胺与水杨酸摩尔比为1:1，在25℃反应12h。(2) n-butylamine (7.3 g) was added to the reaction mixture, wherein the molar ratio of n-butylamine and salicylic acid was 1:1, and the reaction was carried out at 25° C. for 12 h.

(3)以盐酸酸调节体系pH为6-7，加入二氯甲烷萃取，置于低温，待沉淀析出、过滤，得产物。(3) Adjust the pH of the system to 6-7 with hydrochloric acid, add dichloromethane for extraction, place at a low temperature, wait for precipitation, and filter to obtain the product.

实施例2Example 2

(1)以四氢呋喃为溶剂，将水杨酸(13.8g)和草酰氯(38.1g)按1：3的摩尔比在0℃混合在一起，在低温度下搅拌8h。(1) Using tetrahydrofuran as a solvent, salicylic acid (13.8 g) and oxalyl chloride (38.1 g) were mixed together in a molar ratio of 1:3 at 0° C., and stirred at low temperature for 8 h.

(2)在反应混合物中加入氰胺(8.4g)，其中，氰胺与水杨酸摩尔比为2:1，在40℃反应18h。(2) cyanamide (8.4 g) was added to the reaction mixture, wherein the molar ratio of cyanamide and salicylic acid was 2:1, and the reaction was carried out at 40° C. for 18 hours.

(3)以盐酸酸调节体系pH为6-7，加入二氯甲烷萃取，置于低温，待沉淀析出、过滤，得产物。(3) Adjust the pH of the system to 6-7 with hydrochloric acid, add dichloromethane for extraction, place at a low temperature, wait for precipitation, and filter to obtain the product.

实施例3Example 3

(1)以1,4-二氧六环为溶剂，将水杨酸(13.8g)和三氯化磷(68.7g)按1：5的摩尔比在0℃混合在一起，在低温度下搅拌12h。(1) Using 1,4-dioxane as a solvent, salicylic acid (13.8g) and phosphorus trichloride (68.7g) were mixed together in a molar ratio of 1:5 at 0°C, and at a low temperature Stir for 12h.

(2)在反应混合物中加入苯胺(27.9g)，其中，苯胺与水杨酸摩尔比为3:1，在60℃反应24h。(2) Aniline (27.9 g) was added to the reaction mixture, wherein the molar ratio of aniline and salicylic acid was 3:1, and the reaction was carried out at 60° C. for 24 hours.

(3)以盐酸酸调节体系pH为6-7，加入二氯甲烷萃取，置于低温，待沉淀析出、过滤，得产物。(3) Adjust the pH of the system to 6-7 with hydrochloric acid, add dichloromethane for extraction, place at a low temperature, wait for precipitation, and filter to obtain the product.

以氰胺为例，电化学实验证明铜在含有300ppm所合成缓蚀剂的5％碳酸氢钠中腐蚀速率最低。Taking cyanamide as an example, electrochemical experiments show that copper has the lowest corrosion rate in 5% sodium bicarbonate containing 300ppm of the synthesized corrosion inhibitor.

Figure BDA0002501725600000031
Figure BDA0002501725600000031

由氰胺的缓蚀性能可知，该水杨酸酰胺型缓蚀剂具有抑制弱碱性溶液中的铜的腐蚀作用。说明分子中的杂原子与金属作用较强，在合金表面形成了稳定吸附膜，说明本发明水杨酸酰胺型缓蚀剂对弱碱溶液中铜的腐蚀具有优秀的抑制能力。It can be known from the corrosion inhibition performance of cyanamide that the salicylic acid amide type corrosion inhibitor has the effect of inhibiting the corrosion of copper in weak alkaline solution. It shows that the heteroatom in the molecule has a strong interaction with the metal, and a stable adsorption film is formed on the surface of the alloy, which shows that the salicylic acid amide type corrosion inhibitor of the present invention has an excellent inhibitory ability to the corrosion of copper in a weak alkaline solution.

以上所述实施例仅表达本发明的实施方式，但并不能因此而理解为对本发明专利的范围的限制，应当指出，对于本领域的技术人员来说，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，这些均属于本发明的保护范围。The above-mentioned embodiments only represent the embodiments of the present invention, but should not be construed as a limitation on the scope of the present invention. It should be pointed out that for those skilled in the art, without departing from the concept of the present invention, Several modifications and improvements can also be made, which all belong to the protection scope of the present invention.

Claims (5)

1.一种用于防护铜在弱碱性介质中腐蚀的水杨酸酰胺型缓蚀剂，其特征在于，所述水杨酸酰胺型缓蚀剂的结构式为：
Figure FDA0002501725590000011
式中，R代表脂肪基团、芳基、不饱和基团中的任意一种。1. a salicylic acid amide type corrosion inhibitor for protecting copper from corrosion in weak alkaline medium, is characterized in that, the structural formula of described salicylic acid amide type corrosion inhibitor is:
Figure FDA0002501725590000011
In the formula, R represents any one of aliphatic group, aryl group and unsaturated group. 2.根据权利要求1所述的一种用于防护铜在弱碱性介质中腐蚀的水杨酸酰胺型缓蚀剂，其特征在于，所述脂肪基团包括正丁基、正丙基；芳基包括苯基、对甲苯基；不饱和基团为氰基。2. a kind of salicylic acid amide type corrosion inhibitor for protecting copper from corrosion in weak alkaline medium according to claim 1, is characterized in that, described aliphatic group comprises n-butyl group, n-propyl group; Aryl includes phenyl, p-tolyl; unsaturated group is cyano. 3.根据权利要求1或2所述的一种用于防护铜在弱碱性介质中腐蚀的水杨酸酰胺型缓蚀剂，其特征在于，所述脂肪基团优选为正丁胺；芳基优选为苯胺；不饱和基团优选为氰胺。3. a kind of salicylic acid amide type corrosion inhibitor for protecting copper from corrosion in weak alkaline medium according to claim 1 and 2, is characterized in that, described aliphatic group is preferably n-butylamine; The group is preferably aniline; the unsaturated group is preferably cyanamide. 4.一种权利要求1-3任一所述的用于防护铜在弱碱性介质中腐蚀的水杨酸酰胺型缓蚀剂的制备方法，其特征在于，包括以下步骤：4. the preparation method of the arbitrary described salicylic acid amide type corrosion inhibitor for protecting copper in weak alkaline medium described in claim 1-3, is characterized in that, comprises the following steps: (1)在0℃低温下，将水杨酸和酰化试剂按照摩尔比1：1～1：5混合加入溶剂中，低温搅拌3-12h；所述的酰化试剂包括二氯亚砜、草酰氯、三氯化磷中的一种；(1) At a low temperature of 0 °C, mix salicylic acid and acylating reagent into a solvent according to a molar ratio of 1:1 to 1:5, and stir at low temperature for 3-12 hours; the acylating reagent includes thionyl chloride, One of oxalyl chloride and phosphorus trichloride; (2)在步骤(1)的反应混合物中不经分离直接加入胺，在25～60℃温度条件下反应12-24h；所述胺与水杨酸摩尔比为1:1～3:1；所述胺为正丁胺、氰胺、苯胺中的任意一种；(2) adding amine directly into the reaction mixture of step (1) without separation, and reacting at 25～60℃ for 12-24h; the molar ratio of amine and salicylic acid is 1:1～3:1; Described amine is any one in n-butylamine, cyanamide, aniline; (3)以盐酸调节体系的pH到6-7，再加入二氯甲烷萃取，置于0-5℃条件下，待沉淀析出后过滤得到产物。(3) Adjust the pH of the system to 6-7 with hydrochloric acid, then add dichloromethane for extraction, place at 0-5°C, and filter to obtain the product after precipitation. 5.根据权利要求4所述的用于防护铜在弱碱性介质中腐蚀的水杨酸酰胺型缓蚀剂的制备方法，其特征在于，所述的溶剂包括1,4-二氧六环、四氢呋喃、二氯甲烷中的一种。5. the preparation method of the salicylic acid amide type corrosion inhibitor that is used to protect copper from corrosion in weak alkaline medium according to claim 4, is characterized in that, described solvent comprises 1,4-dioxane , one of tetrahydrofuran and dichloromethane.
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US4563253A (en) * 1982-10-27 1986-01-07 Lehigh University Method of making corrosion inhibited metal
CN101050537A (en) * 2006-04-04 2007-10-10 中国石油天然气股份有限公司 A kind of corrosion inhibitor for suppressing metal corrosion and preparation method thereof
CN103351309A (en) * 2013-07-24 2013-10-16 中国船舶重工集团公司第七二五研究所 Salicylic amide antifoulant and preparation method thereof
CN105523955A (en) * 2015-12-14 2016-04-27 清华大学 Compound and application of compound in preparation of medicines

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4563253A (en) * 1982-10-27 1986-01-07 Lehigh University Method of making corrosion inhibited metal
CN101050537A (en) * 2006-04-04 2007-10-10 中国石油天然气股份有限公司 A kind of corrosion inhibitor for suppressing metal corrosion and preparation method thereof
CN103351309A (en) * 2013-07-24 2013-10-16 中国船舶重工集团公司第七二五研究所 Salicylic amide antifoulant and preparation method thereof
CN105523955A (en) * 2015-12-14 2016-04-27 清华大学 Compound and application of compound in preparation of medicines

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