CN108047097A - 一种合成2-丙烯酰胺-2-甲基丙磺酸酯的方法及应用 - Google Patents

一种合成2-丙烯酰胺-2-甲基丙磺酸酯的方法及应用 Download PDF

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CN108047097A
CN108047097A CN201711305929.5A CN201711305929A CN108047097A CN 108047097 A CN108047097 A CN 108047097A CN 201711305929 A CN201711305929 A CN 201711305929A CN 108047097 A CN108047097 A CN 108047097A
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acrylamide
methyl propane
propane sulfonic
orthoformate
amps
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史野
左洪国
夏景刚
张惠军
黄红亮
李世杰
罗彪
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CNPC Bohai Drilling Engineering Co Ltd
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
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    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
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    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/52—Amides or imides
    • C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
    • C08F220/58—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine
    • C—CHEMISTRY; METALLURGY
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    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/52—Amides or imides
    • C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
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    • C08F220/585—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine and containing other heteroatoms, e.g. 2-acrylamido-2-methylpropane sulfonic acid [AMPS]

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Abstract

本发明提供了一种合成2‑丙烯酰胺‑2‑甲基丙磺酸酯的方法及应用，包括如下步骤：将AMPS加入到原甲酸酯中，在70‑100℃下反应1‑12h，蒸馏多余的原甲酸酯，即得到产物合成2‑丙烯酰胺‑2‑甲基丙磺酸酯，其中原甲酸酯的物质的量为AMPS物质的量的8～12倍。本发明所述的合成2‑丙烯酰胺‑2‑甲基丙磺酸酯的方法，合成步骤简单、反应条件温和，能得到有效延迟吸水膨胀率的原料2‑丙烯酰胺‑2‑甲基丙磺酸酯，为制备可延迟吸水膨胀率的堵漏剂提供了原料。

Description

一种合成2-丙烯酰胺-2-甲基丙磺酸酯的方法及应用
技术领域
本发明属于钻井堵漏材料技术领域，尤其是涉及一种合成2-丙烯酰胺-2-甲基丙磺酸酯的方法及应用。
背景技术
2-丙烯酰胺基-2-甲基丙磺酸(AMPS)是一种多功能的水溶性阴离子表面活性单体，极易自聚或者与其他烯烃共聚，可广泛应用与化纤、塑料、印染、涂料、油田化学品以及吸水树脂等领域。自20世纪90年代初投入工业化生产以来，随着生产工艺的不断成熟，产品生产能力逐渐扩大，对AMPS聚合物性能性能的认识不断深入，AMPS共聚物的研究和应用备受关注。在高吸水树脂领域中，引入AMPS可以大大改善吸水树脂的综合性能，因此在凝胶的合成中通常使用AMPS进行聚合。在可延迟吸水膨胀堵漏剂的合成中添加2-丙烯酰胺基-2-甲基丙磺酸酯(AMPSR)也可以大大改善其综合的性能，因此AMPSR得合成尤为关键。
以往合成酯的步骤大致为将酸制成酰氯，然后再与醇反应得到酯。合成步骤如下
实验步骤：取苯磺酸AMPS(210mg)，用二氯亚砜当作溶剂，加入几滴DMF为引发剂，室温反应2h，蒸去多余的二氯亚砜，向体系中加入甲醇，室温搅拌4h得到磺酸酯。
考虑酰氯法合成酯步骤比较繁琐，反应条件要求比较苛刻(需无水溶剂下进行)且试剂较为昂贵，不适合工业化生产。
发明内容
有鉴于此，本发明旨在提出一种合成2-丙烯酰胺-2-甲基丙磺酸酯的方法及应用，合成步骤简单、反应条件温和，能得到有效延迟吸水膨胀率的原料2-丙烯酰胺-2-甲基丙磺酸酯，为制备可延迟吸水膨胀率的堵漏剂提供了原料。
为达到上述目的，本发明的技术方案是这样实现的：
一种合成2-丙烯酰胺-2-甲基丙磺酸酯的方法，包括如下步骤：
将AMPS加入到原甲酸酯中，在70-100℃下反应1-12h，蒸馏多余的原甲酸酯，即得到产物合成2-丙烯酰胺-2-甲基丙磺酸酯，其中原甲酸酯的物质的量为AMPS物质的量的8～12倍，2-丙烯酰胺-2-甲基丙磺酸酯的结构式：
R＝甲基，乙基，丙基或丁基，反应方程式如下：
，R＝CH3，CH3CH2，CH3CH2CH2，CH3CH2CH2CH2。
进一步的，所述原甲酸酯为原甲酸三甲酯、原甲酸三乙酯、原甲酸三丙酯、原甲酸三丁酯中的任意一种。
进一步的，所述反应温度为70-100℃。
合成2-丙烯酰胺-2-甲基丙磺酸酯的反应机理：
本发明还提供了一种2-丙烯酰胺-2-甲基丙磺酸酯在制备新型可延迟膨胀类堵漏剂中的应用。
向盛有异丙醇的容器中加入2-丙烯酰胺-2-甲基丙磺酸酯、丙烯酸甲酯、丙烯酸，溶解后加入蒸馏水，然后加入交联剂和引发剂，室温下搅拌使其混合均匀，然后在50-80℃下静置，得到有机凝胶，反应方程式：
进一步的，所述搅拌时间为10-20min，静置时间为8h-12h。
2-丙烯酰胺-2-甲基丙磺酸(AMPS)：
2-丙烯酰胺-2-甲基丙磺酸甲酯(AMPSA)：
2-丙烯酰胺-2-甲基丙磺酸生成2-丙烯酰胺-2-甲基丙磺酸酯的机理：
堵漏剂的延迟机理：
合成可延迟吸水膨胀堵漏剂YD-1，合成可延迟吸水膨胀堵漏剂，其中亲水基团磺酸基以及羧基的羟基都已被烷氧基取代，形成疏水的磺酸酯和羧酸酯，因此在常温下清水中不吸水。而酯基在碱性、温度的条件下会发生水解反应，生成相应的酸钠盐，有吸水性。在井底能够提供水解需要的温度，且钻井液体系为碱性，所以这样我们就可以利用现场与井底的温度差实现酯基水解的快慢，从而控制堵漏剂吸水膨胀时间，达到延迟吸水膨胀的目的。
相对于现有技术，本发明所述的合成2-丙烯酰胺-2-甲基丙磺酸酯的方法具有以下优势：
本发明所述的合成2-丙烯酰胺-2-甲基丙磺酸酯的方法及应用，一步合成2-丙烯酰胺-2-甲基丙磺酸酯，条件温和，经济实惠，适合工业化生产，合成出的2-丙烯酰胺-2-甲基丙磺酸酯与其他组分配合，实现堵漏剂的可延迟膨胀，解决现有大多数凝胶吸水膨胀过快的缺点，在不损害原有膨胀倍数的情形下，达到延迟效果。
附图说明
图1为AMPSA的质谱图。
具体实施方式
下面结合实施例及附图1来详细说明本发明。
实施例1
将1mol的AMPS加入到10mol的原甲酸甲酯中，在100℃下反应12h，蒸馏多余的原甲酸甲酯，即得到产物合成2-丙烯酰胺-2-甲基丙磺酸甲酯。
2-丙烯酰胺-2-甲基丙磺酸甲酯的质谱图见附图1。
MS(ESI):m/z 222.1[M+H+]。2-丙烯酰胺-2-甲基丙磺酸甲酯的分子量是221.1，测的质谱的分子量是222.1，为2-丙烯酰胺-2-甲基丙磺酸甲酯加H+的分子量。
实施例2
将1mol的AMPS加入到10mol的原甲酸乙酯中，在100℃下反应12h，蒸馏多余的原甲酸乙酯，即得到产物合成2-丙烯酰胺-2-甲基丙磺酸乙酯。
制备出的2-丙烯酰胺-2-甲基丙磺酸乙酯经质谱图分析为该物质。
实施例3
将1mol的AMPS加入到10mol的原甲酸丙酯中，在100℃下反应12h，蒸馏多余的原甲酸丙酯，即得到产物合成2-丙烯酰胺-2-甲基丙磺酸丙酯。
制备出的2-丙烯酰胺-2-甲基丙磺酸丙酯经质谱图分析为该物质。
以上所述仅为本发明的较佳实施例而已，并不用以限制本发明，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 (4)

1.一种合成2-丙烯酰胺-2-甲基丙磺酸酯的方法，其特征在于：包括如下步骤：
将AMPS加入到原甲酸酯中，在70-100℃下反应1-12h，蒸馏多余的原甲酸酯，即得到产物2-丙烯酰胺-2-甲基丙磺酸酯，其中原甲酸酯的物质的量为AMPS物质的量的8～12倍，2-丙烯酰胺-2-甲基丙磺酸酯的结构式：
R＝甲基，乙基，丙基或丁基。
2.根据权利要求1所述的合成2-丙烯酰胺-2-甲基丙磺酸酯的方法，其特征在于：所述原甲酸酯为原甲酸三甲酯、原甲酸三乙酯、原甲酸三丙酯、原甲酸三丁酯中的任意一种。
3.根据权利要求1所述的合成2-丙烯酰胺-2-甲基丙磺酸酯的方法，其特征在于：反应温度为70-100℃。
4.一种权利要求1-3任一项所述的2-丙烯酰胺-2-甲基丙磺酸酯在制备新型可延迟膨胀类堵漏剂中的应用。
CN201711305929.5A 2017-12-11 2017-12-11 一种合成2-丙烯酰胺-2-甲基丙磺酸酯的方法及应用 Pending CN108047097A (zh)

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