CN105778076A - 一种聚醚胺化合物及制备方法和应用 - Google Patents
一种聚醚胺化合物及制备方法和应用 Download PDFInfo
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- -1 amine compound Chemical class 0.000 title claims abstract description 30
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 7
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- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
- C08G65/2609—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aliphatic hydroxyl groups
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Abstract
本发明提供了一种聚醚胺化合物,化学结构式如下:其中,n和m均选取为自然数1到20,R1、R2均选取为H、甲基、乙基、异丙基。本发明提供的这种聚醚胺化合物在气井修井作业过程中作为粘土稳定剂应用,适宜的聚合分子量和化合物官能团种类与数量保证了所制备化合物具有良好的粘土防膨率,有效克服了目前使用的部分离子型粘土稳定剂的在配伍性、耐酸碱等方面存在的问题。
Description
技术领域
本发明属于油气田开发技术领域,具体涉及一种聚醚胺化合物及制备方法和应用。
背景技术
在石油天然气的开采作业过程中,储集层的保护对油气田的持续生产和后期开发有着十分重要的意义。粘土稳定剂的应用是地层保护技术的重要组成部分,在钻井液、完井液、压井液、修井液等工作液中添加合适的粘土稳定剂能够有效降低由于粘土矿物的水化膨胀和分散运移引起的地层伤害,避免油气井产能下降甚至产能丧失。
常用的粘土稳定剂为无机盐类、阳离子表面活性剂、季铵盐表面活性剂、聚胺和聚季胺等。无机盐类粘土稳定剂优点是货源较广、价格便宜、后期处理方便,短期防膨效果甚好,缺点是长效性不足,只能暂时稳定粘土,地层外来流体中的某些阳离子容易取代无机盐发生离子交换,使无机盐浓度逐渐减小到一定程度时,此粘土稳定剂便失效;阳离子表面活性剂防膨效果优于各种无机盐类,吸引力强,长效性较好,耐冲刷能力强,但阳离子表面活性剂作为粘土稳定剂使用时,与钻井液中的多数阴离子处理剂的配伍性较差,对前置液和后置液要求高,容易不复配,发生反应,引起堵塞,而且能改变储层的润湿性,使储层由水润湿性变为油润湿性,对储层造成了一定的伤害;季铵盐类粘土稳定剂抗酸碱性差,尤其是TMAC和其他结构较复杂的烷基季铵盐均有毒性,对环境有一定的影响,在高固相钻井液中使用时,会产生较严重的絮凝现象;聚胺有效期短,费用高;聚季胺类相对分子量大,会加重对低渗透渗透率的伤害。
发明内容
本发明的目的是在现有粘土稳定剂的实际应用和工作基础上,研究开发一种新型低伤害粘土稳定剂,能够满足修井液中其他各种离子型组分的配伍需求,
为此,本发明提供了一种聚醚胺化合物,化学结构式如下:
其中,n为自然数1到20,m为自然数1到20,R1为H、甲基、乙基、异丙基中的一种,R2为H、甲基、乙基、异丙基中的一种。
本发明提供了聚醚胺化合物的制备方法,合成路线如下:
步骤一,丙二醇和环氧氯丙烷在碱及催化剂存在下发生聚合反应,得到中间产物A氯代聚醚化合物:
步骤二,氯代聚醚与胺催化胺化得到目标产物B聚醚胺化合物:
。
所述催化剂Ι为Ph3C+M(OC6F5)6 -或Y(OTf)3,其中M为Nb或Ta。
所述碱为氢化钠、氢化钙、乙醇钠、碳酸钠、碳酸氢钠、碳酸钾中的一种。
所述催化胺化反应中催化剂Ⅱ为RuH2(CO)(PPh3)3、Ru(COD)(COT)、RuH2(PPh3)4中的一种。
所述催化胺化反应中的胺为甲胺、二甲胺、乙胺、甲乙胺、异丙基胺或氨水中的一种。
所述聚合反应反应温度为80-150℃,反应时间为1-6h。
所述催化胺化反应温度为110-200℃,反应时间为1-10h,反应釜压力0.8-6MPa。
本发明还提供了聚醚胺化合物的应用,聚醚胺化合物用于粘土稳定剂。
本发明的有益效果是:本发明提供的这种聚醚胺化合物在气井修井作业过程中作为粘土稳定剂应用,适宜的聚合分子量和化合物官能团种类与数量保证了所制备化合物具有良好的粘土防膨率,目标产物B相对分子量最大不超过一千,保证聚合物属于低聚物,分子链的增长对于进入粘土间隙具有障碍作用。从而有效克服了目前使用的部分离子型粘土稳定剂的在配伍性、耐酸碱等方面存在的问题。
下面将结合附图做进一步详细说明。
附图说明
图1是本发明实施例1中目的产物B的红外光谱图;
图2是本发明实施例1中目的产物B的质谱图;
图3是本发明实施例2中目的产物B的红外光谱图;
图4是本发明实施例2中目的产物B的质谱图;
图5是本发明实施例3中目的产物B的红外光谱图;
图6是本发明实施例3中目的产物B的质谱图。
具体实施方式
本发明提供了一种聚醚胺化合物,化学结构式如下:
其中,n为自然数1到20,m为自然数1到20,R1为H、甲基、乙基、异丙基中的一种,R2为H、甲基、乙基、异丙基中的一种。
实施例1:
聚醚胺化合物合成路线如下:
步骤一,丙二醇和环氧氯丙烷在碱及催化剂存在下发生聚合反应,得到中间产物A氯代聚醚化合物:
步骤二,氯代聚醚与胺催化胺化得到目标产物B聚醚胺化合物:
。
步骤一和步骤二的反应分别属于催化聚合反应和多官能团转化反应,反应物反应比例实际完全取决于最终的聚合程度和官能团转化率,并非加入量,因此,为了不带来误解,在上述合成路线中没有给出反应物的摩尔比,而是通过以下实施例明确各物质质量的添加量来说明具体合成条件。
中间产物A的合成:
将6.08g的丙二醇、0.272g乙醇钠和0.100g催化剂ΙPh3C+Nb(OC6F5)6-加入100mL二口烧瓶,安装冷凝管和恒压滴液漏斗,并在恒压滴液漏斗内加入预先干燥的环氧氯丙烷55g,在磁力搅拌下,用SCHLENK方法除去装置体系中的氧气,并持续通入氮气保护。除氧完毕后,搅拌下油浴116℃加热,在此温度下将环氧氯丙烷滴入烧瓶,滴加完毕后,继续升温到130℃,反应2h后,用液氮冷却停止反应。过滤除去催化剂,所得淡黄色反应产物在减压下蒸出未完全反应的原料;最后得42g亮黄色液体产物,即为中间产物A。
本实施例中催化剂Ι为Ph3C+M(OC6F5)6 -,其中,Ph为苯基,M为Nb或Ta。碱为乙醇钠,SCHLENK方法也称无水无氧操作技术。
目的产物B的合成:
将19g中间产物A,2.0g催化剂ⅡRuH2(CO)(PPh3)3和20g甲胺加到100mL小钢瓶中,升温至130℃,0.8-1.5MPa下反应10h。所得产物除去催化剂Ⅱ后,使用装载有大孔树脂的玻璃柱进行分离纯化,旋蒸除去洗脱剂得到淡黄色液体,25g目标产物B。表征见附图1、图2。由图2可知,目标产物化合物B相对分子质量分子量为666。
其中,催化剂Ⅱ为一羰基二氢三(三苯基膦)合钌RuH2(CO)(PPh3)3,胺为甲胺,n为3,m为3,R1和R2均为CH3。
实施例2:
中间产物A的合成:
将6.08g的丙二醇、0.272g碳酸钠和0.100g催化剂ΙPh3C+M(OC6F5)6 -加入100mL二口烧瓶,安装冷凝管和恒压滴液漏斗,并在恒压滴液漏斗内加入预先干燥的环氧氯丙烷55g,在磁力搅拌下,用SCHLENK方法除去装置体系中的氧气,并持续通入氮气保护。除氧完毕后,搅拌下油浴85℃加热,在此温度下将环氧氯丙烷滴入烧瓶,滴加完毕后,继续升温到115℃,反应6h后,用液氮冷却停止反应。过滤除去催化剂,所得淡黄色反应产物在减压下蒸出未完全反应的原料;最后得12g亮黄色液体产物,即为中间产物A。
本实施例中催化剂Ι为Ph3C+M(OC6F5)6 -,碱为碳酸钠。
将19g中间产物A,1.5g催化剂ⅡRuH2(PPh3)4和40g氨水加到100mL小钢瓶中,升温至110℃,0.8-2.5MPa下反应8h。所得产物除去催化剂Ⅱ后,减压条件下蒸馏除去过量的氨水,得到微黄色聚醚胺粗产物。使用装载有大孔树脂的玻璃柱进行分离纯化,旋蒸除去洗脱剂得到20g微黄色目标产物化合物B。表征见附图3、图4。由图4可知,目标产物化合物B相对分子质量分子量为222。
其中,催化剂Ⅱ为二氢三(三苯基膦)合钌RuH2(PPh3)4,胺为氨水,n为1,m为1。R1和R2均为H。
实施例3:
中间产物A的合成:
将7.6g的丙二醇、0.353g碳酸钾和0.120g催化剂ΙY(OTf)3加入100mL二口烧瓶,安装冷凝管和恒压滴液漏斗,并在恒压滴液漏斗内加入预先干燥的环氧氯丙烷78g,在磁力搅拌下,用SCHLENK方法除去装置体系中的氧气,并持续通入氮气保护。除氧完毕后,搅拌下油浴100℃加热,在此温度下将环氧氯丙烷滴入烧瓶,滴加完毕后,继续升温到150℃,反应5h后,用液氮冷却停止反应。过滤除去催化剂,所得淡黄色反应产物在减压下蒸出未完全反应的原料;最后得65g亮黄色液体产物,即为中间产物A。
本实施例中催化剂Ι为Ph3C+M(OC6F5)6 -,碱为碳酸钾。
将19g中间产物A,2.0g催化剂ⅡRu(COD)(COT)和50g氨水加到100mL小钢瓶中,升温至180℃,2.0-2.5MPa下反应10h。所得产物除去催化剂Ⅱ后,减压条件下蒸馏除去过量的氨水,得到微黄色聚醚胺粗产物。使用装载有大孔树脂的玻璃柱进行分离纯化,旋蒸除去洗脱剂得到22g微黄色目标产物化合物B。表征见附图5、图6。相对分子质量761,n=m=4,R1和R2均为H。
其中,催化剂Ru(COD)(COT)为钌合物,其中COT指1,3,5-环辛三烯,COD指1,5-环辛二烯。
实施例4:
对实施例1合成的目标产物B进行粘土防膨率实验
将实施例1中合成的目标产物化合物B分别配成质量分数为0.3%、0.5%、1.0%、1.5%、2.0%、2.5%、3.0%的水溶液,按照行业标准SY/T5971-1994“注水用粘土稳定剂性能评价方法”防膨性能评价方法,测定其防膨率,结果如表1所示。
表1实施例1中目标产物B防膨率实验结果
浓度/% | 0.3 | 0.5 | 1.0 | 1.5 | 2.0 | 2.5 | 3.0 |
防膨率/% | 45.26 | 70.17 | 80.51 | 81.49 | 83.00 | 84.73 | 85.40 |
将实施例1中合成的目标产物化合物B和目前常用市售粘土稳定剂均配成质量分数为1%的溶液,平行测定其防膨率,结果见表2。
表2实施例1中目标产物B与市售粘土稳定剂的防膨率对照
粘土稳定剂 | 131# | 132# | KCl | Hop-2 | Hop-3 | 化合物B |
防膨率/% | 80.54 | 82.90 | 89.71 | 55.87 | 80.00 | 80.65 |
实施例5:
对实施例2合成的目标产物B进行粘土防膨率实验
将实施例2中合成的目标产物B分别配成质量分数为0.3%、0.5%、1.0%、1.5%、2.0%、2.5%、3.0%的水溶液,按照行业标准SY/T5971-1994“注水用粘土稳定剂性能评价方法”防膨性能评价方法,测定其防膨率,结果如表3所示。
表3实施例2中目标产物B防膨率实验结果
浓度/% | 0.3 | 0.5 | 1.0 | 1.5 | 2.0 | 2.5 | 3.0 |
防膨率/% | 37.10 | 76.34 | 84.13 | 85.05 | 91.27 | 93.15 | 93.48 |
将实施例2中目标产物B和目前常用市售粘土稳定剂均配成1%的溶液,平行测定其防膨率,结果见表4。
表4实施例2中目标产物B与市售粘土稳定剂的防膨率对照
粘土稳定剂 | 131# | 132# | KCl | Hop-2 | Hop-3 | 化合物B |
防膨率/% | 80.98 | 81.07 | 89.19 | 56.78 | 81.39 | 85.45 |
实施例6:
对实施例3合成的目标产物B进行粘土防膨率实验
将实施例3中合成的目标产物B分别配成质量分数为0.3%、0.5%、1.0%、1.5%、2.0%、2.5%、3.0%的水溶液,按照行业标准SY/T5971-1994“注水用粘土稳定剂性能评价方法”防膨性能评价方法,测定其防膨率,结果如表5所示。
表5实施例3中目标产物B防膨率实验结果
浓度/% | 0.3 | 0.5 | 1.0 | 1.5 | 2.0 | 2.5 | 3.0 |
防膨率/% | 40.77 | 73.09 | 86.83 | 88.24 | 90.40 | 94.79 | 96.82 |
将实施例3中目标产物B和目前常用市售粘土稳定剂均配成1%的溶液,平行测定其防膨率,结果见表6。
表6实施例3中目标产物B与市售粘土稳定剂的防膨率对照
粘土稳定剂 | 131# | 132# | KCl | Hop-2 | Hop-3 | 化合物B |
防膨率/% | 80.55 | 83.33 | 90.70 | 54.89 | 81.29 | 85.62 |
综上所述,本发明提供的这种聚醚胺化合物在气井修井作业过程中作为粘土稳定剂应用,适宜的聚合分子量和化合物官能团种类与数量保证了所制备化合物具有良好的粘土防膨率,目标产物B相对分子量最大不超过一千,保证聚合物属于低聚物,分子链的增长对于进入粘土间隙具有障碍作用。从而有效克服了目前使用的部分离子型粘土稳定剂的在配伍性、耐酸碱等方面存在的问题。
以上例举仅仅是对本发明的举例说明,并不构成对本发明的保护范围的限制,凡是与本发明相同或相似的设计均属于本发明的保护范围之内。
Claims (9)
1.一种聚醚胺化合物,其特征在于,化学结构式如下:
其中,n为自然数1到20,m为自然数1到20,R1为H、甲基、乙基、异丙基中的一种,R2为H、甲基、乙基、异丙基中的一种。
2.一种聚醚胺化合物的制备方法,其特征在于,合成路线如下:
步骤一,丙二醇和环氧氯丙烷在碱及催化剂存在下发生聚合反应,得到中间产物A氯代聚醚化合物:
步骤二,氯代聚醚与胺催化胺化得到目标产物B聚醚胺化合物:
。
3.根据权利要求2所述的一种聚醚胺化合物的制备方法,其特征在于:
所述催化剂Ι为Ph3C+M(OC6F5)6 -或三氟甲烷磺酸钇Y(OTf)3,其中,Ph为苯基,M为Nb或Ta。
4.根据权利要求2所述的一种聚醚胺化合物的制备方法,其特征在于:
所述碱为氢化钠、氢化钙、乙醇钠、碳酸钠、碳酸氢钠、碳酸钾中的一种。
5.根据权利要求2所述的一种聚醚胺化合物的制备方法,其特征在于:
所述催化胺化反应中的催化剂Ⅱ为RuH2(CO)(PPh3)3、Ru(COD)(COT)、RuH2(PPh3)4中的一种。
6.根据权利要求2所述的一种聚醚胺化合物的制备方法,其特征在于:所述催化胺化反应中的胺为甲胺、二甲胺、乙胺、甲乙胺、异丙基胺或氨水中的一种。
7.根据权利要求2所述的一种聚醚胺化合物的制备方法,其特征在于:所述聚合反应反应温度为80-150℃,反应时间为1-6h。
8.根据权利要求2所述的一种聚醚胺化合物的制备方法,其特征在于:所述催化胺化反应温度为110-200℃,反应时间为1-10h,反应釜压力0.8-6MPa。
9.根据权利要求1所述的一种聚醚胺化合物的应用,其特征在于:聚醚胺化合物用于粘土稳定剂。
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