CN114213468B - 一种金属铱配合物及其在增产胺合成中的应用 - Google Patents
一种金属铱配合物及其在增产胺合成中的应用 Download PDFInfo
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- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 12
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 10
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- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 19
- LQODJJDSWBDZMB-UHFFFAOYSA-N 2-(3,4-dichlorophenoxy)ethanol Chemical compound OCCOC1=CC=C(Cl)C(Cl)=C1 LQODJJDSWBDZMB-UHFFFAOYSA-N 0.000 claims description 12
- LOVYCUYJRWLTSU-UHFFFAOYSA-N 2-(3,4-dichlorophenoxy)-n,n-diethylethanamine Chemical compound CCN(CC)CCOC1=CC=C(Cl)C(Cl)=C1 LOVYCUYJRWLTSU-UHFFFAOYSA-N 0.000 claims description 10
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
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Abstract
本发明属于有机合成领域,涉及一种植物生长调节剂,尤其涉及一种金属铱配合物及其在增产胺合成中的应用。通过新型金属铱配合物催化一步合成新型植物生长调节剂增产胺,收率达到88%以上,反应过程水是唯一的副产物,环境污染小,易于实现工业化。该配合物的结构如下:
Description
技术领域
本发明属于有机合成领域,涉及一种植物生长调节剂,尤其涉及一种金属铱配合物及其在增产胺合成中的应用。
背景技术
增产胺,化学名2-(3,4-二氯苯氧)乙基二乙胺,是1977年Yokoyama等发现的一种植物生长调节剂。通过促进、增加或抑制、减少内源性植物激素的水平,显著地增强植物的光合作用,使用后叶片明显变绿、变厚、变大,增加对二氧化碳的吸收、利用率,增加蛋白质、酯类等物质的积累贮存,促进细胞分裂和生长。对于大豆、玉米、小麦、棉花、甜菜、人参银胶菊及多种蔬菜等作物具有不同程度的增产效果。能和多种农药肥料复配使用,增强植物的抗病能力,提高杀菌效果。增产胺以它独特的多功能作用,在农业上得到广泛应用。
目前增产胺的合成方法大多是以3,4-二氯苯酚为起始原料,主要有胺化法、烷基化一胺化法、酰胺还原法、环氧乙烷开环-磺酰基取代法和磺酰基取代改进法等5种方法。其中烷基化方法主要用二卤代烷和苯酚在非均相催化剂作用下合成卤素取代的乙氧基3,4-二氯苯酚,然后和二乙胺反应,反应时间长、而且反应过程产生大量含盐有机废水,难以处理。专利CN201610689161.5改为均相反应,在DMF溶剂下反应,提高了一定的效率。酰胺还原法需要四步完成反应,步骤较多,原料(四氢铝锂)价格较贵,成本高,后处理比较复杂,不适合工业化生产。环氧乙烷开环-磺酰基取代法和磺酰基取代改进法也存在副产较多,收率低的缺点。目前还需对其合成工艺进行改进。
发明内容
本发明旨在解决现有技术中制备增产胺污染大,收率低、成本高的问题,提供一种副产物少,环境污染小,易于实现工业化的其合成新方法;同时提供适于该反应的新型催化剂。
为了实现上述发明目的,本发明以新型金属铱配合物作为催化剂,通过催化反应一步合成增产胺,具体技术方案如下:
所述新型金属铱配合物的结构为:
1.该新型金属铱配合物的合成:氮气保护下,圆底烧瓶中加入[(ppy)2Ir(μ-Cl))2Ir(ppy)2]和乙腈,搅拌下加热,然后加入AgBF4的乙腈溶液,加热回流、冷却,过滤出固体,用乙醚洗涤,干燥后得到黄色粉末[Ir(ppy)2(MeCN)2]BF4;圆底烧瓶中加入[Ir(ppy)2(MeCN)2]BF4,配体1,3-二苯基咪唑,叔丁醇钾,四氢呋喃,氮气保护下加热回流,冷却后倒入水中,然后用乙醚萃取,无水硫酸镁干燥后蒸干,重结晶获得催化剂化合物1。
2.增产胺的合成:反应方程如下,压力容器中加入2-(3,4-二氯苯氧基)乙醇、二乙胺、上述催化剂,加热反应,反应结束后蒸出多余的二乙胺,减压蒸馏获得2-(3,4-二氯苯氧基)乙基二乙胺。
3.所述二乙胺的用量为2-(3,4-二氯苯氧基)乙醇的物质的量的3-4倍,催化剂用量为2-(3,4-二氯苯氧基)乙醇物质的量的0.01%-0.05%。反应时间8-24小时,反应温度为90-140℃,优选100-120℃。
本发明的有益效果:现有技术增产胺的制备方法产生大量废物,污染环境,本发明开发了金属铱配合物催化剂,一步合成增产胺,水是唯一的副产物,反应过程清洁,收率高,达88%以上。催化剂可以回收利用,且大大减少废物排放,环境友好,污染小,易于实现工业化。
具体实施方式
下面结合实施例对本发明作进一步地详细说明,但本发明的实施方式不限于此。
实施例1催化剂的合成
氮气保护下,圆底烧瓶中加入[(ppy)2Ir(μ-Cl))2Ir(ppy)2](195mg,0.18mmol)和20mL乙腈,搅拌下加热至40℃,然后加入AgBF4(71mg,0.36mmol)的乙腈(15mL)溶液,加热回流2小时、冷却,过滤出固体,用乙醚洗涤2次,干燥后得到黄色粉末[Ir(ppy)2(MeCN)2]BF4(231mg,93%).1H NMR(400MHz,CDCl3):δ9.02(d,2H),7.87-7.83(m,4H),7.48(d,2H),7.35(app t,2H),6.84(app t,2H),6.69(app t,2H),6.02(d,2H),2.30(s,6H).
100mL圆底烧瓶中加入[Ir(ppy)2(MeCN)2]BF4(335mg,0.5mmol),配体1,3-二苯基咪唑(330mg,1.5mmol),叔丁醇钾(168mg,1.5mmol),20mL四氢呋喃,氮气保护下加热回流24小时,冷却后倒入200mL水中,然后用乙醚萃取3次,无水硫酸镁干燥后蒸干,重结晶获得催化剂化合物1,288mg,收率80%。
1H NMR(400MHz,CDCl3):(ppm)δ8.12(d,J=5.5Hz,1H),7.97(d,J=5.6Hz,1H),7.76(d,J=8.1Hz,1H),7.66(d,J=8.1Hz,1H),7.62(d,J=1.8Hz,1H),7.55-7.52(m,2H),7.43-7.37(m,2H),7.28-7.25(m,1H),7.01-6.95(m,3H),6.87-6.82(m,6H),6.74-6.68(m,4H),6.57(t,J=7.2Hz,1H),6.30-6.27(m,2H),5.97(d,J=7.3Hz,1H).13C NMR(100MHz,CDCl3):(ppm)δ178.0,172.9,171.0,170.2,168.8,157.1,153.4,152.2,147.9,143.5,143.1,139.2,138.9,134.4,133.8,132.3,130.3,129.4,128.8,128.1,127.4,125.9,125.4,123.7,123.5,121.8,121.6,121.4,121.1,119.5,119.1,118.6,118.2,115.8,110.5.HRMS(ESI)m/z:[M+H]+Calcd for C37H28IrN 4721.1943;Found721.1943.
实施例2
在压力容器中加入2-(3,4-二氯苯氧基)乙醇(103g,0.5mol)、二乙胺(146g,2mol)、上述制得的催化剂(36mg,0.05mmol),密封后加热至120℃,反应12h,反应结束后蒸出多余的二乙胺,减压蒸馏获得2-(3,4-二氯苯氧基)乙基二乙胺120g,收率92%。
实施例3
在压力容器中加入2-(3,4-二氯苯氧基)乙醇(103g,0.5mol)、二乙胺(110g,1.5mol)、上述制得的催化剂(180mg,0.25mmol),密封后加热至90℃,反应24h,反应结束后蒸出多余的二乙胺,减压蒸馏获得2-(3,4-二氯苯氧基)乙基二乙胺115g,收率88%。
实施例4
在压力容器中加入2-(3,4-二氯苯氧基)乙醇(103g,0.5mol)、二乙胺(146g,2mol)、上述制得的催化剂(72mg,0.1mmol),密封后加热至140℃,反应8h,反应结束后蒸出多余的二乙胺,减压蒸馏获得2-(3,4-二氯苯氧基)乙基二乙胺123g,收率94%。
实施例5
在压力容器中加入2-(3,4-二氯苯氧基)乙醇(103g,0.5mol)、二乙胺(146g,2mol)、上述制得的催化剂(72mg,0.1mmol),密封后加热至100℃,反应10h,反应结束后蒸出多余的二乙胺,减压蒸馏获得2-(3,4-二氯苯氧基)乙基二乙胺122g,收率93%。
实施例6
在压力容器中加入2-(3,4-二氯苯氧基)乙醇(103g,0.5mol)、二乙胺(146g,2mol)、实施例5蒸馏后剩余物,密封后加热至100℃,反应10h,反应结束后蒸出多余的二乙胺,减压蒸馏获得2-(3,4-二氯苯氧基)乙基二乙胺120g,收率92%。
实施例7
在压力容器中加入2-(3,4-二氯苯氧基)乙醇(103g,0.5mol)、回收二乙胺(146g,2mol)、实施例6蒸馏后剩余物,密封后加热至100℃,反应10h,反应结束后蒸出多余的二乙胺,减压蒸馏获得2-(3,4-二氯苯氧基)乙基二乙胺122g,收率93%。
Claims (2)
1.分子结构式如下的金属铱配合物在增产胺合成中的应用,其特征在于,在压力容器中加入2 - ( 3,4-二氯苯氧基) 乙醇、二乙胺、金属铱配合物,加热反应,反应结束后蒸出多余的二乙胺,减压蒸馏获得2- (3,4-二氯苯氧基)乙基二乙胺;
。
2.如权利要求1所述的金属铱配合物在增产胺合成中的应用,其特征在于,二乙胺的用量为2 - ( 3, 4-二氯苯氧基) 乙醇的物质的量的3-4倍,金属铱配合物用量为2 - ( 3,4-二氯苯氧基) 乙醇物质的量的0.01%-0.05%,反应时间8-24小时,反应温度为90-140 oC。
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH02164801A (ja) * | 1988-12-19 | 1990-06-25 | Nitto Baion Kk | 花芽増加・開花促進方法 |
CN1284497A (zh) * | 2000-08-08 | 2001-02-21 | 陈熹 | 3、4二氯苯氧基乙基二乙胺制造工艺 |
CN101087863A (zh) * | 2004-12-23 | 2007-12-12 | 西巴特殊化学品控股有限公司 | 具有亲核卡宾配体的电致发光金属络合物 |
CN106278914A (zh) * | 2016-08-19 | 2017-01-04 | 四川福思达生物技术开发有限责任公司 | 一种增产胺的合成工艺 |
CN106748822A (zh) * | 2017-01-22 | 2017-05-31 | 天津市绿亨化工有限公司 | 增产胺的新合成方法 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20140131665A1 (en) * | 2012-11-12 | 2014-05-15 | Universal Display Corporation | Organic Electroluminescent Device With Delayed Fluorescence |
US9209411B2 (en) * | 2012-12-07 | 2015-12-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9929360B2 (en) * | 2016-07-08 | 2018-03-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
-
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- 2022-01-11 CN CN202210027226.5A patent/CN114213468B/zh active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH02164801A (ja) * | 1988-12-19 | 1990-06-25 | Nitto Baion Kk | 花芽増加・開花促進方法 |
CN1284497A (zh) * | 2000-08-08 | 2001-02-21 | 陈熹 | 3、4二氯苯氧基乙基二乙胺制造工艺 |
CN101087863A (zh) * | 2004-12-23 | 2007-12-12 | 西巴特殊化学品控股有限公司 | 具有亲核卡宾配体的电致发光金属络合物 |
CN106278914A (zh) * | 2016-08-19 | 2017-01-04 | 四川福思达生物技术开发有限责任公司 | 一种增产胺的合成工艺 |
CN106748822A (zh) * | 2017-01-22 | 2017-05-31 | 天津市绿亨化工有限公司 | 增产胺的新合成方法 |
Non-Patent Citations (1)
Title |
---|
"增产胺的合成与应用研究进展";尤洪星 等;《山东化工》;第44卷(第20期);第43-45, 47页 * |
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