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High steric-hindered amino-methano-phenol organic zinc compounds and process for preparing same

A technology of hindered aminomethylene phenol and a synthesis method, applied in the direction of zinc organic compounds and the like, can solve the problems of difficult preparation, price, poor selectivity, environmental problems and the like, and achieves the effects of mild reaction conditions, simple steps and good catalytic effect.

Inactive Publication Date: 2006-06-14
SHANXI UNIV
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  • Description
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  • Application Information

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Problems solved by technology

[0002] Carbon dioxide is inexhaustible, non-toxic and non-dangerous, and it is an abundant carbon resource that can be used; at the same time, a large amount of carbon dioxide emissions is the main factor leading to the greenhouse effect, causing serious environmental problems
However, the catalysts used so far have not been effectively applied either due to their low catalytic activity and poor selectivity, or due to their difficulty in preparation and price.

Method used

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  • High steric-hindered amino-methano-phenol organic zinc compounds and process for preparing same
  • High steric-hindered amino-methano-phenol organic zinc compounds and process for preparing same
  • High steric-hindered amino-methano-phenol organic zinc compounds and process for preparing same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] 实施例1:高位阻氨亚甲基酚有机锌化合物(I)的合成、表征及结构

[0017] 将1-甲基哌嗪(4.96g,50mmol),多聚甲醛(1.80g,60mmol)和2,4-叔丁基苯酚(10.32g,50mmol)溶于50mL乙醇中。在氮气保护下加热回流20小时,冷却至室温。加入氢溴酸(8mL,48%水溶液)得胶状物,将该胶状物真空干燥,乙醇洗涤得白色固体。将上述所得白色固体溶于水中,用碳酸氢钠中和后用氯仿(30mL×3)萃取,合并有机并有机相,真空除去溶剂得无色晶体状配体13.69克,产率86%。

[0018] 将二乙基锌(3.26mL,1M的Et 2 O溶液,3.26mmol)在-35℃搅拌下用注射器慢慢滴加到盛有上述配体(1.04g,3.26mmol)的乙醚(40mL)溶液中,反应液缓慢升至室温,再继续搅拌16 Hour. 过滤得到白色沉淀并用正己烷洗涤后溶入四氢呋喃和正己烷的混合溶剂中,真空浓缩,保存在-25℃12小时得无色晶体状目标化合物(I)1.55克,产率87%。

[0019] NMR data 1 H NMR(C 6 D. 6 ):δ(ppm)0.51(q,2H,CH 3 CH 2 ),1.30(t,3H,CH 3 CH 2 ),1.39(s,9H,CMe 3 ),1.45(s,9H,CMe 3 ), 1.97 (s, 3H, CH 3 ),2.08,2.16(br,4H,4H,N(CH 2 CH 2 ) 2 N),3.56(s,2H,Ar-CH 2 ),6.99(s,1H,Ar-H),7.54(s,1H,Ar-H); 13 C NMR:δ(ppm)3.43(CH 3 CH 2 ),13.02(CH 3 CH 2 ),29.78(CMe3),32.02(CMe 3 ),34.05(CMe 3 ),35.60(CMe 3 ),46.11(Me),53.88,55.20(N(CH 2 CH 2 ) 2 N),65.34,(Ar-CH 2 ),119.36,124.72,126.16,135.74,137.69,162.06(Ar)。

[0020] 元素分析:理论徝C,64.14;H,9.30;N,6.80;实测徝C,74.06;H,9.23;N,6.98。 ...

Embodiment 2

[0025] 实施例2:高位阻氨亚甲基酚有机锌化合物(II)的合成、表征及结构

[0026] 1-苯基哌嗪(8.11g,50mmol),多聚甲醛(1.80g,60mmol)和2,4-叔丁基苯酚(10.32g,50mmol)溶于50mL乙醇中。在氩气保护下加热回流20小时,冷却至室温。加入氢溴酸(8mL,48%水溶液)得胶状物,将该胶状物真空干燥,乙醇洗涤得白色固体。将上述所得白色固体溶于水中,用碳酸氢钠中和后用氯仿(30mL×3)萃取,合并有机相,真空除去溶剂得无色针状晶体状配体15.98克,产率84%。

[0027] 将二乙基锌(3.26mL,1M的Et 2 O溶液,3.26mmol)在-35℃搅拌下用注射器慢慢滴加到盛有上述配体(1.08g,3.26mmol)的乙醚(40mL)溶液中,反应液缓慢升至室温,再继续搅拌16 Hour. 过滤得到白色沉淀并用正己烷洗涤后溶入四氢呋喃和正己烷的混合溶剂中,真空浓缩,保存在-25℃12小时得无色晶体状目标化合物(II)1.30克,产率84%。

[0028] 核磁数据: 1 H NMR(C 6 D. 6 ):δ(ppm)0.47(q,2H,CH 3 CH 2 ),1.30(t,3H,CH 3 CH 2 ),1.40(s,9H,CMe 3 ),1.71(s,9H,CMe3 ), 2.58-3.00 (br, 8H, N (CH 2 CH 2 ) 2 N), 3.88(s, 2H, Ar-CH 2 ), 6.68(d, 2H, Ph-H), 6.81(t, 1H, Ph-H), 6.94(s, 1H, Ar-H), 7.14(t, 2H, Ph-H), 7.60(s, 1H, Ar-H); 13 C NMR: δ(ppm)3.43(CH 3 CH 2 ), 13.02 (CH 3 CH 2 ), 31.41 (CMe 3 ), 31.94 (CMe 3 ), 34.18 (CMe 3 ), 35.78 (CMe 3 ), 46.97, 47.86, 52.10, 54.41 (N(CH 2 CH 2 ) 2 N), 63.51 (Ar-CH 2 ), 116.43, 120.34, 125, 45, 127.12, 129.39, 138.96,...

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Abstract

A highly hindered aminomethylenephenol organozinc compound, its structural formula is: ∴ In the formula: R = alkyl or aryl, Bu t = tert-butyl; The compound is prepared by reacting organic ligands with diethyl zinc under mild conditions. The synthesis method can utilize basic chemical raw materials, has mild reaction conditions, simple steps and universal applicability. The compound has good catalytic effect on catalyzing the copolymerization of epoxide and carbon dioxide to prepare polycarbonate aliphatic ester.

Description

technical field [0001] 本发明涉及一种锌化合物及其合成方法,具体属于一种高位阻氨亚甲基酚有机锌化合物及其合成方法。 Background technique [0002] 二氧化碳取之不尽又无毒无危险性,是可以利用的、丰富的一碳资源;同时,二氧化碳的大量排放又是导致温室效应的主要因素,造成严重的环境问题。因此,有效地开发利用二氧化碳一直是人们关注的研究方向之一。1969年,Inoue等首次发现二氧化碳和环氧化合物共聚可生成脂肪族聚碳酸酯,这一过程直接由二氧化碳和环氧丙烷单体在二乙基锌 / 水催化剂催化在较温和的条件下共聚而不需要高能耗的还原反应生成高分子材料(S.Inoue,H.Koinuma,T.Tsuruta,J.polym.Sci.,Part B 1969,7,287)。该工作一经发表,立即引起了人们极大的研究兴趣。进一步的研究表明,聚碳酸亚丙酯具有较好的机械性能,其抗张强度和弹性模量均已超过了聚乙烯和聚丙烯,且聚碳酸亚丙酯具有生物降解特性,对人体无害而且环境友好,可广泛用于医疗、包装和工农业生产。但迄今为止所用的催化剂或者由于其催化活性偏低和选择性差、或者由于其难于制备和价格等问题,未能得到有效的应用。因此,开发和研究新的、高效的、易于制备的并且使反应能在更温和的条件下进行的催化剂体系成为当前研究的热点。 Contents of the invention [0003] 本发明的目的在于提供一种高位阻氨亚甲基酚有机锌化合物及其合成方法,该合成方法反应条件温和,步骤简单,能利用基本化工原料,该化合物对催化环氧化物与二氧化碳共聚制备聚碳酸脂肪族酯具有良好的催化效果。 [0004] 本发明所提供的高位阻氨亚甲基酚有机锌化合物,其化学结构式为: [0005] [0006] 式中:R=烷基或芳基,Bu t =叔丁基 [0007] 高位阻氨亚甲基酚有机锌化合物合成方法包括如下步骤: [0008] (1)按N-取代哌嗪∶多聚甲醛∶2,4-二叔丁基苯酚=1∶(1-2)∶1摩尔比加入到盛有相当于N-取代哌嗪摩尔量10-20倍的乙醇的反应器中,在氮气保护下加热回流15-25小时,冷却至室温,用相当于N-取代哌嗪摩尔量1-3倍的氢溴酸酸解,然后用碳酸氢钠中和后用氯仿萃取三次,合并有机相,真空除去...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F3/06
Inventor 魏学红刘滇生
Owner SHANXI UNIV
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