新型侧链含可配位基团的半夹心三氯—茚钛、锆络合物的合成及其高选择性催化乙烯三聚的研究
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摘要
为了对侧链含可配位基团的三氯一茚钛络合物选择性催化乙烯三聚进行系统研究,本论文围绕这一主题共合成了32个化合物,其中包括17个为未见文献报道的新金属络合物以及相应的新型配体,新金属络合物包括9个侧链含苯环基的三氯一茚钛络合物,3个侧链含噻吩基的三氯一茚钛络合物,2个侧链含呋喃基的三氯一茚钛络合物及3个侧链含吡啶的三氯一茚锆络合物。新络合物均经1H NMR,13c NMR, EA等进行鉴定。另外C3, C5, C9, CS2, CN2进一步由单晶结构确定其结构。单晶结构显示：侧链苯环,噻吩在固体状态下并未与金属配位,而侧链吡啶中的N原子在固体状态下与金属配位。我们对所有金属络合物在助催化剂MAO作用下进行了乙烯齐聚反应及苯乙烯聚合反应的研究。
1.侧链含苯环基的茚钛络合物用于催化乙烯齐聚反应实验结果表明：本系列络合物可以有效催化乙烯选择性三聚,活性高于同一反应条件下对应的环戊二烯类钛络合物；本章合成的络合物中C3催化乙烯三聚效果最好,在0℃,Al:Ti=1000,0.8MPa乙烯压力下,生成1-己烯活性为1968Kg/(molTi-h),1-己烯选择性为95.9%.催化乙烯三聚活性受温度影响较大,低温下活性较高,升高温度活性迅速下降；金属络合物的结构对催化活性和选择性影响也较大,茚环与苯环之间的桥联过大或过小都会减少催化活性和选择性,另外侧链苯环上邻位的取代基对催化活性影响较大,选择性也下降很多。苯环对位上有取代基时催化活性有不同程度的减少,但相比邻位取代的络合物影响较小。
2.侧链含噻吩基的茚钛络合物用于催化乙烯齐聚反应实验结果表明：此类络合物也可以有效催化乙烯选择性三聚,其中CS2在本系列络合物中催化效果最好,在800C,Al:Ti=1000,0.5MPa乙烯压力下,生成1-己烯活性为697Kg/(molTi-h),1-己烯选择性为95%.本组催化剂催化乙烯聚合的重要特点在于耐温性好,在0-80℃间随温度升高,活性和选择性都得到提高,噻吩3位的位阻可极大抑制催化乙烯齐聚活性和选择性,而5位上适当的取代基可有效提高催化活性和选择性。
3.侧链含呋喃基的茚钛络合物用于催化乙烯齐聚反应实验结果表明：此类络合物在0-80℃,Al:Ti=1000,0.5MPa乙烯压力下不能有效催化乙烯齐聚,主要产物是聚合物。
4.侧链含吡啶基的茚锆络合物经催化乙烯聚合实验表明：此类络合物在0-800C,Al:Ti=1000-4000下,对乙烯聚合没有活性。
5.对上述络合物进行苯乙烯聚合研究表明,(1)侧链含苯环的的络合物催化苯乙烯聚合,活性最高达106g/(molTi-molSt-h),除C6和C7外,主要得到泡沫状无规聚苯乙烯,通过核磁鉴定属于富含间规的无规聚苯乙烯。(2)侧链含噻吩和呋喃的络合物催化苯乙烯聚合活性最高也可达106g/(molTi-molSt-h),但主要得到间规聚苯乙烯,呈白色细粉末状。(3)侧链含吡啶的茚锆络合物则对苯乙烯聚合没有活性。
In order to study systematically ethylene trimerization catalytzed by half-sandwich indenyl titanium complexes with pendant coorinated groups, thirty two compounds including seventeen new organometallic complexes were synthesized. These organometallic complexes include nine indenyl titanium complexes with pendant aryl, three indenyl titanium complexes with pendant thienyl, two indenyl titanium complexes with furyl and three indenyl zirconium complexes with pendant pyridyl. All the complexes are identified by1H NMR,13C NMR and elemental analysis. The structures of C3, C5, C9, CS2, CN2are further confirmed by X-ray crystal structure which show that the pendant aryl and thienyl don't coordinate with metal, while, the N atom in the pendent pyridyl coordinate with the metal in the solid state. All the complexes are tested for ethylene trimerization and styrene polymerization in the present of MAO.
1. The results of ethylene trimerization experiments catalyzed by indenyl complexes with pendent aryl show that this series of complexes can be effective for selective ethylene trimerization, and they are more active than corresponding cyclopendienyl complexes. C3in all of these series complexes is the most suitable catalyst for ethylene trimerization;1968Kg/(molTi-h) catalytic activity and95.9%selecticity for1-hexene are abtained at the condition of0℃, Al:Ti=1000,0.8MPa ethylene pressure. The reaction temperature has a great impact on the catalytic activity and high activity can be only getted at low temperature. The structure of the complexes can also influence the catalytic activity and selectivity. Too small or too big bridge carbon group between the indenyl ring and aryl can reduce the activity. Catalyst with the substituent on the ortho position of the pendent arene group can greatly dropped the activity, while substituents on the para-position of the arene group can also reduced the activity but not too much.
2. The results of ethylene trimerization experiments catalyzed by indenyl complexes with thienyl show that this series of complexes can also be effective for ethylene trimerization. Of all, CS2gives the best results;697Kg/(molTi-h) catalytic activity and95%selecticity for1-hexene can be abtained at the condition of80℃, Al:Ti=1000,0.5MPa ethylene pressure. An important catalytic feature of these series of complexes is temperature resistant. With the temperature increasing during0-80℃, the activity and selectivity is increasing graudually. The methyl on the3-position of thienyl has greatly reduced the catalytic activity, while, the suitable substituent on the5-position of the thienyl can prompt the activity.
3. The results of ethylene oligomerization experiments catalyzed by indenyl complexes with furyl show that this series of complexes can not catalyzed ethylene oligomerization effectively in the condition of0-80℃, Al:Ti=1000, and under0.5MPa ethylene pressure. The activity is extremely low and the main product is polymer.
4. The results of ethylene polymerization experiments catalyzed by indenyl zirconium complexes with pyridyl show that this series of complexes have no activity for ethylene polymerization and oligomerization in the condition of0-80℃and Al:Ti=1000-4000.
5. The results of styrene polymerization experiments catalyzed by all above complexes show that the complexes with ary, thienyl and furyl groups can catalyze styrene polymerization. The highest activity can reach106g/(molTi-molSt-h). when using the complexes with pendant aryl goups except C6and C7, a kind of bubble-like solid was getted. This kind of solid is usually soluble in the refluxed butanone, and actually it is "syndiotactic-rich atactic polystyrene" charactered by1H and13C NMR. While, the complexes with thienyl and furyl mainly get a kind of white powder solid, most of which is insoluble in the refluxed butanone, named s-PS. The zirconium complexes with pendant pyridyl gourp however, have no activity for styrene polymerization in the same condition as indenyl titanium complexes.
1.侧链含苯环基的茚钛络合物用于催化乙烯齐聚反应实验结果表明：本系列络合物可以有效催化乙烯选择性三聚,活性高于同一反应条件下对应的环戊二烯类钛络合物；本章合成的络合物中C3催化乙烯三聚效果最好,在0℃,Al:Ti=1000,0.8MPa乙烯压力下,生成1-己烯活性为1968Kg/(molTi-h),1-己烯选择性为95.9%.催化乙烯三聚活性受温度影响较大,低温下活性较高,升高温度活性迅速下降；金属络合物的结构对催化活性和选择性影响也较大,茚环与苯环之间的桥联过大或过小都会减少催化活性和选择性,另外侧链苯环上邻位的取代基对催化活性影响较大,选择性也下降很多。苯环对位上有取代基时催化活性有不同程度的减少,但相比邻位取代的络合物影响较小。
2.侧链含噻吩基的茚钛络合物用于催化乙烯齐聚反应实验结果表明：此类络合物也可以有效催化乙烯选择性三聚,其中CS2在本系列络合物中催化效果最好,在800C,Al:Ti=1000,0.5MPa乙烯压力下,生成1-己烯活性为697Kg/(molTi-h),1-己烯选择性为95%.本组催化剂催化乙烯聚合的重要特点在于耐温性好,在0-80℃间随温度升高,活性和选择性都得到提高,噻吩3位的位阻可极大抑制催化乙烯齐聚活性和选择性,而5位上适当的取代基可有效提高催化活性和选择性。
3.侧链含呋喃基的茚钛络合物用于催化乙烯齐聚反应实验结果表明：此类络合物在0-80℃,Al:Ti=1000,0.5MPa乙烯压力下不能有效催化乙烯齐聚,主要产物是聚合物。
4.侧链含吡啶基的茚锆络合物经催化乙烯聚合实验表明：此类络合物在0-800C,Al:Ti=1000-4000下,对乙烯聚合没有活性。
5.对上述络合物进行苯乙烯聚合研究表明,(1)侧链含苯环的的络合物催化苯乙烯聚合,活性最高达106g/(molTi-molSt-h),除C6和C7外,主要得到泡沫状无规聚苯乙烯,通过核磁鉴定属于富含间规的无规聚苯乙烯。(2)侧链含噻吩和呋喃的络合物催化苯乙烯聚合活性最高也可达106g/(molTi-molSt-h),但主要得到间规聚苯乙烯,呈白色细粉末状。(3)侧链含吡啶的茚锆络合物则对苯乙烯聚合没有活性。
In order to study systematically ethylene trimerization catalytzed by half-sandwich indenyl titanium complexes with pendant coorinated groups, thirty two compounds including seventeen new organometallic complexes were synthesized. These organometallic complexes include nine indenyl titanium complexes with pendant aryl, three indenyl titanium complexes with pendant thienyl, two indenyl titanium complexes with furyl and three indenyl zirconium complexes with pendant pyridyl. All the complexes are identified by1H NMR,13C NMR and elemental analysis. The structures of C3, C5, C9, CS2, CN2are further confirmed by X-ray crystal structure which show that the pendant aryl and thienyl don't coordinate with metal, while, the N atom in the pendent pyridyl coordinate with the metal in the solid state. All the complexes are tested for ethylene trimerization and styrene polymerization in the present of MAO.
1. The results of ethylene trimerization experiments catalyzed by indenyl complexes with pendent aryl show that this series of complexes can be effective for selective ethylene trimerization, and they are more active than corresponding cyclopendienyl complexes. C3in all of these series complexes is the most suitable catalyst for ethylene trimerization;1968Kg/(molTi-h) catalytic activity and95.9%selecticity for1-hexene are abtained at the condition of0℃, Al:Ti=1000,0.8MPa ethylene pressure. The reaction temperature has a great impact on the catalytic activity and high activity can be only getted at low temperature. The structure of the complexes can also influence the catalytic activity and selectivity. Too small or too big bridge carbon group between the indenyl ring and aryl can reduce the activity. Catalyst with the substituent on the ortho position of the pendent arene group can greatly dropped the activity, while substituents on the para-position of the arene group can also reduced the activity but not too much.
2. The results of ethylene trimerization experiments catalyzed by indenyl complexes with thienyl show that this series of complexes can also be effective for ethylene trimerization. Of all, CS2gives the best results;697Kg/(molTi-h) catalytic activity and95%selecticity for1-hexene can be abtained at the condition of80℃, Al:Ti=1000,0.5MPa ethylene pressure. An important catalytic feature of these series of complexes is temperature resistant. With the temperature increasing during0-80℃, the activity and selectivity is increasing graudually. The methyl on the3-position of thienyl has greatly reduced the catalytic activity, while, the suitable substituent on the5-position of the thienyl can prompt the activity.
3. The results of ethylene oligomerization experiments catalyzed by indenyl complexes with furyl show that this series of complexes can not catalyzed ethylene oligomerization effectively in the condition of0-80℃, Al:Ti=1000, and under0.5MPa ethylene pressure. The activity is extremely low and the main product is polymer.
4. The results of ethylene polymerization experiments catalyzed by indenyl zirconium complexes with pyridyl show that this series of complexes have no activity for ethylene polymerization and oligomerization in the condition of0-80℃and Al:Ti=1000-4000.
5. The results of styrene polymerization experiments catalyzed by all above complexes show that the complexes with ary, thienyl and furyl groups can catalyze styrene polymerization. The highest activity can reach106g/(molTi-molSt-h). when using the complexes with pendant aryl goups except C6and C7, a kind of bubble-like solid was getted. This kind of solid is usually soluble in the refluxed butanone, and actually it is "syndiotactic-rich atactic polystyrene" charactered by1H and13C NMR. While, the complexes with thienyl and furyl mainly get a kind of white powder solid, most of which is insoluble in the refluxed butanone, named s-PS. The zirconium complexes with pendant pyridyl gourp however, have no activity for styrene polymerization in the same condition as indenyl titanium complexes.
引文
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