Tridentate Titanium Complexes Catalyzed (Co)polymerization of 1-Butene★

doi:10.6023/A25050146

Acta Chimica Sinica ›› 2025, Vol. 83 ›› Issue (10): 1134-1141.DOI: 10.6023/A25050146 Previous Articles Next Articles

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三齿钛配合物催化的1-丁烯(共)聚合反应研究^★

王波^a, 朱光宇^b^,^c^,^d^,^*(), 徐广强^b^,^c^,^d, 王亮^b^,^c^,^d^,^*(), 侯鸿斌^b^,^c^,^d^,^*(), 张良^a^,^*(), 王庆刚^b^,^c^,^d

^a 西安建筑科技大学化学与化工学院西安 710055
^b 青岛新能源山东省实验室太阳能光电转换与利用重点实验室青岛 266101
^c 中国科学院青岛生物能源与过程研究所青岛 266101
^d 山东能源研究院青岛 266101

投稿日期:2025-05-08 发布日期:2025-06-20
通讯作者: 朱光宇, 王亮, 侯鸿斌, 张良
作者简介:
^★ “中国青年化学家”专辑.
基金资助:
山东省重大科技创新工程项目(2022CXGC020604); 山东省泰山学者奖励计划(tstp20240520); 山东省自然科学基金(ZR2023ME008); 山东省自然科学基金(ZR2023QB156)

Tridentate Titanium Complexes Catalyzed (Co)polymerization of 1-Butene^★

Bo Wang^a, Guangyu Zhu^b^,^c^,^d^,^*(), Guangqiang Xu^b^,^c^,^d, Liang Wang^b^,^c^,^d^,^*(), Hongbin Hou^b^,^c^,^d^,^*(), Liang Zhang^a^,^*(), Qinggang Wang^b^,^c^,^d

^a School of Chemistry and Chemical Engineering, Xi’an University of Architecture and Technology, Xi’an 710055
^b Key Laboratory of Photoelectric Conversion and Utilization of Solar Energy, Qingdao New Energy Shandong Laboratory, Qingdao 266101
^c Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao 266101
^d Shandong Energy Institute, Qingdao 266101

Received:2025-05-08 Published:2025-06-20
Contact: Guangyu Zhu, Liang Wang, Hongbin Hou, Liang Zhang
About author:
^★ For the VSI “Rising Stars in Chemistry”.
Supported by:
Major Science and Technology Innovation Program of Shandong Province(2022CXGC020604); Taishan Scholars Program of Shandong Province(tstp20240520); Natural Science Foundation of Shandong Province(ZR2023ME008); Natural Science Foundation of Shandong Province(ZR2023QB156)

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Abstract

Polyolefin materials occupy an important position in the national economy as indispensable basic materials for modern industry and daily life, representing the most extensively produced synthetic polymer materials globally. Transition metal catalysts are the significant driving factors for the development of the polyolefin industry, among which single-site non-metallocene transition metal catalysts have received widespread attention due to their simple synthesis and efficient linear polyolefin stereocontrol ability. Meanwhile, 1-butene, as a crucial byproduct of petrochemical industry, presents substantial research value for its high-value utilization. For example, current industrial circle employs heterogeneous Ziegler-Natta catalyst systems to produce isotactic poly(1-butene), which has found extensive applications in engineering fields such as hot water pipes. However, no other isotactic (mmmm<90%) poly(1-butene) materials have been reported for commercial applications. Based on the above background, we employed tridentate titanium complexes with quinoline side-arms to achieve efficient production of non-isotactic poly(1-butene) with good activity (over 10 kg•mmol⁻¹•h⁻¹), high M_n (up to 1800 kDa) and isotacticity of around 80% mmmm. Detailed methodological research (reaction temperature, catalyst concentration, etc.) was utilized to optimize polymerization activity and search for the rules of reaction conditions and results. Additionally, this work also achieved efficient copolymerization of 1-butene and 1-hexene with controllable monomer ratios. Both the resulting polymers and copolymers exhibited good material toughness. The breaking stress was close to 40 MPa and the elongation at break exceeded 800%. Wide-angle X-ray diffraction (WAXD) analysis showed that the crystal form of these polymers was form I or form I' without the transformation observed during the aging time, indicating superior stability compared to isotactic poly(1-butene) produced by Ziegler-Natta catalysts. When used as a filler, the obtained poly(1-butene)s significantly enhanced the toughness of natural rubber, demonstrating promising potential for rubber industry applications.

Key words: coordination polymerization, polyolefin, titanium complex, poly(1-butene), rubber-plastic blends

Cite this article

Bo Wang, Guangyu Zhu, Guangqiang Xu, Liang Wang, Hongbin Hou, Liang Zhang, Qinggang Wang. Tridentate Titanium Complexes Catalyzed (Co)polymerization of 1-Butene^★[J]. Acta Chimica Sinica, 2025, 83(10): 1134-1141.

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References 39

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Entry	Conditions^a	1-Butene/[Al]/[Ti]/[B] (mmol)	Yield (g) /conv. (%)	Activity/ (kg•mmol⁻¹•h⁻¹)	M_n^b/ kDa	PDI^b	Isotacticity^c (% mmmm)
1	Ti1/AlEt₃/[Ph₃C][B(C₆F₅)₄]/tol/25 ℃	86/0.25/0.01/0.01	2.24/47	2.69	27	3.1	82
2	Ti1/AlEt₃/B(C₆F₅)₃/tol/25 ℃	86/0.25/0.01/0.01	0.41/9	0.49	33	2.8	81
3^d	Ti1/AlEt₃/[Ph₃C][B(C₆F₅)₄]/DCM/25 ℃	86/0.25/0.01/0.01	1.30/27	1.56	27	2.8	80
4	Ti1/AlMe₃/[Ph₃C][B(C₆F₅)₄]/tol/25 ℃	86/0.25/0.01/0.01	n.p./0	n.r.	—	—	—
5	Ti1/AlⁱBu₃/[Ph₃C][B(C₆F₅)₄]/tol/25 ℃	86/0.25/0.01/0.01	2.43/51	2.92	216	3.3	83
6	Ti1/AlⁱBu₃/[Ph₃C][B(C₆F₅)₄]/tol/25 ℃	86/0.25/0.005/0.01	1.83/38	4.39	759	2.4	83
7	Ti1/AlⁱBu₃/[Ph₃C][B(C₆F₅)₄]/tol/25 ℃	86/0.25/0.0025/0.01	1.56/33	7.49	985	3.1	83
8	Ti1/AlⁱBu₃/[Ph₃C][B(C₆F₅)₄]/tol/25 ℃	86/0.25/0.00125/0.01	1.03/21	9.89	1884	1.9	80
9	Ti1/AlⁱBu₃/[Ph₃C][B(C₆F₅)₄]/tol/25 ℃	86/0.25/0.000625/0.01	0.17/4	3.26	952	2.9	84
10	Ti1/AlⁱBu₃/[Ph₃C][B(C₆F₅)₄]/tol/25 ℃	86/0.5/0.0025/0.01	2.57/54	12.34	744	2.6	83
11	Ti1/AlⁱBu₃/[Ph₃C][B(C₆F₅)₄]/tol/25 ℃	86/0.5/0.00125/0.01	0.76/16	7.30	1489	1.8	83
12	Ti1/AlⁱBu₃/[Ph₃C][B(C₆F₅)₄]/tol/25 ℃	86/1/0.0025/0.01	0.59/12	2.83	1062	2.2	84
13	Ti1/AlⁱBu₃/[Ph₃C][B(C₆F₅)₄]/tol/60 ℃	86/0.5/0.0025/0.01	2.13/44	10.22	448	3.9	82
14	Ti1/AlⁱBu₃/[Ph₃C][B(C₆F₅)₄]/tol/0 ℃	86/0.5/0.0025/0.01	3.15/66	15.12	857	1.8	84
15	Ti1/AlⁱBu₃/[Ph₃C][B(C₆F₅)₄]/tol/-20 ℃	86/0.5/0.0025/0.01	3.08/64	14.78	1459	1.9	81
16	Ti2/AlⁱBu₃/[Ph₃C][B(C₆F₅)₄]/tol/0 ℃	86/0.5/0.0025/0.01	2.26/47	10.85	1017	2.1	81
17^e	Ti3/AlⁱBu₃/[Ph₃C][B(C₆F₅)₄]/tol/0 ℃	86/0.5/0.0025/0.01	n.p./0	n.r.	—	—	—
18^e	Ti3/AlⁱBu₃/[Ph₃C][B(C₆F₅)₄]/tol/25 ℃	86/0.5/0.0025/0.01	n.p./0	n.r.	—	—	—

Entry	Conditions^a	1-Butene/[Al]/[Ti]/[B] (mmol)	Yield (g) /conv. (%)	Activity/ (kg•mmol⁻¹•h⁻¹)	M_n^b/ kDa	PDI^b	Isotacticity^c (% mmmm)
1	Ti1/AlEt₃/[Ph₃C][B(C₆F₅)₄]/tol/25 ℃	86/0.25/0.01/0.01	2.24/47	2.69	27	3.1	82
2	Ti1/AlEt₃/B(C₆F₅)₃/tol/25 ℃	86/0.25/0.01/0.01	0.41/9	0.49	33	2.8	81
3^d	Ti1/AlEt₃/[Ph₃C][B(C₆F₅)₄]/DCM/25 ℃	86/0.25/0.01/0.01	1.30/27	1.56	27	2.8	80
4	Ti1/AlMe₃/[Ph₃C][B(C₆F₅)₄]/tol/25 ℃	86/0.25/0.01/0.01	n.p./0	n.r.	—	—	—
5	Ti1/AlⁱBu₃/[Ph₃C][B(C₆F₅)₄]/tol/25 ℃	86/0.25/0.01/0.01	2.43/51	2.92	216	3.3	83
6	Ti1/AlⁱBu₃/[Ph₃C][B(C₆F₅)₄]/tol/25 ℃	86/0.25/0.005/0.01	1.83/38	4.39	759	2.4	83
7	Ti1/AlⁱBu₃/[Ph₃C][B(C₆F₅)₄]/tol/25 ℃	86/0.25/0.0025/0.01	1.56/33	7.49	985	3.1	83
8	Ti1/AlⁱBu₃/[Ph₃C][B(C₆F₅)₄]/tol/25 ℃	86/0.25/0.00125/0.01	1.03/21	9.89	1884	1.9	80
9	Ti1/AlⁱBu₃/[Ph₃C][B(C₆F₅)₄]/tol/25 ℃	86/0.25/0.000625/0.01	0.17/4	3.26	952	2.9	84
10	Ti1/AlⁱBu₃/[Ph₃C][B(C₆F₅)₄]/tol/25 ℃	86/0.5/0.0025/0.01	2.57/54	12.34	744	2.6	83
11	Ti1/AlⁱBu₃/[Ph₃C][B(C₆F₅)₄]/tol/25 ℃	86/0.5/0.00125/0.01	0.76/16	7.30	1489	1.8	83
12	Ti1/AlⁱBu₃/[Ph₃C][B(C₆F₅)₄]/tol/25 ℃	86/1/0.0025/0.01	0.59/12	2.83	1062	2.2	84
13	Ti1/AlⁱBu₃/[Ph₃C][B(C₆F₅)₄]/tol/60 ℃	86/0.5/0.0025/0.01	2.13/44	10.22	448	3.9	82
14	Ti1/AlⁱBu₃/[Ph₃C][B(C₆F₅)₄]/tol/0 ℃	86/0.5/0.0025/0.01	3.15/66	15.12	857	1.8	84
15	Ti1/AlⁱBu₃/[Ph₃C][B(C₆F₅)₄]/tol/-20 ℃	86/0.5/0.0025/0.01	3.08/64	14.78	1459	1.9	81
16	Ti2/AlⁱBu₃/[Ph₃C][B(C₆F₅)₄]/tol/0 ℃	86/0.5/0.0025/0.01	2.26/47	10.85	1017	2.1	81
17^e	Ti3/AlⁱBu₃/[Ph₃C][B(C₆F₅)₄]/tol/0 ℃	86/0.5/0.0025/0.01	n.p./0	n.r.	—	—	—
18^e	Ti3/AlⁱBu₃/[Ph₃C][B(C₆F₅)₄]/tol/25 ℃	86/0.5/0.0025/0.01	n.p./0	n.r.	—	—	—

Entry	Co-Monomer (mmol)	T/℃	Yield/g	Activity/ (kg•mmol⁻¹•h⁻¹)	M_n^b/ kDa	PDI^b	x/w ^c (%)
1	1-hexene (2)	0	2.06	9.89	1340	2.2	8/11
2	1-hexene (5)	0	2.41	11.57	1441	2.0	10/14
3	1-hexene (10)	0	2.20	10.56	1599	2.2	15/21
4	1-hexene (20)	0	2.13	10.22	1491	2.3	25/33
5	1-hexene (100)	0	3.95	18.96	2637	2.1	59/68
6	1-hexene (5)	-20	3.24	15.55	1454	2.1	7/10
7	1-hexene (5)	25	2.38	11.42	952	2.7	13/18
8	1-hexene (5)	60	1.99	9.55	849	3.5	15/21

Entry	Co-Monomer (mmol)	T/℃	Yield/g	Activity/ (kg•mmol⁻¹•h⁻¹)	M_n^b/ kDa	PDI^b	x/w ^c (%)
1	1-hexene (2)	0	2.06	9.89	1340	2.2	8/11
2	1-hexene (5)	0	2.41	11.57	1441	2.0	10/14
3	1-hexene (10)	0	2.20	10.56	1599	2.2	15/21
4	1-hexene (20)	0	2.13	10.22	1491	2.3	25/33
5	1-hexene (100)	0	3.95	18.96	2637	2.1	59/68
6	1-hexene (5)	-20	3.24	15.55	1454	2.1	7/10
7	1-hexene (5)	25	2.38	11.42	952	2.7	13/18
8	1-hexene (5)	60	1.99	9.55	849	3.5	15/21

三齿钛配合物催化的1-丁烯(共)聚合反应研究^★

Tridentate Titanium Complexes Catalyzed (Co)polymerization of 1-Butene^★

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三齿钛配合物催化的1-丁烯(共)聚合反应研究★

Tridentate Titanium Complexes Catalyzed (Co)polymerization of 1-Butene★

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三齿钛配合物催化的1-丁烯(共)聚合反应研究^★

Tridentate Titanium Complexes Catalyzed (Co)polymerization of 1-Butene^★