油酸甲酯与乙烯复分解反应的研究进展

doi:10.3969/j.issn.1673-5854.2024.02.008

Abstract

Abstract:

The double decomposition reaction of methyl oleate and ethylene is a special kind of olefin double decomposition reaction. Two end-ene intermediates, 1-decene and 9-decene methyl ester, are obtained through the cross double decomposition products. At the same time, 9-octadecene and dimethyl-9-octadecene-1, 18-diate, are produced through competitive reactions. The selection of catalysts plays a decisive role in the rate and selectivity of this reaction. With the emergence of highly efficient and stable commercial ruthenium catalysts, the industrial application range of this reaction is gradually expanded. However, there are still some problems in the research of this reaction, such as incomplete process conditions, wide product distribution, expensive and difficult recovery of homogeneous catalysts, and poor activity of heterogeneous catalysts. In this paper, the mechanism of the double decomposition reaction between methyl oleate and ethylene is described in detail. With the development of catalysts as the axis, the research process of the reaction is introduced from the aspects of process conditions, types of catalysts and industrial application of products. The research progress of this reaction was systematically evaluated based on the conversion rate of methyl oleate, product yield and selectivity, and catalyst turnover number(TON). At the same time, it is suggested that in the future exploration, in addition to the development of catalyst, the whole reaction system should be optimized according to the actual conditions, so as to realize the integration of reaction, detection and separation.

Key words: methyl oleate, ethylene, olefin metathesis, ruthenium based catalyst, catalyst turnover

CLC Number:

TQ35
TK6

Jian CHENG, Shiwen LI, Zhanfang MA, Huayi LI. Research Progress in Double Decomposition Reaction of Methyl Oleate and Ethylene[J]. Biomass Chemical Engineering, 2024, 58(2): 64-72.

Figures/Tables 9

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Table 1

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References 64

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催化剂种类type of catalyst	温度/K temperature	乙烯压力/MPa ethylene pressure	反应时间/h reaction time	转化率/% conversion rate	选择性/% selectivity	产率/% productivity	TON值TON value	文献ref.
WCl₆-Me₄Sn	343	0.2	20	68	—	—	—	[30]
Re₂O₇-Al₂O₃-Me₄Sn	293	0.2	20	75	—	—	—	[30]
Mo(NAd)(CHCMe₂Ph)	—	0.4	15	95	99	95	4 750	[31]
WO(Ns)₂SiO₂	373	0.5	1	65	90	—	65	[34]
MTO/ZnAl₂O₄	318	1	5	52	—	58	4.7	[35]

催化剂种类type of catalyst	温度/K temperature	乙烯压力/MPa ethylene pressure	反应时间/h reaction time	转化率/% conversion rate	选择性/% selectivity	产率/% productivity	TON值TON value	文献ref.
Grubbs Ⅰ	303	0.4	3	80	100	—	2 980	[37]
Grubbs Ⅱ	313	0.2	2	94.9	100	94.9	—	[38]
Ru6	333	1	4	57	35	61	1 750	[39]
Ru7	303	1	0.5	42	83	35	26 000	[40]
Ru9	323	1	3	52	97	74	100 000	[43]
Ru10	323	1	3	73	97	74	3 125	[44]

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Research Progress in Double Decomposition Reaction of Methyl Oleate and Ethylene

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