Basic ionic liquids promoted chemical transformation of CO<sub>2</sub> to organic carbonates

Jiayin Hu; Huizhen Liu; Buxing Han

doi:10.1007/s11426-018-9396-3

SCIENCE CHINA Chemistry

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SCIENCE CHINA Chemistry, Volume 61, Issue 12: 1486-1493(2018) https://doi.org/10.1007/s11426-018-9396-3

Basic ionic liquids promoted chemical transformation of CO₂ to organic carbonates

Jiayin Hu^1,*, Huizhen Liu², Buxing Han^2,*

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ReceivedNov 27, 2018
AcceptedNov 28, 2018
PublishedDec 6, 2018

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Abstract

Ionic liquids (ILs), especially basic ILs with unique physicochemical properties, have wide application in catalysis. Using basic ILs as catalysts for the conversion of cheap, abundant, nontoxic, and renewable CO₂ into value-added organic carbonates is highly significant in view of environmental and economic issues. This review aims at giving a detailed overview on the recent advances on basic ILs promoted chemical transformation of CO₂ to cyclic and linear carbonates. The structures of various basic ILs, as well as the basic ILs promoted reactions for the transformation of CO₂ to organic carbonates are discussed in detail, including the reaction conditions, the yields of target products, the catalytic activities of basic ILs and the reaction mechanism.

Funded by

the National Key Research and Development Program of China(2018YFB0605801)

and the National Natural Science Foundation of China(21733011,21533011)

Acknowledgment

This work was supported by the National Key Research and Development Program of China (2018YFB0605801), and the National Natural Science Foundation of China (21733011, 21533011).

Interest statement

The authors declare that they have no conflict of interest.

References

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Figure 1
The structures of common basic ILs.
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Scheme 1
The common routes for synthesis of cyclic carbonates using CO₂.
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Figure 2
The structure of binary basic IL [APbim][Glu] [50].
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Scheme 2
The possible mechanism for the cycloaddition reaction of CO₂ with basic IL [P₄₄₄₄][2-OP] [45] (color online).
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Scheme 3
Preparation of the dual-IL system [TMGH][O₂MMIm][Br] [51].
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Figure 3
The structures of PDVB-HEIMBr [53] and Tri-s-triazine terminal-linked IL [54].
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Figure 4
Structures of the basic [N_114,6N₁₁]X ILs [66].
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Scheme 4
Proposed mechanism for the [TMGH][O₂MMIm][Br] promoted cycloaddition reaction of epoxides and CO₂ [51].
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Scheme 5
The mechanism of CO₂ incorporation into propargylic alcohols catalyzed by metal salt/base system [56].
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Scheme 6
The effect of different basic ILs on the synthesis of alkylidene carbonates from atmospheric CO₂ [58].
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Scheme 7
Basic [Bu₄P]₃[2,4-OPym-5-Ac] IL catalyzed CO₂ transformation to cyclic carbonates at ambient conditions [61] (color online).
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Scheme 8
Possible reaction pathway for the [Bu₄P]₃[2,4-OPym-5-Ac] IL catalyzed reaction of CO₂ and propargylic alcohol [61] (color online).
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Scheme 9
The common routes to synthesize linear carbonates using CO₂ (color online).
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Scheme 10
The mechanism for the basic [Bmim][OAc]/AgCl catalyzed reaction of CO₂ with propargylic alcohols and alcohols [57].

Table 1 Table 1 Summary of data for cycloaddition reactions between carbon dioxide and epoxides employing basic ILs catalysts

Entry	Basic ILs	Epoxide ^a)	Reaction conditions				Yield (%)	Ref.
Entry	Basic ILs	Epoxide ^a)	P (MPa)	T (°C)	t (h)	Solvent	Yield (%)	Ref.
1	[DBUH]₃[NbO₅]	PO	3	130	5	?	91.8 ^b)	[16]
2	[DMIm]₂[(Me₂PO₄)₂]	PO	3.5	100	1	?	94.4 ^b)	[17]
3	[DBUH][TA]	PO	3	60	8	?	99 ^b)	[39]
4	[P_8,8,8,1][AcO]	SO	0.1	100	23	?	75 ^b)	[40]
5	Ammonium betaine	PO	1	100	24	?	99 ^c)	[42]
6	Urea derivative based IL	PO	1.5	130	2	?	97 ^b)	[12]
7	[N₄₄₄₄][His]	PO	0.1	80	4.5	DMC	98 ^d)	[43]
8	[Bmim][ASP]	ECH	0.1	130	12	?	98 ^d)	[44]
9	[Bmim][Ala]	PO	4	130	18	?	96 ^b)	[21]
10	[P₄₄₄₄][2-O]	ECH	0.1	30	20	?	90 ^c)	[45]
11	His–MeI	SO	0.1	120	6	?	95 ^b)	[46]
12	[APbim]I	PO	1.5	120	1.5	?	94.3 ^b)	[34]
13	[DBU-CH₂CONH₂]Br	PO	2	120	3	?	99.2 ^b)	[33]
14	[TMGC₂H₄NH₂]Br	PO	2	130	3	?	94.6 ^b)	[47]
15	BrTBDPEG150TBDBr	PO	1	120	3	?	>99 ^b)	[35]
16	[DMAPH]Br	SO	0.1	120	4	?	96 ^c)	[48]
17	[APbim][Glu]	PO	0.5	105	13	?	93.4 ^b)	[50]
18	[TMGH][O₂MMIm][Cl]	ECH	0.5	30	20	?	>99 ^c)	[51]

a)PO=propylene oxide, SO=styrene oxide, ECH=epichlorohydrin; b) the yield was determined by GC; c) the yield was determined by NMR; d) isolated yield.

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