TBD catalysis with dimethyl carbonate: a fruitful and sustainable alliance
Abstract
This work presents the synthesis of unsymmetric and symmetric organic carbonates as well as the synthesis of polycarbonates in an efficient and sustainable approach. All reactions were carried out at atmospheric pressure at 80 °C and the use of classic toxic and harmful chemicals, such as phosgene and carbon monoxide, was avoided. The key finding of this manuscript is that the use of 1,5,7-triazabicyclo[4.4.0]dec-5-ene, TBD, an organocatalyst, in combination with dimethyl carbonate (DMC), a non-toxic and renewable starting material, allows the synthesis of the mentioned unsymmetric carbonates in yields of up to 98% under optimized conditions. The structure of the alcohols used for this approach was found to influence the DMC–ROH ratio required to maximize the yield of the desired structure. Finally, the results obtained for the synthesis of low molecular weight building blocks could be transferred to the catalytic synthesis of high molecular weight polycarbonates.
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Several classes of organocatalysts have been used to catalyze the step-growth polymerization of diols with diacids or carbonates, including strong Brønsted acids and organic bases.
“Several classes of organocatalysts have been used to catalyze the SGP of diols with diacids or carbonates, including strong Brønsted acids such as H2SO4, triflic acid, p-toluenesulfonic acid (PTSA), bis(trifluoromethanesulfonyl)-imide (Tf2NH), 243,244 and organic bases such as TBD, 221,245-247 MTBD, 248 1-n-butyl-3-methylimidazol-2-carboxylate.249”
From Catalysis as an Enabling Science for Sustainable Polymers (2018) · cites this paper as [221]
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- Authors
- Mutlu, H., Ruiz, J., Solleder, S. C., & Meier, M. A. R.
- Affiliations
- Karlsruhe Institute of Technology (DE)
- Venue
- Green Chemistry
- Publisher
- Royal Society of Chemistry (RSC)
- Published
- 2012
- Volume
- 14
- Issue
- 6
- Pages
- 1728
- ISSN
- 1463-9262 (ISSN-L)
- 1463-9270
- OpenAlex
- W2059594175
- Cited by
- 116
- References
- 58
- Citations by year
- 2026: 4 · 2025: 7 · 2024: 4 · 2023: 7 · 2022: 7 · 2021: 7 · 2020: 4 · 2019: 12 · 2018: 12 · 2017: 11 · 2016: 8 · 2015: 7 · 2014: 11 · 2013: 12 · 2012: 3
- FWCI
- 5.06
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Green Chemistry (publishedVersion)
- Topics
- Physical Sciences › Chemical Engineering › Process Chemistry and Technology › Carbon dioxide utilization in catalysis
- Physical Sciences › Materials Science › Biomaterials › biodegradable polymer synthesis and properties
- Physical Sciences › Chemistry › Organic Chemistry › Chemical Synthesis and Reactions
- Keywords
- 1,5,7-triazabicyclo[4.4.0]dec-5-ene, dimethyl carbonate, organocatalysis, organic carbonates, polycarbonate, alcoholysis, green synthesis, green chemistry
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