Catalysis in the production and reactions of dimethyl carbonate, an environmentally benign building block

Ono, Yoshio

doi:10.1016/s0926-860x(96)00402-4

Cited by 491 publications

(269 citation statements)

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“…1,2 So far, various approaches for DPC synthesis have been reported, including phosgene route, oxidative carbonylation of phenol and transesterification reaction. 1,[3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19] Among them, transesterification of dimethyl oxalate (DMO) with phenol to diphenyl oxalate (DPO), following a decarbonylation reaction, is an attractive and environmentally friendly route for the synthesis of DPC. [13][14][15][16][17][18][19] Liu et al 2255 Vol.…”

Section: Introductionmentioning

confidence: 99%

Comparative study on the catalytic properties of amino-functionalized silica materials for the transesterification of dimethyl oxalate with phenol

Liu¹,

Zhao²,

Zhu³

et al. 2010

J. Braz. Chem. Soc.

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Uma série de materiais híbridos mesoporos MCM-41, contendo diferentes grupos amino (como 3-aminopropila (AP-), (2-aminoetilamino)propila (AAP-), ou [2-(2-aminoetilamino) etilamino]propila (AEP-)) foi preparada pelo método de pós-enxertia e caracterizada por difração de raio X de pó (XRD), adsorção de N 2 , espectroscopia de infravermelho com transformada de Fourier (FT-IR) e dessorção de CO 2 com temperatura controlada (CO 2 -TPD). As propriedades catalíticas destes materiais híbridos para a reação de transesterificação de dimetil oxalato com fenol foram investigadas. Verificou-se que todos são ativos, particularmente o AEP-MCM-41, que apresentou a maior atividade dentre eles. Apenas um pequeno decréscimo na atividade foi observado após vários ensaios catalíticos sucessivos utilizando o mesmo catalisador, indicando uma boa reciclabilidade do mesmo. Notavelmente, a atividade do catalisador pode ser regenerado por simples tratamento com base, sob condições brandas. Além disso, os efeitos da densidade e da força básica dos grupos amino sobre as propriedades catalíticas foram exploradas na proposição do mecanismo de reação, incluindo a provável rota que leva à formação do subproduto anisol.A series of hybrid mesoporous MCM-41 materials containing different amino groups (such as 3-aminopropyl (AP-), (2-aminoethylamino)propyl (AAP-), or [2-(2-aminoethylamino)ethylamino] propyl (AEP-) group) were prepared by a post-grafting method, and characterized by means of X-ray powder diffraction (XRD), N 2 adsorption, Fourier transform-infrared spectroscopy (FT-IR) and temperature-programmed desorption of CO 2 (CO 2 -TPD). The catalytic properties of these hybrid materials were investigated for the transesterification of dimethyl oxalate with phenol. All the samples were active for the transesterification. Among them, the sample AEP-MCM-41 exhibited the highest activity under test conditions. And only a slight decrease in activity could be observed after few runs, indicating the good recyclability of this catalyst. Notably, the activity of the used catalyst could be regenerated by simple treatment with diluted basic agents under mild conditions. Moreover, effects of the density and the basic strength of the amino groups on the catalytic properties were taken into consideration for understanding the reaction mechanism and the possible formation route of the by-product anisole.Keywords: amino-functionalized, MCM-41, dimethyl oxalate, transesterification, recyclability IntroductionDiphenyl carbonate (DPC) is an industrially important intermediate for the production of several organic chemicals, especially as the precursor for the synthesis of polycarbonates (PCs), which have been used in many fields due to excellent mechanical, optical, electrical and heatresistance properties. 1,2 So far, various approaches for DPC synthesis have been reported, including phosgene route, oxidative carbonylation of phenol and transesterification reaction. 1,[3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19] Among them, transesterification...

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Section: Introductionmentioning

confidence: 99%

Comparative study on the catalytic properties of amino-functionalized silica materials for the transesterification of dimethyl oxalate with phenol

Liu¹,

Zhao²,

Zhu³

et al. 2010

J. Braz. Chem. Soc.

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“…DMC, a nonpolar aprotic solvent, is slightly soluble in water (139 g/L) [20] and miscible with alcohol, ester, ether, and ketone [21]. The chemical reactivity of DMC is versatile.…”

Section: Physico-chemical Properties Of Dmcmentioning

confidence: 99%

“…The most important properties of DMC are low toxicity and high biodegradability (>90% within 28 days) [18,21]. The oral acute toxicity (LD50) of DMC for rats is 13.8 g/kg, which indicates that it is a non-toxic compound.…”

Section: Physico-chemical Properties Of Dmcmentioning

confidence: 99%

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Environmentally-Benign Dimethyl Carbonate-Mediated Production of Chemicals and Biofuels from Renewable Bio-Oil

Kim

Lee

2017

Energies

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Due to the increasing emission of carbon dioxide (CO 2 ), the development of fuels and chemicals based on renewable resources has attracted much attention. Bio-oil, as a carbon rich material, has been considered as a feedstock for biodiesel production. In conventional methanol-mediated transesterification of bio-oil for biodiesel production, significant amounts of glycerol are being generated as a byproduct. In order to overcome these issues, dimethyl carbonate (DMC) has been recently used as an alternative acyl acceptor to avoid the generation of glycerol. DMC is an environmentally-benign chemical reagent and reactive solvent due to safety, health, and environmental benefits. Moreover, DMC can be produced from CO 2 . Co-production of biodiesel and chemicals such as glycerol carbonate is possible as the concept of zero-waste utilization of bio-oil. Value-added chemicals can be synthesized using DMC as a reagent. This paper provides a review on the physical and chemical properties of DMC as a solvent, as well as the production methods for DMC. DMC-mediated production of various chemicals and fuels in both chemical and enzymatic processes are discussed together with their pros and cons.

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“…In fact, DMC exhibits versatile chemical reactivity (Tundo, 1991;Ono, 1997). Depending on the experimental conditions, it may act as a methylating agent (Eq.…”

Section: Introductionmentioning

confidence: 99%

Dimethylcarbonate for eco-friendly methylation reactions

Memoli¹,

Selva

Tundo

2001

Chemosphere

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Dimethylcarbonate (DMC), an environmentally friendly substitute for dimethylsulfate and methyl halides in methylation reactions, is a very selective reagent. Both under gas±liquid phase transfer catalysis (GL-PTC) and under batch conditions, with potassium carbonate as the catalyst, the reactions of DMC with methylene-active compounds (arylacetonitriles and arylacetoesters, aroxyacetonitriles and methyl aroxyacetates, benzylaryl-and alkylarylsulphones) produce monomethylated derivatives, with a selectivity not previously observed (i.e., >99%). The highly selective O-methylation of phenols and p-cresols by DMC is also attained by a new methodology using a continuous fed stirred tank reactor (CSTR) ®lled with a catalytic bed of polyethyleneglycol (PEG) and potassium carbonate. Ó

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Catalysis in the production and reactions of dimethyl carbonate, an environmentally benign building block

Cited by 491 publications

References 38 publications

Comparative study on the catalytic properties of amino-functionalized silica materials for the transesterification of dimethyl oxalate with phenol

Comparative study on the catalytic properties of amino-functionalized silica materials for the transesterification of dimethyl oxalate with phenol

Environmentally-Benign Dimethyl Carbonate-Mediated Production of Chemicals and Biofuels from Renewable Bio-Oil

Dimethylcarbonate for eco-friendly methylation reactions

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