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Volumn 10, Issue 4, 2008, Pages 457-46

Green chemistry metrics: A comparative evaluation of dimethyl carbonate, methyl iodide, dimethyl sulfate and methanol as methylating agents

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EID: 41549109336     PISSN: 14639262     EISSN: 14639270     Source Type: Journal    
DOI: 10.1039/b713985c     Document Type: Article
Times cited : (194)

References (92)
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    • 2 fragment of DMC. Although, the reaction itself has a modest atom economy, the overall reaction efficiency should consider that the co-product ethylene glycol is also a highly valuable compound
    • 2 fragment of DMC. Although, the reaction itself has a modest atom economy, the overall reaction efficiency should consider that the co-product ethylene glycol is also a highly valuable compound.
  • 33
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    • Green Chemistry Theory and Practice, Oxford University Press
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    • Data were taken from: (a) ref. 4b; (b) MSDS on
    • Data were taken from: (a) ref. 4b; (b) MSDS on http://www.sigmaaldrich.com.
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    • Encyclopedia of Chemical Technology 3rd edn
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    • (1983) Kirk-Othmer , vol.22 , pp. 236-250
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    • 2 cycles), and heated at 160 °C, while the mixture was magnetically stirred. After 15 hours, the autoclave was cooled to room temperature, the solid base was removed by vacuum filtration, and the resulting solution stripped of residual MeOH/DMC by rotary evaporation to yield pure anisole in 92% yield
    • 2 cycles), and heated at 160 °C, while the mixture was magnetically stirred. After 15 hours, the autoclave was cooled to room temperature, the solid base was removed by vacuum filtration, and the resulting solution stripped of residual MeOH/DMC by rotary evaporation to yield pure anisole in 92% yield.
    • (1992) J. Chem. Soc. Perkin Trans. 2 , vol.4 , pp. 519-522
    • Selva, M.1    Trotta, F.2    Tundo, P.3
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    • 6 (ref. 14). Although this reaction modified the support, it had no effects on the overall methylation stoichiometry
    • 6 (ref. 14). Although this reaction modified the support, it had no effects on the overall methylation stoichiometry.
  • 56
    • 85032756480 scopus 로고    scopus 로고
    • As reported in ref. 3, the MI is expressed as the ratio of all raw materials [kg] to the product [kg]. From both environmental and synthetic standpoints, the lower the MI, the better the process is. In the ideal situation, MI would approach 1
    • As reported in ref. 3, the MI is expressed as the ratio of all raw materials [kg] to the product [kg]. From both environmental and synthetic standpoints, the lower the MI, the better the process is. In the ideal situation, MI would approach 1.
  • 57
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    • Stemming from the fact that water is an intrinsically safe solvent and it is often used in large amounts, some authors tend to exclude it from mass calculations to not skew mass data (see ref. 3). However, in the present study, water streams are highly polluted by toxic alkylating agents (DMS and MeI)
    • Stemming from the fact that water is an intrinsically safe solvent and it is often used in large amounts, some authors tend to exclude it from mass calculations to not skew mass data (see ref. 3). However, in the present study, water streams are highly polluted by toxic alkylating agents (DMS and MeI).
  • 58
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    • the c.-f. methylations mediated by DMC, a mixture of anisole and MeOH was collected at the outlet of both plug-flow and CSTR reactors. Only a final distillation step was necessary to recover the pure product
    • In the c.-f. methylations mediated by DMC, a mixture of anisole and MeOH was collected at the outlet of both plug-flow and CSTR reactors. Only a final distillation step was necessary to recover the pure product.
  • 60
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    • 3Me) of eqn (8), Scheme 5 were different than those of the corresponding reaction with phenol (eqn (1), Scheme 3)
    • 3Me) of eqn (8), Scheme 5 were different than those of the corresponding reaction with phenol (eqn (1), Scheme 3).
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    • 0525 506B1, May 01, and US Pat. 5278333, January 10, 1994
    • P. Tundo, P. Loosen, M. Selva, Eur. Pat. 0525 506B1, May 01, 1996 and US Pat. 5278333, January 10, 1994.
    • (1996) Eur. Pat.
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    • It is well known that, under phase-transfer catalysis conditions, the partitioning of PT-agents between an organic and an aqueous phase, does not allow the full recovery and restoration of the catalyst, after each reaction (see ref. 30)
    • It is well known that, under phase-transfer catalysis conditions, the partitioning of PT-agents between an organic and an aqueous phase, does not allow the full recovery and restoration of the catalyst, after each reaction (see ref. 30).
  • 83
    • 85032753417 scopus 로고    scopus 로고
    • 2 cycles, the mixture was magnetically stirred and heated at 90 C under nitrogen for 5 hours. After cooling to room temperature, the zeolite was removed by vacuum filtration, and the resulting solution stripped of residual DMC by rotary evaporation to yield pure product (2) in 93% yield
    • 2 cycles, the mixture was magnetically stirred and heated at 90 C under nitrogen for 5 hours. After cooling to room temperature, the zeolite was removed by vacuum filtration, and the resulting solution stripped of residual DMC by rotary evaporation to yield pure product (2) in 93% yield.
  • 89
    • 85032752849 scopus 로고    scopus 로고
    • 4. The release of both these acids should be expected to affect the catalytic activity of KF and zeolites (KX and NaX)
    • 4. The release of both these acids should be expected to affect the catalytic activity of KF and zeolites (KX and NaX).
  • 90
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    • Recycling of the feed was not mentioned by the authors of ref. 44 (process 27)
    • Recycling of the feed was not mentioned by the authors of ref. 44 (process 27).
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    • 85032767137 scopus 로고    scopus 로고
    • At high temperatures, batch reactions with MeOH proceed under high autogenous pressures. For instance, at 320 bar, a volume of 90 mL of methyl alcohol generates 60 bar of pressure (see ref. 9b). Therefore, c.-f. methods are always recommended with volatile alcohols, to avoid hazardous conditions
    • At high temperatures, batch reactions with MeOH proceed under high autogenous pressures. For instance, at 320 bar, a volume of 90 mL of methyl alcohol generates 60 bar of pressure (see ref. 9b). Therefore, c.-f. methods are always recommended with volatile alcohols, to avoid hazardous conditions.
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    • The formation of the toxic methanol as a co-product of DMC-mediated methylations (Scheme 3, 4 and 6), might somewhat mitigate the environmental benefits of DMC. Methanol is usually isolated (and disposed) by filtration/distillation, under conditions which are more controlled (and safer) than those used for the reactions. A thorough assessment of this problem should however, be carried out by toxicological metrics, not pertinent to this work
    • The formation of the toxic methanol as a co-product of DMC-mediated methylations (Scheme 3, 4 and 6), might somewhat mitigate the environmental benefits of DMC. Methanol is usually isolated (and disposed) by filtration/distillation, under conditions which are more controlled (and safer) than those used for the reactions. A thorough assessment of this problem should however, be carried out by toxicological metrics, not pertinent to this work.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.