Scalable in situ diazomethane generation in continuous-flow reactors

Organic Process Research and Development

Volumn 16, Issue 5, 2012, Pages 1146-1149

  Rossi, Emiliano ^a   Woehl, Pierre ^b   Maggini, Michele ^a  

^a Corning European Technology Center ^*  (France)

^b UNIVERSITY OF PADOVA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL TRANSFORMATIONS; CONTINUOUS-FLOW; CONTINUOUS-FLOW REACTORS; DIAZOMETHANES; IN-SITU;

EID: 84862092033     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op200110a     Document Type: Article

References (23)

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7. See also Aldrich Technical Bulletin Al-180.
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15. www.sigmaaldrich.com/catalog/ProductDetail.do?lang=it&N4= D28000|ALDRICH&N5=SEARCH-CONCAT-PNO|BRAND-KEY&F=SPEC
16. The following statement is reported about diazomethane precursors: " although this material (Diazald) has been kept at room temperature for years without significant change, there has been reported one instance in which a sample stored for several months detonated spontaneously. For long periods of storage, it is recommended that the material be recrystallized and placed in a dark bottle ", in De Boer, T. J.; Backer, H. J.; Rabjohn, N., Ed. In Organic Synthesis; John Wiley & Sons: New York, 1963; Collect. Vol. IV, p 495.
17. www.sigmaaldrich.com/catalog/ProductDetail.do?lang=it&N4= N4766|SIGMA&N5=SEARCH-CONCAT-PNO|BRAND-KEY&F=SPEC
18. www.sigmaaldrich.com/catalog/ProductDetail.do?lang=it&N4= 05343|FLUKA&N5=SEARCH-CONCAT-PNO|BRAND-KEY&F=SPEC
19. 50 value is probably the reason why Diazald is usually preferred for diazomethane preparations. However it is reported that in a favorable environment (i.e. in the stomach) even a weakly or non-carcinogenic compound, such as Diazald, may give rise to strong carcinogenic products via trans-nitrosation reactions.
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21. www.unece.org/trans/danger/publi/adr/adr2011/11contentse.html. (ADR 2011, International Carriage of Dangerous Goods) Annex 1, part 1 (1.1.3.6.3 page 10). MNTS (ADR/RID: 3234, transport category 1, maximum quantity per transport unit: 20 kg); MNNG (ADR/RID: 1325, transport category 2, maximum quantity per transport unit: 333 kg); MNU (ADR/RID: 1325, transport category 3, maximum quantity per transport unit: 1000 kg).
22. Chevalier, B.; Lavric, E. D.; Cerato-Noyerie, C.; Horn, C. R.; Woehl, P. Chem. Today 2008, 26, 38-42
23. Lavric, E. D.; Woehl, P. Chem. Today 2009, 27, 45-48