Solvent-Free and Safe Process for the Quantitative Production of Phosgene from Triphosgene by Deactivated Imino-Based Catalysts

Abstract

Phosgene is quantitatively formed from solid triphosgene in a solvent-free and safe process without any reaction heat, catalyzed by planar N-heterocycles with deactivated imino functions. The rate of phosgene generation is adjustable to the rate of phosgene consumption in the subsequent phosgenation reaction by thermal control, catalyst concentration, and in some cases, specific properties of selected metal phthalocyanines. A thermal runaway reaction of this process is impossible.

Synergy Effects in the Chemical Synthesis and Extensions of Multicomponent Reactions (MCRs)—The Low Energy Way to Ultra-Short Syntheses of Tailor-Made Molecules

“…200 °C and catalyses according to a 6-element mechanism, because as is thermodynamically determined, ΔH = −243 J·g −1 . If the transformation is enabled at relatively lower temperatures of 80–120 °C, pure phosgene (pathway B ) is output in a reconversion without reaction heat, ΔH = +9 J·g −1 , if an appropriate catalyst is used that also blocks the 6-element mechanism [ 30 ].…”

“…There are reactions and processes in synthesis chemistry that run better with phosgene than with triphosgene, as i.e., the production of high-chem isocyanato-isocyanides for MCR chemistry in Section 9.2.6 [ 28 , 29 , 30 ]. This process was easily up-scaled to the 5 kg range and a phosgene generator was designed for a 30 kg·h −1 throughput [ 29 ].…”

Synergy Effects in the Chemical Synthesis and Extensions of Multicomponent Reactions (MCRs)—The Low Energy Way to Ultra-Short Syntheses of Tailor-Made Molecules

“…200 °C and catalyses according to a 6-element mechanism, because it is thermodynamically determined, Δ H = -243 J g -1 . If transformation is enabled at relatively lower temperatures of 80-120 °C, pure phosgene (pathway B) is output in a reconversion without reaction heat, Δ H = + 9 J g -1 , if an appropriate catalyst is used that also blocks the 6-element mechanism [30].…”

Discovery of biphenyl-aryl ureas as novel VEGFR-2 inhibitors. Part 4: Exploration of diverse hinge-binding fragments

“…17 Finally, intermediate (5) was treated with triphosgene (BTC) to produce various isocyanate, followed by reacting with substituted anilines yielding the title compounds (L1-L9). 18 Compound (8) chloride in triethylamine. The key intermediate (9) was prepared from (8) and (20) by Pd-catalyzed Suzuki coupling reaction.…”

“…17 Then, (9) was treated with triphosgene (BTC) to produce various isocyanate, followed by reacting with substituted anilines yielding the title compounds (W1-W12). 18 Compound (11) was synthesized from (10) by oxidizing reaction with KMnO 4 and acidification with hydrochloric acid. Subsequently, compound (11) was converted into (13) by reaction with thionyl chloride and methylamine.…”