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Methanol Conversions
Published in Saeed Sahebdelfar, Maryam Takht Ravanchi, Ashok Kumar Nadda, 1 Chemistry, 2022
Saeed Sahebdelfar, Maryam Takht Ravanchi, Ashok Kumar Nadda
The key reaction in Monsanto process is oxidative addition of methyl iodide (step 1) to planar square rhodium metallic center (I) to form hexagonal rhodium (III) species. The insertion of carbon monoxide (step 2) into cis-bond CH3-Rh produces a penta-coordinated acyl intermediate, which upon addition of carbon monoxide (step 3) and reductive elimination of acetyl iodide (step 4) regenerates the original rhodium (I) complex. Hydrolysis of acetyl iodide with water aqueous methanol feed produces acetic acid and HI that reacts with methanol to form methyl iodide and repeat its own cycle.
Thermochemistry, Electrochemistry, and Solution Chemistry
Published in W. M. Haynes, David R. Lide, Thomas J. Bruno, CRC Handbook of Chemistry and Physics, 2016
W. M. Haynes, David R. Lide, Thomas J. Bruno
Acenaphthene Acenaphthylene Acetaldehyde Acetamide Acetanilide Acetic acid Acetic anhydride Acetone Acetone cyanohydrin Acetonitrile Acetophenone Acetyl bromide Acetyl chloride Acetylene Acetyl fluoride Acetyl iodide 2-(Acetyloxy)benzoic acid 9-Acridinamine Acridine Acrolein Acrylamide Acrylic acid Acrylonitrile Actinium Adenine
Understanding oxidative addition in organometallics: a closer look
Published in Journal of Coordination Chemistry, 2022
Nabakrushna Behera, Sipun Sethi
In 1986, the British Petroleum (BP) Chemicals took over the Monsanto process, and in 1996, it emerged with a new as well as more effective commercial synthetic process for acetic acid known today as Cativa process [5, 53]. Fundamentally, it utilizes an iridium complex, [IrI2(CO)2]ā (49), as catalyst along with a metal-based iodide promoter, InI3 (Scheme 21). In contrast to the Rh-analogue, the in situ generated methyl iodide adds to 49 oxidatively almost 150 times faster. Subsequently, InI3 abstracts one Iā ligand from 50 to facilitate solvent coordination, after which the process is completed by coordination of CO, migratory insertion to build an acetyl group, and following reductive elimination of acetyl iodide, which upon hydrolysis gives acetic acid with restoration of HI. Various steps involved in the catalytic cycle are represented in Scheme 21.