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MPV Reduction
1
MPV
Reduction
Introduction
The MPV Reduction involves using a specific aluminium catatlyst in the form of aluminium triisopropoxide to reduce ketones and aldehydes to their corresponding alcohols. The mechanism displays high chemoselectivity in its ability to produce primary and secondary alcohols.
1. Introduction
Aluminium triisopropoxide
Catalyst
Aluminium triisopropoxide
Catalyst
Cyclohexanone
Alcohol
History
Hans Meerwein
Born in Hamburg Germany, in 1879. Died in 1965.
Attained the position of Professor where he taught & researched at the university of Marburg, Germany.
2.
History
Collaborated with fellow chemist R. Schmidt, to discover the MPV reduction and then separately by A. Verley in 1925.
Recived the Otto Hahn Prize in Chemistry & Physics in 1959.
Public domain free of copyright
Also credited with the Wagner-Meerwein Rearrangement. This reaction was discovered by G. Wagner in 1899 and Hans Meerwein in 1914.
Mechanism
Aluminium triisopropoxide
Catalyst
3. Mechanism
Alcohol
Cyclohexanone
Aluminium triisopropoxide
Catalyst
Step 1:
Step 1:
Initial Stage:(Nucleophilic attack).
The attack comes from cyclohexanone, the carbonyl electrons draw towards the positive charge of aluminium triisopropoxide (because of a +3 charge, the catalyst can reduce 3 ketone species).
Step 2:
Step 2:
Intermediate Stage: (Rearrangement, Loss of a leaving group-Proton transfer)
The carbonyl electrons (green) move up to quench the positive charge (rearrangement), the aluminium removes the OCH(CH3)2 group (red), (loss of a leaving group), removing the negative charge. A ketone is created, the hydrogen on the ketone shifts to quench the positive charge left on it when the carbonyl double bond becomes a single bond (proton transfer).
Step 3:
Step 3:
Addition Of Acid: (Proton transfer, Loss of a leaving group).
Treatment with aqueous acid (H+) cleaves the aluminium-oxygen bond and produces cyclohexanol and regeneration of the catalyst(proton transfer and the loss of a leaving group).
Step 4:
Step 4:
Product Formation & Regeneration Of Catalyst:
Aluminium triisopropoxide Catalyst
Beauty & skin Care Industry
The aldehydes commonly used produce attractive aromas, colours and even flavours present in cosmetic products (carried out at high temperatures and under extreme conditions without huge losses of product).
4.
Beauty & skin Care Industry
This process is important in the information science industry as it may allow for greater synthesis of optically active carbonols to be formed at a high yield and under set conditions which may be altered for improvement in the future.
- Colognes
- Perfumes
- Make-Up
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jake-peterson (unsplash)
The Field of Medicine & Pharmacology
The MPV reduction can be used to convert acrolein (a compound which controls plant growth/life) into allyl alcohol which is often used as an important intermediate compound in the formation of a compound known as glycerol. Glycerol (a carbohydrate source) is often used to increase the levels of blood glucose in the body which may assist with the control of conditions like hypoglycaemia and diabetes mellitus (type 1).
5.
The Field of Medicine & Pharmacology
MPV reduction is also exceedingly crucial in creating products for polyester synthesis and explosive compounds.
The pharmaceutical industry utilizes the MPV reduction mechanism to assist with the bulk production of pharmaceuticals while reducing the cost, energy expenditure and time associated with the practice.
High chemoselectivity in the way MPV Reduction produces primary and secondary alcohols from aldehydes and ketones, enable the technology to be used in bulk production processes to be converted from a batch style production to continuous flow processes, this successfully reduced the use of a catalyst by 60% while increasing the product yield by an average of 10%.
References
Dimroth, Karl. (1967). "Hans Meerwein. 1879-1965". Chemische Berichte. 100(1): LV-XCIV.
(2016). A dictionary of chemistry (7 ed.). Oxford university press. ISBN-13: 9780198722823.
Dimroth, Karl. (1966). Hans Meerwein, the teacher and the man. Angewandte Chemie. Vol 5, Issue 4, pages 338-41.https://doi.org/10.1002/anie.196603381
Becker, H.; Berger, W.; Domschke, G.; Fanghänel, E. (1999): Organikum - Organisch Chemisches Praktikum. Wiley-VCH Verlag GmbH20, ISBN: 3527297197.
6. References
March, J. (1992): Advanced Organic Chemistry. Wiley-Interscience1, ISBN: 471581488
Fedtke, .; Prizkow, .; Zimmermann, . (1992): Technische Organische Chemie. Deutscher Verlag für Grundstoffindustrie1, ISBN: 3527309179.
Laue, T.; Plagens, A. (1998): Namen- und Schlagwort-Reaktionen der Organischen Chemie. Teubner3, ISBN: 3519235269.
Jones, M. (1997): Organic Chemistry. W.W.Norton Company1, ISBN: 0393970795.
Anikeev, Il’ina, Kurbakova, Salakhutdinov, Volcho, 2011. Meerwein–Ponndorf–Verley reduction of aldehydes formed in situ from α- and β-pinene epoxides in a supercritical fluid in the presence of alumina accessed from https://www.sciencedirect.com/science/article/pii/S1319610311001505/
Chemgaroo, 2018. Meerwein-Ponndorf-Verley Reduction accessed from http://www.chemgapedia.de/vsengine/vlu/vsc/en/ch/2/vlu/oxidation_reduktion/red_meerwein.vlu/Page/vsc/en/ch/2/oc/reaktionen/formale_systematik/oxidation_reduktion/reduktion/ersatz_o_n_durch_h/carbonsaeuren_und_derivate/meerwein_ponndorf/literatur.vscml.html/
Peterson, 2011. Transferring pharmaceutical batch technology to continuous flow accessed from https://smartech.gatech.edu/handle/1853/39510?show=full/