Dealkylation is the removal of alkyl groups from a compound, often done in the laboratory. Alkyls are hydrogen-carbon molecular structures, and their removal is important in organic chemistry and refining oil and pharmaceutical manufacturing. The process can occur naturally or through external chemicals, such as oxygen or nitrogen, and is used in mammalian metabolism research and clinical laboratories. Dealkylation is also important in the production of pharmaceuticals, fertilizers, and pesticides.
Dealkylation is a chemical process by which alkyl groups are removed from a given compound. It can be a bit difficult to define alkyls precisely without resorting to complicated chemical terms, but in general, alkyls are molecular structures made up of hydrogen and carbon, usually arranged in a circular pattern. Sometimes the removal of alkyls occurs naturally, usually as a result of sudden changes in temperature and decomposition processes, but more often it is manipulated in the laboratory by researchers or scientists. Alkyl removal is a common part of college-level organic chemistry studies, and these types of labs are thought to help students understand the various roles of hydrocarbon groups. There are a couple of reasons why the process is also beneficial outside of academic circles, perhaps most importantly when it comes to refining oil and petroleum and creating effective pharmaceuticals.
Understanding alkyls in general
Alkyds are a very general class of molecular components that contain a number of different hydrogen-carbon combinations. At its most basic level, an alkyl group is a functional group on an organic molecule that arises from an alkane that has lost a hydrogen atom, and are often broadly represented by the formula CnH2n+1. An alkane, by way of reference, is an organic molecule made up of straight or branched chains of carbon and hydrogen atoms where the carbon-carbon atoms are joined exclusively by single bonds.
Why and when it happens
There are always a variety of reasons why chemical reactions occur and alkyl groups falling into or out of compounds is no different. Temperature change, decomposition, and the addition of various external chemicals, either through intentional manipulation or natural consequences, are some of the most common methods of change. There are generally two main processes: the addition of oxides and oxygen-based compounds and the comparable addition of nitrogenous heavy chemicals. Both oxygen and nitrogen can bind to the hydrocarbon structures of some molecules in a way that rearranges their contents or causes shifts in existing bonds, but usually only when conditions are right.
Oxidative reactions
Most of these types of reactions in organic chemistry are viewed as the result of oxidative (O-) dealkylation. This process uses an oxide, a compound containing an oxygen atom and at least one other element, to extract the alkyl group of an organic molecule through some form of reduction-oxidation, or “redox” reaction. Through a change in the oxidative state of the carbon, the alkyl group breaks down.
O-dealkylation has become an important part of mammalian metabolism research. Specifically, this research addresses the human metabolism of pharmaceuticals and other foreign and chemical substances and the role that alkyl loss plays in that process. It also plays a significant role in the clinical laboratory, where it can be used to change the ability of a particular solution to donate electrons to other nearby particulates.
Nitrogen-based processes
Nitrogen-based alkyl shifts, often referred to in the literature as N-dealkylation reactions, are less common but generally just as effective. The addition of nitrogen can similarly cause a rearrangement of the hydrocarbon bond, but often takes much longer; the addition of nitrous compounds can and often also changes the overall nature of the compound in ways more profound than oxygen.
Role in petroleum refining and pharmaceutical manufacturing
Dealkylation is an important part of the process that turns crude oil into more usable products. Benzene and methylbenzene, for example, are both hydrocarbons found in crude oil, but benzene is more commercially valuable. When methylbenzene is mixed with hydrogen and a catalyst and heated to a particular temperature and under a specific amount of pressure, the methyl group is removed, producing benzene.
The process is also very important in the production of pharmaceutical products for both human and animal consumption. Removing alkyl groups can activate certain compounds in the creation of drugs and can also promote things like better absorption and efficacy. Similarly, the reaction is also often exploited by fertilizer and pesticide manufacturers.
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