What is dealkylation?

Dealkylation is used to create pharmaceuticals.

Dealkylation is a chemical process by which alkyl groups are removed from a particular compound. It can be a bit difficult to define alkyls precisely without resorting to complicated chemical terms, but in general they are molecular structures made up of hydrogen and carbon, often arranged in a circular fashion. Alkyl elimination sometimes occurs naturally, usually as a consequence of temperature changes and decomposition processes, but more often it is manipulated in a laboratory by researchers or scientists. Alkyl elimination is a common part of college level organic chemistry studies and these types of labs are believed to help students understand the various functions of hydrocarbon groups. There are a few reasons the process is advantageous outside of academic settings, perhaps most importantly when it comes to refining oil and petroleum and creating effective pharmaceuticals.

Understanding Alkyls in General

Alkyls are a very general class of molecular building blocks that contain many different combinations of hydrogen and carbon. At its most basic level, an alkyl group is a functional group on an organic molecule derived from an alkane that has lost a hydrogen atom and is usually broadly represented by the formula C n H 2n + 1 . An alkane, for reference, is an organic molecule composed of straight or branched chains of carbon and hydrogen atoms, where the carbon atoms are linked exclusively by single bonds.

why and when it happens

There are always a number of reasons chemical reactions occur, and the alkyl groups that enter or leave compounds are 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. In general, there are two main processes: the addition of oxides and oxygen-based compounds, and the comparable addition of heavy nitrogen chemicals. Both oxygen and nitrogen can bind to the hydrocarbon structures of certain molecules to rearrange the content or cause changes in existing bonds, but usually only when the conditions are right.

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oxidative reactions

Most of these types of reactions in organic chemistry are seen as a result of oxidative dealkylation (O-). This process uses an oxide, a compound that contains an oxygen atom and at least one other element, to remove the alkyl group from an organic molecule through some form of redox or reduction-oxidation reaction. Through a change in the oxidative state of carbon, the alkyl group splits off.

O-dealkylation has become an important part of mammalian metabolism research. Specifically, this research involves the human metabolism of pharmaceuticals and other foreign substances and chemicals and the role that alkyl loss plays in this process. It also plays an important role in the clinical laboratory, where it can be used to alter the ability of a specific solution to donate electrons to other nearby particles.

Nitrogen based processes

Nitrogen-based alkyl changes, often referred to in the literature as N-dealkylation reactions, are less common but generally just as effective. The addition of nitrogen can cause a hydrocarbon bond rearrangement, but it usually takes much longer; the addition of nitrous compounds can, and often does, change the overall nature of the compound in ways deeper than oxygen.

Role in petroleum refining and pharmaceutical production

Dealkylation is an important part of the process that converts crude oil into more usable products. Benzene and methylbenzene, for example, are hydrocarbons found in crude oil, but benzene has more commercial value. When methylbenzene is mixed with hydrogen and a catalyst, and heated to a certain temperature and under a certain pressure, the methyl group is removed and benzene is obtained.

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The process is also very important in the production of pharmaceutical products for human and animal consumption. The removal of alkyl groups can activate certain compounds in the creation of drugs and can also promote things like better absorption and efficacy. Along the same lines, fertilizer and pesticide manufacturers also often take advantage of the reaction.

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