Research question
Is it possible to remove alcohol from the body, prior to intoxication, using esterification and what importance will this have on society?
What is in alcoholic beverages
Alcohols are organic compounds consisting of a hydroxyl functional group (OH) attached to an alkyl group (e.g. R-OH). The general formula for alcohols is CnH2n+1OH.
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Ethanol is the primary alcohol present in alcoholic beverages, therefore being the most likely to cause alcohol intoxication. It has the molecular formula C2H5OH and according to the National Pollutant Inventory is considered a “volatile organic compound”, with a melting point of -144 degrees Celsius and a boiling point of 78.5 degrees Celsius. Additionally, alcohol is a great solvent and readily dissolves into water.
Ethanol is present in almost all alcoholic beverages however in different concentrations. Some examples of average alcohol concentrations in different beverages include:
- • Regular beer – 4.8% alcohol content
- • Wine – 13.5% alcohol content
- • Whiskey – 40% alcohol content
What is intoxication
When alcoholic beverages are consumed, they often cause intoxication, a mild form of ethanol poisoning. according to the Australian Government Department of Health, intoxication refers to “any change in perception, mood, thinking processes and motor skills that results from the effect of a drug on our central nervous system.” When someone undergoes such changes they are often referred to being in a drunken state.
Ethanol causes intoxication primarily through its property to easily dissolve in water. Ethanol has both a polar side[OH] (which is caused because the oxygen is much more electro negative than the hydrogen and so pulls most of the electrons towards it, giving it a partial negative charge while the hydrogen gets a partial positive charge) and a non-polar side [C2H5]. However, the polar side OH, gives ethanol the ability to form hydrogen bonds with water which is also polar (following the rule “like dissolves like”). This is only possible because the carbon chain attached to the functional group is fairly small consisting of only 2 carbons, which means that the non-polar side of the molecule is small allowing the polar side to dissolve. This differs in other alcohols with larger carbon chains (non-polar sides) such as decanol which is insoluble because its carbon chain is so much longer. Ethanol is therefore described to be miscible in water (very soluble).
When ethanol gets consumed and enters the body it dissolves into water. It then gets transported through the digestive system, where approximately 20% enters the bloodstream through the stomach and 80% through the small intestine. Then it gets transported to all organs of the body through the water it has dissolved in including, but not limited to the lungs (which is why breathalysers work), heart and brain. This can happen within 30min to 2hours, depending on a range of factors such as age, weight, gender, whether consumed after food, etc.
Once the ethanol gets transported to the brain it begins activating or suppressing receptors in your brain. This includes suppressing the glutamate, a neurotransmitter which excites neurons, causing the brain to respond slower; and activating the gamma aminobutyric acid which causes drowsiness and extreme feelings of ‘calm’. By ethanol suppressing and activating these types of brain receptors, it increases a person’s felling of drowsiness and calmness and slows brain activity in general, which is what become known as symptoms of intoxication and gives alcohol the classification as a central nervous system depressant drug.
Intoxications effect on society
Today alcohol can be seen as a part of Australian culture and it is not uncommon for it to be consumed on a regular basis for recreation making it one of the most used social drugs in Australia. in fact, according to the Australian Institute of Health and Welfare, 9.7liters of pure alcohol was consumed per person in 2015-16 alone. intoxication however has been shown to have a vast array of very prevalent and urgent societal issues.
One such issue includes the issues associated with drinking whilst under the influence of alcohol. Because alcohol acts as a nervous system depressant drug is slows brain activity causing decreased ability to process and respond to situation and well as limiting the ability to think clearly. Additionally, intoxication can result in drowsiness loss of consciousness, becoming les alert, impaired hand eye coordination and many other effects which greatly hinders someone’s ability to drive. As result many accident, injuries and deaths are cause when driving whilst intoxicated/under the influence of alcohol. According to “Impact of alcohol and illicit drug use on the burden of disease and injury in Australia: Australian Burden of Disease Study 2011” one third of all roads traffic injuries are a direct result of driving whilst under the influence of alcohol. To respond to this the government has criminalised driving whilst intoxicated and has increased fines and penalties so as to further impose this law and encourage compliance. However, there are still many who continue to drive whilst intoxicated, causing many fatalities, injuries and accidents in general, which ultimately has a negative effect on society and those involved (particularly those who may be injured/killed because of someone else drink driving).
Moreover, intoxication in the short term has been shown to increase risky behaviours. The NDSHS showed that, in 2016 almost 1 in 6 (17%) recent drinkers aged 14 and over put themselves or others at risk of harm while under the influence of alcohol in the previous 12 months. This also includes an increase in criminal activity which as seen in the Australian Bureau of Statistics crime victimisation survey “almost 3 in 5 people aged 18 years and over who experienced physical assault or face-to-face threatened assault in the last 12 months believed that alcohol and any other substance contributed to their most recent incident”. The Australian Institute of Criminology’s (AIC) National Homicide Monitoring Program presented statistics showing in 39% of homicide incidents either the victim or offender had consumed alcohol and 8% of homicides were motivated by an alcohol-related argument. Furthermore, the 2016 Personal Safety Survey showed that half of the women who had experienced physical or sexual violence in the past 10 years, reported that they believed alcohol or another substance contributed. This has a negative effect on society as the intoxicated person places not only themselves in danger but those around them too.
Intoxication has also been shown to be detrimental to people’s health. Statistics from the ABS show that There were 1,366 registered alcohol-induced deaths in 2017 and an additional 2,820 deaths where alcohol was mentioned as a contributory cause of death. Additionally, alcohol has been contributed to 4.6% of the total burden of disease in Australia in 2011 and was also responsible for 40% of the burden of liver cancer and 37% of the burden of mouth and pharyngeal cancer. moreover, according to the 2016 National Drug Strategy Household Survey 2.8% had been injured while under the influence of alcohol and required medical attention. These statistics show the negative effects intoxication has on health.
As a result of such societal issues caused by intoxication, it is evident that a means to prevent intoxication when alcohol has been consumed would have an extremely positive effect on society. it would allow a means for alcohol to be consumed and not hinder the Australian “way of life”, whilst also limiting intoxication. In this way issues such as driving under the influence, increased risky and criminal behaviour and severe health issues, can be minimised and prevented and overall improve society.
Esterification
Esterification refers to a reaction between an alcohol and carboxylic acid, catalysed by an acid, to produce an ester as well as water. Generally following the following formula:
R-OH + R-C-OH ⇌ R-C=O + H-O-H
O [ H+ ] O-R’
Alcohol + carboxylic acid ⇌ Ester + water
As mentioned previously the alcohol that is consumed is primarily ethanol, as such that is what will be used in the following equations. Additionally, the acid catalyst that will be used will be HCl. This is because HCl as well as KCl and NaCl are the primary components which make up gastric acid (acid formed in the stomach for the digestion of proteins/food) and so are already present in the body even before the alcohol is consumed. Therefore, the only necessary addition to the body apart from the alcohol will be the carboxylic acid in this case ethanoic acid [aka acetic acid].
The esterification reaction works in approximately 5 steps as follows:
- Protonation of the carbonyl acid using the catalyst- This step involves protonating the double bonded oxygen in the acetic acid by taking the proton(H+) from the HCl, therefore giving the oxygen a positive charge. This process is formally known as protonation and is necessary as it makes the carbonyl more electrophilic, meaning that it can more easily attract electrons (this will be necessary in the following steps).
- Nucleophilic attack- a nucleophilic attack involves a nucleophile (i.e. a molecule which has at least one pair of free electrons, that donates them to form a chemical bond) “attacking” an electrophile (positively charged atom). In this case the nucleophile will be the oxygen in the ethanol which has two pairs of free electrons. One pair of these electrons will attack the 1st carbon in the carbonyl creating a bond between them. This causes one pair of the electrons in the double bond between carbon and oxygen to shift to the oxygen, thus resulting in the double bond becoming a single bond and the oxygen having four free electrons. Additionally, the oxygen which was just acting as the nucleophile becomes positively charged.
- Proton transfer- This step involves transferring the proton[H] from the just previously bonded alcohol to the OH group. It is done in two steps:
- Deprotonation- this involves having another alcohol molecule act as a base (proton acceptor) and the carbonyl acting as an acid (proton donor). The alcohol in this steps accepts the H+ from the carbonyl.
- Protonation- after deprotonation the positively charged alcohol then acts as a proton donor/acid, transferring the H+ onto the OH group in the carbonyl. This additionally makes the O positively charged
- H2O leaves the molecule- in order for the water to leave the electrons in its bond to carbon need to shift on to the oxygen. For this to happen one pair of free electrons form the O in the OH group need to reform a double bond with the carbon. This will therefore push the extra electrons onto the H2O molecule (a very good leaving group), thus creating one of the products of the final reaction. Additionally, the oxygen in the OH group becomes positively charged.
- Deprotonation- this is the final step where the proton [H+] is removed. The Cl- produced from step one acts as a base accepting the extra proton to reform HCl. The pair of electrons originally bonding the OH is shifted to the O creating the final product ethyl ethanoate
The simplified version of this reaction that would occur within the body will look like the following:
Ethanol + Ethanoic acid [catalyst: HCl] ⇌ Ethyl ethanoate + water
⇌
Problems associated with esterification for prevention of intoxication
Esterification however has many flaws when being used to remove alcohol from the body prior to intoxication. One of the most pressing issues would be the time it takes for esterification to naturally occur. It is an extremely slow reaction that in nature can take months to occur. In order to increase the rate of reaction a concentrated acid is used as a catalyst, in this case HCl, but usually when conducted in a lab concentrated sulphuric acid. HCl may not be present in a large enough quantity within the gastric acid in the stomach. In order to counter this, it may be required to add additional catalyst, when also consuming the ethanoic acid. Catalysts like this, allow reactions to be completed at a faster rate as they reduce the activation energy required for a reaction between two colliding particles to occur.
Additionally, when conducting an esterification reaction in a laboratory it is important to note that a process known as reflux is used where the reaction is heated extensively so as to evaporate more volatile substances whilst simultaneously condensing the evaporated substances so that reactants are not lost in the process. This heating of the mixture increases the rate of reaction by allowing the particles to move faster as they have more energy and allowing them more of a chance to collide. Since reactions only occur when particles collide in certain ways, increasing the amount of times they collide in turn increases the likelihood of a reaction occurring between the two, meaning that the reaction is completed faster.
Additionally, most (but not all) esterification reactions are endothermic, and all are in equilibrium. Therefore, through the addition of heat, according to Le Châtelier’s Principle, the reaction will shift right and produce more product (ester and water), whilst consuming more reactants (alcohol and carboxylic acid) so as to counteract the changes made to equilibrium. This means that more alcohol can be converted to esters and water and less alcohol will remain present in the body requiring organs such as the liver to process it.
However, the average human’s internal temperature is approximately 37 degrees Celsius, not high enough to increase the reaction rate to what it is when esterification is performed in the laboratory, where the mixture is usually heated to at least 60 degrees Celsius. This means that the reaction may take much longer than 2hours let alone 30 minutes, which is approximately the time it takes for alcohol to enter the bloodstream, as previously mentioned, and it will be too late to stop intoxication at this point. This issue therefore limits the effectiveness of esterification as a means to prevent intoxication.
Additionally, ethanoic acid along with most other carboxylic acids is corrosive. This is often a risk which must be managed within the laboratory through the use of safety equipment such as safety googles, gloves and lab coats, and precautions so as to not consume any. However, in order for esterification to act as a means of preventing intoxication AFTER alcohol has been consumed, the carboxylic acid must therefore be consumed and enter the body in order for the reaction to occur. Ingestion of acetic acid will most likely result in the corrosion of the mouth, oesophagus and throat. However, the stomach which already has acid within it and is designed to withstand the presence of acids and other corrosive substances will be able to hold the ethanoic acid. Therefore, if it is possible to consume the ethanoic acid without it coming into contact with the mouth oesophagus throat and other such organs, the problem can be resolved. One such way that this could be done is by consuming the carboxylic acid in a tablet/pill form with a plastic covering which breaks/dissolves only once it reaches the stomach. This would prevent contact with other organs which cannot withstand acetic acids corrosive nature.
Conclusion
Thus it is evident that organic chemistry concepts such as esterification are extremely important to society. From the report it can be concluded that currently esterification most likely couldn’t be used to prevent intoxication due to its extremely slow reaction time and the corrosive nature of carboxylic acids. However, if further research is completed and ways are fond to increase the rate of reaction of esterification within the human body, it is very much possible to minimise intoxication after alcohol has been consumed. This will definitely have positive impacts on society
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