Acetic Acid Packing
ACETIC ACID
Acetic acid, also known as ethanoic acid, is a chemical compound found in many different products. It’s perhaps most well-known as the main component of vinegar, apart from water, and is thought to supply ingredients like apple cider vinegar with many of their health-promoting properties. Chemically speaking, the ethanoic acid formula is C2H4O2, which can also be written as CH3COOH or CH3CO2H. Because of the presence of a carbon atom in the CH₃COOH structure, it’s considered an organic compound. The ethanoic acid density is about 1.05 grams/cm³; compared to other compounds like nitric acid, sulfuric acid or formic acid, the density of ethanoic acid is quite a bit lower. Conversely, the ethanoic acid melting point is significantly higher than many other acids, and the ethanoic acid molar mass and ethanoic acid boiling point tend to fall right about in the middle. Aside from its uses as a natural preservative and common ingredient in a variety of products, ethanoic acid has also been associated with several impressive health benefits. In addition to its potent anti-bacterial properties, this organic compound is also thought to reduce blood sugar levels, promote weight loss, alleviate inflammation and control blood pressure. In biochemistry, the acetyl group, derived from ethanoic acid, is essential for life. When bound to coenzyme A, it plays an essential role in the metabolism of carbohydrates and fats. The global demand for industrial and edible ethanoic acid is about 6.5 million tons per year.
A LOOK AT THE HISTORY OF ACETIC ACID
Vinegar was known in early civilizations as a natural product of aerobic reactions of alcoholic beverages, because ethanoic acid-producing bacteria are present in all environments. The use of ethanoic acid in chemistry expanded until the 3rd century BC; When the Greek philosopher “Theophrastus” described the effect of vinegar on metals to produce useful pigments (= including lead carbonate, green mixture of copper salts).
In the 16th century, the German chemist Andreas Libavius proposed the production of acetone from the dry distillation of lead acetate, known as ketonic decarboxylation. The presence of water in vinegar has many effects on the properties of ethanoic acid; For centuries, chemists believed that glacial ethanoic acid and the acid in vinegar were two different substances. French chemist “Pierre Audet” proved that both compounds are the same. In 1845, the German chemist “Hermann Kolbe” synthesized ethanoic acid from inorganic compounds for the first time. This reaction sequence includes the chlorination of carbon disulfide to carbon tetrachloride; And after that, the pyrolysis of tetrachloroethylene and the chlorination of the aqueous solution of trichloroacetic acid, which ends in ethanoic acid due to electrolytic decomposition. Until 1910, most glacial ethanoic acid was obtained from wood distillation.
ACETIC ACID PRODUCTION METHODS
Liquid acetic acid is produced by two industrial methods and bacterial fermentation. About 75% of the acetic acid made for use in the chemical industry is produced by the carbonylation process of methanol, which is described in the following section. The biological pathway of ethanoic acid production comprises only about 10% of global production, but is still important for vinegar production; Because many food standards laws are very sensitive about the biological origin of vinegar used in food. Other processes for the production of this material include isomerization of methyl formate and gas phase oxidation of ethylene and ethanol. Ethyl acid is often a by-product of various reactions, i.e., it is obtained during the synthesis of acrylic acid with a heterogeneous catalyst or the production of lactic acid by a fermentation process.
1- METHANOL CARBONYLATION REACTION
Most of the acetic acid is produced by the carbonylation of methanol. In this process, methanol and carbon monoxide produce acetic acid according to the reaction equation shown below:
This process involves the production of iodomethane as an intermediate compound and occurs in three steps. A metal carbonyl catalyst is required for carbonylation (step 2).
CH3OH + HI → CH3I + H2O
CH3I + CO → CH3COI
CH3COI + H2O → CH3COOH + HI
By changing the process conditions, acetic anhydride may also be produced in the same reaction using rhodium catalysts.
2- ACETALDEHYDE OXIDIDATION
Before the commercialization of the “Monsanto process”, most of the acetic acid was produced by the oxidation of acetaldehyde. This is the second most important method of production that still exists; Although usually not competitive with the carbonylation of methanol. Acetaldehyde can be produced from acetylene hydration method. This technology was dominant in the early 1900s.
The light components of naphtha are easily oxidized by oxygen or even air, producing peroxide compounds, which decompose according to the chemical equation and produce acetic acid:
2C4H10 +5O2 → 4CH3CO2H + 2H2O
Such oxidation reactions require metal catalysts such as manganese, cobalt and chromium naphthenate salts.
Typical reaction conditions are 150°C (302°F) and 55 atmospheres. Byproducts may also be formed, including butanone, ethyl acetate, formic acid, and propionic acid.
These by-products are also commercially valuable and the reaction conditions may be changed to produce more of them if needed. However, the separation of acetic acid from these by-products will be more expensive.
Under similar conditions and using the same catalysts for butane oxidation, oxygen in the air can oxidize acetaldehyde to produce acetic acid:
2CH3CHO + O2 → 2CH3CO2H
With the use of new catalysts, this reaction can produce more than 95% of this acid. The major byproducts are ethyl acetate, formic acid, and formaldehyde, all of which have a lower boiling point than acetic acid and are easily separated by distillation.
3- ETHYLENE OXIDATION
Acetaldehyde may be prepared from ethylene through the Wacker Process and then oxidized by the above methods.
This process is catalyzed by a palladium metal catalyst immobilized on a heteropolyacid such as “silicotungstic acid”. A similar process occurs from the same metal catalyst on silicotungstic acid and silica:
C2H4 + O2 → CH3CO2H
This method will be based on the use of a new technology based on selective photocatalytic oxidation, for selective oxidation of ethylene and ethane and conversion to acetic acid. Unlike older oxidation catalysts, the selective oxidation process uses UV light to produce acetic acid at ambient temperature and pressure.
4- OXIDATIVE FERMENTATION
In the history of mankind, bacteria related to acetic acid from the genus Acetobacter made acetic acid in the form of vinegar. Due to the availability of sufficient oxygen, these bacteria can produce vinegar from all kinds of alcoholic foods. Foods commonly used include apples, fermented grains, malt, rice or potatoes. The general chemical reaction that occurs by these bacteria is as follows:
C2H5OH + O2 → CH3COOH + H2O
5- ANAEROBIC FERMENTATION
Anaerobic bacteria species, including the “Clostridium” or “Acetobacterium” family, can convert sugars into acetic acid without creating ethanol as an intermediate. The general chemical reaction carried out by these bacteria is as follows:
C6H12O6 → 3CH3COOH
These acetogenic bacteria produce acetic acid from one-carbon compounds such as methanol, carbon monoxide, or a mixture of carbon dioxide and hydrogen:
2CO2 + 4H2 → CH3COOH + 2H2O
WHAT IS ACETIC ACID USED FOR ?
The most popular application of acetic acid is its use in vinegar. It is also extremely useful in the production of the vinyl acetate monomer (often abbreviated to VAM). This monomer is an important prerequisite in the production of paints and adhesives. Acetic acid uses are many and varied. This acid is used in goods manufacturing, in food processing, in the cleaning industry, in medicine, and as a health supplement. Acetic acid is also a biochemical essential in acetyl group form where it is fundamental to the construction of amino acids and therefore impossible to exist without. Let’s have a look at a few of these acetic acid uses in more detail.
APPLICATIONS OF ACETIC ACID
This substance is a chemical reagent for the production of chemical compounds. The biggest and most important application of acetic acid is its use in the production of vinyl acetate monomer. The volume of acetic acid in vinegar is relatively small. We introduce the most important application of this material in different industries and sectors in the following sections.
1- PRODUCTION OF VINYL ACETATE MONOMER
The main application of this material is the production of vinyl acetate monomer (VAM). In 2008, it was estimated that the production of this monomer consumes a third of the acetic acid produced in the world. This reaction involves ethylene and ethanoic acid in the presence of oxygen on a palladium catalyst, which is carried out in the gas phase:
2H3C − COOH + 2C2H4 + O2 → 2H3C − CO − O − CH = CH2 + 2H2O
Vinyl acetate can be converted into polyvinyl acetate or other polymers, which are primary compounds of paint and glue.
2- ESTER PRODUCTION
Esters with an acetic acid structure are commonly used as solvents for inks, paints, and coatings. These esters include ethyl acetate, n-butyl acetate, isobutyl acetate and propyl acetate. They are typically produced by a catalyzed reaction from acetic acid and the corresponding alcohol. Acetate ethers are used as nitrocellulose solvents, acrylic varnishes, varnish removers and wood stains.
3- PRODICTION OF ACETIC ANHYDRIDE
The product of the condensation process of two acetic acid molecules is acetic anhydride. The world production of acetic anhydride is a major application of ethanoic acid and it comprises approximately 25 to 30% of the world production of acetic acid.
The main process in the production of acetic anhydride includes the dehydration of acetic acid to produce ketene at 700-750 degrees Celsius. The ketone then reacts with acetic acid to give the anhydride:
CH3CO2H → CH2 = C = O + H2O
CH3CO2H + CH2 = C = O → (CH3CO)2O
Acetic anhydride is an acetylating agent. Likewise, its main use is in the production of cellulose acetate; Synthetic fibers also used for photographic films.
4- VINEGAR ESSENCE AS A SOLVENT
As mentioned above, glacial acetic acid is a polar protic solvent. This substance is often used as a solvent for recrystallization, for the purification of organic compounds. Acetic acid is used as a solvent in the production of terephthalic acid (TPA), the raw material of polyethylene terephthalate (PET).
Acetic acid is often used as a solvent for periodic reactions, such as Friedel-Crafts alkylation. For example, glacial acetic acid is used in chemistry to evaluate weak alkaline substances such as organic amides. Glacial acetic acid is a much weaker base than water, so the amide behaves as a strong base in this environment. It can then be titrated from a very strong acid such as perchloric acid using glacial acetic acid solution.
5- USE OF ETHANOIC ACID IN MEDICINE
Injecting acetic acid into tumors has been used to treat cancer since the 1800s. Acetic acid is an effective disinfectant that is used as a 1% solution. This acid can fight the activity of a wide range of microorganisms such as streptococci, staphylococci, pseudomonas, enterococci, etc.
One of the uses of acetic acid for the skin is the treatment of skin infections caused by Pseudomonas bacteria resistant to common antibiotics.
6- ETHANOIC ACID IN FOOD INUSTRY
There are 349 kcal per 100 grams of acetic acid. Because vinegar has a small percentage of acetic acid, it is used for food. Vinegar is directly used as seasoning and pickling of vegetables and other foods.
Edible vinegar is more dilute (containing 4-8% acetic acid), while industrial food souring agents use solutions that are more concentrated.
OTHER USES OF ACETIC ACID DERIVATIVES
Many organic or inorganic salts are produced from acetic acid. Some of the derivatives of this important compound that are commercially significant are as follows:
- Sodium acetate, which is used in the textile industry and as a food preservative (E262).
- Copper (II) acetate, which is used as a pigment and fungicide.
- Aluminum acetate and iron (II) acetate, which are used as raw materials for paints.
- Palladium(II) acetate is used as a catalyst for coupling reactions in organic chemistry.
- Chloroacetic acid (monochloroacetic acid, MCA), dichloroacetic acid (considered as a byproduct), and trichloroacetic acid. MCA is used in making indigo dye.
- Bromoacetic acid, which is used to produce ethyl bromoacetate ester reagent.
- Trifluoroacetic acid is a common reagent in organic synthesis.
STRUCTURE OF ACETIC ACID-CH3COOH
- It can be observed in the solid-state of acetic acid that there is a chain of molecules wherein individual molecules are connected to each other via hydrogen bonds.
- Dimers of ethanoic acid in its vapour phase can be found at temperatures approximating to 120o.
- Even in the liquid phase of ethanoic acid, its dimers can be found when it is present in a dilute solution. These dimers are adversely affected by solvents that promote hydrogen bonding.
- The structure of acetic acid is given by CH3(C=O)OH, or CH3CO2H.
- The structure of acetic acid is illustrated below.
Structurally, ethanoic acid is the second simplest carboxylic acid (the simplest being formic acid, HCOOH), and is essentially a methyl group with a carboxyl functional group attached to it.
ACETIC ACID IN GOODS MANUFACTURING
Acetic acid is an important chemical reagent used to produce acetate, adhesives, glues, and synthetic fabrics. Acetic acid is also used in electroplating where a metal coating is deposited onto an object by placing it in a solution that contains a specific metal salt. The solution needs to be conductive and acids that donate hydrogen ions create ideal conditions. Furthermore, electroplating can only occur within a solution and metal salts only dissolve in solutions with a low (acidic) pH value. CH₃COOH is a raw material used for the production of cellulose acetate, acetic anhydride (plastics) and chloroacetic acid used in the production of dyes and pesticides as well as certain drugs.
ACETIC ACID IN FOOD PROCESSING
Acetic acid used in food processing to regulate the acidity or alkalinity levels of foods. The Code of Federal Regulations (CFR) categorizes acetic acid as a general-purpose food additive which is safe when used in accordance with good manufacturing practices. In Europe, E-number regulations apply to all food additives. Acetic acid has been given code E260 and is considered a safe ingredient that controls bacterial colonization and can be used without limitation. This is not a new finding. It is said that the ancient Babylonians used vinegar as a food preservative. Vinegar is used to produce salad dressings, condiments that include mustard, ketchup, and mayonnaise, and in sauces and pickles.
ACETIC ACID FOR CLEANING
Acetic acid has been used as a cleaning product and deodorizer for centuries if not millennia; sponges of vinegar were placed in expensive filigree rings worn by the rich whenever they stepped through filthy and stinking eighteenth-century streets. The deodorizing properties of vinegar have also been taken advantage of for generations. Sailors used vinegar to scrub the decks of the ships they worked and lived on. The principles of microbial control may not have been understood at the time but the fresh-smelling, clean and illness-preventing characteristics of this organic solution were definitely well known. Adding an alkaline product to acid causes a bubbling, fizzing reaction. Some traditional cleaners believe this effect produces a deeper clean to stable surfaces. For example, scrubbing the back yard with alkaline caustic soda (sodium hydroxide) and then using a vinegar mix on top of this will set off a reaction that certainly looks as if it has a deep-cleaning action; however, this does very little to increase the hygienic effect but rather buffers or works against the alkaline cleaning power of the caustic soda with the acidic properties of vinegar. Today, many dedicated fans of white vinegar advertise the ecological benefits of using diluted acetic acid to clean bathrooms, wash clothes, remove odors, and make food preparation surfaces both clean and safe. ethanoic acid also removes rust and lime scale deposits.
ACETIC ACID IN MEDICINE
Acetic acid or vinegar has probably been used in medicine since before the written word. Should you have suffered from an open wound on the island of Kos in the fourth century before Christ, you may have been prescribed a daily vinegar wash by Hippocrates. If you had a sore throat, he might also have asked you to mix honey and vinegar to make Oxymel, an ancient Greek cough medicine; if you had served in Europe during the First World War, you may only have had access to vinegar keep clean and remain free of infection. Today, acetic acid solutions are used in laboratory blood testing processes as a slide wash. They remove bacterial biofilms in wounds and the digestive system, and have often been used for outer ear infections and so avoid the use of antibiotics. Ingestion of vinegar increases acetate levels in the colon and promotes calcium uptake with lower blood pressure and higher bone density as a result. Studies are looking into the use of acetate as an antitumor medication.
ACETIC ACID AS A HEALTH SUPPLEMENT
Acetic acid is a popular health supplement and consumed in the form of vinegar, most commonly apple cider vinegar. When bound to coenzyme A, the acetyl group of acetic acid is central to carbohydrate and fat metabolism.
PROPERTIES OF ACETIC ACID
Acetic acid in the form of pure CH3COOH is a colourless liquid. It has highly corrosive and irritating properties. When mixed with water, a volume contraction occurs – in the case of ethanoic acid, this is a significant reduction in volume. Ethanoic acid is a hygroscopic substance, which means that it is able to absorb water from various sources. This property of acetic acid and the ability to dissolve water in it mean that when you open a bottle with the acid, the substance it contains can even solidify in contact with humid air. At low temperatures, crystals that resemble ice form on the surface of ethanoic acid. This phenomenon only occurs with pure ethanoic acid or at very low temperatures, to which the so-called acetic essence is exposed. An important feature of acetic acid is its ability to dissociate. As it is a carboxylic acid, it dissociates and therefore conducts electricity well. It has a very high boiling point, which is due to the chemical structure of the substance.
Acetic Acid | CH3COOH |
Molecular weight/molar mass of CH3COOH | 60.052 g/mol |
Density of Acetamide | 1.05 g/cm³ |
Boiling Point of Acetamide | 118 °C |
Melting Point of Acetamide | 16.6 °C |
PHYSICAL PROPERTIES OF ACETIC ACID
Even though ethanoic acid is considered to be a weak acid, in its concentrated form, it possesses strong corrosive powers and can even attack the human skin if exposed to it.
Some general properties of acetic acid are listed below:
- Ethanoic acid appears to be a colourless liquid and has a pungent smell.
- At STP, the melting and boiling points of ethanoic acid are 289K and 391K respectively.
- The molar mass of ethanoic acid is 60.052 g/mol and its density in the liquid form is 1.049 g.cm-3.
- The carboxyl functional group in ethanoic acid can cause ionization of the compound, given by the reaction: CH3COOH ⇌ CH3COO– + H+
- The release of the proton, described by the equilibrium reaction above, is the root cause of the acidic quality of ethanoic acid.
- The acid dissociation constant (pKa) of ethanoic acid in a solution of water is 4.76.
- The conjugate base of ethanoic acid is acetate, given by CH3COO–.
- The pH of an ethanoic acid solution of 1.0M concentration is 2.4, which implies that it does not dissociate completely.
- In its liquid form, aethanoic acid is a polar, protic solvent, with a dielectric constant of 6.2.
The metabolism of carbohydrates and fats in many animals is centered around the binding of ethanoic acid to coenzyme A. Generally, this compound is produced via the reaction between methanol and carbon monoxide (carbonylation of methanol).
CHEMICAL PROPERTIES OF ACETIC ACID
The chemical reactions undergone by ethanoic acid are similar to those of other carboxylic acids. When heated to temperatures above 440oC, this compound undergoes decomposition to yield either methane and carbon dioxide or water and ethenone, as described by the following chemical equations.
CH3COOH + Heat → CO2 + CH4
CH3COOH + Heat → H2C=C=O + H2O
Some metals such as magnesium, zinc, and iron undergo corrosion when exposed to ethanoic acid. These reactions result in the formation of acetate salts.
2CH3COOH + Mg → Mg(CH3COO)2 (magnesium acetate) + H2
The reaction between ethanoic acid and magnesium results in the formation of magnesium acetate and hydrogen gas, as described by the chemical equation provided above.
ACETIC ACID A STRONG ACID?
No, CH3COOH is a weak acid. It undergoes complete dissociation only when it is reacted with a strong base. Hydrochloric acid is a much stronger acid than ethanoic acid.
HOW CAN ACETIC ACID BE PREPARED ?
It can be prepared by reacting methanol with hydrogen iodide and adding carbon monoxide to the product (methyl iodide) in order to obtain acetyl iodide. Upon hydrolysis, acetyl iodide yields ethanoic acid.</p>
IS ACETIC ACID A VINEGAR?
Vinegar is a solution of ethanoic acid in water and contains between 5% to 8% ethanoic acid by volume.</p>
IS ACETIC ACID HARMFUL TO HUMANS?
Exposure to more concentrated solutions of ethanoic acid (>25%) can cause corrosive damage. Breathing vapours with high levels of ethanoic acid can cause irritation of eyes, nose and throat, cough, chest tightness, headache, fever and confusion.
HOW TO HANDLE ACETIC ACID SAFELY
When handling CH₃COOH, it is essential to keep a few critical safety tips in mind. Never add water to this chemical, and always keep ethanoic acid away from sources of heat, sparks or flame. Wear suitable respiratory equipment if handling CH₃COOH in an area that isn’t well-ventilated. It is recommended that you wear the following protective gear when using ethanoic acid:
- Gloves
- Splash goggles
- Synthetic apron
- Vapor respirator (if needed)
Ensure that eye-wash stations are nearby if handling ethanoic acid. In the event of a large spill in either the workplace or at home, a self-contained breathing apparatus should be equipped, and you should also wear a full protective suit for additional safety. If you do not have this equipment readily at hand, do not attempt to clean up the ethanoic acid without it.</p>
STORAGE OF ACETIC ACID
- The best conditions for keeping and storing barrels or tanks of this substance are warehouses equipped with a strong ventilation system. Avoid storing tanks near sources of heat and combustion.
- Fire prevention measures, as well as the production of aerosols and dust caused by powdered or liquid ethanoic acid, must be observed in the warehouses of this organic compound.
- Smoking is prohibited in the storage warehouses of this substance. Keep the acid container tightly closed. Avoid mixing acid with incompatible compounds.
- The best recommended storage temperature for ethanoic acid is 15-25 degrees Celsius.
ACETIC ACID PACKAGING
Ethanoic acid packaging, this material is packaged in gallons or barrels. For powdered ethanoic acid, bags are used for packaging. Gallons are usually 5 liters, but for Merck’s glacial ethanoic acid, the packages are 2.5 liters. It is also possible to transport acid in bulk by tanker. Bulk shipping is suitable for industrial orders.
TECHNICAL DATA SHEET OF ACETIC ACID
Colorless | Liquid | ||
---|---|---|---|
Packaging | HDPE plastic bottle | ||
Vapor Density | 2.1 | ||
pH | 2.5 | ||
Boiling Point | 117°C | ||
Molecular Formula | C2H4O2 | ||
Formula Weight | 60.05g/mol | ||
Nickel (Ni) | ≤0.1ppm | ||
Vapor Pressure | 1.52kPa at 20°C | ||
Melting Point | 16°C | ||
Color | Colorless |
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