Dhristi JEE 2022-24

Introduction to Butanoic Acid

Butanoic acid is an oily and colourless liquid having the chemical formula CH3CH2CH2-COOH. It is a type of short-chain saturated fatty acid, which is found in the form of esters in plant oils and animal fats. In 186, Lieben and Rossi discovered Butanoic acid. It is also known as butyric acid, which is meant by butter acid because it was first discovered in rancid butter. And it was prepared by the fermentation of the butyric carbohydrates and also by the oxidation of n-butyl alcohol.

 

The other names of this acid are given as n-Butyric acid, butyric acid, and n-Butanoic acid.

 

Properties of Butanoic Acid

Let us discuss a few properties of Butanoic acid as tabulated below.

IUPAC Name

Butanoic acid

Butanoic acid formula or butyric acid formula or structural formula of butanoic acid

C4H8O2

Molecular Weight or Molar Mass

88.11 g/mol

Density

960 kg/m³

Boiling Point

163.5 °C

Melting Point

-7.9 °C

Chemical Formula

CH3CH2CH2-COOH

 

Physical Properties of Butanoic Acid - C4H8O2

A few of the physical properties of Butanoic acid are listed as follows.

  • Butanoic acid has an odor as Unpleasant odor,

  • Its appearance is Colourless clear liquid,

  • It has the covalently bonded unit as 1,

  • The heat capacity of the butanoic acid can be given as 298.15 K, 1 atm,

  • Its complexity is 49.5,

  • The solubility of the butanoic acid is Miscible in water and ethanol.

 

Chemical Properties of the Butanoic Acid - C4H8O2

  • Butanoic acid reacts with the sodium hydroxide and forms carbon dioxide, the sodium salt of butanoic acid, and water. The chemical equation can be given as follows.

21C₄H₈O₂ + 20NaOH   →  20NaC₄H₆O + 4CO₂ + 34H₂O

  • Butanoic acid, on treatment with the water, produces ether and acetic acid. The chemical equation can be given as follows.

C₄H₈O₂ + H₂O  →  CH₃COOH + C₂H₆O

 

Occurrence of Butanoic Acid

The triglycerides of butyric acid compose 3 to 4 percent of butter. When the butter goes rancid, the butyric acid liberates from glyceride using the hydrolysis process. It is one of the fatty acid subgroups, which is known as short-chain fatty acids. Butyric acid is also a typical carboxylic acid, reacts with bases, and affects various metals. It is found in plant oils, animal fat, breast milk, bovine milk, butter, body odor, parmesan cheese, vomit, and also as an anaerobic fermentation product (including in the colon).

 

It has a kind of taste like butter and gives an unpleasant odor. Mammals having good scent detection abilities, like dogs, can detect this at 10 parts per billion. At the same time, humans can detect this acid only in concentrations above 10 parts per million. In the manufacturing of food, it can be used as a flavoring agent.

 

In humans, this acid is one of two primary endogenous agonists of the human hydroxycarboxylic acid receptor 2 (HCA2), which is a receptor of Gi/o-coupled G protein-coupled.

 

Butyric acid is available as its octyl ester in the seed of the ginkgo tree and in parsnip (Pastinaca sativa).

 

Production of Butyric Acid

  1. Fermentable Fiber Sources

Highly-fermentable fiber residues, like those from oat bran, resistant starch, pectin, and guar, are transformed by the colonic bacteria into short-chain fatty acids (SCFA) like butyrate, producing more SCFA that of less fermentable fibers, including celluloses. A study found that resistant starch produces consistently more butyrate compared to the other dietary fiber types. Production of SCFA from fibers in ruminant animals like cattle is responsible for the butyrate content of butter and milk.

 

Uses of Butyric Acid

Butyric acid can be used in various butyrate ester preparation. It can also be used to produce cellulose acetate butyrate (CAB), which is helpful to use in a wide range of paints, tools, and coatings, and it is also more resistant to degradation compared to cellulose acetate. However, CAB can be degraded with exposure to moisture and heat, releasing butyric acid.

 

The butyric acid esters of low-molecular-weight, such as methyl butyrate, have mostly pleasant tastes or aromas. As a consequence, these can be used as perfume and food additives. It is also considered an approved food flavoring in the EU FLAVIS database (08.005).

 

Because of its powerful odor, it can also be used as a fishing bait additive. Many commercially available flavors used in carp (Cyprinus carpio) baits will use butyric acid as their ester base. But, it is unclear whether fish are self attracted by the butyric acid or by the substances added to it. However, Butyric acid was one of the few organic acids shown to be palatable for both bitterling and tench. This substance has also been used as a stink bomb by SSCS (Sea Shepherd Conservation Society) in disrupting the Japanese whaling crews.

 

Butyric acid or Butanoic acid is an oily, colorless liquid. The chemical formula is CH3CH2CH2-COOH. Butanoic acid is a type of short-chain saturated fatty acid  found in vegetable oils in the form of animal fats and esters. This means butyric acid  first found in rancid butter. Butanol acid was made by oxidizing n-butyl alcohol and butter carbohydrates. Butyric acid is most commonly found in the form of esterified vegetable oils and animal fats. 


Structure of Butanoic Acid 

Butyric acid or Butanoic acid is a carboxylic acid having the structural formula CH3CH2CH2COOH. Where -COOH is a functional group attached. 


Butyric acid is made up of 3-4 percent  butter. When butter is rancid, it is released by hydrolysis of glyceride. Butanoic acid is  a typical carboxylic acid that usually reacts with bases and attacks various metals. 


Butyric acid tastes like butter and has an unpleasant odor. Mammals like dogs can detect this at 10 ppb. On the other hand, humans can only detect this acid at concentrations above 10 ppm.


Physical Properties of Butanoic Acid 

Odour

Unpleasant odor

Appearance

Colorless clear liquid

Covalently-Bonded Unit

1

Heat capacity

298.15 K, 1 atm

Complexity

49.5

Solubility

Miscible in water and ethanol.


Key Properties of Butanoic Acid 

C4H8O2

Butanoic acid

Density

960 kg/m³

Molecular Weight/ Molar Mass

88.11 g/mol

Boiling Point

163.5 °C

Melting Point

-7.9 °C

Chemical Formula

CH3CH2CH2-COOH


Butanoic Acid Uses 

  • Butanoic acid is used as a food additive in the production of esters, artificial flavors in the production of varnishes, and decalcification of leather. 

  • Butyric acid is used in the manufacture of flavors, perfumes, disinfectants, and pharmaceuticals. 

  • Butyric acid gives flavor in beer, foods, detergent powders and cosmetics. 

  • Butanoic acid is used as a safe food additive for feeding or manufacturing processes. It is especially found in milk. 


Key Points to Remember 

  • The name "butyric acid", also known as butyric acid,  means butyric acid  first found in rancid butter. Butanoic acid plays an important role as a metabolite in human urine and as a metabolite in mycoplasma genitalium. Butyric acid is also known as n-butyric acid, butyric acid, and n-butyric acid.

  • Butanoic acid is used  as a food additive in the production of esters, artificial flavors in the production of varnishes, and decalcification of leather. Butyric acid is an oily and colorless liquid. 

  • The chemical formula for butanoic acid is CH3CH2CH2COOH. Butanoic acid is a type of short-chain saturated fatty acid mainly found in vegetable oils in the form of animal fats and esters. Butyric acid is made up of 3-4 percent  butter. 

  • Butanoic acid  reacts with sodium hydroxide to form carbon dioxide with water and salts of butanoic acid, and butanoic acid  reacts with water to form ether and acetic acid.

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FAQs (Frequently Asked Questions)

1. Explain the Preparation of Butanoic Acid?

Industrially, butyric acid can be prepared using Butyraldehyde oxidation. Saturation with the salts like calcium chloride can isolate it from the aqueous solutions. Calcium salt, Ca(C4H7O2)2·H2O, is relatively less soluble when dissolved in hot water.

2. Explain Fructans.

Fructans are the other prebiotic soluble dietary fiber source that is digested to form butyrate. These are often found in the food soluble fibers, which are high in sulfur, like cruciferous vegetables and allium. The fructans sources include wheat (although a few wheat strains like spelt with lower amounts), barley, rye, onion, garlic, and many more.

3. Give some information on Microbial Biosynthesis of Butanoic Acid?

Butyrate can be generated using multiple fermentation processes that are performed by the obligatory anaerobic bacteria. This fermentation pathway was discovered by Louis Pasteur in 1861. Some examples of bacteria that produce butyrate are Clostridium kluyveri, Clostridium butyricum, and Clostridium pasteurianum.

4. Explain the reactions of Butanoic Acid?

Butyric acid reacts as a carboxylic acid, typically, and it can form ester, amide, chloride, and anhydride derivatives. Commonly, the latter, butyryl chloride, can be used as an intermediate to obtain the others.

5. What are the foods that contain Butanoic Acid?

Food that contain Butanoic Acid are:

  • Ghee, Oil and butter contain about 3-4% of butanoic acid 

  • It is very common in dairy products such as milk, cheese, and yoghurt. 

  • It is found in whole grains 

  • It is highly found in vegetables and fruits such as Bananas, avocados, raspberries, Onions etc or anything that contains fibres. 

  • It is found in beans and legumes

6. What are the benefits of Butyrate?

The benefits of Butyrate are:

  • Weight loss

  • Decreases inflammation

  • Protects and boosts immune system 

  • Improve digestion

  • Protects against cancer

7. What is the formula for Butanoic acid?

Butyric acid or Butanoic acid is a carboxylic acid having the structural formula CH3CH2CH2COOH. Where -COOH is a functional group attached.

8. What do you understand by Butanoic acid?

Butyric acid or Butanoic acid is an oily, colorless liquid. The chemical formula is CH3CH2CH2-COOH. Butanoic acid is a type of short-chain saturated fatty acid found in vegetable oils in the form of animal fats and esters.

9. What are the other names for Butanoic acid?

Butyric acid or Butanoic acid is also known as n-butyric acid, butyric acid, and n-butyric acid.

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