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5-Chloropentanoic acid is an important organic compound that finds application in various fields of the chemical industry.
It is commonly used as a building block for the synthesis of various chemicals, drugs, and other products.
The synthetic routes of 5-chloropentanoic acid can be broadly classified into two categories: chemical synthesis and biological synthesis.
Chemical Synthesis:
Chemical synthesis of 5-chloropentanoic acid involves various chemical reactions that convert simple starting materials into the desired product.
The following are the commonly used chemical synthetic routes:
- Haloform reaction: This reaction involves the treatment of chloroform with sodium hydroxide in the presence of a solvent such as ether.
The product is then extracted with water and the organic layer is dried and evaporated to obtain 5-chloropentanoic acid. - Reduction of 5-bromopentane: 5-Bromopentane can be reduced to 5-chloropentane using a reducing agent such as lithium aluminum hydride (LiAlH4).
The reaction involves the elimination of bromine and the reduction of the alkene to an alkane. - Halogenation of pentan-2-one: 5-Chloropentanoic acid can also be synthesized by halogenation of pentan-2-one using chlorine or bromine.
The halogenation reaction involves the substitution of one of the methylene groups in the pentan-2-one with a halogen atom.
Biological Synthesis:
Biological synthesis of 5-chloropentanoic acid involves the use of microorganisms or enzymes to convert simple starting materials into the desired product.
The following are the commonly used biological synthetic routes:
- Bacterial fermentation: This process involves the use of microorganisms such as Escherichia coli or Bacillus subtilis to produce 5-chloropentanoic acid.
The microorganisms are genetically engineered to produce the enzyme that catalyzes the conversion of the starting material into 5-chloropentanoic acid. - Enzymatic hydrolysis: This process involves the hydrolysis of a substituted succinic acid ester using an enzyme such as chloropentanolase.
The enzyme catalyzes the hydrolysis of the ester to produce 5-chloropentanoic acid.
Advantages and Limitations of Synthetic Routes:
The chemical synthetic routes of 5-chloropentanoic acid offer several advantages over the biological routes.
The reaction conditions can be easily controlled, and the reaction times can be reduced to a few hours.
The synthetic routes also offer excellent selectivity and stereochemical control over the product.
However, the chemical synthetic routes also have some limitations.
The reaction conditions can be hazardous, and the reaction byproducts can be toxic and difficult to dispose of.
The biological synthetic routes of 5-chloropentanoic acid offer several advantages over the chemical routes.
The reaction conditions are mild, and the reaction times are shorter.
The biological routes are also environmentally friendly, as they do not generate toxic byproducts.
However, the biological routes have some limitations.
The yields of the product are often lower than the chemical routes, and the product purity can be difficult to control.
Conclusion:
5-Chloropentanoic acid is an important organic compound with various applications in the chemical industry.
The synthetic routes of 5-chloropentanoic acid can be broadly classified into chemical and biological routes.
The chemical routes involve various chemical reactions that convert simple starting materials into the desired product, while the biological routes involve the use of microorganisms or enzymes to convert starting materials into the