The key difference between acetylacetoacetic ester and malonic ester is that acetylacetoacetic ester is the ethyl ester of the acetoacetic acid whereas malonic ester is the ester of malonic acid.
Acetylacetoacetic ester and malonic ester are terms we use in organic chemistry because they are esters: organic compounds. The synthesis processes of acetylacetoacetic ester resemble the synthesis of malonic ester; thus, it is important to know the difference between them.
CONTENTS
1. Overview and Key Difference
2. What is Acetylacetoacetic Ester
3. What is Malonic Ester
4. Side by Side Comparison – Acetylacetoacetic Ester vs Malonic Ester in Tabular Form
5. Summary
What is Acetylacetoacetic Ester?
Acetylacetoacetic ester is the ethyl ester of the acetoacetic acid. Its synonyms include ethyl acetoacetate, Acetoacetic acid ethyl ester, Ethyl acetylacetate, etc. However, the IUPAC name of this organic compound is Ethyl 3-oxobutanoate. The chemical formula of this compound is C6H10O3. It appears as a colourless liquid and the molar mass of the compound is 130.14 g/mol. Moreover, it has a fruity odour which resembles the odour of rum.
Acetylacetoacetic ester is very important in the production of several different compounds, including amino acids, antibiotics, antimalarial agents, vitamin B complexes, etc. Moreover, we can use this compound in the production of dyes, lacquers, inks, yellow paint pigments, perfumes, etc. Besides, this compound is also useful as a flavouring agent due to its fruity odor.
When considering the synthesis process, we can produce Acetylacetoacetic ester by combining two ethyl acetate molecules, which gives one acetylacetoacetic molecule and ethanol. The reaction is as follows:
Figure 01: Reaction for the Production of Acetylacetoacetic Ester
What is Malonic Ester?
Malonic ester is the ester of malonic acid. The systemic name for this compound is propanedioic acid. The most common compound of the group of malonic esters is diethyl malonate.
Figure 02: Malonic Ester Synthesis
Further, this compound involves in the malonic ester synthesis process. In this process, diethyl malonate or another ester compound of malonic acid undergoes alkylation at its alpha carbon atom (to both carbonyl groups) and then converts into a substituted acetic acid molecule.
What is the Difference Between Acetylacetoacetic Ester and Malonic Ester?
Acetylacetoacetic ester and malonic ester are not very common terms in organic chemistry because they are rarely used. The key difference between acetylacetoacetic ester and malonic ester is that acetylacetoacetic ester is the ethyl ester of the acetoacetic acid, whereas malonic ester is the ester of malonic acid.
Moreover, the synthesis processes of these chemical compounds resemble each other’s synthesis processes. Therefore, it is important to know the difference between acetylacetoacetic ester and malonic ester. The acetylacetoacetic ester synthesis process produces substituted ketones while the malonic ester synthesis process produces substituted carboxylic acid compounds. The IUPAC name of Acetylacetoacetic ester is Ethyl 3-oxobutanoate while the IUPAC name of malonic ester is propanedioic acid.
Summary – Acetylacetoacetic Ester vs Malonic Ester
Terms acetylacetoacetic ester and malonic ester are not that much common in organic chemistry because they are rarely used. The key difference between acetylacetoacetic ester and malonic ester is that acetylacetoacetic ester is the ethyl ester of the acetoacetic acid whereas malonic ester is the ester of malonic acid. The synthesis processes of these chemical compounds resemble each other’s synthesis processes; therefore it is important to know the difference between them.
Reference:
1. Kiki, et al. “The Malonic Ester Synthesis.” Master Organic Chemistry, 4 Oct. 2019, Available here.
2. “Ethyl Acetoacetate.” Wikipedia, Wikimedia Foundation, 28 June 2019, Available here.
3. “Malonic Ester Synthesis.” Wikipedia, Wikimedia Foundation, 8 Sept. 2019, Available here.
Image Courtesy:
1. “Claisen ethyl acetate” By Jesse – Own work (CC BY-SA 3.0) via Commons Wikimedia
2. “Malonic ester synthesis” By Su-no-G assumed – Own work assumed (based on copyright claims) (Public Domain) via Commons Wikimedia