Malonic acid powder appears as a white, crystalline solid that is odorless or has a faint, pleasant acetic acid-like odor. It is a dicarboxylic acid, meaning it contains two carboxyl (-COOH) groups attached to a central carbon atom, giving it the ability to form salts and esters. This substance has hygroscopicity and, if exposed to air, may absorb moisture and cause the color to darken. The melting point is relatively high, at 136.3 ℃. This means that at this temperature, propanedioic acid will transform from solid to liquid. This characteristic enables its application in chemical experiments that require long-term stability. It is a strong organic acid with irritating and corrosive properties. The methylene group in the molecule can undergo various types of reactions due to the activation of two carboxyl groups. The method of hydrolyzing cyanoacetic acid or diethyl malonate is commonly used in industry to produce Malonic acid Due to the instability of itself, its application in organic synthesis is carried out through diethyl malonate.
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| C,F | C3H4O4 |
| E,M | 104.01 |
| M,W | 104.06 |
| m/z | 104.01 (100.0%), 105.01 (3.2%) |
| E,A | C, 34.63; H, 3.87; O, 61.50 |
Aluminum cleaning:
During the processing of aluminum materials, the surface is often contaminated with various stains and impurities, such as grease, wax, dust, etc. These impurities can affect the surface quality and usability of aluminum materials, so cleaning is necessary. Malonic acid powder can serve as an effective cleaning agent to remove these stains and impurities from the surface of aluminum materials. The principle of its action is to utilize the acidic nature of it to react chemically with stains and impurities, causing it to separate from the surface of aluminum material.
Aluminum passivation:
Passivation is an important process for surface treatment of aluminum materials, which can enhance their corrosion resistance. As an acidic medium, can promote the passivation reaction on the surface of aluminum materials. Under the action, a dense oxide film is formed on the surface of aluminum, which can effectively prevent further oxidation of aluminum and improve its corrosion resistance.
Aluminum polishing:
Polishing is a common process for surface treatment of aluminum materials, which can enhance their appearance and glossiness. It can be used as a polishing agent to help achieve the polishing treatment of aluminum materials. Its working principle is to utilize the acidic properties to chemically react with the surface of aluminum, making it smoother and smoother. At the same time, it can also remove oxides and impurities on the surface of aluminum materials, further improving the polishing effect.
Aluminum dyeing:
Dyeing is an important process for surface treatment of aluminum materials, which can present various colors and patterns. It can serve as a dyeing aid to help achieve the dyeing treatment of aluminum materials. The principle of its action is to utilize the acidic properties to chemically react with the dye, promoting the adsorption and distribution of the dye on the surface of aluminum, thereby enhancing the dyeing effect.
Aluminum coating:
Painting is a common process for surface treatment of aluminum materials, which can enhance their protective performance and aesthetics. It can be used as a coating additive to help achieve the coating treatment of aluminum materials. Its working principle is to utilize the acidic nature of it to react chemically with the coating material, promoting the adhesion and solidification of the coating material on the surface of aluminum. At the same time, it can also remove oxides and impurities on the surface of aluminum materials, further improving the coating effect.
Environmental performance:
It is a relatively environmentally friendly chemical substance that has little impact on the environment during production and use. Therefore, using it as an aluminum surface treatment agent will not cause serious environmental pollution. In addition, it can also be naturally decomposed into carbon dioxide and water through biodegradation, further reducing its impact on the environment.
Malonic acid powder participates in a wide range of chemical reactions, including hydrolysis (indirectly through its precursor), decarboxylation, condensation, oxidation-reduction, esterification, and amidation.
Its unique reactivity makes it a valuable intermediate in organic synthesis and a tool in biochemical research.
1. Hydrolysis Of Maleic Anhydride
While itself does not directly undergo hydrolysis, its precursor, maleic anhydride (not to be confused with Malonic acd), undergoes hydrolysis to form Malonic acd. Maleic anhydride, upon reacting with water, undergoes a hydration reaction to yield it and carbon dioxide. This reaction is used industrially to produce the product.
2. Decarboxylation Reactions
It is known to undergo decarboxylation reactions, where it loses a carboxyl group (COOH) along with its attached carbon atom, resulting in the formation of shorter carbon chain compounds. For example, in the presence of heat or certain catalysts, it can decarboxylate to yield acetic acid.
3. Condensation Reactions
It is a versatile building block in organic synthesis, particularly in the field of carbonyl chemistry. It undergoes condensation reactions with various aldehydes and ketones in the presence of bases like sodium hydroxide or ammonia, leading to the formation of β-keto acids. This reaction, known as the Malonic ester synthesis, is a powerful tool in the synthesis of carboxylic acids with various functional groups.
4. Oxidation And Reduction Reactions
As an organic acid, it can participate in oxidation and reduction reactions. Oxidation of it can yield various products depending on the conditions and oxidizing agents used. Similarly, reduction of it can lead to the formation of alcohols or other reduced forms.
5. Esterification And Amidation
It readily forms esters and amides upon reaction with alcohols and amines, respectively. These reactions are catalyzed by acids or bases and are important in the synthesis of it derivatives with specific functional groups. Esters of it are commonly used as intermediates in organic synthesis.
6. Inhibition Of Enzymatic Reactions
Due to its structural similarity to succinic acid, acts as an inhibitor of enzymes involved in the citric acid cycle, particularly succinate dehydrogenase. This inhibitory activity can be used to study the mechanisms of these enzymes and their role in cellular metabolism.
Prepared from acetic acid as raw material. Acetic acid reacts with chlorine gas to obtain chloroacetic acid, which is then treated with sodium carbonate to produce a sodium salt. It undergoes nucleophilic substitution reaction with sodium cyanide to obtain cyanoacetic acid. Sodium hydroxide solution hydrolyzes, the cyanide group is converted into carboxylate ions, and then acidified to obtain succinic acid.
Acetic acid reacts with chlorine gas, and the hydroxyl group in the acetic acid molecule (in fact, the functional group in acetic acid is carboxyl, but here we focus on the active site that reacts with chlorine gas, which is the hydrogen atom on the carbon connected to the carboxyl group in the acetic acid molecule. Although the statement "hydroxyl group is replaced" may be misleading, the core meaning is that one hydrogen atom in acetic acid is replaced by a chlorine atom) is replaced by a chlorine atom, producing chloroacetic acid.
The chemcal equation can be expressed as:
CH3COOH+Cl2 → CH2ClCOOH+HCl (note: this equation is a schematic representation, and the actual reaction may involve more complex mechanisms and by-products).
Chloroacetic acid reacts with sodium carbonate to produce sodium chloroacetate and sodium bicarbonate (or carbon dioxide and water, depending on reaction conditions and the amount of sodium carbonate used).
The chemcal equation can be expressed as:
CH2ClCOOH+Na2CO3→CH2ClCOONa+NaHCO3
(Or generate CO2 and H2O, depending on the conditions).
Sodium chloroacetate undergoes nucleophilic substitution reaction with sodium cyanide. Sodium cyanide acts as a nucleophilic reagent to attack the chlorine atom in sodium chloroacetate, replacing it with a cyanide group to produce cyanoacetic acid and sodium chloride.
The chemcal equation can be expressed as:
CH2ClCOONa+NaCN→CH2CNCOONa+NaCl
(During subsequent hydrolysis, CH2CNCOONa will decompose into cyanoacetic acid and NaOH, but this step will be described together here).
Cyanoacetic acid is hydrolyzed in sodium hydroxide solution, and the cyanide group is hydrolyzed to carboxyl group under alkaline conditions, while generating ammonia gas (or ammonium salt, depending on reaction conditions) and sodium malonate.
The chemcal equation can be expressed as (stepwise representation):
CH2CNCOOH+2NaOH → CH2 (COONa) COONa+NH3 ↑ (or generates NH4+and OH −).
Acidify the sodium malonate solution obtained in the previous step, neutralize the base in the solution by adding acid (such as hydrochloric acid), convert sodium malonate to Malonic acid powder, and precipitate it.
The chemical equation can be expressed as: CH2 (COONa) 2+2HCl → CH2 (COOH) 2+2NaCl (precipitation of succinic acid).
Please note that the above chemical equations are schematic representations, and actual reactions may involve more complex mechanisms, by-products, and reaction conditions. In industrial production, factors such as reaction selectivity, yield, safety, and environmental protection also need to be considered.
Frequently Asked Questions
What is malonic acid used for?
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Malonic acid is used for the preparation of cinnamic acid, a compound used for the formation of cin metacin which is an anti-inflammatory. The malonates are used in syntheses of B1 and B6, barbiturates, and several other valuable compounds. It is used in cosmetics as a buffering and as a flavouring agent in food.
Is malonic acid safe?
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Water soluble. SYMPTOMS: Symptoms of exposure to this compound include irritation of the skin, eyes, mucous membranes and upper respiratory tract. It can damage the skin and mucous membranes. No information available.
Will malonic acid dissolve in water?
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Malonic acid is a white crystalline solid with a decomposition point of ≈135 °C. It is highly soluble in water and oxygenated solvents.
How to make malonic acid?
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Malonic acid has been prepared by the hydrolysis of malononitrile with concentrated hydrochloric acid;2 by the hydration of carbon suboxide;3 and from an alkali cyanide and ethyl bromoacetate,4 ethyl chloroacetate,5 or chloroacetic acid6 followed by hydrolysis.
What is another name for malonic acid?
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Malonic acid is also known as Propanedioic Acid or Dicarboxymethane. The name is derived from a Greek word Malon which means apple. Malonates are the ionized form of malonic acid, along with its esters and salts. It appears as a white crystal or crystalline powder.
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