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Methyl Cyclopentenolone CAS 80-71-7

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  • Appearance: White powder
  • Purity: 99. 0%min
  • Stock: In stock
  • Sample: Available
  • Zhishang Chemical: Methyl Cyclopentenolone Supplier & Manufacturer

Basic Info

What is Methyl Cyclopentenolone?

Methyl cyclopentenolone is common in natural ingredients and is widely used. Its flavor is similar to cooked syrup and maple syrup. It is usually used in brown or nutty flavors and is added in high amounts.

Methyl cyclopentenolone has more aliases than almost any other flavor chemical. Like many other chemicals with similar structures, it exists as a keto-enol tautomer and can also exist as 3-methyl-1,2-cyclopentanedione as the name of the keto form. This name is very common. There are other widely used names such as maple lactone, cyclotene and corylone.

Methyl Cyclopentenolone Uses

  1. GB 2760-1996 stipulates that it is a permitted edible flavor. It is mainly used to prepare maple, smoked tobacco, butterscotch and apricot flavors.
  2. Methyl cyclopentenolone can be used as an analytical reference standard for quantifying analytes in commercial products using different chromatographic techniques.
  3. Methyl cyclopentenolone is one of the flavor compounds of maple syrup, coffee oil and wood smoke. It is reported to be one of the key aroma compounds in Wasanbon sugar, contributing to the maple syrup-like flavor. Methylcyclopentenolone is also one of the main volatile compounds formed during the thermal degradation of glucose.
  4. Methyl cyclopentenolone is a flavoring agent in the form of a white crystalline powder. It has a nutty odor and emits a maple licorice aroma when diluted. It is soluble in alcohol and propylene glycol, slightly soluble in most fixed oils, and slightly soluble in water. It is obtained by synthesis. It is also known as 3-methyl-cyclopentane-1,2-dione.

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References

Application of Methyl Cyclopentenolone

Preparation of Methyl Cyclopentenolone

  • Diethyl oxalate method
    Strunz et al. mixed diethyl oxalate and dimethyl glutarate, heated them under reflux reaction under the catalysis of sodium methoxide, then mixed them with dimethyl glutarate and heated them for reaction, and finally used potassium iodide for addition reaction. MCP was obtained by decarboxylation with 42% phosphoric acid solution, and the total yield of the product was 80%. This method uses a one-pot reaction, which is easy to operate, but the reaction time is extremely long, and iodomethane is used as a reactant, which is costly and not conducive to industrial production. MCP was synthesized using diethyl oxalate, ethyl propionate, ethyl acrylate, anhydrous ether, N,N-dimethyldiformamide, concentrated hydrochloric acid, sodium metal, phosphoric acid, ethyl acetate, anhydrous ethanol, etc., and the total yield of the product was 51.09%. Under the catalysis of sodium ethoxide, ethyl propionate and diethyl oxalate react under anhydrous conditions at 60°C, and the obtained Claisen condensation product 2-methyl-3-carbonyl-succinic acid diethyl ester reacts with ethyl acrylate at 80°C, and finally 50% phosphoric acid is used as a catalyst to hydrolyze at 90-100°C to obtain methylcyclopentenol ketone. Although this process avoids the use of expensive methyl iodide, the reaction time is still long, and the reaction involves the use of metallic sodium, which increases the risk of production.
  • 2,5-Hexanedione method
    2,5-hexanedione can be used to react with 1% w/v NaOH solution to obtain 3-methyl-2-cyclopentene-1-one, but the conversion rate of the reactants is not ideal, and 20% of 2,5-hexanedione is still detected after the reaction. Later, this method was improved, and 3-methyl-2-cyclopentene-1-one was prepared by reacting 0.076% w/v NaOH solution under high temperature conditions. Methylcyclopentenol ketone is prepared by oxidizing 3-methyl-2-cyclopentene-1-one with H2O2 under alkaline conditions and hydrolyzing it with acid. This process involves high temperature and oxidation reaction, which increases the risk of production, and the raw material cost is not low, which is not suitable for industrial production.
  • 2-Methylfuran method
    Formaldehyde aqueous solution, dimethylamine aqueous solution and 2-methylfuran are heated under weak acidic conditions (pH4-5) to obtain the Mannich reaction product N, N-dimethyl-5-methylfurfurylamine. Then, N, N-dimethyl-5-methylfurfurylamine is catalyzed by dilute hydrochloric acid to react with ring-opening rearrangement at 98-100°C, and then the pH is adjusted to 12-13 and reacted at 70-80°C to obtain 1-dimethylamino-2,5-hexanedione. Finally, methylcyclopentenol ketone can be obtained by hydrolysis and recrystallization. The raw materials of this process are cheap and easy to obtain, and the operation is simple. It has been industrialized in China. However, the raw materials are highly toxic, a large amount of irritating gases are produced during the reaction, and a large amount of wastewater is produced. How to deal with the pollution caused by the production process to the environment is a difficult problem of this process.
  • Dimethyl adipate method
    First, adipic acid and methanol or ethanol are used to prepare adipic acid diester, and the adipic acid diester undergoes a Dieckmann condensation reaction to obtain cyclopentane-2-ketoate. Under alkaline conditions, it reacts with a methylating agent to obtain 2-methylcyclopentane-2-ketoate. Finally, it undergoes oxychlorination and hydrolysis and decarboxylation under acidic conditions to obtain methylcyclopentenol ketone. The raw materials of this process are cheap and easy to obtain, and industrial production has been carried out. However, chlorine needs to be introduced into the production process for chlorination reaction, and the control requirements for temperature and water content of the entire reaction system are high: if the temperature is too high, side reactions will occur and the product yield will be reduced; if the temperature is too low, the reaction will be incomplete, and a large amount of chlorine will escape when the solvent is recovered, and a large amount of water and alkali solution will be consumed to absorb and neutralize the waste gas, which greatly increases the cost of waste gas recovery and the discharge of wastewater.
  • Isoprene method
    The process of preparing MCP using isoprene as raw material. The process uses trimethylbenzyl ammonium chloride to catalyze the reaction of isoprene and chloroform to synthesize 1,1-dichloro-2-methyl-2-vinylcyclopropane. 1,1-dichloro-2-methyl-2-vinylcyclopropane is rapidly cooled and rearranged after 9 high-temperature cracking to obtain 1-methyl-4,4-dichlorocyclopent-1-ene, which is then hydrolyzed into 3-methyl-2-cyclopentene-1-one under acidic conditions. Finally, methylcyclopentenol ketone can be obtained by oxidative hydrolysis of 3-methyl-2-cyclopentene-1-one. The process has many steps, complex and difficult operation, involves high-temperature cracking and rapid cooling, consumes a lot of energy, and is not conducive to industrial production.
  • 2-Ethoxyacetaldehyde method
    Using 2-ethoxyacetaldehyde as raw material, thiazolium salt is used to catalyze the reaction with butenone under alkaline conditions to obtain 1-ethoxy-2,5-dihexanone, and then 2-ethoxy-3-methylcyclopent-2-enone is obtained through intramolecular condensation, and finally methylcyclopentenol ketone is obtained through acid hydrolysis. This process requires solvent extraction and brine washing, which has high production costs and produces a lot of waste brine and waste acid. How to treat wastewater and recycle solvents is a difficult problem of this process.
  • 2-Methylcyclopentanone method
    Using 2-methylcyclopentanone and isopropyl nitrite under acidic conditions, 2-methylcyclopentanone is nitrosated to obtain 3-methyl-1,2-cyclopentanone monoxime. 3-methyl-1,2-cyclopentanone monoxime is hydrolyzed under acidic conditions to obtain methylcyclopentenol ketone. The raw materials used in this process are cheap and easily available, the reaction conditions are mild, the process operation is simple and the yield is high, and the industrialization prospect is good. However, the hydrolysis reaction produces a lot of waste acid, waste water and waste salt. How to solve the environmental protection problem is the difficulty of this process.

References

Methyl Cyclopentenolone Supplier and Manufacturer

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