Cyclopentyl methyl ether (CPME), also known as methoxycyclopentane, is a

hydrophobic In chemistry, hydrophobicity is the chemical property of a molecule (called a hydrophobe) that is seemingly repelled from a mass of water. In contrast, hydrophiles are attracted to water. Hydrophobic molecules tend to be nonpolar and, thu ...

ether solvent. A high boiling point of and preferable characteristics such as low formation of

peroxides In chemistry, peroxides are a group of compounds with the structure , where the R's represent a radical (a portion of a complete molecule; not necessarily a free radical) and O's are single oxygen atoms. Oxygen atoms are joined to each other and ...

, relative stability under acidic and basic conditions, formation of azeotropes with water coupled with a narrow explosion range render CPME an attractive alternative to other ethereal solvents such as

tetrahydrofuran Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water- miscible organic liquid with low viscosity. It is ...

(THF),

2-methyltetrahydrofuran 2-Methyltetrahydrofuran (2-MeTHF) is an organic compound with the molecular formula C5H10O. It is a highly flammable, mobile liquid. It is mainly used as a replacement for Tetrahydrofuran (THF) in specialized applications for its better performanc ...

(2-MeTHF),

dioxane Dioxane may refer to the following chemical compounds: * 1,2-dioxane * 1,3-dioxane * 1,4-dioxane {{Authority control ...

, and

1,2-dimethoxyethane Dimethoxyethane, also known as glyme, monoglyme, dimethyl glycol, ethylene glycol dimethyl ether, dimethyl cellosolve, and DME, is a colorless, aprotic, and liquid ether that is used as a solvent, especially in batteries. Dimethoxyethane is misci ...

(DME).

Synthesis

Cyclopentyl methyl ether is prepared by the addition of

methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical compound and the simplest aliphatic Alcohol (chemistry), alcohol, with the chemical formula (a methyl group linked to a hydroxyl group, often ab ...

to the

cyclopentene Cyclopentene is a chemical compound with the formula . It is a colorless liquid with a petrol-like odor. It has few applications, and thus is mainly used as a minor component of gasoline, present in concentrations of less than 1%. It is one of t ...

catalyzed by various solid acids. : Cyclopentyl methyl ether synthesis 2

In principle it could be prepared by

methylation Methylation, in the chemistry, chemical sciences, is the addition of a methyl group on a substrate (chemistry), substrate, or the substitution of an atom (or group) by a methyl group. Methylation is a form of alkylation, with a methyl group replac ...

of the

cyclopentanol Cyclopentanol or cyclopentyl alcohol is the organic compound with the formula . It is classified as a cyclic alcohol. Synthesis and reactions The bio-derived "platform chemical" furfural can be efficiently converted to cyclopentanol by hydrodeox ...

, but such a method is impractical.

Applications

Cyclopentyl methyl ether could as a solvent for

extraction Extraction may refer to: Science and technology Biology and medicine * Comedo extraction, a method of acne treatment * Dental extraction, the surgical removal of a tooth from the mouth Computing and information science * Data extraction, the ...

polymerization In polymer chemistry, polymerization (American English), or polymerisation (British English), is a process of reacting monomer molecules together in a chemical reaction to form polymer chains or three-dimensional networks. There are many fo ...

crystallization Crystallization is a process that leads to solids with highly organized Atom, atoms or Molecule, molecules, i.e. a crystal. The ordered nature of a crystalline solid can be contrasted with amorphous solids in which atoms or molecules lack regu ...

and surface coating. Some examples of reactions where it acts as a solvent are: *Reactions involving alkali agents: nucleophilic substitutions of heteroatoms (alcohols and amines) *Lewis acids-mediated reactions: Beckmann Reaction, Friedel-Crafts Reaction etc. *Reactions using Organometallic reagents or basic agents: Claisen condensation, formation of enolates or Grignard reaction. *Reduction and oxidation. *Reactions with transition metal catalysts. *Reactions with azeotropical removal of water: acetalization, etc. Cyclopentyl methyl ether possesses characteristics that make it a potential alternate for other ethers. According to an evaluation of three chemistry journals from 2020, ethereal solvents have a share of 22–25% of all solvents employed. In contrast to water-soluble ethers like tetrahydrofuran and 1,4-dioxane, cyclopentyl methyl ether (CPME) - being hydrophobic - acts suitably as an

extractant Extraction in chemistry is a separation process consisting of the separation of a substance from a matrix. The distribution of a solute between two phases is an equilibrium condition described by partition theory. This is based on exactly ho ...

. In aqueous phases, only trace amounts of CPME remain due to its low solubility. CPME also exhibits stability at both low and high pH levels, even under elevated temperatures and extended contact times. It can form an

azeotrope An azeotrope () or a constant heating point mixture is a mixture of two or more liquids whose proportions cannot be changed by simple distillation.Moore, Walter J. ''Physical Chemistry'', 3rd e Prentice-Hall 1962, pp. 140–142 This happens beca ...

with water in a ratio of 83.7% CPME to 16.3% water at an azeotropic end temperature of 83 °C. These properties enable CPME to function effectively as an entrainer during

esterification In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

processes and acetalizations. The solvent also displays low solubility for water in CPME, reported to be 0.3 g / 100 g. Cyclopentyl methyl ether is touted as an eco-friendly solvent in a wide range of still other processes, such as

reductions Reductions (, also called ; ) were settlements established by Spanish rulers and Roman Catholic missionaries in Spanish America and the Spanish East Indies (the Philippines). In Portuguese-speaking Latin America, such reductions were also ...

oxidation Redox ( , , reduction–oxidation or oxidation–reduction) is a type of chemical reaction in which the oxidation states of the reactants change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is ...

s, and

Grignard reaction The Grignard reaction () is an organometallic chemical reaction in which, according to the classical definition, carbon alkyl, allyl, vinyl, or aryl magnesium halides (Grignard reagent) are added to the carbonyl groups of either an aldehyde or ...

References

{{reflist Ethers Ether solvents Cyclopentyl compounds