626-77-7

Usage

Uses

Used in Fragrance Industry:
Caproic acid propyl ester is used as a fragrance ingredient for its ability to replicate fruit scents, adding a pleasant aroma to various products such as perfumes, cosmetics, and air fresheners.
Used in Solvent Applications:
Caproic acid propyl ester is used as a solvent for polar compounds due to its ability to dissolve a wide range of substances, making it suitable for use in various industries such as pharmaceuticals, chemicals, and cleaning products.

Preparation

By esterification of hexanoic acid with propyl alcohol in benzene solution in the presence of p-toluenesulfonic acid.

InChI:InChI=1/C9H18O2/c1-3-5-6-7-9(10)11-8-4-2/h3-8H2,1-2H3

Upstream product

• 71-23-8 propan-1-ol 
• 142-61-0 Hexanoyl chloride 
• 142-62-1 hexanoic acid 
• 30504-40-6 propyl ester of tetraethyldiamidophosphorus acid 
• 106-70-7 methyl hexanoate 
• 6140-80-3 3-isopropoxyprop-1-ene 
• 1471-03-0 allyl propyl ether 
• 4485-09-0 nonan-4-one 

Downstream Products

• 71-23-8 propan-1-ol 
• 142-62-1 hexanoic acid 
• 187737-37-7 propene 
• 927-49-1 dipentyl ketone 
• 6378-65-0 n-hexyl caproate 
• 111-27-3 hexan-1-ol 

Relevant academic research and scientific papers

Fully recyclable Br?nsted acid catalyst systems

Homogeneous and heterogeneous sulfonic acid catalysts are some of the most common catalysts used in organic chemistry. This work explores an alternative scheme using a fully recyclable polymeric solvent (a poly-α-olefin (PAO)) and soluble PAO-anchored polyisobutylene (PIB)-bound sulfonic acid catalysts. This PAO solvent is nonvolatile and helps to exclude water by its nonpolar nature which in turn drives reactions without the need for distillation of water, avoiding the need for excess reagents. This highly nonpolar solvent system uses polyisobutylene (PIB) bound sulfonic acid catalysts that are phase-anchored in solvents like PAO. The effectivenes of these catalysts was demonstrated by their use in esterifications, acetalizations, and multicomponent condensations. These catalysts and the PAO solvent phase show excellent recyclability in schemes where products are efficiently separated. For example, this non-volatile polymeric solvent and the PIB-bound catalyst can be recycled quantitatively when volatile products are separated and purified by distillation. In other cases, product purification can be effected by product self-separation or by extraction.

Genome mining reveals new bacterial type I Baeyer-Villiger monooxygenases with (bio)synthetic potential

Baeyer-Villiger monooxygenases (BVMOs) are oxidorreductases that catalyze the oxidation of ketones in a very selective manner. By genome mining we detected seven putative type I BVMOs in Bradyrhizobium diazoefficiens USDA 110. As we established the phylogenetic relationships among them and with other type I BVMOs, we found out that they belong to different clades of the phylogenetic tree. Thus, we decided to clone and heterologously express five of them. Three of them, each one from a divergent phylogenetic group, were obtained as soluble proteins, allowing us to proceed with their biocatalytic assessment and enzymatic characterization. As to substrate scope and selectivity, we observed a complementary behavior among the three BVMOs. BVMO2 was the more versatile biocatalyst in whole-cell systems while BVMO4 and BVMO5 showed a narrow substrate profile with preference for linear ketones and particular regioselectivity for (±)-cis-bicyclo[3.2.0]hept-2-en-6-one.

Selective Monoesterification of Symmetrical Diols Using Resin-Bound Triphenylphosphine

Coupling reactions to make esters and amides are among the most widely used organic transformations. We report efficient procedures for amide bond formation and for the monoesterification of symmetrical diols in excellent yields without any requirement for high dilution or slow addition using resin-bound triarylphosphonium iodide. Easy purification, low moisture sensitivity, and good to excellent yields of the products are the major advantages of this protocol.

Optimized synthesis of (Z)-3-hexen-1-yl caproate using germinated rapeseed lipase in organic solvent

(Z)-3-hexen-1-yl esters are important green top-note components of food flavors and fragrances. Effects of various process conditions on (Z)-3-hexen-1-yl caproate synthesis employing germinated rapeseed lipase acetone powder in organic solvent were investigated. Rapeseed lipase catalyzed ester formation more efficiently with non-polar compared to polar solvents despite high enzyme stability in both types of solvents. Maximum ester yield (90%) was obtained when 0.125 M (Z)-3-hexen-1-ol and caproic acid were reacted at 25 °C for 48 h in the presence of 50 g/L enzyme in heptane. Enzyme showed little sensitivity towards aw with optimum yield at 0.45, while added water did not affect ester yield. Esterification reduced by increasing molecular sieves (>0.0125%, w/v). The highest yields of caproic acid were obtained with isoamyl alcohol (93%) followed by butanol and (Z)-3-hexen-1-o1 (88%) respectively reflecting the enzyme specificity for straight and branched chain alcohols. Secondary alcohols showed low reactivity, while tertiary alcohol had either very low reactivity or not esterified at all. A good relationship has been found between ester synthesis and the solvent polarity (log P value); while no correlation for the effect of solvents on residual enzyme activity was observed. It may be concluded that germinated rapeseed lipase is a promising biocatalyst for the synthesis of valuable green flavor note compound. The enzyme also showed a wide range of temperature stability (5-50 °C).

The application of N,N′dibromo-N,N′-1,2-ethanediyl bis(P-toluenesulfonamide) as a powerful reagent for conversion of carboxylic acids into esters and amides with triphenylphosphine

In the presence of equivalent amounts of triphenylphenylphosphine and N,N′-dibromo-N,N′-1,2-ethanediylbis(p-toluenesulphonamide) ester and amide compounds can be generated in high yields from the corresponding carboxylic acid and alcohols or amines.

Group 5 and group 6 metal halides as very efficient catalysts for acylative cleavage of ethers

Group 5 and 6 metal chlorides such as MoCl5, WCl6, NbCl5 and TaCl5 were found as very efficient catalysts for acylative cleavage of the C-O bond of ethers. Compared with conventional Lewis acid catalysts such as ZnCl2, AlCl3, SnCl4 and TiCl4, group 5 and 6 metal chlorides showed better results in the catalytic C-O bond cleavage of dibutyl ether with benzoyl chloride.

Catalytic C-O bond cleavage of ethers using group 5 or 6 metal halide/acid chloride systems

Ethers reacted with acid chlorides in the presence of a catalytic amount of MCl5/6 (M = Mo, W, Nb or Ta) to give esters in 75-98% yield; a stoichiometric reaction of dioctyl ether with MoCl5 afforded 1-chlorooctane in 93% yield and addition of benzoyl chloride to the resulting mixture gave octyl benzoate in 49% yield.

Propanolysis of esters using chlorotrimethylsilane

A variety of methyl esters are converted into the corresponding propyl esters upon treatment with 1-propanol and chlorotrimethylsilane. Among them acyclic aliphatic esters have the best conversion rate.

THERMAL ESTERIFICATION OF CARBOXYLIC ACIDS WITH ALCOHOLS

Catalyst-free esterification of carboxylic acids with alcohols has been studied, and the optimal process conditions have been determined.

Determination of Organic Acid Structure Effect on the Equilibrium Constant of Esterification

Equilibrium constants of esterification were measured using both static and dynamic methods.Simultaneously, the measured rate constants of the organic acids esterifications with propanol and the rate constants of propylesters hydrolysis were correlated by the Taft's-equation.It was found, that the equilibrium constant of this reaction does not depend on the structure of the organic acid, and has for T = 60 deg C the value 3.96 +/- 0.08.