6222-35-1

Usage

Uses

Used in Food Industry:
Cyclohexyl propionate is used as a flavoring agent for fruit flavors such as pineapple in beverages, candy, ice cream, and baked goods at approximately 3 ppm. It provides a fruity aroma and taste to these products, enhancing their overall flavor profile.

Preparation

By direct esterification of the alcohol with the acid in the presence of concentrated sulfuric acid or in the presence of benzene.

InChI:InChI=1/C9H16O2/c1-2-9(10)11-8-6-4-3-5-7-8/h8H,2-7H2,1H3

Upstream product

• 802294-64-0 propionic acid 
• 108-93-0 cyclohexanol 
• 107-12-0 propiononitrile 
• 110-83-8 cyclohexene 
• 74-85-1 ethene 
• 637-27-4 phenyl propionate 
• 123-62-6 propionic acid anhydride 
• 79-03-8 propionyl chloride 
• 105-37-3 Ethyl propionate 
• 201230-82-2 carbon monoxide 

Downstream Products

• 1424614-82-3 (Z)-1-cyclohexyloxy-1-(trimethylsiloxy)propene 
• 1239020-67-7 (1E)-1-cyclohexyloxy-1-(trimethylsiloxy)propene 
• 110-82-7 cyclohexane 
• 802294-64-0 propionic acid 
• 108-93-0 cyclohexanol 
• 22733-94-4 benzyl cyclohexanecarboxylate 

Relevant academic research and scientific papers

Method for preparing propionate by ester alcohol exchange

The invention discloses a method for preparing propionate by ester alcohol exchange, and relates to a method for preparing propionate. According to the invention, the method for synthesizing propionate by ester alcohol exchange of methyl propionate and various alcohols (including monohydric alcohols such as ethanol, propanol, butanol, tert-butanol, isopropanol, cyclohexanol, allyl alcohol and thelike, dihydric alcohols such as 1,3-propylene glycol and the like, glycerol and the like) is adopted, and methyl propionate and the alcohols are used as raw materials to carry out a reaction under catalysis of alkaline ionic liquid, soluble strong alkali or solid alkali to prepare higher propionate and methanol. According to the method, the synthetic route is short, and the reaction product is taken out through azeotropic extraction of the methyl propionate and methanol, so that the reaction is more thorough, and the target product is directly obtained by one step. The product obtained by thereaction only contains propionate and methanol, the whole reaction process is concise and efficient and is free of pollution, no byproducts are generated, and great significance is achieved for large-scale and low-cost production of propionate.

Consecutive addition esterification and hydrolysis of cyclic olefins catalyzed by multi-SO3H functionalized multi heteropolyanion-based ionic hybrids undersolvent-free conditions

An efficient protocol for the synthesis of cycloalkyl carboxylates and alcohols from cyclic olefins is described. The cyclic olefins were converted to corresponding target molecules under solvent-free conditions catalyzed by two novel multi-SO3H functionalized multi heteropolyanion-based ionic hybrids through one-pot consecutive addition esterification and hydrolysis reactions. This approach has several advantages, including high yield, simple workup and simple purification.

Efficient Palladium-Catalyzed Alkoxycarbonylation of Bulk Industrial Olefins Using Ferrocenyl Phosphine Ligands

The development of ligands plays a key role and provides important innovations in homogeneous catalysis. In this context, we report a novel class of ferrocenyl phosphines for the alkoxycarbonylation of industrially important alkenes. A basic feature of our ligands is the combination of sterically hindered and amphoteric moieties on the P atoms, which leads to improved activity and productivity for alkoxycarbonylation reactions compared to the current industrial state-of-the-art ligand 1,2-bis((di-tert-butylphosphino)methyl)benzene). Advantageously, palladium catalysts with these novel ligands also enable such transformations without additional acid under milder reaction conditions. The practicability of the optimized ligand was demonstrated by preparation on >10 g scale and its use in palladium-catalyzed carbonylations on kilogram scale.

An extremely efficient and green method for the acylation of secondary alcohols, phenols and naphthols with a deep eutectic solvent as the catalyst

The typical deep eutectic solvent [CholineCl][ZnCl2]3, easily prepared from choline chloride and zinc chloride, is green and useful for the acylation of secondary alcohols, phenols, and naphthols with acid anhydrides. Its efficiency allows the acylation of sterically hindered secondary alcohols and acid anhydrides to proceed in high yield under mild condition. The catalyst is cheap, easy to handle, conveniently synthesized in a single step, and recyclable for several times without significant loss of catalytic activity.

Tris(pentafluorophenyl)borane catalyzed acylation of alcohols, phenols, amines, and thiophenols under solvent-free condition

The acylation of alcohols, phenols, amines, and thiophenols was accomplished with 0.5 mol % of tris(pentafluorophenyl)borane [B(C 6F5)3] at ambient temperature under solvent-free condition. Major advantages of this method include high yield, short reaction time, simple procedure, compatibility with sensitive protecting groups as well as other functional groups, absence of racemization of optical active compounds, and epimerization of sugars.

Graphite oxide as an efficient solid reagent for esterification reactions

Esterification of organic acids with alcohols under mild conditions in high yields using graphite oxide, a readily available and inexpensive material, as an effective reagent is described.

Solvent-free transesterification in a ball-mill over alumina surface

An efficient procedure for transesterification has been developed in a ball-mill in the absence of any solvent, acid/base or metal catalyst. A variety of methyl, ethyl, allyl esters have been transesterified to higher benzyl and other esters in high yields by this procedure.

Dual behavior of alcohols in iodine-catalyzed esterification under solvent-free reaction conditions

The dual behavior phenomenon of alcohols in iodine-catalyzed esterification under solvent-free reaction conditions (SFRCs) is described; the governing factor is the stability of the carbonium ion generated from the alcohol; high concentration reaction conditions (HCRCs) or dilute solutions are much less suitable. In the case of benzylic alcohols, loss of optical activity was noted, whereas alkyl alcohols furnished a product with retention of stereochemistry.

Investigation of the Yamaguchi esterification mechanism. Synthesis of a Lux-S enzyme inhibitor using an improved esterification method

(Chemical Equation Presented) A one-pot procedure for the regioselective synthesis of aliphatic esters is described. This was a result of a study on mixed aliphatic-aromatic anhydrides. The data suggest that during the Yamaguchi esterification reaction, a symmetric aliphatic anhydride is produced in situ, which upon reaction with an alcohol yields the ester. We confirmed that benzoyl chloride could be used instead of the sterically hindered Yamaguchi acid chloride. This method was successfully applied in the synthesis of Lux-S aspartic acid inhibitor.

Steric effects in the uncatalyzed and DMAP-catalyzed acylation of alcohols - Quantifying the window of opportunity in kinetic resolution experiments

The kinetics of the reaction of several alcohols (benzyl alcohol, ethanol, 1-phenylethanol, cyclohexanol, and 1-methyl-1-phenylethanol) with a selection of anhydrides (acetic anyhydride, propionic anhydride, isobutyric anhydride, isovaleric anhydride, and pivalic anhydride) as catalyzed by 4-(N,N-dimethylamino)pyridine (DMAP)/triethyl amine have been studied in CH 2Cl2 at 20°C. In all cases the reaction kinetics can be described by rate laws containing a DMAP-catalyzed term and an uncatalyzed (back-ground) term. The rate constants for the background reaction respond sensi tively to changes in the steric demand of the alcohol and the anhydride substrates, making the reaction of cyclohexanol with acetic anhydride 526 times faster than the reaction with pivalic anhydride. Steric effects are even larger for the catalyzed reaction and the reactivity difference between acetic and pivalic anhydride exceeds a factor of 8000 for the reaction of cyclohexa nol. There is, however, no linear correlation between the steric effects on the catalyzed and the uncatalyzed part. As a consequence there are substrate combinations with dominating catalytic terms (such as the reaction of benzyl alcohol with isobutyric anhydride), while other substrate combinations (such as the reaction of cyclohexanol with pivalic anhydride) are characterized through a dominating background process. The implications of these findings for the kinetic resolution of alcohols are discussed.