Abstract

A process for making menthyl glutarate is disclosed. The process comprises reacting excess glutaric acid and menthol to produce a mixture comprising monomenthyl glutarate (MMG) and dimenthyl glutarate (DMG), wherein the weight ratio of glutaric acid to menthol is from 1.0 to 1.6 and the resulting mixture comprises from 60 to 70 wt. % of MMG and from 30 to 40 wt.% of DMG

IPC Classes  ?

• C07C 67/08 - Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
• C07C 69/42 - Glutaric acid esters

Abstract

A method of imparting a physiological cooling effect to a consumer product is disclosed. The method comprises formulating into the consumer product a composition comprising at least one lactoyl ester of menthyl lactate. Also disclosed is a method of providing physiological cooling by contacting skin or mucous membranes with the lactoyl ester compositions. Coolants comprising the lactoyl esters and additional coolants are also disclosed. The lactoyl esters are conveniently prepared from menthol and lactic acid.

IPC Classes  ?

• A61K 8/37 - Esters of carboxylic acids
• A61Q 5/00 - Preparations for care of the hair
• A61Q 11/00 - Preparations for care of the teeth, of the oral cavity or of dentures, e.g. dentifrices or toothpastesMouth rinses
• A61Q 11/02 - Preparations for deodorising, bleaching or disinfecting dentures
• A61Q 13/00 - Formulations or additives for perfume preparations

Abstract

A practical, economical process for making tricyclodecenyl esters is disclosed. After reacting a lower carboxylic acid and a dicyclopentadiene in the presence of triflic acid to form the ester, the reaction mixture is distilled in the presence of a base to isolate a fragrance-quality tricyclodecenyl ester. Adding enough base to neutralize the triflic acid enables a distillation-only purification, facilitates starting material recovery, and avoids drawbacks of a basic workup.

IPC Classes  ?

• C07C 67/04 - Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
• C07C 69/013 - Esters of alcohols having the esterified hydroxy group bound to a carbon atom of a ring other than a six-membered aromatic ring

Abstract

A method for stabilizing menthyl lactate is disclosed. The method comprises combining water with a solution comprising menthyl lactate and a water-miscible organic solvent in amounts effective to precipitate menthyl lactate from the resulting aqueous mixture. The aqueous precipitation method is simple to practice, and it provides menthyl lactate having remarkably improved storage stability.

IPC Classes  ?

• C07C 67/52 - SeparationPurificationStabilisationUse of additives by change in the physical state, e.g. crystallisation
• C07C 69/68 - Lactic acid esters

Abstract

A process for making terpene esters is disclosed. Reaction of a terpene alcohol with acetic anhydride in the presence of a high-boiling amine provides a terpene ester. Acetic acid, which is distilled from the reaction mixture as it forms, can be recovered. The terpene ester is distilled from the high-boiling amine to provide a product that is substantially free of nitrogen-containing impurities. The reaction mixture can be reused for subsequent acylations. The simple, economical process gives high-quality terpene esters while avoiding waste-disposal issues of other common acylation procedures.

IPC Classes  ?

• C07C 67/08 - Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
• C07C 69/145 - Acetic acid esters of monohydroxylic compounds of unsaturated alcohols

Abstract

A two-step aldol condensation process is disclosed. α-Campholenic aldehyde (ACA) and methyl ethyl ketone (MEK) react in the presence of a base under conditions effective to produce a mixture comprising a high yield of ketol condensation products. Dehydration of the ketols in the presence of an organic sulfonic acid provides unsaturated ketones that are valuable intermediates for fragrance components for synthetic sandalwood products. Compared with the usual one-step, base-catalyzed approach, the two-step process increases the yield of all condensation products and maximizes production of the most valuable ketone isomers.

IPC Classes  ?

• C07C 45/66 - Preparation of compounds having C=O groups bound only to carbon or hydrogen atomsPreparation of chelates of such compounds by reactions not involving the formation of C=O groups by splitting-off hydrogen atoms or functional groupsPreparation of compounds having C=O groups bound only to carbon or hydrogen atomsPreparation of chelates of such compounds by reactions not involving the formation of C=O groups by hydrogenolysis of functional groups by dehydration
• C07C 45/72 - Preparation of compounds having C=O groups bound only to carbon or hydrogen atomsPreparation of chelates of such compounds by reactions not involving the formation of C=O groups by isomerisationPreparation of compounds having C=O groups bound only to carbon or hydrogen atomsPreparation of chelates of such compounds by reactions not involving the formation of C=O groups by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing C=O groups with the same or other compounds containing C=O groups
• C07C 45/74 - Preparation of compounds having C=O groups bound only to carbon or hydrogen atomsPreparation of chelates of such compounds by reactions not involving the formation of C=O groups by isomerisationPreparation of compounds having C=O groups bound only to carbon or hydrogen atomsPreparation of chelates of such compounds by reactions not involving the formation of C=O groups by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing C=O groups with the same or other compounds containing C=O groups combined with dehydration
• C07C 45/82 - SeparationPurificationStabilisationUse of additives by change in the physical state, e.g. crystallisation by distillation
• C07C 49/21 - Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing rings other than six-membered aromatic rings
• C07C 49/242 - Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups containing rings other than six-membered aromatic rings

Abstract

Clear aqueous compositions comprising water, a hydrophobic organic compound, and from about 2 to about 50 wt.% of a solubilizer are disclosed. The solubilizer is an alkali metal or alkaline earth metal salt of a monoester of a saturated C6-C20 alcohol and a saturated dicarboxylic acid. The monoester salts are remarkably effective for solubilizing a wide variety of hydrophobic organic compounds in water to provide aqueous compositions that have excellent stability and outstanding clarity. The compositions are valuable for the cosmetic, agrochemical, coatings, pharmaceutical, and flavor & fragrance industries.

IPC Classes  ?

• A61K 8/37 - Esters of carboxylic acids
• A61K 8/67 - Vitamins
• A61Q 13/00 - Formulations or additives for perfume preparations
• A61Q 19/00 - Preparations for care of the skin

Abstract

A process for making tricyclodecenyl esters is disclosed. A C2-C4 carboxylic acid and a dicyclopentadiene react in the presence of triflic acid under conditions effective to produce the ester. The process gives tricyclodecenyl esters in good yield while avoiding the need to use a large excess of the carboxylic acid. The process efficiently provides fragrance-quality tricyclodecenyl esters from technical grade dicyclopentadienes and/or recycled carboxylic acids.

IPC Classes  ?

• C07C 67/04 - Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
• C07C 69/013 - Esters of alcohols having the esterified hydroxy group bound to a carbon atom of a ring other than a six-membered aromatic ring

Abstract

Cyclic ethers or chloroketones useful as fragrance components or intermediates are made by reacting a saturated, tertiary terpene alcohol with hypochloric acid under conditions effective to promote oxidation. trans-Pinanol gives predominantly 6,9-dimethyl-7-oxatricyclo⏧4.3.0.03,9]-nonane, while cis-pinanol yields almost exclusively 1-acetyl-3-(2-chloroethyl)-2,2-dimethyl-cyclobutane, a new and versatile intermediate for making cyclobutane derivatives having interesting and diverse aromas.

IPC Classes  ?

• C07C 29/00 - Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
• C07C 31/27 - Polyhydroxylic alcohols containing saturated rings
• C07C 45/27 - Preparation of compounds having C=O groups bound only to carbon or hydrogen atomsPreparation of chelates of such compounds by oxidation
• C07C 49/15 - Ketones containing more than one keto group containing rings

Abstract

A process for making monomenthyl esters of dicarboxylic acids is disclosed. Menthol reacts with a saturated, cyclic anhydride in the presence of a base catalyst / selected from the group consisting of alkali metal or alkaline earth metal salts, oxides, hydroxides, and mixtures thereof, under conditions effective to produce a mixture of mono- and bis-menthyl esters in which the molar ratio of mono- to bis-menthyl esters is enhanced compared with the ratio of esters produced in a similar uncatalyzed process.

IPC Classes  ?

• C07C 67/08 - Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
• C07C 69/40 - Succinic acid esters
• C07C 69/42 - Glutaric acid esters
• C07C 69/44 - Adipic acid esters

Abstract

A simple, high-yield process for making menthyl lactate (ML) is disclosed. Menthol and lactic acid react to produce a mixture comprising menthyl lactate and one or more higher lactoyl esters of ML. Hydrolysis of the esterification mixture follows in the presence of aqueous base under conditions effective to convert the higher lactoyl esters to menthyl lactate. Coincidentally, the conditions minimize hydrolysis of menthyl lactate to menthol, thereby maximizing the overall yield of ML.

IPC Classes  ?

• C07C 67/08 - Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
• C07C 67/30 - Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
• C07C 69/68 - Lactic acid esters