A method for purification and extraction of cannabinoids includes: providing a cannabis oil including phospholipids and cannabinoid acids; contacting the cannabis oil with a degumming solvent, wherein the degumming solvent and cannabis oil are substantially immiscible; and separating an aqueous phase including the degumming solvent and at least a portion of the phospholipids from an oil phase including the cannabis oil. The method may further include contacting the oil phase with an extraction solvent, where the extraction solvent and oil phase are substantially immiscible; and separating an aqueous phase including the extraction solvent and at least a portion of the cannabinoid acids from a second oil solvent phase including the oil phase and/or simply the liberated cannabinoids following acidification of the extraction solvent.

Naphthenate deposition is formed from tetraprotic naphthenic acids having aliphatic chains and high molecular weight, provided with four carboxylic terminations, sometimes called ARN acids. Obtaining these species from their matrix of origin requires the prior use of sample preparation methods aiming at an efficient extraction of naphthenic acids. Obtaining ARN acids from naphthenate deposits is advantageous in the potential for reusing waste and reducing environmental damage. The process also adds value to waste materials from the oil production and exploration process.

The present invention relates to the field of laboratory-scale sample preparation, which describes a methodology for the specific isolation of tetraprotic naphthenic acids, called ARN acids, from residual naphthenate deposits from petroleum production.

The method consists of cleaning the naphthenate deposit, converting the naphthenate salts to naphthenic acids and isolating the ARN acids from the other organic acids, using a silica-based sorbent material with aminopropyl functional groups, previously selected for an efficient elution of different functional groups and polarities.

The results of ESI(−)-FT-ICR MS showed that the methodology is promising because it provided an excellent separation by difference in polarity and as a function of different molecular weight ranges, thus reducing the complexity of the organic acid extract obtained from the naphthenate deposit. Furthermore, it allowed the separation of the different acidic species that were present in the sample. The results of ESI(−)-FT-ICR MS also indicated that one of the fractions concentrated into ARN acids, including discharged species and especially ARN acids in the form of monocharged ions. The ESI(−)-Orbitrap MS data corroborated those obtained by ES(−)-FT-ICR MS, making consistent the statement that the extract obtained from the naphthenate deposit contains a mixture of acids and that the fractionation developed provided the isolation of ARN acids from naphthenate deposits. Furthermore, the integrations of the .sup.1H NMR spectra of acidic fractions as a function of molecular weight highlighted the expressive presence of alkyl compounds and absence of aromatic hydrogens in the fraction of interest.

Naphthenate deposition is formed from tetraprotic naphthenic acids having aliphatic chains and high molecular weight, provided with four carboxylic terminations, sometimes called ARN acids. Obtaining these species from their matrix of origin requires the prior use of sample preparation methods aiming at an efficient extraction of naphthenic acids. Obtaining ARN acids from naphthenate deposits is advantageous in the potential for reusing waste and reducing environmental damage. The process also adds value to waste materials from the oil production and exploration process.

The present invention relates to the field of laboratory-scale sample preparation, which describes a methodology for the specific isolation of tetraprotic naphthenic acids, called ARN acids, from residual naphthenate deposits from petroleum production.

The method consists of cleaning the naphthenate deposit, converting the naphthenate salts to naphthenic acids and isolating the ARN acids from the other organic acids, using a silica-based sorbent material with aminopropyl functional groups, previously selected for an efficient elution of different functional groups and polarities.

The results of ESI(−)-FT-ICR MS showed that the methodology is promising because it provided an excellent separation by difference in polarity and as a function of different molecular weight ranges, thus reducing the complexity of the organic acid extract obtained from the naphthenate deposit. Furthermore, it allowed the separation of the different acidic species that were present in the sample. The results of ESI(−)-FT-ICR MS also indicated that one of the fractions concentrated into ARN acids, including discharged species and especially ARN acids in the form of monocharged ions. The ESI(−)-Orbitrap MS data corroborated those obtained by ES(−)-FT-ICR MS, making consistent the statement that the extract obtained from the naphthenate deposit contains a mixture of acids and that the fractionation developed provided the isolation of ARN acids from naphthenate deposits. Furthermore, the integrations of the .sup.1H NMR spectra of acidic fractions as a function of molecular weight highlighted the expressive presence of alkyl compounds and absence of aromatic hydrogens in the fraction of interest.

Naphthenate deposition is formed from tetraprotic naphthenic acids having aliphatic chains and high molecular weight, provided with four carboxylic terminations, sometimes called ARN acids. Obtaining these species from their matrix of origin requires the prior use of sample preparation methods aiming at an efficient extraction of naphthenic acids. Obtaining ARN acids from naphthenate deposits is advantageous in the potential for reusing waste and reducing environmental damage. The process also adds value to waste materials from the oil production and exploration process.

The present invention relates to the field of laboratory-scale sample preparation, which describes a methodology for the specific isolation of tetraprotic naphthenic acids, called ARN acids, from residual naphthenate deposits from petroleum production.

The method consists of cleaning the naphthenate deposit, converting the naphthenate salts to naphthenic acids and isolating the ARN acids from the other organic acids, using a silica-based sorbent material with aminopropyl functional groups, previously selected for an efficient elution of different functional groups and polarities.

The results of ESI(−)-FT-ICR MS showed that the methodology is promising because it provided an excellent separation by difference in polarity and as a function of different molecular weight ranges, thus reducing the complexity of the organic acid extract obtained from the naphthenate deposit. Furthermore, it allowed the separation of the different acidic species that were present in the sample. The results of ESI(−)-FT-ICR MS also indicated that one of the fractions concentrated into ARN acids, including discharged species and especially ARN acids in the form of monocharged ions. The ESI(−)-Orbitrap MS data corroborated those obtained by ES(−)-FT-ICR MS, making consistent the statement that the extract obtained from the naphthenate deposit contains a mixture of acids and that the fractionation developed provided the isolation of ARN acids from naphthenate deposits. Furthermore, the integrations of the .sup.1H NMR spectra of acidic fractions as a function of molecular weight highlighted the expressive presence of alkyl compounds and absence of aromatic hydrogens in the fraction of interest.

A method for chemical separation of cannabinoids includes: (i) providing a starting organic solvent solution that contains a mixture of cannabinoid acids, (ii) using an aqueous basic solution to remove a portion of the cannabinoid acids from the mixture of cannabinoid acids in the starting organic solvent solution by converting the portion of the cannabinoid acids to cannabinoid carboxylate salts that solubilize in the an aqueous basic solution, (iii) separating the aqueous basic solution in (ii) from the starting organic solvent, (iv) combining the aqueous solution from (iii) with new organic solvent to produce a combined solution, (v) acidifying the combined solution to extract the cannabinoid acids from the aqueous solution to the organic solvent, (vi) separating the organic solvent of (v) from the aqueous solution, and (vii) evaporating the organic solvent of (vi) to leave product cannabinoid acids.

A method for chemical separation of cannabinoids includes: (i) providing a starting organic solvent solution that contains a mixture of cannabinoid acids, (ii) using an aqueous basic solution to remove a portion of the cannabinoid acids from the mixture of cannabinoid acids in the starting organic solvent solution by converting the portion of the cannabinoid acids to cannabinoid carboxylate salts that solubilize in the an aqueous basic solution, (iii) separating the aqueous basic solution in (ii) from the starting organic solvent, (iv) combining the aqueous solution from (iii) with new organic solvent to produce a combined solution, (v) acidifying the combined solution to extract the cannabinoid acids from the aqueous solution to the organic solvent, (vi) separating the organic solvent of (v) from the aqueous solution, and (vii) evaporating the organic solvent of (vi) to leave product cannabinoid acids.

The invention provides a process for separating saturated and unsaturated carboxylic acids is described. The process includes providing a stream comprising same carbon number saturated and unsaturated carboxylic acids; contacting said stream with an extractive solvent in an extractive distillation unit, to produce a first stream comprising extractive solvent and unsaturated carboxylic acids and a second stream comprising saturated carboxylic acids, and feeding said first stream to a solvent recovery unit, to produce a third stream comprising unsaturated carboxylic acids and a fourth stream comprising extractive solvent. In some embodiments, the extractive solvent has a boiling point at atmospheric pressure that is at least 5° C. higher than the boiling point of the unsaturated carboxylic acid.

The invention provides a process for separating saturated and unsaturated carboxylic acids is described. The process includes providing a stream comprising same carbon number saturated and unsaturated carboxylic acids; contacting said stream with an extractive solvent in an extractive distillation unit, to produce a first stream comprising extractive solvent and unsaturated carboxylic acids and a second stream comprising saturated carboxylic acids, and feeding said first stream to a solvent recovery unit, to produce a third stream comprising unsaturated carboxylic acids and a fourth stream comprising extractive solvent. In some embodiments, the extractive solvent has a boiling point at atmospheric pressure that is at least 5° C. higher than the boiling point of the unsaturated carboxylic acid.

The invention provides a process for separating saturated and unsaturated carboxylic acids is described. The process includes providing a stream comprising same carbon number saturated and unsaturated carboxylic acids; contacting said stream with an extractive solvent in an extractive distillation unit, to produce a first stream comprising extractive solvent and unsaturated carboxylic acids and a second stream comprising saturated carboxylic acids, and feeding said first stream to a solvent recovery unit, to produce a third stream comprising unsaturated carboxylic acids and a fourth stream comprising extractive solvent. In some embodiments, the extractive solvent has a boiling point at atmospheric pressure that is at least 5° C. higher than the boiling point of the unsaturated carboxylic acid.

The present disclosure provides azeotrope or azeotrope-like compositions including trifluoroiodomethane (CF.sub.3I) and trifluoroacetyl chloride (CF.sub.3COCl), methods of forming same, and methods of separating, or breaking, the azeotrope or azeotrope-like compositions of trifluoroiodomethane (CF.sub.3I) and trifluoroacetyl chloride (CF.sub.3COCl).