C07C51/02

METHOD OF ISOLATION OF ARN ACIDS FROM NAPHTHENATE DEPOSITS

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.

METHOD OF ISOLATION OF ARN ACIDS FROM NAPHTHENATE DEPOSITS

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.

Process for purification of malonic acid from fermentation broth
11326191 · 2022-05-10 · ·

A process for the preparation of bio-based malonic acid and crystalline calcium malonate is provided. The calcium malonate is highly pure and provides a source of malonic acid made from a renewable carbon source rather than existing processes which rely on the use of petroleum-based products. The calcium malonate provides an improved source of malonic acid, which is important to many industrial processes.

Process for purification of malonic acid from fermentation broth
11326191 · 2022-05-10 · ·

A process for the preparation of bio-based malonic acid and crystalline calcium malonate is provided. The calcium malonate is highly pure and provides a source of malonic acid made from a renewable carbon source rather than existing processes which rely on the use of petroleum-based products. The calcium malonate provides an improved source of malonic acid, which is important to many industrial processes.

METHOD FOR MANUFACTURING CYCLOPROPANE COMPOUND

The present invention provides an industrially advantageous production method of (1R,2S)-2-{[((2,4-dimethylpyrimidin-5-yl)oxy}methyl]-2-(3-fluorophenyl)-N-(5-fluoropyridin-2-yl)cyclopropane-1-carboxamide.

(1R,2S)-2-{[((2,4-Dimethylpyrimidin-5-yl)oxyl}methyl]-2-(3-fluorophenyl)-N-(5-fluoropyridin-2-yl)cyclopropane-1-carboxamide (compound [A]) is produced by an industrially advantageous method by a route via a novel compound.

##STR00001##

wherein each symbol is as described in the description.

METHOD FOR MANUFACTURING CYCLOPROPANE COMPOUND

The present invention provides an industrially advantageous production method of (1R,2S)-2-{[((2,4-dimethylpyrimidin-5-yl)oxy}methyl]-2-(3-fluorophenyl)-N-(5-fluoropyridin-2-yl)cyclopropane-1-carboxamide.

(1R,2S)-2-{[((2,4-Dimethylpyrimidin-5-yl)oxyl}methyl]-2-(3-fluorophenyl)-N-(5-fluoropyridin-2-yl)cyclopropane-1-carboxamide (compound [A]) is produced by an industrially advantageous method by a route via a novel compound.

##STR00001##

wherein each symbol is as described in the description.

FORMATE PRODUCTION METHOD, FORMIC ACID PRODUCTION METHOD, AND ANTIFREEZING AGENT PRODUCTION METHOD

The invention relates to a method for producing a formate, the method including a first step of reacting hydrogen with carbon dioxide, a hydrogen carbonate or a carbonate using a catalyst in the presence of a solvent to form a formate in the reaction liquid, wherein the reaction is a two-phase system in which an organic phase and an aqueous phase are present in a separated state in the solvent, and a base concentration in the reaction is 2.5 mol/L or more.

FORMATE PRODUCTION METHOD, FORMIC ACID PRODUCTION METHOD, AND ANTIFREEZING AGENT PRODUCTION METHOD

The invention relates to a method for producing a formate, the method including a first step of reacting hydrogen with carbon dioxide, a hydrogen carbonate or a carbonate using a catalyst in the presence of a solvent to form a formate in the reaction liquid, wherein the reaction is a two-phase system in which an organic phase and an aqueous phase are present in a separated state in the solvent, and a base concentration in the reaction is 2.5 mol/L or more.

FIBRES
20230295396 · 2023-09-21 ·

A process (1, 2) for processing feedstock containing cotton fibres and PET fibres, the process (1, 2) comprises: i. heating a suspension of feedstock containing cotton fibres and PET fibres in water at a temperature above 180° C. to produce a mixture comprising char; ii. removing the water from the mixture comprising char; iii. adding a base to the mixture comprising char to produce a terephthalate salt in a liquid phase; iv. removing the char from the liquid phase to produce dried char; v. acidifying the liquid phase to produce terephthalic acid.

FIBRES
20230295396 · 2023-09-21 ·

A process (1, 2) for processing feedstock containing cotton fibres and PET fibres, the process (1, 2) comprises: i. heating a suspension of feedstock containing cotton fibres and PET fibres in water at a temperature above 180° C. to produce a mixture comprising char; ii. removing the water from the mixture comprising char; iii. adding a base to the mixture comprising char to produce a terephthalate salt in a liquid phase; iv. removing the char from the liquid phase to produce dried char; v. acidifying the liquid phase to produce terephthalic acid.