C07C29/60

METHOD FOR MANUFACTURING 1,3-BUTYLENE GLYCOL, AND 1,3-BUTYLENE GLYCOL PRODUCT
20230055591 · 2023-02-23 · ·

Provided is a method capable of manufacturing 1,3-butylene glycol having a high potassium permanganate test value. A method for manufacturing 1,3-butylene glycol, which is a method for obtaining purified 1,3-butylene glycol from a crude reaction liquid containing 1,3-butylene glycol, the method including: a dehydration step of removing water by distillation; a high boiling substance removal step of removing a high boiling point component by distillation; and a product distillation step of obtaining purified 1,3-butylene glycol, wherein in the product distillation step, a product column is used in which a liquid feed having a 1,3-butylene glycol concentration of 97% or higher, an acetaldehyde content of 500 ppm or lower, and a crotonaldehyde content of 200 ppm or lower is distilled under a condition of a reflux ratio of higher than 0.1, and a liquid concentrated with acetaldehyde and crotonaldehyde is distilled off from above a feed plate, and 1,3-butylene glycol is extracted from below the feed plate.

1,3-BUTYLENE GLYCOL PRODUCT AND METHOD FOR PRODUCING 1,3-BUTYLENE GLYCOL

A high-purity 1,3-butylene glycol product is provided, which is colorless and odorless (or almost colorless and odorless), unlikely to cause coloration and odor over time, and, besides, unlikely to cause an acid concentration increase over time also in a state containing water. A 1,3-butylene glycol product in which at least one of a content of methyl vinyl ketone, a content of acetone, a content of butylaldehyde, a content of acetaldol, a content of a compound represented by Formula (1) below, a content of a compound represented by Formula (2) below, a content of a compound represented by Formula (3) below, and a total content of a compound represented by Formula (4) below and a compound represented by Formula (5) below, is less than 8 ppm.

METHOD FOR MANUFACTURING 1,3-BUTYLENE GLYCOL, AND 1,3-BUTYLENE GLYCOL PRODUCT

Provided is a method capable of manufacturing high-purity 1,3-butylene glycol having a high potassium permanganate test value, a very low content of low boiling point components, and a high initial boiling point with a high recovery rate.

The method for manufacturing 1,3-butylene is a method for obtaining purified 1,3-butylene glycol from a crude reaction liquid containing 1,3-butylene glycol. In a dehydration column used in a dehydration step, a liquid feed containing 1,3 butylene glycol and water with an acetaldehyde content of 1000 ppm or lower and a crotonaldehyde content of 400 ppm or lower is distilled under a condition of a reflux ratio of higher than 0.3, and a liquid concentrated with a low boiling point component containing water is distilled off from above a feed tray. In a product column used in a product distillation step, a liquid feed containing 1,3-butylene glycol with an acetaldehyde content of 500 ppm or lower and a crotonaldehyde content of 200 ppm or lower is distilled under a condition of a reflux ratio of higher than 0.1.

METHOD FOR PRODUCING 1,3-BUTYLENE GLYCOL, AND 1,3-BUTYLENE GLYCOL PRODUCT

Provided is a method capable of yielding high-purity 1,3-butylene glycol having a very low content of a high boiling point component and a low dry point, with a high recovery ratio. A method for producing 1,3-butylene glycol to yield purified 1,3-butylene glycol from a reaction crude liquid containing 1,3-butylene glycol, in which, in a high boiling point component removal column for use in the removing a high boiling point component, a charged liquid containing 1,3 -butylene glycol is distilled under conditions that (i) a reflux ratio is greater than 0.02 in a case where a concentration of 1,3-butylene glycol in the charged liquid is 95% or less, or a reflux ratio is greater than 0.01 in a case where the concentration of 1,3-butylene glycol in the charged liquid is greater than 95%, and (ii) a bottom ratio of less than 30 wt. %, high-purity 1,3-butylene glycol is distilled off from above a charging plate, and a liquid in which a high boiling point component is concentrated is extracted from below the charging plate.

PRE-TREATMENT OF LIGNOCELLULOSIC FEEDS FOR THE PRODUCTION OF GLYCOLS

A process for the preparing glycols from a lignocellulosic solid biomass involves contacting the biomass with an organic solvent comprising a low boiling point alcohol and a pre-treatment acid at a temperature in a range from 80 to 220° C. and a pressure in a range from 1 to 50 bara. The resulting mixture, having >20 wt. % water, is separated into a pre-treated solid residue comprising cellulose and a liquid stream comprising dissolved lignin and hemicellulose. The pre-treated solid residue is subjected to a hydrogenolysis reaction, generating a glycols stream, a lights stream, comprising a first portion of organic solvent, and a heavies stream. At least of part of the liquid stream is separated to produce a second portion of organic solvent and a solid residue of lignin and hemicellulose. At least part of the first and second portion of organic solvent is recycled to the contacting step.

PRE-TREATMENT OF LIGNOCELLULOSIC FEEDS FOR THE PRODUCTION OF GLYCOLS

A process for the preparing glycols from a lignocellulosic solid biomass involves contacting the biomass with an organic solvent comprising a low boiling point alcohol and a pre-treatment acid at a temperature in a range from 80 to 220° C. and a pressure in a range from 1 to 50 bara. The resulting mixture, having >20 wt. % water, is separated into a pre-treated solid residue comprising cellulose and a liquid stream comprising dissolved lignin and hemicellulose. The pre-treated solid residue is subjected to a hydrogenolysis reaction, generating a glycols stream, a lights stream, comprising a first portion of organic solvent, and a heavies stream. At least of part of the liquid stream is separated to produce a second portion of organic solvent and a solid residue of lignin and hemicellulose. At least part of the first and second portion of organic solvent is recycled to the contacting step.

PRE-TREATMENT OF LIGNOCELLULOSIC FEEDS FOR THE PRODUCTION OF GLYCOLS

A process for the preparing glycols from a lignocellulosic solid biomass involves contacting the biomass with an organic solvent comprising a low boiling point alcohol and a pre-treatment acid at a temperature in a range from 80 to 220° C. and a pressure in a range from 1 to 50 bara. The resulting mixture, having >20 wt. % water, is separated into a pre-treated solid residue comprising cellulose and a liquid stream comprising dissolved lignin and hemicellulose. The pre-treated solid residue is subjected to a hydrogenolysis reaction, generating a glycols stream, a lights stream, comprising a first portion of organic solvent, and a heavies stream. At least of part of the liquid stream is separated to produce a second portion of organic solvent and a solid residue of lignin and hemicellulose. At least part of the first and second portion of organic solvent is recycled to the contacting step.

PRE-TREATMENT OF LIGNOCELLULOSIC FEEDS FOR THE PRODUCTION OF GLYCOLS

A process for preparing glycols from a lignocellulosic solid biomass involves contacting the biomass with an organic solvent comprising a low boiling point alcohol and a pre-treatment acid at a temperature in a range from 80 to 220° C. and a pressure in a range from 1 to 50 bara. The resulting mixture, having less than wt. % water, is separated into a pre-treated solid residue comprising cellulose and a liquid stream comprising dissolved lignin. The pre-treated solid residue is subjected to a hydrogenolysis reaction. generating a glycols stream, a lights stream, comprising a first portion of organic solvent, and a heavies stream. At least part of the liquid stream is separated to produce a second portion of organic solvent and a lignin stream. At least part of the first and second portions of organic solvent is recycled to the contacting step.

PRE-TREATMENT OF LIGNOCELLULOSIC FEEDS FOR THE PRODUCTION OF GLYCOLS

A process for preparing glycols from a lignocellulosic solid biomass involves contacting the biomass with an organic solvent comprising a low boiling point alcohol and a pre-treatment acid at a temperature in a range from 80 to 220° C. and a pressure in a range from 1 to 50 bara. The resulting mixture, having less than wt. % water, is separated into a pre-treated solid residue comprising cellulose and a liquid stream comprising dissolved lignin. The pre-treated solid residue is subjected to a hydrogenolysis reaction. generating a glycols stream, a lights stream, comprising a first portion of organic solvent, and a heavies stream. At least part of the liquid stream is separated to produce a second portion of organic solvent and a lignin stream. At least part of the first and second portions of organic solvent is recycled to the contacting step.

PRE-TREATMENT OF LIGNOCELLULOSIC FEEDS FOR THE PRODUCTION OF GLYCOLS

A process for preparing glycols from a lignocellulosic solid biomass involves contacting the biomass with an organic solvent comprising a low boiling point alcohol and a pre-treatment acid at a temperature in a range from 80 to 220° C. and a pressure in a range from 1 to 50 bara. The resulting mixture, having less than wt. % water, is separated into a pre-treated solid residue comprising cellulose and a liquid stream comprising dissolved lignin. The pre-treated solid residue is subjected to a hydrogenolysis reaction. generating a glycols stream, a lights stream, comprising a first portion of organic solvent, and a heavies stream. At least part of the liquid stream is separated to produce a second portion of organic solvent and a lignin stream. At least part of the first and second portions of organic solvent is recycled to the contacting step.