Process for the separation and purification of a mixed diol stream

Patent metadata

Field	Value
Publication number	US-10329230-B2
Application number	US-201514950503-A
Country	US
Kind code	B2
Filing date	Nov 24, 2015
Priority date	Aug 18, 2010
Publication date	Jun 25, 2019
Grant date	Jun 25, 2019

Abstract

Disclosed is a process for the purification of a mixed diol stream. The mixed diol stream comprising two-, three-, and four-carbon diols is separated into component diols by extraction with a hydrophobic solvent mixture. The diols recovered in the extractant may be removed from the extractant stream by back extraction with water or by distillation with an azeotrope-forming agent present, preferably an azeotroping agent already present in the extractant mixture.

First claim

What is claimed is:

1. A process for recovering diols from a mixed diol stream, comprising
(A) extracting said mixed diol stream, comprising
(i) 0.1 weight percent to 50 weight percent of one or more diols selected from the group consisting of ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, and 2,3-butanediol;
(ii) 5 weight percent to 90 weight percent glycerol; and
(iii) 5 weight percent to 90 weight percent water; each based on the total weight of said mixed diol steam stream, with an extractant, comprising
(i) a hydrophobic solvent selected from alkanols having from 6 to 20 carbon atoms, ketones having from 5 to 20 carbon atoms, esters having from 5 to 20 carbon atoms, ethers having from 5 to 20 carbon atoms, carboxylic acids having from 5 to 20 carbon atoms, trialkylphosphine oxides having from 18 to 48 carbon atoms, and mixtures thereof; and
(ii) optionally, a second modifying hydrophobic solvent selected from hydrocarbons having from 5 to 20 carbon atoms; to form a raffinate phase comprising a major amount of said glycerol and a minor amount of said diols contained in said mixed diol stream and an extract phase comprising a major amount of said diols and a minor amount of said glycerol contained in said mixed diol stream; and

(B) separating said raffinate phase and said extract phase.

2. The process according to claim 1 wherein said hydrophobic solvent is selected from 2-ethylhexanol, cyclohexanol, n-hexanol, methyl isobutyl ketone, methyl isopropyl ketone, methyl propyl ketone, diisobutyl ketone, trioctylphosphine oxide, trihexylphosphine oxide, and mixtures thereof.

3. The process according to claim 2 wherein greater than 99.5 weight percent of said glycerol is recovered in said raffinate phase and greater than 90 weight percent of said diols is recovered in said extract phase; and wherein said extraction occurs in a continuous counter-current extractor, wherein said extractant is fed lower to said extractor than said mixed diol stream, wherein the feed ratio of said extractant to said mixed diol stream ranges from 0.1:1 to 10:1; further comprising feeding a hydrophilic stream to said extractor at a higher level than said mixed diol stream, wherein the feed ratio of said hydrophilic stream to said mixed diol stream ranges from 0.05:1 to 2.0:1, and wherein said hydrophilic stream comprises water.

4. A process for recovering diols from a mixed diol stream, comprising
(A) extracting said mixed diol stream, comprising
(i) 0.1 weight percent to 30 weight percent of one or more diols selected from the group consisting of ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, and 2,3-butanediol;
(ii) 5 weight percent to 50 weight percent glucose; and
(iii) 50 weight percent to 90 weight percent water; each based on the total weight of said mixed diol steam stream, with an extractant, comprising
(i) a hydrophobic solvent selected from alkanols having from 6 to 20 carbon atoms, ketones having from 5 to 20 carbon atoms, esters having from 5 to 20 carbon atoms, ethers having from 5 to 20 carbon atoms, carboxylic acids having from 5 to 20 carbon atoms, trialkylphosphine oxides having from 18 to 48 carbon atoms, and mixtures thereof; and
(ii) optionally, a second modifying hydrophobic solvent selected from hydrocarbons having from 5 to 20 carbon atoms; to form a raffinate phase comprising a major amount of said glycerol and a minor amount of said diols contained in said mixed diol stream and an extract phase comprising a major amount of said diols and a minor amount of said glycerol contained in said mixed diol stream; and

(B) separating said raffinate phase and said extract phase.

5. The process according to claim 4 wherein said hydrophobic solvent is selected from 2-ethylhexanol, cyclohexanol, n-hexanol, methyl isobutyl ketone, methyl isopropyl ketone, methyl propyl ketone, diisobutyl ketone, trioctylphosphine oxide, trihexylphosphine oxide, and mixtures thereof.

6. The process according to claim 5 wherein greater than 99.5 weight percent of said glucose is recovered in said raffinate phase and greater than 90 weight percent of diols is recovered in said extract phase; and wherein said extraction occurs in a continuous counter-current extractor, wherein said extractant is fed lower to said extractor than said mixed diol stream, wherein the feed ratio of said extractant to said mixed diol stream ranges from 0.1:1 to 10:1; further comprising feeding a hydrophilic stream to said extractor at a higher level than said mixed diol stream, wherein the feed ratio of said hydrophilic stream to said mixed diol stream ranges from 0.05:1 to 2.0:1, and wherein said hydrophilic stream comprises water.

7. A process for recovering purified three-carbon diols from a mixed diol stream, comprising
(A) extracting said mixed diol stream, comprising
(i) 1 weight percent to 99.5 weight of one or more three-carbon diols selected from 1,2-propanediol and 1,3-propanediol;
(ii) 20 ppm by weight to 99 weight percent of one or more four-carbon diols selected from 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, and 2,3-butanediol; each based on the total weight of said diols, and
(iii) 0 weight percent to 50 weight percent water, based on the total weight of said diols and said water, with an extractant, comprising
(i) a hydrophobic solvent selected from alkanols having from 6 to 20 carbon atoms, ketones having from 5 to 20 carbon atoms, esters having from 5 to 20 carbon atoms, ethers having from 5 to 20 carbon atoms, carboxylic acids having from 5 to 20 carbon atoms, trialkylphosphine oxides having from 18 to 48 carbon atoms, and mixtures thereof; and
(ii) optionally, a second modifying hydrophobic solvent selected from hydrocarbons having from 5 to 20 carbon atoms; to form a raffinate phase comprising a major amount of said three-carbon diols and a minor amount of said four-carbon diols contained in said mixed diol stream and an extract phase comprising a major amount of said four-carbon diols and a minor amount of said three-carbon diols contained in said mixed diol stream; and

(B) separating said raffinate phase and said extract phase.

8. The process according to claim 7 wherein said hydrophobic solvent is selected from 2-ethylhexanol, cyclohexanol, n-hexanol, methyl isobutyl ketone, methyl isopropyl ketone, methyl propyl ketone, diisobutyl ketone, trioctylphosphine oxide, trihexylphosphine oxide, and mixtures thereof.

9. The process according to claim 8 wherein greater than 99.5 weight percent of said three-carbon diols in said mixed diol stream is recovered in said raffinate phase and greater than 90 weight percent of said four-carbon diols is recovered in said extract phase; and wherein said extraction occurs in a continuous counter-current extractor, wherein said extractant is fed lower to said extractor than said mixed diol stream, wherein the feed ratio of said extractant to said mixed diol stream ranges from 0.1:1 to 10:1; further comprising feeding a hydrophilic stream to said extractor at a higher level than said mixed diol stream, wherein the feed ratio of said hydrophilic stream to said mixed diol stream ranges from 0.05:1 to 1.5:1, and wherein said hydrophilic stream comprises water.

Assignees

• Eastman Chem Co

Inventors

• Barnicki Scott Donald

Classifications

• Y02P20/52

  using catalysts, e.g. selective catalysts · CPC title

• B01J31/2409

  with more than one complexing phosphine-P atom · CPC title

• B01J2531/0258

  Flexible ligands, e.g. mainly sp3-carbon framework as exemplified by the "tedicyp" ligand, i.e. cis-cis-cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane · CPC title

• C07C29/149

  with hydrogen or hydrogen-containing gases · CPC title

• B01J2531/821

  Ruthenium · CPC title