Azeotropic distillation process for producing organic acids or organic acid amides

An azeotropic distillation process for the recovery of at least one of an organic acid or an organic acid amide from a feed stream comprising at least one of the organic acid or the organic acid amide, comprising the steps of:

• mixing at least one azeotroping agent and a feed stream that comprises at least one of an organic acid or an organic acid amide and water, wherein the organic acid is selected from the group consisting of monocarboxylic acids, dicarboxylic acids, and tricarboxylic acids having from 2 to 8 carbon atoms, and the organic acid amide is selected from the group consisting of amides of monocarboxylic acids, dicarboxylic acids, and tricarboxylic acids having from 2 to 8 carbon atoms;
• and
• distilling the mixture comprising the at least one azeotroping agent and the feed stream by a method comprising the steps of
• (i) heating the mixture, wherein the heating is sufficient to produce a first vapor stream that comprises water and at least one first heteroazeotrope comprising (a) the organic acid or the organic acid amide and (b) the at least one azeotroping agent;
• and
• (ii) separating the first vapor stream from the mixture and producing a first bottoms stream;
• and
• condensing the first vapor stream to form a first liquid stream, wherein the first liquid stream comprises at least some of the organic acid or the organic acid amide, wherein the first liquid stream is capable of being separated into a first phase and a second phase, wherein the first phase comprises a higher concentration of the organic acid or the organic acid amide than the second phase, and wherein the second phase comprises the at least one azeotroping agent, wherein the first liquid stream comprises a first phase having at least about 30 wt % water, and wherein the at least one azeotroping agent is capable of forming a second heteroazeotrope consisting of water and the at least one azeotroping agent, further comprising the step of
• distilling the first liquid stream by a method comprising the steps of
• (A) heating the first liquid stream to produce a second vapor stream and a second bottoms stream, wherein the second bottoms stream comprises at least some of the organic acid or the organic acid amide, and
• (B) separating the second vapor stream from the the second bottoms stream, wherein the second vapor stream comprises the second heteroazeotrope, and wherein the second bottoms stream is capable of being separated into a third phase and a fourth phase, wherein the third phase comprises a higher concentration of the organic acid or the organic acid amide than the fourth phase, and wherein the fourth phase comprises the at least one azeotroping agent.

An azeotropic distillation process for the recovery of at least one of an organic acid or an organic acid amide from a feed stream comprising at least one of the organic acid or the organic acid amide, comprising the steps of:

• mixing at least one azeotroping agent and a feed stream that comprises at least one of an organic acid or an organic acid amide and water, wherein the organic acid is selected from the group consisting of monocarboxylic acids, dicarboxylic acids, and tricarboxylic acids having from 2 to 8 carbon atoms, and the organic acid amide is selected from the group consisting of amides of monocarboxylic acids, dicarboxylic acids, and tricarboxylic acids having from 2 to 8 carbon atoms;
• and
• distilling the mixture comprising the at least one azeotroping agent and the feed stream by a method comprising the steps of
• (i) heating the mixture, wherein the heating is sufficient to produce a first vapor stream that comprises water and at least one first heteroazeotrope comprising (a) the organic acid or the organic acid amide and (b) the at least one azeotroping agent;
• and
• (ii) separating the first vapor stream from the mixture and producing a first bottoms stream;
• and
• condensing the first vapor stream to form a first liquid stream, wherein the first liquid stream is capable of being separated into a first phase and a second phase, wherein the first phase comprises a higher concentration of the organic acid or the organic acid amide than the second phase, and wherein the second phase comprises the at least one azeotroping agent;
• wherein the organic acid is selected from the group consisting of lactic acid, pyruvic acid, beta-hydroxybutyric acid, glycolic acid, propionic acid, and acetic acid.

An azeotropic distillation process for the recovery of at least one of an organic acid or an organic acid amide from a feed stream comprising at least one of the organic acid or the organic acid amide, comprising the steps of:

• mixing at least one azeotroping agent and a feed stream that comprises at least one of an organic acid or an organic acid amide and water, wherein the organic acid is selected from the group consisting of monocarboxylic acids, dicarboxylic acids, and tricarboxylic acids having from 2 to 8 carbon atoms, and the organic acid amide is selected from the group consisting of amides of monocarboxylic acids, dicarboxylic acids, and tricarboxylic acids having from 2 to 8 carbon atoms;
• and
• distilling the mixture comprising the at least one azeotroping agent and the feed stream by a method comprising the steps of
• (i) heating the mixture, wherein the heating is sufficient to produce a first vapor stream that comprises water and at least one first heteroazeotrope comprising (a) the organic acid or the organic acid amide and (b) the at least one azeotroping agent;
• and
• (ii) separating the first vapor stream from the mixture and producing a first bottoms stream;
• and
• condensing the first vapor stream to form a first liquid stream, wherein the first liquid stream is capable of being separated into a first phase and a second phase, wherein the first phase comprises a higher concentration of the organic acid or the organic acid amide than the second phase, and wherein the second phase comprises the at least one azeotroping agent;
• wherein the organic acid amide is selected from the group consisting of lactamide, pyruvamide, beta-hydroxybutyamide, propionamide, and acetamide.

An azeotropic distillation process for the recovery of at least one of an organic acid or an organic acid amide from a feed stream comprising at least one of the organic acid or the organic acid amide, comprising the steps of:

• mixing at least one azeotroping agent and a feed stream that comprises at least one of an organic acid or an organic acid amide and water, wherein the organic acid is selected from the group consisting of monocarboxylic acids, dicarboxylic acids, and tricarboxylic acids having from 2 to 8 carbon atoms, and the organic acid amide is selected from the group consisting of amides of monocarboxylic acids, dicarboxylic acids, and tricarboxylic acids having from 2 to 8 carbon atoms;
• and
• distilling the mixture comprising the at least one azeotroping agent and the feed stream by a method comprising the steps of
• (i) heating the mixture, wherein the heating is sufficient to produce a first vapor stream that comprises water and at least one first heteroazeotrope comprising (a) the organic acid or the organic acid amide and (b) the at least one azeotroping agent;
• and
• (ii) separating the first vapor stream from the mixture and producing a first bottoms stream;
• and
• condensing the first vapor stream to form a first liquid stream, wherein the first liquid stream is capable of being separated into a first phase and a second phase, wherein the first phase comprises a higher concentration of the organic acid or the organic acid amide than the second phase, and wherein the second phase comprises the at least one azeotroping agent;
• wherein the organic acid is a hydroxy acid.

An azeotropic distillation process for the recovery of at least one of an organic acid or an organic acid amide from a feed stream comprising at least one of the organic acid or the organic acid amide, comprising the steps of:

• mixing at least one azeotroping agent and a feed stream that comprises at least one of an organic acid or an organic acid amide and water, wherein the organic acid is selected from the group consisting of monocarboxylic acids, dicarboxylic acids, and tricarboxylic acids having from 2 to 8 carbon atoms, and the organic acid amide is selected from the group consisting of amides of monocarboxylic acids, dicarboxylic acids, and tricarboxylic acids having from 2 to 8 carbon atoms;
• and
• distilling the mixture comprising the at least one azeotroping agent and the feed stream by a method comprising the steps of
• (i) heating the mixture, wherein the heating is sufficient to produce a first vapor stream that comprises water and at least one first heteroazeotrope comprising (a) the organic acid or the organic acid amide and (b) the at least one azeotroping agent;
• and
• (ii) separating the first vapor stream from the mixture and producing a first bottoms stream;
• and
• condensing the first vapor stream to form a first liquid stream, wherein the first liquid stream is capable of being separated into a first phase and a second phase, wherein the first phase comprises a higher concentration of the organic acid or the organic acid amide than the second phase, and wherein the second phase comprises the at least one azeotroping agent;
• wherein the organic acid amide is a hydroxyamide.

An azeotropic distillation process for the recovery of at least one of an organic acid or an organic acid snide from a feed stream comprising at least one of the organic acid or the organic acid amide, comprising the steps of:

• mixing at least one azeotroping agent and a feed stream that comprises at least one of an organic acid or an organic acid amide and water, wherein the organic acid is selected from the group consisting of monocarboxylic acids, dicarboxylic acids, and tricarboxylic acids having from 2 to 8 carbon atoms, and the organic acid amide is selected from the group consisting of amides of monocarboxylic acids, dicarboxylic acids, and tricarboxylic acids having from 2 to 8 carbon atoms;
• and
• distilling the mixture comprising the at least one azeotroping agent and the feed steam by a method comprising the steps of
• (i) heating the mixture, wherein the heating is sufficient to produce a first vapor stream that comprises water and at least one first heteroazeotrope comprising (a) the organic acid or the organic acid amide and (b) the at least one azeotroping agent;
• and
• (ii) separating the first vapor stream from the mixture and producing a first bottoms stream;
• and
• condensing the first vapor stream so form a first liquid stream, wherein the first liquid stream is capable of being separated into a first phase and a second phase, wherein the first phase comprises a higher concentration of the organic acid or the organic acid amide than the second phase, and wherein the second phase comprises the at least one azeotroping agent;
• wherein the feed stream is a fermentation broth.

An azeotropic distillation process for the recovery of at least one of an organic acid or an organic acid amide from a feed stream comprising at least one of the organic acid or the organic acid amide, comprising the steps of:

• mixing at least one azeotroping agent and a feed stream that comprises at least one of an organic acid or an organic acid amide and water, wherein the organic acid is selected from the group consisting of monocarboxylic acids, dicarboxylic acids, and tricarboxylic acids having from 2 to 8 carbon atoms, and the organic acid amide is selected from the group consisting of amides of monocarboxylic acids, dicarboxylic acids, and tricarboxylic acids having from 2 to 8 carbon atoms;
• and
• distilling the mixture comprising the at least one azeotroping agent and the feed stream by a method comprising the steps of
• (i) heating the mixture, wherein the heating is sufficient to produce a first vapor stream that comprises water and at least one first heteroazeotrope comprising (a) the organic acid or the organic acid amide and (b) the at least one azeotroping agent;
• and
• (ii) separating the first vapor stream from the mixture and producing a first bottoms stream;
• and
• condensing the first vapor stream to form a first liquid stream, wherein the first liquid stream is capable of being separated into a first phase and a second phase, wherein the first phase comprises a higher concentration of the organic acid or the organic acid amide than the second phase, and wherein the second phase comprises the at least one azeotroping agent;
• wherein the at least one azeotroping agent is a hydrocarbon having a boiling point of between about 100° C. less than and 150° C. more than the organic acid or the organic acid amide boiling point.

An azeotropic distillation process for the recovery of at least one of an organic acid or an organic acid amide from a feed stream comprising at least one of the organic acid or the organic acid amide, comprising the steps of:

• mixing at least one azeotroping agent and a feed stream that comprises at least one of an organic acid or an organic acid amide and water, wherein the organic acid is selected from the group consisting of monocarboxylic acids, dicarboxylic acids, and tricarboxylic acids having from 2 to 8 carbon atoms, and the organic acid amide is selected from the group consisting of amides of monocarboxylic acids, dicarboxylic acids, and tricarboxylic acids having from 2 to 8 carbon atoms;
• and
• distilling the mixture comprising the at least one azeotroping agent and the feed stream by a method comprising the steps of
• (i) heating the mixture, wherein the heating is sufficient to produce a first vapor stream that comprises water and at least one first heteroazeotrope comprising (a) the organic acid or the organic acid amide and (b) the at least one azeotroping agent;
• and
• (ii) separating the first vapor stream from the mixture and producing a first bottoms stream;
• and
• condensing the first vapor stream to form a first liquid stream, wherein the first liquid stream is capable of being separated into a first phase and a second phase, wherein the first phase comprises a higher concentration of the organic acid or the organic acid amide than the second phase, and wherein the second phase comprises the at least one azeotroping agent;
• wherein the feed stream comprises between about 15 wt % to 85 wt % of the organic acid, and further comprises greater than about 10 wt % water, and between about 5 wt % to 70 wt % at least one salt of the organic acid.

An azeotropic distillation process for the recovery of at least one of an organic acid or an organic acid amide from a feed stream comprising at least one of the organic acid or the organic acid amide, comprising the steps of:

• mixing at least one azeotroping agent and a feed stream that comprises at least one of an organic acid or an organic acid amide and water, wherein the organic acid is selected from the group consisting of monocarboxylic acids, dicarboxylic acids, and tricarboxylic acids having from 2 to 8 carbon atoms, and the organic acid amide is selected from the group consisting of amides of monocarboxylic acids, dicarboxylic acids, and tricarboxylic acids having from 2 to 8 carbon atoms;
• and
• distilling the mixture comprising the at least one azeotroping agent and the feed stream by a method comprising the steps of
• (i) heating the mixture, wherein the heating is sufficient to produce a first vapor stream that comprises water and at least one first heteroazeotrope comprising (a) the organic acid or the organic acid amide and (b) the at least one azeotroping agent;
• and
• (ii) separating the first vapor stream from the mixture and producing a first bottoms stream;
• and
• condensing the first vapor stream to form a first liquid stream, wherein the first liquid stream is capable of being separated into a first phase and a second phase, wherein the first phase comprises a higher concentration of the organic acid or the organic acid amide than the second phase, and wherein the second phase comprises the at least one azeotroping agent;
• wherein the feed stream comprises less than about 5 wt % salts, greater than about 15 wt % the organic acid, and at least one impurity.

An azeotropic distillation process for the recovery of at least one of an organic acid or an organic acid amide from a feed stream comprising at least one of the organic acid or the organic acid amide, comprising the steps of:

• mixing at least one azeotroping agent and a feed stream that comprises at least one of an organic acid or an organic acid amide and water, wherein the organic acid is selected from the group consisting of monocarboxylic acids, dicarboxylic acids, and tricarboxylic acids having from 2 to 8 carbon atoms, and the organic acid amide is selected from the group consisting of amides of monocarboxylic acids, dicarboxylic acids, and tricarboxylic acids having from 2 to 8 carbon atoms;
• and
• distilling the mixture comprising the at least one azeotroping agent and the feed stream by a method comprising the steps of
• (i) heating the mixture, wherein the heating is sufficient to produce a first vapor stream that comprises water and at least one first heteroazeotrope comprising (a) the organic acid or the organic acid amide and (b) the least one azeotroping agent;
• and
• (ii) separating the first vapor stream from the mixture and producing a first bottoms stream;
• and wherein the first vapor stream comprises lactamide and lactic acid.

An azeotropic distillation process for the recovery of at least one of an organic acid or an organic acid amide from a feed stream comprising at least one of the organic acid or the organic acid amide, comprising the steps of:

• mixing at least one azeotroping agent and a feed stream that comprises at least one of an organic acid or an organic acid amide and water, wherein the organic acid is selected from the group consisting of monocarboxylic acids, dicarboxylic acids, and tricarboxylic acids having from 2 to 8 carbon atoms, and the organic acid amide is selected from the group consisting of amides of monocarboxylic acids, dicarboxylic acids, and tricarboxylic acids having from 2 to 8 carbon atoms;
• and
• distilling the mixture comprising the at least one azeotroping agent and the feed stream by a method comprising the steps of
• (i) heating the mixture, wherein the heating is sufficient to produce a first vapor stream that comprises water and at least one first heteroazeotrope comprising (a) the organic acid or the organic acid amide and (b) the at least one azeotroping agent;
• and
• (ii) separating the first vapor stream from the mixture and producing a first bottoms stream;
• and wherein the at least one of an organic acid or an organic acid amide is the product of the treatment of a polyester.

An azeotropic distillation process for the recovery of at least one of an organic acid or an organic acid amide front a feed stream comprising at least one of the organic acid or the organic acid amide, comprising the steps of:

• mixing at least one azeotroping agent and a feed stream that comprises at least one of an organic acid or an organic acid amide and water, wherein the organic acid is selected from the group consisting of monocarboxylic acids, dicarboxylic acids, and tricarboxylic acids having from 2 to 8 carbon atoms, and the organic acid amide is selected from the group consisting of amides of monocarboxylic acids, dicarboxylic acids, and tricarboxylic acids having from 2 to 8 carbon atoms;
• and
• distilling the mixture comprising the at least one azeotroping agent and the feed steam by a method comprising the steps of
• (i) heating the mixture, wherein the heating is sufficient to produce a first vapor stream that comprises water and at least one first heteroazeotrope comprising (a) the organic acid or the organic acid amide and (b) the at least one azeotroping agent;
• and
• (ii) separating the first vapor steam from the mixture and producing a first bottoms stream;
• and wherein the time the mixture is heated in step (i) is limited in order to reduce racemization.

An azeotropic distillation process for the recovery of at least one of an organic acid or an organic acid amide from a feed stream comprising at least one of the organic acid or the organic acid amide, comprising the steps of:

• mixing at least one azeotroping agent and a feed stream that comprises at least one of an organic acid or an organic acid amide and water, wherein the organic acid is selected from the group consisting of monocarboxylic acids, dicarboxylic acids, and tricarboxylic acids having from 2 to 8 carbon atoms, and the organic acid amide is selected from the group consisting of amides of monocarboxylic acids, dicarboxylic acids, and tricarboxylic acids having from 2 to 8 carbon atoms;
• and
• distilling the mixture comprising the at least one azeotroping agent and the feed stream by a method comprising the steps of
• (i) heating the mixture, wherein the heating is sufficient to produce a first vapor stream that comprises water and at least one first heteroazeotrope comprising (a) the organic acid or the organic acid amide and (b) the at least one azeotroping agent;
• and
• (ii) separating the first vapor stream from the mixture and producing a first bottoms stream, wherein the first bottoms stream comprises as least some of the organic acid or the organic acid amide, wherein the first bottoms stream is capable of being separated into a first phase and a second phase, wherein the first phase comprises a higher concentration of the organic acid or the organic acid amide than the second phase, and wherein the second phase comprises the at least one azeotroping agent;
• separating the first bottoms stream into a first phase and a second phase;
• condensing the first vapor stream to produce a first liquid stream;
• distilling the first liquid stream by a method comprising the steps of
• (A) adjusting the temperature of the first liquid stream to a temperature sufficient to produce a second vapor stream that comprises an azeotrope that comprises water and the at least one azeotroping agent and a second bottoms stream;
• (B) separating the second vapor stream from the second bottoms stream, wherein the second bottoms stream comprises at least some of the organic acid or the organic acid amide;
• and
• wherein the mixing is done in a first fractional distillation column, the separating step (B) is done in a second fractional distillation column, and wherein the first fractional distillation column and the second fractional distillation column are used in series.

An azeotropic distillation process for the recovery of at least one of an organic acid or an organic acid amide from a feed stream comprising at least one of the organic acid or the organic acid amide, comprising the steps of:

• mixing at least one azeotroping agent and a feed stream that comprises at least one of an organic acid or an organic acid amide and water, wherein the organic acid is selected from the group consisting of monocarboxylic acids, dicarboxylic acids, and tricarboxylic acids having from 2 to 8 carbon atoms, and the organic acid amide is selected from the group consisting of amides of monocarboxylic acids, dicarboxylic acids, and tricarboxylic acids having from 2 to 8 carbon atoms;
• and
• distilling the mixture comprising the at least one azeotroping agent and the feed stream by a method comprising the steps of
• (i) heating the mixture, wherein the heating is sufficient to produce a fast vapor stream that comprises water and at least one first heteroazeotrope comprising (a) the organic acid or the organic acid amide and (b) the at least one azeotroping agent;
• and
• (ii) separating the first vapor stream from the mixture and producing a first bottoms stream;
• and
• wherein the at least one azeotroping agent is a long chain alcohol having 7 to 13 carbon atoms, and the organic acid is lactic acid.

An azeotropic distillation process for the recovery of at least one of an organic acid or an organic acid amide from a feed steam comprising at least one of the organic acid or the organic acid amide, comprising the steps of,

• mixing at least one azeotroping agent and a feed steam that comprises at least one of an organic acid or an organic acid amide and water, wherein the organic acid is selected from the group consisting of monocarboxylic acids, dicarboxylic acids, and tricarboxylic acids having from 2 to 8 carbon atoms, and the organic acid amide is selected from the group consisting of amides of monocarboxylic acids, dicarboxylic acids, and tricarboxylic acids having from 2 to 8 carbon atoms;
• and
• distilling the mixture comprising the at least one azeotroping agent and the feed stream by a method comprising the steps of
• (i) heating at the mixture, wherein the heating is sufficient to produce a first vapor stream that comprises water and at least one first heteroazeotrope comprising (a) the organic acid or the organic acid amide and (b) the at least one azeotroping agent;
• and
• (ii) separating the first vapor stream from the mixture and producing a first bottoms stream;
• and
• wherein the at least one azeotroping agent is an aromatic hydrocarbon having 9 to 15 carbon atoms and the organic acid is lactic acid.

An azeotropic distillation process for the recovery of at least one of an organic acid or an organic acid amide from a feed stream comprising at least one of the organic acid or the organic acid amide, comprising the steps of:

• mixing at least one azeotroping agent and a feed stream that comprises at least one of an organic acid or an organic acid amide and water, wherein the organic acid is selected from the group consisting of monocarboxylic acids, dicarboxylic acids, and tricarboxylic acids having from 2 to 8 carbon atoms, and the organic acid amide is selected from the group consisting of amides of monocarboxylic acids, dicarboxylic acids, and tricarboxylic acids having from 2 to 8 carbon atoms;
• and
• distilling the mixture comprising the at least one azeotroping agent and the feed stream by a method comprising the steps of
• (i) heating the mixture, wherein the heating is sufficient to produce a first vapor stream that comprises water and at least one first heteroazeotrope comprising (a) the organic acid or the organic acid amide and (b) the at least one azeotroping agent;
• and
• (ii) separating the first vapor stream from the mixture and producing a first bottoms stream;
• and
• condensing the first vapor stream to form a first liquid stream, wherein the first liquid stream is capable of being separated into a first phase and a second phase, wherein the first phase comprises a higher concentration of the organic acid or the organic acid amide than the second phase, and wherein the second phase comprises the at least one azeotroping agent;
• wherein the at least one azeotroping agent is an ether having from 7 to 16 carbon atoms or an alcohol having from 7 to 13 carbon atoms.