Purification of 3-Hydroxypropionic Acid from Crude Cell Broth and Production of Acrylamide
A process for producing high purity 3-hydroxypropionic acid from a fermentation cell broth is described. The 3-hydroxypropionic acid can be converted to a variety of products, such as acrylamide, 3-hydroxypropionic esters, acrylic esters, and 3-HP amide. This process features a high degree of product flexibility, limited or no solvent recycle, discrete waste streams, an efficient water removal process, and efficient recovery of products and solvents with proven and scalable equipment.
1 . A process for producing high purity 3-hydroxypropionic acid (3-HP), comprising: (a) providing a fermentation broth comprising 3-HP, or salt thereof; (b) removing a substantial amount of water from said fermentation broth to give a concentrated fermentation broth; (c) extracting said 3-HP from said concentrated fermentation broth with an organic solvent, wherein said organic solvent has a boiling point of less than 170° C.; and (d) distilling the extract from step (c) to give said high purity 3-HP and/or its ester.
2 . The process of claim 1 , wherein said high purity 3-HP has purity higher than 90%.
3 . The process of claim 1 , wherein said high purity 3-HP has purity higher than 95%.
4 . The process of claim 1 , wherein a substantial amount of whole cells are removed from said fermentation broth prior to step (a).
5 . The process of claim 1 , wherein a substantial amount of whole cells are removed from said fermentation broth after step (a).
6 . The process of claim 4 or 5 , wherein said substantial amount of whole cells are removed with a centrifuge.
7 . The process of claim 1 , wherein said removing a substantial amount of water is performed by evaporation.
8 . The process of claim 1 , wherein said evaporation is carried out at a temperature range of 50-150° C.
9 . The process of claim 1 , wherein said evaporation is carried out at a reduced pressure of 20-1,000 mbar.
10 . The process of claim 1 , wherein said removing a substantial amount of water is performed with mechanical recompression methods.
11 . The process of claim 1 , wherein said removing a substantial amount of water is performed with a thin film evaporator.
12 . The process of claim 1 , wherein at least 80% of water in said fermentation broth is removed.
13 . The process of claim 1 , wherein at least 90% of water in said fermentation broth is removed.
14 . The process of claim 1 , wherein at least 95% of water in said fermentation broth is removed.
15 . The process of claim 1 , wherein at least 99% of water in said fermentation broth is removed.
16 . The process of claim 1 , further comprising separating any resulting solids during or after removing water.
17 . The process of claim 1 , further comprising adjusting pH of said concentrated fermentation broth with an acid after step (b).
18 . The process of claim 17 , wherein said acid is sulfuric acid.
19 . The process of claim 17 , wherein said acid is phosphoric acid.
20 . The process of claim 17 , further comprising separating any resulting solids during or after the addition of said acid.
21 . The process of claim 1 , wherein said organic solvent is an alcohol solvent.
22 . The process of claim 21 , wherein said alcohol solvent is selected from the group consisting of C 1 -C 12 aliphatic alcohols.
23 . The process of claim 21 , wherein said alcohol solvent is methanol.
24 . The process of claim 21 , wherein said alcohol solvent is selected from ethanol and propanol.
25 . The process of claim 21 , wherein said alcohol solvent is butanol.
26 . The process of claim 21 , wherein said alcohol solvent is hexanol.
27 . The process of claim 1 , wherein said organic solvent is selected from the group consisting of aldehydes, ketones and ethers.
28 . The process of claim 1 , wherein about 90% of 3-HP is recovered from said concentrated fermentation broth after step (b).
29 . The process of claim 21 , further comprising refluxing and/or distilling the 3-HP containing extract to generate a 3-HP ester.
30 . The process of claim 29 , wherein refluxing comprises adding a catalytic amount of acid.
31 . The process of claim 30 , wherein said acid is sulfuric acid.
32 . The process of claim 29 , further comprising carrying out an amidation reaction to generate a 3-HP amide.
33 . The process of claim 32 , further comprising a dehydration reaction to generate acrylamide.
34 . The process of claim 29 , wherein less than two equivalents of said alcohol solvent based on the amount of 3-HP is used to produce said 3-HP ester.
35 . The process of claim 34 , wherein about one equivalent of said alcohol solvent based on the amount of 3-HP is used to produce said 3-HP ester.
36 . A high purity 3-HP produced by the steps of: (a) providing a fermentation broth comprising 3-HP, or salt thereof; (b) removing a substantial amount of water from said fermentation broth to give a concentrated fermentation broth; (c) extracting said 3-HP from said concentrated fermentation broth with an organic solvent; and (d) distilling said 3-HP to give said high purity 3-HP.
37 . A 3-HP ester produced by the steps of: (a) providing a fermentation broth comprising 3-HP, or salt thereof; (b) removing a substantial amount of water from said fermentation broth to give a concentrated fermentation broth; (c) extracting said 3-HP from said concentrated fermentation broth with an alcohol solvent; and (d) refluxing and/or distilling the 3-HP containing extract to generate said 3-HP ester.
38 . 3-HP amide produced by the steps of: (a) providing a fermentation broth comprising 3-HP, or salt thereof; (b) removing a substantial amount of water from said fermentation broth to give a concentrated fermentation broth; (c) extracting said 3-HP from said concentrated fermentation broth with an organic solvent; and (d) converting said 3-HP to 3-HP amide.
39 . Acrylamide produced by the steps of: (a) providing a fermentation broth comprising 3-HP, or salt thereof; (b) removing a substantial amount of water from said fermentation broth to give a concentrated fermentation broth; (c) extracting said 3-HP from said concentrated fermentation broth with an organic solvent; and (d) converting said 3-HP to acrylamide.
40 . A process of producing a 3-HP-based product, comprising:
(a) producing 3-HP according to the process of claim 1 ; and
(b) converting said 3-HP into a 3-HP-based product.
41 . The product of claim 40 , wherein the product is selected from the group consisting of a diaper, a feminine hygiene product, an adult incontinence product, a paint, a coating, an ink, and a thickening agent.
42 . A system, comprising: (a) a fermenter; (b) an evaporator; (c) a centrifuge; (d) an extractor; (e) a reactive distillation apparatus; (f) an esterification tank; and (g) an amidation reactor.
43 . The system of claim 42 , wherein said evaporator is upstream of said extractor.
44 . The system of claim 42 , wherein water is removed by said evaporator.
45 . The system of claim 42 , wherein said fermenter comprises a fermentation broth having a 3-HP concentration of at least 10 g/L.
46 . The system of claim 42 , wherein said centrifuge comprises a liquid phase having a 3-HP concentration of at least 10 g/L.
47 . A process for purifying 3-HP from a fermentation broth, comprising: (a) removing a substantial amount of water from said fermentation broth to give a concentrated fermentation broth; and (b) extracting said 3-HP from said concentrated fermentation broth with an organic solvent.