IP Library Granted Patent US 8,399,687
Granted Patent B2
US 8,399,687 · App. 13/334,629 · Granted Mar 19, 2013

Processes for the production of hydrogenated products

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Quick Facts
Patent No.
US 8,399,687
App. No.
13/334,629
Granted
Mar 19, 2013
Kind
B2
Abstract

A process for making a hydrogenated product includes providing a clarified DAS-containing fermentation broth, distilling the broth to form an overhead that includes water and ammonia, and a liquid bottoms that includes MAS, at least some DAS, and at least about 20 wt % water, cooling and/or evaporating the bottoms, and optionally adding an antisolvent to the bottoms, to attain a temperature and composition sufficient to cause the bottoms to separate into a DAS-containing liquid portion and a MAS-containing solid portion that is substantially free of DAS, separating the solid portion from the liquid portion, recovering the solid portion, hydrogenating the second solid portion in the presence of at least one hydrogenation catalyst to produce the hydrogenated product comprising at least one of THF, GBL or BDO, and recovering the hydrogenated product.

Claims (21)

1. A process for making a hydrogenated product comprising:

(a) providing a clarified fermentation broth containing an ammonium salt of succinic acid;

(b) optionally adding at least one of MAS, DAS, SA, NH 3 and NH 4 + to the broth depending on pH of the broth;

(c) distilling the broth to form an overhead that comprises water and optionally ammonia and a liquid bottoms that comprises MAS, at least some DAS, and at least about 20 wt % water;

(d) cooling and/or evaporating the bottoms, and optionally adding an antisolvent to the bottoms, to attain a temperature and composition sufficient to cause the bottoms to separate into a DAS-containing liquid portion and a MAS-containing solid portion that is substantially free of DAS;

(e) separating the solid portion from the liquid portion;

(f) recovering the solid portion;

(g) hydrogenating the solid portion in the presence of at least one hydrogenation catalyst to produce the hydrogenated product comprising at least one of THF, GBL or BDO; and

(h) recovering the hydrogenated product.

2. The process of claim 1 , further comprising purifying the second solid portion before step g.

3. The process of claim 2 , further comprising dissolving the second solid portion in a solvent to form a solution.

4. The process of claim 1 , wherein step g is conducted such that THF is recovered in a vapor phase.

5. The process of claim 1 , wherein step g is conducted such that BDO is recovered in a liquid phase.

6. The process of claim 1 , wherein the hydrogenation catalyst comprises at least one metal from Group VIII of the Periodic Table of the Elements.

7. The process of claim 6 , wherein the at least one metal consists essentially of:

(i) about 0.5 to about 10% by weight ruthenium, and

(ii) about 2.0 to about 20% by weight rhenium,

based on total weight of the catalyst.

8. The process of claim 7 , further comprising about 0.1 to about 5.0% by weight of tin.

9. The process of claim 4 , wherein the catalyst is supported on at least one selected from the group consisting of carbon, silica, alumina, silica-alumina, silica-titania, titania, titania-alumina, barium sulfate, calcium carbonate and strontium carbonate.

10. The process of claim 1 , wherein the ammonium salt of succinic acid is selected from the group consisting of DAS and MAS.

Assignments (8)
RELEASE OF SECURITY INTEREST Recorded Mar 30, 2023
From: HERCULES TECHNOLOGY GROWTH CAPITAL, INC.; OBSIDIAN AGENCY SERVICES, INC.; MITSUI & CO., LTD.
To: LCY BIOSCIENCES INC.
Reel/Frame 063195/0068 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 15, 2020
From: BIOAMBER INC.
To: LCY BIOSCIENCES INC.
Reel/Frame 054060/0253 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Aug 16, 2017
From: BIOAMBER INC.
To: MITSUI & CO., LTD.
Reel/Frame 043576/0072 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 14, 2016
From: BIOAMBER INTERNATIONAL S.A.R.L.
To: BIOAMBER INC.
Reel/Frame 040730/0727 →
SECURITY INTEREST Recorded Jan 26, 2015
From: BIOAMBER INC.
To: OBSIDIAN AGENCY SERVICES, INC.
Reel/Frame 034816/0968 →
SECURITY AGREEMENT Recorded Jan 15, 2014
From: BIOAMBER INTERNATIONAL S.A.R.L.
To: HERCULES TECHNOLOGY GROWTH CAPITAL, INC.
Reel/Frame 032020/0468 →
SECURITY AGREEMENT Recorded Oct 25, 2013
From: BIOAMBER INC.; BIOAMBER S.A.S.; BIOAMBER INTERNATIONAL S.A.R.L.
To: HERCULES TECHNOLOGY GROWTH CAPITAL, INC.
Reel/Frame 031652/0239 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 22, 2011
From: FRUCHEY, OLAN S.; MANZER, LEO E.; DUNUWILA, DILUM; KEEN, BRIAN T.; ALBIN, BROOKE A.; CLINTON, NYE A.; DOMBEK, BERNARD D.
To: BIOAMBER INTERNATIONAL S.A.R.L.
Reel/Frame 027434/0082 →