IP Library Granted Patent US 8,193,375
Granted Patent B2
US 8,193,375 · App. 13/213,565 · Granted Jun 5, 2012

Processes for the production of hydrogenated products

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 8,193,375
App. No.
13/213,565
Granted
Jun 5, 2012
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 (25)

1. A process for making a hydrogenated product comprising:

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

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

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

(d) separating the first solid portion from the first liquid portion;

(e) recovering the first solid portion;

(f) dissolving the first solid portion in water to produce an aqueous MAS solution;

(g) distilling the aqueous MAS solution at a temperature and pressure sufficient to form a second overhead that comprises water and ammonia, and a second bottoms that comprises a major portion of SA, a minor portion of MAS, and water;

(h) cooling the second bottoms to cause the second bottoms to separate into a second liquid portion and a second solid portion that consists essentially of SA and is substantially free of MAS;

(i) separating the second solid portion from the second liquid portion;

(j) recovering the second solid portion;

(k) 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

(l) recovering the hydrogenated product.

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

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 k is conducted such that THF is recovered in a vapor phase.

5. The process of claim 1 , wherein step k 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 1 , 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 063192/0882 →
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 Jan 12, 2012
From: BIOAMBER S.A.S.
To: BIOAMBER INTERNATIONAL S.A.R.L.
Reel/Frame 027522/0874 →