IP Library Granted Patent US 8,431,754
Granted Patent B2
US 8,431,754 · App. 12/879,824 · Granted Apr 30, 2013

Process for nitroalkane recovery by aqueous phase recycle to nitration reactor

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 8,431,754
App. No.
12/879,824
Granted
Apr 30, 2013
Kind
B2
Abstract

Disclosed are a process and an apparatus for synthesizing nitroalkanes by reaction of a hydrocarbon feedstock with aqueous nitric acid. Energy and capital costs may be reduced by recycling a majority of the aqueous phase back to the reactor.

Claims (35)

1. A process for synthesizing at least one nitroalkane, the process comprising:

reacting a hydrocarbon feedstock with aqueous nitric acid in a reactor at a reactor pressure and a reaction temperature, such that a product stream comprising nitrated compounds and byproducts is formed;

separating the product stream into at least an oil phase, a gas phase, and an aqueous phase, wherein the oil phase and the aqueous phase contain nitrated compounds;

dividing the aqueous phase into a first aqueous stream and a second aqueous stream upstream of an absorber;

returning the first aqueous stream to the reactor;

supplying the second aqueous stream to the absorber; and

recovering the at least one nitroalkane from at least one of the oil phase and the second aqueous stream.

2. A process according to claim 1 further comprising:

absorbing water-soluble and oil-soluble components from the gas phase to form a gas-recovered mixture;

separating a gas-recovered aqueous phase from the gas-recovered mixture; and

introducing the gas-recovered aqueous phase to a stripping apparatus to recover the at least one nitroalkane.

3. A process according to claim 1 wherein between about 65 and 85 percent of the aqueous phase is divided into the first aqueous stream.

4. A process according to claim 1 wherein the aqueous nitric acid is added to the reactor at a 10 to 50 weight percent solution.

5. A process according to claim 4 wherein the aqueous nitric acid is added to the reactor at a 15 to 40 weight percent solution.

6. A process according to claim 5 wherein the aqueous nitric acid is added to the reactor at a 18 to 35 weight percent solution.

7. A process according to claim 1 wherein the molar ratio of hydrocarbon to nitric acid is at least about 1.2:1.

8. A process according to claim 1 wherein the reactor pressure is at least about 1000 psi.

9. A process according to claim 1 wherein the reaction temperature is between about 215 and 325 degrees Celsius.

10. A process according to claim 1 wherein the reaction temperature is greater than 230 degrees Celsius.

11. A process according to claim 1 wherein the reaction temperature is 290 degrees Celsius or less.

12. A process according to claim 1 wherein the reactor is a downflow configured reactor.

13. A process according to claim 1 wherein the reactor is a packed reactor.

14. A process according to claim 1 wherein the reactor is an un-packed reactor.

15. The process according to claim 1 , wherein the at least one nitroalkane is 2-nitropropane.

16. The process according to claim 1 , wherein the at least one nitroalkane is 2,2-nitropropane.

17. A process for synthesizing at least one nitroalkane, the process comprising:

reacting a hydrocarbon feedstock with aqueous nitric acid in a reactor at a reactor pressure and a reaction temperature, such that a product stream of nitrated compounds and byproducts is formed;

quenching the product stream to separate the product stream into at least an oil phase, a gas phase, and an aqueous phase;

dividing the aqueous phase into a first aqueous stream and a second aqueous stream upstream of an absorber;

returning the first aqueous stream to the reactor;

supplying the second aqueous stream to the absorber;

combining the oil phase, the gas phase, and the second aqueous stream in the absorber;

absorbing water-soluble and oil-soluble components from the gas phase into the oil phase and the second aqueous stream to form a gas-recovered mixture;

separating a gas-recovered aqueous phase from the gas-recovered mixture; and

recovering the at least one nitroalkane from at least one of the oil phase and the second aqueous stream.

Assignments (13)
CHANGE OF NAME Recorded Feb 27, 2024
From: ANGUS CHEMICAL COMPANY
To: ADVANCION CORPORATION
Reel/Frame 066697/0518 →
PATENT SECURITY AGREEMENT (1ST LIEN) Recorded Dec 1, 2020
From: ANGUS CHEMICAL COMPANY
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 054553/0706 →
PATENT SECURITY AGREEMENT (2ND LIEN) Recorded Dec 1, 2020
From: ANGUS CHEMICAL COMPANY
To: JEFFERIES FINANCE LLC, AS COLLATERAL AGENT
Reel/Frame 054553/0719 →
RELEASE OF SECURITY INTEREST Recorded Nov 24, 2020
From: JPMORGAN CHASE BANK, N.A.
To: ANGUS CHEMICAL COMPANY
Reel/Frame 054586/0231 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 20, 2015
From: DOW GLOBAL TECHNOLOGIES LLC
To: ANGUS CHEMICAL COMPANY
Reel/Frame 035213/0405 →
SECURITY AGREEMENT Recorded Feb 3, 2015
From: ANGUS CHEMICAL COMPANY
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 034881/0001 →
CHANGE OF NAME Recorded Mar 10, 2011
From: DOW GLOBAL TECHNOLOGIES INC.
To: DOW GLOBAL TECHNOLOGIES LLC
Reel/Frame 025931/0994 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 20, 2010
From: THE DOW CHEMICAL COMPANY
To: DOW GLOBAL TECHNOLOGIES INC.
Reel/Frame 025012/0017 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 17, 2010
From: DOW INTERNATIONAL TECHNOLOGY CORPORATION
To: THE DOW CHEMICAL COMPANY
Reel/Frame 025005/0504 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 16, 2010
From: DOW CHEMICAL INTERNATIONAL PRIVATE LIMITED
To: DOW INTERNATIONAL TECHNOLOGY CORPORATION
Reel/Frame 024997/0994 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 15, 2010
From: PENDERGAST, JOHN G., JR.
To: DOW GLOBAL TECHNOLOGIES INC.
Reel/Frame 024989/0389 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 15, 2010
From: TRAUTH, DANIEL M.
To: ANGUS CHEMICAL COMPANY
Reel/Frame 024989/0423 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 15, 2010
From: SAWANT, MAHESH
To: DOW CHEMICAL INTERNATIONAL PRIVATE LIMITED
Reel/Frame 024992/0672 →