IP Library Granted Patent US 9,504,933
Granted Patent B2
US 9,504,933 · App. 13/973,142 · Granted Nov 29, 2016

Hydrocarbon feed flexible high pressure nitration plant design

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Quick Facts
Patent No.
US 9,504,933
App. No.
13/973,142
Granted
Nov 29, 2016
Kind
B2
Abstract

Disclosed is an apparatus for synthesizing nitroalkanes by reaction of a hydrocarbon feedstock with aqueous nitric acid. The apparatus may be designed such that it can synthesize more than one nitroalkane using the same equipment.

Claims (23)

1. An apparatus for selectively synthesizing at least a first nitroalkane using a first feedstock and at least a second nitroalkane using a second feedstock, wherein the first feedstock comprises a first hydrocarbon and the second feedstock comprises a second, different hydrocarbon, said apparatus comprising:

a reactor for selectively reacting the first feedstock and the second feedstock with aqueous nitric acid to produce a reaction product stream, wherein the reaction product stream comprises the first nitroalkane when the first feedstock is used and comprises the second nitroalkane when the second feedstock is used;

a separating system for forming a gas-recovered aqueous phase and a gas-recovered oil phase from the reaction product stream; and

a recovery system for recovering the first nitroalkane from at least one of the gas-recovered aqueous phase and the gas-recovered oil phase when the first feedstock is used and for recovering the second nitroalkane from at least one of the gas-recovered aqueous phase and the gas-recovered oil phase when the second feedstock is used;

wherein the recovery system comprises at least one stripping apparatus.

2. An apparatus according to claim 1 , wherein at least a third nitroalkane is synthesized using a third feedstock, and wherein the third feedstock comprises a third hydrocarbon that is different from the first hydrocarbon and the second hydrocarbon.

3. An apparatus according to claim 2 , wherein at least a fourth nitroalkane is synthesized using a fourth feedstock, and wherein the fourth feedstock comprises a fourth hydrocarbon that is different from the first hydrocarbon, the second hydrocarbon, and the third hydrocarbon.

4. An apparatus according to claim 1 , wherein the first hydrocarbon is propane, and wherein the first nitroalkane is 2-nitropropane.

5. An apparatus according to claim 4 , wherein the second hydrocarbon is isobutane, and wherein the second nitroalkane is tert-nitrobutane.

6. An apparatus according to claim 1 , wherein the first hydrocarbon is cyclohexane, and wherein the first nitroalkane is nitrocyclohexane.

7. An apparatus according to claim 6 , wherein the second hydrocarbon is n-octane, and wherein when the second nitroalkane is nitro-n-octane.

8. An apparatus for selectively synthesizing at least a first nitroalkane using a first feedstock and at least a second nitroalkane using a second feedstock, wherein the first feedstock comprises a first hydrocarbon and the second feedstock comprises a second, different hydrocarbon, said apparatus comprising:

a reactor for selectively reacting the first feedstock and the second feedstock with aqueous nitric acid to produce a reaction product stream, wherein the reaction product stream comprises the first nitroalkane when the first feedstock is used and comprises the second nitroalkane when the second feedstock is used;

a cooling system for quenching the reaction product stream such that it phase separates into at least a gas phase, an oil phase, and an aqueous phase;

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

a stripper for removing dissolved organic compounds from the gas-recovered mixture to form a stripped gas-recovered mixture;

a separator for forming a combined gas-recovered aqueous phase and a combined gas-recovered oil phase from the stripped gas-recovered mixture, the oil phase, and the aqueous phase; and

a recovery system for recovering the first nitroalkane from at least one of the combined gas-recovered aqueous phase and the combined gas-recovered oil phase when the first feedstock is used and for recovering the second nitroalkane from at least one of the gas-recovered aqueous phase and the gas-recovered oil phase when the second feedstock is used;

wherein the recovery system comprises at least one stripping apparatus.

9. An apparatus according to claim 8 , wherein the first feedstock comprises propane, and wherein the first nitroalkane is 2-nitropropane.

10. An apparatus according to claim 9 , wherein the second feedstock comprises isobutane, and wherein the second nitroalkane is tert-nitrobutane.

11. An apparatus according to claim 8 , wherein first feedstock comprises cyclohexane, and wherein the first nitroalkane is nitrocyclohexane.

12. An apparatus according to claim 11 , wherein the second feedstock comprises n-octane, and wherein the second nitroalkane is nitro-n-octane.

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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 10, 2014
From: SAWANT, MAHESH M.
To: DOW CHEMICAL INTERNATIONAL PRIVATE LIMITED
Reel/Frame 034135/0957 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 10, 2014
From: DOW CHEMICAL INTERNATIONAL PRIVATE LIMITED
To: DOW INTERNATIONAL TECHNOLOGY CORPORATION
Reel/Frame 034136/0015 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 10, 2014
From: DOW INTERNATIONAL TECHNOLOGY CORPORATION
To: THE DOW CHEMICAL COMPANY
Reel/Frame 034136/0088 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 10, 2014
From: THE DOW CHEMICAL COMPANY
To: DOW GLOBAL TECHNOLOGIES INC.
Reel/Frame 034136/0184 →
CHANGE OF NAME Recorded Nov 10, 2014
From: DOW GLOBAL TECHNOLOGIES INC.
To: DOW GLOBAL TECHNOLOGIES LLC
Reel/Frame 034214/0661 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 10, 2014
From: TRAUTH, DANIEL M.
To: ANGUS CHEMICAL COMPANY
Reel/Frame 034135/0645 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 10, 2014
From: DIXIT, RAVINDRA S.; PENDERGAST, JOHN G., JR
To: DOW GLOBAL TECHNOLOGIES INC.
Reel/Frame 034135/0181 →