IP Library Granted Patent US 10,189,756
Granted Patent B2
US 10,189,756 · App. 15/204,462 · Granted Jan 29, 2019

Adiabatic plug flow reactors and processes incorporating the same

Inventors: Max M. Tirtowidjojo (Midland, MI); Hua Bai (Midland, MI); Debashis Chakraborty (Midland, MI); Juergen Eiffler (Midland, MI); Heinz Groenewald (Midland, MI); Kurt F. Hirsekorn (Midland, MI); Manfred Kokott (Midland, MI); William J. Kruper (Midland, MI); Thomas U. Luebbe (Midland, MI); Thomas J. Parsons (Midland, MI); Avani Maulik Patel (Midland, MI); Marcus Wobser (Midland, MI)
Assignee: BLUE CUBE IP LLC
C07C17/206B01J19/006B01J19/0013B01J19/0026B01J19/2405B01J19/2415C07C17/269B01J2219/00054B01J2219/00063B01J2219/00155B01J2219/00162B01J2219/00166B01J2219/00247
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Quick Facts
Patent No.
US 10,189,756
App. No.
15/204,462
Granted
Jan 29, 2019
Kind
B2
Abstract

The present invention provides adiabatic plug flow reactors suitable for the production of chlorinated and/or fluorinated propene and higher alkenes from the reaction of chlorinated and/or fluorinated alkanes and chlorinated and/or fluorinated alkenes. The reactors comprise one or more designs that minimize the production of by-products at a desired conversion.

Claims (22)

1. A process for producing a chlorinated and/or fluorinated propene, having the formula CH 2-c-g Cl c F g =CH 1-d-h Cl d F h- CH 3-e-f Cl e F f wherein c is 0-2, d is 0-1, e is 0-3, f is 0-3, g is 0-2 and h is 0-1, while c+g≤2, d+h≤1, and e+f≤3 which process comprises providing a feed comprising methanes, chloromethanes, fluoromethanes, or chlorofluoromethanes, having the formula CH 4-a-b Cl a F b , wherein each a and b are independently 0-3 and 4-a-b is greater than 0, and a chloroethylene or chlorofluoroethylene in an adiabatic plug flow reactor wherein the reactor is operably disposed relative to a mixer having a diameter and shape that are the same as those of the reactor, the reactants flow through the mixer, and the reactor further comprises a collector having the same shape and/or diameter as the reactor; wherein a turbulence flow region exists within at least a portion of the reactor having a Reynolds number (Re) of at least 2100, wherein the adiabatic plug flow reactor further comprises at least one of i) an insulation material, ii) a temperature controller for the reactor effluent; or iii) one or more temperature and flow controllers for one or more reactants, initiator(s) and/or diluents; wherein the reactor provides reduced backmixing and/or recirculation prior to entry into, or upon exit from, the reactor.

2. The process of claim 1 , wherein the reactor comprises a collector configured to accept a reactor effluent from the reactor and further configured to minimize backmixing and/or recirculation.

3. The process of claim 1 , wherein the reactor comprises a mixer configured to accept one or more reactants, initiators, and/or diluents and further configured to minimize backmixing and/or recirculation of the same.

4. The process of claim 1 , wherein the reactor inlet temperature is at least 370° C. or the reactor productivity is at least 40 gr/hr/l.

5. The process of claim 1 , wherein the reactor

i. minimizes heat transfer to and/or from the reactor;

ii. optimizes the flow of the reaction mixture at a boundary between the reaction mixture and at least a portion of at least one reactor tube wall;

iii. facilitates a reduction of the temperature of a reactor effluent to a temperature below which substantial formation of by-products does not occur, and/or

iv. allows the production rate in the reactor to be adjusted by controlling the temperature of the reactor effluent.

6. The process of claim 5 , wherein the reactor

i. minimizes heat transfer to and/or from the reactor;

ii. optimizes the flow of the reaction mixture at a boundary between the reaction mixture and at least a portion of at least one reactor tube wall;

iii. facilitates a reduction of the temperature of a reactor effluent to a temperature below which substantial formation of by-products does not occur, and

iv. allows the production rate in the reactor to be adjusted by controlling the temperature of the reactor effluent.

7. The process for preparing 2,3,3,3-tetrafluoroprop-1-ene (HFO-1234yf) or 1,3,3,3-tetrafluoroprop-1-ene (HFO-1234ze) comprising preparing 1,1,2,3-tetrachloropropene by the process of claim 1 , and converting the 1,1,2,3-tetrachloropropene into 2,3,3,3-tetrafluoroprop-1-ene (HFO-1234yf) or 1,3,3,3-tetrafluoroprop-1-ene (HFO-1234ze).

8. The process for preparing 2,3,3,3-tetrafluoroprop-1-ene (HFO-1234yf) or 1,3,3,3-tetrafluoroprop-1-ene (HFO-1234ze) comprising preparing 1,1,2,3-tetrachloropropene by the process of claim 2 , and converting the 1,1,2,3-tetrachloropropene into 2,3,3,3-tetrafluoroprop-1-ene (HFO-1234yf) or 1,3,3,3-tetrafluoroprop-1-ene (HFO-1234ze).

9. The process for preparing 2,3,3,3-tetrafluoroprop-1-ene (HFO-1234yf) or 1,3,3,3-tetrafluoroprop-1-ene (HFO-1234ze) comprising preparing 1,1,2,3-tetrachloropropene by the process of claim 3 , and converting the 1,1,2,3-tetrachloropropene into 2,3,3,3-tetrafluoroprop-1-ene (HFO-1234yf) or 1,3,3,3-tetrafluoroprop-1-ene (HFO-1234ze).

10. The process for preparing 2,3,3,3-tetrafluoroprop-1-ene (HFO-1234yf) or 1,3,3,3-tetrafluoroprop-1-ene (HFO-1234ze) comprising preparing 1,1,2,3-tetrachloropropene by the process of claim 4 , and converting the 1,1,2,3-tetrachloropropene into 2,3,3,3-tetrafluoroprop-1-ene (HFO-1234yf) or 1,3,3,3-tetrafluoroprop-1-ene (HFO-1234ze).

11. The process for preparing 2,3,3,3-tetrafluoroprop-1-ene (HFO-1234yf) or 1,3,3,3-tetrafluoroprop-1-ene (HFO-1234ze) comprising preparing 1,1,2,3-tetrachloropropene by the process of claim 5 , and converting the 1,1,2,3-tetrachloropropene into 2,3,3,3-tetrafluoroprop-1-ene (HFO-1234yf) or 1,3,3,3-tetrafluoroprop-1-ene (HFO-1234ze).

12. The process for preparing 2,3,3,3-tetrafluoroprop-1-ene (HFO-1234yf) or 1,3,3,3-tetrafluoroprop-1-ene (HFO-1234ze) comprising preparing 1,1,2,3-tetrachloropropene by the process of claim 6 , and converting the 1,1,2,3-tetrachloropropene into 2,3,3,3-tetrafluoroprop-1-ene (HFO-1234yf) or 1,3,3,3-tetrafluoroprop-1-ene (HFO-1234ze).

13. The process of claim 2 , wherein the reactor comprises a mixer configured to accept one or more reactants, initiators, and/or diluents and further configured to minimize backmixing and/or recirculation of the same.

14. The process of claim 13 , wherein the chlorinated and/or fluorinated alkane and chlorinated and/or fluorinated alkene is selected from methanes, chloromethanes, fluoromethanes, or chlorofluoromethanes, having the formula CH 4-a-b Cl a F b , wherein each a and b are independently 0-3 and 4-a-b is greater than 0.

Assignments (6)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 29, 2016
From: EIFFLER, JUERGEN; GROENEWALD, HEINZ; KOKOTT, MANFRED; LUEBBE, THOMAS U.; WOBSER, MARCUS
To: DOW DEUTSCHLAND GMBH & CO. OHG
Reel/Frame 040444/0952 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 29, 2016
From: TIRTOWIDJOJO, MAX M.; BAI, HUA; CHAKRABORTY, DEBASHIS; HIRSEKORN, KURT F.; KRUPER, WILLIAM J., JR.; PARSONS, THOMAS J.; PATEL, AVANI M.
To: DOW GLOBAL TECHNOLOGIES INC.
Reel/Frame 040445/0160 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 29, 2016
From: DOW DEUTSCHLAND GMBH & CO. OHG
To: THE DOW CHEMICAL COMPANY
Reel/Frame 040446/0842 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 29, 2016
From: THE DOW CHEMICAL COMPANY
To: DOW GLOBAL TECHNOLOGIES INC.
Reel/Frame 040446/0864 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 29, 2016
From: DOW GLOBAL TECHNOLOGIES LLC
To: BLUE CUBE IP LLC
Reel/Frame 040446/0950 →
CHANGE OF NAME Recorded Nov 29, 2016
From: DOW GLOBAL TECHNOLOGIES INC.
To: DOW GLOBAL TECHNOLOGIES LLC
Reel/Frame 040697/0840 →
Continuity (3)
Division 12901383 · Oct 8, 2010
Provisional Application 61250023 · Oct 9, 2009
Related Publication 20160347692A1 · Dec 1, 2016