IP Library Granted Patent US 10,428,001
Granted Patent B2
US 10,428,001 · App. 16/057,235 · Granted Oct 1, 2019

Film ozonolysis in a tubular or multitubular reactor

Inventors: Patrick Foley (New Haven, CT); Neil Burns (Freehold, NJ); Alexandre Chapeaux (New Haven, CT); Icilio Adami (Milan, IT); Antonio Milicia (Milan, IT)
Assignee: P2 SCIENCE, INC.
C07C45/40B01J10/02B01J19/247B01J19/2415B01J19/2425C02F1/78C07C51/34B01J2219/24C02F2101/30C02F2201/784C07C2601/16
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Quick Facts
Patent No.
US 10,428,001
App. No.
16/057,235
Granted
Oct 1, 2019
Kind
B2
Abstract

The disclosure relates to a method of performing ozonolysis or ozone-based oxidation on a liquid or emulsified reagent using a tubular falling firm reactor with one or multiple tubes wherein the combined ozone and carrier gas flow is co-current.

Claims (27)

1. A method of performing ozonolysis or ozone-based oxidation on a liquid or emulsified reagent using an industrial scale tubular falling film reactor with one or multiple tubes wherein the combined ozone and carrier gas flow is co-current, and wherein the ozonolysis occurs continuously without accumulation of large amounts of hazardous intermediates, and wherein the tubes are cooled by flow of a coolant; and

wherein the gas flow rate is from 10 to 1500 L/min in each of said tube or tubes.

2. The method of claim 1 , wherein the diameter of the tube(s) is between 5 mm and 5 m, and the feeding pressure of the gaseous reagent is between 0.1 and 5 bar.

3. The method of claim 1 , wherein the diameter of the tube(s) is between 5 mm and 5 m, and wherein the feeding pressure of the gaseous reagent is between 0.1 and 0.5 bar.

4. The method of claim 1 , wherein the diameter of the tube(s) is between 5 mm and 30 mm, and the feeding pressure of the gaseous reagent is between 0.1 and 5 bar.

5. The method of claim 1 , wherein the diameter of the tube(s) is between 5 and 30 mm, and wherein the feeding pressure of the gaseous reagent is between 0.1 and 0.5 bar.

6. The method of claim 1 , wherein the diameter of the tube(s) is between 10 mm and 25 mm, and the feeding pressure of the gaseous reagent is between 0.1 and 5 bar.

7. The method of claim 1 , wherein the diameter of the tube(s) is between 10 and 25 mm, and wherein the feeding pressure of the gaseous reagent is between 0.1 and 0.5 bar.

8. The method of claim 2 , wherein the gas flow rate is about 150 L/min in each of said tube or tubes.

9. The method of claim 3 , wherein the gas flow rate is about 150 L/min in each of said tube or tubes.

10. The method of claim 4 , wherein the gas flow rate is about 150 L/min in each of said tube or tubes.

11. The method of claim 5 , wherein the gas flow rate is about 150 L/min in each of said tube or tubes.

12. The method of claim 6 , wherein the gas flow rate is about 150 L/min in each of said tube or tubes.

13. The method of claim 7 , wherein the gas flow rate is about 150 L/min in each of said tube or tubes.

14. The method of claim 1 , wherein the gas flow rate is about 150 L/min in each of said tube or tubes.

15. The method of claim 1 , wherein the coolant maintains the temperature between 0° C. and 50° C.

16. A method of performing ozonolysis or ozone-based oxidation on a liquid or emulsified reagent with a gaseous reagent comprising ozone and one or more carrier gases, the method comprising:

(a) feeding the liquid or emulsified reagent from a common liquid or emulsified reagent feeding chamber that is maintained completely full through annular slots and into a plurality of parallel and substantially identical tubes, as to form a liquid or emulsified reagent film on the internal surface of each tube;

(b) feeding the gaseous reagent through the annular slots and into the tubes from a gaseous reagent feeding chamber, the feeding pressure of the gaseous reagent being substantially the same as the pressure loss from the gaseous reagent flow through the tubes containing the liquid or emulsified reagent film, but less than the feeding pressure of the liquid or emulsified reagent; and

(c) cooling the tubes by flowing a liquid coolant through a housing surrounding the tubes; and wherein the gas flow rate in each of said parallel tubes is from 10 to 1500 L/min.

17. The method of claim 16 , further comprising (d) collecting reaction product(s) and gaseous reagent exhaust in one or more product containers connected to the end of the tubes opposite that connected to the annular slots.

18. The method of claim 1 , wherein the length of the tubes is greater than 1 m and less than 20 m.

19. The method of claim 16 , wherein the length of the tubes is greater than 1 m and less than 20 m.

20. The method of claim 1 , wherein the liquid or emulsified reagent comprises hydroxycitronellene.

21. The method of claim 1 , wherein the liquid or emulsified reagent comprises methoxycitronellene.

22. The method of claim 21 , wherein the product is methoxymelonal.

23. The method of claim 16 , wherein the gas flow rate in each of said parallel tubes is about 150 L/min.

Assignments (4)
RELEASE OF SECURITY INTEREST Recorded Feb 6, 2023
From: HG VENTURES LLC
To: P2 SCIENCE, INC.
Reel/Frame 062650/0301 →
SECURITY INTEREST Recorded Dec 3, 2022
From: P2 SCIENCE, INC.
To: HG VENTURES LLC
Reel/Frame 062050/0152 →
SECURITY INTEREST Recorded May 15, 2020
From: P2 SCIENCE, INC.
To: WEBSTER BANK, NATIONAL ASSOCIATION
Reel/Frame 052678/0391 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 9, 2019
From: FOLEY, PATRICK; BURNS, NEIL; CHAPEAUX, ALEXANDRE; ADAMI, ICILIO; MILICIA, ANTONIO
To: P2 SCIENCE, INC.
Reel/Frame 049133/0834 →
Continuity (4)
Continuation 15320250
Provisional Application 62163022 · May 18, 2015
Provisional Application 62015311 · Jun 20, 2014
Related Publication 20190039982A1 · Feb 7, 2019