Film ozonolysis in a tubular or multitubular reactor

Patent metadata

Field	Value
Publication number	US-10934239-B2
Application number	US-201916541065-A
Country	US
Kind code	B2
Filing date	Aug 14, 2019
Priority date	Jun 20, 2014
Publication date	Mar 2, 2021
Grant date	Mar 2, 2021

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.

First claim

What is claimed is:

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 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;
wherein the liquid or emulsified reagent comprises a compound selected from hydroxycitronellene, methoxycitronellene, a rose ketone, fatty acid methyl esters, triglycerides, fatty alcohols, fatty esters, diterpenes, sesquiterpenes, monoterpenes, allyl ethers, alpha olefins, rosin acids, tertiary amines, alkenes, alkynes, amides, carboxylic acids, and aromatic compounds, provided that said compound is susceptible to ozone oxidation.

2. The method of claim 1 , wherein method comprises two or more industrial scale tubular falling film reactors with multiple tubes connected in series to process a continuous stream of the liquid or emulsified reagent.

3. The method of claim 1 , wherein the carrier gas is selected from air, oxygen (O 2 ), and an oxygen (O 2 )/nitrogen (N 2 ) mixture.

4. The method of claim 3 , wherein the carrier gas is air and the ozone concentration in the carrier gas is from 2.5% to 10%.

5. The method of claim 1 , wherein the liquid or emulsified reagent is an emulsion in water.

6. The method of claim 1 , wherein the reactor comprises the multiple tubes in parallel enclosed in a cylindrical reactor.

7. The method of claim 1 , wherein the diameter of the tube(s) is between 5 mm and 30 mm.

8. The method of claim 7 , wherein the diameter of the tube(s) is between 10 mm and 25 mm.

9. The method of claim 1 , wherein the gas flow rate is from 10 to 1500 L/min in each of said tube or tubes.

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

11. The method of claim 1 , wherein the tubes are between 1 and 7 meters in length or wherein the tubes are about 6 meters in length, or both.

12. A method of performing ozonolysis or ozone-based oxidation on a liquid or emulsified reagent using an industrial scale tubular falling film reactor with 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, wherein the liquid or emulsified reagent comprises a fatty acid susceptible to ozone oxidation, wherein the carrier gas is air and the ozone concentration in the carrier gas is from 2.5% to 10%.

13. The method of claim 1 , wherein the liquid or emulsified reagent comprises a compound selected from hydroxycitronellene, methoxycitronellene, fatty acid methyl esters, fatty alcohols, diterpenes, sesquiterpenes, and monoterpenes, provided that said compound is susceptible to ozone oxidation.

14. The method of claim 13 , wherein the liquid or emulsified reagent comprises hydroxycitronellene.

15. The method of claim 13 , wherein the liquid or emulsified reagent comprises methoxycitronellene.

16. The method of claim 13 , wherein the liquid or emulsified reagent comprises a fatty acid methyl ester.

17. The method of claim 13 , wherein the liquid or emulsified reagent comprises methyl oleate.

18. The method of claim 13 , wherein the liquid or emulsified reagent comprises abietic acid or an ester thereof, pinene, limonene, ionone, or dihydromyrcenol.

19. The method of claim 1 , wherein the product is selected from hydroxymelonal, methoxymelonal, methyl azealdehyde, nonanal, cyclocitral, or mixtures thereof.

20. The method of claim 1 , wherein the product is hydroxymelonal.

21. The method of claim 1 , wherein the product is methoxymelonal.

22. The method of claim 1 , wherein the product is a mixture of methyl azealdehyde and nonanal.

23. The method of claim 4 , wherein the carrier gas is air and the ozone concentration in the carrier gas is from 2.5% to 5%.

Assignees

• P2 Science Inc

Inventors

• Foley Patrick
• Burns Neil
• Chapeaux Alexandre
• Adami Icilio
• Milicia Antonio

Classifications

• C07C45/40 Primary

  by oxidation with ozone; by ozonolysis · CPC title

• C07C2601/16

  the ring being unsaturated · CPC title

• C02F1/78

  with ozone {(C02F1/4672 takes precedence)} · CPC title

• B01J10/02

  of the thin-film type · CPC title

• B01J2219/24

  Stationary reactors without moving elements inside · CPC title