Use of tetrahydrobenzoxazines as stabilisers

Patent metadata

Field	Value
Publication number	US-9840608-B2
Application number	US-201514665952-A
Country	US
Kind code	B2
Filing date	Mar 23, 2015
Priority date	Jul 26, 2005
Publication date	Dec 12, 2017
Grant date	Dec 12, 2017

Abstract

The use of tetrahydrobenzoxazines I

where R 1 is a hydrocarbyl radical and R 2 , R 3 , R 4 and R 5 are each independently hydrogen atoms, hydroxyl groups or hydrocarbyl radicals, and where R 2 to R 5 may also form a second and a third tetrahydrooxazine ring, with the proviso that at least one of the substituents has from 4 to 3000 carbon atoms and the remaining substituents, when they are hydrocarbyl radicals, each have from 1 to 20 carbon atoms, as stabilizers for stabilizing inanimate organic material, especially turbine fuels, against the action of light, oxygen and heat.

First claim

What is claimed is:

1. A method to operate a turbine engine, comprising:
adding a tetrahydrobenzoxazine of formula I to a liquid turbine fuel comprising kerosene to obtain a stabilized turbine fuel;

supplying the turbine engine with the stabilized turbine fuel through fuel lines; and
combusting the stabilized fuel in the turbine;
wherein the liquid turbine fuel is selected from the group consisting of Jet Fuel A, Jet Fuel A-1, Jet Fuel B, Jet Fuel JP-4, JP-5, JP-7, JP-8 and JP-8+100 according to ASTM D 1655 and DEF STAN 91-91, and
wherein in formula (I)
R 1 is a hydrocarbyl radical selected from the group consisting of a C 16 to C 20 alkenyl group and a polyisobutenyl group having a number-average molecular weight of from 200 to 40,000,
R 6 is a hydrogen atom or a C 1 - to C 4 -alkyl radical, and
R 2 , R 3 , R 4 and R 5 are each independently a hydrogen atom, a hydroxyl group or a hydrocarbyl group having from 1 to 3000 carbon atoms optionally substituted with one or more moieties selected from the group consisting of O, S and NR 6
R 4 may optionally be a radical of formula Y:

wherein
R 1 , R 2 , R 3 and R 5 are each as defined above and X is a hydrocarbon bridging element which consists of one or more isobutene units or comprises one or more isobutene units, or
R 4 may also be a radical of formula Z or Z′

wherein
R 1 , R 2 , R 3 and R 5 are each as defined above and R 10 and R 11 are each independently hydrogen or a C 1 - to C 10 -alkyl radical,
R 2 and R 3 or R 3 and R 4 or R 4 and R 5 , together with the part-structure —O—CH 2 —NR 7 —CH 2 — attached to the benzene ring, optionally form a second tetrahydrooxazine ring, or the substituents R 2 and R 3 and R 4 and R 5 , together with the part-structures —O—CH 2 —NR 7 —CH 2 - and —O—CH 2 —NR 8 —CH 2 — attached to the benzene ring, optionally form a second and a third tetrahydrooxazine ring, and
R 7 and R 8 are each independently a hydrocarbyl group selected from the group consisting of a C 16 to C 20 alkenyl group and a polyisobutenyl group having a number-average molecular weight of from 200 to 40,000,
with the proviso that R 2 , R 3 , R 4 , R 5 , when they are hydrocarbyl radicals, each have from 1 to 20 carbon atoms.

2. The method of claim 1 , wherein at least one of R 2 , R 3 , R 4 , R 5 , R 7 and R 8 is a polyisobutenyl group having a number-average molecular weight M n of from 200 to 40 000.

3. The method of claim 2 , wherein at least one of R 2 , R 4 , R 7 and R 8 is a polyisobutenyl group having a number-average molecular weight M n of from 200 to 40 000.

4. The method of claim 1 , wherein
the members of the group consisting of R 2 , R 3 , R 4 , R 5 , R 7 and R 8 which are not substituents having from 4 to 3000 carbon atoms or polyisobutenyl radicals having a number-average molecular weight M n of from 200 to 40 000 each independently is hydrogen atoms, hydroxyl or a linear or branched C 1 - to C 4 -alkyl.

5. The method of claim 1 , wherein
R 3 and R 4 or R 4 and R 5 , together with a part-structure —O—CH 2 —NR 7 —CH 2 — oxygen-attached via the substituent R 4 form a second tetrahydrooxazine ring.

6. The method of claim 1 wherein a content of the tetrahydrobenzoxazine of formula I is from 0.0001 to 1% by weight of the turbine fuel.

7. The method of claim 6 , further comprising adding at least one additive to the turbine fuel, wherein the additive is selected from the group consisting of a polyalkenylsuccinic anhydride, a polyalkenylthiophosphonate ester and a Mannich adduct of an aromatic hydroxyl compound with an aldehyde and a monoamine or a diamine.

8. The method of claim 7 wherein a content of each additive in the turbine fuel is from 0.0001 to 1% by weight.

Assignees

• Basf Se

Inventors

• Lange Arno
• Mach Helmut
• Rath Hans Peter
• Posselt Dietmar

Classifications

• C10L1/2691

  Compounds of uncertain formula; reaction of organic compounds (hydrocarbons acids, esters) with Px Sy, Px Sy Halz or sulfur and phosphorus containing compounds · CPC title

• C10L2230/081

  Anti-oxidants · CPC title

• C10L1/2283

  containing one or more carbon to nitrogen double bonds, e.g. guanidine, hydrazone, semi-carbazone, azomethine (C10L1/221, C10L1/226 take precedence) · CPC title

• C10L1/265

  oxygen and/or sulfur bonds · CPC title

• C10L2200/0259

  Nitrogen containing compounds · CPC title