1. An acid-catalyzed method of producing a compound of formula I:
wherein:
R1 and R3 are each chlorine;
R2 is hydrogen, aryl, alkyl, alkoxy, phenoxy, anilino, amino, halo, acyloxy, or (acyloxy)alkyl;
R5 is hydrogen, C1\u2013C7 alkyl, C2\u2013C7 alkenyl, C2\u2013C7 alkynyl, arylalkyl, or aryl;
R4 is, alkylcarboxy, C2\u2013Cm alkenyl, alkynyl, alkenylcarboxy, hydroxy, hydroxyalkyl, C1\u2013Cn alkoxy, nitro, halo, trihalomethyl, amido, carboxamido, carboxy, sulfonyl, sulfonamido, amino, mercapto, or 2-methylbut-2-en-4-yl, wherein n is an integer from 2\u201312, and m is an integer from 3\u201312; and
R6 and R7 form part of an aromatic ring wherein said aromatic ring may be substituted;
which method comprises:
reacting a substituted or unsubstituted 2,5-dichloro-1,4-benzoquinone compound of formula II:
wherein R1, R2 and R3 are as defined above;
with at least one pyrrole of the formula III:
wherein R4\u2013R7 are as defined above;
in a polar organic solvent and in the presence of an acid to produce a first intermediate; and then
reacting the first intermediate with an oxidization agent to produce said compound of formula I.
2. The method of claim 1, wherein n is 2\u20137 and m is 3\u20137.
3. The method of claim 1, wherein the organic solvent is an aprotic solvent selected from the group consisting of tetrahydrofuran (THF), acetonitrile, and mixtures thereof.
4. The method of claim 1, wherein the acid is HCl.
5. The method of claim 1, wherein the acid is H2SO4.
6. The method of claim 1, wherein the acid is AcOH.
7. The method of claim 1, wherein the oxidization agent is dichlorodicyanobenzoquinone.
8. The method of claim 1, wherein the oxidization agent is Ag2CO3.
9. The method of claim 1, wherein the reaction is conducted at a temperature from about \u221210\xb0 C. to about 100\xb0 C.
The claims below are in addition to those above.
All refrences to claim(s) which appear below refer to the numbering after this setence.
1. A pressure vessel comprising:
a first working fluid compartment;
a second working fluid compartment; and
a mixing trigger that selectively triggers mixing of the first working fluid from the first working fluid compartment compartment with the second working fluid from the second working fluid compartment within the pressure vessel.
2. The pressure vessel of claim 1, wherein the second working fluid compartment is encompassed by the first working fluid compartment.
3. The pressure vessel of claim 2, wherein the second working fluid compartment includes a flexible bladder.
4. The pressure vessel of claim 1, wherein the second working fluid compartment is separated from the first working fluid compartment with a flexible membrane.
5. The pressure vessel of claim 1, wherein the mixing trigger includes a valve that selectively opens to trigger the mixing of the first working fluid with the second working fluid.
6. The pressure vessel of claim 1, wherein the mixing trigger includes a puncturing device that selectively punctures one or both of the first working fluid compartment and the second working fluid compartment to trigger the mixing of the first working fluid with the second working fluid.
7. The pressure vessel of claim 1, wherein the mixing trigger includes an explosive device that selectively ruptures one or both of the first working fluid compartment and the second working fluid compartment to trigger the mixing of the first working fluid with the second working fluid.
8. The pressure vessel of claim 1, wherein the mixing trigger includes a dissolvable portion of the second working fluid compartment that dissolves in one or both of the first working fluid and the second working fluid to trigger the mixing of the first working fluid with the second working fluid.
9. The pressure vessel of claim 1, further comprising:
a mixing monitor that monitors the pressure vessel for mixing of the first working fluid with the second working fluid.
10. The pressure vessel of claim 1, wherein the first working fluid includes an oxidizer, the second working fluid includes a fuel, and a mixture of the first working fluid and the second working fluid includes a monopropellant.
11. A method comprising:
providing a pressure vessel with a first working fluid compartment and a second working fluid compartment; and
selectively mixing the first working fluid from the first working fluid compartment with the second working fluid from the second working fluid compartment within the pressure vessel.
12. The method of claim 11, wherein the second working fluid compartment is encompassed by the first working fluid compartment.
13. The method of claim 12, wherein the second working fluid compartment includes a flexible bladder.
14. The method of claim 11, wherein the first working fluid compartment is separated from the second working fluid compartment with a flexible membrane.
15. The method of claim 11, wherein the selectively mixing operation includes opening a valve to trigger the mixing of the first working fluid with the second working fluid.
16. The method of claim 11, wherein the selectively mixing operation includes puncturing one or both of the first working fluid compartment and the second working fluid compartment to trigger the mixing of the first working fluid with the second working fluid.
17. The method of claim 11, wherein the selectively mixing operation includes igniting an explosive device to rupture one or both of the first working fluid compartment and the second working fluid compartment and trigger the mixing of the first working fluid with the second working fluid.
18. The method of claim 11, wherein the selectively mixing operation includes dissolving a portion of the second working fluid compartment in one or both of the first working fluid and the second working fluid to trigger the mixing of the first working fluid with the second working fluid.
19. The method of claim 11, further comprising:
monitoring the pressure vessel for mixing of the first working fluid with the second working fluid.
20. The method of claim 11, wherein the first working fluid includes an oxidizer, the second working fluid includes a fuel, and a mixture of the first working fluid and the second working fluid includes a monopropellant.
21. A method comprising:
selectively mixing fuel with oxidizer within a pressure vessel;
discharging the mixed fuel and oxidizer from the pressure vessel; and
exothermically reacting the mixed and discharged fuel and oxidizer.
22. The method of claim 19, wherein one or both of work and thrust are extracted from the exothermically reacting fuel and oxidizer.