[Enthalpy]

Could the Kharasch addition make intermediates to cyclopropanes, azetidines, dihydroazetes? It puts halogens at proper distance.

Kharasch to 1,3-dihalopropane can have some merit. Then, cyclopropane and azetidine (picture) follow usual paths. R≠H improves the yield and can be removed later. R=cPr makes an efficient but volatile fuel.

Kharasch to (methyl)allyl chloride is less direct than usual routes. I see no merit for cyclopropene nor methylcyclopropene synthesis. No picture.

The scheme to dihydroazete (picture) obtains a halogen next to the amine. HX elimination is easier here than with a chloramine which might also create nasty compounds. I drew NH₃, but a primary amine raises the yied from poor to excellent with dihalopropane, so some rest should be present and removed. The 2-haloazetidine may have more uses.

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When some compounds can run away thermally, the reactor must try to prevent it by design. Here ethylene may polymerize for instance.

I hope the thermal inertia of a material in close contact with said compound stabilizes it over a time scale range. A sturdy construction would resemble the catalyst I described there
  scienceforums
using a honeycomb winding of wire(s) sintered together and the flow outwards. The wires can have varied diameters and carry an inhibitor for the unwanted reaction. They can also carry a catalyst for the desired reaction. Or both, spread over the thickness or as a sandwich, for instance inhibitor - catalyst - inhibitor.

If the reactor needs pressure (apparently Kharasch doesn't usually), the unwanted reaction possibly happens already at the compressor. A Tesla compressor, which stacks many fine smooth spinning disks, would group both functions at one place for added safety. Expansion could happen in a Tesla turbine
  wikipedia

Marc Schaefer, aka Enthalpy

[Enthalpy]

A hypothetic path to cPr-terminated ladderanes, looking much cheaper than here on August 23, 2023.

Andrist et al rearranged cyclopentadiene with light to bicyclopentene (housene), verified by Orgsyn
  orgsyn.org

The yield is very low, but the feed and light are cheap. An industrial process would harvest the bicyclopentene continuously before light isomerizes it, and would reinject the isomers. How? Err... GC at Orgsyn.

Maybe bicyclopentene is so much more reactive that an excess of acetylene pre-empts it. Or a wavelength excites selectively bicyclopentene which then reacts with the acetylene excess.

Marc Schaefer, aka Enthalpy