The Most Important Reaction

The most important reaction in industry is the one in which you transform chemicals into money.  It’s about adding value to feedstocks in some way.  A chemical is valued because of some property.  For instance, heptane might be valued because of it’s hydrophobicity, it’s inertness, it’s moderately high boiling point, the solubility (or lack therein) of some material in it, or all of these attributes.  

Heptane is a useful example because it is often used as a substitute for hexane. It has a higher boiling point than does hexane, which raises an interesting point.  The art of synthetic chemistry is in managing reactivity.  In R&D work, when faced with sluggish reactivity, we might be tempted to find more reactive components.  For instance, if sodium tert-butoxide isn’t basic enough, try n-BuLi.  If that isn’t basic enough, try t-BuLi. This series of bases from NaOtBu to n-BuLi to t-BuLi increases in basicity, but it also increases in cost on a $/mol basis.  The hazards also increase.  

But another way to increase reactivity is to increase the reaction temperature.  It is probably the easiest and cheapest way to do it, in fact. Of course, petroleum chemists have known this for quite some time.  Hydrocarbons that are normally inert in the ordinary range of temerpatures, say -78 C to 200 C, become reactive to HF or H2SO4 or zeolites at 300 to 400 C.

A reaction that is sluggish in refluxing hexane may perk up in refluxing heptane, xylenes, or mineral oil.  Most people seem to have an aversion to running a reaction at elevated pressure. This is unfortunate and may be due in some small way to lab culture.  If monies haven’t been provided for a Parr reactor in the past, then there is an “activation barrier” to trying reactions at elevated pressure.  Also, high pressure processing in scale-up is hampered by the requirement for bigger pots & pans with higher pressure ratings.  The practical limit for high pressure in a common metal reactor vessel might be 70 or 90 psi.  general purpose production reactors have mechanical limitations that bench chemists may not have considered.  The agitator shaft has a mechanical seal that is prone to leakage.  The pot will have numerous ports with valves that can can be weak points. General purpose reactors have heating/cooling jackets on them that can leak. All reactors have pressure relief devices called rupture disks that are set to predetermined relief pressures.  Glass lined reactors may have pressure limitations due to the brittle glass that lines the interior surface of a metal pot.

It turns out that in the chemical processing industry, high pressure capability is a capacity that relatively few company’s have.  High pressure capacity is niche work and is nice to have.  Most of us have to manipulate reactivity by other means. 

5 thoughts on “The Most Important Reaction

  1. EHS

    Hexane has static and neuro-toxic issues in plant scale. That’s why heptane is used as a substitue. Not because of high boiling point.

    Reply
  2. gaussling Post author

    You point about the toxicity of hexane is correct of course. It is becoming a major reason not to use it. However, hexanes are still an item of commerce and still find use in specialty applications. Whereas a process that runs constantly, or frequently at least, may require that heptanes be used to minimize the long term worker exposure, batch reactions consisting of one or a few runs with proper PPE and environmental controls can accommodate hexane quite easily. In this case, you would probably choose hexane because of its higher vapor pressure. The reason being that you can get the residual solvent levels down to the spec. Heptane is often a real problem to remove by evaporation from some products.

    Reply
  3. wrw

    if I may digress here.

    Lets see, “THE MOST IMPORTANT REACTION”.

    I thought we were going for the grand slam.

    Well, what is it?

    Grignard? Asymmetric Hydrogenation? Stille coupling?

    The old Zeigler-Natta polymerization (a likely winner based on pounds/year – yes?)

    Or how about something as mundane as the Haber nitrogen synthesis.

    Monday we are to hear about what academic research should be doing in In the Pipeline – but maybe we can ask the question – how does one define and find the next “most important reaction”?

    Oh well, I digress.

    I personally have only worked with hexane. My reactions go to slow.

    Reply
  4. gaussling Post author

    My point was that the chemical industry was about the “transmutation” of chemicals into money, in general. Sometimes I’m lulled into thinking that the chemical industry is about chemistry. It is not. It is always and completely about cash flow.

    Reply

Leave a reply to gaussling Cancel reply