Change Happens Slowly For Years, Then It's Sudden

Biobased Hexamethylenediamine

Hey there, welcome to the 46 new people that have signed up to get these emails since the start of the year. This is an on-going experiment of mine where I attempt to stay up to date on the news going on in the chemical industry and I write about it. I try to cover the broad value chain of the chemical industry from oil and gas all the way to specialty chemicals. I’ve significantly changed how I’ve written the newsletter this year and it's a bit more focused on singular topics every time I hit “publish.” 

I’m still trying to maintain my thematic schedule of writing about chemistry careers, oil and gas, product development, green chemistry, specialty chemicals, quarterly updates, deep dives into start-ups, and mergers. 

Spending time reading, writing, and thinking about such a broad array of topics helps inform me on where I think the chemical industry is headed and it hopefully helps prepare me for my own future. My own writing here is sometimes more polished and sometimes it is just me organizing my thoughts.

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Change Happens Slowly For Years, Then It's Sudden

Picture by David Blume

Genomatica and Covestro have teamed up to produce biobased hexamethylenediamine. If that chemical name seems complicated to you then all you need to remember is there are six carbons (methylene groups) sandwiched between two amines (nitrogen + 2 hydrogens bonded to a carbon). Hexamethylene diamine is a commodity chemical that is used in some niche applications (niche commodity chemical?) such as making nylon and making hexamethylene diisocyanate, which we get by reacting 2 equivalents of phosgene with hexamethylenediamine. Making isocyanates is core to Covestro’s business just like it is for Huntsman.

Hexamethylene diisocyanate is an aliphatic diisocyanate and these types of isocyanates are important for making UV stable polyurethanes which can go into everything from architectural coatings (the paints you use on your houses and commercial buildings) to wood coatings to automotive coatings and adhesives. Other aliphatic diisocyanates include isophorone diisocyanate and H12MDI and various dimers/oligomers. Anytime there is an exterior polyurethane paint or coating think about the aliphatic isocyanates making it happen. 

Apparently, the market for hexamethylenediamine (HDMA) is around 2 million tons per year which is sizable. Genomatica and Covestro expect to be able to make tons during manufacturing campaigns. I suspect this is through a relatively large pilot reactor set-up that the companies have developed while they figure out the business case for the project. I suspect that high oil prices will be favorable in the pricing of this new route to HDMA.

The traditional petrochemical route to hexamethylenediamine I learned about in graduate school was through isolating butane through fractional distillation of crude oil, steam cracking to butadiene, and then reacting with hydrogen cyanide. If this sounds energy intensive and not exactly environmentally friendly then trust your instincts. 

Genomatica has a patent specifically (US20210130861A1) around a genetically engineered microorganism that will produce diamines. To summarize the patent summary Genomatica has developed a microorganism that takes glucose (or other sugars, I’m sure) and turns it into diamines and then utilizes carbon dioxide to neutralize the diamine which enables pH control of the fermentation broth. Too much free diamine in the water would likely lead to death of the microorganism.

It’s hard to know any meaningful titers or production rates of the fermentation for HDMA from Genomatica via their patent. I cannot comment on how efficient the Genomatica fermentation is, but in looking at oil prices we are approaching new highs seemingly every month so eventually I suspect HDMA via fermentation might eventually achieve cost parity provided Genomatica can capture an economy of scale advantages and cheap sugar prices.

One thing I’d like to see would be an lifecycle assessment of Genomatica’s process versus the traditional petrochemical route. Is this process actually more efficient in reducing carbon release to atmosphere or is there some brutally inefficient downstream processing that needs to occur?

Covestro will be waiting to turn this biobased HDMA into an isocyanate and will be able to spin a story of biobased polyurethanes. If success it’s another small step towards an economy not based on crude oil. Small steps like these add up to eventually changing how everyone does business.

Anyone trialing biobased HDMA or hexamethylene diisocyanate in the lab yet and want to talk to me about it? I have a feeling it works just like the stuff from oil.

Tony