INVISTA seeks more bio-based nylon feedstock

Welcome to the new green chemicals blog’s first post!

My interview with INVISTA happened after the company announced its partnership with LanzaTech to develop bio-based butadiene as feedstock for their proprietary adiponitrile (ADN) production technology. ADN is an intermediate chemical used in the manufacture of nylon 6,6.

LanzaTech initially plans to convert carbon monoxide (CO) to 2,3 butanediol (2,3 BDO), and then subsequently convert it to 1,3 butadiene (BD) using gas fermentation. Longer term, the companies plans to produce CO-based BD directly using a single step process via gas fermentation.

LanzaTech and INVISTA plan their bio-BD commercialization using the 2,3 BDO route to BD by 2016.

According to Bill Greenfield, vice president of INVISTA’s nylon intermediates business, the company has been working for several years now in developing their own bio-based chemical development capabilities. The company hired a number of PhDs and research scientists in the field of biogenetics and biochemistry to develop bio-based intermediates and materials for the business.

Bio-butadiene will be the first of INVISTA’s biotechnology-based chemical feedstock although the company has already been marketing nylon materials that has bio-based content including its Antron Bio_Legacy nylon that contains 10% nylon 11 derived from castor oil.

Throughout the years of the blog’s coverage in bio-based polyamides, possible biotechnology-based chemical intermediates that INVISTA COULD be working on for future nylon feedstock includes adipic acid to produce nylon 6,6; cyclododecatriene (where bio-based butadiene as feedstock can be used) to produce nylon 12; cyclohexane from bio-based benzene (remember Virent and Anellotech?) to produce nylon 6.

2,5- furandicarboxylic acid (FDCA), where Avantium is currently working at, can also be used as feedstock towards producing an alternative to nylon 6,6 if FDCA is to be condensed with HMDA(hexamethylenediamine), according to Nexant. HMDA by the way is currently manufactured using ADN.

In Nexant’s prospectus for a bio-polyamides study, nylon 6 and nylon 6,6 (also known as polyamides 6 and polyamides 6,6) are currently the largest volume polyamides. Nylon 6 global demand in 2010 was pegged by Nexant at more than 4m short tons and is expected to grow to almost 6m tons by 2020.

Here are the possible biological routes for producing intermediates towards nylon manufacture, according to Nexant:

BIO-BASED ADIPIC ACID ROUTES:

• Direct fermentation to adipic acid
• Bio-based benzene –> KA Oil –> adipic acid
• Muconic acid –> adipic acid
• Bio-based butadiene –> adipic acid
• Glucaric acid –> adipic acid

BIO-BASED HMDA ROUTES:

• Bio-butadiene –> HMDA
• Bio-butadiene –> ADN–> HMDA
• Bio-acrylonitrile –> ADN –> HMDA
• Bio-adipic acid –> HMDA

BIO-BASED CAPROLACTAM ROUTES:

• Lysine –> caprolactam
• Bio-butadiene –> caprolactam
• Bio-butadiene –> ADN –> caprolactam
• Bio-acrylonitrile –> ADN –> caprolactam
• Bio-benzene –> caprolactam

OTHER BIO-BASED POLYAMIDE MONOMERS ROUTES:

• 1,4-diaminobutane+ bio-adipic acid = PA 4,6
• 9-Aminopelargonic acid = PA 9
• Bio-purified terephthalic acid (PTA) + HMDA = nylon T/6
• FDCA as substitute for PTA in polyamides

According to INVISTA’s Greenfield, the company is also continuously exploring other possible routes including sugar fermentation-based intermediates.

Some of the recent press announcements on bio-based polyamides below:

• Evonik expanding its bio-based VESTAMID Terra polymers
• Rhodia and Avantium developing bio-based polyamides
• Arkema expanded its castor-based polyamides under the RILSAN brand when it acquired Hipro Polymers and Casda Biomaterials