Company initiatives, studies and reports

Bio-acrylic acid on the way

So…I just found out yesterday that my goodbye post on my old blog has been taken down by ICIS. I am not sure how this action is beneficial to them except that it looked really mean-spirited to me but I guess that’s how some corporations work.

Oh well…

So let me start my second post about bio-acrylic acid. BASF, Cargill and Novozymes announced last month that BASF has joined both Cargill and Novozymes in the development and commercialization of bio-based acrylic acid using sugar-based 3-hydroxypropionic acid (3-HP) for feedstock.

I first reported about this project in January 2008 when Cargill and Novozymes announced back then about their collaboration on 3-HP produced from sugar fermentation using bioengineered organisms. The US Department of Energy gave the project a $1.5m funding.

The companies said back then that their bio-acrylic acid could be ready within five years. Five years later, Cargill and Novozymes have pulled in Germany-based chemical firm BASF, which is the world’s largest producer of acrylic acid, according to its press statement.

According to a June 2010 global acrylic acid capacity report from Tecnon OrbiChem (which was published by ICIS), BASF had a total global acrylic acid capacity of 1.14m tonnes/year including the company’s joint venture with Petronas in Kuantan, Malaysia (160,000 tonnes) and with YPC (160,000 tonnes).

The other top producers include Dow Chemical, Arkema, StoHaas Monomer, Nippon Shokubai and Formosa Plastics.

According to BASF, it plans to initially use the bio-based acrylic acid to manufacture superabsorbent polymers (SAP). The press release noted SAP as one of the main applications for acrylic acid. It is mainly used in diapers and other hygienic products.

The annual global market volume of acrylic acid was estimated at the end of 2011 at 4.5m tons with a value of $11bn at a growth rate of 4%/year.

According to a recent interview with Novozymes vice president Rasmus von Gottberg, the companies intend to set up a pilot-scale fermentation for 3-HP to acrylic acid within six months or so as Novozymes and Cargill finalized the development of their strains that can convert glucose to 3-HP. BASF will then contribute their chemical and technology expertise for the conversion of 3-HP to acrylic acid.

Now let’s look at some of the recent developments in bio-based acrylic acid.

In March, OPX Biotechnologies said it was able to successfully demonstrated its fermentation process to produce acrylic acid from sugar-based 3-HP at a 3,000 liter-scale (equivalent to 60,000 lbs/year) in a pilot facility owned by the Michigan Biotechnology Institute (MBI), a non-profit organization owned by Michigan State University (MSU) Foundation.

Early this year, I interviewed OPXBio CEO Chas Eggert on where the company’s at in terms of commercialization milestones. According to Eggert, its partner Dow Chemical is focusing on the use of sugar feedstock and the conversion process of sugar to bio-acrylic acid while OPXBio is focusing on its microbe using its “Efficiency Directed Genome Engineering” (EDGE) platform, as well as developing the 3-HP (hydroxypropionic acid) bioprocess.

OPXBio claims to have a lower-cost bio-based route (and competitive to petroleum-based route) when it comes to producing acrylic acid. In that interview, OPXBio said it was already able to produce a 50 cents/lb bio-acrylic acid using dextrose feedstock at 14 cents/lb, and a 38 cents/lb bio-acrylic acid using sucrose feedstock at 8 cents/lb. At the time of the interview Eggert noted average market selling price of acrylic acid during the interview at $1.20 cents/lb.

Eggert said the company plans to have a second demonstration plant with a capacity of 600,000 lbs/year in 2013. A commercial plant with a capacity of 100m lbs/year is expected by 2015.

Also in March this year, bio-succinic acid producer Myriant said it has filed a patent protection with the US Patent and Trademark Office (USPTO) for its bio-acrylic acid process. Myriant said it will immediately initiate scale-up activities to provide product samples to customers in the second half of 2012.

PHA bioplastic producer Metabolix, during its second quarter earnings call on July 26, noted that it has started shipping sample quantities of dried biomass for conversion to bio-based acrylic acid for customer evaluation. The company said it had a successful scale-up recovery of acrylic acid from dried biomass in Metabolix’s Cambridge, Mass., laboratory in the second quarter this year.

In April this year, Metabolix was awarded US patent 8,114,643 titled “Polyhydroxyalkanoate production from Polyols,” which enables the creation of genetic constructs to make 3-HP in microbial and crop plant systems.  The patent also describes the use of glycerol and sugars as alternative feedstock.

Genomatica also has several patents involving production of bio-based acrylic acid using sugar-based fumaric acid via methathesis transformation (with a sufficient amount of ethylene).

In 2010, Arkema’s CRDE (Cetre de Recherche et de Developpement de l’Est) R&D Center in Carling, France, started collaborating with the Lorraine Regional Council to develop an industrial process for the synthesis of vegetable oil-based glycerol into acrylic acid. The EUR11m program will span over three years. The program is in conjunction with two university laboratories — ENSIC Chemical Engineering School and Paul Verlaine University.

According to a June 2011 ICB article written by colleague Clay Boswell, Arkema’s interest in glycerol stems from both its position in acrylic acid and its role as supplier of methyl mercaptopropionaldehyde (MMP), which is used to produce the amino acid methionine. Both MMP and acrylic acid can be made from the same intermediate, acrolein, which itself is accessible by the catalytic dehydration of glycerol.

Arkema said its process is well developed, running at pilot scale and producing several kilograms of acrylic acid per day. The company has already been testing several applications in house and a commercial plant is expected within the next 4-5 years.

In 2009, Japan’s Nippon Shokubai said it has developed a high-performance catalyst for manufacturing acrolein – the intermediate at manufacturing acrylic acid – by gas phase dehydration. According to the press release, a pilot plant will supposedly be constructed in the first quarter of 2011 at Nippon’s site in Himeji, Japan.

I’m still looking for any recent news on Nippon Shokubai’s project…

According to Nexant’s December 2011 bio-acrylic acid prospectus, Nippon Kayaku, Rohm and Haas (now integrated within Dow Chemical), Evonik Stockhausen and Showa Denko have also been granted patents for the production of acrolein and acrylic acid from the dehydration of glycerol.

Another interesting developments is the conversion of carbon monoxide or carbon dioxide to acrylic acid. Novomer is combining ethylene oxide and carbon monoxide using its proprietary catalyst to form an intermediate called propiolactone. The propiolactone is then converted to either glacial acrylic acid or acrylate esters.

In November 2010, BASF announced that the Federal Ministry of Education and Research (BMBF) in Germany pledged EUR 2.2m for a project by BASF-supported Catalysis Research Laboratory (CaRLa) and hteAG, where BASF has a majority interest, to develop production of sodium acrylate using carbon dioxide and ethene.

About Doris de Guzman

Will Green Chemistry save the world or is it hype? Doris de Guzman examines alternative processing, new technology, R&D and other sustainability initiatives aimed at preventing pollution; replacing ingredients; and using renewable feedstocks in Green Chemistry. She has been covering the oleochemicals market for 15 years and spread her beat to inorganics, biofuels and green chemistry.

Discussion

7 Responses to “Bio-acrylic acid on the way”

  1. Hi I am student of chemical engineering of Argentina. I am very interested in the production of bio-acrylic acid, in fact I am conducting a thesis on their production. I would like to communicate with you to pass on concerns and if possible to obtain information about the production process of the acid.

    thank you very much and apologize for the inconvenience.

    lucas.volmaro @ gmail.com

    Posted by Lucas | June 1, 2014, 11:45 am
  2. I sent you an email.

    Posted by Doris de Guzman | June 3, 2014, 11:14 am
  3. Hi Ms Doris,

    I’m a chemical engineering student from Malaysia and currently doing a design project on the production of acrylic acid from crude glycerol. I would like to know more information regarding the process as it would be a great help for me.

    Hope to hear from you soon. Tq

    Posted by Shazleen | September 26, 2014, 2:09 am
    • Hi Shazleen,
      I believe there is no commercial process yet on producing acrylic acid from glycerol. You might want to contact France-based Arkema or Japan-based Nippon Shokubai for this technology. They have a patent on this.

      Posted by Doris de Guzman | October 14, 2014, 10:46 am
  4. Hi Ms Doris,

    I am a postdoc. working at University of florida. I have using acrolein as starting material for my experiment. Do you have any idea which company has commercialized bio-acrolein?

    Thanks

    Fei

    Posted by Fei Wang | October 30, 2014, 10:29 pm
    • Hi Fei,
      I am not actually sure who are selling these if there are any. Hopefully somebody will respond to your inquiry out there. Sorry I can’t be of help.

      Best Regards,
      Doris

      Posted by Doris de Guzman | November 17, 2014, 7:13 am
  5. HI Mrs Doris
    I am Smaeel from Iran
    I want install an plan for production of AA from propane as soon as
    do you think which way are better? my way or your way?
    reason?
    thanks
    My email: sapoly2013@gmail.com

    Posted by Smaeel | August 15, 2016, 8:44 am

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