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GREEN CHEMICALS
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ADIPIC ACID DORIS DE GUZMAN NEW YORK


Bio-adipic acid prepares for entry
Rennovia and Verdezyne plan to commercialize renewable-based adipic acid by 2014


Amid tightening supply and rising           Rennovia’s preliminary cost es-                                                       “We intend to do the semi-
prices for global adipic acid (ADA),     timates for the method is below the                                                   work and commercial-scale facili-
US start-up firms Rennovia and            cash cost of the cyclohexane proc-                                                    ties with a partner. We are already
Verdezyne see a good chance to           ess operating when crude oil is at                                                    engaged with people from the
enter the sector with their renewa-      $60/bbl (€46/bbl), said president                                                     value chain, coming from both
ble-based ADA versions.                  and CEO Robert Wedinger, who                                                          upstream feedstock suppliers and
   Menlo Park, California-based          spoke at the Bio-based Chemicals                                                      downstream consumer manufac-
Rennovia, US, which was founded          East conference in Boston, Massa-                                                     turers,” he noted.
in 2009, intends to start up its pilot   chusetts, US this month.                                                                 Verdezyne, based in Carlsbad,
scale bio-ADA production in De-             The company’s strategy is to use                                                   California, US, has also been
cember, a year after it initiated re-    chemo-catalytic processing. “Not                                                      working with its bio-ADA for a
search and development (R&D) for         only can we leverage existing                                                         year and aims to scale up from
the glucose-derived chemical.            chemical manufacturing assets                                                         laboratory to pilot production next
   Unlike ADA produced from              using catalytic chemical processes,                                                   year. The company produces ADA
cyclohexane feedstock, Renno-            we also have greater efficiency and                                                    via fermentation processing using
via’s product uses glucose, which        scalability compared to fermenta-         “Our big advantage                          sugar, plant-based oils or paraffin
is converted into glucaric acid as       tion processing,” said Wedinger.                                                      as feedstock.
an intermediate via oxidation            “High space-time yields, tempera-
                                                                                   here is eliminating                            According to Damien Per-
with a catalyst. The glucaric acid       ture and solvent flexibility, high         numerous steps”                             riman, Verdezyne’s vice president
is converted into adipic acid via        carbon efficiencies and low cost of        DAMIEN PERRIMAN                             of business development, the
the hydrogenation process. It pro-       product isolation make chemo-             Vice president, business                    company is looking for a partner
                                                                                   development, Verdezyne
duces water as a by-product.             catalysis preferable to fermentation                                                  for the pilot facility. Commercial-
                                         for many large-volume chemical                                                        ization is expected in 2014–2015.
                                         manufacturing processes.”                                                             Perriman also spoke at the Bio-
   GREEN CHEMICALS                          Using its high-throughput cata-           Rennovia plans to diversify to           based Chemicals East event.
   IN BRIEF                              lyst R&D infrastructure, Rennovia         non-food-based raw materials,                  “Our goal is to license the use of
                                         said it could produce gram quanti-        such as lignocellulosics, as soon           our microorganisms and the
   FORD TO INCREASE
   TWO DECK HEADING                      ties of ADA from glucose within           as these supply chains mature.              processing technology for making
   WHEAT-STRAW PP USE
   TWO DECK HEADING                      three months of initiating the                                                        [ADA] to interested parties or part-
   US car manufacturer Ford Motor
   50 words for a NIB. 275 words         project. The firm intends to use ex-       CAPACITIES COMING SOON                      ners,” said Perriman. “[ADA] is
   is a full column of of US plas-
   forincreasing its useNIBs includ-     isting infrastructure for its feedstock   Rennovia plans to scale up its              such an enormous market and we
   tics compounding firm A.
   ing headline                          supply, including tapping into the        bio-ADA manufacturing to a                  feel that licensing our process is
   Schulman’s wheat straw-based          oversupplied high-fructose corn           demonstration facility late next            the best way to reach the entire
   polypropylene (PP) for injection      syrup (HFCS) capacity.                    year to early 2012, and to com-             market in a faster manner.”
   molding materials. Replacing             US demand for HFCS has fallen          mercial production by late-2013                Depending on feedstock used,
   glass fiber, mica and talc as fill-   by 2.3bn lb (1m tonnes) since 2002,       to early-2014.                              Verdezyne estimated its process-
   ers in PP composites could re-        said Wedinger. “We believe                   The capacity of the commer-              ing to have a 20–30% cost advan-
   duce costs by up to 10%, while        there are opportunities to shift corn     cial plant is expected to be be-            tage in the long run over petro-
   replacing acrylonitrile-butadiene-    wet mill capacity from HFCS pro-          tween 300m–500m lb/year,                    chemical-based ADA. Its process
   styrene (ABS) with wheat straw-       duction to renewable chemicals            which is the typical production             will be cost-neutral if petroleum
   based PP could cut costs by           production without threatening            capacity of petroleum-based ADA             oil prices fall as low as $40/bbl,
   10–15%, according to Ford.            food supply.”                             facilities, said Wedinger.                  said Perriman.
                                                                                                                                  “Our big advantage here is elim-
   CATHAY BIOTECH PLANS                   ADA CONTRACT PRICES ARE RISING                                                       inating numerous steps typically
   BIOBUTANOL EXPANSION                                                                                                        seen in making [ADA] from cy-
                                          $/tonne
   Chinese biobutanol producer                                                                                                 clohexane, where each step has
   Cathay Industrial Biotech plans                                                                                             yield losses,” he said. “With fer-
   to build its second n-butanol                                                                                               mentation processing, you’re es-
   facility either in China or the US,                                                                                         sentially converting the raw mate-
   with capacity of around 100,000                                                                                             rial to [ADA] in a single step.”
   tonnes/year. The company ex-                                                                                                   Another advantage, added Per-
   pects to finalize its plans by the                                                                                          riman, is to be able to build
   end of the year. Cathay Biotech                                                                                             smaller-scale fermentation plants
   manufactures corn-based n-bu-                                                                                               for a fraction of the volume risk
   tanol for chemicals application,               S    O     N    D      J   F     M     A     M     J        J   A     S
                                                                                                                               across different regions based on
   mostly for the domestic market.                2009                   2010                                                  the locally available feedstock
                                          SOURCE: ICIS
                                                                                                                               that they can use.

22 | ICIS Chemical Business | September 27-October 3, 2010                                                                                           www.icis.com
European
                                                      petchems at a
                                                      disadvantage
                                                      FEATURE P34              :D8@9LJ@EJJ8;M@JFIPJIM@:J

 GLOBAL ADA PRODUCERS AT A GLANCE

             Rhodia                           Others
              18%                              13%

                                                       BASF                    9ecc_jj[ZJeOekhkjkh[$
                                                       11%
   INVISTA
     20%                                                      Lioyang
                                                           Petrochemical
                                                                 6%
                                                         Hongye
                                                           5%
                                             Bohui
                     Ascend                   5%
                      13% Asahi Kasei        Radici
                              4%              5%
 SOURCE: Verdezyne



   “The scenario here is to have a      counting for 85% of demand in
facility making feedstock choices.      North America, according to US
Smaller-scale facilities provide        consulting firm Nexant . Poly-
less capital risks compared to a        urethanes (PUs) account for 5%
new large-scale chemical plant,”        of demand, followed by ADA es-           M[Wh[_dl[ij_d]_doekhkjkh[$$$
said Perriman.                          ters, at 4%.
                                                                               [nf[h_[dY[ZYedikbjWdji]beXWbcWha[j
ADA ATTRACTION                          “There is now the                          ademb[Z][ZodWc_YZWjWXWi[
Rennovia estimated the global           possibility of creating
ADA market size at 4.8bn lb, with
a growth rate of 3–5%/year. The         100% bio-based nylon
global operating rate for ADA this      from ADA”
year is estimated at 85%, com-          ROBERT WEDINGER
pared with 95% last year, said          President and CEO, Rennovia
Wedinger. Verdezyne also esti-
mated the market at 4.8bn lb last
year, with a growth rate of 4.3%/          Wedinger pointed out the pos-       :FDDI:@8C›JKI8KP›K:?EFCFP
year. It chose ADA because of the       sibility of now being able to cre-
strong consumer market pull in          ate 100% bio-based nylon since
                                                                                KI8EJ8:K@FE›C8C›IEN89CJ
footwear, automobiles and elec-         ADA can also be converted into
tronics, said Perriman.                 adiponitrile (ADN), which can
   “Engineering plastics is an area     then be converted into caprol-
                                                                                :D8@9lj`ejj8[m`jfipJim`Zjf]]i
where new application develop-          actam (capro), the precursor to          jfle[`e[ge[ekX[m`ZkX`cfi[kf
ments are especially looking for        nylon 6.
                                                                                pfliYlj`ejje[j%N`k_j`ogiXZk`Z
more sustainability value, such as         “[ADA] was once largely used
using renewable-based materi-           to produce [ADN] by dehydration           XiXjXZifjj`^_k^cfYXccfZXk`fej
als,” added Perriman.                   of the diamide, but cheaper buta-         ]fZlj[jgZ`]`ZXccpfek_Z_d`ZXc
   The majority of ADA goes into        diene [BD] has kicked out this
the production of nylon 6,6, ac-        route into oblivion. But the price        Xe[icXk[`e[ljki`j#fli`e[ljkip
                                        of [BD] has been going up and the        ogi`eZ[ZfejlckXekjXile`hlcp
 DEMAND IN NORTH                        market has been volatile,” said
 AMERICA, 2009                                                                     hlXc`]`[kfgigXipfliYlj`ejj
                                        Wedinger.
                          Nylon 6,6        ICIS estimated the September                 ]fi]lklifggfikle`k`j%
                            85%         contract price for European ADA
                                        at $1.36–1.40/lb, FD (free deliv-
                                        ered), NWE (northwest Europe).            :D8@9lj`ejj8[m`jfipJim`Zj1
                                        The Asian contract price was at            :[[f?di_]^ji$;nf[hjbo7ffb_[Z$
                                        $1.11–1.15/lb, CFR (cost and
                                        freight), NE (Northeast) Asia.
                                           Rennovia estimated the US
                                        ADA price at $1.25/lb, while Ver-
                                        dezyne noted the spot price had
                                        skyrocketed to around $1.75/lb,
          Polyurethanes                 because of the global shortage of
               5%                       ADA. Reduced operating rates
      Others    Adipate esters                                                 
,
-ÊUÊ
1,*
ÊUÊ-ÊUÊ

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Bioadipic Acid article on ICIS Chemical Business

  • 1. GREEN CHEMICALS Check out our website for the latest news, information and prices on chemicals and commodities at icis.com/pricing ADIPIC ACID DORIS DE GUZMAN NEW YORK Bio-adipic acid prepares for entry Rennovia and Verdezyne plan to commercialize renewable-based adipic acid by 2014 Amid tightening supply and rising Rennovia’s preliminary cost es- “We intend to do the semi- prices for global adipic acid (ADA), timates for the method is below the work and commercial-scale facili- US start-up firms Rennovia and cash cost of the cyclohexane proc- ties with a partner. We are already Verdezyne see a good chance to ess operating when crude oil is at engaged with people from the enter the sector with their renewa- $60/bbl (€46/bbl), said president value chain, coming from both ble-based ADA versions. and CEO Robert Wedinger, who upstream feedstock suppliers and Menlo Park, California-based spoke at the Bio-based Chemicals downstream consumer manufac- Rennovia, US, which was founded East conference in Boston, Massa- turers,” he noted. in 2009, intends to start up its pilot chusetts, US this month. Verdezyne, based in Carlsbad, scale bio-ADA production in De- The company’s strategy is to use California, US, has also been cember, a year after it initiated re- chemo-catalytic processing. “Not working with its bio-ADA for a search and development (R&D) for only can we leverage existing year and aims to scale up from the glucose-derived chemical. chemical manufacturing assets laboratory to pilot production next Unlike ADA produced from using catalytic chemical processes, year. The company produces ADA cyclohexane feedstock, Renno- we also have greater efficiency and via fermentation processing using via’s product uses glucose, which scalability compared to fermenta- “Our big advantage sugar, plant-based oils or paraffin is converted into glucaric acid as tion processing,” said Wedinger. as feedstock. an intermediate via oxidation “High space-time yields, tempera- here is eliminating According to Damien Per- with a catalyst. The glucaric acid ture and solvent flexibility, high numerous steps” riman, Verdezyne’s vice president is converted into adipic acid via carbon efficiencies and low cost of DAMIEN PERRIMAN of business development, the the hydrogenation process. It pro- product isolation make chemo- Vice president, business company is looking for a partner development, Verdezyne duces water as a by-product. catalysis preferable to fermentation for the pilot facility. Commercial- for many large-volume chemical ization is expected in 2014–2015. manufacturing processes.” Perriman also spoke at the Bio- GREEN CHEMICALS Using its high-throughput cata- Rennovia plans to diversify to based Chemicals East event. IN BRIEF lyst R&D infrastructure, Rennovia non-food-based raw materials, “Our goal is to license the use of said it could produce gram quanti- such as lignocellulosics, as soon our microorganisms and the FORD TO INCREASE TWO DECK HEADING ties of ADA from glucose within as these supply chains mature. processing technology for making WHEAT-STRAW PP USE TWO DECK HEADING three months of initiating the [ADA] to interested parties or part- US car manufacturer Ford Motor 50 words for a NIB. 275 words project. The firm intends to use ex- CAPACITIES COMING SOON ners,” said Perriman. “[ADA] is is a full column of of US plas- forincreasing its useNIBs includ- isting infrastructure for its feedstock Rennovia plans to scale up its such an enormous market and we tics compounding firm A. ing headline supply, including tapping into the bio-ADA manufacturing to a feel that licensing our process is Schulman’s wheat straw-based oversupplied high-fructose corn demonstration facility late next the best way to reach the entire polypropylene (PP) for injection syrup (HFCS) capacity. year to early 2012, and to com- market in a faster manner.” molding materials. Replacing US demand for HFCS has fallen mercial production by late-2013 Depending on feedstock used, glass fiber, mica and talc as fill- by 2.3bn lb (1m tonnes) since 2002, to early-2014. Verdezyne estimated its process- ers in PP composites could re- said Wedinger. “We believe The capacity of the commer- ing to have a 20–30% cost advan- duce costs by up to 10%, while there are opportunities to shift corn cial plant is expected to be be- tage in the long run over petro- replacing acrylonitrile-butadiene- wet mill capacity from HFCS pro- tween 300m–500m lb/year, chemical-based ADA. Its process styrene (ABS) with wheat straw- duction to renewable chemicals which is the typical production will be cost-neutral if petroleum based PP could cut costs by production without threatening capacity of petroleum-based ADA oil prices fall as low as $40/bbl, 10–15%, according to Ford. food supply.” facilities, said Wedinger. said Perriman. “Our big advantage here is elim- CATHAY BIOTECH PLANS ADA CONTRACT PRICES ARE RISING inating numerous steps typically BIOBUTANOL EXPANSION seen in making [ADA] from cy- $/tonne Chinese biobutanol producer clohexane, where each step has Cathay Industrial Biotech plans yield losses,” he said. “With fer- to build its second n-butanol mentation processing, you’re es- facility either in China or the US, sentially converting the raw mate- with capacity of around 100,000 rial to [ADA] in a single step.” tonnes/year. The company ex- Another advantage, added Per- pects to finalize its plans by the riman, is to be able to build end of the year. Cathay Biotech smaller-scale fermentation plants manufactures corn-based n-bu- for a fraction of the volume risk tanol for chemicals application, S O N D J F M A M J J A S across different regions based on mostly for the domestic market. 2009 2010 the locally available feedstock SOURCE: ICIS that they can use. 22 | ICIS Chemical Business | September 27-October 3, 2010 www.icis.com
  • 2. European petchems at a disadvantage FEATURE P34 :D8@9LJ@EJJ8;M@JFIPJIM@:J GLOBAL ADA PRODUCERS AT A GLANCE Rhodia Others 18% 13% BASF 9ecc_jj[ZJeOekhkjkh[$ 11% INVISTA 20% Lioyang Petrochemical 6% Hongye 5% Bohui Ascend 5% 13% Asahi Kasei Radici 4% 5% SOURCE: Verdezyne “The scenario here is to have a counting for 85% of demand in facility making feedstock choices. North America, according to US Smaller-scale facilities provide consulting firm Nexant . Poly- less capital risks compared to a urethanes (PUs) account for 5% new large-scale chemical plant,” of demand, followed by ADA es- M[Wh[_dl[ij_d]_doekhkjkh[$$$ said Perriman. ters, at 4%. [nf[h_[dY[ZYedikbjWdji]beXWbcWha[j ADA ATTRACTION “There is now the ademb[Z][ZodWc_YZWjWXWi[ Rennovia estimated the global possibility of creating ADA market size at 4.8bn lb, with a growth rate of 3–5%/year. The 100% bio-based nylon global operating rate for ADA this from ADA” year is estimated at 85%, com- ROBERT WEDINGER pared with 95% last year, said President and CEO, Rennovia Wedinger. Verdezyne also esti- mated the market at 4.8bn lb last year, with a growth rate of 4.3%/ Wedinger pointed out the pos- :FDDI:@8C›JKI8KP›K:?EFCFP year. It chose ADA because of the sibility of now being able to cre- strong consumer market pull in ate 100% bio-based nylon since KI8EJ8:K@FE›C8C›IEN89CJ footwear, automobiles and elec- ADA can also be converted into tronics, said Perriman. adiponitrile (ADN), which can “Engineering plastics is an area then be converted into caprol- :D8@9lj`ejj8[m`jfipJim`Zjf]]i where new application develop- actam (capro), the precursor to jfle[`e[ge[ekX[m`ZkX`cfi[kf ments are especially looking for nylon 6. pfliYlj`ejje[j%N`k_j`ogiXZk`Z more sustainability value, such as “[ADA] was once largely used using renewable-based materi- to produce [ADN] by dehydration XiXjXZifjj`^_k^cfYXccfZXk`fej als,” added Perriman. of the diamide, but cheaper buta- ]fZlj[jgZ`]`ZXccpfek_Z_d`ZXc The majority of ADA goes into diene [BD] has kicked out this the production of nylon 6,6, ac- route into oblivion. But the price Xe[icXk[`e[ljki`j#fli`e[ljkip of [BD] has been going up and the ogi`eZ[ZfejlckXekjXile`hlcp DEMAND IN NORTH market has been volatile,” said AMERICA, 2009 hlXc`]`[kfgigXipfliYlj`ejj Wedinger. Nylon 6,6 ICIS estimated the September ]fi]lklifggfikle`k`j% 85% contract price for European ADA at $1.36–1.40/lb, FD (free deliv- ered), NWE (northwest Europe). :D8@9lj`ejj8[m`jfipJim`Zj1 The Asian contract price was at :[[f?di_]^ji$;nf[hjbo7ffb_[Z$ $1.11–1.15/lb, CFR (cost and freight), NE (Northeast) Asia. Rennovia estimated the US ADA price at $1.25/lb, while Ver- dezyne noted the spot price had skyrocketed to around $1.75/lb, Polyurethanes because of the global shortage of 5% ADA. Reduced operating rates Others Adipate esters , -ÊUÊ 1,* ÊUÊ-ÊUÊ
  • 3.
  • 4. Ê -/ and global capacity reductions last 6% 4% year were the drivers for the tight- SOURCE: Nexant ening market, said Perriman. www.icis.com September 27-October 3, 2010 | ICIS Chemical Business | 23