JP2012152163A - セルロース系バイオマスの処理方法、セルロース系バイオマスからの糖又はアルコール又は有機酸の製造方法 - Google Patents
セルロース系バイオマスの処理方法、セルロース系バイオマスからの糖又はアルコール又は有機酸の製造方法 Download PDFInfo
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- JP2012152163A JP2012152163A JP2011015368A JP2011015368A JP2012152163A JP 2012152163 A JP2012152163 A JP 2012152163A JP 2011015368 A JP2011015368 A JP 2011015368A JP 2011015368 A JP2011015368 A JP 2011015368A JP 2012152163 A JP2012152163 A JP 2012152163A
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- Prior art keywords
- cellulosic biomass
- ionic liquid
- organic acid
- alcohol
- cellulose
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000002028 Biomass Substances 0.000 title claims abstract description 70
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 238000000034 method Methods 0.000 title claims abstract description 27
- 150000007524 organic acids Chemical class 0.000 title claims abstract description 21
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 12
- 239000002608 ionic liquid Substances 0.000 claims abstract description 47
- 239000003513 alkali Substances 0.000 claims abstract description 21
- 108010059892 Cellulase Proteins 0.000 claims abstract description 13
- 229940106157 cellulase Drugs 0.000 claims abstract description 13
- 150000004693 imidazolium salts Chemical class 0.000 claims abstract description 13
- 238000002844 melting Methods 0.000 claims abstract description 13
- 230000008018 melting Effects 0.000 claims abstract description 13
- 229920002678 cellulose Polymers 0.000 abstract description 26
- 239000001913 cellulose Substances 0.000 abstract description 26
- 229920002488 Hemicellulose Polymers 0.000 abstract description 21
- 230000002040 relaxant effect Effects 0.000 abstract 2
- -1 forest land residue Substances 0.000 description 38
- 239000000243 solution Substances 0.000 description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 108090000790 Enzymes Proteins 0.000 description 10
- 102000004190 Enzymes Human genes 0.000 description 10
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- 229940088598 enzyme Drugs 0.000 description 10
- 239000008103 glucose Substances 0.000 description 10
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
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- 150000001450 anions Chemical class 0.000 description 5
- 150000001720 carbohydrates Chemical class 0.000 description 5
- 150000004676 glycans Chemical class 0.000 description 5
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- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000001449 anionic compounds Chemical class 0.000 description 4
- 229910001412 inorganic anion Inorganic materials 0.000 description 4
- 150000002891 organic anions Chemical class 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
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- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 3
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- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
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- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 description 2
- REACWASHYHDPSQ-UHFFFAOYSA-N 1-butylpyridin-1-ium Chemical class CCCC[N+]1=CC=CC=C1 REACWASHYHDPSQ-UHFFFAOYSA-N 0.000 description 2
- BMQZYMYBQZGEEY-UHFFFAOYSA-M 1-ethyl-3-methylimidazolium chloride Chemical compound [Cl-].CCN1C=C[N+](C)=C1 BMQZYMYBQZGEEY-UHFFFAOYSA-M 0.000 description 2
- OIDIRWZVUWCCCO-UHFFFAOYSA-N 1-ethylpyridin-1-ium Chemical class CC[N+]1=CC=CC=C1 OIDIRWZVUWCCCO-UHFFFAOYSA-N 0.000 description 2
- AMKUSFIBHAUBIJ-UHFFFAOYSA-N 1-hexylpyridin-1-ium Chemical class CCCCCC[N+]1=CC=CC=C1 AMKUSFIBHAUBIJ-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 description 2
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical compound OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 229910016467 AlCl 4 Inorganic materials 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241000228245 Aspergillus niger Species 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 108010084185 Cellulases Proteins 0.000 description 2
- 102000005575 Cellulases Human genes 0.000 description 2
- 229920003043 Cellulose fiber Polymers 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- 244000166124 Eucalyptus globulus Species 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 241000499912 Trichoderma reesei Species 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
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- 238000010586 diagram Methods 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229920005610 lignin Polymers 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000003672 processing method Methods 0.000 description 2
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
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- 239000011734 sodium Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 1
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 description 1
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Abstract
【解決手段】セルロース系バイオマスをイオン液体、アルカリおよび融点が100℃以上のイミダゾリウム塩を含む溶液に浸漬する工程により、セルロース及び/又はヘミセルロースをイオン液体により十分に緩和する工程、処理後のセルロース系バイオマスにセルラーゼを作用させて糖を得る工程と、得られた糖成分を発酵することでアルコール又は有機酸を得る工程とを含む、アルコール又は有機酸の製造方法。
【選択図】図1
Description
本発明に係るセルロース系バイオマスの処理方法は、セルロース系バイオマスをイオン液体及びアルカリを含む溶液に浸漬する工程を含む。
本発明における、セルロース系バイオマスとは、セルロース繊維の結晶構造とヘミセルロース及びリグニンとの複合体を含むバイオマスを意味する。特に、セルロース繊維の結晶構造及びヘミセルロースをセルロース系バイオマスに含まれる多糖類として扱う。セルロース系バイオマスには、間伐材、建築廃材、産業廃棄物、生活廃棄物、農産廃棄物、製材廃材及び林地残材及び古紙等の廃棄物が含まれる。また、セルロース系バイオマスとしては、段ボール、古紙、古新聞、雑誌、パルプ及びパルプスラッジ等も含む。さらに、セルロース系バイオマスとしては、おが屑や鉋屑等の製材廃材、林地残材又は古紙等を粉砕、圧縮し、成型したペレットをも含む。セルロース系バイオマスは、いかなる形状で使用しても良いが、イオン液体が作用しやすくなることにより、セルロース系バイオマスに含まれるセルロース及び/又はヘミセルロースといった多糖類の緩和が促進されるので、微細化して使用することが好ましい。
アルカリとは、水に溶解して塩基性を示す物質を総称する意味である。すなわち、本発明において、アルカリとしては、特に限定されず、アルカリ金属又はアルカリ土類金属の水酸化物(塩)を挙げることができる。混合液に含まれるアルカリとしては、KOH、K2CO3、NaOH、Na2CO3等のカリウムやナトリウムを含むアルカリ性化合物及びアンモニアを挙げることができる。
セルロース系バイオマスを低分子化させるのに適用可能なイオン液体としては、特に限定されず、イミダゾリウム系イオン液体、ピリジン系イオン液体、脂環族アミン系イオン液体及び脂肪族アミン系イオン液体を使用することができる。これらイオン液体として使用する化合物としては、セルロース系バイオマスに含まれるセルロース及び/又はヘミセルロースの低分子化度を考慮して適宜選択することができる。セルロース及び/又はヘミセルロースの低分子化度という観点からは、イミダゾリウム化合物から構成されるイミダゾリウム系イオン液体を使用することが好ましい。特に、イミダゾリウム化合物としては、1,3−ジアルキルイミダゾリウム塩を使用することがより好ましい。1,3−ジアルキルイミダゾリウム塩のなかでも、1−エチル−3−メチルイミダゾリウムクロライドを使用することが最も好ましい。
また、イオン液体とアルカリとを含有する溶液は、上述したイオン液体以外に、「融点が100℃以上のイミダゾリウム塩」を含有しても良い。「融点が100℃以上のイミダゾリウム塩」とは、イミダゾール環を有するカチオンとアニオンから構成される塩であって、融点が100℃以上であり、イオン液体ではないものを意味する。
なお、セルロース系バイオマスを上述した溶液で処理するとは、当該セルロース系バイオマスを上記溶液に浸漬する処理でも良いし、当該セルロース系バイオマスが上記溶液に浸漬した状態で必要に応じて、攪拌、超音波照射及びボルテックスなどを行ってもよい。
糖化工程とは、酵素処理による糖化によって、セルロースはグルコースなどの単糖に加水分解され、ヘミセルロースはキシロース、アラビノース、マンノースなどの単糖に加水分解される工程を意味する。酵素処理に用いる酵素は、セルロースやヘミセルロースを加水分解できる、セルラーゼ、ヘミセルラーゼ(キシラーゼ、アラビナーゼ、マンナナーゼ)など、従来公知の酵素を適宜使用する。また、酵素は、化学的に合成されたもの又は微生物の生産物を精製したものを混合するのでも良いし、目的酵素を合成する微生物を混合するのでも良い。
上記の糖化工程で得られた糖成分を利用したいわゆる発酵によって、アルコールや有機酸を製造することができる。アルコールとしては、エタノール、プロパノール、ブタノール及びグリセリン等を、有機酸としては、乳酸、酢酸、クエン酸、蓚酸、コハク酸、β−ヒドロキシ酪酸及び3−ヒドロキシプロピオン酸等を製造することができる。
本実施例では、イオン液体として1−ブチル−3−メチルイミダゾリウムアセテート(以下、[Bmim][Ac]と称す)(Solbionic社)を使用した。このイオン液体の構造式を以下に示す。
本実施例では、セルロース系バイオマスとしてカッターミルで破砕処理された平均粒径150mmのユーカリ粉末を使用した。本実施例では、上述のように調整した溶液に、50mgのユーカリ粉末を加えた。その後、セルロース系バイオマスを溶液に浸漬した状態を120℃にて30分間、静置条件下で保持した。処理後、9mlの滅菌水にて洗浄し、その後フィルターを利用してセルロース系バイオマスを滅菌水で数回洗浄して処理溶液を洗い流した。
滅菌水で洗浄した処理後のセルロース系バイオマスを再びバイアル瓶に採取し、これに10mMクエン酸緩衝液(pH5.5)を9.9mL添加し、次いでセルラーゼ混合溶液0.1mLを添加した。この試料を40℃に維持して糖化反応させた。72時間後にサンプリングして、溶液中のグルコース濃度を測定した。
本実施例では、セルロース系バイオマスを浸漬するための溶液に「融点が100℃以上のイミダゾリウム塩」として1,3−ビス(2,6−ジイソプロピルフェニル)イミダゾリウムクロリドを1mg添加した以外は、実施例1と同様にしてセルロース系バイオマスを処理し、その後、糖化処理を行った。1,3−ビス(2,6−ジイソプロピルフェニル)イミダゾリウムクロリドの構造式を以下に示す。
Claims (5)
- セルロース系バイオマスを、イオン液体及びアルカリを含む溶液に浸漬する工程を有するセルロース系バイオマスの処理方法。
- 上記溶液は、融点が100℃以上のイミダゾリウム塩を更に含むことを特徴とする請求項1記載のセルロース系バイオマスの処理方法。
- 請求項1又は2記載の処理方法を適用してセルロース系バイオマスをイオン液体及びアルカリを含む溶液に浸漬する工程と、
処理後のセルロース系バイオマスにセルラーゼを作用させて糖を得る工程とを含む、セルロース系バイオマスからの糖の製造方法。 - 請求項1又は2記載の処理方法を適用してセルロース系バイオマスをイオン液体及びアルカリを含む溶液に浸漬する工程と、
処理後のセルロース系バイオマスにセルラーゼを作用させて糖を得る工程と、
得られた糖成分を発酵することでアルコール又は有機酸を得る工程とを含む、アルコール又は有機酸の製造方法。 - 上記糖を得る工程と上記アルコール又は有機酸を得る工程は、同時に実施されることを特徴とする請求項4記載のアルコール又は有機酸の製造方法。
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EP12739282.7A EP2669382A4 (en) | 2011-01-27 | 2012-01-19 | Cellulosic biomass treatment method, method of producing sugar, alcohol or organic acid from cellulosic biomass |
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US10208076B2 (en) | 2012-12-07 | 2019-02-19 | National Technology & Engineering Solutions Of Sandia, Llc | Renewable aromatics from lignocellulosic lignin |
WO2014089574A1 (en) * | 2012-12-07 | 2014-06-12 | Sandia Corporation | Renewable aromatics from lignocellulosic lignin |
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JP5589871B2 (ja) | 2014-09-17 |
EP2669382A4 (en) | 2017-03-01 |
US20130302854A1 (en) | 2013-11-14 |
WO2012102175A1 (ja) | 2012-08-02 |
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