JP7261011B2 - ワックスエステル誘導体の触媒的製造の方法および系 - Google Patents
ワックスエステル誘導体の触媒的製造の方法および系 Download PDFInfo
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- C—CHEMISTRY; METALLURGY
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Description
1.技術分野
本文献の態様は、一般に、ワックスエステルおよびワックスエステル誘導体を反応させ、処理する系および方法に関する。
本文献は、2016年8月31日に作成され、SequenceListing002_ST25.txtと命名され、2015年1月13日に出願された5895バイトのサイズのASCIIテキスト形式の配列表ファイル中の材料を含有し、参照により全体として本明細書に組み込む。
ワックスエステルは、2つの炭素鎖を結合させるエステル基の形成をもたらす脂肪酸および脂肪族アルコールの化学反応から形成される。ワックスエステルは、種々の動物および植物、例として、ホホバ植物(Simmondsia chinensis)中に見出される。ワックスエステルは、種々の用途、例として、化粧品およびパーソナルケア製品において使用される。
本開示、その態様および実施態様は、本明細書に開示される規定の構成成分にも、組立手順にも、方法要素にも限定されるものではない。ワックスエステルをエステル交換する目的の方法および系と整合する当技術分野において公知の多くの追加の構成成分、組立手順および/または方法要素は、本開示から特定の実施態様による使用について明らかである。したがって、例えば、特定の実施態様が開示されるが、そのような実施態様および実施構成成分は、ワックスエステルをエステル交換するそのような方法および系についての技術分野において公知の任意の形状、サイズ、形式、型、モデル、バージョン、計測、濃度、材料、品質、方法要素、ステップなど、および目的の操作および方法と整合する他の実施構成成分および方法を含み得る。
化学触媒バッチプロセス対酵素触媒バッチプロセス
撹拌羽根を備える1リットルの3首ガラスフラスコに、800gの精製ホホバ油を装入した。油を110Cに加熱し、真空下で30分間乾燥させた。乾燥を完了させた後、少量のナトリウムメチレート(0.3重量%)を混合物に添加した。エステル交換反応物を真空下で120Cにおいて2時間撹拌した。次いで、触媒を1gのクエン酸により中和し、次いでシリカおよび漂白粘土混合物により処理して反応により誘導された着色および他の残留不純物を除去した。エステル交換産物は、黄色液体であった。
リパーゼを使用する連続流酵素触媒エステル交換
10cm×100cmステンレス鋼シリンダに、基材上に固定化された0.5kgのLIPOZYME TL IMを充填した。シリンダの両端部上にメッシュスクリーニング材料を備えて酵素基材を確保し、密封し、酵素製造プロセスにおいて使用される過剰の水分および塩を触媒から排出することにより調整した。シリンダを計量ポンプに接続し、シリンダへの入口における圧力が15psiを超えて上昇すると流動を自動的に閉鎖するソレノイドにより圧力ゲージをモニタリングした。流速は、同一の酵素触媒を使用するバッチ反応から得られる転化の率により計算し、0.8kg/時間であった。シリンダを水バッチ中で浸水させて反応器温度を一定に保持しながら、精製ホホバ油の原液を反応器シリンダに一定温度および圧力において供給した。シリンダを流出する得られた産物は、室温においてわずかに黄色の液体であった。産生されたエステル交換産物の特性を表6にまとめる。
ホホバ油および水添ホホバ油を使用する連続酵素触媒エステル交換
実施例2と同一の実験系を使用したが、70Cにおいて操作して原料中の反応器に流入するホホバ油および水添ホホバ油の均一な原料混合物を維持するように改変した。構造、使用に関する、および水添ホホバワックスエステルを使用するエステル交換反応の種々の追加の背景情報は、James Brown and Robert Kleiman “Trans Isomers in Cosmetics”,Parts 1 and 2,Soap & Cosmetics,May 2001,p.33-36 and June 2001、ならびにSessaら、“Differential Scanning Calorimetry Index for Estimating Level of Saturation in Transeesterified Wax Esters,”J.Amer.Oil Chem. Soc.,v.73,271-273 (1996)、およびDavid J.Sessa,“Derivation of a Cocoa Butter Equivalent from Jojoba Transesterified Ester via a Differential Scanning Calorimetry Index,”J.Sci.Food Agric.,v.72,p.295-298 (1996)(それらの全ての開示は、参照により全体として本明細書に組み込まれる)による論文に見出すことができる。
%転化HJW0=(%C42:2)/41.28×100
として計算することができる。
%転化=(%モノ不飽和物)/(理想%モノ不飽和物)×100
反応前および後にアルコールを添加するバッチ酵素エステル交換
アルコールを用いる酵素触媒バッチプロセスを使用する精製ホホバ油および水添ホホバ油のエステル交換を含む一連の実験を実行した。触媒は、固定化リパーゼ触媒、例えば、本文献に開示のものであった。反応開始前、または反応終了後のいずれかでアルコールを原料材料に添加した。使用される原料のある構成成分は水添ホホバ油を有さない産物(HJW0)であり、原料の他の構成成分は添加された20%の水添ホホバ油を有する産物(HJW20)であった。試験アルコールは、デカノール、オレイルアルコール、ベヘニルアルコールを含んだ。表10は、実験実行の符号を詳述する。
Claims (6)
- ワックスエステルをエステル交換する方法であって、
ワックスエステルを含む原料を提供すること;
前記原料中に、1~34個の炭素の範囲の炭素数を有するアルコールであって、総濃度が前記原料の重量基準で0.01%~2.5%であり、直鎖アルコール、分枝鎖アルコール、直鎖アルコールの任意の組合せ、分枝鎖アルコールの任意の組合せ、およびそれらの任意の組合せからなる群から選択されるアルコールを導入すること;
前記原料をリパーゼと接触させること;
前記原料中の前記ワックスエステルを前記リパーゼにより触媒的にエステル交換して酵素エステル交換産物を形成すること;
を含む、方法。 - 前記アルコールが、完全飽和アルコール、モノ不飽和アルコール、ポリ不飽和アルコール、およびそれらの任意の組合せからなる群から選択される、請求項1に記載の方法。
- 前記原料が、抗酸化物質をさらに含み、前記原料中の前記ワックスエステルを前記リパーゼにより触媒的にエステル交換することが、前記原料中の前記抗酸化物質を除去または分解せずに触媒的にエステル交換することをさらに含む、請求項1に記載の方法。
- 前記原料の前記ワックスエステルが、ホホバワックスエステルである、請求項1に記載の方法。
- 前記ホホバワックスエステルが、水添ホホバワックスエステルをさらに含む、請求項4に記載の方法。
- 前記アルコールが、オレイルアルコールである、請求項1に記載の方法。
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JP2013520985A (ja) | 2010-03-01 | 2013-06-10 | トランスバイオディーゼル リミテッド | 脂肪酸アルキルエステルの酵素的合成のためのプロセス |
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US4360387A (en) | 1980-08-15 | 1982-11-23 | Jojoba Growers & Processors Inc. | Isomorphous jojoba oil compositions containing trans-isomerized jojoba oil |
US4329298A (en) | 1980-08-15 | 1982-05-11 | Jojoba Growers & Processors Inc. | Isomerization of jojoba oil and products thereof |
WO1990015127A1 (en) * | 1989-06-09 | 1990-12-13 | Ag-Seed Pty Limited | Artificial jojoba oil |
JP2796925B2 (ja) * | 1993-09-17 | 1998-09-10 | 日清製油株式会社 | リパーゼによるエステル交換法 |
KR20090121298A (ko) * | 2007-02-02 | 2009-11-25 | 달리아다 미트 피티와이 엘티디 | 바이오디젤 제품 |
US10000731B2 (en) * | 2010-03-01 | 2018-06-19 | Trans Bio-Diesel Ltd. | Enzymatic transesterification/esterification processes employing lipases immobilized on hydrophobic resins in the presence of water solutions |
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WO2012130961A1 (en) | 2011-03-30 | 2012-10-04 | Novozymes A/S | Esterification process |
US11248245B2 (en) * | 2014-12-19 | 2022-02-15 | International Flora Technologies, Ltd. | Processes and systems for catalytic manufacture of wax ester derivatives |
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