JPWO2007032188A1 - 固体酸触媒 - Google Patents
固体酸触媒 Download PDFInfo
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- 239000011973 solid acid Substances 0.000 title claims description 32
- 229910003481 amorphous carbon Inorganic materials 0.000 claims abstract description 28
- 125000000542 sulfonic acid group Chemical group 0.000 claims abstract description 13
- 150000002894 organic compounds Chemical class 0.000 claims description 32
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 30
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 30
- 239000000463 material Substances 0.000 claims description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 10
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- 229910052757 nitrogen Inorganic materials 0.000 description 2
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- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
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- 238000006386 neutralization reaction Methods 0.000 description 1
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- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
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- FZYCEURIEDTWNS-UHFFFAOYSA-N prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC=C1.CC(=C)C1=CC=CC=C1 FZYCEURIEDTWNS-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
- B01J31/08—Ion-exchange resins
- B01J31/10—Ion-exchange resins sulfonated
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
即ち、本発明は、以下の(1)〜(8)を提供するものである。
(2)高表面積担体が、50m2g-1以上の比表面積を有することを特徴とする(1)に記載の固体酸触媒。
(3)高表面積担体の材料が、メソポーラス材料であることを特徴とする(1)又は(2)に記載の固体酸触媒。
(4)メソポラース材料が、メソポーラスシリカであることを特徴とする(3)に記載の固体酸触媒。
(5)スルホン酸基が導入された無定形炭素が、0.5mmol/g以上のスルホン酸密度を示し、ラマンスペクトルにおけるDバンドとGバンドの積分強度比が0.1〜0.7を示すことを特徴とする(1)乃至(4)のいずれかに記載の固体酸触媒。
(6)有機化合物を高表面積担体に固定する工程、及び高表面積担体に固定した有機化合物を濃硫酸又は発煙硫酸中で加熱処理する工程を含むことを特徴とする固体酸触媒の製造方法。
(7)有機化合物を高表面積担体に固定する工程と、高表面積担体に固定した有機化合物を濃硫酸又は発煙硫酸中で加熱処理する工程との間に、有機化合物を部分炭化させる工程を含むことを特徴とする(6)に記載の固体酸触媒の製造方法。
(8)有機化合物を高表面積担体に固定する工程を低圧下で行うことを特徴とする(6)又は(7)に記載の固体酸触媒の製造方法。
本発明の固体酸触媒は、高表面積担体と、これに固定されたスルホン酸基導入無定形炭素とからなるものである。本発明の固体酸触媒は、高表面積担体とスルホン酸基導入無定形炭素のみからなってもよいが、他の要素を含んでいてもよい。
Gバンドは、炭素六員環のE2g modeの振動であり、そのピークトップは1580cm-1〜±5cm-1に現れる。
両者のピークの和からなるラマンスペクトルをガウシアン、あるいはガウシアン−ローレンツイアンで2つにピーク分割し、得られたDバンド、Gバンドの積分強度をそれぞれの積分強度とした。
〔実施例〕
メソポーラスシリカSBA−15(J. Am. Chem. Soc. 122, 10712(2000):比表面積1020 m2 g-1)1gに、水2gにD−グルコース1.25gと濃硫酸(90%以上)0.14gを溶解した水溶液をしみこませ、100℃24時間乾燥した後、550℃3時間、窒素気流中で加熱することにより、部分炭化した。これを濃硫酸中で150℃10時間加熱してから、80℃以上の蒸留水で繰り返し洗浄することによってスルホン酸基導入無定形炭素−高表面積担体複合体を得た。この複合体の比表面積は610 m2 g-1であり、その重量の38%はスルホン酸基導入無定形炭素であることが粉末X線回折、炭素の燃焼による重量変化によって確認された。この複合体におけるスルホン酸基導入無定形炭素1gあたり、0.95mmolのスルホン酸基を有することが確認された。また、このスルホン酸基導入無定形炭素のラマンスペクトルにおけるDバンドとGバンドの積分強度比(I(D)/I(G))は0.68であった。
D-グルコース20gを窒素ガス流通下、400℃15時間加熱することによって炭素質粉末を得た。この粉末を200mlの15wt%発煙硫酸中で撹拌しながら150℃で15時間加熱し、黒色粉末を得た。これを繰り返し蒸留水で洗浄することにより、材料中の硫酸を除去し、スルホン酸基導入無定形炭素を得た。
25mmolのα-メチルスチレンを溶解したクメン(溶媒)25mlにナフィオンNR50(スルホン酸密度:0.9mmol/g)0.2gを加え、50℃で1時間反応させた後、生成物をガスクロマトグラフで定量した。その結果、目的生成物である不飽和二量体の生成量は0.1 mmolに過ぎず、その選択率も40%であることが確認された。
25mmolのα-メチルスチレンを溶解したクメン(溶媒)25mlにナフィオンSAC13(高表面積シリカに担持したナフィオン、スルホン酸密度:0.3mmol/g)0.2gを加え、50℃で1時間反応させた後、生成物をガスクロマトグラフで定量した。その結果、目的生成物である不飽和二量体の生成量は4.4 mmolに過ぎず、その選択率も40%に過ぎないことが確認された。
Claims (8)
- 高表面積担体と、これに固定されたスルホン酸基が導入された無定形炭素とからなる固体酸触媒。
- 高表面積担体が、50m2g-1以上の比表面積を有することを特徴とする請求項1に記載の固体酸触媒。
- 高表面積担体の材料が、メソポーラス材料であることを特徴とする請求項1又は2に記載の固体酸触媒。
- メソポラース材料が、メソポーラスシリカであることを特徴とする請求項3に記載の固体酸触媒。
- スルホン酸基が導入された無定形炭素が、0.5mmol/g以上のスルホン酸密度を示し、ラマンスペクトルにおけるDバンドとGバンドの積分強度比が0.1〜0.7を示すことを特徴とする請求項1乃至4のいずれか一項に記載の固体酸触媒。
- 有機化合物を高表面積担体に固定する工程、及び高表面積担体に固定した有機化合物を濃硫酸又は発煙硫酸中で加熱処理する工程を含むことを特徴とする固体酸触媒の製造方法。
- 有機化合物を高表面積担体に固定する工程と、高表面積担体に固定した有機化合物を濃硫酸又は発煙硫酸中で加熱処理する工程との間に、有機化合物を部分炭化させる工程を含むことを特徴とする請求項6に記載の固体酸触媒の製造方法。
- 有機化合物を高表面積担体に固定する工程を低圧下で行うことを特徴とする請求項6又は7に記載の固体酸触媒の製造方法。
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US71736805P | 2005-09-16 | 2005-09-16 | |
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PCT/JP2006/316558 WO2007032188A1 (ja) | 2005-09-16 | 2006-08-24 | 固体酸触媒 |
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WO2008123530A1 (ja) * | 2007-03-27 | 2008-10-16 | Nippon Oil Corporation | スルホン酸基含有炭素質材料からなる固体酸触媒の製造方法およびその用途 |
JP5528036B2 (ja) * | 2008-09-12 | 2014-06-25 | 公益財団法人神奈川科学技術アカデミー | 炭素系固体酸及びその製造方法 |
JP2012005382A (ja) * | 2010-06-23 | 2012-01-12 | Equos Research Co Ltd | バイオマス加水分解反応装置 |
CN102500415A (zh) * | 2011-12-02 | 2012-06-20 | 南开大学 | 由纤维素制备的碳微球催化剂及其应用 |
CN103285883A (zh) * | 2013-06-28 | 2013-09-11 | 黑龙江大学 | 一种碳基磺酸固体酸催化剂的制备方法 |
CN103934027B (zh) * | 2014-04-24 | 2015-12-30 | 南京德灿化学有限公司 | 一种固体酸催化剂及其制备方法和应用 |
JP7038991B2 (ja) * | 2017-07-31 | 2022-03-22 | 学校法人 芝浦工業大学 | 酸基含有アモルファスカーボンの製造方法 |
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JPS6035088A (ja) * | 1983-08-06 | 1985-02-22 | Fuji Sekiyu Kk | 各種炭素源のスルホン化方法 |
JPH11135109A (ja) * | 1997-10-28 | 1999-05-21 | Mitsui Mining Co Ltd | リチウムイオン二次電池負極用非晶質炭素材、及びその製造方法 |
JP3113912B2 (ja) * | 1999-04-30 | 2000-12-04 | 工業技術院長 | 芳香族炭化水素又は芳香族炭化水素を含む炭化水素に含まれる芳香族炭化水素の水素化異性化処理方法及びその水素化異性化処理方法に使用される触媒 |
JP4041409B2 (ja) * | 2003-02-05 | 2008-01-30 | 独立行政法人科学技術振興機構 | 多環式芳香族炭素系固体強酸 |
US8709273B2 (en) * | 2003-09-16 | 2014-04-29 | Tokyo Institute Of Technology | Sulfonated amorphous carbon, process for producing the same and use thereof |
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