JP6040933B2 - p−キシレン及び/又はp−トルアルデヒドの製造方法 - Google Patents
p−キシレン及び/又はp−トルアルデヒドの製造方法 Download PDFInfo
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- JP6040933B2 JP6040933B2 JP2013505013A JP2013505013A JP6040933B2 JP 6040933 B2 JP6040933 B2 JP 6040933B2 JP 2013505013 A JP2013505013 A JP 2013505013A JP 2013505013 A JP2013505013 A JP 2013505013A JP 6040933 B2 JP6040933 B2 JP 6040933B2
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- 229940102001 zinc bromide Drugs 0.000 description 1
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Description
(式1)転化率(%)=((反応前の原料の物質量−反応後の原料の物質量)/反応前の原料の物質量)×100
(式2)選択率(%)=(生成物の物質量)/(反応前の原料の物質量−反応後の原料の物質量)×100
(式3)収率(%)=(生成物の物質量/反応前の原料の物質量)×100
25mLのナス型フラスコをアルゴン雰囲気とし、攪拌子、塩化アルミニウム(530mg)を加え、0℃に冷却し、攪拌した。テトラヒドロフラン(0.64mL)を加え、同温で15分間攪拌した後、アクロレイン(13.4mL)、イソプレン(20mL)を加え、25℃で72時間攪拌した。1mol/L水酸化ナトリウム水溶液(12mL)を加え、クロロホルムで抽出した。有機層をセライトろ過して得られた溶液をエバポレーターにて濃縮し、4−メチル−3−シクロヘキセンカルボキシアルデヒドの粗生成物を得た。この粗生成物を既知重量のエタノール(内部標準物質)と共に1H−NMR分析に供し、4−メチル−3−シクロヘキセンカルボキシアルデヒドの収率を算出した(収率68%)。この粗生成物を減圧下蒸留することにより精製し、4−メチル−3−シクロヘキセンカルボキシアルデヒドを単離した(収率65%)。
硝酸クロム(III)9水和物(7.7g)を蒸留水(25mL)に溶解し、アルミナ(日揮触媒化成、N613N)(19g)を加え、得られた懸濁液を120℃に加熱したホットプレート上で攪拌し、水分を蒸発させた。得られた固体を蒸発皿に加え、500℃で4時間焼成して、触媒Aを得た。
アルミナの代わりにシリカ−アルミナ(日揮触媒化成、N633HN、シリカ66.5%、アルミナ25.1%)(19g)を用いて、参考例1と同じ方法により触媒Bを調製した。
アルミナの代わりにシリカ(富士シリシア化学、CARiACT G3)(19g)を用いて、参考例1と同じ方法により触媒Cを調製した。
反応管に触媒A(200mg)を充填し、管状炉を400℃に加熱し、反応管の上部から窒素を10mL/minの流速で流通した。2時間後、管状炉を400℃に保持し、反応管の上部からキャリアガスとして窒素を10ml/minの流速で流通し、実施例1で得られた4−メチル−3−シクロヘキセンカルボキシアルデヒドを1.88g/hにて窒素気流と共に触媒層に供給した。30分後、反応管下端の捕集容器から767mgの有機層を得た。有機層中の各化合物の含有量を算出し、転化率、選択率及び収率を求めた。結果を表1に示す。
触媒A(200mg)の代わりに触媒B(200mg)を用いて、実施例2と同様な方法により反応を行い、転化率、選択率及び収率を算出した。結果を表1に示す。
管状炉の温度を400℃の代わりに300℃として、実施例3と同様な方法により反応を行い、転化率、選択率及び収率を算出した。結果を表1に示す。
触媒A(200mg)の代わりに触媒C(200mg)を用いて、実施例2と同様な方法により反応を行い、795mgの反応粗液を得た。反応粗液中の各化合物の含有量を算出し、転化率、選択率及び収率を求めた。結果を表1に示す。
触媒C(200mg)の代わりに触媒D(エヌ・イー・ケムキャット、5%白金含有、200mg)を用いて、実施例5と同様な方法により反応を行い、転化率、選択率及び収率を算出した。結果を表1に示す。
触媒C(200mg)の代わりに触媒E(エヌ・イー・ケムキャット、5%パラジウム含有、200mg)を用いて、実施例5と同様な方法により反応を行い、転化率、選択率及び収率を算出した。結果を表1に示す。
触媒C(200mg)の代わりに触媒F(エヌ・イー・ケムキャット、5%ルテニウム含有、53.17%含水、200mg)を用いて、実施例5と同様な方法により反応を行い、転化率、選択率及び収率を算出した。結果を表1に示す。
アルゴン雰囲気下で、20mLの反応容器に攪拌子、パラジウム担持活性炭(触媒G)(エヌ・イー・ケムキャット、10%パラジウム含有、100mg)、実施例1で得られた4−メチル−3−シクロヘキセンカルボキシアルデヒド(500mg)を加え、200℃に加熱し攪拌した。1.5時間後、反応液を室温まで冷却し、内部標準物質としてエタノール(70.1mg)を加え、攪拌した。得られた混液を1H−NMR分析に供し、混液中の化合物ピークとエタノールのピークの積分値比から化合物の生成量を算出し、転化率、選択率及び収率を求めた。結果を表1に示す。
2 キャリアガス導入口
3 気化器
4 反応管
5 管状炉
6 触媒層
7 反応粗液捕集容器(冷却器)
8 ガス開放口
Claims (7)
- イソプレンとアクロレインから4−メチル−3−シクロヘキセンカルボキシアルデヒドを製造する環化工程と、4−メチル−3−シクロヘキセンカルボキシアルデヒドから、触媒を用いる気相流通反応によってp−キシレン及び/又はp−トルアルデヒドを製造する芳香族化工程とを含む、p−キシレン及び/又はp−トルアルデヒドの製造方法。
- 芳香族化工程で使用する触媒が、金属及び/又は金属酸化物が担持された担体を含む触媒である、請求項1に記載の製造方法。
- 芳香族化工程で使用する触媒が、白金、ニッケル、パラジウム、ルテニウム、酸化白金、酸化銅、酸化鉄及び酸化クロムの群から選択される少なくとも1種の金属又は金属酸化物が担持された担体を含む触媒である、請求項1又は2に記載の製造方法。
- 芳香族化工程で使用する触媒が、アルミナ、シリカ−アルミナ、シリカ、ゼオライト、チタニア、マグネシア及びカーボンの群から選択される担体を含む触媒である、請求項1〜3のいずれか1項に記載の製造方法。
- 芳香族化工程で使用する触媒が、酸化クロム担持アルミナ、酸化クロム担持シリカ−アルミナ又は酸化クロム担持シリカである、請求項1〜4のいずれか1項に記載の製造方法。
- 芳香族化工程における気相流通反応の反応温度が300℃以上500℃以下である、請求項1〜5のいずれか1項に記載の製造方法。
- 環化工程が、ルイス酸を含有する触媒の存在下に行う工程である、請求項1〜6のいずれか1項に記載の製造方法。
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CN104693016B (zh) * | 2013-12-10 | 2017-04-12 | 中国科学院大连化学物理研究所 | 异戊二烯和丙烯醛制备对甲基苯甲醛的方法 |
KR101825652B1 (ko) | 2015-11-06 | 2018-02-05 | 주식회사 엘지화학 | 코폴리카보네이트 및 이를 포함하는 조성물 |
CN106883089B (zh) * | 2015-12-15 | 2019-10-25 | 中国科学院大连化学物理研究所 | 一种4-甲基-3-环己烯甲醛合成甲苯的方法 |
CN106883090B (zh) * | 2015-12-15 | 2020-02-21 | 中国科学院大连化学物理研究所 | 固体酸催化4-甲基-3-环己烯甲醛合成对二甲苯的方法 |
CN106883091B (zh) * | 2015-12-15 | 2020-02-07 | 中国科学院大连化学物理研究所 | 一种由4-甲基-3-环己烯甲醛选择性合成对二甲苯的方法 |
TWI630192B (zh) * | 2017-07-28 | 2018-07-21 | 遠東新世紀股份有限公司 | Method for preparing alkylbenzene |
CN112824360B (zh) * | 2019-11-21 | 2022-03-01 | 中国科学院大连化学物理研究所 | 一种铜基双金属催化剂高效催化3-环己烯甲醛转化制备甲苯的方法 |
CN112824359B (zh) * | 2019-11-21 | 2022-03-01 | 中国科学院大连化学物理研究所 | 一种贵金属负载型催化剂在合成对二甲苯中的应用 |
CN112824361B (zh) * | 2019-11-21 | 2022-03-25 | 中国科学院大连化学物理研究所 | 一种由镍铁双金属催化剂高效催化4-甲基-3-环己烯甲醛转化制备对二甲苯的方法 |
JPWO2022172968A1 (ja) | 2021-02-10 | 2022-08-18 | ||
US11325873B1 (en) * | 2021-07-28 | 2022-05-10 | Battelle Memorial Institute | Method and system embodiments for converting ethanol to para-xylene and ortho-xylene |
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JPS5186437A (ja) | 1975-01-28 | 1976-07-29 | Mitsubishi Gas Chemical Co | Futarusannokokushokukaboshiho |
JP2006305408A (ja) * | 2005-04-26 | 2006-11-09 | Tosoh Corp | 芳香族化反応触媒とその触媒を用いた芳香族炭化水素の製造方法 |
WO2011044243A1 (en) | 2009-10-06 | 2011-04-14 | Gevo, Inc. | Integrated process to selectively convert renewable isobutanol to p-xylene |
WO2012061372A1 (en) * | 2010-11-01 | 2012-05-10 | Gevo, Inc. | Renewable xylenes produced from biological c4 and c5 molecules |
US8969640B2 (en) * | 2011-11-23 | 2015-03-03 | Virent, Inc. | Dehydrogenation of alkanols to increase yield of aromatics |
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BR112014017804A8 (pt) | 2017-07-11 |
US20140378710A1 (en) | 2014-12-25 |
EP2808316A1 (en) | 2014-12-03 |
CN104010996B (zh) | 2015-11-25 |
US9024074B2 (en) | 2015-05-05 |
RU2014134643A (ru) | 2016-03-20 |
KR20140118991A (ko) | 2014-10-08 |
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