JP2012531384A5 - - Google Patents
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- Publication number
- JP2012531384A5 JP2012531384A5 JP2012516545A JP2012516545A JP2012531384A5 JP 2012531384 A5 JP2012531384 A5 JP 2012531384A5 JP 2012516545 A JP2012516545 A JP 2012516545A JP 2012516545 A JP2012516545 A JP 2012516545A JP 2012531384 A5 JP2012531384 A5 JP 2012531384A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- toluic
- propylbenzoic
- ethylbenzoic
- isomers
- 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.)
- Pending
Links
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 4
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical class OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 4
- GPSDUZXPYCFOSQ-UHFFFAOYSA-N m-toluic acid Chemical compound CC1=CC=CC(C(O)=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-N 0.000 claims description 4
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 claims description 4
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 claims description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 4
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical class OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 claims description 4
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical class OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical class C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 claims description 2
- ZYBVOCTZGINDED-UHFFFAOYSA-N 2-(hydroxymethoxy)benzoic acid Chemical compound OCOC1=CC=CC=C1C(O)=O ZYBVOCTZGINDED-UHFFFAOYSA-N 0.000 claims description 2
- MGMNPSAERQZUIM-UHFFFAOYSA-N 2-(hydroxymethyl)benzoic acid Chemical compound OCC1=CC=CC=C1C(O)=O MGMNPSAERQZUIM-UHFFFAOYSA-N 0.000 claims description 2
- CGMMPMYKMDITEA-UHFFFAOYSA-N 2-ethylbenzoic acid Chemical compound CCC1=CC=CC=C1C(O)=O CGMMPMYKMDITEA-UHFFFAOYSA-N 0.000 claims description 2
- WVDGHGISNBRCAO-UHFFFAOYSA-N 2-hydroxyisophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1O WVDGHGISNBRCAO-UHFFFAOYSA-N 0.000 claims description 2
- UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 claims description 2
- GADSJKKDLMALGL-UHFFFAOYSA-N 2-propylbenzoic acid Chemical compound CCCC1=CC=CC=C1C(O)=O GADSJKKDLMALGL-UHFFFAOYSA-N 0.000 claims description 2
- SKBJYRPOZXOUIG-UHFFFAOYSA-N 3-(hydroxymethyl)pyridine-2-carboxylic acid Chemical compound OCC1=CC=CN=C1C(O)=O SKBJYRPOZXOUIG-UHFFFAOYSA-N 0.000 claims description 2
- HXUSUAKIRZZMGP-UHFFFAOYSA-N 3-ethylbenzoic acid Chemical compound CCC1=CC=CC(C(O)=O)=C1 HXUSUAKIRZZMGP-UHFFFAOYSA-N 0.000 claims description 2
- BRARRAHGNDUELT-UHFFFAOYSA-N 3-hydroxypicolinic acid Chemical compound OC(=O)C1=NC=CC=C1O BRARRAHGNDUELT-UHFFFAOYSA-N 0.000 claims description 2
- WHKZBVQIMVUGIH-UHFFFAOYSA-N 3-hydroxyquinoline-2-carboxylic acid Chemical class C1=CC=C2C=C(O)C(C(=O)O)=NC2=C1 WHKZBVQIMVUGIH-UHFFFAOYSA-N 0.000 claims description 2
- GIFHXKJTAILWRE-UHFFFAOYSA-N 3-propylbenzoic acid Chemical compound CCCC1=CC=CC(C(O)=O)=C1 GIFHXKJTAILWRE-UHFFFAOYSA-N 0.000 claims description 2
- ZQVKTHRQIXSMGY-UHFFFAOYSA-N 4-Ethylbenzoic acid Chemical compound CCC1=CC=C(C(O)=O)C=C1 ZQVKTHRQIXSMGY-UHFFFAOYSA-N 0.000 claims description 2
- CHHQEMBTCQDAHF-UHFFFAOYSA-N 4-hydroxy-2,3-dimethoxybenzoic acid Chemical compound COC1=C(O)C=CC(C(O)=O)=C1OC CHHQEMBTCQDAHF-UHFFFAOYSA-N 0.000 claims description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 2
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 claims description 2
- ATZHGRNFEFVDDJ-UHFFFAOYSA-N 4-propylbenzoic acid Chemical compound CCCC1=CC=C(C(O)=O)C=C1 ATZHGRNFEFVDDJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000005711 Benzoic acid Substances 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical class C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 claims description 2
- ILUJQPXNXACGAN-UHFFFAOYSA-N ortho-methoxybenzoic acid Natural products COC1=CC=CC=C1C(O)=O ILUJQPXNXACGAN-UHFFFAOYSA-N 0.000 claims description 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims description 2
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical class OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 claims description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- OPVAJFQBSDUNQA-UHFFFAOYSA-N 3,4-dimethylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C=C1C OPVAJFQBSDUNQA-UHFFFAOYSA-N 0.000 description 2
- XBLVHTDFJBKJLG-UHFFFAOYSA-N Ethyl nicotinate Chemical compound CCOC(=O)C1=CC=CN=C1 XBLVHTDFJBKJLG-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- -1 aromatic carboxylic acids Chemical class 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- YNBADRVTZLEFNH-UHFFFAOYSA-N methyl nicotinate Chemical compound COC(=O)C1=CC=CN=C1 YNBADRVTZLEFNH-UHFFFAOYSA-N 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- YPMKPCAILYDVBN-UHFFFAOYSA-N (2-methylphenyl) benzoate Chemical compound CC1=CC=CC=C1OC(=O)C1=CC=CC=C1 YPMKPCAILYDVBN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- UUGLJVMIFJNVFH-UHFFFAOYSA-N Hexyl benzoate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1 UUGLJVMIFJNVFH-UHFFFAOYSA-N 0.000 description 1
- 125000005418 aryl aryl group Chemical group 0.000 description 1
- UYGHRCCJWWYXMY-UHFFFAOYSA-N butyl 4-methylbenzoate Chemical compound CCCCOC(=O)C1=CC=C(C)C=C1 UYGHRCCJWWYXMY-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- QSSJZLPUHJDYKF-UHFFFAOYSA-N methyl 4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C=C1 QSSJZLPUHJDYKF-UHFFFAOYSA-N 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- QEJPOSAIULNDLU-UHFFFAOYSA-N phenyl pyridine-3-carboxylate Chemical compound C=1C=CN=CC=1C(=O)OC1=CC=CC=C1 QEJPOSAIULNDLU-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102009031054.1 | 2009-06-30 | ||
| DE102009031054A DE102009031054A1 (de) | 2009-06-30 | 2009-06-30 | Kontinuierliches Verfahren zur Herstellung von Estern aromatischer Carbonsäuren |
| PCT/EP2010/003447 WO2011000464A2 (de) | 2009-06-30 | 2010-06-09 | Kontinuierliches verfahren zur herstellung von estern aromatischer carbonsäuren |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2012531384A JP2012531384A (ja) | 2012-12-10 |
| JP2012531384A5 true JP2012531384A5 (enExample) | 2014-08-14 |
Family
ID=43128202
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012516545A Pending JP2012531384A (ja) | 2009-06-30 | 2010-06-09 | 芳香族カルボン酸のエステルの連続的製造方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20120088918A1 (enExample) |
| EP (1) | EP2448904B1 (enExample) |
| JP (1) | JP2012531384A (enExample) |
| KR (1) | KR20120027004A (enExample) |
| CA (1) | CA2766955A1 (enExample) |
| DE (1) | DE102009031054A1 (enExample) |
| ES (1) | ES2404159T3 (enExample) |
| WO (1) | WO2011000464A2 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102006047619B4 (de) * | 2006-10-09 | 2008-11-13 | Clariant International Limited | Verfahren zur Herstellung basischer Fettsäureamide |
| DE102006047617B4 (de) * | 2006-10-09 | 2008-11-27 | Clariant International Limited | Verfahren zur Herstellung basischer (Meth)acrylamide |
| DE102008017215B4 (de) * | 2008-04-04 | 2012-08-09 | Clariant International Ltd. | Kontinuierliches Verfahren zur Herstellung von Amiden ethylenisch ungesättigter Carbonsäuren |
| DE102008017214B4 (de) * | 2008-04-04 | 2012-02-16 | Clariant International Limited | Kontinuierliches Verfahren zur Herstellung von Fettsäurealkanolamiden |
| DE102008017213B4 (de) * | 2008-04-04 | 2012-08-09 | Clariant International Limited | Kontinuierliches Verfahren zur Herstellung von Amiden aliphatischer Hydroxycarbonsäuren |
| DE102008017216B4 (de) * | 2008-04-04 | 2013-08-14 | Clariant International Ltd. | Kontinuierliches Verfahren zur Herstellung von Fettsäureamiden |
| DE102008017218B4 (de) * | 2008-04-04 | 2011-09-22 | Clariant International Ltd. | Kontinuierliches Verfahren zur Herstellung von Amiden niederer aliphatischer Carbonsäuren |
| DE102008017219A1 (de) * | 2008-04-04 | 2009-10-08 | Clariant International Ltd. | Verfahren zur Herstellung von Amiden in Gegenwart von überhitztem Wasser |
| DE102008017217A1 (de) * | 2008-04-04 | 2009-10-08 | Clariant International Ltd. | Kontinuierliches Verfahren zur Herstellung von Amiden aromatischer Carbonsäuren |
| DE102009031059A1 (de) | 2009-06-30 | 2011-01-05 | Clariant International Ltd. | Vorrichtung zur kontinuierlichen Durchführung chemischer Reaktionen bei hohen Temperaturen |
| DE102009042522A1 (de) | 2009-09-22 | 2011-04-07 | Clariant International Ltd. | Kontinuierliches Umesterungsverfahren |
| DE102009042523B4 (de) | 2009-09-22 | 2012-02-16 | Clariant International Ltd. | Vorrichtung und Verfahren zur kontinuierlichen Durchführung heterogen katalysierter chemischer Reaktionen bei hohen Temperaturen |
| DE102010056564A1 (de) | 2010-12-30 | 2012-07-05 | Clariant International Limited | Hydroxylgruppen und Estergruppen tragende Polymere und Verfahren zu ihrer Herstellung |
| DE102010056565A1 (de) | 2010-12-30 | 2012-07-05 | Clariant International Ltd. | Verfahren zur Modifizierung Hydroxylgruppen tragender Polymere |
| CN102260170B (zh) * | 2011-06-02 | 2014-10-15 | 浙江大学 | 微波管道化生产乙酸正t酯的方法 |
| US8957242B2 (en) * | 2013-03-15 | 2015-02-17 | Renewable Energy Group, Inc. | Dual catalyst esterification |
| CN104710314A (zh) * | 2015-03-25 | 2015-06-17 | 河南师范大学 | 一种水杨酸酯的制备方法 |
| CN104803848B (zh) * | 2015-04-23 | 2016-07-13 | 安徽佳先功能助剂股份有限公司 | 采用含有氯化钠的苯甲酸为原料生产苯甲酸甲酯的方法 |
| CN108476188B (zh) * | 2015-11-02 | 2021-05-25 | 三星电子株式会社 | 在波束形成通信系统中发送或接收参考信号的方法和装置 |
| DE102019006639A1 (de) | 2019-09-20 | 2021-03-25 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Kontinuierliches Verfahren zum Erhitzen von Medien mittels Mikrowellenstrahlung und dafür geeignete Mikrowellenanlage |
| CN119219490B (zh) * | 2024-12-03 | 2025-03-04 | 宿州恒昶生物科技有限公司 | 一种羟苯甲酯的制备工艺 |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3461261A (en) * | 1966-10-31 | 1969-08-12 | Du Pont | Heating apparatus |
| DE3060279D1 (en) * | 1979-06-20 | 1982-05-19 | Basf Canada Inc | Use of microwave energy in the production of plasticizer esters |
| JPH01133910A (ja) * | 1987-06-08 | 1989-05-26 | Cil Inc | マイクロ波エネルギ−を使用して発煙硫酸から三酸化硫黄を発生させる方法及び装置 |
| WO1990003840A1 (en) | 1988-10-10 | 1990-04-19 | Commonwealth Scientific And Industrial Research Organisation | Method and apparatus for continuous chemical reactions |
| JP2784789B2 (ja) * | 1989-03-27 | 1998-08-06 | 山本化成株式会社 | ２―アルキルアントラキノンの製造方法 |
| US6020579A (en) * | 1997-01-06 | 2000-02-01 | International Business Machines Corporation | Microwave applicator having a mechanical means for tuning |
| US5114684A (en) * | 1990-12-13 | 1992-05-19 | Serawaste Systems Corporation | In-line electromagnetic energy wave applicator |
| US5471037A (en) * | 1992-08-18 | 1995-11-28 | E. I. Du Pont De Nemours And Company | Process for preparing polymeric material with microwave |
| JPH07330667A (ja) * | 1994-06-10 | 1995-12-19 | Koichi Shinozaki | マイクロ波を加熱に用いるエステル類の製造方法 |
| FR2751830B1 (fr) * | 1996-07-23 | 1998-10-23 | Prolabo Sa | Dispositif pour realiser des reactions chimiques sous micro-ondes sur une grande quantite de produits |
| JP4376627B2 (ja) * | 2001-10-19 | 2009-12-02 | バイオタージ・アクチボラゲット | マイクロ波加熱装置、マイクロ波加熱システム、およびマイクロ波加熱装置またはマイクロ波加熱システムの使用方法 |
| JP2004059517A (ja) * | 2002-07-30 | 2004-02-26 | New Japan Chem Co Ltd | ヒドロキシ安息香酸エステル類の製造方法 |
| US6867400B2 (en) * | 2002-07-31 | 2005-03-15 | Cem Corporation | Method and apparatus for continuous flow microwave-assisted chemistry techniques |
| FR2849343B1 (fr) * | 2002-12-23 | 2009-01-23 | Aldivia | Synthese chimique comportant un traitement thermique par chauffage dielectrique intermittent, combine a un systeme de recirculation |
| JP4759668B2 (ja) * | 2004-05-11 | 2011-08-31 | 株式会社Ｉｄｘ | マイクロ波加熱装置 |
| US20050274065A1 (en) | 2004-06-15 | 2005-12-15 | Carnegie Mellon University | Methods for producing biodiesel |
| JP2006181533A (ja) * | 2004-12-28 | 2006-07-13 | Idx Corp | マイクロ波化学反応装置 |
| JP2006272055A (ja) * | 2005-03-28 | 2006-10-12 | Idx Corp | マイクロ波化学反応装置 |
| JP2007222696A (ja) * | 2005-12-23 | 2007-09-06 | Tokyo Electric Power Co Inc:The | マイクロ波反応用の触媒カラム及びそれを用いた分解処理方法 |
| CN100352793C (zh) * | 2006-01-20 | 2007-12-05 | 杨鸿生 | 用于以天然气制乙烯的槽波导微波化学反应设备及制备方法 |
| PL2013319T3 (pl) | 2006-04-28 | 2019-07-31 | Sk Chemicals Co., Ltd. | Sposób wytwarzania estru alkilowego kwasu tłuszczowego z użyciem destylatu kwasu tłuszczowego |
| EP2079680B1 (de) * | 2006-10-09 | 2015-07-01 | Clariant Finance (BVI) Limited | Verfahren zur herstellung von fettsäurealkanolamiden |
| US8128788B2 (en) * | 2008-09-19 | 2012-03-06 | Rf Thummim Technologies, Inc. | Method and apparatus for treating a process volume with multiple electromagnetic generators |
-
2009
- 2009-06-30 DE DE102009031054A patent/DE102009031054A1/de not_active Withdrawn
-
2010
- 2010-06-09 JP JP2012516545A patent/JP2012531384A/ja active Pending
- 2010-06-09 EP EP10723943.6A patent/EP2448904B1/de not_active Not-in-force
- 2010-06-09 US US13/378,167 patent/US20120088918A1/en not_active Abandoned
- 2010-06-09 WO PCT/EP2010/003447 patent/WO2011000464A2/de not_active Ceased
- 2010-06-09 KR KR1020117025263A patent/KR20120027004A/ko not_active Withdrawn
- 2010-06-09 CA CA2766955A patent/CA2766955A1/en not_active Abandoned
- 2010-06-09 ES ES10723943T patent/ES2404159T3/es active Active
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