JP2007514780A5 - - Google Patents
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- Publication number
- JP2007514780A5 JP2007514780A5 JP2006545641A JP2006545641A JP2007514780A5 JP 2007514780 A5 JP2007514780 A5 JP 2007514780A5 JP 2006545641 A JP2006545641 A JP 2006545641A JP 2006545641 A JP2006545641 A JP 2006545641A JP 2007514780 A5 JP2007514780 A5 JP 2007514780A5
- Authority
- JP
- Japan
- Prior art keywords
- aromatic hydrocarbon
- polycyclic aromatic
- catalyst
- anthracene
- oxidation
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 claims 44
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims 36
- 239000003054 catalyst Substances 0.000 claims 32
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 claims 28
- GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 claims 24
- 230000003647 oxidation Effects 0.000 claims 21
- 238000007254 oxidation reaction Methods 0.000 claims 21
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 20
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 18
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 18
- 229910052794 bromium Inorganic materials 0.000 claims 18
- 229910001385 heavy metal Inorganic materials 0.000 claims 16
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 claims 16
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 11
- 229910001882 dioxygen Inorganic materials 0.000 claims 11
- 239000007791 liquid phase Substances 0.000 claims 11
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 claims 9
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 claims 9
- 229910052684 Cerium Inorganic materials 0.000 claims 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims 6
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims 6
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 claims 6
- 229910017052 cobalt Inorganic materials 0.000 claims 6
- 239000010941 cobalt Substances 0.000 claims 6
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims 6
- 229910052726 zirconium Inorganic materials 0.000 claims 6
- 229910052751 metal Inorganic materials 0.000 claims 5
- 239000002184 metal Substances 0.000 claims 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims 4
- SIEILFNCEFEENQ-UHFFFAOYSA-N dibromoacetic acid Chemical compound OC(=O)C(Br)Br SIEILFNCEFEENQ-UHFFFAOYSA-N 0.000 claims 4
- 229910052735 hafnium Inorganic materials 0.000 claims 4
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims 4
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims 4
- 150000002739 metals Chemical group 0.000 claims 4
- 230000001590 oxidative effect Effects 0.000 claims 4
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 claims 4
- 239000010936 titanium Substances 0.000 claims 4
- 229910052719 titanium Inorganic materials 0.000 claims 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 3
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 claims 3
- RVHSTXJKKZWWDQ-UHFFFAOYSA-N 1,1,1,2-tetrabromoethane Chemical compound BrCC(Br)(Br)Br RVHSTXJKKZWWDQ-UHFFFAOYSA-N 0.000 claims 2
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 claims 2
- YGYNBBAUIYTWBF-UHFFFAOYSA-N 2,6-dimethylnaphthalene Chemical compound C1=C(C)C=CC2=CC(C)=CC=C21 YGYNBBAUIYTWBF-UHFFFAOYSA-N 0.000 claims 2
- LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 claims 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 2
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 claims 2
- 239000006227 byproduct Substances 0.000 claims 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims 2
- 229910052748 manganese Inorganic materials 0.000 claims 2
- 239000011572 manganese Substances 0.000 claims 2
- 229910052750 molybdenum Inorganic materials 0.000 claims 2
- 239000011733 molybdenum Substances 0.000 claims 2
- 229910052759 nickel Inorganic materials 0.000 claims 2
- 238000005504 petroleum refining Methods 0.000 claims 2
- 229910052720 vanadium Inorganic materials 0.000 claims 2
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims 2
- SPOQSWFEPFFHCR-UHFFFAOYSA-N [Ce].[Mn].[Co] Chemical compound [Ce].[Mn].[Co] SPOQSWFEPFFHCR-UHFFFAOYSA-N 0.000 claims 1
- NVKKKCKOUWMITE-UHFFFAOYSA-N [Ce].[Mn].[Co].[Zr] Chemical compound [Ce].[Mn].[Co].[Zr] NVKKKCKOUWMITE-UHFFFAOYSA-N 0.000 claims 1
- -1 aromatic carboxylic acids Chemical class 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 230000000630 rising effect Effects 0.000 claims 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53076203P | 2003-12-18 | 2003-12-18 | |
| US53075903P | 2003-12-18 | 2003-12-18 | |
| US60/530,762 | 2003-12-18 | ||
| US60/530,759 | 2003-12-18 | ||
| US10/980,718 | 2004-11-03 | ||
| US10/980,718 US7378544B2 (en) | 2003-12-18 | 2004-11-03 | Anthracene and other polycyclic aromatics as activators in the oxidation of aromatic hydrocarbons |
| PCT/US2004/037751 WO2005066106A2 (en) | 2003-12-18 | 2004-11-12 | Anthracene and other polycyclic aromatics as activators in the oxidation of aromatic hydrocarbons |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007514780A JP2007514780A (ja) | 2007-06-07 |
| JP2007514780A5 true JP2007514780A5 (enExample) | 2007-11-01 |
| JP4861190B2 JP4861190B2 (ja) | 2012-01-25 |
Family
ID=34753682
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006545641A Expired - Fee Related JP4861190B2 (ja) | 2003-12-18 | 2004-11-12 | 芳香族炭化水素類の酸化における活性剤としてのアントラセン及び他の多環式芳香族化合物 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7378544B2 (enExample) |
| EP (1) | EP1694624A2 (enExample) |
| JP (1) | JP4861190B2 (enExample) |
| KR (1) | KR101176390B1 (enExample) |
| CN (1) | CN1894191B (enExample) |
| BR (1) | BRPI0417617B1 (enExample) |
| CA (1) | CA2546018C (enExample) |
| MX (1) | MXPA06006665A (enExample) |
| RU (1) | RU2362762C2 (enExample) |
| WO (1) | WO2005066106A2 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101109436B (zh) * | 2006-07-21 | 2011-02-16 | 北京交通大学 | 用于动力传动的增速或减速齿轮副 |
| RU2458042C2 (ru) * | 2010-03-01 | 2012-08-10 | Общество с ограниченной ответственностью "НИПИМ-Новые химические технологии" (ООО "НИПИМ-НХИМТЕХ") | Способ получения и очистки изофталевой кислоты |
| CN103012120A (zh) * | 2011-09-27 | 2013-04-03 | 中国石油化工股份有限公司 | 一种氧化精制法制取对苯二甲酸的方法 |
| US20130172609A1 (en) * | 2011-12-29 | 2013-07-04 | Uop Llc | Process for oxidizing an alkyl-aromatic compound |
| CN110560109B (zh) * | 2018-06-05 | 2021-11-30 | 中国石油化工股份有限公司 | 用于生产偏苯三酸酐的催化剂 |
| CN110560114B (zh) * | 2018-06-05 | 2021-11-30 | 中国石油化工股份有限公司 | 用于提高偏苯三酸酐收率的催化剂 |
| CN110560112B (zh) * | 2018-06-05 | 2021-11-30 | 中国石油化工股份有限公司 | 用于制备偏苯三酸酐的催化剂 |
| CN110560115B (zh) * | 2018-06-05 | 2021-11-30 | 中国石油化工股份有限公司 | 用于合成偏苯三酸酐的催化剂 |
| CN110560116B (zh) * | 2018-06-05 | 2021-11-30 | 中国石油化工股份有限公司 | 用于偏三甲苯氧化制备偏酐的催化剂 |
| CN110560111B (zh) * | 2018-06-05 | 2021-11-30 | 中国石油化工股份有限公司 | 用于偏三甲苯合成偏酐的催化剂 |
| CN110560113B (zh) * | 2018-06-05 | 2021-11-30 | 中国石油化工股份有限公司 | 用于偏三甲苯催化氧化的催化剂 |
| CN110560110B (zh) * | 2018-06-05 | 2021-11-30 | 中国石油化工股份有限公司 | 用于偏三甲苯氧化合成偏酐的催化剂 |
| CN108794321B (zh) * | 2018-07-16 | 2021-01-29 | 山东冠森高分子材料科技股份有限公司 | 连续流微通道反应器中合成芳香羧酸类化合物的方法 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2833816A (en) | 1954-05-03 | 1958-05-06 | Mid Century Corp | Preparation of aromatic polycarboxylic acids |
| US3855252A (en) * | 1968-07-15 | 1974-12-17 | Ashland Oil Inc | Liquid phase oxidation of condensed-ring aromatic hydrocarbons |
| KR100427298B1 (ko) * | 2001-03-31 | 2004-04-17 | 한국화학연구원 | 알킬방향족 화합물의 액상산화에 의한 방향족카르복시산의 제조방법 |
| US4755622A (en) | 1983-12-29 | 1988-07-05 | Amoco Corporation | Process for the production of trimellitic acid and pyromellitic acid by staged bromine addition in an oxidation of polyalkylaromatics |
| US4992579A (en) | 1989-12-18 | 1991-02-12 | Amoco Corporation | Process for the production of trimellitic acid |
| US5095143A (en) * | 1990-06-13 | 1992-03-10 | Amoco Corporation | Method for increasing the efficiency of liquid phase oxidation reactions |
| US5183933A (en) | 1991-10-15 | 1993-02-02 | Amoco Corporation | Process for preparing 2,6-naphthalene-dicarboxylic acid |
| RU2030386C1 (ru) * | 1992-06-23 | 1995-03-10 | Научно-исследовательский и проектный институт мономеров с опытным заводом | Способ получения нафталин-2,6-дикарбоновой кислоты |
| JPH06211740A (ja) * | 1992-07-06 | 1994-08-02 | Osaka City | ４，４´−ビフェニルジカルボン酸の製造方法 |
| JPH11335317A (ja) * | 1998-05-27 | 1999-12-07 | Mitsubishi Gas Chem Co Inc | トリメリット酸の製造法 |
| JPH11335321A (ja) * | 1998-05-22 | 1999-12-07 | Mitsui Chem Inc | 芳香族カルボン酸の製造方法 |
| US6194607B1 (en) | 1998-12-22 | 2001-02-27 | Samsung General Chemicals Co., Ltd. | Method of producing aromatic carboxylic acids by oxidizing alkyl aromatic hydrocarbons or partially oxidized intermediates thereof |
| JP2001019658A (ja) * | 1999-07-05 | 2001-01-23 | Mitsui Chemicals Inc | 芳香族カルボン酸の製造方法 |
| CA2396967A1 (en) * | 2000-01-21 | 2001-07-26 | Bp Corporation North America Inc. | Production of high purity aromatic carboxylic acid by oxidation in benzoic acid and water solvent |
| JP4788023B2 (ja) * | 2000-06-27 | 2011-10-05 | 三菱瓦斯化学株式会社 | 液相酸化反応母液からの触媒成分の回収方法 |
| JP2003342228A (ja) * | 2002-05-28 | 2003-12-03 | Mitsubishi Gas Chem Co Inc | ビフェニルテトラカルボン酸の製造法 |
| DE602004007654T2 (de) | 2003-06-06 | 2008-04-10 | Bp Corporation North America Inc., Warrenville | Oxidation von aromatischen kohlenwasserstoffen unter verwendung von bromierten anthracenen als promotoren |
-
2004
- 2004-11-03 US US10/980,718 patent/US7378544B2/en not_active Expired - Fee Related
- 2004-11-12 RU RU2006123766/04A patent/RU2362762C2/ru not_active IP Right Cessation
- 2004-11-12 MX MXPA06006665A patent/MXPA06006665A/es active IP Right Grant
- 2004-11-12 EP EP04810807A patent/EP1694624A2/en not_active Withdrawn
- 2004-11-12 JP JP2006545641A patent/JP4861190B2/ja not_active Expired - Fee Related
- 2004-11-12 WO PCT/US2004/037751 patent/WO2005066106A2/en not_active Ceased
- 2004-11-12 KR KR1020067012871A patent/KR101176390B1/ko not_active Expired - Fee Related
- 2004-11-12 CA CA2546018A patent/CA2546018C/en not_active Expired - Fee Related
- 2004-11-12 CN CN2004800375967A patent/CN1894191B/zh not_active Expired - Fee Related
- 2004-11-12 BR BRPI0417617-0A patent/BRPI0417617B1/pt not_active IP Right Cessation
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