JP2009521316A5 - - Google Patents
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- Publication number
- JP2009521316A5 JP2009521316A5 JP2008547537A JP2008547537A JP2009521316A5 JP 2009521316 A5 JP2009521316 A5 JP 2009521316A5 JP 2008547537 A JP2008547537 A JP 2008547537A JP 2008547537 A JP2008547537 A JP 2008547537A JP 2009521316 A5 JP2009521316 A5 JP 2009521316A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- heteropolyacid
- solid particles
- molybdenum
- phosphorus
- 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
- 150000001875 compounds Chemical class 0.000 claims 122
- 239000011964 heteropoly acid Substances 0.000 claims 94
- 239000002245 particle Substances 0.000 claims 60
- 239000007787 solid Substances 0.000 claims 60
- 229910052698 phosphorus Inorganic materials 0.000 claims 46
- 239000011574 phosphorus Substances 0.000 claims 46
- 238000000034 method Methods 0.000 claims 43
- -1 phosphorus compound Chemical class 0.000 claims 40
- 229910052792 caesium Inorganic materials 0.000 claims 28
- 239000005078 molybdenum compound Substances 0.000 claims 26
- 150000002752 molybdenum compounds Chemical class 0.000 claims 26
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims 20
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 20
- 229910052750 molybdenum Inorganic materials 0.000 claims 20
- 239000011733 molybdenum Substances 0.000 claims 20
- 239000010949 copper Substances 0.000 claims 18
- 150000003682 vanadium compounds Chemical class 0.000 claims 17
- 239000003054 catalyst Substances 0.000 claims 16
- 238000001035 drying Methods 0.000 claims 16
- 238000001704 evaporation Methods 0.000 claims 16
- 239000007788 liquid Substances 0.000 claims 16
- 230000001376 precipitating effect Effects 0.000 claims 16
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims 15
- 229910052720 vanadium Inorganic materials 0.000 claims 15
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical group [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims 15
- 239000007864 aqueous solution Substances 0.000 claims 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 13
- 229910052760 oxygen Inorganic materials 0.000 claims 13
- 239000001301 oxygen Substances 0.000 claims 13
- 239000000243 solution Substances 0.000 claims 12
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 10
- 239000005749 Copper compound Substances 0.000 claims 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 10
- 150000001299 aldehydes Chemical class 0.000 claims 10
- 229910052802 copper Inorganic materials 0.000 claims 10
- 150000001880 copper compounds Chemical class 0.000 claims 10
- 239000000126 substance Substances 0.000 claims 10
- 239000012018 catalyst precursor Substances 0.000 claims 7
- 229910052684 Cerium Inorganic materials 0.000 claims 5
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims 5
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims 5
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims 5
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 5
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 5
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims 5
- 229910052782 aluminium Inorganic materials 0.000 claims 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 5
- 229910052787 antimony Inorganic materials 0.000 claims 5
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims 5
- 229910052785 arsenic Inorganic materials 0.000 claims 5
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims 5
- 229910052788 barium Inorganic materials 0.000 claims 5
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims 5
- 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 5
- 229910052804 chromium Inorganic materials 0.000 claims 5
- 239000011651 chromium Substances 0.000 claims 5
- 229910017052 cobalt Inorganic materials 0.000 claims 5
- 239000010941 cobalt Substances 0.000 claims 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 5
- 229910052733 gallium Inorganic materials 0.000 claims 5
- 229910052732 germanium Inorganic materials 0.000 claims 5
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims 5
- 229910052738 indium Inorganic materials 0.000 claims 5
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims 5
- 229910052742 iron Inorganic materials 0.000 claims 5
- 229910052746 lanthanum Inorganic materials 0.000 claims 5
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims 5
- 239000011133 lead Substances 0.000 claims 5
- 229910052749 magnesium Inorganic materials 0.000 claims 5
- 239000011777 magnesium Substances 0.000 claims 5
- 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 5
- 229910052759 nickel Inorganic materials 0.000 claims 5
- 229910052758 niobium Inorganic materials 0.000 claims 5
- 239000010955 niobium Substances 0.000 claims 5
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims 5
- 239000011591 potassium Chemical group 0.000 claims 5
- 229910052700 potassium Inorganic materials 0.000 claims 5
- 229910052701 rubidium Inorganic materials 0.000 claims 5
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical group [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 claims 5
- 229920006395 saturated elastomer Polymers 0.000 claims 5
- 229910052710 silicon Inorganic materials 0.000 claims 5
- 239000010703 silicon Substances 0.000 claims 5
- 229910052709 silver Inorganic materials 0.000 claims 5
- 239000004332 silver Substances 0.000 claims 5
- 229910052708 sodium Chemical group 0.000 claims 5
- 239000011734 sodium Chemical group 0.000 claims 5
- 229910052715 tantalum Inorganic materials 0.000 claims 5
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims 5
- 229910052718 tin Inorganic materials 0.000 claims 5
- 239000011135 tin Substances 0.000 claims 5
- 229910052719 titanium Inorganic materials 0.000 claims 5
- 239000010936 titanium Substances 0.000 claims 5
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims 5
- 229910052721 tungsten Inorganic materials 0.000 claims 5
- 239000010937 tungsten Substances 0.000 claims 5
- 229910052725 zinc Inorganic materials 0.000 claims 5
- 239000011701 zinc Substances 0.000 claims 5
- 229910052726 zirconium Inorganic materials 0.000 claims 5
- 229910052797 bismuth Inorganic materials 0.000 claims 4
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims 4
- 238000001354 calcination Methods 0.000 claims 4
- 239000007800 oxidant agent Substances 0.000 claims 4
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical group CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 claims 3
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 claims 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 2
- 239000011230 binding agent Substances 0.000 claims 2
- 229910052796 boron Inorganic materials 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/316,211 US7273829B2 (en) | 2005-12-22 | 2005-12-22 | Catalyst for oxidation of saturated and unsaturated aldehydes to unsaturated carboxylic acid, method of making and method of using thereof |
| US11/316,211 | 2005-12-22 | ||
| PCT/US2006/048757 WO2007073492A2 (en) | 2005-12-22 | 2006-12-22 | Catalyst for oxidation of saturated and unsaturated aldehydes to unsaturated carboxylic acid, method of making and method of using thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009521316A JP2009521316A (ja) | 2009-06-04 |
| JP2009521316A5 true JP2009521316A5 (enExample) | 2010-02-12 |
| JP5384940B2 JP5384940B2 (ja) | 2014-01-08 |
Family
ID=38189123
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008547537A Expired - Fee Related JP5384940B2 (ja) | 2005-12-22 | 2006-12-22 | 飽和および不飽和アルデヒドの不飽和カルボン酸への酸化のための触媒およびその製造方法と使用方法 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US7273829B2 (enExample) |
| EP (1) | EP1971565B1 (enExample) |
| JP (1) | JP5384940B2 (enExample) |
| WO (1) | WO2007073492A2 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8481448B2 (en) * | 2010-07-19 | 2013-07-09 | Saudi Basic Industries Corporation | Catalyst for oxidation of saturated and unsaturated aldehydes to unsaturated carboxylic acid, method of making and method of using thereof |
| JP6653871B2 (ja) * | 2015-03-11 | 2020-02-26 | 国立大学法人北海道大学 | メタクリル酸製造用触媒及びその製造方法、並びにメタクリル酸の製造方法 |
| KR102242614B1 (ko) * | 2016-12-12 | 2021-04-20 | 미쯔비시 케미컬 주식회사 | α,β-불포화 카복실산 제조용 촉매 전구체의 제조 방법, α,β-불포화 카복실산 제조용 촉매의 제조 방법, α,β-불포화 카복실산의 제조 방법 및 α,β-불포화 카복실산 에스터의 제조 방법 |
| CN108906123A (zh) * | 2018-07-03 | 2018-11-30 | 上海应用技术大学 | 一种杂多酸-氧化石墨烯复合催化材料、制备方法及其应用 |
| WO2022050110A1 (ja) * | 2020-09-03 | 2022-03-10 | 株式会社日本触媒 | アクリル酸製造用触媒とその製造方法およびアクリル酸の製造方法 |
| CN114276850B (zh) * | 2021-12-24 | 2023-02-07 | 安徽工业大学 | 一种氟掺杂石墨烯负载Pb复合材料及其制备方法和应用 |
| CN116196950B (zh) * | 2023-02-16 | 2024-05-24 | 北华大学 | 一种双金属掺杂杂多酸催化剂的合成方法及在木质素转化中的应用 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5413876B2 (enExample) * | 1974-10-23 | 1979-06-02 | ||
| US4118419A (en) * | 1975-12-03 | 1978-10-03 | Mitsubishi Rayon Company, Ltd. | Catalytic process for the preparation of an unsaturated carboxylic acid |
| JPS60232247A (ja) * | 1984-05-02 | 1985-11-18 | Nippon Shokubai Kagaku Kogyo Co Ltd | ヘテロポリ酸系触媒の再生方法 |
| JP2574948B2 (ja) * | 1990-02-08 | 1997-01-22 | 株式会社日本触媒 | メタクリル酸の製造方法 |
| DE4022212A1 (de) * | 1990-07-12 | 1992-01-16 | Basf Ag | Massen der allgemeinen formel mo(pfeil abwaerts)1(pfeil abwaerts)(pfeil abwaerts)2(pfeil abwaerts)(pfeil hoch)p(pfeil hoch)(pfeil abwaerts)a(pfeil abwaerts)(pfeil hoch)v(pfeil hoch)(pfeil abwaerts)b(pfeil abwaerts)(pfeil hoch)x(pfeil hoch)(pfeil hoch)1(pfeil hoch)(pfeil abwaerts)c(pfeil abwaerts)(pfeil hoch)x(pfeil hoch)(pfeil hoch)2(pfeil hoch)(pfeil abwaerts)d(pfeil abwaerts)(pfeil hoch)x(pfeil hoch)(pfeil hoch)3(pfeil hoch)(pfeil abwaerts)e(pfeil abwaerts)(pfeil hoch)s(pfeil hoch)(pfeil hoch)b(pfeil hoch)(pfeil abwaerts)f(pfeil abwaerts)(pfeil hoch)r(pfeil hoch)(pfeil hoch)e(pfeil hoch)(pfeil abwaerts)g(pfeil abwaerts)(pfeil hoch)s(pfeil hoch)(pfeil abwaerts)h(pfeil abwaerts)(pfeil hoch)o(pfeil hoch)(pfeil abwaerts)n(pfeil abwaerts) |
| US5198579A (en) * | 1990-11-14 | 1993-03-30 | Mitsui Toatsu Chemicals, Inc. | Catalyst for oxidizing methacrolein and method for preparing methacrylic acid |
| JPH0531368A (ja) * | 1990-11-14 | 1993-02-09 | Mitsui Toatsu Chem Inc | メタクリル酸製造用触媒及びメタクリル酸の製造方法 |
| TW349033B (en) | 1994-05-31 | 1999-01-01 | Nippon Catalytic Chem Ind | Catalyst for production of methacrylic acid and method for production of methacrylic acid by the use of the catalysta catalyst for the production of methacrylic acid by the vapor-phase catalytic oxidation and/or oxidative dehydrogenation of at least one compound |
| JPH08157414A (ja) * | 1994-12-01 | 1996-06-18 | Mitsui Toatsu Chem Inc | メタクリル酸製造用触媒及びメタクリル酸の製造方法 |
| JP3370589B2 (ja) * | 1997-12-25 | 2003-01-27 | 三菱レイヨン株式会社 | メタクリル酸製造用触媒およびそれを用いたメタクリル酸の製造法 |
| US5990348A (en) | 1998-01-05 | 1999-11-23 | Sunoco, Inc. | Conversion of alkanes to unsaturated carboxylic acids over heteroploy acids supported on polyoxometallate salts |
| US6060419A (en) * | 1998-01-05 | 2000-05-09 | Sunoco, Inc. (R&M) | Wells-Dawson type heteropolyacids, their preparation and use as oxidation catalysts |
| US6043184A (en) * | 1998-01-05 | 2000-03-28 | Sunoco, Inc. (R&M) | Heteropoly acids supported on polyoxometallate salts and their preparation |
| WO2001014057A1 (en) * | 1999-08-19 | 2001-03-01 | China Petro-Chemical Corporation | Fluid bed catalyst for ammoxidation of propylene to acrylonitrile |
| US6387841B1 (en) * | 1999-08-23 | 2002-05-14 | Rohm And Haas Company | Polyoxometallate supported catalysts |
| MXPA03002374A (es) * | 2000-09-21 | 2003-06-30 | Nippon Kayaku Kabushiki Kaisha | Catalizador para produccion de acido metacrilico, catalizador revestido y proceso para produccion del mismo. |
| JP4022047B2 (ja) * | 2001-02-07 | 2007-12-12 | 三菱レイヨン株式会社 | メタクリル酸合成用触媒の製造方法、メタクリル酸合成用触媒およびメタクリル酸の製造方法 |
| JP4634633B2 (ja) * | 2001-03-30 | 2011-02-16 | 三菱レイヨン株式会社 | 不飽和カルボン酸合成用触媒、その調製方法、およびその触媒を用いた不飽和カルボン酸の合成方法 |
| JP2002306970A (ja) * | 2001-04-12 | 2002-10-22 | Mitsubishi Rayon Co Ltd | メタクリル酸製造用触媒、その製造方法、および、メタクリル酸の製造方法 |
| MY144325A (en) * | 2003-02-20 | 2011-08-29 | Nippon Kayaku Kk | Catalyst for producing methacrylic acid and preparation method thereof |
-
2005
- 2005-12-22 US US11/316,211 patent/US7273829B2/en not_active Expired - Lifetime
-
2006
- 2006-12-22 EP EP06848678.6A patent/EP1971565B1/en not_active Not-in-force
- 2006-12-22 JP JP2008547537A patent/JP5384940B2/ja not_active Expired - Fee Related
- 2006-12-22 WO PCT/US2006/048757 patent/WO2007073492A2/en not_active Ceased
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