JP2010513502A5 - - Google Patents
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- JP2010513502A5 JP2010513502A5 JP2009542869A JP2009542869A JP2010513502A5 JP 2010513502 A5 JP2010513502 A5 JP 2010513502A5 JP 2009542869 A JP2009542869 A JP 2009542869A JP 2009542869 A JP2009542869 A JP 2009542869A JP 2010513502 A5 JP2010513502 A5 JP 2010513502A5
- Authority
- JP
- Japan
- Prior art keywords
- dehydrogenation catalyst
- group
- formula
- compound
- hydrocarbyl group
- 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.)
- Abandoned
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- 238000000034 method Methods 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 7
- 239000003054 catalyst Substances 0.000 claims 6
- 238000006356 dehydrogenation reaction Methods 0.000 claims 6
- 229910052751 metal Inorganic materials 0.000 claims 6
- 239000002184 metal Substances 0.000 claims 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 5
- 239000007800 oxidant agent Substances 0.000 claims 5
- 230000001590 oxidative effect Effects 0.000 claims 5
- -1 potassium ferricyanide Chemical compound 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 239000000126 substance Substances 0.000 claims 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims 4
- 229920000642 polymer Polymers 0.000 claims 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 239000003880 polar aprotic solvent Substances 0.000 claims 3
- 239000011541 reaction mixture Substances 0.000 claims 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 2
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims 1
- 229910020175 SiOH Inorganic materials 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 229910021536 Zeolite Inorganic materials 0.000 claims 1
- IKWTVSLWAPBBKU-UHFFFAOYSA-N a1010_sial Chemical compound O=[As]O[As]=O IKWTVSLWAPBBKU-UHFFFAOYSA-N 0.000 claims 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims 1
- 229910000413 arsenic oxide Inorganic materials 0.000 claims 1
- 229960002594 arsenic trioxide Drugs 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 claims 1
- 229910000422 cerium(IV) oxide Inorganic materials 0.000 claims 1
- 239000003610 charcoal Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 229910000428 cobalt oxide Inorganic materials 0.000 claims 1
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 claims 1
- 239000000571 coke Substances 0.000 claims 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims 1
- 229910021472 group 8 element Inorganic materials 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 239000002638 heterogeneous catalyst Substances 0.000 claims 1
- 239000002815 homogeneous catalyst Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 claims 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 claims 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 230000000737 periodic effect Effects 0.000 claims 1
- 229910052711 selenium Inorganic materials 0.000 claims 1
- 239000011669 selenium Substances 0.000 claims 1
- 239000000377 silicon dioxide Substances 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 229910001930 tungsten oxide Inorganic materials 0.000 claims 1
- 239000010457 zeolite Substances 0.000 claims 1
Claims (10)
- 式(I)
非希釈液体アンモニア中で、または液体アンモニアと極性非プロトン溶媒との混合物中で、
式(II)
式中、R1およびR2は、それぞれ独立して、(a)水素、(b)ヒドロカルビル基、(c)NR3R4(式中、R3およびR4は、それぞれ独立して、Hおよびヒドロカルビル基から選択される)、(d)
から選択される]
から選択される、方法。 - (a)R1とR2の一方または両方がHであるか、
(b)R1とR2の一方または両方がNH2であるか、または
(c)R1とR2の一方または両方がN(CH3)2である
請求項1に記載の方法。 - 反応混合物が
(a)非希釈液体アンモニア;
(b)液体アンモニアと極性非プロトン溶媒
(c)脱水素触媒なしでの化学酸化剤;
(d)化学酸化剤なしでの脱水素触媒;または
(e)化学酸化剤と脱水素触媒
とを含む請求項1に記載の方法。 - 化学酸化剤が、硫黄、二酸化硫黄、酸素、セレニウム、2,3−ジクロロ−5,6−ジシアノ−p−ベンゾキノン、2,3,5,6−テトラクロロ−p−ベンゾキノン、塩化アルミニウム、酸化ヒ素、二酸化マンガン、フェリシアン化カリウム、ニトロベンゼン、塩素、臭素およびヨウ素からなる群から選択される請求項1に記載の方法。
- (a)脱水素触媒が、第VIII族の元素および該元素の塩から選択される少なくとも1つの金属または金属塩を含む均一系触媒を含むか、または
(b)脱水素触媒が、少なくとも1つの金属または金属塩と担体とを含み、ここで金属または金属塩が周期律表の第IVA族、第VA族、第VIA族、第VIIA族、第VIII族、第IB族および第IIB族の元素および該元素の塩から選択される不均一系触媒を含む
請求項3に記載の方法。 - 担体が、アルミナ、チタニア、酸化コバルト、ジルコニア、セリア、酸化モリブデン、酸化タングステン、シリカ、シリカライト、チタニア、ゼオライトまたは分子次元のチャンネルを有する拡大ネットワークを生成させるために酸素原子を通して互いに接合された四面体から構成された構造を有し、外面または内面上にSiOH基および/またはAlOH基を有するゼオタイプ材料、活性炭、コークスおよびチャコールからなる群から選択される請求項5に記載の方法。
- 極性非プロトン溶媒が、1,4−ジオキサン、テトラヒドロフラン、アセトン、アセトニトリル、ジメチルホルムアミド、ピリジン、および1,4−ジオキサンとピリジンとの混合物からなる群から選択される請求項3に記載の方法。
- 式(I)の化合物を、該化合物から化合物、オリゴマーまたはポリマーを製造するための反応に供する工程を更に含む請求項1に記載の方法。
- 製造されたポリマーが、ピリドビスイミダゾール−2,6−ジイル(2,5−ジヒドロキシ−p−フェニレン)ポリマーまたはポリ[(1,4−ジヒドロジイミダゾ[4,5−b:4’,5’−e]ピリジン−2,6−ジイル)(2,5−ジヒドロキシ−1,4−フェニレン)]ポリマーを含む請求項8に記載の方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US87657706P | 2006-12-21 | 2006-12-21 | |
PCT/US2007/025816 WO2008082509A2 (en) | 2006-12-21 | 2007-12-18 | Process for the synthesis of diaminopyridines from glutaronitriles |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2010513502A JP2010513502A (ja) | 2010-04-30 |
JP2010513502A5 true JP2010513502A5 (ja) | 2011-01-13 |
Family
ID=39582778
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2009542869A Abandoned JP2010513502A (ja) | 2006-12-21 | 2007-12-18 | グルタロニトリルからジアミノピリジンを合成する方法 |
Country Status (6)
Country | Link |
---|---|
US (1) | US8022167B2 (ja) |
EP (1) | EP2111393A2 (ja) |
JP (1) | JP2010513502A (ja) |
KR (1) | KR20090091348A (ja) |
CN (1) | CN101563325A (ja) |
WO (1) | WO2008082509A2 (ja) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010513496A (ja) * | 2006-12-21 | 2010-04-30 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | グルタルイミジンからジアミノピリジンを合成する方法 |
US7999057B2 (en) * | 2008-07-08 | 2011-08-16 | E. I. Du Pont De Nemours And Company | Gas-phase process for the synthesis of diaminopyridines from glutaronitriles |
KR20110099740A (ko) | 2008-12-18 | 2011-09-08 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 글루타로니트릴로부터 다이아미노피리딘의 합성을 위한 연속 액체상 방법 |
Family Cites Families (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2816879A (en) | 1951-11-15 | 1957-12-17 | Du Pont | Process for preparing polyureas utilizing immiscible phases |
GB1135462A (en) | 1966-05-13 | 1968-12-04 | Ici Ltd | Aromatic polyamides |
US3966652A (en) | 1974-11-11 | 1976-06-29 | International Harvester Company | Method of making foamed copolyimides and product obtained therefrom |
DE2519529B2 (de) * | 1975-05-02 | 1979-08-09 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur Herstellung von 3-Methylpyridin |
US4068050A (en) | 1976-05-17 | 1978-01-10 | Cpc International Inc. | Difunctional terminated macromolecular monomers and condensation copolymers produced therefrom |
US4051140A (en) | 1976-07-01 | 1977-09-27 | The Lummus Company | Preparation of pyridines and nicotinonitrile from piperidines |
EP0062264A3 (de) | 1981-03-31 | 1983-06-01 | Lonza Ag | Verfahren zur Herstellung von Amino-Pyridinen |
US4451642A (en) | 1981-05-21 | 1984-05-29 | E. I. Du Pont De Nemours And Company | Bis(aminoneopentyl) aromatics and polyamides derived therefrom |
FR2514772B1 (fr) | 1981-10-19 | 1985-09-06 | Inst Francais Du Petrole | Compositions reactives de polyimides thermostables presentant une solubilite elevee et leurs utilisations |
US5028713A (en) | 1983-12-08 | 1991-07-02 | The Standard Oil Company | Ammoxidation of methyl substituted heteroaromatics to make heteroaromatic nitriles |
US4603207A (en) | 1985-10-24 | 1986-07-29 | The Standard Oil Company | Conversion of a mixture of 3-methylpyridine and 3-methylpiperidine to 3-cyanopyridine |
US4876348A (en) | 1985-10-29 | 1989-10-24 | The Standard Oil Company | Process for making 3-cyanopyridine |
US4737571A (en) | 1986-01-17 | 1988-04-12 | E. I. Du Pont De Nemours And Company | Preparation of aromatic polyamide with solvent system comprising N-alkyl substituted amide and quaternary ammonium compound |
US5061784A (en) | 1990-08-06 | 1991-10-29 | Hoechst Celanese Corporation | Polymers prepared from 4,4'-bis(3,4-dicarboxyphenyl) hexafluoroisopropyl) diphenyl dianhydride |
US5066809A (en) | 1990-09-27 | 1991-11-19 | The Standard Oil Company | Preparation of 3-methylpyridine from 2-methylglutaronitrile |
ES2120042T3 (es) | 1993-04-28 | 1998-10-16 | Akzo Nobel Nv | Polimero de varilla rigida a base de piridobisimidazol. |
US5693227A (en) | 1994-11-17 | 1997-12-02 | Ionics, Incorporated | Catalyst mediated method of interfacial polymerization on a microporous support, and polymers, fibers, films and membranes made by such method |
NL1000360C2 (nl) * | 1995-05-15 | 1996-11-18 | Akzo Nobel Nv | Werkwijze ter bereiding van pyridine-2, 6-diamines |
US6118003A (en) | 1998-01-29 | 2000-09-12 | Reilly Industries, Inc. | Processes for producing 3-cyanopyridine from 2-methyl-1,5-pentanediamine |
EP1143048B1 (en) | 1999-10-21 | 2006-06-28 | Teijin Limited | Process for producing meta-aromatic polyamide fiber |
KR101337050B1 (ko) | 2005-03-28 | 2013-12-05 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 폴리아렌아졸 중합체의 제조 방법 |
-
2007
- 2007-12-18 KR KR1020097015149A patent/KR20090091348A/ko not_active Application Discontinuation
- 2007-12-18 US US12/519,592 patent/US8022167B2/en not_active Expired - Fee Related
- 2007-12-18 JP JP2009542869A patent/JP2010513502A/ja not_active Abandoned
- 2007-12-18 CN CNA2007800470753A patent/CN101563325A/zh active Pending
- 2007-12-18 EP EP07867802A patent/EP2111393A2/en not_active Withdrawn
- 2007-12-18 WO PCT/US2007/025816 patent/WO2008082509A2/en active Application Filing
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