JPS5824564A - ３−シアンピリジンの取得法 - Google Patents
３−シアンピリジンの取得法Info
- Publication number
- JPS5824564A JPS5824564A JP57124535A JP12453582A JPS5824564A JP S5824564 A JPS5824564 A JP S5824564A JP 57124535 A JP57124535 A JP 57124535A JP 12453582 A JP12453582 A JP 12453582A JP S5824564 A JPS5824564 A JP S5824564A
- Authority
- JP
- Japan
- Prior art keywords
- ammonium
- gas
- water
- cyanpyridine
- carbon dioxide
- 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
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 title claims description 17
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 claims abstract description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 31
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000001301 oxygen Substances 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 7
- 239000007789 gas Substances 0.000 claims description 50
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 47
- 239000000203 mixture Substances 0.000 claims description 26
- 239000007864 aqueous solution Substances 0.000 claims description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 239000008246 gaseous mixture Substances 0.000 abstract 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 49
- 239000001569 carbon dioxide Substances 0.000 description 24
- 229910002092 carbon dioxide Inorganic materials 0.000 description 24
- 238000004140 cleaning Methods 0.000 description 24
- 239000007788 liquid Substances 0.000 description 19
- 238000003795 desorption Methods 0.000 description 13
- 239000000243 solution Substances 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000002912 waste gas Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000001099 ammonium carbonate Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 2
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 description 1
- 235000004936 Bromus mango Nutrition 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 240000007228 Mangifera indica Species 0.000 description 1
- 235000014826 Mangifera indica Nutrition 0.000 description 1
- 235000009184 Spondias indica Nutrition 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- -1 inter alia Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Treating Waste Gases (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813128956 DE3128956A1 (de) | 1981-07-22 | 1981-07-22 | Verfahren zur gewinnung von 3-cyanpyridin |
| DE3128956.8 | 1981-07-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5824564A true JPS5824564A (ja) | 1983-02-14 |
| JPH0414108B2 JPH0414108B2 (en, 2012) | 1992-03-11 |
Family
ID=6137480
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57124535A Granted JPS5824564A (ja) | 1981-07-22 | 1982-07-19 | ３−シアンピリジンの取得法 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4482719A (en, 2012) |
| EP (1) | EP0070395B1 (en, 2012) |
| JP (1) | JPS5824564A (en, 2012) |
| AT (1) | ATE22075T1 (en, 2012) |
| AU (1) | AU557923B2 (en, 2012) |
| BR (1) | BR8204175A (en, 2012) |
| CA (1) | CA1169864A (en, 2012) |
| DE (2) | DE3128956A1 (en, 2012) |
| ES (1) | ES8500237A1 (en, 2012) |
| IL (1) | IL65844A (en, 2012) |
| IN (1) | IN155430B (en, 2012) |
| ZA (1) | ZA823553B (en, 2012) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63126409U (en, 2012) * | 1987-02-09 | 1988-08-18 | ||
| JP2001348370A (ja) * | 2000-04-04 | 2001-12-18 | Mitsubishi Gas Chem Co Inc | ニトリル化合物の製造方法 |
| JP2001349441A (ja) * | 2000-04-10 | 2001-12-21 | Hoerbiger Kompressortechnik Service Gmbh | シールリングコンビネーション |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| ES2026964T3 (es) * | 1987-05-12 | 1992-05-16 | Nippon Shokubai Kagaku Kogyo Co., Ltd | Procedimiento para producir nitrilos aromaticos o heterociclicos. |
| DE19504283A1 (de) * | 1995-02-09 | 1996-08-14 | Degussa | Verfahren zur Herstellung von Cyanopyridinen und dafür geeignete Katalysatoren |
| DE19647527C1 (de) * | 1996-11-16 | 1998-03-12 | Degussa | Verfahren zur Herstellung von Cyanoverbindungen durch Ammonoxidation |
| DE10335454A1 (de) * | 2003-08-02 | 2005-02-24 | Reilly Industries, Inc., Indianapolis | Verfahren zur Herstellung von Cyanopyridinen und dafür geeignete Katalysatoren |
| EP2319833A1 (en) | 2009-10-16 | 2011-05-11 | Lonza Ltd. | Methods and devices for the production of aqueous solutions of cyanopyridines |
| CN103467370B (zh) * | 2013-09-12 | 2015-07-22 | 南通天泽化工有限公司 | 氰基吡啶及其衍生物的合成方法 |
| CN104356061A (zh) * | 2014-10-23 | 2015-02-18 | 河南省科学院高新技术研究中心 | 一种2-氰基吡啶高效吸收方法 |
| CN112547042A (zh) * | 2020-12-10 | 2021-03-26 | 中触媒新材料股份有限公司 | 一种2-氰基吡啶催化剂的制备方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5083374A (en, 2012) * | 1973-11-15 | 1975-07-05 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE862011C (de) * | 1949-06-21 | 1953-01-08 | Nepera Chemical Co Inc | Verfahren zur Herstellung von Pyridinabkoemmlingen |
| GB777746A (en) * | 1954-12-09 | 1957-06-26 | Distillers Co Yeast Ltd | Process for the production of cyanopyridines |
| US2861999A (en) * | 1956-03-27 | 1958-11-25 | Allied Chem | Production of cyanopyridines |
| DE2039497C3 (de) * | 1970-08-08 | 1974-01-17 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt | Verfahren zur Herstellung von Antimon enthaltenden Katalysatoren und Verwendung der Katalysatoren für die Herstellung von aromatischen und heteroaromatischen Nitrilen |
| CH582151A5 (en, 2012) * | 1973-08-10 | 1976-11-30 | Lonza Ag |
-
1981
- 1981-07-22 DE DE19813128956 patent/DE3128956A1/de not_active Withdrawn
-
1982
- 1982-05-13 ES ES512147A patent/ES8500237A1/es not_active Expired
- 1982-05-21 ZA ZA823553A patent/ZA823553B/xx unknown
- 1982-05-21 IL IL65844A patent/IL65844A/xx unknown
- 1982-06-05 IN IN647/CAL/82A patent/IN155430B/en unknown
- 1982-06-18 EP EP82105359A patent/EP0070395B1/de not_active Expired
- 1982-06-18 AT AT82105359T patent/ATE22075T1/de active
- 1982-06-18 DE DE8282105359T patent/DE3273159D1/de not_active Expired
- 1982-06-23 US US06/391,434 patent/US4482719A/en not_active Expired - Lifetime
- 1982-07-16 AU AU86086/82A patent/AU557923B2/en not_active Ceased
- 1982-07-19 BR BR8204175A patent/BR8204175A/pt unknown
- 1982-07-19 JP JP57124535A patent/JPS5824564A/ja active Granted
- 1982-07-21 CA CA000407691A patent/CA1169864A/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5083374A (en, 2012) * | 1973-11-15 | 1975-07-05 |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63126409U (en, 2012) * | 1987-02-09 | 1988-08-18 | ||
| JP2001348370A (ja) * | 2000-04-04 | 2001-12-18 | Mitsubishi Gas Chem Co Inc | ニトリル化合物の製造方法 |
| JP2001349441A (ja) * | 2000-04-10 | 2001-12-21 | Hoerbiger Kompressortechnik Service Gmbh | シールリングコンビネーション |
Also Published As
| Publication number | Publication date |
|---|---|
| IN155430B (en, 2012) | 1985-01-26 |
| ES512147A0 (es) | 1984-10-01 |
| DE3128956A1 (de) | 1983-02-10 |
| IL65844A0 (en) | 1982-08-31 |
| IL65844A (en) | 1985-07-31 |
| EP0070395A2 (de) | 1983-01-26 |
| EP0070395A3 (en) | 1983-07-20 |
| CA1169864A (en) | 1984-06-26 |
| BR8204175A (pt) | 1983-07-12 |
| ES8500237A1 (es) | 1984-10-01 |
| US4482719A (en) | 1984-11-13 |
| ATE22075T1 (de) | 1986-09-15 |
| DE3273159D1 (en) | 1986-10-16 |
| ZA823553B (en) | 1983-03-30 |
| AU8608682A (en) | 1983-01-27 |
| JPH0414108B2 (en, 2012) | 1992-03-11 |
| AU557923B2 (en) | 1987-01-15 |
| EP0070395B1 (de) | 1986-09-10 |
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