CN100540140C - Be used to produce the Catalysts and its preparation method of pyridine base - Google Patents
Be used to produce the Catalysts and its preparation method of pyridine base Download PDFInfo
- Publication number
- CN100540140C CN100540140C CNB2007100213474A CN200710021347A CN100540140C CN 100540140 C CN100540140 C CN 100540140C CN B2007100213474 A CNB2007100213474 A CN B2007100213474A CN 200710021347 A CN200710021347 A CN 200710021347A CN 100540140 C CN100540140 C CN 100540140C
- Authority
- CN
- China
- Prior art keywords
- catalyst
- molecular sieve
- zsm
- pyridine
- bismuth
- 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.)
- Expired - Fee Related
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims abstract description 140
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title claims abstract description 70
- 239000003054 catalyst Substances 0.000 title claims abstract description 64
- 238000002360 preparation method Methods 0.000 title abstract description 11
- 239000002808 molecular sieve Substances 0.000 claims abstract description 43
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims abstract description 43
- 238000000034 method Methods 0.000 claims abstract description 29
- 229910052797 bismuth Inorganic materials 0.000 claims abstract description 24
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000000203 mixture Substances 0.000 claims abstract description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 28
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 26
- 239000000377 silicon dioxide Substances 0.000 claims description 14
- 239000011230 binding agent Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 229910001868 water Inorganic materials 0.000 claims description 6
- 150000001621 bismuth Chemical class 0.000 claims description 4
- 230000001105 regulatory effect Effects 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 238000001802 infusion Methods 0.000 claims description 2
- 238000009736 wetting Methods 0.000 claims description 2
- 238000009835 boiling Methods 0.000 abstract description 21
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 abstract description 15
- 239000006227 byproduct Substances 0.000 abstract description 14
- 238000011084 recovery Methods 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 description 29
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 22
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 16
- 229910021529 ammonia Inorganic materials 0.000 description 15
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- 239000002994 raw material Substances 0.000 description 11
- 239000007789 gas Substances 0.000 description 9
- 150000001299 aldehydes Chemical class 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 238000011049 filling Methods 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 239000012495 reaction gas Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- PPNKDDZCLDMRHS-UHFFFAOYSA-N dinitrooxybismuthanyl nitrate Chemical class [Bi+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PPNKDDZCLDMRHS-UHFFFAOYSA-N 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical class CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- -1 alkyl pyridines Chemical class 0.000 description 2
- 150000004645 aluminates Chemical class 0.000 description 2
- 229910021417 amorphous silicon Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 239000000110 cooling liquid Substances 0.000 description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 238000009834 vaporization Methods 0.000 description 2
- 230000008016 vaporization Effects 0.000 description 2
- AOKYJAAYDKAMJZ-UHFFFAOYSA-N 2-methylpyridine;pyridine Chemical compound C1=CC=NC=C1.CC1=CC=CC=N1 AOKYJAAYDKAMJZ-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 238000005653 Chichibabin synthesis reaction Methods 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000004939 coking Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- RXPAJWPEYBDXOG-UHFFFAOYSA-N hydron;methyl 4-methoxypyridine-2-carboxylate;chloride Chemical compound Cl.COC(=O)C1=CC(OC)=CC=N1 RXPAJWPEYBDXOG-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000003746 solid phase reaction Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
- Catalysts (AREA)
Abstract
Description
Reaction temperature (℃) | Reaction gas air speed (h -1) | Formaldehyde: acetaldehyde: ammonia mol ratio | The pyridine molar yield | The total molar yield of pyridine and picoline | High boiling point by-products produced molar yield |
450 | 800 | 1∶1∶3 | 64 | 88 | 10 |
Reaction temperature (℃) | Reaction gas air speed (h -1) | Formaldehyde: acetaldehyde: ammonia mol ratio | The pyridine molar yield | The total molar yield of pyridine and picoline | High boiling point by-products produced molar yield |
450 | 800 | 1∶1∶3 | 62 | 86 | 12 |
Reaction temperature (℃) | Reaction gas air speed (h -1) | Formaldehyde: acetaldehyde: ammonia mol ratio | The pyridine molar yield | The total molar yield of pyridine and picoline | High boiling point by-products produced molar yield |
450 | 800 | 1∶1∶3 | 59 | 87 | 11 |
Reaction temperature (℃) | Reaction gas air speed (h -1) | Formaldehyde: acetaldehyde: ammonia mol ratio | The pyridine molar yield | The total molar yield of pyridine and picoline | High boiling point by-products produced molar yield |
450 | 800 | 1∶1∶3 | 51 | 76 | 22 |
Claims (4)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB2007100213474A CN100540140C (en) | 2007-04-09 | 2007-04-09 | Be used to produce the Catalysts and its preparation method of pyridine base |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB2007100213474A CN100540140C (en) | 2007-04-09 | 2007-04-09 | Be used to produce the Catalysts and its preparation method of pyridine base |
Publications (2)
Publication Number | Publication Date |
---|---|
CN101032693A CN101032693A (en) | 2007-09-12 |
CN100540140C true CN100540140C (en) | 2009-09-16 |
Family
ID=38729551
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CNB2007100213474A Expired - Fee Related CN100540140C (en) | 2007-04-09 | 2007-04-09 | Be used to produce the Catalysts and its preparation method of pyridine base |
Country Status (1)
Country | Link |
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CN (1) | CN100540140C (en) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100577286C (en) * | 2009-02-18 | 2010-01-06 | 中国科学院大连化学物理研究所 | Titanium-based catalyst for synthesizing pyridine base with formaldehyde, acetaldehyde and ammonia, as well as preparation method thereof |
CN108816275B (en) * | 2018-04-19 | 2021-02-05 | 南京红太阳生物化学有限责任公司 | Catalyst for preparing pyridine base from synthesis gas, preparation method and application |
CN109174168B (en) * | 2018-10-26 | 2021-06-29 | 南京红太阳生物化学有限责任公司 | Catalyst for preparing 2-methylpyridine by pyridine alkylation, preparation method and application |
CN111468177B (en) * | 2020-05-15 | 2022-04-15 | 山东师范大学 | Molecular sieve catalyst for preparing pyridine base and preparation method and application thereof |
CN111468178B (en) * | 2020-05-18 | 2022-07-12 | 山东师范大学 | Metal modified ZSM-5 molecular sieve catalyst and preparation method and application thereof |
CN113385220A (en) * | 2021-07-21 | 2021-09-14 | 西南化工研究设计院有限公司 | Preparation method of catalyst for preparing pyridine and picoline by methanol and ammonia water in one step |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1287316A (en) * | 1969-11-08 | 1972-08-31 | Koei Chemical Co | Production of pyridine bases and catalyst therefor |
-
2007
- 2007-04-09 CN CNB2007100213474A patent/CN100540140C/en not_active Expired - Fee Related
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1287316A (en) * | 1969-11-08 | 1972-08-31 | Koei Chemical Co | Production of pyridine bases and catalyst therefor |
Also Published As
Publication number | Publication date |
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CN101032693A (en) | 2007-09-12 |
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Address after: 211300 Pagoda Road 269, Gaochun County, Jiangsu, Nanjing Patentee after: Nanjing No.1 Pesticide Group Co.,Ltd. Address before: 211300 Pagoda Road 269, Gaochun County, Jiangsu, Nanjing Patentee before: NANJING NO 1 PESTICIDE Co.,Ltd. |
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Effective date of registration: 20111207 Address after: 243100 Dangtu Economic Development Zone in Anhui Patentee after: ANHUI COSTAR BIOCHEMICAL Co.,Ltd. Address before: 210047 Nanjing Chemical Industrial Park, Jiangsu aromatic South Road, No. 168 Patentee before: NANJING REDSUN BIOCHEMISTRY Co.,Ltd. |
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Assignee: NANJING REDSUN BIOCHEMISTRY Co.,Ltd. Assignor: ANHUI COSTAR BIOCHEMICAL Co.,Ltd. Contract record no.: 2012320000408 Denomination of invention: Catalyst for producing pyridine alkali and its preparation method Granted publication date: 20090916 License type: Exclusive License Open date: 20070912 Record date: 20120406 |
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