CA2126834C - Preparation de methanamines a l'aide de chabazites possedant des proprietes de selectivite geometrique - Google Patents
Preparation de methanamines a l'aide de chabazites possedant des proprietes de selectivite geometriqueInfo
- Publication number
- CA2126834C CA2126834C CA002126834A CA2126834A CA2126834C CA 2126834 C CA2126834 C CA 2126834C CA 002126834 A CA002126834 A CA 002126834A CA 2126834 A CA2126834 A CA 2126834A CA 2126834 C CA2126834 C CA 2126834C
- Authority
- CA
- Canada
- Prior art keywords
- catalyst
- reaction
- chabazite
- methanol
- ssi
- 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
Links
- 150000003956 methylamines Chemical class 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 139
- 239000003054 catalyst Substances 0.000 claims abstract description 105
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims abstract description 96
- 229910052676 chabazite Inorganic materials 0.000 claims abstract description 82
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims abstract description 81
- UNYSKUBLZGJSLV-UHFFFAOYSA-L calcium;1,3,5,2,4,6$l^{2}-trioxadisilaluminane 2,4-dioxide;dihydroxide;hexahydrate Chemical compound O.O.O.O.O.O.[OH-].[OH-].[Ca+2].O=[Si]1O[Al]O[Si](=O)O1.O=[Si]1O[Al]O[Si](=O)O1 UNYSKUBLZGJSLV-UHFFFAOYSA-L 0.000 claims abstract description 67
- 238000006243 chemical reaction Methods 0.000 claims abstract description 64
- 238000000034 method Methods 0.000 claims abstract description 62
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 54
- 230000008569 process Effects 0.000 claims abstract description 44
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims abstract description 28
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 24
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 20
- 238000001179 sorption measurement Methods 0.000 claims abstract description 19
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 6
- 238000002407 reforming Methods 0.000 claims abstract description 5
- 238000001833 catalytic reforming Methods 0.000 claims abstract 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 41
- 229910052708 sodium Inorganic materials 0.000 claims description 26
- 229910052700 potassium Inorganic materials 0.000 claims description 21
- 150000001768 cations Chemical class 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 4
- 229910052792 caesium Inorganic materials 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000007789 gas Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 230000006872 improvement Effects 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 229910052701 rubidium Inorganic materials 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 229910052733 gallium Inorganic materials 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- 229910052712 strontium Inorganic materials 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 230000002708 enhancing effect Effects 0.000 claims 1
- 239000010457 zeolite Substances 0.000 abstract description 27
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 abstract description 22
- 229910021536 Zeolite Inorganic materials 0.000 abstract description 18
- 230000000694 effects Effects 0.000 abstract description 17
- 150000004656 dimethylamines Chemical class 0.000 abstract 1
- 239000011734 sodium Substances 0.000 description 31
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 28
- 239000000047 product Substances 0.000 description 24
- 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 13
- 238000005342 ion exchange Methods 0.000 description 13
- 229910052681 coesite Inorganic materials 0.000 description 12
- 229910052906 cristobalite Inorganic materials 0.000 description 12
- 239000000377 silicon dioxide Substances 0.000 description 12
- 239000010454 slate Substances 0.000 description 12
- 229910052682 stishovite Inorganic materials 0.000 description 12
- 229910052905 tridymite Inorganic materials 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000005576 amination reaction Methods 0.000 description 11
- 239000008367 deionised water Substances 0.000 description 11
- 229910021641 deionized water Inorganic materials 0.000 description 11
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 11
- 235000012239 silicon dioxide Nutrition 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 10
- 239000011591 potassium Substances 0.000 description 10
- 238000009826 distribution Methods 0.000 description 8
- 238000000921 elemental analysis Methods 0.000 description 8
- WSWCOQWTEOXDQX-MQQKCMAXSA-M (E,E)-sorbate Chemical compound C\C=C\C=C\C([O-])=O WSWCOQWTEOXDQX-MQQKCMAXSA-M 0.000 description 7
- 238000001354 calcination Methods 0.000 description 7
- 239000011148 porous material Substances 0.000 description 7
- 229940075554 sorbate Drugs 0.000 description 7
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 229910052675 erionite Inorganic materials 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 5
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Inorganic materials [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- -1 al Ullli na Inorganic materials 0.000 description 3
- 229910000323 aluminium silicate Inorganic materials 0.000 description 3
- 238000005341 cation exchange Methods 0.000 description 3
- 230000029087 digestion Effects 0.000 description 3
- 229910052680 mordenite Inorganic materials 0.000 description 3
- 241001507939 Cormus domestica Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- JYIBXUUINYLWLR-UHFFFAOYSA-N aluminum;calcium;potassium;silicon;sodium;trihydrate Chemical compound O.O.O.[Na].[Al].[Si].[K].[Ca] JYIBXUUINYLWLR-UHFFFAOYSA-N 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 229910001603 clinoptilolite Inorganic materials 0.000 description 2
- 239000008119 colloidal silica Substances 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 2
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 229910001868 water Inorganic materials 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 241000512668 Eunectes Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920002274 Nalgene Polymers 0.000 description 1
- 235000007889 Osmunda cinnamomea Nutrition 0.000 description 1
- 244000239204 Plantago lanceolata Species 0.000 description 1
- 235000010503 Plantago lanceolata Nutrition 0.000 description 1
- 241001486234 Sciota Species 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000011959 amorphous silica alumina Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004939 coking Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 210000005053 lamin Anatomy 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- NCYVXEGFNDZQCU-UHFFFAOYSA-N nikethamide Chemical compound CCN(CC)C(=O)C1=CC=CN=C1 NCYVXEGFNDZQCU-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Méthode pour l'obtention d'une distribution non équilibrée de méthylamines par réaction catalytique du méthanol et (ou) d'oxyde de diméthyle avec de l'ammoniac, et par reformage catalytique d'une alimentation à base de méthylamine. L'un des procédés donne un produit de réaction enrichi en mono- et diméthylamines, et pauvre en triméthylamines, pour un taux de conversion élevé du méthanol ou de l'oxyde de diméthyle. Une variante du procédé permet le reformage d'une alimentation renfermant des méthylamines, et facultativement de l'ammoniac, sur un catalyseur. La clé pour obtenir cette faible sélectivité en TMA à haut taux de conversion est l'utilisation d'une zéolite microporeuse, de préférence la chabazite, catalyseur possédant un indice de sélectivité géométrique (ISG) de moins de 3 environ, un indice de sélectivité de forme (SSI) de plus de 5 environ, et une capacité de sorption pour 1-PrOH d'au moins 0,5 mmole/an.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8649793A | 1993-07-01 | 1993-07-01 | |
| US08/086497 | 1993-07-01 | ||
| US08/253,872 US5399769A (en) | 1993-07-01 | 1994-06-03 | Preparation of methylamines using shape selective chabazites |
| US08/253,872 | 1994-06-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2126834A1 CA2126834A1 (fr) | 1995-01-02 |
| CA2126834C true CA2126834C (fr) | 1997-12-09 |
Family
ID=26774813
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002126834A Expired - Fee Related CA2126834C (fr) | 1993-07-01 | 1994-06-27 | Preparation de methanamines a l'aide de chabazites possedant des proprietes de selectivite geometrique |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JP2856383B2 (fr) |
| CN (2) | CN1040531C (fr) |
| CA (1) | CA2126834C (fr) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4508654B2 (ja) * | 2002-03-15 | 2010-07-21 | エクソンモービル・ケミカル・パテンツ・インク | 高シリカシャバサイト、その合成及びオキシジェネート類のオレフィン類への変換におけるその使用 |
| MXPA06014444A (es) * | 2004-06-18 | 2007-03-21 | Basf Ag | Proceso para la sintesis continua de metilaminas. |
| CN100504641C (zh) * | 2004-09-30 | 2009-06-24 | 佳能株式会社 | 成像装置和检测显影剂剩余量的方法 |
| WO2016164027A1 (fr) * | 2015-04-09 | 2016-10-13 | Hong-Xin Li | Matériau cristallin microporeux stabilisé, procédé de fabrication de celui-ci et utilisation pour la réduction catalytique sélective de nox |
| WO2018221194A1 (fr) * | 2017-05-29 | 2018-12-06 | エヌ・イーケムキャット株式会社 | Aluminosilicate cha et son procédé de production, et catalyseur de purification de gaz d'échappement, appareil de purification de gaz d'échappement et procédé de purification de gaz d'échappement l'utilisant |
| JPWO2023063244A1 (fr) * | 2021-10-11 | 2023-04-20 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4398041A (en) * | 1982-01-29 | 1983-08-09 | Air Products And Chemicals, Inc. | Process for manufacturing alkylamines |
| DE3577434D1 (en) * | 1984-11-16 | 1990-06-07 | Du Pont | Dimethylaminsynthesekatalysator. |
-
1994
- 1994-06-27 CA CA002126834A patent/CA2126834C/fr not_active Expired - Fee Related
- 1994-06-30 JP JP6149398A patent/JP2856383B2/ja not_active Expired - Fee Related
- 1994-07-01 CN CN94108130A patent/CN1040531C/zh not_active Expired - Fee Related
-
1997
- 1997-05-22 CN CN97113436A patent/CN1122017C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH07145113A (ja) | 1995-06-06 |
| CN1173486A (zh) | 1998-02-18 |
| CN1040531C (zh) | 1998-11-04 |
| JP2856383B2 (ja) | 1999-02-10 |
| CN1122017C (zh) | 2003-09-24 |
| CA2126834A1 (fr) | 1995-01-02 |
| CN1102827A (zh) | 1995-05-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed | ||
| MKLA | Lapsed |
Effective date: 20050627 |