DE3010791A1 - Verfahren zur herstellung von methylaminen - Google Patents
Verfahren zur herstellung von methylaminenInfo
- Publication number
- DE3010791A1 DE3010791A1 DE19803010791 DE3010791A DE3010791A1 DE 3010791 A1 DE3010791 A1 DE 3010791A1 DE 19803010791 DE19803010791 DE 19803010791 DE 3010791 A DE3010791 A DE 3010791A DE 3010791 A1 DE3010791 A1 DE 3010791A1
- Authority
- DE
- Germany
- Prior art keywords
- methanol
- catalyst
- dma
- ammonia
- tma
- 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.)
- Withdrawn
Links
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 title description 10
- 238000004519 manufacturing process Methods 0.000 title description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 90
- 239000003054 catalyst Substances 0.000 claims description 37
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 13
- 229910021529 ammonia Inorganic materials 0.000 claims description 12
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical class O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 claims description 10
- 150000003956 methylamines Chemical class 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000012808 vapor phase Substances 0.000 claims description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 28
- 229910052901 montmorillonite Inorganic materials 0.000 description 10
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 8
- 230000003197 catalytic effect Effects 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 239000004793 Polystyrene Substances 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- -1 aluminum silicates Chemical class 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229910052776 Thorium Inorganic materials 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical compound O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004523 catalytic cracking Methods 0.000 description 1
- 238000007036 catalytic synthesis reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- INPLXZPZQSLHBR-UHFFFAOYSA-N cobalt(2+);sulfide Chemical compound [S-2].[Co+2] INPLXZPZQSLHBR-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 229910000388 diammonium phosphate Inorganic materials 0.000 description 1
- 235000019838 diammonium phosphate Nutrition 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000010433 feldspar Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910000271 hectorite Inorganic materials 0.000 description 1
- KWLMIXQRALPRBC-UHFFFAOYSA-L hectorite Chemical compound [Li+].[OH-].[OH-].[Na+].[Mg+2].O1[Si]2([O-])O[Si]1([O-])O[Si]([O-])(O1)O[Si]1([O-])O2 KWLMIXQRALPRBC-UHFFFAOYSA-L 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 229910000273 nontronite Inorganic materials 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- KSOCVFUBQIXVDC-FMQUCBEESA-N p-azophenyltrimethylammonium Chemical compound C1=CC([N+](C)(C)C)=CC=C1\N=N\C1=CC=C([N+](C)(C)C)C=C1 KSOCVFUBQIXVDC-FMQUCBEESA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- FJOLTQXXWSRAIX-UHFFFAOYSA-K silver phosphate Chemical compound [Ag+].[Ag+].[Ag+].[O-]P([O-])([O-])=O FJOLTQXXWSRAIX-UHFFFAOYSA-K 0.000 description 1
- 229910000161 silver phosphate Inorganic materials 0.000 description 1
- 229940019931 silver phosphate Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- RUJLHPZAKCVICY-UHFFFAOYSA-J thorium(4+);disulfate Chemical compound [Th+4].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUJLHPZAKCVICY-UHFFFAOYSA-J 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/16—Clays or other mineral silicates
Landscapes
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7910300A GB2045232B (en) | 1979-03-23 | 1979-03-23 | Manufacture of methylamines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3010791A1 true DE3010791A1 (de) | 1980-10-02 |
Family
ID=10504093
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803010791 Withdrawn DE3010791A1 (de) | 1979-03-23 | 1980-03-20 | Verfahren zur herstellung von methylaminen |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS55129246A (OSRAM) |
| BE (1) | BE882332A (OSRAM) |
| BR (1) | BR8001725A (OSRAM) |
| CA (1) | CA1129888A (OSRAM) |
| DD (1) | DD149510A5 (OSRAM) |
| DE (1) | DE3010791A1 (OSRAM) |
| ES (1) | ES489771A0 (OSRAM) |
| FR (1) | FR2451909A1 (OSRAM) |
| GB (1) | GB2045232B (OSRAM) |
| IN (1) | IN151294B (OSRAM) |
| IT (1) | IT8048227A0 (OSRAM) |
| NL (1) | NL8001612A (OSRAM) |
| ZA (1) | ZA801658B (OSRAM) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4458092A (en) * | 1982-01-29 | 1984-07-03 | Air Products And Chemicals, Inc. | Highly active catalysts for methanol amination |
| DE3564102D1 (en) * | 1984-11-07 | 1988-09-08 | Air Prod & Chem | Amines via the amination of alkanols using dealuminated zeolites |
-
1979
- 1979-03-23 GB GB7910300A patent/GB2045232B/en not_active Expired
-
1980
- 1980-03-18 NL NL8001612A patent/NL8001612A/nl not_active Application Discontinuation
- 1980-03-20 DE DE19803010791 patent/DE3010791A1/de not_active Withdrawn
- 1980-03-20 BE BE1/9753A patent/BE882332A/fr not_active IP Right Cessation
- 1980-03-20 DD DD80219796A patent/DD149510A5/de unknown
- 1980-03-20 IN IN319/CAL/80A patent/IN151294B/en unknown
- 1980-03-21 BR BR8001725A patent/BR8001725A/pt unknown
- 1980-03-21 FR FR8006451A patent/FR2451909A1/fr not_active Withdrawn
- 1980-03-21 ZA ZA00801658A patent/ZA801658B/xx unknown
- 1980-03-21 ES ES489771A patent/ES489771A0/es active Granted
- 1980-03-21 CA CA348,201A patent/CA1129888A/en not_active Expired
- 1980-03-21 IT IT8048227A patent/IT8048227A0/it unknown
- 1980-03-22 JP JP3683480A patent/JPS55129246A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IN151294B (OSRAM) | 1983-03-26 |
| ZA801658B (en) | 1981-03-25 |
| NL8001612A (nl) | 1980-09-25 |
| ES8103017A1 (es) | 1981-02-16 |
| CA1129888A (en) | 1982-08-17 |
| BE882332A (fr) | 1980-09-22 |
| FR2451909A1 (fr) | 1980-10-17 |
| DD149510A5 (de) | 1981-07-15 |
| BR8001725A (pt) | 1980-11-18 |
| JPS55129246A (en) | 1980-10-06 |
| IT8048227A0 (it) | 1980-03-21 |
| GB2045232A (en) | 1980-10-29 |
| ES489771A0 (es) | 1981-02-16 |
| GB2045232B (en) | 1983-03-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0132736B1 (de) | Verfahren zur Herstellung von Aminen | |
| EP0170182B1 (de) | Verfahren zur Gewinnung von 2-Butenen aus 1-Buten und gegebenenfalls 2-Butene enthaltenden C4-Kohlenwasserstoffgemischen | |
| DE2655891A1 (de) | Katalytisches verfahren zum oxidieren von propanol-(1) | |
| EP0072920B1 (de) | Verfahren zur Herstellung von Olefinen aus Methanol und/oder Dimethylether | |
| EP0090283B1 (de) | Verfahren zur Herstellung von Olefinen aus Methanol/Dimethylether | |
| EP0263464A2 (de) | Verfahren zur Herstellung von substituierten Pyridinen | |
| EP0162385B1 (de) | Verfahren zur Herstellung von Dienen durch Dehydratisierung von Aldehyden | |
| DE2846813A1 (de) | Verfahren zur herstellung von 1,4-diazabicyclo-(2,2,2)-octan | |
| DE3490097T1 (de) | Bindemittelfreie Zeolithkatalysatoren, Verfahren zu ihrer Herstellung und katalytische Reaktion mit ihnen | |
| EP0249976B1 (de) | Verfahren zur Herstellung von Carbonsäuren | |
| EP0266689A2 (de) | Verfahren zur Herstellung von 4-Pentensäureestern | |
| EP0125415A1 (de) | Verfahren zur Herstellung von Pyrrolen | |
| DE3010791A1 (de) | Verfahren zur herstellung von methylaminen | |
| EP0352505B1 (de) | Verfahren zur Herstellung von Thymol | |
| DE3634247C1 (de) | Verfahren zur Herstellung von Aminen | |
| EP0416279A1 (de) | Verfahren zur Herstellung von Kresolisomergemischen mit einem Molverhältnis von para- zu meta-Kresol von mindestens 0,6:1 bis 10:1 | |
| DE2617219C3 (de) | Verfahren zum Cracken von Dicyclohexylbenzolen | |
| EP0016406A1 (de) | Verfahren zur Herstellung von Olefinen aus Rohmethanol | |
| EP0162387B1 (de) | Verfahren zur Herstellung von Ketonen durch Isomerisierung von Aldehyden | |
| EP0499799A1 (de) | Katalysator zur Umwandlung technischer C8-Aromatenfraktionen | |
| EP0844991A1 (de) | Verfahren zur herstellung von aminen aus olefinen an bor-beta-zeolithen | |
| EP0132737B1 (de) | Verfahren zur Isomerisierung von Diacyloxy-butenen | |
| DE3015803C2 (de) | Verfahren zur Herstellung von 3,5-Dimethylphenol aus Aceton | |
| EP0219042B1 (de) | Verfahren zur Herstellung von Dienen durch Dehydratisierung von Aldehyden | |
| DE102019106698B4 (de) | Katalytische Herstellung von Butadien |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |