CA1246613A - Zeolite h-zk-5 as catalyst for conversion of methanol and ammonia to dimethylamine - Google Patents

Zeolite h-zk-5 as catalyst for conversion of methanol and ammonia to dimethylamine

Info

Publication number: CA1246613A
Authority: CA; Canada
Prior art keywords: zeolite; process according; catalyst; ion; methanol
Prior art date: 1984-11-16
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

Application number

CA000495367A

Other languages

English (en)

French (fr)

Inventor

Thurman E. Gier

Robert D. Shannon

George C. Sonnichsen

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

EIDP Inc

Original Assignee

EI Du Pont de Nemours and Co

Priority date (The priority date 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 date listed.)

1984-11-16

Filing date

1985-11-14

Publication date

1988-12-13

1985-11-14 Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co

1988-12-13 Application granted granted Critical

1988-12-13 Publication of CA1246613A publication Critical patent/CA1246613A/en

Status Expired legal-status Critical Current

Links

239000010457 zeolite Substances 0.000 claims abstract description 81
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 78
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract description 77
229910021536 Zeolite Inorganic materials 0.000 claims abstract description 75
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 50
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims abstract description 47
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims abstract description 40
238000000034 method Methods 0.000 claims abstract description 28
239000003054 catalyst Substances 0.000 claims abstract description 25
229910021529 ammonia Inorganic materials 0.000 claims abstract description 22
230000002378 acidificating effect Effects 0.000 claims abstract description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 6
229910052799 carbon Inorganic materials 0.000 claims abstract description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 3
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
238000001354 calcination Methods 0.000 claims description 17
239000000376 reactant Substances 0.000 claims description 12
230000003197 catalytic effect Effects 0.000 claims description 5
238000006243 chemical reaction Methods 0.000 abstract description 10
150000002500 ions Chemical class 0.000 description 47
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 22
239000011148 porous material Substances 0.000 description 13
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 7
239000011575 calcium Substances 0.000 description 7
238000001179 sorption measurement Methods 0.000 description 7
230000000052 comparative effect Effects 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 6
101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
150000001768 cations Chemical class 0.000 description 5
229910052675 erionite Inorganic materials 0.000 description 5
229910001657 ferrierite group Inorganic materials 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
239000000463 material Substances 0.000 description 4
239000000523 sample Substances 0.000 description 4
101100285518 Drosophila melanogaster how gene Proteins 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
229910052782 aluminium Inorganic materials 0.000 description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
229910052791 calcium Inorganic materials 0.000 description 3
229910052680 mordenite Inorganic materials 0.000 description 3
229910052712 strontium Inorganic materials 0.000 description 3
239000000126 substance Substances 0.000 description 3
CBQYNPHHHJTCJS-UHFFFAOYSA-N Alline Chemical compound C1=CC=C2C3(O)CCN(C)C3NC2=C1 CBQYNPHHHJTCJS-UHFFFAOYSA-N 0.000 description 2
229910052684 Cerium Inorganic materials 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
241000282326 Felis catus Species 0.000 description 2
229910002651 NO3 Inorganic materials 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
229910000323 aluminium silicate Inorganic materials 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
229910052788 barium Inorganic materials 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
230000002844 continuous effect Effects 0.000 description 2
230000002596 correlated effect Effects 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
AYOOGWWGECJQPI-NSHDSACASA-N n-[(1s)-1-(5-fluoropyrimidin-2-yl)ethyl]-3-(3-propan-2-yloxy-1h-pyrazol-5-yl)imidazo[4,5-b]pyridin-5-amine Chemical compound N1C(OC(C)C)=CC(N2C3=NC(N[C@@H](C)C=4N=CC(F)=CN=4)=CC=C3N=C2)=N1 AYOOGWWGECJQPI-NSHDSACASA-N 0.000 description 2
229910000069 nitrogen hydride Inorganic materials 0.000 description 2
229940099990 ogen Drugs 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
WSWCOQWTEOXDQX-MQQKCMAXSA-M (E,E)-sorbate Chemical compound C\C=C\C=C\C([O-])=O WSWCOQWTEOXDQX-MQQKCMAXSA-M 0.000 description 1
BSFODEXXVBBYOC-UHFFFAOYSA-N 8-[4-(dimethylamino)butan-2-ylamino]quinolin-6-ol Chemical compound C1=CN=C2C(NC(CCN(C)C)C)=CC(O)=CC2=C1 BSFODEXXVBBYOC-UHFFFAOYSA-N 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical group CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
MVVPIAAVGAWJNQ-DOFZRALJSA-N Arachidonoyl dopamine Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCC1=CC=C(O)C(O)=C1 MVVPIAAVGAWJNQ-DOFZRALJSA-N 0.000 description 1
101150039033 Eci2 gene Proteins 0.000 description 1
241001643623 Enteles Species 0.000 description 1
206010015137 Eructation Diseases 0.000 description 1
UOACKFBJUYNSLK-XRKIENNPSA-N Estradiol Cypionate Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H](C4=CC=C(O)C=C4CC3)CC[C@@]21C)C(=O)CCC1CCCC1 UOACKFBJUYNSLK-XRKIENNPSA-N 0.000 description 1
241001527806 Iti Species 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N L-glucitol Chemical compound OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
241000283986 Lepus Species 0.000 description 1
241000353097 Molva molva Species 0.000 description 1
241001072332 Monia Species 0.000 description 1
241001387976 Pera Species 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
101100463797 Rattus norvegicus Pgrmc1 gene Proteins 0.000 description 1
101100408472 Rhodocybe pseudopiperita ple6 gene Proteins 0.000 description 1
208000035389 Ring chromosome 6 syndrome Diseases 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
241000876472 Umma Species 0.000 description 1
229910052770 Uranium Inorganic materials 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
HUMHYXGDUOGHTG-HEZXSMHISA-N alpha-D-GalpNAc-(1->3)-[alpha-L-Fucp-(1->2)]-D-Galp Chemical compound O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](O[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](O)[C@@H](CO)OC1O HUMHYXGDUOGHTG-HEZXSMHISA-N 0.000 description 1
RREGISFBPQOLTM-UHFFFAOYSA-N alumane;trihydrate Chemical class O.O.O.[AlH3] RREGISFBPQOLTM-UHFFFAOYSA-N 0.000 description 1
JEWHCPOELGJVCB-UHFFFAOYSA-N aluminum;calcium;oxido-[oxido(oxo)silyl]oxy-oxosilane;potassium;sodium;tridecahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.O.O.O.[Na].[Al].[K].[Ca].[O-][Si](=O)O[Si]([O-])=O JEWHCPOELGJVCB-UHFFFAOYSA-N 0.000 description 1
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 1
238000004458 analytical method Methods 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
229910001417 caesium ion Inorganic materials 0.000 description 1
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
239000000292 calcium oxide Substances 0.000 description 1
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
QRTXZGIQTYDABO-UHFFFAOYSA-N carbanolate Chemical compound CNC(=O)OC1=CC(C)=C(C)C=C1Cl QRTXZGIQTYDABO-UHFFFAOYSA-N 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000004927 clay Substances 0.000 description 1
229910001603 clinoptilolite Inorganic materials 0.000 description 1
229910001429 cobalt ion Inorganic materials 0.000 description 1
XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 1
229910052681 coesite Inorganic materials 0.000 description 1
229910052906 cristobalite Inorganic materials 0.000 description 1
230000009849 deactivation Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
BCAARMUWIRURQS-UHFFFAOYSA-N dicalcium;oxocalcium;silicate Chemical compound [Ca+2].[Ca+2].[Ca]=O.[O-][Si]([O-])([O-])[O-] BCAARMUWIRURQS-UHFFFAOYSA-N 0.000 description 1
JXSJBGJIGXNWCI-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 description 1
MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
BAQKJENAVQLANS-UHFFFAOYSA-N fenbutrazate Chemical compound C=1C=CC=CC=1C(CC)C(=O)OCCN(C1C)CCOC1C1=CC=CC=C1 BAQKJENAVQLANS-UHFFFAOYSA-N 0.000 description 1
229960002533 fenbutrazate Drugs 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
230000036571 hydration Effects 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
235000015250 liver sausages Nutrition 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
150000003956 methylamines Chemical class 0.000 description 1
239000011707 mineral Substances 0.000 description 1
KRTSDMXIXPKRQR-AATRIKPKSA-N monocrotophos Chemical compound CNC(=O)\C=C(/C)OP(=O)(OC)OC KRTSDMXIXPKRQR-AATRIKPKSA-N 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229940061319 ovide Drugs 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
229910001743 phillipsite Inorganic materials 0.000 description 1
-1 polypropylene Polymers 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
BALXUFOVQVENIU-KXNXZCPBSA-N pseudoephedrine hydrochloride Chemical compound [H+].[Cl-].CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 BALXUFOVQVENIU-KXNXZCPBSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000004064 recycling Methods 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
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229940075554 sorbate Drugs 0.000 description 1
239000010959 steel Substances 0.000 description 1
229910052682 stishovite Inorganic materials 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229910052905 tridymite Inorganic materials 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
229910052725 zinc 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B61/00—Other general methods
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
- C07C209/16—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C211/03—Monoamines
- C07C211/04—Mono-, di- or tri-methylamine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA000495367A 1984-11-16 1985-11-14 Zeolite h-zk-5 as catalyst for conversion of methanol and ammonia to dimethylamine Expired CA1246613A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US672,488		1984-11-16
US06/672,488 US4602112A (en)	1984-11-16	1984-11-16	Zeolite H-ZK-5 as catalyst for conversion of methanol and ammonia to dimethylamine

Publications (1)

Publication Number	Publication Date
CA1246613A true CA1246613A (en)	1988-12-13

Family

ID=24698764

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000495367A Expired CA1246613A (en)	1984-11-16	1985-11-14	Zeolite h-zk-5 as catalyst for conversion of methanol and ammonia to dimethylamine

Country Status (4)

Country	Link
US (1)	US4602112A (2)
JP (1)	JPS61178951A (2)
CA (1)	CA1246613A (2)
ZA (1)	ZA858739B (2)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4737592A (en) *	1984-11-16	1988-04-12	E. I. Du Pont De Nemours And Company	Selected chabazite zeolites as catalysts for conversion of methanol and ammonia to diemethylamine
US4814503A (en) *	1986-06-27	1989-03-21	E. I. Du Pont De Nemours And Company	Zeolite rho and ZK-5 catalysts for conversion of methanol and ammonia to dimethylamine
US5030759A (en) *	1989-04-27	1991-07-09	First Chemical Corporation	Selective N-alkylation of aniline in the presence of zeolite catalysts
US5344989A (en) *	1993-06-15	1994-09-06	E. I. Du Pont De Nemours And Company	Zeolite ZK-5 catalyst for conversion of methanol and ammonia to monomethylamine and dimethylamine
US5399769A (en) *	1993-07-01	1995-03-21	Air Products And Chemicals, Inc.	Preparation of methylamines using shape selective chabazites

Family Cites Families (24)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US19632A (en) *		1858-03-16		hamilton
USRE19632E (en)		1935-07-09		Process fob the catalytic synthesis
US1992935A (en) *	1930-08-27	1935-03-05	Du Pont	Process of producing amines
US1926691A (en) *	1931-12-24	1933-09-12	Commercial Solvents Corp	Process for the production of dimethyl amine
GB422563A (en) *	1933-07-10	1935-01-10	Ig Farbenindustrie Ag	Improvements in the manufacture and production of aliphatic amines
US2349222A (en) *	1940-09-26	1944-05-16	Sharples Chemicals Inc	Manufacture of amines
US2394515A (en) *	1942-04-02	1946-02-05	Sharples Chemicals Inc	Manufacture of amines
US2394516A (en) *	1943-11-24	1946-02-05	Sharples Chemicals Inc	Manufacture of amines
US2456599A (en) *	1945-07-05	1948-12-14	Commercial Solvents Corp	Process for preparing methylamines
US3278598A (en) *	1963-07-18	1966-10-11	Atlas Chem Ind	Ammonolysis process
US3384667A (en) *	1964-04-28	1968-05-21	Mobil Oil Corp	Production of primary and secondary amines
US3387032A (en) *	1965-06-08	1968-06-04	Jackson D. Leonard	Process for the manufacture of methylamines
US3720753A (en) *	1971-02-22	1973-03-13	Exxon Research Engineering Co	Method for preparing a small pore synthetic zeolite
JPS56470B2 (2) *	1972-04-17	1981-01-08
US4082805A (en) *	1974-11-01	1978-04-04	Mobil Oil Corporation	Production of aliphatic amines utilizing a crystalline aluminosilicate catalyst of zsm-5, zsm-11 or zsm-21
US4191709A (en) *	1978-02-06	1980-03-04	Imperial Chemical Industries Limited	Manufacture of amines from alcohols with zeolite FU-1 catalysts
US4254061A (en) *	1979-09-11	1981-03-03	E. I. Du Pont De Nemours And Company	Preparation of monomethylamine
US4313003A (en) *	1979-09-11	1982-01-26	E. I. Du Pont De Nemours And Company	Preparation of dimethylamine
JPS5653887A (en) *	1979-10-09	1981-05-13	Kubota Ltd	Metal solid phase joining method
JPS57169445A (en) *	1981-04-10	1982-10-19	Nitto Chem Ind Co Ltd	Preparation of methylamine
EP0076034B1 (en) *	1981-09-18	1985-05-15	Imperial Chemical Industries Plc	Manufacture of methylamines
US4398041A (en) *	1982-01-29	1983-08-09	Air Products And Chemicals, Inc.	Process for manufacturing alkylamines
US4458092A (en) *	1982-01-29	1984-07-03	Air Products And Chemicals, Inc.	Highly active catalysts for methanol amination
US4434300A (en) *	1982-09-13	1984-02-28	Air Products And Chemicals, Inc.	Methanol amination

1984
- 1984-11-16 US US06/672,488 patent/US4602112A/en not_active Expired - Lifetime
1985
- 1985-11-14 ZA ZA858739A patent/ZA858739B/xx unknown
- 1985-11-14 CA CA000495367A patent/CA1246613A/en not_active Expired
- 1985-11-15 JP JP60256461A patent/JPS61178951A/ja active Granted

Also Published As

Publication number	Publication date
JPS61178951A (ja)	1986-08-11
ZA858739B (en)	1987-07-29
US4602112A (en)	1986-07-22
JPH0310613B2 (2)	1991-02-14

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2005-12-13	MKEX	Expiry

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