CA2092964A1 - Synthese de 2-methylpropan-2-amine - Google Patents

Synthese de 2-methylpropan-2-amine

Info

Publication number: CA2092964A1
Authority: CA; Canada
Prior art keywords: zeolite beta; zeolite; beta; ammonia; modified
Prior art date: 1992-12-03
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.): Abandoned

Application number

CA 2092964

Other languages

English (en)

Inventor

John Frederick Knifton

Pei-Shing Eugene Dai

Brian Lawrence Benac

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.)

Huntsman Corp

Original Assignee

Texaco Chemical 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.)

1992-12-03

Filing date

1993-03-30

Publication date

1994-06-04

1993-03-30 Application filed by Texaco Chemical Co filed Critical Texaco Chemical Co

1994-06-04 Publication of CA2092964A1 publication Critical patent/CA2092964A1/fr

Status Abandoned legal-status Critical Current

Links

239000010457 zeolite Substances 0.000 title claims abstract description 116
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 title claims abstract description 95
229910021536 Zeolite Inorganic materials 0.000 title claims abstract description 87
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 title claims abstract description 34
230000015572 biosynthetic process Effects 0.000 title abstract description 16
238000003786 synthesis reaction Methods 0.000 title abstract description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 104
229910021529 ammonia Inorganic materials 0.000 claims abstract description 49
238000000034 method Methods 0.000 claims abstract description 44
239000003054 catalyst Substances 0.000 claims abstract description 42
150000001336 alkenes Chemical class 0.000 claims abstract description 39
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims abstract description 34
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 28
238000002360 preparation method Methods 0.000 claims abstract description 11
150000003973 alkyl amines Chemical class 0.000 claims abstract description 10
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 38
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 28
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 21
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 17
150000001412 amines Chemical class 0.000 claims description 16
229910052763 palladium Inorganic materials 0.000 claims description 16
229910052751 metal Inorganic materials 0.000 claims description 15
239000002184 metal Substances 0.000 claims description 15
229910052742 iron Inorganic materials 0.000 claims description 12
229910052804 chromium Inorganic materials 0.000 claims description 11
239000011651 chromium Substances 0.000 claims description 11
150000002739 metals Chemical class 0.000 claims description 10
229910052697 platinum Inorganic materials 0.000 claims description 9
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 8
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 8
229910052802 copper Inorganic materials 0.000 claims description 8
239000010949 copper Substances 0.000 claims description 8
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 7
239000007788 liquid Substances 0.000 claims description 7
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
239000011230 binding agent Substances 0.000 claims description 5
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 5
238000001354 calcination Methods 0.000 claims description 4
229910052748 manganese Inorganic materials 0.000 claims description 4
239000011572 manganese Substances 0.000 claims description 4
229910052759 nickel Inorganic materials 0.000 claims description 4
239000013078 crystal Substances 0.000 claims description 3
150000002366 halogen compounds Chemical class 0.000 claims 2
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims 1
-1 t-butylamine Chemical class 0.000 abstract description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 39
238000006243 chemical reaction Methods 0.000 description 30
238000005576 amination reaction Methods 0.000 description 23
239000000377 silicon dioxide Substances 0.000 description 18
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 14
239000011148 porous material Substances 0.000 description 14
239000005977 Ethylene Substances 0.000 description 13
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 12
230000002378 acidificating effect Effects 0.000 description 11
239000000203 mixture Substances 0.000 description 9
230000008569 process Effects 0.000 description 9
239000000047 product Substances 0.000 description 9
239000002253 acid Substances 0.000 description 8
230000000694 effects Effects 0.000 description 8
INJRKJPEYSAMPD-UHFFFAOYSA-N aluminum;silicic acid;hydrate Chemical compound O.[Al].[Al].O[Si](O)(O)O INJRKJPEYSAMPD-UHFFFAOYSA-N 0.000 description 7
230000008021 deposition Effects 0.000 description 7
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
150000001768 cations Chemical class 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 6
230000003197 catalytic effect Effects 0.000 description 5
229910052681 coesite Inorganic materials 0.000 description 5
229910052906 cristobalite Inorganic materials 0.000 description 5
239000000843 powder Substances 0.000 description 5
150000003141 primary amines Chemical class 0.000 description 5
235000012239 silicon dioxide Nutrition 0.000 description 5
229910052682 stishovite Inorganic materials 0.000 description 5
229910052905 tridymite Inorganic materials 0.000 description 5
230000004913 activation Effects 0.000 description 4
229910052782 aluminium Inorganic materials 0.000 description 4
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
238000006555 catalytic reaction Methods 0.000 description 4
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
150000005673 monoalkenes Chemical class 0.000 description 4
229910052680 mordenite Inorganic materials 0.000 description 4
239000007787 solid Substances 0.000 description 4
229910052723 transition metal Inorganic materials 0.000 description 4
150000003624 transition metals Chemical class 0.000 description 4
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
125000002947 alkylene group Chemical group 0.000 description 3
238000007323 disproportionation reaction Methods 0.000 description 3
229910052675 erionite Inorganic materials 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
239000000523 sample Substances 0.000 description 3
150000003335 secondary amines Chemical class 0.000 description 3
239000011734 sodium Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
238000011282 treatment Methods 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
229910000323 aluminium silicate Inorganic materials 0.000 description 2
125000002091 cationic group Chemical group 0.000 description 2
PHFQLYPOURZARY-UHFFFAOYSA-N chromium trinitrate Chemical compound [Cr+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PHFQLYPOURZARY-UHFFFAOYSA-N 0.000 description 2
229910001603 clinoptilolite Inorganic materials 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
230000001276 controlling effect Effects 0.000 description 2
230000000875 corresponding effect Effects 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
230000007423 decrease Effects 0.000 description 2
238000009826 distribution Methods 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
230000036571 hydration Effects 0.000 description 2
238000006703 hydration reaction Methods 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
230000007246 mechanism Effects 0.000 description 2
239000002609 medium Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
229910000069 nitrogen hydride Inorganic materials 0.000 description 2
230000000269 nucleophilic effect Effects 0.000 description 2
230000000737 periodic effect Effects 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
239000002243 precursor Substances 0.000 description 2
239000000376 reactant Substances 0.000 description 2
239000005060 rubber Substances 0.000 description 2
229910052707 ruthenium Inorganic materials 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
238000001179 sorption measurement Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 2
238000002411 thermogravimetry Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
229910052727 yttrium Inorganic materials 0.000 description 2
OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 description 1
FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 1
BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
101100037762 Caenorhabditis elegans rnh-2 gene Proteins 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
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 1
229910021055 KNH2 Inorganic materials 0.000 description 1
QQGNLKJAIVSNCO-UHFFFAOYSA-N N-butylformamide Chemical compound CCCCNC=O QQGNLKJAIVSNCO-UHFFFAOYSA-N 0.000 description 1
229910018954 NaNH2 Inorganic materials 0.000 description 1
BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
238000002441 X-ray diffraction Methods 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
UKFWSNCTAHXBQN-UHFFFAOYSA-N ammonium iodide Chemical compound [NH4+].[I-] UKFWSNCTAHXBQN-UHFFFAOYSA-N 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
238000013459 approach Methods 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000003899 bactericide agent Substances 0.000 description 1
150000003841 chloride salts Chemical class 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
150000004696 coordination complex Chemical class 0.000 description 1
239000013256 coordination polymer Substances 0.000 description 1
230000002596 correlated effect Effects 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
238000005336 cracking Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000001739 density measurement Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012013 faujasite Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
231100001261 hazardous Toxicity 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
230000006872 improvement Effects 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910052909 inorganic silicate Inorganic materials 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
229910052741 iridium Inorganic materials 0.000 description 1
238000011031 large-scale manufacturing process Methods 0.000 description 1
239000012263 liquid product Substances 0.000 description 1
NFYRMCRBECEAML-UHFFFAOYSA-N manganese palladium Chemical compound [Mn].[Pd] NFYRMCRBECEAML-UHFFFAOYSA-N 0.000 description 1
HBTFASPVVFSRRI-UHFFFAOYSA-N manganese(2+);dinitrate;hydrate Chemical compound O.[Mn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O HBTFASPVVFSRRI-UHFFFAOYSA-N 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
229910001960 metal nitrate Inorganic materials 0.000 description 1
229910001463 metal phosphate Inorganic materials 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
QHCCDDQKNUYGNC-UHFFFAOYSA-N n-ethylbutan-1-amine Chemical compound CCCCNCC QHCCDDQKNUYGNC-UHFFFAOYSA-N 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012038 nucleophile Substances 0.000 description 1
229910052762 osmium Inorganic materials 0.000 description 1
239000008188 pellet Substances 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
229910052761 rare earth metal Inorganic materials 0.000 description 1
150000002910 rare earth metals Chemical group 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
238000012827 research and development Methods 0.000 description 1
238000012552 review Methods 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
150000005619 secondary aliphatic amines Chemical class 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
238000004088 simulation Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
229910001415 sodium ion Inorganic materials 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000004448 titration Methods 0.000 description 1
229910000314 transition metal oxide Inorganic materials 0.000 description 1
VITRLXDSBBVNCZ-UHFFFAOYSA-K trichloroiron;hydrate Chemical compound O.Cl[Fe](Cl)Cl VITRLXDSBBVNCZ-UHFFFAOYSA-K 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1

Landscapes

Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA 2092964 1992-12-03 1993-03-30 Synthese de 2-methylpropan-2-amine Abandoned CA2092964A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US98505792A	1992-12-03	1992-12-03
US07/985,057		1992-12-03

Publications (1)

Publication Number	Publication Date
CA2092964A1 true CA2092964A1 (fr)	1994-06-04

Family

ID=25531152

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2092964 Abandoned CA2092964A1 (fr)	1992-12-03	1993-03-30	Synthese de 2-methylpropan-2-amine

Country Status (1)

Country	Link
CA (1)	CA2092964A1 (fr)

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0778259A2 (fr)	1995-12-08	1997-06-11	Basf Aktiengesellschaft	Procédé pour la préparation d'amines à partir d'oléfines utilisant des zéolithes du type SSZ-37
EP0754676A3 (fr) *	1995-07-20	1997-06-11	Basf Ag	Procédé pour la préparation d'amines à partir d'oléfines utilisant des zéolithes des types PSH-3, MCM-22, SSZ-25 ou leurs mélanges
WO1997021661A1 (fr) *	1995-12-08	1997-06-19	Basf Aktiengesellschaft	Procede de production d'amines a partir d'olefines sur zeolithes du type ssz-26, ssz-33, cit-1 ou des melanges de ces dernieres
EP0785185A1 (fr)	1996-01-17	1997-07-23	Basf Aktiengesellschaft	Procédé de préparation d'amines à partir d'oléfines avec des oxydes cristallins basés sur des aluminophosphates possédant la structure de la faujasite
EP0786449A1 (fr)	1996-01-26	1997-07-30	Basf Aktiengesellschaft	Procédé de préparation d'amines à partir d'oléfines utilisant des faujasites hexagonals
EP0752409A3 (fr) *	1995-07-04	1998-05-20	Basf Aktiengesellschaft	Procédé de préparation d'amines à partir de mélanges obtenus par clivage de coupes pétrolières à l'aide de zéolithes, d'aluminosilicates, de phosphates obtenus par un procédé hydrothermal, d'oxides à surface spécifique élevée, des argiles
US5780680A (en) *	1996-04-19	1998-07-14	Basf Aktiengesellschaft	Preparation of amines from olefins over mesoporous oxides having a high surface area
US5840988A (en) *	1996-12-03	1998-11-24	Basf Aktiengesellschaft	Preparation of amines from olefins on zeolites of the MCM-49 or MCM-56 type
US5874621A (en) *	1997-02-25	1999-02-23	Basf Aktiengesellschaft	Preparation of amines from olefins over NU-85 zeolites
US5877352A (en) *	1996-12-03	1999-03-02	Basf Aktiengesellschaft	Preparation of amines from olefins on boron-MCM-22 or ERB-1 zeolites
EP0752410A3 (fr) *	1995-07-04	1999-04-21	Basf Aktiengesellschaft	Procédé pour la préparation d'amines à partir d'oléfines à l'aide de bêta zéolithes en aluminium libre d'éléments de transition et obtenues sans traitement halogéné
US6143934A (en) *	1995-08-17	2000-11-07	Basf Aktiengesellschaft	Preparation of amines from olefins over boron beta-zeolites
US6350914B1 (en)	1996-07-30	2002-02-26	Basf Aktiengesellschaft	Preparation of amines from olefins over zeolites having an NES structure
WO2011158258A1 (fr)	2010-06-18	2011-12-22	Council Of Scientific & Industrial Research	Méthode améliorée de conversion d'isobutylène en butylamine tertiaire
US8779205B2 (en)	2008-04-09	2014-07-15	Basf Se	Method for pre-treating hydroamination catalysts
CN115254181A (zh) *	2022-09-28	2022-11-01	淄博鲁华泓锦新材料集团股份有限公司	一种生产叔丁胺的催化剂及其制备方法和应用
CN115770608A (zh) *	2022-11-03	2023-03-10	浙江新和成股份有限公司	一种烯烃合成胺类化合物的胺化催化剂及其制备方法和应用
WO2025124131A1 (fr) *	2023-12-13	2025-06-19	中国石油化工股份有限公司	Procédé de production de diphénylamine
TWI919641B (zh)	2023-12-13	2026-03-21	大陸商中國石油化工科技開發有限公司	生產二苯胺的方法

1993
- 1993-03-30 CA CA 2092964 patent/CA2092964A1/fr not_active Abandoned

Cited By (24)

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EP0752410A3 (fr) *	1995-07-04	1999-04-21	Basf Aktiengesellschaft	Procédé pour la préparation d'amines à partir d'oléfines à l'aide de bêta zéolithes en aluminium libre d'éléments de transition et obtenues sans traitement halogéné
EP0752409A3 (fr) *	1995-07-04	1998-05-20	Basf Aktiengesellschaft	Procédé de préparation d'amines à partir de mélanges obtenus par clivage de coupes pétrolières à l'aide de zéolithes, d'aluminosilicates, de phosphates obtenus par un procédé hydrothermal, d'oxides à surface spécifique élevée, des argiles
US5763668A (en) *	1995-07-04	1998-06-09	Basf Aktiengesellschaft	Process for aminating a mixture obtained in cracking a mineral oil fraction with ammonia or a primary or secondary amine over specific heterogeneous catalysts
EP0754676A3 (fr) *	1995-07-20	1997-06-11	Basf Ag	Procédé pour la préparation d'amines à partir d'oléfines utilisant des zéolithes des types PSH-3, MCM-22, SSZ-25 ou leurs mélanges
US6143934A (en) *	1995-08-17	2000-11-07	Basf Aktiengesellschaft	Preparation of amines from olefins over boron beta-zeolites
WO1997021661A1 (fr) *	1995-12-08	1997-06-19	Basf Aktiengesellschaft	Procede de production d'amines a partir d'olefines sur zeolithes du type ssz-26, ssz-33, cit-1 ou des melanges de ces dernieres
US5886226A (en) *	1995-12-08	1999-03-23	Basf Aktiengesellschaft	Process for producing amines from olefins on zeolites of types SSZ-33, CIT-1 or mixtures thereof
EP0778259A2 (fr)	1995-12-08	1997-06-11	Basf Aktiengesellschaft	Procédé pour la préparation d'amines à partir d'oléfines utilisant des zéolithes du type SSZ-37
EP0785185A1 (fr)	1996-01-17	1997-07-23	Basf Aktiengesellschaft	Procédé de préparation d'amines à partir d'oléfines avec des oxydes cristallins basés sur des aluminophosphates possédant la structure de la faujasite
US5786510A (en) *	1996-01-17	1998-07-28	Basf Aktiengesellschaft	Preparation of amines from olefins over crystalline oxides based on aluminum phosphates and having faujasite structure
US5773660A (en) *	1996-01-26	1998-06-30	Basf Aktiengesellschaft	Preparation of amines from olefins over hexagonal faujasites
EP0786449A1 (fr)	1996-01-26	1997-07-30	Basf Aktiengesellschaft	Procédé de préparation d'amines à partir d'oléfines utilisant des faujasites hexagonals
US5780680A (en) *	1996-04-19	1998-07-14	Basf Aktiengesellschaft	Preparation of amines from olefins over mesoporous oxides having a high surface area
US6350914B1 (en)	1996-07-30	2002-02-26	Basf Aktiengesellschaft	Preparation of amines from olefins over zeolites having an NES structure
US5877352A (en) *	1996-12-03	1999-03-02	Basf Aktiengesellschaft	Preparation of amines from olefins on boron-MCM-22 or ERB-1 zeolites
US5840988A (en) *	1996-12-03	1998-11-24	Basf Aktiengesellschaft	Preparation of amines from olefins on zeolites of the MCM-49 or MCM-56 type
US5874621A (en) *	1997-02-25	1999-02-23	Basf Aktiengesellschaft	Preparation of amines from olefins over NU-85 zeolites
US8779205B2 (en)	2008-04-09	2014-07-15	Basf Se	Method for pre-treating hydroamination catalysts
WO2011158258A1 (fr)	2010-06-18	2011-12-22	Council Of Scientific & Industrial Research	Méthode améliorée de conversion d'isobutylène en butylamine tertiaire
CN115254181A (zh) *	2022-09-28	2022-11-01	淄博鲁华泓锦新材料集团股份有限公司	一种生产叔丁胺的催化剂及其制备方法和应用
CN115254181B (zh) *	2022-09-28	2023-01-06	淄博鲁华泓锦新材料集团股份有限公司	一种生产叔丁胺的方法
CN115770608A (zh) *	2022-11-03	2023-03-10	浙江新和成股份有限公司	一种烯烃合成胺类化合物的胺化催化剂及其制备方法和应用
WO2025124131A1 (fr) *	2023-12-13	2025-06-19	中国石油化工股份有限公司	Procédé de production de diphénylamine
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Legal Events

Date	Code	Title	Description
1995-10-01	FZDE	Dead

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