DD298379A5 - Verfahren zur herstellung eines ethers - Google Patents

Verfahren zur herstellung eines ethers Download PDF

Info

Publication number: DD298379A5
Authority: DD; German Democratic Republic
Prior art keywords: zeolite; catalyst; ether; ray diffraction; sio
Prior art date: 1989-12-26

Application number

DD90341364A

Other languages

German (de)

English (en)

Inventor

David O Marler

Werner O Haag

Weldon K Bell

Original Assignee

��@��@��k��

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.)

1989-12-26

Filing date

1990-06-06

Publication date

1992-02-20

1990-06-06 Application filed by ��@��@��k�� filed Critical ��@��@��k��

1990-06-06 Priority to DD90341364A priority Critical patent/DD298379A5/de

1992-02-20 Publication of DD298379A5 publication Critical patent/DD298379A5/de

Links

238000004519 manufacturing process Methods 0.000 title claims description 3
239000010457 zeolite Substances 0.000 claims abstract description 75
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 72
229910021536 Zeolite Inorganic materials 0.000 claims abstract description 70
239000000203 mixture Substances 0.000 claims abstract description 50
239000003054 catalyst Substances 0.000 claims abstract description 48
150000001336 alkenes Chemical class 0.000 claims abstract description 34
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 32
238000000034 method Methods 0.000 claims abstract description 32
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 29
238000006266 etherification reaction Methods 0.000 claims abstract description 23
238000002441 X-ray diffraction Methods 0.000 claims abstract description 18
230000002378 acidificating effect Effects 0.000 claims abstract description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 21
238000001179 sorption measurement Methods 0.000 claims description 18
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 9
238000002360 preparation method Methods 0.000 abstract description 8
150000001298 alcohols Chemical class 0.000 abstract description 5
150000002170 ethers Chemical class 0.000 abstract description 5
239000007858 starting material Substances 0.000 abstract description 5
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 35
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 29
239000000047 product Substances 0.000 description 29
238000006243 chemical reaction Methods 0.000 description 28
229910004298 SiO 2 Inorganic materials 0.000 description 26
239000000126 substance Substances 0.000 description 20
239000013078 crystal Substances 0.000 description 17
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
239000000377 silicon dioxide Substances 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
229910018072 Al 2 O 3 Inorganic materials 0.000 description 12
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 11
239000000463 material Substances 0.000 description 11
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 10
150000001768 cations Chemical class 0.000 description 10
-1 alkaline earth metal cations Chemical class 0.000 description 9
239000011734 sodium Substances 0.000 description 9
HVZJRWJGKQPSFL-UHFFFAOYSA-N tert-Amyl methyl ether Chemical compound CCC(C)(C)OC HVZJRWJGKQPSFL-UHFFFAOYSA-N 0.000 description 9
229910052782 aluminium Inorganic materials 0.000 description 8
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 7
238000002425 crystallisation Methods 0.000 description 7
239000007787 solid Substances 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
230000003197 catalytic effect Effects 0.000 description 6
239000002178 crystalline material Substances 0.000 description 6
230000008025 crystallization Effects 0.000 description 6
229910052739 hydrogen Inorganic materials 0.000 description 6
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 6
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 6
NUMQCACRALPSHD-UHFFFAOYSA-N tert-butyl ethyl ether Chemical compound CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 description 6
YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 5
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 5
229910052796 boron Inorganic materials 0.000 description 5
239000007788 liquid Substances 0.000 description 5
229910052710 silicon Inorganic materials 0.000 description 5
239000010703 silicon Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
238000012360 testing method Methods 0.000 description 5
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 4
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
239000002156 adsorbate Substances 0.000 description 4
ANBBXQWFNXMHLD-UHFFFAOYSA-N aluminum;sodium;oxygen(2-) Chemical compound [O-2].[O-2].[Na+].[Al+3] ANBBXQWFNXMHLD-UHFFFAOYSA-N 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
239000011230 binding agent Substances 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
230000000694 effects Effects 0.000 description 4
QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 4
239000011148 porous material Substances 0.000 description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
229910001388 sodium aluminate Inorganic materials 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000006555 catalytic reaction Methods 0.000 description 3
239000007789 gas Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
238000005342 ion exchange Methods 0.000 description 3
239000011159 matrix material Substances 0.000 description 3
238000002156 mixing Methods 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical class CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
239000005977 Ethylene Substances 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
239000003463 adsorbent Substances 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
229910000323 aluminium silicate Inorganic materials 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
239000004327 boric acid Substances 0.000 description 2
238000001354 calcination Methods 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000002131 composite material Substances 0.000 description 2
239000000470 constituent Substances 0.000 description 2
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
239000008367 deionised water Substances 0.000 description 2
229910021641 deionized water Inorganic materials 0.000 description 2
230000001066 destructive effect Effects 0.000 description 2
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound 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 description 2
AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
238000001125 extrusion Methods 0.000 description 2
125000004836 hexamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
230000036571 hydration Effects 0.000 description 2
238000006703 hydration reaction Methods 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
239000012535 impurity Substances 0.000 description 2
229910052809 inorganic oxide Inorganic materials 0.000 description 2
150000002500 ions Chemical group 0.000 description 2
NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
239000000395 magnesium oxide Substances 0.000 description 2
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
238000005259 measurement Methods 0.000 description 2
229910044991 metal oxide Inorganic materials 0.000 description 2
150000004706 metal oxides Chemical class 0.000 description 2
229910052901 montmorillonite Inorganic materials 0.000 description 2
125000004430 oxygen atom Chemical group O* 0.000 description 2
239000002245 particle Substances 0.000 description 2
125000004817 pentamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
150000003138 primary alcohols Chemical class 0.000 description 2
239000001294 propane Substances 0.000 description 2
239000000376 reactant Substances 0.000 description 2
150000004760 silicates Chemical class 0.000 description 2
LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 2
238000005211 surface analysis Methods 0.000 description 2
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
239000012808 vapor phase Substances 0.000 description 2
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
SZZHDVWITLBFFG-UHFFFAOYSA-N 3-methylbut-1-ene;2-methylprop-1-ene Chemical compound CC(C)=C.CC(C)C=C SZZHDVWITLBFFG-UHFFFAOYSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
239000004606 Fillers/Extenders Substances 0.000 description 1
GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical class CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
239000004115 Sodium Silicate Substances 0.000 description 1
239000004809 Teflon Substances 0.000 description 1
229920006362 Teflon® Polymers 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000005215 alkyl ethers Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
HPTYUNKZVDYXLP-UHFFFAOYSA-N aluminum;trihydroxy(trihydroxysilyloxy)silane;hydrate Chemical compound O.[Al].[Al].O[Si](O)(O)O[Si](O)(O)O HPTYUNKZVDYXLP-UHFFFAOYSA-N 0.000 description 1
238000003556 assay Methods 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
LTPBRCUWZOMYOC-UHFFFAOYSA-N beryllium oxide Inorganic materials O=[Be] LTPBRCUWZOMYOC-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
YZYDPPZYDIRSJT-UHFFFAOYSA-K boron phosphate Chemical compound [B+3].[O-]P([O-])([O-])=O YZYDPPZYDIRSJT-UHFFFAOYSA-K 0.000 description 1
229910000149 boron phosphate Inorganic materials 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
238000004523 catalytic cracking Methods 0.000 description 1
238000005341 cation exchange Methods 0.000 description 1
239000003729 cation exchange resin Substances 0.000 description 1
239000004927 clay Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
238000005336 cracking Methods 0.000 description 1
230000006378 damage Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000007323 disproportionation reaction Methods 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
229910052733 gallium Inorganic materials 0.000 description 1
239000000499 gel Substances 0.000 description 1
229910052732 germanium Inorganic materials 0.000 description 1
GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910052621 halloysite Inorganic materials 0.000 description 1
JYVHOGDBFNJNMR-UHFFFAOYSA-N hexane;hydrate Chemical compound O.CCCCCC JYVHOGDBFNJNMR-UHFFFAOYSA-N 0.000 description 1
238000010335 hydrothermal treatment Methods 0.000 description 1
230000003993 interaction Effects 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
239000001282 iso-butane Substances 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000011738 major mineral Substances 0.000 description 1
235000011963 major mineral Nutrition 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
230000005855 radiation Effects 0.000 description 1
230000035484 reaction time Effects 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
239000004576 sand Substances 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
229910052911 sodium silicate Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
238000004441 surface measurement Methods 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
229910003438 thallium oxide Inorganic materials 0.000 description 1
GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
229910001930 tungsten oxide Inorganic materials 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
- C07C2/12—Catalytic processes with crystalline alumino-silicates or with catalysts comprising molecular sieves
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
- C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups C07C2529/08 - C07C2529/65

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

DD90341364A 1989-12-26 1990-06-06 Verfahren zur herstellung eines ethers DD298379A5 (de)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
DD90341364A DD298379A5 (de)	1989-12-26	1990-06-06	Verfahren zur herstellung eines ethers

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US07/456,702 US4962239A (en)	1988-10-06	1989-12-26	Process for preparing ethers
DD90341364A DD298379A5 (de)	1989-12-26	1990-06-06	Verfahren zur herstellung eines ethers

Publications (1)

Publication Number	Publication Date
DD298379A5 true DD298379A5 (de)	1992-02-20

Family

ID=23813816

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD90341364A DD298379A5 (de)	1989-12-26	1990-06-06	Verfahren zur herstellung eines ethers

Country Status (13)

Country	Link
US (1)	US4962239A (ja)
EP (1)	EP0507770B1 (ja)
JP (1)	JP2806630B2 (ja)
KR (1)	KR0161298B1 (ja)
AT (1)	ATE126192T1 (ja)
AU (1)	AU632803B2 (ja)
CA (1)	CA2072102A1 (ja)
DD (1)	DD298379A5 (ja)
DE (1)	DE69021588T2 (ja)
DK (1)	DK0507770T3 (ja)
ES (1)	ES2075204T3 (ja)
WO (1)	WO1991009829A1 (ja)
ZA (1)	ZA904078B (ja)

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US5231235A (en) *	1992-06-01	1993-07-27	Mobil Oil Corp.	Process for preparing ethers
US5316753A (en) *	1992-10-09	1994-05-31	Chevron Research And Technology Company	Zeolite SSZ-35
US5414146A (en) *	1993-08-23	1995-05-09	Mobil Oil Corporation	Multizone catalytic process
US5600045A (en) *	1993-12-02	1997-02-04	The Dow Chemical Company	Process for conversion of crude hydrocarbon mixtures
US5470810A (en) *	1994-02-02	1995-11-28	Mobil Oil Corporation	Catalyst and method of manufacture
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US7402187B2 (en) *	2002-10-09	2008-07-22	Chevron U.S.A. Inc.	Recovery of alcohols from Fischer-Tropsch naphtha and distillate fuels containing the same
US6824574B2 (en) *	2002-10-09	2004-11-30	Chevron U.S.A. Inc.	Process for improving production of Fischer-Tropsch distillate fuels
WO2005102975A1 (ja) *	2004-04-23	2005-11-03	Central Glass Company, Limited	フッ素化エーテルの製造方法
US7799316B2 (en) *	2006-02-14	2010-09-21	Exxonmobil Chemical Patents Inc.	Process for manufacturing MCM-22 family molecular sieves
WO2007094938A1 (en) *	2006-02-14	2007-08-23	Exxonmobil Chemical Patents Inc.	An mcm-22 family molecular sieve composition
CN101384365B (zh) *	2006-02-14	2012-02-08	埃克森美孚化学专利公司	制备分子筛组合物的方法
US7959899B2 (en) *	2006-07-28	2011-06-14	Exxonmobil Chemical Patents Inc.	Molecular sieve composition (EMM-10-P), its method of making, and use for hydrocarbon conversions
BRPI0713674A2 (pt)	2006-07-28	2012-10-23	Exxonmobil Chem Patents Inc	formulações farmarcêuticas e composições de um antagonista seletivo cxcr2 ou cxcr1 e métodos para o uso do mesmo visando o tratamento de distúrbios inflamatórios
KR101120880B1 (ko)	2006-07-28	2012-02-27	엑손모빌 케미칼 패턴츠 인코포레이티드	분자체 조성물(ｅｍｍ-10-ｐ), 이의 제조 방법, 및 탄화수소 전환에 있어서의 용도
JP5476379B2 (ja) *	2008-07-28	2014-04-23	エクソンモービル・ケミカル・パテンツ・インク	新規なモレキュラーシーブ組成物ｅｍｍ−１２、その製造方法およびその使用プロセス
RU2509055C2 (ru) *	2008-07-28	2014-03-10	Эксонмобил Кемикэл Пейтентс Инк.	Новая молекулярно-ситовая композиция емм-12, способы ее получения и применения
JP5461553B2 (ja) *	2008-07-28	2014-04-02	エクソンモービル・ケミカル・パテンツ・インク	Ｅｍｍ−１２を用いるアルキル芳香族化合物の製造方法
EP2321222B1 (en)	2008-07-28	2019-01-02	ExxonMobil Chemical Patents Inc.	A novel molecular sieve composition emm-12 and a process of using the same
CN102105397B (zh)	2008-07-28	2014-02-05	埃克森美孚化学专利公司	使用emm-13制备烷基芳族化合物的方法
WO2010014404A1 (en) *	2008-07-28	2010-02-04	Exxonmobil Chemical Patents Inc.	Process of making alkylaromatics using emm-13
EP2322972A1 (fr) *	2009-11-12	2011-05-18	Johnson Controls Technology Company	Dispositif d'affichage, notamment pour véhicule automobile
US9205398B2 (en)	2012-08-21	2015-12-08	Uop Llc	Production of butanediol from a methane conversion process
US9023255B2 (en)	2012-08-21	2015-05-05	Uop Llc	Production of nitrogen compounds from a methane conversion process
US9308513B2 (en)	2012-08-21	2016-04-12	Uop Llc	Production of vinyl chloride from a methane conversion process
US9327265B2 (en)	2012-08-21	2016-05-03	Uop Llc	Production of aromatics from a methane conversion process
US9434663B2 (en)	2012-08-21	2016-09-06	Uop Llc	Glycols removal and methane conversion process using a supersonic flow reactor
US8927769B2 (en)	2012-08-21	2015-01-06	Uop Llc	Production of acrylic acid from a methane conversion process
US9656229B2 (en)	2012-08-21	2017-05-23	Uop Llc	Methane conversion apparatus and process using a supersonic flow reactor
US8937186B2 (en)	2012-08-21	2015-01-20	Uop Llc	Acids removal and methane conversion process using a supersonic flow reactor
US9689615B2 (en)	2012-08-21	2017-06-27	Uop Llc	Steady state high temperature reactor
US9707530B2 (en)	2012-08-21	2017-07-18	Uop Llc	Methane conversion apparatus and process using a supersonic flow reactor
US8933275B2 (en)	2012-08-21	2015-01-13	Uop Llc	Production of oxygenates from a methane conversion process
US9370757B2 (en)	2012-08-21	2016-06-21	Uop Llc	Pyrolytic reactor

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US4605787A (en) *	1984-08-16	1986-08-12	Mobil Oil Corporation	Process for the preparation of alkyl tert-alkyl ethers
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US4826667A (en) *	1986-01-29	1989-05-02	Chevron Research Company	Zeolite SSZ-25
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US4831195A (en) *	1987-04-29	1989-05-16	Mobil Oil Corporation	Production of ethers from methanol
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US4830635A (en) *	1987-12-08	1989-05-16	Mobil Oil Corporation	Production of liquid hydrocarbon and ether mixtures
US4835329A (en) *	1987-12-08	1989-05-30	Mobil Oil Corporation	Process for producing high octane gasoline
US4820877A (en) *	1987-12-28	1989-04-11	Mobil Oil Corporation	Etherification process improvement
US4814519A (en) *	1987-12-30	1989-03-21	Mobil Oil Corporation	Production of ethers from olefins
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1989
- 1989-12-26 US US07/456,702 patent/US4962239A/en not_active Expired - Fee Related
1990
- 1990-04-09 DK DK90906460.2T patent/DK0507770T3/da active
- 1990-04-09 JP JP2506207A patent/JP2806630B2/ja not_active Expired - Lifetime
- 1990-04-09 KR KR1019920701231A patent/KR0161298B1/ko not_active IP Right Cessation
- 1990-04-09 WO PCT/US1990/001922 patent/WO1991009829A1/en active IP Right Grant
- 1990-04-09 ES ES90906460T patent/ES2075204T3/es not_active Expired - Lifetime
- 1990-04-09 AT AT90906460T patent/ATE126192T1/de not_active IP Right Cessation
- 1990-04-09 CA CA002072102A patent/CA2072102A1/en not_active Abandoned
- 1990-04-09 AU AU54287/90A patent/AU632803B2/en not_active Ceased
- 1990-04-09 DE DE69021588T patent/DE69021588T2/de not_active Expired - Fee Related
- 1990-04-09 EP EP90906460A patent/EP0507770B1/en not_active Expired - Lifetime
- 1990-05-28 ZA ZA904078A patent/ZA904078B/xx unknown
- 1990-06-06 DD DD90341364A patent/DD298379A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
JPH05502855A (ja)	1993-05-20
EP0507770A4 (en)	1993-03-31
WO1991009829A1 (en)	1991-07-11
KR0161298B1 (ko)	1999-01-15
ZA904078B (en)	1992-01-29
EP0507770A1 (en)	1992-10-14
AU5428790A (en)	1991-07-24
JP2806630B2 (ja)	1998-09-30
ATE126192T1 (de)	1995-08-15
EP0507770B1 (en)	1995-08-09
DE69021588D1 (de)	1995-09-14
DE69021588T2 (de)	1996-01-18
CA2072102A1 (en)	1991-06-27
US4962239A (en)	1990-10-09
ES2075204T3 (es)	1995-10-01
DK0507770T3 (da)	1995-12-11
KR927003495A (ko)	1992-12-18
AU632803B2 (en)	1993-01-14

Legal Events

Date	Code	Title	Description
1996-11-07	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DD298379A5 (de)	1992-02-20	Verfahren zur herstellung eines ethers
DE2560440C2 (de)	1986-11-13	Verfahren zur Herstellung von Kohlenwasserstoffen
DE68916821T2 (de)	1994-10-27	Katalysatoren und Verfahren zur Oligomerisierung von Olefinen in Gegenwart von Nickel enthaltenden zeolitischen Katalysatoren.
AT401620B (de)	1996-10-25	Synthetisches poröses kristallines material und seine synthese
DE60006964T2 (de)	2004-10-28	Synthetisches poröses kristallines mcm-68, synthese und verwendung desselben
DE60310898T2 (de)	2007-10-11	Chabazit mit hohem gehalt an siliciumdioxid, dessen synthese und verwendung zur umwandlung von sauerstoffverbindungen zu olefinen
DE69421288T2 (de)	2000-02-03	Poröses synthetisches kristallines material mcm-58, dessen synthese und verwendung
DE69819989T3 (de)	2012-10-04	Zusammensetzung, die Molekularsiebe vom Pentasil-Typ enthõlt, sowie ihre Herstellung und Verwendung
DE4310792C2 (de)	1999-03-18	Zeolithisches Material, dessen Verwendung sowie Verfahren zum Herstellen eines solchen zeolithhaltigen Materials
DE69205003T2 (de)	1996-02-22	Synthetischer kristalliner zeolith, seine synthese sowie seine verwendung.
DE69105305T2 (de)	1995-04-06	Katalytische Hydrodealkylierung von aromatischen Verbindungen.
DE69013362T2 (de)	1995-02-16	Zusammenzetzung und verfahren zum katalytischen kracken.
EP0007081A1 (de)	1980-01-23	Verfahren zur Herstellung von stickstoffhaltigen kristallinen Metallsilikaten mit Zeolithstruktur, nach dem Verfahren hergestellte Metallsilikate sowie deren Verwendung als Katalysatoren
EP0353914A2 (en)	1990-02-07	Novel crystalline (metallo) silicates and germanates
DE3119160A1 (de)	1982-03-11	Caesiumhaltiger zeolith und verfahren zu dessen herstellung
DE2826865C2 (ja)	1989-03-09
DE2749024C2 (de)	1987-03-26	Kristalline Aluminosilicat-Zeolithe, Verfahren zu ihrer Herstellung und ihre Verwendung
DE69016673T2 (de)	1995-06-01	Verfahren zur katalytischen disproportionierung von methylnaphthalenen.
DE69805016T2 (de)	2003-02-27	Katalytisches Krackverfahren von Kohlenwasserstoffeinsätzen mit einem Katalysator, der einen IM-5 Zeolit enthäle, der eventuel entaluminiert kann sein
DE69010743T2 (de)	1995-03-16	Silikometallatmolekularsiebe und deren Anwendung als Katalysatoren bei der Oxydierung von Alkanen.
DE69031214T2 (de)	1998-02-26	Verfahren zur katalytischen konversion einer c9+ -aromatischen charge
EP2528684B1 (de)	2018-06-27	Verbesserter katalysator auf zeolithbasis zur herstellung von olefinen und zur oligomerisierung von olefinen
DE2813969A1 (de)	1978-10-12	Verfahren zur herstellung kristalliner zeolithe
DE102012217923A1 (de)	2014-04-03	Herstellung von Katalysatoren auf Basis von Bor-Zeolithen
DE69526069T2 (de)	2002-12-19	Verbesserte mcm-22 katalysatorzusammensetzung