JP2002284784A5 - - Google Patents
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- JP2002284784A5 JP2002284784A5 JP2001378736A JP2001378736A JP2002284784A5 JP 2002284784 A5 JP2002284784 A5 JP 2002284784A5 JP 2001378736 A JP2001378736 A JP 2001378736A JP 2001378736 A JP2001378736 A JP 2001378736A JP 2002284784 A5 JP2002284784 A5 JP 2002284784A5
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- Prior art date
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- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 197
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 129
- 238000000034 method Methods 0.000 description 99
- 239000010457 zeolite Substances 0.000 description 90
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 77
- 239000003054 catalyst Substances 0.000 description 76
- 238000006243 chemical reaction Methods 0.000 description 67
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 66
- 229910021536 Zeolite Inorganic materials 0.000 description 61
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 56
- 230000008569 process Effects 0.000 description 52
- 229910052751 metal Inorganic materials 0.000 description 44
- 239000002184 metal Substances 0.000 description 44
- 239000000203 mixture Substances 0.000 description 35
- 239000000377 silicon dioxide Substances 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- 239000002904 solvent Substances 0.000 description 30
- 238000004519 manufacturing process Methods 0.000 description 28
- -1 amine compounds Chemical class 0.000 description 27
- 230000003647 oxidation Effects 0.000 description 25
- 238000007254 oxidation reaction Methods 0.000 description 25
- 229910052681 coesite Inorganic materials 0.000 description 24
- 229910052906 cristobalite Inorganic materials 0.000 description 24
- 229910052682 stishovite Inorganic materials 0.000 description 24
- 229910052905 tridymite Inorganic materials 0.000 description 24
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 20
- 239000007858 starting material Substances 0.000 description 18
- 239000000243 solution Substances 0.000 description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 15
- 238000001354 calcination Methods 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 13
- 239000003085 diluting agent Substances 0.000 description 13
- 239000007789 gas Substances 0.000 description 13
- 150000002739 metals Chemical class 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 12
- 239000007795 chemical reaction product Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 229910052782 aluminium Inorganic materials 0.000 description 11
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 229910052760 oxygen Inorganic materials 0.000 description 11
- 239000001301 oxygen Substances 0.000 description 11
- 238000010791 quenching Methods 0.000 description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
- 238000004821 distillation Methods 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 238000010924 continuous production Methods 0.000 description 9
- 229910052593 corundum Inorganic materials 0.000 description 9
- 229910052742 iron Inorganic materials 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 229910001845 yogo sapphire Inorganic materials 0.000 description 9
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 8
- 239000011230 binding agent Substances 0.000 description 8
- 229910052796 boron Inorganic materials 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 238000000465 moulding Methods 0.000 description 8
- 238000011069 regeneration method Methods 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 230000008929 regeneration Effects 0.000 description 7
- 235000012239 silicon dioxide Nutrition 0.000 description 7
- 229910052719 titanium Inorganic materials 0.000 description 7
- 239000010936 titanium Substances 0.000 description 7
- 229910052723 transition metal Inorganic materials 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- 229910052726 zirconium Inorganic materials 0.000 description 7
- 241001550224 Apha Species 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 6
- 238000001125 extrusion Methods 0.000 description 6
- 229910052733 gallium Inorganic materials 0.000 description 6
- 239000012266 salt solution Substances 0.000 description 6
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 6
- 150000003624 transition metals Chemical class 0.000 description 6
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 5
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 229910052759 nickel Inorganic materials 0.000 description 5
- 230000000171 quenching effect Effects 0.000 description 5
- 229910052720 vanadium Inorganic materials 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 229910052787 antimony Inorganic materials 0.000 description 4
- 229910052785 arsenic Inorganic materials 0.000 description 4
- 229910052790 beryllium Inorganic materials 0.000 description 4
- 229910052797 bismuth Inorganic materials 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 229910052804 chromium Inorganic materials 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 229910052738 indium Inorganic materials 0.000 description 4
- 238000005342 ion exchange Methods 0.000 description 4
- 229910052746 lanthanum Inorganic materials 0.000 description 4
- 229910044991 metal oxide Inorganic materials 0.000 description 4
- 150000004706 metal oxides Chemical class 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 4
- 229910052706 scandium Inorganic materials 0.000 description 4
- 229910052727 yttrium Inorganic materials 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 3
- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- 150000001340 alkali metals Chemical group 0.000 description 3
- 229910000323 aluminium silicate Inorganic materials 0.000 description 3
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 229910052748 manganese Inorganic materials 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 229910052750 molybdenum Inorganic materials 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 150000004885 piperazines Chemical class 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 3
- 229910052718 tin Inorganic materials 0.000 description 3
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- WGCYRFWNGRMRJA-UHFFFAOYSA-N 1-ethylpiperazine Chemical compound CCN1CCNCC1 WGCYRFWNGRMRJA-UHFFFAOYSA-N 0.000 description 2
- WXHLLJAMBQLULT-UHFFFAOYSA-N 2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl]amino]-n-(2-methyl-6-sulfanylphenyl)-1,3-thiazole-5-carboxamide;hydrate Chemical compound O.C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(S1)=NC=C1C(=O)NC1=C(C)C=CC=C1S WXHLLJAMBQLULT-UHFFFAOYSA-N 0.000 description 2
- HXMVNCMPQGPRLN-UHFFFAOYSA-N 2-hydroxyputrescine Chemical compound NCCC(O)CN HXMVNCMPQGPRLN-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical group [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical group [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000002738 chelating agent Substances 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 239000008139 complexing agent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000009849 deactivation Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000011552 falling film Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 229910052732 germanium Inorganic materials 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 229910052914 metal silicate Inorganic materials 0.000 description 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
- PNPIRSNMYIHTPS-UHFFFAOYSA-N nitroso nitrate Chemical class [O-][N+](=O)ON=O PNPIRSNMYIHTPS-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000002161 passivation Methods 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 239000002344 surface layer Substances 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 239000002912 waste gas Substances 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- QVCUKHQDEZNNOC-UHFFFAOYSA-N 1,2-diazabicyclo[2.2.2]octane Chemical compound C1CC2CCN1NC2 QVCUKHQDEZNNOC-UHFFFAOYSA-N 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-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
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- 241001440820 Zethes Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 125000005595 acetylacetonate group Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 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
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 239000011324 bead Substances 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
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 125000001309 chloro group Chemical class Cl* 0.000 description 1
- 239000011362 coarse particle Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 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 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 229910001649 dickite Inorganic materials 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000010981 drying operation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
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- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
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- 229960002195 perazine Drugs 0.000 description 1
- 239000003348 petrochemical agent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10061863.4 | 2000-12-12 | ||
| DE10061863A DE10061863A1 (de) | 2000-12-12 | 2000-12-12 | Verfahren zur Herstellung von Triethylendiamin (TEDA) |
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| DE (3) | DE10061863A1 (enExample) |
| ES (3) | ES2544744T3 (enExample) |
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| US6660731B2 (en) * | 2000-09-15 | 2003-12-09 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| CA2422367C (en) | 2000-09-15 | 2010-05-18 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| US7473691B2 (en) * | 2000-09-15 | 2009-01-06 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| EP1345926B1 (en) * | 2000-12-21 | 2006-05-17 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| MXPA04007697A (es) * | 2002-02-06 | 2004-11-10 | Vertex Pharma | Compuestos de heteroarilo utiles como inhibidores de gsk-3. |
| ATE468336T1 (de) * | 2002-03-15 | 2010-06-15 | Vertex Pharma | Azolylaminoazine als proteinkinasehemmer |
| MY141867A (en) * | 2002-06-20 | 2010-07-16 | Vertex Pharma | Substituted pyrimidines useful as protein kinase inhibitors |
| CN1319968C (zh) | 2002-08-02 | 2007-06-06 | 沃泰克斯药物股份有限公司 | 用作gsk－3的抑制剂的吡唑组合物 |
| WO2004072029A2 (en) * | 2003-02-06 | 2004-08-26 | Vertex Pharmaceuticals Incorporated | Pyrazolopyridazines useful as inhibitors of protein kinases |
| DE10326137A1 (de) * | 2003-06-06 | 2004-12-23 | Basf Ag | Verfahren zur Erhöhung der Schneidhärte eines Formkörpers enthaltend ein kristallines Alumosilikat und Verwendung dieser Formkörper mit erhöhter Schneidhärte in chemischen Syntheseverfahren, insbesondere in einem Verfahren zur Herstellung von Triethylendiamin (TEDA) durch Umsetzung von Ethylendiamin (EDA) und/oder Piperazin (PIP) |
| DE10356184A1 (de) * | 2003-12-02 | 2005-07-07 | Basf Ag | Zeolithisches Material vom Pentasil-Strukturtyp, seine Herstellung und seine Verwendung |
| WO2005056547A2 (en) * | 2003-12-04 | 2005-06-23 | Vertex Pharmaceuticals Incorporated | Quinoxalines useful as inhibitors of protein kinases |
| DE102004024274A1 (de) * | 2004-05-15 | 2005-12-01 | Basf Ag | Verfahren zur Herstellung einer Lösung von reinem Triethylendiamin (TEDA) |
| DE102004029544A1 (de) * | 2004-06-18 | 2006-01-05 | Basf Ag | Formkörper enthaltend ein mikroporöses Material und mindestens ein siliciumhaltiges Bindemittel, Verfahren zu seiner Herstellung und seine Verwendung als Katalysator, insbesondere in einem Verfahren zur Herstellung von Triethylendiamin (TEDA) |
| JP2009504771A (ja) * | 2005-08-18 | 2009-02-05 | バーテックス ファーマシューティカルズ インコーポレイテッド | ピラジンキナーゼ阻害剤 |
| SG166827A1 (en) * | 2005-11-03 | 2010-12-29 | Vertex Pharma | Aminopyrimidines useful as kinase inhibitors |
| CA2668429A1 (en) * | 2006-11-02 | 2008-05-15 | Vertex Pharmaceuticals Incorporated | Aminopyridines and aminopyrimidines useful as inhibitors of protein kinases |
| ES2347721T3 (es) * | 2006-12-19 | 2010-11-03 | Vertex Pharmaceuticals, Inc. | Aminopirimidinas utiles como inhibidores de proteina quinasas. |
| ES2374335T3 (es) * | 2007-03-09 | 2012-02-15 | Vertex Pharmaceuticals Incorporated | Aminopirimidinas útiles como inhibidores de proteína quinasas. |
| WO2008112642A1 (en) * | 2007-03-09 | 2008-09-18 | Vertex Pharmaceuticals Incorporated | Aminopyrimidines useful as inhibitors of protein kinases |
| MX2009009592A (es) * | 2007-03-09 | 2009-11-10 | Vertex Pharma | Aminopiridinas utiles como inhibidores de proteinas cinasas. |
| NZ580343A (en) | 2007-04-13 | 2012-03-30 | Vertex Pharma | Aminopyrimidines useful as kinase inhibitors |
| JP5572087B2 (ja) * | 2007-05-02 | 2014-08-13 | バーテックス ファーマシューティカルズ インコーポレイテッド | キナーゼ阻害として有用なアミノピリミジン |
| WO2008137619A2 (en) * | 2007-05-02 | 2008-11-13 | Vertex Pharmaceuticals Incorporated | Thiazoles and pyrazoles useful as kinase inhibitors |
| EP2152696B1 (en) * | 2007-05-02 | 2014-09-24 | Vertex Pharmaceuticals Incorporated | Aminopyrimidines useful as kinase inhibitors |
| JP2010528021A (ja) * | 2007-05-24 | 2010-08-19 | バーテックス ファーマシューティカルズ インコーポレイテッド | キナーゼのインヒビターとして有用なチアゾールおよびピラゾール |
| WO2009018415A1 (en) * | 2007-07-31 | 2009-02-05 | Vertex Pharmaceuticals Incorporated | Process for preparing 5-fluoro-1h-pyrazolo [3, 4-b] pyridin-3-amine and derivatives thereof |
| KR20110050549A (ko) * | 2008-09-03 | 2011-05-13 | 버텍스 파마슈티칼스 인코포레이티드 | 공-결정 및 이를 포함하는 제약 제제 |
| CN102171178B (zh) | 2008-10-06 | 2015-07-29 | 联合碳化化学品及塑料技术公司 | 乙二胺和其它乙撑胺的连续氨基转移 |
| DE102009027791B4 (de) | 2009-07-17 | 2013-02-21 | Basf Se | Zusammensetzung enthaltend Triethylendiamin, Monethylenglykol und Borhydrid |
| WO2013176803A1 (en) * | 2012-05-24 | 2013-11-28 | Archer Daniels Midland Company | Regeneration of catalyst for hydrogenation of sugars |
| WO2015150489A1 (de) * | 2014-04-03 | 2015-10-08 | Basf Se | Herstellung von teda durch umsetzung von einem amingemisch an einem zeolithkatalysator |
| CN104628675B (zh) * | 2015-02-03 | 2016-09-14 | 西安近代化学研究所 | 一种合成哌嗪和三乙烯二胺的方法 |
| CN104841479B (zh) * | 2015-04-15 | 2017-09-08 | 西安近代化学研究所 | 一种复合固体酸胺化催化剂及其制备方法 |
| CN106831794B (zh) * | 2017-01-20 | 2019-03-05 | 万华化学集团股份有限公司 | 一种制备哌嗪和三乙烯二胺的方法 |
| CN110639605B (zh) * | 2018-06-27 | 2021-10-01 | 中国石油化工股份有限公司 | 用于增产一乙醇胺和二乙醇胺的催化剂 |
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-
2000
- 2000-12-12 DE DE10061863A patent/DE10061863A1/de not_active Withdrawn
-
2001
- 2001-06-26 US US09/765,625 patent/US6562971B2/en not_active Expired - Lifetime
- 2001-11-30 DE DE50107448T patent/DE50107448D1/de not_active Expired - Lifetime
- 2001-11-30 EP EP01128600A patent/EP1215211B1/de not_active Expired - Lifetime
- 2001-11-30 AT AT03009383T patent/ATE304544T1/de not_active IP Right Cessation
- 2001-11-30 EP EP03009385.0A patent/EP1359151B1/de not_active Expired - Lifetime
- 2001-11-30 AT AT01128600T patent/ATE297930T1/de not_active IP Right Cessation
- 2001-11-30 EP EP03009383A patent/EP1338598B1/de not_active Expired - Lifetime
- 2001-11-30 DE DE50106512T patent/DE50106512D1/de not_active Expired - Lifetime
- 2001-11-30 ES ES03009385.0T patent/ES2544744T3/es not_active Expired - Lifetime
- 2001-11-30 ES ES01128600T patent/ES2243380T3/es not_active Expired - Lifetime
- 2001-11-30 ES ES03009383T patent/ES2249652T3/es not_active Expired - Lifetime
- 2001-12-12 CN CNB011456795A patent/CN1181074C/zh not_active Expired - Fee Related
- 2001-12-12 KR KR1020010078510A patent/KR20020046226A/ko not_active Withdrawn
- 2001-12-12 JP JP2001378736A patent/JP4319798B2/ja not_active Expired - Fee Related
-
2003
- 2003-02-06 US US10/359,244 patent/US7115742B2/en not_active Expired - Lifetime
-
2008
- 2008-12-10 JP JP2008314160A patent/JP5086230B2/ja not_active Expired - Fee Related
- 2008-12-10 JP JP2008314159A patent/JP2009102347A/ja active Pending
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