DE10061863A1 - Verfahren zur Herstellung von Triethylendiamin (TEDA) - Google Patents
Verfahren zur Herstellung von Triethylendiamin (TEDA)Info
- Publication number
- DE10061863A1 DE10061863A1 DE10061863A DE10061863A DE10061863A1 DE 10061863 A1 DE10061863 A1 DE 10061863A1 DE 10061863 A DE10061863 A DE 10061863A DE 10061863 A DE10061863 A DE 10061863A DE 10061863 A1 DE10061863 A1 DE 10061863A1
- Authority
- DE
- Germany
- Prior art keywords
- teda
- eda
- oxidation state
- zeolite catalyst
- metal
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 title claims abstract description 190
- 239000010457 zeolite Substances 0.000 title claims abstract description 93
- 239000003054 catalyst Substances 0.000 title claims abstract description 78
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 title claims abstract description 77
- 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 64
- 229910021536 Zeolite Inorganic materials 0.000 title claims abstract description 59
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 239000003814 drug Substances 0.000 title description 2
- 229920000642 polymer Polymers 0.000 title description 2
- 229910052751 metal Inorganic materials 0.000 claims abstract description 60
- 239000002184 metal Substances 0.000 claims abstract description 60
- 230000003647 oxidation Effects 0.000 claims abstract description 44
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 44
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 20
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 12
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 10
- 235000012239 silicon dioxide Nutrition 0.000 claims abstract description 7
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 124
- 238000000034 method Methods 0.000 claims description 103
- 230000008569 process Effects 0.000 claims description 45
- 238000006243 chemical reaction Methods 0.000 claims description 42
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 27
- 239000002904 solvent Substances 0.000 claims description 25
- 150000002739 metals Chemical class 0.000 claims description 24
- -1 amine Compounds Chemical class 0.000 claims description 20
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 18
- 239000007789 gas Substances 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 14
- 239000003085 diluting agent Substances 0.000 claims description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- 229910052742 iron Inorganic materials 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 9
- 229910052796 boron Inorganic materials 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 229910052726 zirconium Inorganic materials 0.000 claims description 8
- 229910052733 gallium Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 229910052719 titanium Inorganic materials 0.000 claims description 7
- 229910052723 transition metal Inorganic materials 0.000 claims description 7
- 150000003624 transition metals Chemical class 0.000 claims description 7
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 239000011230 binding agent Substances 0.000 claims description 6
- 229910052759 nickel Inorganic materials 0.000 claims description 6
- 229910052720 vanadium Inorganic materials 0.000 claims description 6
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 5
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 229910052787 antimony Inorganic materials 0.000 claims description 5
- 229910052785 arsenic Inorganic materials 0.000 claims description 5
- 229910052790 beryllium Inorganic materials 0.000 claims description 5
- 229910052797 bismuth Inorganic materials 0.000 claims description 5
- 229910052738 indium Inorganic materials 0.000 claims description 5
- 229910052746 lanthanum Inorganic materials 0.000 claims description 5
- 229910052718 tin Inorganic materials 0.000 claims description 5
- 229910052727 yttrium Inorganic materials 0.000 claims description 5
- 229910052725 zinc Inorganic materials 0.000 claims description 5
- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 claims description 4
- 229910052804 chromium Inorganic materials 0.000 claims description 4
- 229910052748 manganese Inorganic materials 0.000 claims description 4
- 229910052750 molybdenum Inorganic materials 0.000 claims description 4
- 229910052706 scandium Inorganic materials 0.000 claims description 4
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 3
- 241000158147 Sator Species 0.000 claims description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 3
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 claims description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 3
- 229960001124 trientine Drugs 0.000 claims description 3
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 claims description 3
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract description 8
- 229910052681 coesite Inorganic materials 0.000 abstract 1
- 229910052906 cristobalite Inorganic materials 0.000 abstract 1
- 229910052682 stishovite Inorganic materials 0.000 abstract 1
- 229910052905 tridymite Inorganic materials 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 description 23
- 238000001354 calcination Methods 0.000 description 15
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 11
- 238000010791 quenching Methods 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 238000011069 regeneration method Methods 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 238000001125 extrusion Methods 0.000 description 7
- 230000008929 regeneration Effects 0.000 description 7
- 239000010936 titanium Substances 0.000 description 7
- 241001550224 Apha Species 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 6
- 239000012266 salt solution Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 229910044991 metal oxide Inorganic materials 0.000 description 5
- 150000004706 metal oxides Chemical class 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 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
- 230000008901 benefit Effects 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 238000005342 ion exchange Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 150000004885 piperazines Chemical class 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 150000003839 salts Chemical group 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 238000007493 shaping process Methods 0.000 description 4
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 238000010924 continuous production Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000009849 deactivation Effects 0.000 description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000011552 falling film Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229940066771 systemic antihistamines piperazine derivative Drugs 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
- 229910010413 TiO 2 Inorganic materials 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical group 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical group 0.000 description 2
- 229910000323 aluminium silicate Inorganic materials 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000008139 complexing agent Substances 0.000 description 2
- 150000002169 ethanolamines Chemical class 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000006193 liquid solution Substances 0.000 description 2
- 229910052914 metal silicate Inorganic materials 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000002823 nitrates Chemical class 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
- 239000000843 powder Substances 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 238000002791 soaking Methods 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 2
- 229960004418 trolamine Drugs 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
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- 229910021532 Calcite Inorganic materials 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 241001026509 Kata Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 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
- 241000589614 Pseudomonas stutzeri Species 0.000 description 1
- 229910004283 SiO 4 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
- 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 group 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 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
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 235000012216 bentonite Nutrition 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000013064 chemical raw material Substances 0.000 description 1
- 239000003245 coal Substances 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
- 238000001816 cooling Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 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
- 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
- 230000005611 electricity Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010574 gas phase reaction Methods 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
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052621 halloysite Inorganic materials 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000001027 hydrothermal synthesis Methods 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
- 239000012535 impurity Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 238000002370 liquid polymer infiltration Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000001477 organic nitrogen group Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000003348 petrochemical agent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005496 tempering Methods 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (18)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10061863A DE10061863A1 (de) | 2000-12-12 | 2000-12-12 | Verfahren zur Herstellung von Triethylendiamin (TEDA) |
| US09/765,625 US6562971B2 (en) | 2000-12-12 | 2001-06-26 | Process for the preparation of triethylenediamine (TEDA) |
| DE50107448T DE50107448D1 (de) | 2000-12-12 | 2001-11-30 | Verfahren zur Herstellung von Triethylendiamin (TEDA) |
| EP03009383A EP1338598B1 (de) | 2000-12-12 | 2001-11-30 | Verfahren zur Herstellung von Triethylendiamin (TEDA) |
| DE50106512T DE50106512D1 (de) | 2000-12-12 | 2001-11-30 | Verfahren zur Herstellung von Triethylendiamin (TEDA) |
| ES01128600T ES2243380T3 (es) | 2000-12-12 | 2001-11-30 | Procedimiento para la obtencion de trietilendiamina (teda). |
| EP01128600A EP1215211B1 (de) | 2000-12-12 | 2001-11-30 | Verfahren zur Herstellung von Triethylendiamin (TEDA) |
| AT03009383T ATE304544T1 (de) | 2000-12-12 | 2001-11-30 | Verfahren zur herstellung von triethylendiamin (teda) |
| ES03009385.0T ES2544744T3 (es) | 2000-12-12 | 2001-11-30 | Procedimiento para la preparación de trietilendiamina (TEDA) |
| AT01128600T ATE297930T1 (de) | 2000-12-12 | 2001-11-30 | Verfahren zur herstellung von triethylendiamin (teda) |
| ES03009383T ES2249652T3 (es) | 2000-12-12 | 2001-11-30 | Procedimiento para la obtencion de trimetilendiamina (teda). |
| EP03009385.0A EP1359151B1 (de) | 2000-12-12 | 2001-11-30 | Verfahren zur Herstellung von Triethylendiamin (TEDA) |
| CNB011456795A CN1181074C (zh) | 2000-12-12 | 2001-12-12 | 制备三亚乙基二胺(teda)的方法 |
| JP2001378736A JP4319798B2 (ja) | 2000-12-12 | 2001-12-12 | トリエチレンジアミンの製造方法 |
| KR1020010078510A KR20020046226A (ko) | 2000-12-12 | 2001-12-12 | 트리에틸렌디아민 (ｔｅｄａ)의 제조 방법 |
| US10/359,244 US7115742B2 (en) | 2000-12-12 | 2003-02-06 | Process for the preparation of triethylenediamine (TEDA) from ethylenediamine |
| JP2008314160A JP5086230B2 (ja) | 2000-12-12 | 2008-12-10 | トリエチレンジアミンの製造方法 |
| JP2008314159A JP2009102347A (ja) | 2000-12-12 | 2008-12-10 | トリエチレンジアミンの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10061863A DE10061863A1 (de) | 2000-12-12 | 2000-12-12 | Verfahren zur Herstellung von Triethylendiamin (TEDA) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10061863A1 true DE10061863A1 (de) | 2002-06-13 |
Family
ID=7666827
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10061863A Withdrawn DE10061863A1 (de) | 2000-12-12 | 2000-12-12 | Verfahren zur Herstellung von Triethylendiamin (TEDA) |
| DE50106512T Expired - Lifetime DE50106512D1 (de) | 2000-12-12 | 2001-11-30 | Verfahren zur Herstellung von Triethylendiamin (TEDA) |
| DE50107448T Expired - Lifetime DE50107448D1 (de) | 2000-12-12 | 2001-11-30 | Verfahren zur Herstellung von Triethylendiamin (TEDA) |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE50106512T Expired - Lifetime DE50106512D1 (de) | 2000-12-12 | 2001-11-30 | Verfahren zur Herstellung von Triethylendiamin (TEDA) |
| DE50107448T Expired - Lifetime DE50107448D1 (de) | 2000-12-12 | 2001-11-30 | Verfahren zur Herstellung von Triethylendiamin (TEDA) |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US6562971B2 (https=) |
| EP (3) | EP1359151B1 (https=) |
| JP (3) | JP4319798B2 (https=) |
| KR (1) | KR20020046226A (https=) |
| CN (1) | CN1181074C (https=) |
| AT (2) | ATE304544T1 (https=) |
| DE (3) | DE10061863A1 (https=) |
| ES (3) | ES2249652T3 (https=) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7473691B2 (en) * | 2000-09-15 | 2009-01-06 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| WO2002022605A1 (en) * | 2000-09-15 | 2002-03-21 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| US6660731B2 (en) * | 2000-09-15 | 2003-12-09 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| US6989385B2 (en) * | 2000-12-21 | 2006-01-24 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| WO2003066629A2 (en) * | 2002-02-06 | 2003-08-14 | Vertex Pharmaceuticals Incorporated | Heteroaryl compounds useful as inhibitors of gsk-3 |
| US20040009981A1 (en) * | 2002-03-15 | 2004-01-15 | David Bebbington | Compositions useful as inhibitors of protein kinases |
| 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 |
| US7601718B2 (en) * | 2003-02-06 | 2009-10-13 | Vertex Pharmaceuticals Incorporated | Compositions 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 |
| US7592340B2 (en) * | 2003-12-04 | 2009-09-22 | 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) |
| ATE542814T1 (de) * | 2005-08-18 | 2012-02-15 | Vertex Pharma | Pyrazinkinaseinhibitoren |
| MX2008005814A (es) * | 2005-11-03 | 2008-10-15 | Vertex Pharma | Aminopirimidinas utiles como inhibidores de cinasa. |
| 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. |
| EP2137183B1 (en) * | 2007-03-09 | 2011-09-28 | Vertex Pharmaceuticals Incorporated | Aminopyrimidines useful as inhibitors of protein kinases |
| AU2008226457B2 (en) * | 2007-03-09 | 2014-03-20 | Vertex Pharmaceuticals Incorporated | Aminopyrimidines useful as inhibitors of protein kinases |
| EP2134709A1 (en) | 2007-03-09 | 2009-12-23 | Vertex Pharmaceuticals, Inc. | Aminopyridines useful as inhibitors of protein kinases |
| NZ580343A (en) | 2007-04-13 | 2012-03-30 | Vertex Pharma | Aminopyrimidines useful as kinase inhibitors |
| MX2009011811A (es) * | 2007-05-02 | 2010-01-14 | Vertex Pharma | Aminopirimidinas utiles como inhibidores de cinasa. |
| JP5389785B2 (ja) | 2007-05-02 | 2014-01-15 | 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 | キナーゼ阻害剤として有用なチアゾールおよびピラゾール |
| CA2694381A1 (en) * | 2007-05-02 | 2008-11-13 | Vertex Pharmaceuticals Incorporated | Aminopyrimidines useful as kinase inhibitors |
| EP2164842A2 (en) * | 2007-05-24 | 2010-03-24 | Vertex Pharmaceuticals Incorporated | Thiazoles and pyrazoles useful as kinase inhibitors |
| NZ582879A (en) * | 2007-07-31 | 2012-03-30 | Vertex Pharma | Process for preparing 5-fluoro-1h-pyrazolo [3, 4-b] pyridin-3-amine and derivatives thereof |
| MX2011002312A (es) * | 2008-09-03 | 2011-04-26 | Vertex Pharma | Co-cristales y formulaciones farmaceuticas que comprenden los mismos. |
| US8383860B2 (en) | 2008-10-06 | 2013-02-26 | Union Carbide Chemicals & Plastics Technology Llc | Process to selectively manufacture diethylenetriamine (DETA) or other desirable ethyleneamines via continuous transamination of ethylenediamine (EDA), and other ethyleneamines over a heterogeneous catalyst system |
| DE102009027791B4 (de) | 2009-07-17 | 2013-02-21 | Basf Se | Zusammensetzung enthaltend Triethylendiamin, Monethylenglykol und Borhydrid |
| MY170884A (en) * | 2012-05-24 | 2019-09-11 | Archer Daniels Midland Co | Regeneration of catalyst for hydrogenation of sugars |
| CN106164042A (zh) * | 2014-04-03 | 2016-11-23 | 巴斯夫欧洲公司 | 通过胺混合物在沸石催化剂上反应而制备teda |
| 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 |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE206896C (https=) | ||||
| US2937176A (en) | 1956-12-17 | 1960-05-17 | Houdry Process Corp | Preparation of diazabicyclo-octane |
| US3285920A (en) | 1964-01-16 | 1966-11-15 | Jefferson Chem Co Inc | Combination process for producing piperazine and triethylenediamine |
| US3702886A (en) | 1969-10-10 | 1972-11-14 | Mobil Oil Corp | Crystalline zeolite zsm-5 and method of preparing the same |
| JPS4948609A (https=) * | 1972-09-13 | 1974-05-11 | ||
| JPS5337876B2 (https=) | 1973-07-19 | 1978-10-12 | ||
| DE2846813A1 (de) | 1978-10-27 | 1980-05-08 | Bayer Ag | Verfahren zur herstellung von 1,4-diazabicyclo-(2,2,2)-octan |
| EP0158319A3 (en) | 1984-04-10 | 1988-05-25 | Union Carbide Corporation | Synthesis of 1-azabicyclo(2.2.2) octanes or 1,4-diazabicyclo(2-2.2)octanes |
| WO1987003592A1 (fr) * | 1985-12-05 | 1987-06-18 | Idemitsu Kosan Company Limited | Procede de production de triethylenediamines |
| EP0263463B1 (de) * | 1986-10-08 | 1992-03-25 | BASF Aktiengesellschaft | Verfahren zur Herstellung von 1,4-Diazabicyclo(2,2,2)-octanen |
| US4804758A (en) | 1986-10-08 | 1989-02-14 | Basf Aktiengesellschaft | Preparation of 1,4-diazabicyclo[2.2.2]octanes |
| JPH0633266B2 (ja) | 1986-11-10 | 1994-05-02 | 出光興産株式会社 | トリエチレンジアミン類の製造方法 |
| US5053374A (en) | 1987-05-01 | 1991-10-01 | Mobil Oil Corporation | Method for preparing a zeolite catalyst bound with a refractory oxide of low acidity |
| DE3735214A1 (de) | 1987-10-17 | 1989-04-27 | Huels Chemische Werke Ag | Verfahren zur herstellung von 1,4-diazabicyclo(2.2.2)-octan aus piperazin |
| DE3735212A1 (de) | 1987-10-17 | 1989-04-27 | Huels Chemische Werke Ag | Verfahren zur herstellung von gemischen aus 1,4-diazabicyclo(2.2.2)-octan und piperazin |
| EP0345330A1 (en) | 1987-12-18 | 1989-12-13 | Union Carbide Corporation | Processes for the production of amines |
| DE3823160A1 (de) | 1988-07-08 | 1990-01-11 | Basf Ag | Verfahren zur herstellung von 1,4-diazabicyclo-2,2,2-octanen |
| DE3903622A1 (de) | 1989-02-08 | 1990-08-09 | Basf Ag | Verfahren zur herstellung von 1,4-diazabicyclo-2,2,2-octan |
| DE3934459A1 (de) | 1989-10-14 | 1991-04-18 | Bayer Ag | Verfahren zur herstellung von triethylendiamin und piperazin |
| US5194613A (en) * | 1990-09-20 | 1993-03-16 | Union Carbide Chemicals & Plastics Technology Corporation | Catalytic processes for the preparation of bridged nitrogen-containing compounds |
| US5754741A (en) * | 1992-08-10 | 1998-05-19 | Computer Motion, Inc. | Automated endoscope for optimal positioning |
| RU2071475C1 (ru) | 1993-08-31 | 1997-01-10 | Институт катализа им.Г.К.Борескова СО РАН | Способ получения триэтилендиамина |
| RU2114849C1 (ru) | 1996-04-09 | 1998-07-10 | Конструкторско-технологический институт каталитических и адсорбционных процессов на цеолитах "Цеосит" СО РАН | Способ получения триэтилендиамина |
| US5731449A (en) | 1996-09-23 | 1998-03-24 | Air Products And Chemicals, Inc. | Triethylendiamine synthesis with base-treated zeolites as catalysts |
| US5756741A (en) | 1996-11-15 | 1998-05-26 | Air Products And Chemicals, Inc. | Process for the production of triethylenediamine |
| US5741906A (en) | 1996-11-15 | 1998-04-21 | Air Products And Chemicals, Inc. | Production of triethylenediamine using surface acidity deactivated zeolite catalysts |
| DE19723949A1 (de) * | 1997-06-06 | 1998-12-10 | Basf Ag | Verfahren zur Regenerierung eines Zeolith-Katalysators |
| US6084096A (en) * | 1998-04-09 | 2000-07-04 | Air Products And Chemicals, Inc. | Triethylenediamine and piperazine synthesis using zeolite catalysts modified with a silicon-containing compound |
| US6350874B1 (en) * | 1999-04-01 | 2002-02-26 | Tosoh Corporation | Method for producing triethylenediamines and piperazines |
| DE19930736C2 (de) | 1999-07-05 | 2001-07-05 | Performance Chemicals Handels | Verfahren zur Herstellung von Triethylendiamin unter Einsatz von Ethylendiamin |
-
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 ES ES03009383T patent/ES2249652T3/es not_active Expired - Lifetime
- 2001-11-30 EP EP03009385.0A patent/EP1359151B1/de not_active Expired - Lifetime
- 2001-11-30 DE DE50106512T patent/DE50106512D1/de not_active Expired - Lifetime
- 2001-11-30 AT AT03009383T patent/ATE304544T1/de not_active IP Right Cessation
- 2001-11-30 AT AT01128600T patent/ATE297930T1/de not_active IP Right Cessation
- 2001-11-30 EP EP01128600A patent/EP1215211B1/de not_active Expired - Lifetime
- 2001-11-30 ES ES01128600T patent/ES2243380T3/es not_active Expired - Lifetime
- 2001-11-30 EP EP03009383A patent/EP1338598B1/de not_active Expired - Lifetime
- 2001-11-30 DE DE50107448T patent/DE50107448D1/de not_active Expired - Lifetime
- 2001-11-30 ES ES03009385.0T patent/ES2544744T3/es not_active Expired - Lifetime
- 2001-12-12 JP JP2001378736A patent/JP4319798B2/ja not_active Expired - Fee Related
- 2001-12-12 CN CNB011456795A patent/CN1181074C/zh not_active Expired - Fee Related
- 2001-12-12 KR KR1020010078510A patent/KR20020046226A/ko not_active Withdrawn
-
2003
- 2003-02-06 US US10/359,244 patent/US7115742B2/en not_active Expired - Lifetime
-
2008
- 2008-12-10 JP JP2008314159A patent/JP2009102347A/ja active Pending
- 2008-12-10 JP JP2008314160A patent/JP5086230B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ES2249652T3 (es) | 2006-04-01 |
| JP5086230B2 (ja) | 2012-11-28 |
| ATE297930T1 (de) | 2005-07-15 |
| CN1181074C (zh) | 2004-12-22 |
| ES2243380T3 (es) | 2005-12-01 |
| DE50106512D1 (de) | 2005-07-21 |
| EP1359151B1 (de) | 2015-06-03 |
| ES2544744T3 (es) | 2015-09-03 |
| US7115742B2 (en) | 2006-10-03 |
| JP2002284784A (ja) | 2002-10-03 |
| EP1215211B1 (de) | 2005-06-15 |
| ATE304544T1 (de) | 2005-09-15 |
| KR20020046226A (ko) | 2002-06-20 |
| EP1215211A1 (de) | 2002-06-19 |
| DE50107448D1 (de) | 2005-10-20 |
| EP1338598B1 (de) | 2005-09-14 |
| EP1338598A1 (de) | 2003-08-27 |
| US20020107394A1 (en) | 2002-08-08 |
| EP1359151A1 (de) | 2003-11-05 |
| US20030139598A1 (en) | 2003-07-24 |
| CN1362411A (zh) | 2002-08-07 |
| US6562971B2 (en) | 2003-05-13 |
| JP2009102348A (ja) | 2009-05-14 |
| JP4319798B2 (ja) | 2009-08-26 |
| JP2009102347A (ja) | 2009-05-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1215211B1 (de) | Verfahren zur Herstellung von Triethylendiamin (TEDA) | |
| JP2002284784A5 (https=) | ||
| WO2006114417A2 (de) | Verfahren zur herstellung von ethylenaminen | |
| DE69705805T2 (de) | Herstellung von Triethylendiaminen mit deaktivierten Oberflächensäurengehaltzeolithkatalysatoren | |
| WO2005123256A1 (de) | 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) | |
| DE3903622A1 (de) | Verfahren zur herstellung von 1,4-diazabicyclo-2,2,2-octan | |
| EP1406904B1 (de) | Verfahren zur selektiven synthese von triethylendiamin | |
| EP1272492B1 (de) | Verfahren zur herstellung von triethylendiamin unter einsatz von ethylendiamin | |
| DE10326137A1 (de) | 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) | |
| EP1462165A1 (de) | Verfahren zur Herstellung von Alkylaminen und zur Erhöhung der Hydroaminierungsaktivität von calcinierten zeolithischen Katalysatoren | |
| DE3801106A1 (de) | Verfahren zur herstellung von phenylethanolen | |
| DE3823160A1 (de) | Verfahren zur herstellung von 1,4-diazabicyclo-2,2,2-octanen | |
| DE3702483A1 (de) | Verfahren zur herstellung von ketonen | |
| DE3715753A1 (de) | Verfahren zur herstellung von 1,4-diazabicyclo(2,2,2)-octanen | |
| EP2155661A1 (de) | Verfahren zur herstellung von nitrilen | |
| DE102004013588A1 (de) | Verfahren zur Herstellung von Triethylendiamin aus Monoethanolamin |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |