DD300541A5 - Aminkatalyse unter verwendung von metallphosphat-katalysatoren mit zyklischer struktur - Google Patents

Aminkatalyse unter verwendung von metallphosphat-katalysatoren mit zyklischer struktur Download PDF

Info

Publication number: DD300541A5
Authority: DD; German Democratic Republic
Prior art keywords: group; metal; catalyst; mixture; amino compound
Prior art date: 1989-08-08

Application number

DD343295A

Other languages

German (de)

English (en)

Original Assignee

Union Carbide Chem Plastic

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.)

1989-08-08

Filing date

1990-08-07

Publication date

1992-06-17

1990-08-07 Application filed by Union Carbide Chem Plastic filed Critical Union Carbide Chem Plastic

1992-06-17 Publication of DD300541A5 publication Critical patent/DD300541A5/de

Links

239000003054 catalyst Substances 0.000 title claims abstract description 253
229910001463 metal phosphate Inorganic materials 0.000 title claims abstract description 86
-1 AMINO Chemical class 0.000 title claims abstract description 63
238000006555 catalytic reaction Methods 0.000 title 1
238000000034 method Methods 0.000 claims abstract description 93
238000009833 condensation Methods 0.000 claims abstract description 76
230000005494 condensation Effects 0.000 claims abstract description 74
239000000203 mixture Substances 0.000 claims abstract description 64
125000004122 cyclic group Chemical group 0.000 claims abstract description 52
FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims abstract description 44
230000008569 process Effects 0.000 claims abstract description 43
VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims abstract description 42
125000002015 acyclic group Chemical group 0.000 claims abstract description 38
150000001412 amines Chemical class 0.000 claims abstract description 23
238000002360 preparation method Methods 0.000 claims abstract description 12
229910052751 metal Inorganic materials 0.000 claims description 85
239000002184 metal Substances 0.000 claims description 85
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 62
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 56
150000004706 metal oxides Chemical class 0.000 claims description 56
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 42
229910044991 metal oxide Inorganic materials 0.000 claims description 36
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 31
229910021529 ammonia Inorganic materials 0.000 claims description 28
150000002739 metals Chemical class 0.000 claims description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 21
239000000126 substance Substances 0.000 claims description 21
239000000463 material Substances 0.000 claims description 20
MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 claims description 20
239000002253 acid Substances 0.000 claims description 17
HXMVNCMPQGPRLN-UHFFFAOYSA-N 2-hydroxyputrescine Chemical compound NCCC(O)CN HXMVNCMPQGPRLN-UHFFFAOYSA-N 0.000 claims description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 15
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 14
BETVNUCOOCCCIO-UHFFFAOYSA-N n-(2-dimethoxyphosphinothioylsulfanylethyl)acetamide Chemical compound COP(=S)(OC)SCCNC(C)=O BETVNUCOOCCCIO-UHFFFAOYSA-N 0.000 claims description 14
239000010936 titanium Substances 0.000 claims description 13
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 12
ZHBOFZNNPZNWGB-UHFFFAOYSA-N 9,10-bis(phenylethynyl)anthracene Chemical compound C1=CC=CC=C1C#CC(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C#CC1=CC=CC=C1 ZHBOFZNNPZNWGB-UHFFFAOYSA-N 0.000 claims description 11
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 11
239000007791 liquid phase Substances 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 10
UGTZMIPZNRIWHX-UHFFFAOYSA-K sodium trimetaphosphate Chemical compound [Na+].[Na+].[Na+].[O-]P1(=O)OP([O-])(=O)OP([O-])(=O)O1 UGTZMIPZNRIWHX-UHFFFAOYSA-K 0.000 claims description 10
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 9
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 9
229920000388 Polyphosphate Polymers 0.000 claims description 9
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 9
239000001205 polyphosphate Substances 0.000 claims description 9
235000011176 polyphosphates Nutrition 0.000 claims description 9
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 8
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 8
125000005341 metaphosphate group Chemical group 0.000 claims description 8
229910052726 zirconium Inorganic materials 0.000 claims description 8
239000011651 chromium Substances 0.000 claims description 7
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 7
239000000377 silicon dioxide Substances 0.000 claims description 7
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 6
239000010937 tungsten Substances 0.000 claims description 6
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 6
229910052721 tungsten Inorganic materials 0.000 claims description 6
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 5
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 5
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 5
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 5
229910052782 aluminium Inorganic materials 0.000 claims description 5
229910052787 antimony Inorganic materials 0.000 claims description 5
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 5
229910052785 arsenic Inorganic materials 0.000 claims description 5
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 5
229910052797 bismuth Inorganic materials 0.000 claims description 5
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 5
239000012876 carrier material Substances 0.000 claims description 5
229910052804 chromium Inorganic materials 0.000 claims description 5
229910052732 germanium Inorganic materials 0.000 claims description 5
GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 5
229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
239000011707 mineral Substances 0.000 claims description 5
239000011733 molybdenum Substances 0.000 claims description 5
229910052750 molybdenum Inorganic materials 0.000 claims description 5
229910052758 niobium Inorganic materials 0.000 claims description 5
239000010955 niobium Substances 0.000 claims description 5
GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims description 5
229910052710 silicon Inorganic materials 0.000 claims description 5
239000010703 silicon Substances 0.000 claims description 5
229910052715 tantalum Inorganic materials 0.000 claims description 5
GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims description 5
229910052718 tin Inorganic materials 0.000 claims description 5
229910052719 titanium Inorganic materials 0.000 claims description 5
239000012808 vapor phase Substances 0.000 claims description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 4
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
229910052796 boron Inorganic materials 0.000 claims description 4
229910017052 cobalt Inorganic materials 0.000 claims description 4
239000010941 cobalt Substances 0.000 claims description 4
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 4
229910052733 gallium Inorganic materials 0.000 claims description 4
229910052738 indium Inorganic materials 0.000 claims description 4
APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims description 4
229910052742 iron Inorganic materials 0.000 claims description 4
229910052746 lanthanum Inorganic materials 0.000 claims description 4
150000008298 phosphoramidates Chemical class 0.000 claims description 4
229910052706 scandium Inorganic materials 0.000 claims description 4
SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 claims description 4
235000019832 sodium triphosphate Nutrition 0.000 claims description 4
229910052727 yttrium Inorganic materials 0.000 claims description 4
VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 claims description 4
229910052725 zinc Inorganic materials 0.000 claims description 4
239000011701 zinc Substances 0.000 claims description 4
HVOBSBRYQIYZNY-UHFFFAOYSA-N 2-[2-(2-aminoethylamino)ethylamino]ethanol Chemical compound NCCNCCNCCO HVOBSBRYQIYZNY-UHFFFAOYSA-N 0.000 claims description 3
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 3
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 3
229910052765 Lutetium Inorganic materials 0.000 claims description 3
229910052769 Ytterbium Inorganic materials 0.000 claims description 3
229910052793 cadmium Inorganic materials 0.000 claims description 3
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 3
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 3
235000011180 diphosphates Nutrition 0.000 claims description 3
229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 3
FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims description 3
OHSVLFRHMCKCQY-UHFFFAOYSA-N lutetium atom Chemical compound [Lu] OHSVLFRHMCKCQY-UHFFFAOYSA-N 0.000 claims description 3
229910052759 nickel Inorganic materials 0.000 claims description 3
239000012071 phase Substances 0.000 claims description 3
NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 claims description 3
239000000470 constituent Substances 0.000 claims description 2
239000012530 fluid Substances 0.000 claims description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
150000003141 primary amines Chemical class 0.000 claims description 2
150000003335 secondary amines Chemical class 0.000 claims description 2
150000003512 tertiary amines Chemical class 0.000 claims description 2
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 2
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims 10
LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 claims 3
SOIAEOTUSNFHMI-UHFFFAOYSA-N 2-(2-aminoethylamino)ethane-1,1-diol Chemical compound NCCNCC(O)O SOIAEOTUSNFHMI-UHFFFAOYSA-N 0.000 claims 2
YTSNVWMTVVGZTI-UHFFFAOYSA-N 2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethanol Chemical compound NCCNCCNCCNCCO YTSNVWMTVVGZTI-UHFFFAOYSA-N 0.000 claims 2
229910052684 Cerium Inorganic materials 0.000 claims 2
229910052688 Gadolinium Inorganic materials 0.000 claims 2
ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 claims 2
UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 claims 2
XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims 1
RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims 1
UDEJEOLNSNYQSX-UHFFFAOYSA-J tetrasodium;2,4,6,8-tetraoxido-1,3,5,7,2$l^{5},4$l^{5},6$l^{5},8$l^{5}-tetraoxatetraphosphocane 2,4,6,8-tetraoxide Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P1(=O)OP([O-])(=O)OP([O-])(=O)OP([O-])(=O)O1 UDEJEOLNSNYQSX-UHFFFAOYSA-J 0.000 claims 1
229910001928 zirconium oxide Inorganic materials 0.000 claims 1
LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 abstract description 20
239000011148 porous material Substances 0.000 description 72
229910010413 TiO 2 Inorganic materials 0.000 description 70
238000006243 chemical reaction Methods 0.000 description 58
239000008188 pellet Substances 0.000 description 42
239000002245 particle Substances 0.000 description 39
239000011734 sodium Substances 0.000 description 39
229910004298 SiO 2 Inorganic materials 0.000 description 32
229910052698 phosphorus Inorganic materials 0.000 description 25
239000011574 phosphorus Substances 0.000 description 25
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 24
150000001875 compounds Chemical class 0.000 description 24
239000000047 product Substances 0.000 description 24
239000000243 solution Substances 0.000 description 24
229910018072 Al 2 O 3 Inorganic materials 0.000 description 18
230000003197 catalytic effect Effects 0.000 description 16
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 14
OCUJLLGVOUDECM-UHFFFAOYSA-N dipivefrin Chemical compound CNCC(O)C1=CC=C(OC(=O)C(C)(C)C)C(OC(=O)C(C)(C)C)=C1 OCUJLLGVOUDECM-UHFFFAOYSA-N 0.000 description 13
229920000768 polyamine Polymers 0.000 description 13
235000011007 phosphoric acid Nutrition 0.000 description 12
239000000376 reactant Substances 0.000 description 12
229910019142 PO4 Inorganic materials 0.000 description 11
235000021317 phosphate Nutrition 0.000 description 11
238000004519 manufacturing process Methods 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000004408 titanium dioxide Substances 0.000 description 9
125000000217 alkyl group Chemical group 0.000 description 8
239000007795 chemical reaction product Substances 0.000 description 8
239000007787 solid Substances 0.000 description 8
239000003377 acid catalyst Substances 0.000 description 7
ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical compound O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 description 7
150000008064 anhydrides Chemical class 0.000 description 7
238000006482 condensation reaction Methods 0.000 description 7
150000003016 phosphoric acids Chemical class 0.000 description 7
229910052708 sodium Inorganic materials 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 6
230000002378 acidificating effect Effects 0.000 description 6
238000005342 ion exchange Methods 0.000 description 6
239000010452 phosphate Substances 0.000 description 6
230000000704 physical effect Effects 0.000 description 6
229920001281 polyalkylene Polymers 0.000 description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
238000001035 drying Methods 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000011777 magnesium Substances 0.000 description 5
150000003013 phosphoric acid derivatives Chemical class 0.000 description 5
229910001495 sodium tetrafluoroborate Inorganic materials 0.000 description 5
241000894007 species Species 0.000 description 5
150000003467 sulfuric acid derivatives Chemical class 0.000 description 5
ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
230000009615 deamination Effects 0.000 description 4
238000006481 deamination reaction Methods 0.000 description 4
MRELNEQAGSRDBK-UHFFFAOYSA-N lanthanum(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[La+3].[La+3] MRELNEQAGSRDBK-UHFFFAOYSA-N 0.000 description 4
239000000395 magnesium oxide Substances 0.000 description 4
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 4
235000010755 mineral Nutrition 0.000 description 4
229910003455 mixed metal oxide Inorganic materials 0.000 description 4
229910000403 monosodium phosphate Inorganic materials 0.000 description 4
235000019799 monosodium phosphate Nutrition 0.000 description 4
210000000056 organ Anatomy 0.000 description 4
239000002002 slurry Substances 0.000 description 4
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 4
229910020599 Co 3 O 4 Inorganic materials 0.000 description 3
229910021193 La 2 O 3 Inorganic materials 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
239000000654 additive Substances 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
150000001768 cations Chemical class 0.000 description 3
238000010924 continuous production Methods 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
239000012043 crude product Substances 0.000 description 3
NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 3
235000019820 disodium diphosphate Nutrition 0.000 description 3
GYQBBRRVRKFJRG-UHFFFAOYSA-L disodium pyrophosphate Chemical compound [Na+].[Na+].OP([O-])(=O)OP(O)([O-])=O GYQBBRRVRKFJRG-UHFFFAOYSA-L 0.000 description 3
238000009826 distribution Methods 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
230000002349 favourable effect Effects 0.000 description 3
150000002334 glycols Chemical class 0.000 description 3
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical class [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 3
238000011065 in-situ storage Methods 0.000 description 3
229910052747 lanthanoid Inorganic materials 0.000 description 3
150000002602 lanthanoids Chemical class 0.000 description 3
239000007788 liquid Substances 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000002994 raw material Substances 0.000 description 3
239000012429 reaction media Substances 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
239000011593 sulfur Substances 0.000 description 3
ZCUFMDLYAMJYST-UHFFFAOYSA-N thorium dioxide Chemical compound O=[Th]=O ZCUFMDLYAMJYST-UHFFFAOYSA-N 0.000 description 3
XIOUDVJTOYVRTB-UHFFFAOYSA-N 1-(1-adamantyl)-3-aminothiourea Chemical compound C1C(C2)CC3CC2CC1(NC(=S)NN)C3 XIOUDVJTOYVRTB-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
239000004254 Ammonium phosphate Substances 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
235000001855 Portulaca oleracea Nutrition 0.000 description 2
244000234609 Portulaca oleracea Species 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
229910052768 actinide Inorganic materials 0.000 description 2
150000001255 actinides Chemical class 0.000 description 2
150000003973 alkyl amines Chemical class 0.000 description 2
125000003368 amide group Chemical group 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
229910000148 ammonium phosphate Inorganic materials 0.000 description 2
235000019289 ammonium phosphates Nutrition 0.000 description 2
229910000379 antimony sulfate Inorganic materials 0.000 description 2
MVMLTMBYNXHXFI-UHFFFAOYSA-H antimony(3+);trisulfate Chemical compound [Sb+3].[Sb+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O MVMLTMBYNXHXFI-UHFFFAOYSA-H 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
KQHXBDOEECKORE-UHFFFAOYSA-L beryllium sulfate Chemical compound [Be+2].[O-]S([O-])(=O)=O KQHXBDOEECKORE-UHFFFAOYSA-L 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
YZYDPPZYDIRSJT-UHFFFAOYSA-K boron phosphate Chemical compound [B+3].[O-]P([O-])([O-])=O YZYDPPZYDIRSJT-UHFFFAOYSA-K 0.000 description 2
229910000149 boron phosphate Inorganic materials 0.000 description 2
AZSFNUJOCKMOGB-UHFFFAOYSA-N cyclotriphosphoric acid Chemical compound OP1(=O)OP(O)(=O)OP(O)(=O)O1 AZSFNUJOCKMOGB-UHFFFAOYSA-N 0.000 description 2
MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 2
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000000499 gel Substances 0.000 description 2
229910052735 hafnium Inorganic materials 0.000 description 2
VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 2
125000005842 heteroatom Chemical group 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
238000005470 impregnation Methods 0.000 description 2
GJKFIJKSBFYMQK-UHFFFAOYSA-N lanthanum(3+);trinitrate;hexahydrate Chemical compound O.O.O.O.O.O.[La+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O GJKFIJKSBFYMQK-UHFFFAOYSA-N 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
QUWPZPLTANKXAM-UHFFFAOYSA-N niobium(5+) Chemical compound [Nb+5] QUWPZPLTANKXAM-UHFFFAOYSA-N 0.000 description 2
150000002895 organic esters Chemical class 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
AVFBYUADVDVJQL-UHFFFAOYSA-N phosphoric acid;trioxotungsten;hydrate Chemical compound O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O AVFBYUADVDVJQL-UHFFFAOYSA-N 0.000 description 2
150000003018 phosphorus compounds Chemical class 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
229920005862 polyol Polymers 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
239000011949 solid catalyst Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
VKFFEYLSKIYTSJ-UHFFFAOYSA-N tetraazanium;phosphonato phosphate Chemical group [NH4+].[NH4+].[NH4+].[NH4+].[O-]P([O-])(=O)OP([O-])([O-])=O VKFFEYLSKIYTSJ-UHFFFAOYSA-N 0.000 description 2
LLZRNZOLAXHGLL-UHFFFAOYSA-J titanic acid Chemical compound O[Ti](O)(O)O LLZRNZOLAXHGLL-UHFFFAOYSA-J 0.000 description 2
230000001131 transforming effect Effects 0.000 description 2
229910052720 vanadium Inorganic materials 0.000 description 2
LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 2
DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
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
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
229910000619 316 stainless steel Inorganic materials 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
229910015902 Bi 2 O 3 Inorganic materials 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
241001669680 Dormitator maculatus Species 0.000 description 1
229910052692 Dysprosium Inorganic materials 0.000 description 1
229910052691 Erbium Inorganic materials 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
229910005191 Ga 2 O 3 Inorganic materials 0.000 description 1
229910052689 Holmium Inorganic materials 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
229910018068 Li 2 O Inorganic materials 0.000 description 1
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 1
UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 description 1
NIWILFHYUXWOAE-UHFFFAOYSA-K N1C=CC=C1.P(=O)([O-])([O-])[O-].[Na+].[Na+].[Na+] Chemical compound N1C=CC=C1.P(=O)([O-])([O-])[O-].[Na+].[Na+].[Na+] NIWILFHYUXWOAE-UHFFFAOYSA-K 0.000 description 1
229910020808 NaBF Inorganic materials 0.000 description 1
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
229910006404 SnO 2 Inorganic materials 0.000 description 1
101150116986 THPO gene Proteins 0.000 description 1
229910052771 Terbium Inorganic materials 0.000 description 1
229910052776 Thorium Inorganic materials 0.000 description 1
229910052775 Thulium Inorganic materials 0.000 description 1
XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 1
XRPPFLNCRKRKNK-UHFFFAOYSA-N [P].C=C Chemical group [P].C=C XRPPFLNCRKRKNK-UHFFFAOYSA-N 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 1
PYCBFXMWPVRTCC-UHFFFAOYSA-N ammonium metaphosphate Chemical group N.OP(=O)=O PYCBFXMWPVRTCC-UHFFFAOYSA-N 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
LMLCHSMXNLEULM-UHFFFAOYSA-N azane;methanamine;methanol Chemical compound N.NC.OC LMLCHSMXNLEULM-UHFFFAOYSA-N 0.000 description 1
UBUYAZUEYAXMBU-UHFFFAOYSA-N azane;n,n-dimethylmethanamine Chemical compound N.CN(C)C UBUYAZUEYAXMBU-UHFFFAOYSA-N 0.000 description 1
229910001570 bauxite Inorganic materials 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
229910052790 beryllium Inorganic materials 0.000 description 1
ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003729 cation exchange resin Substances 0.000 description 1
229910052729 chemical element Inorganic materials 0.000 description 1
230000000295 complement effect Effects 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
150000001923 cyclic compounds Chemical class 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
229910000397 disodium phosphate Inorganic materials 0.000 description 1
235000019800 disodium phosphate Nutrition 0.000 description 1
238000004821 distillation Methods 0.000 description 1
KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 description 1
XBRDBODLCHKXHI-UHFFFAOYSA-N epolamine Chemical compound OCCN1CCCC1 XBRDBODLCHKXHI-UHFFFAOYSA-N 0.000 description 1
UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical compound [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000002979 fabric softener Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000003747 fuel oil additive Substances 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
KJZYNXUDTRRSPN-UHFFFAOYSA-N holmium atom Chemical compound [Ho] KJZYNXUDTRRSPN-UHFFFAOYSA-N 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229910000358 iron sulfate Inorganic materials 0.000 description 1
BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
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 1
238000011031 large-scale manufacturing process Methods 0.000 description 1
238000002386 leaching Methods 0.000 description 1
238000011068 loading method Methods 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
229910001960 metal nitrate Inorganic materials 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
229910000476 molybdenum oxide Inorganic materials 0.000 description 1
239000000178 monomer Substances 0.000 description 1
229910000484 niobium oxide Inorganic materials 0.000 description 1
URLJKFSTXLNXLG-UHFFFAOYSA-N niobium(5+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Nb+5].[Nb+5] URLJKFSTXLNXLG-UHFFFAOYSA-N 0.000 description 1
125000004433 nitrogen atom Chemical group N* 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
150000002894 organic compounds Chemical class 0.000 description 1
PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
150000002926 oxygen Chemical class 0.000 description 1
SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical class [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 description 1
235000012771 pancakes Nutrition 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
229920000166 polytrimethylene carbonate Polymers 0.000 description 1
238000012545 processing Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
230000005588 protonation Effects 0.000 description 1
230000001698 pyrogenic effect Effects 0.000 description 1
229940005657 pyrophosphoric acid Drugs 0.000 description 1
229910052761 rare earth metal Inorganic materials 0.000 description 1
150000002910 rare earth metals Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
238000004064 recycling Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
238000002791 soaking Methods 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
235000011008 sodium phosphates Nutrition 0.000 description 1
VLDHWMAJBNWALQ-UHFFFAOYSA-M sodium;1,3-benzothiazol-3-ide-2-thione Chemical compound [Na+].C1=CC=C2SC([S-])=NC2=C1 VLDHWMAJBNWALQ-UHFFFAOYSA-M 0.000 description 1
239000000758 substrate Substances 0.000 description 1
150000003464 sulfur compounds Chemical class 0.000 description 1
GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
238000012360 testing method Methods 0.000 description 1
229910003452 thorium oxide Inorganic materials 0.000 description 1
230000009466 transformation Effects 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 description 1
229910001930 tungsten oxide Inorganic materials 0.000 description 1
229910001935 vanadium oxide Inorganic materials 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
ZXAUZSQITFJWPS-UHFFFAOYSA-J zirconium(4+);disulfate Chemical compound [Zr+4].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O ZXAUZSQITFJWPS-UHFFFAOYSA-J 0.000 description 1
229910000350 zirconium(IV) sulfate Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
- C07C209/16—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/16—Phosphorus; Compounds thereof containing oxygen, i.e. acids, anhydrides and their derivates with N, S, B or halogens without carriers or on carriers based on C, Si, Al or Zr; also salts of Si, Al and Zr
- B01J27/18—Phosphorus; Compounds thereof containing oxygen, i.e. acids, anhydrides and their derivates with N, S, B or halogens without carriers or on carriers based on C, Si, Al or Zr; also salts of Si, Al and Zr with metals other than Al or Zr

Landscapes

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

DD343295A 1989-08-08 1990-08-07 Aminkatalyse unter verwendung von metallphosphat-katalysatoren mit zyklischer struktur DD300541A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/390,706 US5202492A (en)	1989-08-08	1989-08-08	Amines catalysis using metallic phosphate condensation catalysts having a cyclic structure

Publications (1)

Publication Number	Publication Date
DD300541A5 true DD300541A5 (de)	1992-06-17

Family

ID=23543580

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD343295A DD300541A5 (de)	1989-08-08	1990-08-07	Aminkatalyse unter verwendung von metallphosphat-katalysatoren mit zyklischer struktur

Country Status (9)

Country	Link
US (1)	US5202492A (fr)
EP (1)	EP0412613A3 (fr)
JP (1)	JPH0386847A (fr)
KR (1)	KR910004534A (fr)
CN (1)	CN1052662A (fr)
AU (1)	AU6021090A (fr)
CA (1)	CA2022776A1 (fr)
DD (1)	DD300541A5 (fr)
ZA (1)	ZA906225B (fr)

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US5225599A (en) *	1990-03-30	1993-07-06	Union Carbide Chemicals & Plastics Technology Corporation	Selective production of linear triethylenetetramine and aminoethylethanolamine
US5231230A (en) *	1990-03-30	1993-07-27	Union Carbide Chemicals & Plastics Technology Corporation	Selective production of diethylenetriamine
US5220071A (en) *	1990-03-30	1993-06-15	Union Carbide Chemicals & Plastics Technology Corporation	Selective production of pentaethylenehexamine and hydroxyethyltriethylenetetramine
US5225598A (en) *	1990-03-30	1993-07-06	Union Carbide Chemicals & Plastics Technology Corporation	Selective production of linear pentaethylenehexamine and hydroxyethyldiethylenetriamine
KR910016811A (ko) *	1990-03-30	1991-11-05	티모시 엔. 비숍	고급 폴리알킬렌 폴리아민 및 하이드록실-함유 폴리알킬렌 폴리아민의 선택적인 제조
US5362700A (en) *	1992-10-08	1994-11-08	Union Carbide Chemicals & Plastics Technology Corporation	Catalysts and process of making same for the production of linear polyamines
DE19612783A1 (de) *	1996-03-29	1997-10-02	Degussa	Phosphorsäurekatalysator und seine Verwendung
DE10261195A1 (de)	2002-12-20	2004-07-01	Basf Ag	Verfahren zur Herstellung eines symmetrischen sekundären Amins
EP1887524A4 (fr) *	2005-06-02	2012-02-15	Tencent Tech Shenzhen Co Ltd	Procede d´affichage d´animation et son systeme

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US2073671A (en) *	1931-04-02	1937-03-16	Rohm & Haas	Manufacture of amines
US2467205A (en) *	1944-02-25	1949-04-12	Du Pont	Process for producing piperazine
US4036881A (en) *	1975-06-02	1977-07-19	Texaco Development Corporation	Preparation of polyalkylene polyamines
US4044053A (en) *	1975-06-02	1977-08-23	Texaco Development Corporation	Preparation of polyalkylene polyamines
US4324917A (en) *	1980-08-28	1982-04-13	Texaco Inc.	Preparation of polyalkylene polyamines
US4314083A (en) *	1980-10-03	1982-02-02	Air Products And Chemicals, Inc.	Preparation of linear polyalkylene polyamines
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1989
- 1989-08-08 US US07/390,706 patent/US5202492A/en not_active Expired - Fee Related
1990
- 1990-08-07 CA CA002022776A patent/CA2022776A1/fr not_active Abandoned
- 1990-08-07 DD DD343295A patent/DD300541A5/de unknown
- 1990-08-07 KR KR1019900012073A patent/KR910004534A/ko not_active Ceased
- 1990-08-07 AU AU60210/90A patent/AU6021090A/en not_active Abandoned
- 1990-08-07 ZA ZA906225A patent/ZA906225B/xx unknown
- 1990-08-07 EP EP19900202135 patent/EP0412613A3/fr not_active Withdrawn
- 1990-08-07 CN CN90107594A patent/CN1052662A/zh active Pending
- 1990-08-08 JP JP2210111A patent/JPH0386847A/ja active Pending

Also Published As

Publication number	Publication date
US5202492A (en)	1993-04-13
ZA906225B (en)	1991-05-29
EP0412613A3 (fr)	1991-03-27
EP0412613A2 (fr)	1991-02-13
CN1052662A (zh)	1991-07-03
CA2022776A1 (fr)	1991-02-09
JPH0386847A (ja)	1991-04-11
AU6021090A (en)	1991-02-14
KR910004534A (ko)	1991-03-28

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DE69029020T2 (de)	1997-03-20	Verfahren zur Herstellung von Polyalkylenpolyaminen
DE68912750T2 (de)	1994-05-11	Produktion von Ethanolaminen durch Aminierung von Ethylenoxid mit durch Säure aktiviertem Ton.
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DE3688603T2 (de)	1993-10-07	Katalytisch hergestellte Polyalkylenpolyamine.
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WO1991015457A1 (fr)	1991-10-17	Production selective de polyamines de polyalkylene superieur et de polyamines de polyalkylene contenant de l'hydroxyle
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