CA1336717C - Methode de preparation d'amines, d'hydroxylamines et d'aziridines - Google Patents

Methode de preparation d'amines, d'hydroxylamines et d'aziridines

Info

Publication number: CA1336717C
Authority: CA; Canada
Prior art keywords: present; mole; points; value; aluminum
Prior art date: 1987-12-18
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.): Expired - Fee Related

Application number

CA000586709A

Other languages

English (en)

Inventor

Kurt Damar Olson

Steven William Kaiser

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Union Carbide Corp

Original Assignee

Union Carbide Corp

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.)

1987-12-18

Filing date

1988-12-21

Publication date

1995-08-15

1987-12-18 Priority to US07/134,863 priority Critical patent/US5120860A/en

1987-12-18 Priority claimed from US07/134,863 external-priority patent/US5120860A/en

1988-12-16 Priority to EP89901980A priority patent/EP0358736A1/fr

1988-12-16 Priority to DE3851327T priority patent/DE3851327T2/de

1988-12-16 Priority to PCT/US1988/004456 priority patent/WO1989005797A2/fr

1988-12-16 Priority to PCT/US1988/004455 priority patent/WO1989006229A1/fr

1988-12-16 Priority to EP89901223A priority patent/EP0346443B1/fr

1988-12-21 Application filed by Union Carbide Corp filed Critical Union Carbide Corp

1988-12-21 Priority to CA000586709A priority patent/CA1336717C/fr

1995-08-15 Publication of CA1336717C publication Critical patent/CA1336717C/fr

1995-08-15 Application granted granted Critical

2012-08-15 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 219
230000008569 process Effects 0.000 title claims description 123
150000001412 amines Chemical class 0.000 title claims description 14
150000001541 aziridines Chemical class 0.000 title abstract description 6
238000004519 manufacturing process Methods 0.000 title description 11
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 title description 2
239000002808 molecular sieve Substances 0.000 claims abstract description 299
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims abstract description 299
229910052782 aluminium Inorganic materials 0.000 claims abstract description 227
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 213
-1 cyclic alkylamines Chemical class 0.000 claims abstract description 104
229910052710 silicon Inorganic materials 0.000 claims abstract description 96
239000010703 silicon Substances 0.000 claims abstract description 96
239000007858 starting material Substances 0.000 claims abstract description 32
125000004122 cyclic group Chemical group 0.000 claims abstract description 12
125000002015 acyclic group Chemical group 0.000 claims abstract description 6
239000000203 mixture Substances 0.000 claims description 434
239000003795 chemical substances by application Substances 0.000 claims description 266
229910052698 phosphorus Inorganic materials 0.000 claims description 208
239000011574 phosphorus Chemical group 0.000 claims description 202
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 200
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 156
239000000047 product Substances 0.000 claims description 127
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 95
238000006243 chemical reaction Methods 0.000 claims description 90
239000011148 porous material Substances 0.000 claims description 90
239000000126 substance Substances 0.000 claims description 79
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 75
239000000377 silicon dioxide Substances 0.000 claims description 75
239000000463 material Substances 0.000 claims description 63
235000012239 silicon dioxide Nutrition 0.000 claims description 57
229910052906 cristobalite Inorganic materials 0.000 claims description 56
229910052905 tridymite Inorganic materials 0.000 claims description 56
229910052681 coesite Inorganic materials 0.000 claims description 55
229910052682 stishovite Inorganic materials 0.000 claims description 55
229910052719 titanium Inorganic materials 0.000 claims description 48
239000010936 titanium Substances 0.000 claims description 48
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 47
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 42
239000011777 magnesium Substances 0.000 claims description 40
229910017052 cobalt Inorganic materials 0.000 claims description 38
239000010941 cobalt Substances 0.000 claims description 38
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 38
229910052749 magnesium Inorganic materials 0.000 claims description 37
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 36
150000001768 cations Chemical class 0.000 claims description 36
229910052742 iron Inorganic materials 0.000 claims description 36
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 33
229910052804 chromium Inorganic materials 0.000 claims description 33
239000011651 chromium Substances 0.000 claims description 33
229910052732 germanium Inorganic materials 0.000 claims description 33
GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 33
229910052785 arsenic Inorganic materials 0.000 claims description 32
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 31
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 31
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 31
229910052796 boron Inorganic materials 0.000 claims description 31
229910052744 lithium Inorganic materials 0.000 claims description 31
239000011701 zinc Substances 0.000 claims description 31
229910052725 zinc Inorganic materials 0.000 claims description 30
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 29
229910052757 nitrogen Inorganic materials 0.000 claims description 27
NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 26
GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 24
229910052733 gallium Inorganic materials 0.000 claims description 24
229910052790 beryllium Inorganic materials 0.000 claims description 23
ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 claims description 23
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 23
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 22
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 20
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 15
239000000470 constituent Substances 0.000 claims description 14
YBMRDBCBODYGJE-UHFFFAOYSA-N germanium dioxide Chemical compound O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 claims description 14
239000011572 manganese Substances 0.000 claims description 13
239000012159 carrier gas Substances 0.000 claims description 12
AYTAKQFHWFYBMA-UHFFFAOYSA-N chromium dioxide Chemical compound O=[Cr]=O AYTAKQFHWFYBMA-UHFFFAOYSA-N 0.000 claims description 12
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical class C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
229910052748 manganese Inorganic materials 0.000 claims description 10
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 9
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 9
239000007789 gas Substances 0.000 claims description 9
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical class NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 8
229910052720 vanadium Inorganic materials 0.000 claims description 8
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical class CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical class CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 6
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical class C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 6
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 6
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 5
OZDGMOYKSFPLSE-UHFFFAOYSA-N 2-Methylaziridine Chemical compound CC1CN1 OZDGMOYKSFPLSE-UHFFFAOYSA-N 0.000 claims description 4
229910021529 ammonia Inorganic materials 0.000 claims description 4
229910005534 GaO2 Inorganic materials 0.000 claims description 3
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical class C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 3
XXMBEHIWODXDTR-UHFFFAOYSA-N 1,2-diaminoethanol Chemical class NCC(N)O XXMBEHIWODXDTR-UHFFFAOYSA-N 0.000 claims description 2
101100011518 Arabidopsis thaliana ELP1 gene Proteins 0.000 claims description 2
229910013504 M-O-M Inorganic materials 0.000 claims description 2
WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 claims description 2
101100501248 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) ELO2 gene Proteins 0.000 claims description 2
UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical class NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 claims description 2
239000007792 gaseous phase Substances 0.000 claims description 2
150000004885 piperazines Chemical class 0.000 claims description 2
IZEKFCXSFNUWAM-UHFFFAOYSA-N dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 claims 15
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims 4
LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims 4
LZYIDMKXGSDQMT-UHFFFAOYSA-N arsenic dioxide Inorganic materials [O][As]=O LZYIDMKXGSDQMT-UHFFFAOYSA-N 0.000 claims 2
239000010457 zeolite Substances 0.000 abstract description 23
239000011541 reaction mixture Substances 0.000 description 209
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 139
235000011007 phosphoric acid Nutrition 0.000 description 93
WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 83
230000000670 limiting effect Effects 0.000 description 78
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 77
229910001868 water Inorganic materials 0.000 description 75
239000008240 homogeneous mixture Substances 0.000 description 63
229910000147 aluminium phosphate Inorganic materials 0.000 description 60
239000007864 aqueous solution Substances 0.000 description 59
239000003153 chemical reaction reagent Substances 0.000 description 59
229910052751 metal Inorganic materials 0.000 description 57
239000002184 metal Substances 0.000 description 57
229940058401 polytetrafluoroethylene Drugs 0.000 description 56
239000004810 polytetrafluoroethylene Substances 0.000 description 56
239000013078 crystal Substances 0.000 description 54
241000894007 species Species 0.000 description 54
229920001343 polytetrafluoroethylene Polymers 0.000 description 53
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 52
150000001875 compounds Chemical class 0.000 description 47
239000000243 solution Substances 0.000 description 47
230000029087 digestion Effects 0.000 description 44
VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 44
SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 40
LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 40
BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 39
FYAMXEPQQLNQDM-UHFFFAOYSA-N Tris(1-aziridinyl)phosphine oxide Chemical compound C1CN1P(N1CC1)(=O)N1CC1 FYAMXEPQQLNQDM-UHFFFAOYSA-N 0.000 description 38
230000015572 biosynthetic process Effects 0.000 description 36
238000005216 hydrothermal crystallization Methods 0.000 description 36
230000000737 periodic effect Effects 0.000 description 32
238000001914 filtration Methods 0.000 description 31
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 30
239000004033 plastic Substances 0.000 description 30
230000002194 synthesizing effect Effects 0.000 description 30
239000003054 catalyst Substances 0.000 description 29
SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 29
239000000376 reactant Substances 0.000 description 29
229910001220 stainless steel Inorganic materials 0.000 description 29
239000010935 stainless steel Substances 0.000 description 29
239000003513 alkali Substances 0.000 description 28
238000005119 centrifugation Methods 0.000 description 28
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 27
VXAUWWUXCIMFIM-UHFFFAOYSA-M aluminum;oxygen(2-);hydroxide Chemical compound [OH-].[O-2].[Al+3] VXAUWWUXCIMFIM-UHFFFAOYSA-M 0.000 description 26
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 26
238000003786 synthesis reaction Methods 0.000 description 25
LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 24
229940073455 tetraethylammonium hydroxide Drugs 0.000 description 23
XIMAAVOQRXLRMW-UHFFFAOYSA-N 2-methyl-1-azabicyclo[2.2.2]octane hydrate Chemical compound O.C1CN2C(C)CC1CC2 XIMAAVOQRXLRMW-UHFFFAOYSA-N 0.000 description 22
DYJJOXPTDCNLEF-UHFFFAOYSA-N bicyclo[4.1.0]heptan-7-amine Chemical compound C1CCCC2C(N)C21 DYJJOXPTDCNLEF-UHFFFAOYSA-N 0.000 description 20
238000002425 crystallisation Methods 0.000 description 20
230000008025 crystallization Effects 0.000 description 19
FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 19
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 19
229940013085 2-diethylaminoethanol Drugs 0.000 description 18
KKCBUQHMOMHUOY-UHFFFAOYSA-N Na2O Inorganic materials [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 14
229910052783 alkali metal Inorganic materials 0.000 description 14
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 14
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 13
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 12
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 12
229910000323 aluminium silicate Inorganic materials 0.000 description 12
238000002156 mixing Methods 0.000 description 12
241000640882 Condea Species 0.000 description 11
COHDHYZHOPQOFD-UHFFFAOYSA-N arsenic pentoxide Inorganic materials O=[As](=O)O[As](=O)=O COHDHYZHOPQOFD-UHFFFAOYSA-N 0.000 description 11
230000018044 dehydration Effects 0.000 description 11
238000006297 dehydration reaction Methods 0.000 description 11
239000011369 resultant mixture Substances 0.000 description 11
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 10
125000000217 alkyl group Chemical group 0.000 description 10
238000001354 calcination Methods 0.000 description 10
125000004432 carbon atom Chemical group C* 0.000 description 10
WYYQVWLEPYFFLP-UHFFFAOYSA-K chromium(3+);triacetate Chemical compound [Cr+3].CC([O-])=O.CC([O-])=O.CC([O-])=O WYYQVWLEPYFFLP-UHFFFAOYSA-K 0.000 description 10
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 9
INEWUCPYEUEQTN-UHFFFAOYSA-N 3-(cyclohexylamino)-2-hydroxy-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(O)CNC1CCCCC1 INEWUCPYEUEQTN-UHFFFAOYSA-N 0.000 description 9
125000003118 aryl group Chemical group 0.000 description 9
239000007788 liquid Substances 0.000 description 9
239000012071 phase Substances 0.000 description 9
238000002360 preparation method Methods 0.000 description 9
150000003839 salts Chemical class 0.000 description 9
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 8
229910019142 PO4 Inorganic materials 0.000 description 8
229910021536 Zeolite Inorganic materials 0.000 description 8
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 8
230000000694 effects Effects 0.000 description 8
150000002500 ions Chemical class 0.000 description 8
150000002739 metals Chemical class 0.000 description 8
235000021317 phosphate Nutrition 0.000 description 8
150000003856 quaternary ammonium compounds Chemical class 0.000 description 8
150000001298 alcohols Chemical class 0.000 description 7
150000004703 alkoxides Chemical class 0.000 description 7
230000003993 interaction Effects 0.000 description 7
UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 7
239000011654 magnesium acetate Substances 0.000 description 7
229940069446 magnesium acetate Drugs 0.000 description 7
235000011285 magnesium acetate Nutrition 0.000 description 7
UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 7
OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 7
TWQULNDIKKJZPH-UHFFFAOYSA-K trilithium;phosphate Chemical compound [Li+].[Li+].[Li+].[O-]P([O-])([O-])=O TWQULNDIKKJZPH-UHFFFAOYSA-K 0.000 description 7
RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 6
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 6
238000007792 addition Methods 0.000 description 6
150000001340 alkali metals Chemical class 0.000 description 6
KQHXBDOEECKORE-UHFFFAOYSA-L beryllium sulfate Chemical compound [Be+2].[O-]S([O-])(=O)=O KQHXBDOEECKORE-UHFFFAOYSA-L 0.000 description 6
229940011182 cobalt acetate Drugs 0.000 description 6
QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 6
229910021513 gallium hydroxide Inorganic materials 0.000 description 6
229910000373 gallium sulfate Inorganic materials 0.000 description 6
229940071125 manganese acetate Drugs 0.000 description 6
150000002892 organic cations Chemical class 0.000 description 6
238000003756 stirring Methods 0.000 description 6
GXMNGLIMQIPFEB-UHFFFAOYSA-N tetraethoxygermane Chemical compound CCO[Ge](OCC)(OCC)OCC GXMNGLIMQIPFEB-UHFFFAOYSA-N 0.000 description 6
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
229910052787 antimony Inorganic materials 0.000 description 5
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
229910052593 corundum Inorganic materials 0.000 description 5
238000003795 desorption Methods 0.000 description 5
238000009826 distribution Methods 0.000 description 5
DNUARHPNFXVKEI-UHFFFAOYSA-K gallium(iii) hydroxide Chemical compound [OH-].[OH-].[OH-].[Ga+3] DNUARHPNFXVKEI-UHFFFAOYSA-K 0.000 description 5
SBDRYJMIQMDXRH-UHFFFAOYSA-N gallium;sulfuric acid Chemical compound [Ga].OS(O)(=O)=O SBDRYJMIQMDXRH-UHFFFAOYSA-N 0.000 description 5
238000011065 in-situ storage Methods 0.000 description 5
229910001386 lithium phosphate Inorganic materials 0.000 description 5
229910052760 oxygen Inorganic materials 0.000 description 5
239000001301 oxygen Substances 0.000 description 5
230000036961 partial effect Effects 0.000 description 5
150000003013 phosphoric acid derivatives Chemical class 0.000 description 5
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101100006982 Mus musculus Ppcdc gene Proteins 0.000 description 2
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239000007795 chemical reaction product Substances 0.000 description 2
IKZBVTPSNGOVRJ-UHFFFAOYSA-K chromium(iii) phosphate Chemical compound [Cr+3].[O-]P([O-])([O-])=O IKZBVTPSNGOVRJ-UHFFFAOYSA-K 0.000 description 2
239000012973 diazabicyclooctane Substances 0.000 description 2
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BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 2
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FVEFRICMTUKAML-UHFFFAOYSA-M sodium tetradecyl sulfate Chemical compound [Na+].CCCCC(CC)CCC(CC(C)C)OS([O-])(=O)=O FVEFRICMTUKAML-UHFFFAOYSA-M 0.000 description 2
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150000003624 transition metals Chemical class 0.000 description 2
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FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
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AWGBWLXGUPTXHF-UHFFFAOYSA-N 2,2,2-trifluoro-n-methyl-n-(2,2,2-trifluoroacetyl)acetamide Chemical compound FC(F)(F)C(=O)N(C)C(=O)C(F)(F)F AWGBWLXGUPTXHF-UHFFFAOYSA-N 0.000 description 1
HXMVNCMPQGPRLN-UHFFFAOYSA-N 2-hydroxyputrescine Chemical compound NCCC(O)CN HXMVNCMPQGPRLN-UHFFFAOYSA-N 0.000 description 1
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229910018516 Al—O Inorganic materials 0.000 description 1
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VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
241000269350 Anura Species 0.000 description 1
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
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OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
206010007269 Carcinogenicity Diseases 0.000 description 1
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XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 1
241001397173 Kali <angiosperm> Species 0.000 description 1
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WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
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230000009286 beneficial effect Effects 0.000 description 1
PPYIVKOTTQCYIV-UHFFFAOYSA-L beryllium;selenate Chemical compound [Be+2].[O-][Se]([O-])(=O)=O PPYIVKOTTQCYIV-UHFFFAOYSA-L 0.000 description 1
KQHXBDOEECKORE-UHFFFAOYSA-N beryllium;sulfuric acid Chemical compound [Be+2].OS(O)(=O)=O KQHXBDOEECKORE-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
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125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
230000007670 carcinogenicity Effects 0.000 description 1
231100000260 carcinogenicity Toxicity 0.000 description 1
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150000001805 chlorine compounds Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
229910000151 chromium(III) phosphate Inorganic materials 0.000 description 1
GFHNAMRJFCEERV-UHFFFAOYSA-L cobalt chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Co+2] GFHNAMRJFCEERV-UHFFFAOYSA-L 0.000 description 1
GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
229910000361 cobalt sulfate Inorganic materials 0.000 description 1
229940044175 cobalt sulfate Drugs 0.000 description 1
AVWLPUQJODERGA-UHFFFAOYSA-L cobalt(2+);diiodide Chemical compound [Co+2].[I-].[I-] AVWLPUQJODERGA-UHFFFAOYSA-L 0.000 description 1
BZRRQSJJPUGBAA-UHFFFAOYSA-L cobalt(ii) bromide Chemical compound Br[Co]Br BZRRQSJJPUGBAA-UHFFFAOYSA-L 0.000 description 1
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238000004939 coking Methods 0.000 description 1
239000002131 composite material Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
RKTYLMNFRDHKIL-UHFFFAOYSA-N copper;5,10,15,20-tetraphenylporphyrin-22,24-diide Chemical compound [Cu+2].C1=CC(C(=C2C=CC([N-]2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3[N-]2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 RKTYLMNFRDHKIL-UHFFFAOYSA-N 0.000 description 1
230000009615 deamination Effects 0.000 description 1
230000007423 decrease Effects 0.000 description 1
238000001212 derivatisation Methods 0.000 description 1
MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
229910000388 diammonium phosphate Inorganic materials 0.000 description 1
235000019838 diammonium phosphate Nutrition 0.000 description 1
RJYMRRJVDRJMJW-UHFFFAOYSA-L dibromomanganese Chemical compound Br[Mn]Br RJYMRRJVDRJMJW-UHFFFAOYSA-L 0.000 description 1
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238000010494 dissociation reaction Methods 0.000 description 1
230000005593 dissociations Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
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XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical group FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
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150000002430 hydrocarbons Chemical class 0.000 description 1
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229910010272 inorganic material Inorganic materials 0.000 description 1
239000011147 inorganic material Substances 0.000 description 1
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159000000014 iron salts Chemical class 0.000 description 1
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MVFCKEFYUDZOCX-UHFFFAOYSA-N iron(2+);dinitrate Chemical compound [Fe+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MVFCKEFYUDZOCX-UHFFFAOYSA-N 0.000 description 1
WVLDCUJMGWFHGE-UHFFFAOYSA-L iron(2+);sulfate;hexahydrate Chemical compound O.O.O.O.O.O.[Fe+2].[O-]S([O-])(=O)=O WVLDCUJMGWFHGE-UHFFFAOYSA-L 0.000 description 1
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229910001623 magnesium bromide Inorganic materials 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
BLQJIBCZHWBKSL-UHFFFAOYSA-L magnesium iodide Chemical compound [Mg+2].[I-].[I-] BLQJIBCZHWBKSL-UHFFFAOYSA-L 0.000 description 1
229910001641 magnesium iodide Inorganic materials 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
XKPKPGCRSHFTKM-UHFFFAOYSA-L magnesium;diacetate;tetrahydrate Chemical compound O.O.O.O.[Mg+2].CC([O-])=O.CC([O-])=O XKPKPGCRSHFTKM-UHFFFAOYSA-L 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
125000002950 monocyclic group Chemical group 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
150000004686 pentahydrates Chemical class 0.000 description 1
238000010587 phase diagram Methods 0.000 description 1
150000003018 phosphorus compounds Chemical class 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
238000005086 pumping Methods 0.000 description 1
238000004445 quantitative analysis Methods 0.000 description 1
150000004023 quaternary phosphonium compounds Chemical class 0.000 description 1
239000012066 reaction slurry Substances 0.000 description 1
230000007420 reactivation Effects 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
238000005070 sampling Methods 0.000 description 1
239000004576 sand Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
229910010271 silicon carbide Inorganic materials 0.000 description 1
150000003377 silicon compounds Chemical class 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
229910052712 strontium Inorganic materials 0.000 description 1
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
RBTVSNLYYIMMKS-UHFFFAOYSA-N tert-butyl 3-aminoazetidine-1-carboxylate;hydrochloride Chemical compound Cl.CC(C)(C)OC(=O)N1CC(N)C1 RBTVSNLYYIMMKS-UHFFFAOYSA-N 0.000 description 1
HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
MYXKPFMQWULLOH-UHFFFAOYSA-M tetramethylazanium;hydroxide;pentahydrate Chemical compound O.O.O.O.O.[OH-].C[N+](C)(C)C MYXKPFMQWULLOH-UHFFFAOYSA-M 0.000 description 1
GJSGYPDDPQRWPK-UHFFFAOYSA-N tetrapentylammonium Chemical compound CCCCC[N+](CCCCC)(CCCCC)CCCCC GJSGYPDDPQRWPK-UHFFFAOYSA-N 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
150000003657 tungsten Chemical class 0.000 description 1
229910001930 tungsten oxide Inorganic materials 0.000 description 1
238000005406 washing Methods 0.000 description 1
229960000314 zinc acetate Drugs 0.000 description 1
229940102001 zinc bromide Drugs 0.000 description 1
SRWMQSFFRFWREA-UHFFFAOYSA-M zinc formate Chemical compound [Zn+2].[O-]C=O SRWMQSFFRFWREA-UHFFFAOYSA-M 0.000 description 1
RZLVQBNCHSJZPX-UHFFFAOYSA-L zinc sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Zn+2].[O-]S([O-])(=O)=O RZLVQBNCHSJZPX-UHFFFAOYSA-L 0.000 description 1
GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/023—Preparation; Separation; Stabilisation; Use of additives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/64—Preparation of compounds containing amino groups bound to a carbon skeleton by disproportionation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/02—Preparation by ring-closure
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Silicates, Zeolites, And Molecular Sieves (AREA)

CA000586709A 1987-12-18 1988-12-21 Methode de preparation d'amines, d'hydroxylamines et d'aziridines Expired - Fee Related CA1336717C (fr)

Priority Applications (7)

Application Number	Priority Date	Filing Date	Title
US07/134,863 US5120860A (en)	1987-12-18	1987-12-18	Process for the production of aziridines
DE3851327T DE3851327T2 (de)	1987-12-18	1988-12-16	Verfahren zur herstellung von aminen, hydroxyaminen und aziridinen.
PCT/US1988/004456 WO1989005797A2 (fr)	1987-12-18	1988-12-16	Procede de production d'aziridines
PCT/US1988/004455 WO1989006229A1 (fr)	1987-12-18	1988-12-16	Procede de production d'amines, hydroxyamines et aziridines
EP89901980A EP0358736A1 (fr)	1987-12-18	1988-12-16	Procede de production d'aziridines
EP89901223A EP0346443B1 (fr)	1987-12-18	1988-12-16	Procede de production d'amines, hydroxyamines et aziridines
CA000586709A CA1336717C (fr)	1987-12-18	1988-12-21	Methode de preparation d'amines, d'hydroxylamines et d'aziridines

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US07/134,863 US5120860A (en)	1987-12-18	1987-12-18	Process for the production of aziridines
PCT/US1988/004455 WO1989006229A1 (fr)	1987-12-18	1988-12-16	Procede de production d'amines, hydroxyamines et aziridines
CA000586709A CA1336717C (fr)	1987-12-18	1988-12-21	Methode de preparation d'amines, d'hydroxylamines et d'aziridines

Publications (1)

Publication Number	Publication Date
CA1336717C true CA1336717C (fr)	1995-08-15

Family

ID=25672327

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000586709A Expired - Fee Related CA1336717C (fr)	1987-12-18	1988-12-21	Methode de preparation d'amines, d'hydroxylamines et d'aziridines

Country Status (1)

Country	Link
CA (1)	CA1336717C (fr)

1988
- 1988-12-21 CA CA000586709A patent/CA1336717C/fr not_active Expired - Fee Related

Legal Events

Date	Code	Title	Description
2004-08-16	MKLA	Lapsed

Publication	Publication Date	Title
EP0324082B1 (fr)	1992-08-12	Procédé de synthèse de tamis moléculaires non zéolitiques
AU597985B2 (en)	1990-06-14	Production of light olefins
CA1284510C (fr)	1991-05-28	Isomerisation du xylene
EP0346443B1 (fr)	1994-08-31	Procede de production d'amines, hydroxyamines et aziridines
EP0251167A2 (fr)	1988-01-07	Procédé pour la condensation de cétones
US4874896A (en)	1989-10-17	Process for the production of alkylamines
US4701562A (en)	1987-10-20	Process for the condensation of aldehydes
US4818739A (en)	1989-04-04	Hydrocracking catalysts and processes employing non-zeolitic molecular sieves
US4751340A (en)	1988-06-14	Selective production of para-aromatics
US4791083A (en)	1988-12-13	Catalytic cracking catalysts comprising non-zeolitic molecular sieves
US4859314A (en)	1989-08-22	Catalytic cracking catalysts and cracking process using non-zeolitic molecular sieves
US4973709A (en)	1990-11-27	Process for the production of amines, hydroxyamines and aziridines
US4777301A (en)	1988-10-11	Process for the condensation of carbonyl and aromatic compounds
US4873325A (en)	1989-10-10	Process for the production of amides
US4864068A (en)	1989-09-05	Oligomerization processes and catalysts
US4734538A (en)	1988-03-29	Process for the production of dienes
CA1336717C (fr)	1995-08-15	Methode de preparation d'amines, d'hydroxylamines et d'aziridines
US4826804A (en)	1989-05-02	Catalyst for oligomerization process
WO1989005810A1 (fr)	1989-06-29	Procedes de production d'amines
CA1329213C (fr)	1994-05-03	Procede pour la production d'aziridines
JPH02184509A (ja)	1990-07-19	モレキュラーシーブの製造方法
DE3851327T2 (de)	1995-02-09	Verfahren zur herstellung von aminen, hydroxyaminen und aziridinen.
JPH03127764A (ja)	1991-05-30	アミンの製法