CA2029428A1 - Preparation de piperazines melangees avec des alcools et des amines - Google Patents

Preparation de piperazines melangees avec des alcools et des amines

Info

Publication number: CA2029428A1
Authority: CA; Canada
Prior art keywords: piperazine; extended; amine; alcohol; integer
Prior art date: 1990-11-07
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.): Abandoned

Application number

CA 2029428

Other languages

English (en)

Inventor

George E. Hartwell

Robert G. Bowman

David C. Molzahn

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.)

Dow Chemical Co

Original Assignee

Dow Chemical Co

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.)

1990-11-07

Filing date

1990-11-07

Publication date

1992-05-08

1990-11-07 Application filed by Dow Chemical Co filed Critical Dow Chemical Co

1990-11-07 Priority to CA 2029428 priority Critical patent/CA2029428A1/fr

1992-05-08 Publication of CA2029428A1 publication Critical patent/CA2029428A1/fr

Status Abandoned legal-status Critical Current

Links

150000004885 piperazines Chemical class 0.000 title claims abstract description 30
238000002360 preparation method Methods 0.000 title description 7
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims abstract description 73
239000000376 reactant Substances 0.000 claims abstract description 52
150000001412 amines Chemical class 0.000 claims abstract description 41
239000003054 catalyst Substances 0.000 claims abstract description 38
229960005141 piperazine Drugs 0.000 claims abstract description 38
239000011964 heteropoly acid Substances 0.000 claims abstract description 21
229910052721 tungsten Inorganic materials 0.000 claims abstract description 18
239000010937 tungsten Substances 0.000 claims abstract description 18
IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 claims abstract description 17
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims abstract description 17
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims abstract description 12
125000004193 piperazinyl group Chemical group 0.000 claims abstract description 12
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims abstract description 11
238000004519 manufacturing process Methods 0.000 claims abstract description 5
BCTWNMTZAXVEJL-UHFFFAOYSA-N phosphane;tungsten;tetracontahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.P.[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].[W] BCTWNMTZAXVEJL-UHFFFAOYSA-N 0.000 claims abstract description 5
238000000034 method Methods 0.000 claims description 58
229910052739 hydrogen Inorganic materials 0.000 claims description 30
239000001257 hydrogen Substances 0.000 claims description 29
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 25
-1 hydroxy, amino Chemical group 0.000 claims description 21
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 10
125000004103 aminoalkyl group Chemical group 0.000 claims description 10
239000000203 mixture Substances 0.000 claims description 10
125000004429 atom Chemical group 0.000 claims description 9
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 9
125000005842 heteroatom Chemical group 0.000 claims description 7
229910052698 phosphorus Inorganic materials 0.000 claims description 6
239000007788 liquid Substances 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
150000001768 cations Chemical class 0.000 claims description 3
150000001875 compounds Chemical class 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
229910052710 silicon Inorganic materials 0.000 claims description 3
239000003377 acid catalyst Substances 0.000 abstract description 4
238000006243 chemical reaction Methods 0.000 description 25
239000000047 product Substances 0.000 description 24
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
150000002431 hydrogen Chemical group 0.000 description 13
238000005576 amination reaction Methods 0.000 description 11
239000002904 solvent Substances 0.000 description 9
239000000463 material Substances 0.000 description 8
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
239000002253 acid Substances 0.000 description 7
150000001298 alcohols Chemical class 0.000 description 7
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
229920000768 polyamine Polymers 0.000 description 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
125000003944 tolyl group Chemical group 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
KWWRWWPXBGFORG-UHFFFAOYSA-N 1-(1-piperazin-1-ylethyl)piperazine Chemical compound C1CNCCN1C(C)N1CCNCC1 KWWRWWPXBGFORG-UHFFFAOYSA-N 0.000 description 4
VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical class NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 4
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 4
150000001450 anions Chemical class 0.000 description 4
239000006227 byproduct Substances 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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 4
230000035484 reaction time Effects 0.000 description 4
PAOXFRSJRCGJLV-UHFFFAOYSA-N 2-[4-(2-aminoethyl)piperazin-1-yl]ethanamine Chemical compound NCCN1CCN(CCN)CC1 PAOXFRSJRCGJLV-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-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
LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 3
230000007423 decrease Effects 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000011574 phosphorus Substances 0.000 description 3
235000013772 propylene glycol Nutrition 0.000 description 3
238000000926 separation method Methods 0.000 description 3
WGCYRFWNGRMRJA-UHFFFAOYSA-N 1-ethylpiperazine Chemical class CCN1CCNCC1 WGCYRFWNGRMRJA-UHFFFAOYSA-N 0.000 description 2
VARKIGWTYBUWNT-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanol Chemical compound OCCN1CCN(CCO)CC1 VARKIGWTYBUWNT-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
239000004721 Polyphenylene oxide Substances 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
239000002998 adhesive polymer Substances 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
230000000507 anthelmentic effect Effects 0.000 description 2
238000001354 calcination Methods 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
238000009833 condensation Methods 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000002638 heterogeneous catalyst Substances 0.000 description 2
239000003317 industrial substance Substances 0.000 description 2
239000002917 insecticide Substances 0.000 description 2
239000010687 lubricating oil Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
229920000570 polyether Polymers 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
229920005862 polyol Polymers 0.000 description 2
150000003077 polyols Chemical class 0.000 description 2
150000003139 primary aliphatic amines Chemical class 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000243 solution Substances 0.000 description 2
241000894007 species Species 0.000 description 2
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
XDHVNMPVLPEHND-UHFFFAOYSA-N 1-(2-piperazin-1-ylethyl)piperazine Chemical compound C1CNCCN1CCN1CCNCC1 XDHVNMPVLPEHND-UHFFFAOYSA-N 0.000 description 1
RMKZICWNCLBCKP-UHFFFAOYSA-N 1-[1,1-di(piperazin-1-yl)ethyl]piperazine Chemical compound C1CNCCN1C(N1CCNCC1)(C)N1CCNCC1 RMKZICWNCLBCKP-UHFFFAOYSA-N 0.000 description 1
BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
HXMVNCMPQGPRLN-UHFFFAOYSA-N 2-hydroxyputrescine Chemical compound NCCC(O)CN HXMVNCMPQGPRLN-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
229910052684 Cerium Inorganic materials 0.000 description 1
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
229910052777 Praseodymium Inorganic materials 0.000 description 1
229910052776 Thorium Inorganic materials 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
229910052770 Uranium Inorganic materials 0.000 description 1
229910052768 actinide Inorganic materials 0.000 description 1
230000006978 adaptation Effects 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
125000005263 alkylenediamine group Chemical group 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical compound O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 description 1
150000001414 amino alcohols Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
229910052785 arsenic Inorganic materials 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
150000001923 cyclic compounds Chemical class 0.000 description 1
DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical compound CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000009826 distribution Methods 0.000 description 1
229940031098 ethanolamine Drugs 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
229910052733 gallium Inorganic materials 0.000 description 1
239000007789 gas Substances 0.000 description 1
229910052732 germanium Inorganic materials 0.000 description 1
239000011491 glass wool Substances 0.000 description 1
239000002815 homogeneous catalyst Substances 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
229910052747 lanthanoid Inorganic materials 0.000 description 1
238000002386 leaching Methods 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
150000001457 metallic cations Chemical class 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
WBIWIXJUBVWKLS-UHFFFAOYSA-N n'-(2-piperazin-1-ylethyl)ethane-1,2-diamine Chemical compound NCCNCCN1CCNCC1 WBIWIXJUBVWKLS-UHFFFAOYSA-N 0.000 description 1
DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229910052758 niobium Inorganic materials 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
IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
229920001281 polyalkylene Polymers 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
150000003141 primary amines Chemical group 0.000 description 1
AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
229910052761 rare earth metal Inorganic materials 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
150000005619 secondary aliphatic amines Chemical class 0.000 description 1
150000003335 secondary amines Chemical group 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
229910052715 tantalum Inorganic materials 0.000 description 1
CHYBTAZWINMGHA-UHFFFAOYSA-N tetraoctylazanium Chemical compound CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC CHYBTAZWINMGHA-UHFFFAOYSA-N 0.000 description 1
ZCUFMDLYAMJYST-UHFFFAOYSA-N thorium dioxide Chemical compound O=[Th]=O ZCUFMDLYAMJYST-UHFFFAOYSA-N 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
230000007704 transition Effects 0.000 description 1
150000004072 triols Chemical class 0.000 description 1
150000003657 tungsten Chemical class 0.000 description 1
229910001930 tungsten oxide Inorganic materials 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
239000008096 xylene Substances 0.000 description 1
239000010457 zeolite Substances 0.000 description 1
229910052726 zirconium Inorganic materials 0.000 description 1

Landscapes

Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA 2029428 1990-11-07 1990-11-07 Preparation de piperazines melangees avec des alcools et des amines Abandoned CA2029428A1 (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA 2029428 CA2029428A1 (fr)	1990-11-07	1990-11-07	Preparation de piperazines melangees avec des alcools et des amines

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA 2029428 CA2029428A1 (fr)	1990-11-07	1990-11-07	Preparation de piperazines melangees avec des alcools et des amines

Publications (1)

Publication Number	Publication Date
CA2029428A1 true CA2029428A1 (fr)	1992-05-08

Family

ID=4146355

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2029428 Abandoned CA2029428A1 (fr)	1990-11-07	1990-11-07	Preparation de piperazines melangees avec des alcools et des amines

Country Status (1)

Country	Link
CA (1)	CA2029428A1 (fr)

1990
- 1990-11-07 CA CA 2029428 patent/CA2029428A1/fr not_active Abandoned

Legal Events

Date	Code	Title	Description
1996-05-07	FZDE	Dead

Publication	Publication Date	Title
US4927931A (en)	1990-05-22	Preparation of alkyl-extended, alcohol-extended or amine-extended piperazines
EP0392007B1 (fr)	1993-12-15	Procede de preparation de polyalkylenepolyamines etendues lineairement
JP2587067B2 (ja)	1997-03-05	チタニア触媒、その製造方法及び線状ポリエチレンポリアミン類の製造におけるその使用
US4983735A (en)	1991-01-08	Preparation of alcohol-extended and amine-extended piperazines
EP0384766B1 (fr)	1994-07-06	Procédé de préparation de polyalkylènepolyamines étendues linéairement
US5073635A (en)	1991-12-17	Process of preparing linearly-extended polyalkylenepolyamines employing metal silicate catalysts
WO2010042159A1 (fr)	2010-04-15	Procédés de production de triamines n-amino fonctionnelles cycliques
US5256786A (en)	1993-10-26	Catalytic reforming of cyclic alkyleneamines
EP0416674B1 (fr)	1996-10-30	Procédé pour la préparation de polyalkylène polyamines
US4973569A (en)	1990-11-27	Preparation of group VB metal phosphate catalysts therefor
US5410087A (en)	1995-04-25	Catalytic reforming of alkyleneamines
US4996363A (en)	1991-02-26	Catalytic reforming of alkyleneamines to linearly-extended polyalkylenepolyamines
US5225600A (en)	1993-07-06	Amines catalysis using group VIB metal-containing condensation catalysts
EP0450709A1 (fr)	1991-10-09	Production sélective de la triéthylène-tétramine et de l'aminoéthyléthanolamine
CA2022775C (fr)	1997-03-04	Preparation d'amines en presence de catalyseurs de condensation contenant un metal du groupe vi-b
CA2029428A1 (fr)	1992-05-08	Preparation de piperazines melangees avec des alcools et des amines
EP0412613A2 (fr)	1991-02-13	Catalyse d'amines utilisant des catalyseurs de condensation de phosphates métalliques de structure cyclique
CA2022783C (fr)	1999-05-04	Organometalates vicinaux de di-(hetero) alkylene et procede de production d'amines
US5118850A (en)	1992-06-02	Catalytic reforming of alkyleneamines to linearly-extended polyalkylenepolyamines
US5118851A (en)	1992-06-02	Process of preparing mixtures of polyalkylenepolyamines and alkanolpolyamines
EP0449384A1 (fr)	1991-10-02	Production sélective de polyalkylène polyamines supérieurs et de polyalkyline polyamines contenant des groupements hydroxyles
US5210307A (en)	1993-05-11	Catalytic reforming of alkyleneamines to linearly-extended polyalkylenepolyamines
JPH04187681A (ja)	1992-07-06	アルコール連鎖延長及びアミン連鎖延長ピペラジンの調整方法
EP0449382A1 (fr)	1991-10-02	Production sélective de tétraéthylènepentamine linéaire et d'hydroxyéthyldiéthylènetriamine