JPS6041641A - 非環状ポリアルキレンポリアミンの製法 - Google Patents
非環状ポリアルキレンポリアミンの製法Info
- Publication number
- JPS6041641A JPS6041641A JP59147732A JP14773284A JPS6041641A JP S6041641 A JPS6041641 A JP S6041641A JP 59147732 A JP59147732 A JP 59147732A JP 14773284 A JP14773284 A JP 14773284A JP S6041641 A JPS6041641 A JP S6041641A
- Authority
- JP
- Japan
- Prior art keywords
- group
- catalyst
- ammonia
- primary
- amine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229920000768 polyamine Polymers 0.000 title claims description 98
- 238000004519 manufacturing process Methods 0.000 title claims description 35
- 229920001281 polyalkylene Polymers 0.000 title claims description 30
- 125000004122 cyclic group Chemical group 0.000 title description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 136
- 238000006243 chemical reaction Methods 0.000 claims description 81
- 239000003054 catalyst Substances 0.000 claims description 75
- 229910021529 ammonia Inorganic materials 0.000 claims description 68
- 229910019142 PO4 Inorganic materials 0.000 claims description 64
- 238000000034 method Methods 0.000 claims description 64
- 235000021317 phosphate Nutrition 0.000 claims description 64
- -1 alkylene amine compounds Chemical class 0.000 claims description 63
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 54
- 125000002015 acyclic group Chemical group 0.000 claims description 47
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 46
- 229910052751 metal Inorganic materials 0.000 claims description 45
- 239000002184 metal Substances 0.000 claims description 45
- 150000001875 compounds Chemical class 0.000 claims description 42
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 32
- 239000010452 phosphate Substances 0.000 claims description 29
- 230000002378 acidificating effect Effects 0.000 claims description 27
- 150000001412 amines Chemical class 0.000 claims description 26
- 150000002739 metals Chemical class 0.000 claims description 25
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 230000008569 process Effects 0.000 claims description 18
- LQFNMFDUAPEJRY-UHFFFAOYSA-K lanthanum(3+);phosphate Chemical compound [La+3].[O-]P([O-])([O-])=O LQFNMFDUAPEJRY-UHFFFAOYSA-K 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 150000003141 primary amines Chemical group 0.000 claims description 11
- 229910052746 lanthanum Inorganic materials 0.000 claims description 10
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 7
- 238000010924 continuous production Methods 0.000 claims description 7
- 229910052777 Praseodymium Inorganic materials 0.000 claims description 6
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 6
- 229910052779 Neodymium Inorganic materials 0.000 claims description 5
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 229910052727 yttrium Inorganic materials 0.000 claims description 5
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 4
- 238000004064 recycling Methods 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
- 229910052772 Samarium Inorganic materials 0.000 claims description 3
- 150000003973 alkyl amines Chemical group 0.000 claims description 3
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 claims description 3
- 229910052684 Cerium Inorganic materials 0.000 claims description 2
- 229910052692 Dysprosium Inorganic materials 0.000 claims description 2
- 229910052688 Gadolinium Inorganic materials 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 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 description 2
- 239000001177 diphosphate Substances 0.000 claims description 2
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical group [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims description 2
- 235000011180 diphosphates Nutrition 0.000 claims description 2
- KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 claims description 2
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 claims description 2
- 239000000178 monomer Substances 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims 4
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 3
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 claims 2
- 125000003916 ethylene diamine group Chemical group 0.000 claims 2
- 229910052747 lanthanoid Inorganic materials 0.000 claims 2
- 239000000945 filler Substances 0.000 claims 1
- ZSZNUIGFWQXJMQ-UHFFFAOYSA-K gold(3+);phosphate Chemical class [Au+3].[O-]P([O-])([O-])=O ZSZNUIGFWQXJMQ-UHFFFAOYSA-K 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 19
- 239000004698 Polyethylene Substances 0.000 description 16
- 229920000573 polyethylene Polymers 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 14
- 150000003335 secondary amines Chemical class 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 7
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 229920002873 Polyethylenimine Polymers 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical group [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000005576 amination reaction Methods 0.000 description 4
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000001030 gas--liquid chromatography Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000010454 slate Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 3
- 229910000388 diammonium phosphate Inorganic materials 0.000 description 3
- 235000019838 diammonium phosphate Nutrition 0.000 description 3
- FYDKNKUEBJQCCN-UHFFFAOYSA-N lanthanum(3+);trinitrate Chemical compound [La+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O FYDKNKUEBJQCCN-UHFFFAOYSA-N 0.000 description 3
- 229910001463 metal phosphate Inorganic materials 0.000 description 3
- KFIGICHILYTCJF-UHFFFAOYSA-N n'-methylethane-1,2-diamine Chemical compound CNCCN KFIGICHILYTCJF-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 150000002910 rare earth metals Chemical class 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 2
- 229910000387 ammonium dihydrogen phosphate Inorganic materials 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000039 congener Substances 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000002979 fabric softener Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 239000003879 lubricant additive Substances 0.000 description 2
- 229910001960 metal nitrate Inorganic materials 0.000 description 2
- 235000019837 monoammonium phosphate Nutrition 0.000 description 2
- DZNFWGVDYGAMJB-UHFFFAOYSA-K neodymium(3+);phosphate Chemical compound [Nd+3].[O-]P([O-])([O-])=O DZNFWGVDYGAMJB-UHFFFAOYSA-K 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- KDCUNMWWJBHRSC-UHFFFAOYSA-K praseodymium(3+);phosphate Chemical compound [Pr+3].[O-]P([O-])([O-])=O KDCUNMWWJBHRSC-UHFFFAOYSA-K 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- LSYBWANTZYUTGJ-UHFFFAOYSA-N 2-[2-(dimethylamino)ethyl-methylamino]ethanol Chemical compound CN(C)CCN(C)CCO LSYBWANTZYUTGJ-UHFFFAOYSA-N 0.000 description 1
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
- 241000208140 Acer Species 0.000 description 1
- 229910000521 B alloy Inorganic materials 0.000 description 1
- XOZCUVAGXFOUFU-UHFFFAOYSA-N C=C.NCCO Chemical compound C=C.NCCO XOZCUVAGXFOUFU-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241000510672 Cuminum Species 0.000 description 1
- 235000007129 Cuminum cyminum Nutrition 0.000 description 1
- 229910052691 Erbium Inorganic materials 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- BVHLGVCQOALMSV-JEDNCBNOSA-N L-lysine hydrochloride Chemical compound Cl.NCCCC[C@H](N)C(O)=O BVHLGVCQOALMSV-JEDNCBNOSA-N 0.000 description 1
- 229910052765 Lutetium Inorganic materials 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910052776 Thorium Inorganic materials 0.000 description 1
- 229910052775 Thulium Inorganic materials 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- 229910052768 actinide Inorganic materials 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000003190 augmentative effect Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical compound [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- 238000011905 homologation Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 description 1
- OHSVLFRHMCKCQY-UHFFFAOYSA-N lutetium atom Chemical compound [Lu] OHSVLFRHMCKCQY-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000004712 monophosphates Chemical class 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- KRDDBYPPQLOAPV-UHFFFAOYSA-N n'-[2-(dimethylamino)ethyl]-n'-methylethane-1,2-diamine Chemical compound CN(C)CCN(C)CCN KRDDBYPPQLOAPV-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/04—Nitrogen directly attached to aliphatic or cycloaliphatic carbon atoms
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/515,314 US4463193A (en) | 1983-07-19 | 1983-07-19 | Production of noncyclic polyalkylene polyamines |
| US515314 | 2000-02-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6041641A true JPS6041641A (ja) | 1985-03-05 |
| JPH0226620B2 JPH0226620B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1990-06-12 |
Family
ID=24050842
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59147732A Granted JPS6041641A (ja) | 1983-07-19 | 1984-07-18 | 非環状ポリアルキレンポリアミンの製法 |
Country Status (8)
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61130260A (ja) * | 1984-11-26 | 1986-06-18 | テキサコ・ケミカル・カンパニー | 気相反応によるポリアルキレンポリアミン類 |
| JPS61280455A (ja) * | 1985-04-04 | 1986-12-11 | ユニオン、カ−バイド、コ−ポレ−シヨン | 相互交換可能な処理方法 |
| JPS61289065A (ja) * | 1985-04-04 | 1986-12-19 | ユニオン、カ−バイド、コ−ポレ−シヨン | 酸素含有ポリアミンの転化 |
| JPS6322829A (ja) * | 1986-06-28 | 1988-01-30 | ヒュルス・アクチェンゲゼルシャフト | Ｃ↓１↓２アミノカルボン酸ラクタムからのプレポリマ−アミドの製造方法 |
| CN103848875A (zh) * | 2012-11-30 | 2014-06-11 | 哈尔滨誉衡药业股份有限公司 | 一种龙胆苦苷原料的制备方法 |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4582904A (en) * | 1982-05-24 | 1986-04-15 | Air Products And Chemicals, Inc. | Amine production via condensation reactions using rare earth metal hydrogen phosphates as catalysts |
| JPS6078945A (ja) * | 1983-10-06 | 1985-05-04 | Mitsui Toatsu Chem Inc | ジエチレントリアミンの製造法 |
| US4605770A (en) * | 1983-12-22 | 1986-08-12 | Air Products And Chemicals, Inc. | Noncyclic polyalkylene polyamines by the reaction of an alkanolamine compound and an alkyleneamine compound in the presence of a Group IIA or Group IIIB metal acid phosphate catalyst |
| CA1279871C (en) * | 1985-04-04 | 1991-02-05 | David J. Schreck | Use of pressure to control the non-cyclics/cyclics ratio of polyalkylene polyamines |
| US4827037A (en) * | 1985-04-04 | 1989-05-02 | Union Carbide Corporation | Quality of catalytically prepared polyalkylene polyamines |
| US4720588A (en) * | 1986-01-16 | 1988-01-19 | Air Products And Chemicals, Inc. | Polyalkylene polyamines via vapor phase reaction using inert gas |
| US4766247A (en) * | 1986-09-26 | 1988-08-23 | Air Products And Chemicals, Inc. | Color reduction of polyamines by mild catalytic hydrogenation |
| JP2764968B2 (ja) * | 1988-02-10 | 1998-06-11 | 東ソー株式会社 | アルキレンアミン類の製造法 |
| US5011999A (en) * | 1989-02-23 | 1991-04-30 | The Dow Chemical Company | Process of preparing non-cyclic polyalkylenepolyamines employing group VB metal catalysts |
| US4983736A (en) * | 1989-08-08 | 1991-01-08 | Union Carbide Chemicals And Plastic Company Inc. | Amines catalysis using metallic polyphosphate condensation catalysts having a condensed structure |
| US5202492A (en) * | 1989-08-08 | 1993-04-13 | Union Carbide Chemicals & Plastics Technology Corporation | Amines catalysis using metallic phosphate condensation catalysts having a cyclic structure |
| US5210306A (en) * | 1989-08-08 | 1993-05-11 | Union Carbide Chemicals & Plastics Technology Corporation | Promoted amines catalysis |
| US5225600A (en) * | 1989-08-08 | 1993-07-06 | Union Carbide Chemicals & Plastics Technology Corporation | Amines catalysis using group VIB metal-containing condensation catalysts |
| US5101074A (en) * | 1989-08-08 | 1992-03-31 | Union Carbide Chemicals & Plastics Technology Corporation | Vicinal di(hetro) alkylene organometalates and processes for the production of amines therewith |
| US5231229A (en) * | 1989-10-06 | 1993-07-27 | The Dow Chemical Company | Catalytic process for the production of ethyleneamines |
| US5225598A (en) * | 1990-03-30 | 1993-07-06 | Union Carbide Chemicals & Plastics Technology Corporation | Selective production of linear pentaethylenehexamine and hydroxyethyldiethylenetriamine |
| US5214215A (en) * | 1990-03-30 | 1993-05-25 | Union Carbide Chemicals & Plastics Technology Corporation | Selective production of aminoethylethanolamine |
| US5214213A (en) * | 1990-03-30 | 1993-05-25 | Union Carbide Chemicals & Plastics Technology Corporation | Selective production of linear tetraethylenepentamine and hydroxyethyldiethylenetriamine |
| 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 |
| US5166415A (en) * | 1990-03-30 | 1992-11-24 | Union Carbide Chemicals & Plastics Technology Corporation | Selective production of diethylenetriamine and aminoethylethanolamine |
| US5225599A (en) * | 1990-03-30 | 1993-07-06 | Union Carbide Chemicals & Plastics Technology Corporation | Selective production of linear triethylenetetramine and aminoethylethanolamine |
| US5073635A (en) * | 1990-06-22 | 1991-12-17 | The Dow Chemical Company | Process of preparing linearly-extended polyalkylenepolyamines employing metal silicate catalysts |
| DE19608555A1 (de) * | 1996-03-06 | 1997-09-11 | Basf Ag | Verwendung von Polymerisaten als Biozid |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6029587U (ja) * | 1983-08-05 | 1985-02-28 | 東 一雄 | 人体洗滌機 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2073671A (en) * | 1931-04-02 | 1937-03-16 | Rohm & Haas | Manufacture of amines |
| US2033866A (en) * | 1931-08-13 | 1936-03-10 | Unichem Chemikalien Handels A | Process for the production of aliphatic or cycloaliphatic primary amines |
| US2085785A (en) * | 1935-06-18 | 1937-07-06 | Girdler Corp | Production of alkylamines |
| US2529923A (en) * | 1943-04-22 | 1950-11-14 | Eastman Kodak Co | 2-(2-hydroxyethoxy) ethylamine |
| US3211667A (en) * | 1960-04-13 | 1965-10-12 | Continental Oil Co | Corrosion inhibition |
| US3152187A (en) * | 1960-04-13 | 1964-10-06 | Continental Oil Co | Condensation product of unsaturated diols and polyalkylene polyamines and method of preparation thereof |
| US3320318A (en) * | 1963-08-19 | 1967-05-16 | Continental Oil Co | Thiobenzene-diol-polyamine corrosion inhibiting composition |
| SE345122B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1966-12-30 | 1972-05-15 | Mo Och Domsjoe Ab | |
| US3714259A (en) * | 1970-08-20 | 1973-01-30 | Jefferson Chem Co Inc | Production of linear polyethylene polyamines |
| US3767709A (en) * | 1971-09-02 | 1973-10-23 | Union Oil Co | Alcohol amine interchange |
| US3755447A (en) * | 1971-11-26 | 1973-08-28 | Exxon Research Engineering Co | Polyalkylene polyamine separation and purification |
| 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 |
| US4316840A (en) * | 1980-11-25 | 1982-02-23 | Air Products And Chemicals, Inc. | Reforming linear polyamines |
| US4316841A (en) * | 1980-12-08 | 1982-02-23 | Air Products And Chemicals, Inc. | Reforming linear polyamines |
| US4362886A (en) * | 1981-01-05 | 1982-12-07 | Air Products And Chemicals, Inc. | Preparation of linear polyalkylene polyamines using metal catalyst |
| US4405784A (en) * | 1981-06-29 | 1983-09-20 | Air Products And Chemicals, Inc. | Method of making triethylenediamine |
| US4448997A (en) * | 1981-07-16 | 1984-05-15 | Texaco Inc. | Preparation of linear polyethylenepolyamines with an aluminum phosphate catalyst |
| US4394524A (en) * | 1981-08-31 | 1983-07-19 | Air Products And Chemicals, Inc. | Preparation of polyalkylene polyamines from ammonia, alkyleneamine, and alkanolamine |
-
1983
- 1983-07-19 US US06/515,314 patent/US4463193A/en not_active Expired - Lifetime
-
1984
- 1984-07-13 AR AR297206A patent/AR240449A1/es active
- 1984-07-16 CA CA000458979A patent/CA1221385A/en not_active Expired
- 1984-07-16 ZA ZA845469A patent/ZA845469B/xx unknown
- 1984-07-17 DE DE8484108425T patent/DE3461787D1/de not_active Expired
- 1984-07-17 EP EP84108425A patent/EP0131958B1/en not_active Expired
- 1984-07-18 JP JP59147732A patent/JPS6041641A/ja active Granted
- 1984-07-19 BR BR8403668A patent/BR8403668A/pt not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6029587U (ja) * | 1983-08-05 | 1985-02-28 | 東 一雄 | 人体洗滌機 |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61130260A (ja) * | 1984-11-26 | 1986-06-18 | テキサコ・ケミカル・カンパニー | 気相反応によるポリアルキレンポリアミン類 |
| JPS61280455A (ja) * | 1985-04-04 | 1986-12-11 | ユニオン、カ−バイド、コ−ポレ−シヨン | 相互交換可能な処理方法 |
| JPS61289065A (ja) * | 1985-04-04 | 1986-12-19 | ユニオン、カ−バイド、コ−ポレ−シヨン | 酸素含有ポリアミンの転化 |
| JPS6322829A (ja) * | 1986-06-28 | 1988-01-30 | ヒュルス・アクチェンゲゼルシャフト | Ｃ↓１↓２アミノカルボン酸ラクタムからのプレポリマ−アミドの製造方法 |
| CN103848875A (zh) * | 2012-11-30 | 2014-06-11 | 哈尔滨誉衡药业股份有限公司 | 一种龙胆苦苷原料的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0131958A1 (en) | 1985-01-23 |
| JPH0226620B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1990-06-12 |
| EP0131958B1 (en) | 1986-12-30 |
| US4463193A (en) | 1984-07-31 |
| BR8403668A (pt) | 1985-07-02 |
| ZA845469B (en) | 1986-03-26 |
| CA1221385A (en) | 1987-05-05 |
| DE3461787D1 (en) | 1987-02-05 |
| AR240449A1 (es) | 1990-04-30 |
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