JP4664589B2 - アミンの製法及びその製造時の触媒の使用 - Google Patents
アミンの製法及びその製造時の触媒の使用 Download PDFInfo
- Publication number
- JP4664589B2 JP4664589B2 JP2003421212A JP2003421212A JP4664589B2 JP 4664589 B2 JP4664589 B2 JP 4664589B2 JP 2003421212 A JP2003421212 A JP 2003421212A JP 2003421212 A JP2003421212 A JP 2003421212A JP 4664589 B2 JP4664589 B2 JP 4664589B2
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- JP
- Japan
- Prior art keywords
- catalyst
- hydrogen
- alkyl
- reaction
- 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.)
- Expired - Fee Related
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- 239000003054 catalyst Substances 0.000 title claims abstract description 86
- 150000001412 amines Chemical class 0.000 title claims abstract description 21
- 238000004519 manufacturing process Methods 0.000 title abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 47
- 239000001257 hydrogen Substances 0.000 claims abstract description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 37
- 238000000034 method Methods 0.000 claims abstract description 36
- 150000001299 aldehydes Chemical class 0.000 claims abstract description 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 31
- 150000002576 ketones Chemical class 0.000 claims abstract description 31
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims abstract description 26
- 230000008569 process Effects 0.000 claims abstract description 25
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims abstract description 23
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 22
- 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 claims abstract description 16
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 11
- 150000003335 secondary amines Chemical class 0.000 claims abstract description 11
- 150000003333 secondary alcohols Chemical class 0.000 claims abstract description 8
- 229910017464 nitrogen compound Inorganic materials 0.000 claims abstract description 6
- 150000002830 nitrogen compounds Chemical class 0.000 claims abstract description 6
- 125000000075 primary alcohol group Chemical group 0.000 claims abstract description 5
- -1 basic metal salt Chemical class 0.000 claims description 125
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 14
- 229910052751 metal Inorganic materials 0.000 claims description 14
- 239000002184 metal Substances 0.000 claims description 14
- 239000010949 copper Substances 0.000 claims description 13
- 229910052759 nickel Inorganic materials 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 12
- 229910052802 copper Inorganic materials 0.000 claims description 11
- 239000007789 gas Substances 0.000 claims description 10
- 150000003141 primary amines Chemical class 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000012071 phase Substances 0.000 claims description 8
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 239000007791 liquid phase Substances 0.000 claims description 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
- KPPVNWGJXFMGAM-UUILKARUSA-N (e)-2-methyl-1-(6-methyl-3,4-dihydro-2h-quinolin-1-yl)but-2-en-1-one Chemical compound CC1=CC=C2N(C(=O)C(/C)=C/C)CCCC2=C1 KPPVNWGJXFMGAM-UUILKARUSA-N 0.000 claims description 5
- 229910017052 cobalt Inorganic materials 0.000 claims description 5
- 239000010941 cobalt Substances 0.000 claims description 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 5
- 229910052726 zirconium Inorganic materials 0.000 claims description 5
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 230000000737 periodic effect Effects 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 230000001376 precipitating effect Effects 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- 229910044991 metal oxide Inorganic materials 0.000 claims description 2
- 150000004706 metal oxides Chemical class 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 229910052728 basic metal Inorganic materials 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 238000001556 precipitation Methods 0.000 abstract description 9
- 239000010987 cubic zirconia Substances 0.000 abstract description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 2
- 238000005576 amination reaction Methods 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 239000003795 chemical substances by application Substances 0.000 description 18
- 150000001298 alcohols Chemical class 0.000 description 15
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 7
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 230000009466 transformation Effects 0.000 description 7
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- 125000000468 ketone group Chemical group 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 230000001476 alcoholic effect Effects 0.000 description 4
- 125000002877 alkyl aryl group Chemical group 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 4
- 238000000975 co-precipitation Methods 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 150000003138 primary alcohols Chemical class 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- 239000012266 salt solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003172 aldehyde group Chemical group 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 125000003302 alkenyloxy group Chemical group 0.000 description 3
- 125000006524 alkoxy alkyl amino group Chemical group 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 150000001414 amino alcohols Chemical class 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000004663 dialkyl amino group Chemical group 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 229910001928 zirconium oxide Inorganic materials 0.000 description 3
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 2
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
- AUWDOZOUJWEPBA-UHFFFAOYSA-N 2-(4-methoxyphenyl)ethanol Chemical compound COC1=CC=C(CCO)C=C1 AUWDOZOUJWEPBA-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- FTZILAQGHINQQR-UHFFFAOYSA-N 2-Methylpentanal Chemical compound CCCC(C)C=O FTZILAQGHINQQR-UHFFFAOYSA-N 0.000 description 2
- RGICCULPCWNRAB-UHFFFAOYSA-N 2-[2-(2-hexoxyethoxy)ethoxy]ethanol Chemical compound CCCCCCOCCOCCOCCO RGICCULPCWNRAB-UHFFFAOYSA-N 0.000 description 2
- YSAANLSYLSUVHB-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]ethanol Chemical compound CN(C)CCOCCO YSAANLSYLSUVHB-UHFFFAOYSA-N 0.000 description 2
- XSAYZAUNJMRRIR-UHFFFAOYSA-N 2-acetylnaphthalene Chemical compound C1=CC=CC2=CC(C(=O)C)=CC=C21 XSAYZAUNJMRRIR-UHFFFAOYSA-N 0.000 description 2
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 description 2
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- GDWRKZLROIFUML-UHFFFAOYSA-N 4-phenylbutan-2-ol Chemical compound CC(O)CCC1=CC=CC=C1 GDWRKZLROIFUML-UHFFFAOYSA-N 0.000 description 2
- DUFCMRCMPHIFTR-UHFFFAOYSA-N 5-(dimethylsulfamoyl)-2-methylfuran-3-carboxylic acid Chemical compound CN(C)S(=O)(=O)C1=CC(C(O)=O)=C(C)O1 DUFCMRCMPHIFTR-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- SXVPOSFURRDKBO-UHFFFAOYSA-N Cyclododecanone Chemical compound O=C1CCCCCCCCCCC1 SXVPOSFURRDKBO-UHFFFAOYSA-N 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- AIJULSRZWUXGPQ-UHFFFAOYSA-N Methylglyoxal Chemical compound CC(=O)C=O AIJULSRZWUXGPQ-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 229920002367 Polyisobutene Polymers 0.000 description 2
- 229910052777 Praseodymium Inorganic materials 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 125000003158 alcohol group Chemical group 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 2
- 125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
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- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
- KTHXBEHDVMTNOH-UHFFFAOYSA-N cyclobutanol Chemical compound OC1CCC1 KTHXBEHDVMTNOH-UHFFFAOYSA-N 0.000 description 1
- SHQSVMDWKBRBGB-UHFFFAOYSA-N cyclobutanone Chemical compound O=C1CCC1 SHQSVMDWKBRBGB-UHFFFAOYSA-N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- CGZZMOTZOONQIA-UHFFFAOYSA-N cycloheptanone Chemical compound O=C1CCCCCC1 CGZZMOTZOONQIA-UHFFFAOYSA-N 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- OASCQHPNDMJKTK-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1.OC1CCCC1 OASCQHPNDMJKTK-UHFFFAOYSA-N 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
- 229940043276 diisopropanolamine Drugs 0.000 description 1
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000002816 fuel additive Substances 0.000 description 1
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 1
- 239000011521 glass 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
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 1
- WGBBUURBHXLGFM-UHFFFAOYSA-N hexan-2-amine Chemical compound CCCCC(C)N WGBBUURBHXLGFM-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 125000005181 hydroxyalkylaminoalkyl group Chemical group 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229940102253 isopropanolamine Drugs 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 229910000311 lanthanide oxide Inorganic materials 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 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
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 1
- ZUHZZVMEUAUWHY-UHFFFAOYSA-N n,n-dimethylpropan-1-amine Chemical compound CCCN(C)C ZUHZZVMEUAUWHY-UHFFFAOYSA-N 0.000 description 1
- OBYVIBDTOCAXSN-UHFFFAOYSA-N n-butan-2-ylbutan-2-amine Chemical compound CCC(C)NC(C)CC OBYVIBDTOCAXSN-UHFFFAOYSA-N 0.000 description 1
- XRKQMIFKHDXFNQ-UHFFFAOYSA-N n-cyclohexyl-n-ethylcyclohexanamine Chemical compound C1CCCCC1N(CC)C1CCCCC1 XRKQMIFKHDXFNQ-UHFFFAOYSA-N 0.000 description 1
- RIVIDPPYRINTTH-UHFFFAOYSA-N n-ethylpropan-2-amine Chemical compound CCNC(C)C RIVIDPPYRINTTH-UHFFFAOYSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- PZFYOFFTIYJCEW-UHFFFAOYSA-N n-tridecyltridecan-1-amine Chemical compound CCCCCCCCCCCCCNCCCCCCCCCCCCC PZFYOFFTIYJCEW-UHFFFAOYSA-N 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- 229910000484 niobium oxide Inorganic materials 0.000 description 1
- XNHGKSMNCCTMFO-UHFFFAOYSA-D niobium(5+);oxalate Chemical compound [Nb+5].[Nb+5].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O XNHGKSMNCCTMFO-UHFFFAOYSA-D 0.000 description 1
- URLJKFSTXLNXLG-UHFFFAOYSA-N niobium(5+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Nb+5].[Nb+5] URLJKFSTXLNXLG-UHFFFAOYSA-N 0.000 description 1
- 231100000989 no adverse effect Toxicity 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
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- CXLGNJCMPWUZKM-UHFFFAOYSA-N oxane-4-carbaldehyde Chemical compound O=CC1CCOCC1 CXLGNJCMPWUZKM-UHFFFAOYSA-N 0.000 description 1
- SIWVEOZUMHYXCS-UHFFFAOYSA-N oxo(oxoyttriooxy)yttrium Chemical compound O=[Y]O[Y]=O SIWVEOZUMHYXCS-UHFFFAOYSA-N 0.000 description 1
- GSUBXIVOZXWGKF-UHFFFAOYSA-N oxolane-3-carbaldehyde Chemical compound O=CC1CCOC1 GSUBXIVOZXWGKF-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- DYIZHKNUQPHNJY-UHFFFAOYSA-N oxorhenium Chemical compound [Re]=O DYIZHKNUQPHNJY-UHFFFAOYSA-N 0.000 description 1
- 150000002927 oxygen compounds Chemical class 0.000 description 1
- GGROONUBGIWGGS-UHFFFAOYSA-N oxygen(2-);zirconium(4+);hydrate Chemical compound O.[O-2].[O-2].[Zr+4] GGROONUBGIWGGS-UHFFFAOYSA-N 0.000 description 1
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 1
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- IGEIPFLJVCPEKU-UHFFFAOYSA-N pentan-2-amine Chemical compound CCCC(C)N IGEIPFLJVCPEKU-UHFFFAOYSA-N 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- 239000000088 plastic resin Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001521 polyalkylene glycol ether Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000006308 propyl amino group Chemical group 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910003449 rhenium oxide Inorganic materials 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- HYXGAEYDKFCVMU-UHFFFAOYSA-N scandium oxide Chemical compound O=[Sc]O[Sc]=O HYXGAEYDKFCVMU-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 125000003198 secondary alcohol group Chemical group 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
- C07C209/16—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- B01J21/066—Zirconium or hafnium; Oxides or hydroxides thereof
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/002—Mixed oxides other than spinels, e.g. perovskite
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/74—Iron group metals
- B01J23/755—Nickel
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
- B01J37/0063—Granulating
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/16—Reducing
- B01J37/18—Reducing with gases containing free hydrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/24—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
- C07C209/26—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds by reduction with hydrogen
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Description
CuOとして計算される銅の酸素含有化合物1〜30質量%、特に有利に2〜25質量%及び
NiOとして計算されるニッケルの酸素含有化合物14〜70質量%、有利に15〜50質量%、特に有利に21〜45質量%を含有し、この際、ニッケル対銅のモル比は、1より大きく、殊に1.2より大きく、特に1.8〜8.5であるのが有利である。
CoOとして計算されるコバルトの酸素含有化合物15〜50質量%、特に有利に21〜45質量%を含有する。
R1、R2は、水素(H)、アルキル、例えばC1〜C20−アルキル、シクロアルキル、例えばC3〜C12−シクロアルキル、アルコキシアルキル、例えばC2〜C30−アルコキシアルキル、ジアルキルアミノアルキル、例えばC3〜C30−ジアルキルアミノアルキル、アリール、アラルキル、例えばC7〜C20−アラルキル及びアルキルアリール、例えばC7〜C20−アルキルアリール、又は一緒になって−(CH2)j−X−(CH2)k−を表し、
R3、R4は、水素(H)、アルキル、例えばC1〜C200−アルキル、シクロアルキル、例えばC3〜C12−シクロアルキル、ヒドロキシアルキル、例えばC1〜C20−ヒドロキシアルキル、アミノアルキル、例えばC1〜C20−アミノアルキル、ヒドロキシアルキルアミノアルキル、例えばC2〜C20−ヒドロキシアルキルアミノアルキル、アルコキシアルキル、例えばC2〜C30−アルコキシアルキル、ジアルキルアミノアルキル、例えばC3〜C30−ジアルキルアミノアルキル、アルキルアミノアルキル、例えばC2〜C30−アルキルアミノアルキル、R5−(OCR6R7CR8R9)n−(OCR6R7)、アリール、ヘテロアリール、アラルキル、例えばC7〜C20−アラルキル、ヘテロアリールアルキル、例えばC4〜C20−ヘテロアリールアルキル、アルキルアリール、例えばC7〜C20−アルキルアリール、アルキルヘテロアリール、例えばC4〜C20−アルキルヘテロアリール及びY−(CH2)m−NR5−(CH2)q、又は一緒になって−(CH2)l−X−(CH2)m−を表すか、又は
R2とR4は、一緒になって−(CH2)l−X−(CH2)m−を表し、
R5、R10は、水素(H)、アルキル、例えばC1〜C4−アルキル、アルキルフェニル、例えばC7〜C40−アルキルフェニルを表し、
R6、R7、R8、R9は、水素(H)、メチル又はエチルを表し、
Xは、CH2、CHR5、酸素(O)、硫黄(S)又はNR5を表し、
Yは、N(R10)2、ヒドロキシ、C2〜C20−アルキルアミノアルキル又はC3〜C20−ジアルキルアミノアルキルを表し、
nは、1〜30の整数であり、j、k、l、m、qは、1〜4の整数である]のアミンは経済的に特に重要である。
Zは、CH2、CHR5、酸素(O)、NR5又はNCH2CH2OHを表し、
R1、R6、R7は前記のものを表す]の環状アミンの製造時にも使用され、この製造は、式V:
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12:
− 水素(H)、
R3、R4:
− アルキル、例えばC1〜C200−アルキル、有利にC1〜C14−アルキル、例えばメチル、エチル、n−プロピル、イソ−プロピル、n−ブチル、イソ−ブチル、s−ブチル、t−ブチル、n−ペンチル、イソ−ペンチル、s−ペンチル、ネオ−ペンチル、1,2−ジメチルプロピル、n−ヘキシル、イソ−ヘキシル、s−ヘキシル、シクロペンチルメチル、n−ヘプチル、イソ−ヘプチル、シクロヘキシルメチル、n−オクチル、イソ−オクチル、2−エチルヘキシル、n−デシル、2−n−プロピル−n−ヘプチル、n−トリデシル、2−n−ブチル−n−ノニル及び3−n−ブチル−n−ノニル、特に有利にイソ−プロピル、2−エチルヘキシル、n−デシル、2−n−プロピル−n−ヘプチル、n−トリデシル、2−ブチル−n−ノニル及び3−n−ブチル−n−ノニル並びに有利にC40〜C200−アルキル、例えばポリブチル、ポリイソブチル、ポリプロピル、ポリイソプロピル及びポリエチル、特に有利にポリブチル及びポリイソブチル、
− ヒドロキシアルキル、例えばC1〜C20−ヒドロキシアルキル、有利にC1〜C8−ヒドロキシアルキル、特に有利にC1〜C4−ヒドロキシアルキル、例えばヒドロキシメチル、1−ヒドロキシエチル、2−ヒドロキシエチル、1−ヒドロキシ−n−プロピル、2−ヒドロキシ−n−プロピル、3−ヒドロキシ−n−プロピル及び1−(ヒドロキシメチル)エチル、
− アミノアルキル、例えばC1〜C20−アミノアルキル、有利にC1〜C8−アミノアルキル、例えばアミノメチル、2−アミノエチル、2−アミノ−1,1−ジメチルエチル、2−アミノ−n−プロピル、3−アミノ−n−プロピル、4−アミノ−n−ブチル、5−アミノ−n−ペンチル、N−(2−アミノエチル)−2−アミノエチル及びN−(2−アミノエチル)アミノメチル、
− ヒドロキシアルキルアミノアルキル、例えばC2〜C20−ヒドロキシアルキルアミノアルキル、有利にC3〜C8−ヒドロキシアルキルアミノアルキル、例えば(2−ヒドロキシエチルアミノ)メチル、2−(2−ヒドロキシエチルアミノ)エチル及び3−(2−ヒドロキシエチルアミノ)プロピル、
− R5−(OCR6R7CR8R9)n−(OCR6R7)、有利に
R5−(OCHR7CHR9)n−(OCR6R7)、特に有利に
R5−(OCH2CHR9)n−(OCR6R7)、
− アルキルアミノアルキル、例えばC2〜C30−アルキルアミノアルキル、有利にC2〜C20−アルキルアミノアルキル、特に有利にC2〜C8−アルキルアミノアルキル、例えばメチルアミノメチル、2−メチルアミノエチル、エチルアミノメチル、2−エチルアミノエチル及び2−(イソ−プロピルアミノ)エチル、(R5)HN−(CH2)q、
− Y−(CH2)m−NR5−(CH2)q、
− ヘテロアリールアルキル、例えばC4〜C20−ヘテロアリールアルキル、例えばピリジ−2−イル−メチル、フラン−2−イル−メチル、ピロール−3−イル−メチル及びイミダゾール−2−イル−メチル、
− アルキルヘテロアリール、例えばC4〜C20−アルキルヘテロアリール、例えば2−メチル−3−ピリジニル、4,5−ジメチル−イミダゾール−2−イル、3−メチル−2−フラニル及び5−メチル−2−ピラジニル、
− ヘテロアリール、例えば2−ピリジニル、3−ピリジニル、4−ピリジニル、ピラジニル、ピロール−3−イル、イミダゾール−2−イル、2−フラニル及び3−フラニル、
R1、R2、R3、R4:
− シクロアルキル、例えばC3〜C12−シクロアルキル、有利にC3〜C8−シクロアルキル、例えばシクロプロピル、シクロブチル、シクロペンチル、シクロヘキシル、シクロヘプチル及びシクロオクチル、特に有利にシクロペンチル及びシクロヘキシル、
− アルコキシアルキル、例えばC2〜C30−アルコキシアルキル、有利にC2〜C20−アルコキシアルキル、特に有利にC2〜C8−アルコキシアルキル、例えばメトキシメチル、エトキシメチル、n−プロポキシメチル、イソ−プロポキシメチル、n−ブトキシメチル、イソ−ブトキシメチル、s−ブトキシメチル、t−ブトキシメチル、1−メトキシ−エチル及び2−メトキシエチル、特に有利にC2〜C4−アルコキシアルキル、
− ジアルキルアミノアルキル、例えばC3〜C30−ジアルキルアミノアルキル、有利にC3〜C20−ジアルキルアミノアルキル、特に有利にC3〜C10−ジアルキルアミノアルキル、例えばN,N−ジメチルアミノメチル、(N,N−ジブチルアミノ)メチル、2−(N,N−ジメチルアミノ)エチル、2−(N,N−ジエチルアミノ)エチル、2−(N,N−ジブチルアミノ)エチル、2−(N,N−ジ−n−プロピルアミノ)エチル及び2−(N,N−ジ−イソ−プロピルアミノ)エチル、3−(N,N−ジメチルアミノ)プロピル、(R5)2N−(CH2)q、
− アリール、例えばフェニル、1−ナフチル、2−ナフチル、1−アンスリル、2−アンスリル及び9−アンスリル、有利にフェニル、1−ナフチル及び2−ナフチル、特に有利にフェニル、
− アルキルアリール、例えばC7〜C20−アルキルアリール、有利にC7〜C12−アルキルフェニル、例えば2−メチルフェニル、3−メチルフェニル、4−メチルフェニル、2,4−ジメチルフェニル、2,5−ジメチルフェニル、2,6−ジメチルフェニル、3,4−ジメチルフェニル、3,5−ジメチルフェニル、2,3,4−トリメチルフェニル、2,3,5−トリメチルフェニル、2,3,6−トリメチルフェニル、2,4,6−トリメチルフェニル、2−エチルフェニル、3−エチルフェニル、4−エチルフェニル、2−n−プロピルフェニル、3−n−プロピルフェニル及び4−n−プロピルフェニル、
− アラルキル、例えばC7〜C20−アラルキル、有利にC7〜C12−フェニルアルキル、例えばベンジル、p−メトキシベンジル、3,4−ジメトキシベンジル、1−フェネチル、2−フェネチル、1−フェニルプロピル、2−フェニルプロピル、3−フェニル−プロピル、1−フェニル−ブチル、2−フェニル−ブチル、3−フェニル−ブチル及び4−フェニル−ブチル、特に有利にベンジル、1−フェネチル及び2−フェネチル、
− アルキル、例えばC1〜C20−アルキル、有利にC1〜C8−アルキル、例えばメチル、エチル、n−プロピル、イソ−プロピル、n−ブチル、イソ−ブチル、s−ブチル、t−ブチル、n−ペンチル、イソ−ペンチル、s−ペンチル、ネオ−ペンチル、1,2−ジメチルプロピル、n−ヘキシル、イソ−ヘキシル、s−ヘキシル、n−ヘプチル、イソ−ヘプチル、n−オクチル、イソ−オクチル、2−エチルヘキシル、特に有利にC1〜C4−アルキル、又は
− アルキル、有利にC1〜C4−アルキル、例えばメチル、エチル、n−プロピル、イソ−プロピル、n−ブチル、イソ−ブチル、s−ブチル及びt−ブチル、有利にメチル及びエチル、特に有利にメチル、
− アルキルフェニル、有利にC7〜C40−アルキルフェニル、例えば2−メチルフェニル、3−メチルフェニル、4−メチルフェニル、2,4−ジメチルフェニル、2,5−ジメチルフェニル、2,6−ジメチルフェニル、3,4−ジメチルフェニル、3,5−ジメチルフェニル、2−、3−、4−ノニルフェニル、2−、3−、4−デシルフェニル、2,3−、2,4−、2,5−、3,4−、3,5−ジノニルフェニル、2,3−、2,4−、2,5−、3,4−及び3,5−ジデシルフェニル、
R6、R7、R8、R9:
− メチル又はエチル、有利にメチル、
R11、R12:
− アルキル、例えばC1〜C20−アルキル、シクロアルキル、例えばC3〜C12−シクロアルキル、アリール、ヘテロアリール、アラルキル、例えばC7〜C20−アラルキル及びアルキルアリール、例えばC7〜C20−アルキルアリール(それぞれ前記のように定義されている)、
X:
− CH2、CHR5、酸素(O)、硫黄(S)又はNR5、有利にCH2及びO、
Y:
− N(R10)2、有利にNH2及びN(CH3)2、
− ヒドロキシ(OH)、
− C2〜C20−アルキルアミノアルキル、有利にC2〜C16−アルキルアミノアルキル、例えばメチルアミノメチル、2−メチルアミノエチル、エチルアミノメチル、2−エチルアミノエチル及び2−(イソ−プロピルアミノ)エチル、
− C3〜C20−ジアルキルアミノアルキル、有利にC3〜C16−ジアルキルアミノアルキル、例えばジメチルアミノメチル、2−ジメチルアミノエチル、2−ジエチルアミノエチル、2−(ジ−n−プロピルアミノ)エチル及び2−(ジ−イソ−プロピルアミノ)エチル、
Z:
− CH2、CHR5、O、NR5又はNCH2CH2OH、
j、l:
− 1〜4の整数(1、2、3又は4)、有利に2及び3、特に有利に2、
k、m、q:
− 1〜4の整数(1、2、3又は4)、有利に2、3及び4、特に有利に2及び3、
n:
− 1〜30の整数、有利に1〜8の整数(1、2、3、4、5、6、7又は8)、特に有利に1〜6の整数。
メタノール、エタノール、n−プロパノール、イソプロパノール、n−ブタノール、イソ−ブタノール、t−ブタノール、n−ペンタノール、n−ヘキサノール、2−エチルヘキサノール、トリデカノール、ステアリルアルコール、パルミチルアルコール、シクロブタノール、シクロペンタノール、シクロヘキサノール、ベンジルアルコール、2−フェニル−エタノール、2−(p−メトキシフェニル)エタノール、2−(3,4−ジメトキシフェニル)エタノール、1−フェニル−3−ブタノール、エタノールアミン、n−プロパノールアミン、イソプロパノールアミン、2−アミノ−1−プロパノール、1−メトキシ−2−プロパノール、3−アミノ−2,2−ジメチル−1−プロパノール、n−ペンタノールアミン(1−アミノ−5−ペンタノール)、n−ヘキサノールアミン(1−アミノ−6−ヘキサノール)、エタノールアミン、ジエタノールアミン、トリエタノールアミン、N−アルキルジエタノールアミン、ジイソプロパノールアミン、3−(2−ヒドロキシエチルアミノ)プロパン−1−オール、2−(N,N−ジメチルアミノ)エタノール、2−(N,N−ジエチルアミノ)エタノール、2−(N,N−ジ−n−プロピルアミノ)エタノール、2−(N,N−ジ−イソ−プロピルアミノ)エタノール、2−(N,N−ジ−n−ブチルアミノ)エタノール、2−(N,N−ジ−イソ−ブチルアミノ)エタノール、2−(N,N−ジ−s−ブチルアミノ)エタノール、2−(N,N−ジ−t−ブチルアミノ)エタノール、3−(N,N−ジメチルアミノ)プロパノール、3−(N,N−ジエチルアミノ)プロパノール、3−(N,N−ジ−n−プロピルアミノ)プロパノール、3−(N,N−ジ−イソ−プロピルアミノ)プロパノール、3−(N,N−ジ−n−ブチルアミノ)プロパノール、3−(N,N−ジ−イソ−ブチルアミノ)プロパノール、3−(N,N−ジ−s−ブチルアミノ)プロパノール、3−(N,N−ジ−t−ブチルアミノ)プロパノール、1−ジメチルアミノ−ペンタノール−4、1−ジエチルアミノ−ペンタノール−4、エチレングリコール、1,2−プロピレングリコール、1,3−プロピレングリコール、ジグリコール、1,4−ブタンジオール、1,5−ペンタンジオール、1,6−ヘキサンジオール、2,2−ビス[4−ヒシクロヘキシル]プロパン、メトキシエタノール、プロポキシエタノール、ブトキシエタノール、ポリイソブチルアルコール、ポリプロピルアルコール、ポリエチレングリコールエーテル、ポリプロピレングリコールエーテル及びポリブチレングリコールエーテル。最後に記載のポリアルキレングリコールエーテルは、本発明の反応の際に、その遊離のヒドロキシル基の変換により相応するアミンに変換される。
アセトン、エチルメチルケトン、メチルビニルケトン、イソブチルメチルケトン、3−メチルブタン−2−オン、ジエチルケトン、テトラロン、アセトフェノン、p−メチル−アセトフェノン、p−メトキシ−アセトフェノン、m−メトキシ−アセトフェノン、1−アセチル−ナフタリン、2−アセチル−ナフタリン、1−フェニル−3−ブタノン、シクロブタノン、シクロペンタノン、シクロペンテノン、シクロヘキサノン、シクロヘキセノン、2,6−ジメチルシクロヘキサノン、シクロヘプタノン、シクロドデカノン、アセチルアセトン、メチルグリオキサール及びベンゾフェノン。
ホルムアルデヒド、アセトアルデヒド、プロピオンアルデヒド、n−ブチルアルデヒド、イソブチルアルデヒド、ピバリンアルデヒド、n−ペンタナール、n−ヘキサナール、2−エチルヘキサナール、2−メチルペンタナール、3−メチルペンタナール、4−メチルペンタナール、グリオキサール、ベンズアルデヒド、p−メトキシベンズアルデヒド、p−メチルベンズアルデヒド、フェニルアセトアルデヒド、(p−メトキシ−フェニル)アセトアルデヒド、(3,4−ジメトキシフェニル)アセトアルデヒド、4−ホルミルテトラヒドロピラン、3−ホルミルテトラヒドロフラン、5−ホルミルバレロニトリル、シトロネラール、アクロレイン、メタクロレイン、エチルアクロレイン、シトラール、クロトンアルデヒド、3−メトキシプロピオンアルデヒド、3−アミノプロピオンアルデヒド、ヒドロキシピバリンアルデヒド、ジメチロールプロピオンアルデヒド、ジメチロールブチルアルデヒド、フルフラール、グリオキサール、グルタルアルデヒド並びにヒドロホルミル化されたオリゴマー及びポリマー、例えばヒドロホルミル化されたポリイソブテン(ポリイソブテンアルデヒド)又は1−ペンテン及びシクロペンテンのメタセシスにより得られ、かつヒドロホルミル化されたオリゴマー。
触媒A(本発明による):
次の記載のように、沈降容器中に予め装入された単斜晶二酸化ジルコニウム上への成分Cu、Co、Niの沈殿により、触媒Aを製造した:
ガラス製の攪拌容器中に、水2リットル中の単斜晶二酸化ジルコニウム−粉末(BET=105m2g−1)155gからの懸濁液を予め装入し、攪拌下に70℃まで加熱した。次いで、30分かかって、水2.8リットル中のCu(NO3)2×2.5H2O190.1g、Ni(NO3)2×6H2O561.9g及びCo(NO3)2×6H2O543.7gからの溶液を滴加した。20%炭酸ナトリウム溶液(水2.8リットル中のNa2CO3700g)の同時滴加により、pHを一定の6.0に保持した。この溶液の添加の後に、70℃で1時間後攪拌し、最後に炭酸ナトリウム溶液の添加によりpH値を7.4まで高めた。この懸濁液を吸引濾過器上にポンプ導入し、水100リットルで洗浄した。濾過ケーキを乾燥箱中、200℃で16時間乾燥させ、引き続き、粒径<1.6mmまで粉砕し、回転管炉内、400℃で、空気流(150リットル/h)中で2時間か焼した。
Ni (NiOとして計算) 28質量%
Co (CoOとして計算) 28質量%
Cu (CuOとして計算) 11質量%及び
Zr (ZrO2として計算) 33質量% 。
本発明の触媒Aと同様であるが、単斜晶二酸化ジルコニウムを装入しないことで異なる方法で、比較触媒を製造した。その代わりに、Cu−、Co−及びNi−硝酸塩を含有する金属塩溶液に、計算ZrO2(酢酸ジルコニウム溶液の質量に対して)20質量%を含有する酢酸ジルコニウム溶液775gを加えた(共沈)。その他の製法は触媒Aと同様に行った。同様にして得られたこの触媒粉末は、触媒Aの場合に記載されていると同じ組成を有した。
反応式:
触媒20gを攪拌オートクレーブ中のワイヤバスケット中に入れた。これに、PIBA/Mihagol(50/50)溶液150mlを加えて、この触媒床を液体で充分被覆した。このオートクレーブを閉じ、窒素でフラッシングし、700U/minで攪拌機を作動させ、H250バールを圧入し、200℃まで加熱した。次いで、この圧力をH2の付加的圧入により200バールまで調節した。この条件下に触媒を種々の時間で処理した。引き続き、冷却し、注意深く放圧し、かつ触媒の安定性を、横方向圧縮強度(SDF)(Seitendruckfestigkeit)の測定により測定した。
共沈により製造された触媒Bでは、行われた煮沸試験後のX−線回折図は、当初のX−線非晶質のZrO2−相が正方晶及び単斜晶のZrO2に変換したことを示していた。触媒Aでは、再結晶(=変態の変化)は確認されなかった。
Claims (8)
- 触媒の存在下に、1級又は2級アルコール、アルデヒド又はケトンと水素及びアンモニア、1級及び2級アミンの群から選択された窒素化合物との反応によりアミンを製造する方法において、その製造時に単斜晶又は正方晶の二酸化ジルコニウム上への触媒活性成分の沈殿を行って製造した触媒を使用し、その際、水素での処理の前の触媒の触媒活性組成物は、
ジルコニウムの酸素含有化合物(ZrO2として計算) 20〜65質量%
銅の酸素含有化合物(CuOとして計算) 1〜30質量%
ニッケルの酸素含有化合物(NiOとして計算) 15〜50質量%及び
コバルトの酸素含有化合物(CoOとして計算) 15〜50質量%
を含有していることを特徴とする、アミンの製造法。 - 沈殿された触媒活性成分は、水中に難溶性又は不溶性の塩基性金属塩であることを特徴とする、請求項1に記載の方法。
- 金属塩は、酸化物、水化酸化物、水酸化物、炭酸塩及び/又は炭酸水素塩であることを特徴とする、請求項1又は2に記載の方法。
- ニッケル対銅のモル比は1より大きいことを特徴とする、請求項1に記載の方法。
- 単斜晶又は正方晶の二酸化ジルコニウムは、周期表の副族IIIB又は主族IIAの金属酸化物1種以上を含有していることを特徴とする、請求項1から4までのいずれか1項に記載の方法。
- 反応を、80〜300℃の温度で実施することを特徴とする、請求項1から5までのいずれか1項に記載の方法。
- 反応を、液相で5〜30MPaの圧力で、又は気相で0.1〜40MPaの圧力で実施することを特徴とする、請求項1から6までのいずれか1項に記載の方法。
- 式I:
R1、R2は、水素(H)、C1〜C20−アルキル、C3〜C12−シクロアルキル、C2〜C30−アルコキシアルキル、C3〜C30−ジアルキルアミノアルキル、アリール、C7〜C20−アラルキル、C7〜C20−アルキルアリール、又は一緒になって−(CH2)j−X−(CH2)k−を表し、
R3、R4は、水素(H)、C1〜C200−アルキル、C3〜C12−シクロアルキル、C1〜C20−ヒドロキシアルキル、C1〜C20−アミノアルキル、C2〜C20−ヒドロキシアルキルアミノアルキル、C2〜C30−アルコキシアルキル、C3〜C30−ジアルキルアミノアルキル、C2〜C30−アルキルアミノアルキル、R5−(OCR6R7CR8R9)n−(OCR6R7)、アリール、ヘテロアリール、C7〜C20−アラルキル、C4〜C20−ヘテロアリールアルキル、C7〜C20−アルキルアリール、C4〜C20−アルキルヘテロアリール及びY−(CH2)m−NR5−(CH2)q、又は一緒になって−(CH2)l−X−(CH2)m−を表すか又は
R2とR4は、一緒になって−(CH2)l−X−(CH2)m−を表し、
R5、R10は、水素(H)、C1〜C4−アルキル、C7〜C40−アルキルフェニルを表し、
R6、R7、R8、R9は、水素(H)、メチル又はエチルを表し、
Xは、CH2、CHR5、酸素(O)、硫黄(S)又はNR5を表し、
Yは、N(R10)2、ヒドロキシ、C2〜C20−アルキルアミノアルキル又はC3〜C20−ジアルキルアミノアルキルを表し、
nは、1〜30の整数であり、j、k、l、m、qは、1〜4の整数である]のアミンを製造するために、式II:
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102005012209A1 (de) * | 2005-03-15 | 2006-09-28 | Basf Ag | Verfahren zur Herstellung eines Ethylamins |
DE102005029093A1 (de) * | 2005-06-23 | 2007-01-18 | Basf Ag | Verfahren zur kontinuierlichen Herstellung eines Amins |
JP4989888B2 (ja) * | 2005-12-28 | 2012-08-01 | 花王株式会社 | 含窒素化合物の製造方法 |
JP4989889B2 (ja) * | 2005-12-28 | 2012-08-01 | 花王株式会社 | 含窒素化合物の製造方法 |
WO2007077903A2 (en) | 2005-12-28 | 2007-07-12 | Kao Corporation | Process for producing nitrogen-containing compounds |
JP5038700B2 (ja) * | 2005-12-28 | 2012-10-03 | 花王株式会社 | 脂含窒素化合物の製造方法 |
ES2388682T3 (es) | 2006-05-31 | 2012-10-17 | Basf Se | Método para la producción de una amina |
RU2009104738A (ru) | 2006-07-14 | 2010-08-27 | Басф Се (De) | Способ получения амина |
JP2010504907A (ja) * | 2006-07-14 | 2010-02-18 | ビーエーエスエフ ソシエタス・ヨーロピア | アミンの製造方法 |
WO2008006752A1 (de) | 2006-07-14 | 2008-01-17 | Basf Se | Verfahren zur herstellung eines amins |
CN101489673A (zh) * | 2006-07-14 | 2009-07-22 | 巴斯夫欧洲公司 | 生产胺的方法 |
RU2009104740A (ru) | 2006-07-14 | 2010-08-27 | Басф Се (De) | Способ получения амина |
EP2043576B1 (en) * | 2006-07-20 | 2012-10-03 | SCA Hygiene Products AB | An apparatus and method for forming air-laid absorbent cores |
CN101903095B (zh) | 2007-12-21 | 2013-07-10 | 巴斯夫欧洲公司 | 制备胺的方法 |
US8293945B2 (en) | 2007-12-21 | 2012-10-23 | Basf Se | Method for producing an amine |
EP2234717A1 (de) | 2007-12-21 | 2010-10-06 | Basf Se | Verfahren zur herstellung eines amins |
CN101903094B (zh) | 2007-12-21 | 2013-03-20 | 巴斯夫欧洲公司 | 生产胺的方法 |
CN101910107B (zh) * | 2008-01-03 | 2013-03-13 | 阿克佐诺贝尔股份有限公司 | 制备亚乙基胺的方法 |
SG181100A1 (en) | 2009-12-03 | 2012-07-30 | Basf Se | Catalyst and method for producing an amine |
WO2011067200A1 (de) | 2009-12-03 | 2011-06-09 | Basf Se | Katalysator und verfahren zur herstellung eines amins |
RU2573570C2 (ru) | 2009-12-17 | 2016-01-20 | Басф Се | Превращение гликолевого альдегида со средством аминирования |
CN103420846B (zh) * | 2012-05-14 | 2015-02-11 | 浙江新化化工股份有限公司 | 一种生产异丙胺的方法 |
DE102012016433A1 (de) * | 2012-08-17 | 2014-05-15 | Oxea Gmbh | Kontinuierliches Verfahren zur Herstellung primärer aliphatischer Amine aus Aldehyden |
CN104277017B (zh) * | 2013-07-02 | 2016-04-13 | 中国科学院大连化学物理研究所 | 2,5-二羟甲基呋喃制备2,5-二甲胺基呋喃的方法 |
EP2883863B1 (de) * | 2013-12-11 | 2017-05-03 | Basf Se | Verfahren zur Hydrierung von 4,4'-Methylendianilin |
EP2883864A1 (de) * | 2013-12-11 | 2015-06-17 | Basf Se | Verfahren zur hydrierung aromatischer verbindungen |
US20180015443A1 (en) * | 2015-02-03 | 2018-01-18 | Gencell Ltd. | Nickel-based catalyst for the decomposition of ammonia |
CN108654679B (zh) * | 2018-05-03 | 2021-05-18 | 南京工业大学 | 一种提高香茅醛选择性加氢的负载型催化剂的应用 |
FR3142914A1 (fr) * | 2022-12-13 | 2024-06-14 | Fairbrics | Nouveau catalyseur hétérogène bimétallique, son procédé de préparation et son utilisation |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000212134A (ja) * | 1999-01-14 | 2000-08-02 | Basf Ag | N―エチル―ジイソプロピルアミンの製造方法 |
JP2001199939A (ja) * | 1999-12-06 | 2001-07-24 | Basf Ag | モノイソプロピルアミンの製法 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2618580B2 (de) | 1976-04-28 | 1980-07-03 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von Methylgruppen enthaltenden tertiären Aminen |
US4152353A (en) * | 1977-08-29 | 1979-05-01 | The Dow Chemical Company | Method of producing amines from alcohols, aldehydes, ketones and mixtures thereof |
EP0017651A1 (en) | 1977-08-29 | 1980-10-29 | The Dow Chemical Company | Improved method of producing amines from alcohols, aldehydes, ketones and mixtures thereof and catalyst used |
DE3903367A1 (de) * | 1989-02-04 | 1990-08-16 | Basf Ag | Katalysator und verfahren zur hydrierenden aminierung von alkoholen |
DE4116367A1 (de) | 1991-05-18 | 1992-11-19 | Basf Ag | Verfahren zur herstellung von aminen |
DE4428004A1 (de) * | 1994-08-08 | 1996-02-15 | Basf Ag | Verfahren zur Herstellung von Aminen |
DE19742911A1 (de) | 1997-09-29 | 1999-04-01 | Basf Ag | Verfahren zur Herstellung von Aminen |
DE19826396A1 (de) | 1998-06-12 | 1999-12-16 | Basf Ag | Verfahren zur Herstellung von Aminen |
DE19910960A1 (de) | 1999-03-12 | 2000-09-14 | Basf Ag | Verfahren zur Herstellung von Aminen |
ATE272605T1 (de) * | 1999-12-06 | 2004-08-15 | Basf Ag | Verfahren zur herstellung von aminen |
-
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Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000212134A (ja) * | 1999-01-14 | 2000-08-02 | Basf Ag | N―エチル―ジイソプロピルアミンの製造方法 |
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