SK17042000A3 - Spôsob výroby aminonitrilu a diamínu - Google Patents
Spôsob výroby aminonitrilu a diamínu Download PDFInfo
- Publication number
- SK17042000A3 SK17042000A3 SK1704-2000A SK17042000A SK17042000A3 SK 17042000 A3 SK17042000 A3 SK 17042000A3 SK 17042000 A SK17042000 A SK 17042000A SK 17042000 A3 SK17042000 A3 SK 17042000A3
- Authority
- SK
- Slovakia
- Prior art keywords
- acid
- process according
- reaction mixture
- catalyst
- dinitrile
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 22
- 125000005219 aminonitrile group Chemical group 0.000 title claims abstract description 10
- 150000004985 diamines Chemical class 0.000 title claims abstract description 10
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 claims abstract description 30
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000011541 reaction mixture Substances 0.000 claims abstract description 24
- 239000003054 catalyst Substances 0.000 claims abstract description 18
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 6
- 150000007524 organic acids Chemical class 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 17
- 238000005984 hydrogenation reaction Methods 0.000 claims description 17
- KBMSFJFLSXLIDJ-UHFFFAOYSA-N 6-aminohexanenitrile Chemical compound NCCCCCC#N KBMSFJFLSXLIDJ-UHFFFAOYSA-N 0.000 claims description 14
- 229910017052 cobalt Inorganic materials 0.000 claims description 14
- 239000010941 cobalt Substances 0.000 claims description 14
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 14
- 238000004821 distillation Methods 0.000 claims description 14
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 10
- 239000012190 activator Substances 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- 239000007868 Raney catalyst Substances 0.000 claims description 8
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 8
- 229910052759 nickel Inorganic materials 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 7
- 229910052742 iron Inorganic materials 0.000 claims description 6
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 5
- -1 aromatic carboxylic acids Chemical class 0.000 claims description 5
- 229910052804 chromium Inorganic materials 0.000 claims description 5
- 239000011651 chromium Substances 0.000 claims description 5
- 239000011347 resin Substances 0.000 claims description 5
- 229920005989 resin Polymers 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052737 gold Inorganic materials 0.000 claims description 4
- 239000010931 gold Substances 0.000 claims description 4
- 229910052750 molybdenum Inorganic materials 0.000 claims description 4
- 239000011733 molybdenum Substances 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 229910052709 silver Inorganic materials 0.000 claims description 4
- 239000004332 silver Substances 0.000 claims description 4
- 239000010936 titanium Substances 0.000 claims description 4
- 229910052719 titanium Inorganic materials 0.000 claims description 4
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 4
- 229910052721 tungsten Inorganic materials 0.000 claims description 4
- 239000010937 tungsten Substances 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 4
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 229910052707 ruthenium Inorganic materials 0.000 claims description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052787 antimony Inorganic materials 0.000 claims description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 2
- 229910052797 bismuth Inorganic materials 0.000 claims description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 2
- 229910052793 cadmium Inorganic materials 0.000 claims description 2
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 2
- 150000002484 inorganic compounds Chemical class 0.000 claims description 2
- 229910010272 inorganic material Inorganic materials 0.000 claims description 2
- 229910052741 iridium Inorganic materials 0.000 claims description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 2
- 239000011133 lead Substances 0.000 claims description 2
- 239000000395 magnesium oxide Substances 0.000 claims description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 239000010948 rhodium Substances 0.000 claims description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims description 2
- 229910052718 tin Inorganic materials 0.000 claims description 2
- 239000011135 tin Substances 0.000 claims description 2
- 239000004408 titanium dioxide Substances 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims 1
- 229910044991 metal oxide Inorganic materials 0.000 claims 1
- 150000004706 metal oxides Chemical class 0.000 claims 1
- 229910052761 rare earth metal Inorganic materials 0.000 claims 1
- 150000002910 rare earth metals Chemical class 0.000 claims 1
- 229910052702 rhenium Inorganic materials 0.000 claims 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 abstract description 6
- 238000006243 chemical reaction Methods 0.000 abstract description 6
- 239000001361 adipic acid Substances 0.000 abstract description 3
- 235000011037 adipic acid Nutrition 0.000 abstract description 3
- 229920002302 Nylon 6,6 Polymers 0.000 abstract description 2
- 239000007791 liquid phase Substances 0.000 abstract description 2
- 230000003197 catalytic effect Effects 0.000 abstract 2
- 239000007792 gaseous phase Substances 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- 239000006227 byproduct Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000002585 base Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 235000011007 phosphoric acid Nutrition 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000010411 cooking Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- GDCJAPJJFZWILF-UHFFFAOYSA-N 2-ethylbutanedinitrile Chemical compound CCC(C#N)CC#N GDCJAPJJFZWILF-UHFFFAOYSA-N 0.000 description 2
- FRMJZJUVLPFLAB-UHFFFAOYSA-N 2-iminocyclopentane-1-carbonitrile Chemical compound N=C1CCCC1C#N FRMJZJUVLPFLAB-UHFFFAOYSA-N 0.000 description 2
- FPPLREPCQJZDAQ-UHFFFAOYSA-N 2-methylpentanedinitrile Chemical compound N#CC(C)CCC#N FPPLREPCQJZDAQ-UHFFFAOYSA-N 0.000 description 2
- XJMMNTGIMDZPMU-UHFFFAOYSA-N 3-methylglutaric acid Chemical compound OC(=O)CC(C)CC(O)=O XJMMNTGIMDZPMU-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- UJEJQKVERRRQQD-UHFFFAOYSA-N 2,3-dimethylbutanedinitrile Chemical compound N#CC(C)C(C)C#N UJEJQKVERRRQQD-UHFFFAOYSA-N 0.000 description 1
- FHKPTEOFUHYQFY-UHFFFAOYSA-N 2-aminohexanenitrile Chemical compound CCCCC(N)C#N FHKPTEOFUHYQFY-UHFFFAOYSA-N 0.000 description 1
- RVHOBHMAPRVOLO-UHFFFAOYSA-N 2-ethylbutanedioic acid Chemical compound CCC(C(O)=O)CC(O)=O RVHOBHMAPRVOLO-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- AVQYXBDAZWIFTO-UHFFFAOYSA-N dodecanedinitrile Chemical compound N#CCCCCCCCCCCC#N AVQYXBDAZWIFTO-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- BTZNPZMHENLISZ-UHFFFAOYSA-N fluoromethanesulfonic acid Chemical compound OS(=O)(=O)CF BTZNPZMHENLISZ-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- ZTOMUSMDRMJOTH-UHFFFAOYSA-N glutaronitrile Chemical compound N#CCCCC#N ZTOMUSMDRMJOTH-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910001867 inorganic solvent Inorganic materials 0.000 description 1
- 239000003049 inorganic solvent Substances 0.000 description 1
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- IAHFWCOBPZCAEA-UHFFFAOYSA-N succinonitrile Chemical compound N#CCCC#N IAHFWCOBPZCAEA-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
- C07C209/48—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (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 |
|---|---|---|---|
| FR9806426A FR2778661B1 (fr) | 1998-05-15 | 1998-05-15 | Procede de preparation d'aminonitrile et de diamine |
| PCT/FR1999/001127 WO1999059962A1 (fr) | 1998-05-15 | 1999-05-11 | Procede de preparation d'aminonitrile et de diamine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK17042000A3 true SK17042000A3 (sk) | 2002-02-05 |
Family
ID=9526586
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1704-2000A SK17042000A3 (sk) | 1998-05-15 | 1999-05-11 | Spôsob výroby aminonitrilu a diamínu |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US6384283B1 (id) |
| EP (1) | EP1077932B1 (id) |
| JP (1) | JP3845550B2 (id) |
| KR (1) | KR100387410B1 (id) |
| CN (1) | CN1176064C (id) |
| BR (1) | BR9910472B1 (id) |
| CA (1) | CA2332613A1 (id) |
| DE (1) | DE69909619T2 (id) |
| ES (1) | ES2198910T3 (id) |
| FR (1) | FR2778661B1 (id) |
| ID (1) | ID28025A (id) |
| PL (1) | PL344157A1 (id) |
| RU (1) | RU2210564C2 (id) |
| SK (1) | SK17042000A3 (id) |
| TW (1) | TW487694B (id) |
| UA (1) | UA57138C2 (id) |
| WO (1) | WO1999059962A1 (id) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100671976B1 (ko) * | 2005-02-21 | 2007-01-24 | 한국과학기술연구원 | 실리카 고체 촉매, 이의 제조방법 및 이를 이용한 ε-카프로락탐의 제조방법 |
| FR2892118B1 (fr) * | 2005-10-18 | 2010-12-10 | Rhodia Recherches & Tech | Procede de fabrication d'hexamethylene diamine et d'aminocapronitrile. |
| WO2007104663A1 (de) * | 2006-03-10 | 2007-09-20 | Basf Se | Mischoxid-katalysatoren |
| FR2902425B1 (fr) * | 2006-06-20 | 2008-07-18 | Rhodia Recherches & Tech | Procede de fabrication de diamines primaires |
| FR2944791B1 (fr) | 2009-04-27 | 2012-02-10 | Rhodia Operations | Procede de preparation de lactames. |
| CN102199283B (zh) * | 2011-04-14 | 2012-09-12 | 杭州师范大学 | 一种尼龙6树脂、尼龙6长丝及其制备方法 |
| CN105944732A (zh) * | 2016-05-20 | 2016-09-21 | 湘潭大学 | 一种双金属K、Fe掺杂的镍基活性炭催化剂的制备方法和应用 |
| CN106318867A (zh) * | 2016-08-18 | 2017-01-11 | 南京诺尔曼生物技术有限公司 | 一种培养箱的摇摆称重装置及其控制方法 |
| CN106085854B (zh) * | 2016-08-18 | 2019-10-11 | 南京诺尔曼生物技术有限公司 | 一种基于血液透析器的细胞培养装置 |
| CN107805203A (zh) * | 2017-11-15 | 2018-03-16 | 上海应用技术大学 | 一种己二胺的制备方法 |
| CN108084035A (zh) * | 2017-12-11 | 2018-05-29 | 大连理工大学 | 一种无碱条件下己二腈直接氢化制己二胺的方法 |
| CN111054432B (zh) * | 2019-12-16 | 2021-09-03 | 中国科学院大连化学物理研究所 | 用于制备己二胺的催化剂及其制备方法与应用 |
| CN111233703A (zh) * | 2020-02-24 | 2020-06-05 | 山东金石新材料有限公司 | 一种二元伯胺生产设备及采用该设备生产二元伯胺的方法 |
| CN111672494B (zh) * | 2020-06-10 | 2023-06-02 | 江苏扬农化工集团有限公司 | 用于合成己二胺中间体的复合催化剂的制备方法及该复合催化剂的应用 |
| CN114436852B (zh) * | 2020-11-03 | 2024-05-07 | 中国石油化工股份有限公司 | 己二腈加氢制备己二胺的方法 |
| CN113582853B (zh) * | 2021-08-02 | 2023-07-18 | 江苏扬农化工集团有限公司 | 一种从有机酰胺制备有机二胺的方法及装置 |
| CN119751264B (zh) * | 2024-12-26 | 2025-10-03 | 大连理工大学 | 一种局域电子环境调控的镍基催化剂催化对苯二甲腈连续加氢精制对苯二甲胺的方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5296628A (en) * | 1992-02-13 | 1994-03-22 | E. I. Du Pont De Nemours And Company | Preparation of 6-aminocapronitrile |
| BR9408460A (pt) * | 1993-12-28 | 1997-08-05 | Rhone Poulenc Chimie | Processo de hidrogenação catalítica de nitrilas em aminas com o auxílio de um catalisador do tipo níquel de raney |
| FR2722709B3 (fr) * | 1994-07-21 | 1996-09-06 | Rhone Poulenc Chimie | Catalyseur d'hydrogenation de nitriles en amines, son procede de preparation et procede d'hydrogenation en faisant application |
| FR2728259B1 (fr) * | 1994-12-14 | 1997-03-14 | Rhone Poulenc Chimie | Procede d'hemihydrogenation de dinitriles en aminonitriles |
| DE4446893A1 (de) * | 1994-12-27 | 1996-07-04 | Basf Ag | Verfahren zur Herstellung von aliphatischen alpha,omega-Aminonitrilen |
| FR2738757B1 (fr) * | 1995-09-15 | 1997-10-31 | Rhone Poulenc Fibres | Nouveaux composes metalliques utilisables comme catalyseurs |
| DE19636766A1 (de) * | 1996-09-10 | 1998-03-12 | Basf Ag | Verfahren zur gleichzeitigen Herstellung von 6-Aminocapronitril und Hexamethylendiamin |
-
1998
- 1998-05-15 FR FR9806426A patent/FR2778661B1/fr not_active Expired - Fee Related
-
1999
- 1999-05-11 DE DE69909619T patent/DE69909619T2/de not_active Expired - Lifetime
- 1999-05-11 CN CNB998062383A patent/CN1176064C/zh not_active Expired - Fee Related
- 1999-05-11 ES ES99918054T patent/ES2198910T3/es not_active Expired - Lifetime
- 1999-05-11 ID IDW20002357A patent/ID28025A/id unknown
- 1999-05-11 JP JP2000549581A patent/JP3845550B2/ja not_active Expired - Fee Related
- 1999-05-11 KR KR10-2000-7012815A patent/KR100387410B1/ko not_active Expired - Fee Related
- 1999-05-11 PL PL99344157A patent/PL344157A1/xx not_active Application Discontinuation
- 1999-05-11 BR BRPI9910472-5A patent/BR9910472B1/pt not_active IP Right Cessation
- 1999-05-11 RU RU2000131622/04A patent/RU2210564C2/ru not_active IP Right Cessation
- 1999-05-11 WO PCT/FR1999/001127 patent/WO1999059962A1/fr not_active Ceased
- 1999-05-11 EP EP99918054A patent/EP1077932B1/fr not_active Expired - Lifetime
- 1999-05-11 SK SK1704-2000A patent/SK17042000A3/sk unknown
- 1999-05-11 US US09/674,551 patent/US6384283B1/en not_active Expired - Fee Related
- 1999-05-11 CA CA002332613A patent/CA2332613A1/fr not_active Abandoned
- 1999-05-15 TW TW088107919A patent/TW487694B/zh not_active IP Right Cessation
- 1999-11-05 UA UA2000116385A patent/UA57138C2/uk unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR9910472A (pt) | 2001-01-09 |
| CA2332613A1 (fr) | 1999-11-25 |
| CN1301250A (zh) | 2001-06-27 |
| EP1077932B1 (fr) | 2003-07-16 |
| JP2002515478A (ja) | 2002-05-28 |
| PL344157A1 (en) | 2001-10-08 |
| KR100387410B1 (ko) | 2003-06-18 |
| BR9910472B1 (pt) | 2010-08-24 |
| JP3845550B2 (ja) | 2006-11-15 |
| DE69909619D1 (de) | 2003-08-21 |
| EP1077932A1 (fr) | 2001-02-28 |
| CN1176064C (zh) | 2004-11-17 |
| UA57138C2 (uk) | 2003-06-16 |
| WO1999059962A1 (fr) | 1999-11-25 |
| FR2778661A1 (fr) | 1999-11-19 |
| ES2198910T3 (es) | 2004-02-01 |
| KR20010100751A (ko) | 2001-11-14 |
| FR2778661B1 (fr) | 2000-06-16 |
| RU2210564C2 (ru) | 2003-08-20 |
| TW487694B (en) | 2002-05-21 |
| DE69909619T2 (de) | 2004-06-09 |
| ID28025A (id) | 2001-05-03 |
| US6384283B1 (en) | 2002-05-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SK17042000A3 (sk) | Spôsob výroby aminonitrilu a diamínu | |
| US20030065169A1 (en) | Process for the preparation of epsilon-caprolactam | |
| KR20040016821A (ko) | 6-아미노카프로산의 제조 방법 | |
| JP4040842B2 (ja) | ジニトリルのヘミ水素化方法 | |
| CZ81099A3 (cs) | Způsob současné výroby nitrilu kyseliny 6-aminokapronové a hexamethylendiaminu | |
| US6790994B2 (en) | Methods for hydrogenating nitrile functions into amine functions | |
| RU2000131622A (ru) | Способ получения аминонитрила и диамина | |
| US5557004A (en) | Process for production of aliphaticαωaminonitriles | |
| CN1264808C (zh) | 6－氨基己酸烷基酯的生产 | |
| CZ20004211A3 (cs) | Způsob přípravy aminonitrilu a diaminu | |
| US6384263B1 (en) | Process for making 3-hydroxyalkanelnitriles and conversion of the 3-hydroxyalkanelnitrile to an hydroxyaminoalkane | |
| US20020038047A1 (en) | Process to separate linear alkyl 5-formylvalerate | |
| SK13882001A3 (sk) | Spôsob hemihydrogenácie dinitrilov na aminonitrily |