UA72839C2 - A method for hemihydrogenation of dinitriles into aminonitriles - Google Patents
A method for hemihydrogenation of dinitriles into aminonitriles Download PDFInfo
- Publication number
- UA72839C2 UA72839C2 UA20031211969A UA20031211969A UA72839C2 UA 72839 C2 UA72839 C2 UA 72839C2 UA 20031211969 A UA20031211969 A UA 20031211969A UA 20031211969 A UA20031211969 A UA 20031211969A UA 72839 C2 UA72839 C2 UA 72839C2
- Authority
- UA
- Ukraine
- Prior art keywords
- reaction medium
- fact
- mass
- catalyst
- differs
- Prior art date
Links
- 125000005219 aminonitrile group Chemical group 0.000 title claims abstract description 24
- 238000000034 method Methods 0.000 title claims description 50
- 239000003054 catalyst Substances 0.000 claims abstract description 34
- 229910052703 rhodium Inorganic materials 0.000 claims abstract description 7
- 239000010948 rhodium Substances 0.000 claims abstract description 7
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000007868 Raney catalyst Substances 0.000 claims abstract description 4
- 229910000564 Raney nickel Inorganic materials 0.000 claims abstract description 4
- 239000012429 reaction media Substances 0.000 claims description 27
- 238000005984 hydrogenation reaction Methods 0.000 claims description 21
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 150000004985 diamines Chemical class 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 10
- 238000005275 alloying Methods 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 150000007529 inorganic bases Chemical class 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- 229910052759 nickel Inorganic materials 0.000 claims description 8
- 229910021529 ammonia Inorganic materials 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 7
- 150000002910 rare earth metals Chemical class 0.000 claims description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 229910052741 iridium Inorganic materials 0.000 claims description 5
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 229910052797 bismuth Inorganic materials 0.000 claims description 3
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- 239000010936 titanium Substances 0.000 claims description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 239000011651 chromium Substances 0.000 claims description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052737 gold Inorganic materials 0.000 claims description 2
- 239000010931 gold Substances 0.000 claims description 2
- 229910052735 hafnium Inorganic materials 0.000 claims description 2
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 2
- 229910052758 niobium Inorganic materials 0.000 claims description 2
- 239000010955 niobium Substances 0.000 claims description 2
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
- 239000004332 silver Substances 0.000 claims description 2
- 229910052715 tantalum Inorganic materials 0.000 claims description 2
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- 229910052726 zirconium Inorganic materials 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims 1
- 239000002019 doping agent Substances 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052738 indium Inorganic materials 0.000 abstract 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 22
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 12
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 239000000654 additive Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 4
- 229910045601 alloy Inorganic materials 0.000 description 4
- 239000000956 alloy Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- FHKPTEOFUHYQFY-UHFFFAOYSA-N 2-aminohexanenitrile Chemical compound CCCCC(N)C#N FHKPTEOFUHYQFY-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- FPPLREPCQJZDAQ-UHFFFAOYSA-N 2-methylpentanedinitrile Chemical compound N#CC(C)CCC#N FPPLREPCQJZDAQ-UHFFFAOYSA-N 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 239000001099 ammonium carbonate Substances 0.000 description 2
- 235000011162 ammonium carbonates Nutrition 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 230000001143 conditioned effect Effects 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- -1 ethylsuccinitrile Chemical compound 0.000 description 1
- ZTOMUSMDRMJOTH-UHFFFAOYSA-N glutaronitrile Chemical compound N#CCCCC#N ZTOMUSMDRMJOTH-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002825 nitriles Chemical group 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003839 salts Chemical class 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
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 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
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 |
|---|---|---|---|
| FR0108248A FR2826363B1 (fr) | 2001-06-22 | 2001-06-22 | Procede d'hemihydrogenation de dinitriles en aminonitriles |
| PCT/FR2002/002019 WO2003000650A2 (fr) | 2001-06-22 | 2002-06-13 | Procede d'hemihydrogenation de dinitriles en aminonitriles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA72839C2 true UA72839C2 (en) | 2005-04-15 |
Family
ID=8864650
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA20031211969A UA72839C2 (en) | 2001-06-22 | 2002-06-13 | A method for hemihydrogenation of dinitriles into aminonitriles |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US7385074B2 (ru) |
| EP (1) | EP1397345B1 (ru) |
| JP (1) | JP4323310B2 (ru) |
| KR (1) | KR20040010754A (ru) |
| CN (1) | CN1241906C (ru) |
| BR (1) | BR0211038A (ru) |
| CA (1) | CA2449120A1 (ru) |
| DE (1) | DE60223804T2 (ru) |
| FR (1) | FR2826363B1 (ru) |
| HU (1) | HUP0400303A2 (ru) |
| IL (1) | IL159102A0 (ru) |
| MX (1) | MXPA03011646A (ru) |
| PL (1) | PL367765A1 (ru) |
| RU (1) | RU2260588C1 (ru) |
| SK (1) | SK15892003A3 (ru) |
| TW (1) | TWI301479B (ru) |
| UA (1) | UA72839C2 (ru) |
| WO (1) | WO2003000650A2 (ru) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2892118B1 (fr) | 2005-10-18 | 2010-12-10 | Rhodia Recherches & Tech | Procede de fabrication d'hexamethylene diamine et d'aminocapronitrile. |
| FR2905948B1 (fr) * | 2006-09-19 | 2008-10-24 | Rhodia Recherches & Tech | Procede de fabrication d'amines par hydrogenation de composes nitriles |
| FR2944791B1 (fr) | 2009-04-27 | 2012-02-10 | Rhodia Operations | Procede de preparation de lactames. |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4446893A1 (de) * | 1994-12-27 | 1996-07-04 | Basf Ag | Verfahren zur Herstellung von aliphatischen alpha,omega-Aminonitrilen |
| FR2785608B1 (fr) * | 1998-11-05 | 2000-12-29 | Rhone Poulenc Fibres | Procede d'hemihydrogenation de dinitriles |
| US6156694A (en) * | 1998-11-05 | 2000-12-05 | E. I. Dupont De Nemours & Company | Raney cobalt catalyst and a process for hydrogenating organic compounds using said catalyst |
-
2001
- 2001-06-22 FR FR0108248A patent/FR2826363B1/fr not_active Expired - Fee Related
-
2002
- 2002-06-13 US US10/481,027 patent/US7385074B2/en not_active Expired - Fee Related
- 2002-06-13 BR BR0211038-5A patent/BR0211038A/pt not_active IP Right Cessation
- 2002-06-13 EP EP02780840A patent/EP1397345B1/fr not_active Expired - Lifetime
- 2002-06-13 PL PL02367765A patent/PL367765A1/xx unknown
- 2002-06-13 IL IL15910202A patent/IL159102A0/xx unknown
- 2002-06-13 CA CA002449120A patent/CA2449120A1/fr not_active Abandoned
- 2002-06-13 RU RU2004101605/04A patent/RU2260588C1/ru not_active IP Right Cessation
- 2002-06-13 JP JP2003507057A patent/JP4323310B2/ja not_active Expired - Fee Related
- 2002-06-13 HU HU0400303A patent/HUP0400303A2/hu unknown
- 2002-06-13 DE DE60223804T patent/DE60223804T2/de not_active Expired - Lifetime
- 2002-06-13 MX MXPA03011646A patent/MXPA03011646A/es unknown
- 2002-06-13 CN CNB028124464A patent/CN1241906C/zh not_active Expired - Fee Related
- 2002-06-13 UA UA20031211969A patent/UA72839C2/uk unknown
- 2002-06-13 SK SK1589-2003A patent/SK15892003A3/sk unknown
- 2002-06-13 WO PCT/FR2002/002019 patent/WO2003000650A2/fr active IP Right Grant
- 2002-06-13 KR KR10-2003-7016655A patent/KR20040010754A/ko not_active Application Discontinuation
- 2002-06-21 TW TW091113650A patent/TWI301479B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| TWI301479B (en) | 2008-10-01 |
| RU2004101605A (ru) | 2005-07-10 |
| WO2003000650A2 (fr) | 2003-01-03 |
| CN1518537A (zh) | 2004-08-04 |
| HUP0400303A2 (hu) | 2004-08-30 |
| FR2826363A1 (fr) | 2002-12-27 |
| CA2449120A1 (fr) | 2003-01-03 |
| WO2003000650A3 (fr) | 2003-02-20 |
| IL159102A0 (en) | 2004-05-12 |
| DE60223804D1 (de) | 2008-01-10 |
| MXPA03011646A (es) | 2004-04-02 |
| RU2260588C1 (ru) | 2005-09-20 |
| EP1397345B1 (fr) | 2007-11-28 |
| SK15892003A3 (sk) | 2004-05-04 |
| KR20040010754A (ko) | 2004-01-31 |
| EP1397345A2 (fr) | 2004-03-17 |
| PL367765A1 (en) | 2005-03-07 |
| US7385074B2 (en) | 2008-06-10 |
| CN1241906C (zh) | 2006-02-15 |
| US20040220423A1 (en) | 2004-11-04 |
| JP2004530718A (ja) | 2004-10-07 |
| FR2826363B1 (fr) | 2005-01-14 |
| BR0211038A (pt) | 2004-06-22 |
| DE60223804T2 (de) | 2009-04-30 |
| JP4323310B2 (ja) | 2009-09-02 |
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