GB1379250A - Catalytic hydrogenation of adiponitrile to hexamethylenediamine - Google Patents
Catalytic hydrogenation of adiponitrile to hexamethylenediamineInfo
- Publication number
- GB1379250A GB1379250A GB289873A GB289873A GB1379250A GB 1379250 A GB1379250 A GB 1379250A GB 289873 A GB289873 A GB 289873A GB 289873 A GB289873 A GB 289873A GB 1379250 A GB1379250 A GB 1379250A
- Authority
- GB
- United Kingdom
- Prior art keywords
- adiponitrile
- cyclohexanediol
- ammonia
- optionally
- hexamethylene diamine
- 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
Links
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 title abstract 6
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 title abstract 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 title 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- 229910021529 ammonia Inorganic materials 0.000 abstract 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 abstract 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 abstract 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 abstract 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 abstract 1
- BYACHAOCSIPLCM-UHFFFAOYSA-N 2-[2-[bis(2-hydroxyethyl)amino]ethyl-(2-hydroxyethyl)amino]ethanol Chemical compound OCCN(CCO)CCN(CCO)CCO BYACHAOCSIPLCM-UHFFFAOYSA-N 0.000 abstract 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 abstract 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 abstract 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 abstract 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229930195725 Mannitol Natural products 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- KVZJLSYJROEPSQ-UHFFFAOYSA-N cis-DMCH Natural products CC1CCCCC1C KVZJLSYJROEPSQ-UHFFFAOYSA-N 0.000 abstract 1
- PFURGBBHAOXLIO-OLQVQODUSA-N cis-cyclohexane-1,2-diol Chemical compound O[C@H]1CCCC[C@H]1O PFURGBBHAOXLIO-OLQVQODUSA-N 0.000 abstract 1
- 229930182830 galactose Natural products 0.000 abstract 1
- 239000008103 glucose Substances 0.000 abstract 1
- 229940015043 glyoxal Drugs 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 239000000594 mannitol Substances 0.000 abstract 1
- 235000010355 mannitol Nutrition 0.000 abstract 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 abstract 1
- 229940079877 pyrogallol Drugs 0.000 abstract 1
- 239000000600 sorbitol Substances 0.000 abstract 1
- PFURGBBHAOXLIO-PHDIDXHHSA-N trans-cyclohexane-1,2-diol Chemical compound O[C@@H]1CCCC[C@H]1O PFURGBBHAOXLIO-PHDIDXHHSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24642672A | 1972-04-21 | 1972-04-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1379250A true GB1379250A (en) | 1975-01-02 |
Family
ID=22930631
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB289873A Expired GB1379250A (en) | 1972-04-21 | 1973-01-19 | Catalytic hydrogenation of adiponitrile to hexamethylenediamine |
Country Status (9)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3917707A (en) * | 1974-07-31 | 1975-11-04 | Du Pont | Suppression of 1,2-diaminocyclohexane formation during production of hexamethylenediamine |
| US4235821A (en) * | 1979-02-01 | 1980-11-25 | Suntech, Inc. | Hydrogenation of aliphatic nitriles to primary amines |
| JPS5848590U (ja) * | 1981-09-30 | 1983-04-01 | 日野自動車株式会社 | トレ−ラに使用される空気整流装置 |
| DE3231193A1 (de) * | 1982-08-21 | 1984-02-23 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von primaeren aminen |
| DE102006006625A1 (de) * | 2006-02-14 | 2007-08-16 | Degussa Gmbh | Verfahren zur Herstellung von Aminen durch Konditionierung des Katalysators mit Ammoniak |
| CN113248389A (zh) * | 2021-05-20 | 2021-08-13 | 重庆华峰化工有限公司 | 一种1,2-环己二胺的生产系统及方法 |
-
0
- BE BE794577D patent/BE794577A/xx not_active IP Right Cessation
-
1972
- 1972-04-21 US US00246426A patent/US3773834A/en not_active Expired - Lifetime
-
1973
- 1973-01-19 GB GB289873A patent/GB1379250A/en not_active Expired
- 1973-01-24 CA CA161,910A patent/CA1005463A/en not_active Expired
- 1973-01-24 IT IT19567/73A patent/IT978436B/it active
- 1973-01-30 DE DE2304264A patent/DE2304264C2/de not_active Expired
- 1973-01-30 FR FR7303248A patent/FR2180654B1/fr not_active Expired
- 1973-01-31 NL NLAANVRAGE7301393,A patent/NL178071C/xx not_active IP Right Cessation
- 1973-01-31 JP JP1207273A patent/JPS5735177B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL178071B (nl) | 1985-08-16 |
| BE794577A (fr) | 1973-07-26 |
| JPS4918807A (US07223432-20070529-C00017.png) | 1974-02-19 |
| NL178071C (nl) | 1986-01-16 |
| FR2180654B1 (US07223432-20070529-C00017.png) | 1976-09-10 |
| US3773834A (en) | 1973-11-20 |
| NL7301393A (US07223432-20070529-C00017.png) | 1973-10-23 |
| DE2304264C2 (de) | 1982-09-16 |
| FR2180654A1 (US07223432-20070529-C00017.png) | 1973-11-30 |
| CA1005463A (en) | 1977-02-15 |
| IT978436B (it) | 1974-09-20 |
| JPS5735177B2 (US07223432-20070529-C00017.png) | 1982-07-27 |
| DE2304264A1 (de) | 1973-11-08 |
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|---|---|---|
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| GB1379250A (en) | Catalytic hydrogenation of adiponitrile to hexamethylenediamine | |
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| GB1419767A (en) | Cobalt oxide catalysts | |
| FR2226388A1 (en) | Epsilon-aminocaproamide prodn in liq. ammonia - by catalytic hydrogen-ation of epsilon -nitrocaproamide under pressure | |
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| ES438734A1 (es) | Procedimiento para la obtencion de acetoxibutanol. | |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |