GB810844A - Improved process for the production of cycloaliphatic 1.2-diamines and the resultingproducts - Google Patents
Improved process for the production of cycloaliphatic 1.2-diamines and the resultingproductsInfo
- Publication number
- GB810844A GB810844A GB18393/56A GB1839356A GB810844A GB 810844 A GB810844 A GB 810844A GB 18393/56 A GB18393/56 A GB 18393/56A GB 1839356 A GB1839356 A GB 1839356A GB 810844 A GB810844 A GB 810844A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chloro
- cyclohexanone
- decalone
- diamino
- bromo
- 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
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 239000004202 carbamide Substances 0.000 abstract 3
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- 239000011230 binding agent Substances 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 238000005984 hydrogenation reaction Methods 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 abstract 2
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 2
- 239000011707 mineral Substances 0.000 abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
- 239000001117 sulphuric acid Substances 0.000 abstract 2
- 235000011149 sulphuric acid Nutrition 0.000 abstract 2
- OOHJPUAVIALYHA-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalene-1,2-diamine Chemical compound C1CCCC2C(N)C(N)CCC21 OOHJPUAVIALYHA-UHFFFAOYSA-N 0.000 abstract 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 abstract 1
- JFNPFFAEYZRVJS-UHFFFAOYSA-N 2-bromocycloheptan-1-one Chemical compound BrC1CCCCCC1=O JFNPFFAEYZRVJS-UHFFFAOYSA-N 0.000 abstract 1
- KDXYEWRAWRZXFT-UHFFFAOYSA-N 2-bromocyclohexan-1-one Chemical compound BrC1CCCCC1=O KDXYEWRAWRZXFT-UHFFFAOYSA-N 0.000 abstract 1
- NOOBPZPTDOIEMT-UHFFFAOYSA-N 2-bromocyclooctan-1-one Chemical compound BrC1CCCCCCC1=O NOOBPZPTDOIEMT-UHFFFAOYSA-N 0.000 abstract 1
- SDSZGDVXUFWFAA-UHFFFAOYSA-N 2-chlorocycloheptan-1-one Chemical compound ClC1CCCCCC1=O SDSZGDVXUFWFAA-UHFFFAOYSA-N 0.000 abstract 1
- CCHNWURRBFGQCD-UHFFFAOYSA-N 2-chlorocyclohexan-1-one Chemical compound ClC1CCCCC1=O CCHNWURRBFGQCD-UHFFFAOYSA-N 0.000 abstract 1
- VLRGXXKFHVJQOL-UHFFFAOYSA-N 3-chloropentane-2,4-dione Chemical compound CC(=O)C(Cl)C(C)=O VLRGXXKFHVJQOL-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 125000002993 cycloalkylene group Chemical group 0.000 abstract 1
- DBBUVLSRTWYISN-UHFFFAOYSA-N cycloheptane-1,2-diamine Chemical compound NC1CCCCCC1N DBBUVLSRTWYISN-UHFFFAOYSA-N 0.000 abstract 1
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 abstract 1
- 150000004985 diamines Chemical class 0.000 abstract 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- -1 halogen ketone Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract 1
- 239000012433 hydrogen halide Substances 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Cycloaliphatic-1,2-diamines of the formula: <FORM:0810844/IV (b)/1> wherein R is a divalent hydrocarbon radical with at least 4 carbon atoms and with 4-6 carbon atoms forming the direct link between the two valencies, which radical, together with the grouping <FORM:0810844/IV (b)/2> forms a cycloalkylene or bicycloalkylene radical, are made by heating a halogen ketone of the formula: <FORM:0810844/IV (b)/3> in presence of a hydrogen halide binding agent with urea, hydrogenating the imidazolone obtained of one of the following formul : <FORM:0810844/IV (b)/4> <FORM:0810844/IV (b)/5> to form an imidazolidone: <FORM:0810844/IV (b)/6> and hydrolysing this, advantageously in a mineral acid medium, to form the diamine. excess urea may be used in the first step as acid-binding agent. For the hydrogenation, nickel or platinum catalysts may be employed, and alcohols as solvents. The third hydrolysis stage may be effected with mineral acid, e.g. sulphuric or phosphoric acid. In examples, 2 - chloro - cyclohexanone, 2 - chloro - cycloheptanone, and chloro-2-decalone (produced by chlorinating 2-decalone) are each reacted with excess urea in diethyleneglycol diethyl ether, followed by hydrogenation, using Raney nickel, of the imidazolone to the imidazolidone, and hydrolysis of this with sulphuric acid to give 1,2 - diamino - cyclohexane, 1,2 - diamino - cycloheptane, and 1,2 - diamino - decalin respectively. Other starting materials specified are 2 - bromo - cyclohexanone, 3 - chloro - 1 - methyl - cyclohexanone - (2), 4 - chloro - 1 - methyl - cyclohexanone - (3), 3 - chloro - 1 - methyl - cyclohexanone - (4), 2 - bromo - cycloheptanone, 2 - bromo - cyclooctanone, 1 - chloro - 2 - decalone, 3 - chloro - 2 - decalone.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH810844X | 1955-06-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB810844A true GB810844A (en) | 1959-03-25 |
Family
ID=4538490
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB18393/56A Expired GB810844A (en) | 1955-06-16 | 1956-06-14 | Improved process for the production of cycloaliphatic 1.2-diamines and the resultingproducts |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB810844A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3167586A (en) * | 1961-11-06 | 1965-01-26 | Monsanto Co | Preparation of cis-1, 2-diaminocyclo-hexane |
-
1956
- 1956-06-14 GB GB18393/56A patent/GB810844A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3167586A (en) * | 1961-11-06 | 1965-01-26 | Monsanto Co | Preparation of cis-1, 2-diaminocyclo-hexane |
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