Amines, Aliphatic

Abstract

The article contains sections titled: 1. Introduction 2. General Chemical Properties 2.1. Salt Formation 2.2. Conversion to Carboxamides 2.3. Conversion to Sulfonamides 2.4. Reaction with Carbonyl Compounds 2.5. Reaction with Carbon Dioxide and Carbon Disulfide 2.6. Reaction with Epoxides 2.7. Alkylation 2.8. Formation of Isocyanates and Ureas 2.9. Reaction with Acrylonitrile 2.10. Formation of Isonitriles 2.11. Oxidation 2.12. Dealkylation 3. General Production Methods 3.1. Production from Alcohols 3.2. Production from Carbonyl Compounds 3.3. Production from Nitriles 3.4. Production from Alkyl Halides 3.5. Production from Nitro Compounds 3.6. Production from Olefins 3.7. Other Processes 4. Lower Alkylamines 4.1. Physical Properties 4.2. Storage and Transportation 4.3. Quality Specifications and Analysis 4.4. Production 4.5. Uses 4.6. Economic Aspects 5. Cycloalkylamines 6. Cyclic Amines 7. Fatty Amines 7.1. Properties 7.2. Production 7.3. Analysis and Quality Control 7.4. Uses 7.5. Economic Aspects 8. Diamines and Polyamines 8.1. Diamines 8.1.1. 1,2‐Diaminoethane (Ethylenediamine) 8.1.2. Diaminopropanes 8.1.3. Higher Diamines 8.2. Oligoamines and Polyamines 8.2.1. Physical Properties 8.2.2. Chemical Properties 8.2.3. Production, Analysis, and Uses 9. Chiral Amines 10. Toxicology and Occupational Health 10.1. General Aspects 10.2. Toxicology of Specific Amines 10.2.1. Alkylamines, Cyclic Amines, and Polyamines 10.2.2. Fatty Amines 11. Acknowledgment

Reductive Amination of 1-Hydroxy-2-propanone Over Nickel and Copper Catalysts

“…Higher reaction temperature results in the formation of thermodynamically more stable secondary, tertiary or cyclic amines with six-membered ring (pyrazines and/or piperazines). Actually, the formation of these substances is exothermic, whereas the reaction leading to primary amines is nearly thermoneutral 5,22 . The formed DMPIPs contain secondary nitrogen atoms in their molecules and, therefore, they can subsequently undergo the reductive amination to N-mono-or N,N-di-substituted dimethyl piperazines (N-SubDMPIPs).…”

“…This fact indicates a marked decrease in concentration of 2-APOL to as low as 30 %, whereas almost one third of the reaction mixture was 1,2-PDOL. It is generally known that the excess of ammonia has a positive effect on selectivity of amination reactions to primary amines 5,[23][24][25][26] . This method markedly suppressed formation of undesirable secondary and tertiary amines during the reductive amination of acetol.…”

“…From the economic point of view, the production of industrially important amino compounds usually starts from more available alcohols, the hydroxyl group of which is first converted to the more reactive carbonyl group on the surface of the metallic catalyst. Nucleophilic addition of amination agents to the carbonyl group then provides imines (R-N=C-R) or enamines (R-C=C-N-R) that are subsequently easily hydrogenated to particular primary, secondary, or tertiary amines [1][2][3][4][5] . Special group of amines is amino alcohols containing both hydroxyl and amino group in their molecule.…”

A ruthenium racemisation catalyst for the synthesis of primary amines from secondary amines

“…Scheme 2 Reversible deactivation of Ru(CpPh 5 )(CO) 2 Cl by NH 3 and primary amine, similar to the deactivation of Shvo's catalyst. C NMR (125.73 MHz, 298 K, CDCl 3 ) spectrum of complex 1 after addition of cyclohexylamine and heating to 60°C for 1 h (upper spectrum, A) and spectrum of complex 1 after reaction with NH 3 at 170°C for 1 h (lower spectrum), due to a low concentration, the carbonyl signals could not be observed.…”

“…1,2 For the production of primary amines, waste-free, selective protocols are highly desired with special emphasis on renewable resources such as bio-alcohols. 3 However, current industrial (heterogeneously catalysed) syntheses of amines from alcohols inevitably give mixtures of primary, secondary, and tertiary amines.…”