Cyclohexylamine and Dicyclohexylamine

Carswell, T. S.; Morrill, H. L.

doi:10.1021/ie50335a011

Cited by 48 publications

(8 citation statements)

References 6 publications

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“…For the binary system of water + CHA, a miscibility gap is calculated with the NRTL model at high water concentrations. However, this system is homogeneous over the whole concentration range, but the VLE data [16][17][18] show a homogeneous maximum azeotrop at high water concentrations. Further calculations showed that the miscibility gap disappears if an R value above 1.1 is chosen, but then the deviations of the binary fit increase rapidly.…”

Section: Calculationsmentioning

confidence: 88%

Liquid−Liquid(−Liquid) Equilibria in Ternary Systems of Water + Cyclohexylamine + Aromatic Hydrocarbon (Toluene or Propylbenzene) or Aliphatic Hydrocarbon (Heptane or Octane)

2006

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Liquid-liquid equilibria and liquid-liquid-liquid equilibria were determined for (water + cyclohexylamine + toluene), (water + cyclohexylamine + propylbenzene), (water + cyclohexylamine + heptane), and (water + cyclohexylamine + octane) at temperatures of (298.15, 303.15, and 333.15) K at atmospheric pressure by photometric turbidity titration. The composition of conjugate phases was determined by gas-liquid chromatography or potentiometric titration and Karl Fischer titration. All systems show type I behavior since there is only one binary pair of partial miscible liquids. Surprisingly, the systems (water + cyclohexylamine + heptane) and (water + cyclohexylamine + octane) have a three-phase region in a limited temperature range. The data were predicted with the NRTL and the UNIQUAC models in comparison to the Elliott-Suresh-Donohue equation of state based on binary interaction parameters only.

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Section: Calculationsmentioning

confidence: 88%

Liquid−Liquid(−Liquid) Equilibria in Ternary Systems of Water + Cyclohexylamine + Aromatic Hydrocarbon (Toluene or Propylbenzene) or Aliphatic Hydrocarbon (Heptane or Octane)

2006

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“…65 Solid lines represent the results from equations of state for benzene by Thol et al 38 and cyclohexane by Zhou et al 39 as well as the DIPPR correlations 37 for the remaining substances. 67,68 benzene, 69 cyclohexanol, 70 phenol, 71,72 cyclohexylamine, 73,74 and aniline. 75,76 Solid lines represent the results from equations of state for benzene by Thol et al 38 and for cyclohexane by Zhou et al 39 as well as the DIPPR correlations 37 for the remaining substances.…”

Section: Methods and Computational Detailsmentioning

confidence: 99%

“…Clausius–Clapeyron plots: present molecular simulation results for cyclohexane (○), benzene (△), cyclohexanol (□), phenol (green triangles), cyclohexylamine (red squares), and aniline (blue circles) are compared with experimental data (corresponding cross symbols) for cyclohexane, , benzene, cyclohexanol, phenol, , cyclohexylamine, , and aniline. , Solid lines represent the results from equations of state for benzene by Thol et al and for cyclohexane by Zhou et al as well as the DIPPR correlations for the remaining substances.…”

Section: Methods and Computational Detailsmentioning

confidence: 99%

Understanding the Differing Fluid Phase Behavior of Cyclohexane + Benzene and Their Hydroxylated or Aminated Forms

2017

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The three binary mixtures cyclohexane + benzene, cyclohexanol + phenol, and cyclohexylamine + aniline exhibit qualitatively different vapor-liquid phase behavior, that is, azeotropic with a pressure maximum, azeotropic with a pressure minimum, and zeotropic, respectively. Employing molecular modeling and simulation, the COSMO-SAC model, and a cubic equation of state, the root of these effects is studied on the basis of phase equilibria, excess properties for volume, enthalpy, and Gibbs energy as well as microscopic structure. It is found that cyclohexane + benzene is characterized by more pronounced repulsive interactions, leading to pressure maximum azeotropy and a positive excess Gibbs energy. Functionalizing the aliphatic and aromatic rings with one amine group each introduces attractive hydrogen bonding interactions of moderate strength that counterbalance such that the mixture becomes zeotropic. The hydroxyl groups introduce strong hydrogen bonding interactions, leading to pressure minimum azeotropy and a negative excess Gibbs energy.

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“…Alternative historical synthetic routes and early (1905-1931) metal-catalyzed hydrogen additions under hydrogen pressure have been well reviewed (9). Increased efficiencies compared to those with Ni and Co catalysts are available from the more precious elements of the same subgroup, Ru and Rh.…”

Section: Manufacture and Processingmentioning

confidence: 99%

Amines, Cycloaliphatic

Casey¹

2003

Kirk-Othmer Encyclopedia of Chemical Technology

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Cycloaliphatic amines are comprised of a cyclic hydrocarbon structural component and an amine functional group external to that ring. Included in an extended cycloaliphatic amine definition are aminomethyl cycloaliphatics. Although some cycloaliphatic amine and diamine products have direct end use applications, their major function is as low cost organic intermediates sold as moderate volume specification products. For simple primary amines directly bonded to a cycloalkane by a single \documentclass{article}\usepackage{amssymb}\pagestyle{empty}\begin{document}${{\rm{C}}{\relbar \kern-5pt{\relbar}\kern-7pt{\relbar}}{\rm{N}}}$\end{document} bond to a secondary carbon the homologous series consists of cyclopropylamine, C 3 H 7 N; cyclobutylamine, C 4 H 9 N; cyclopentylamine, C 5 H 11 N; cyclohexylamine, C 6 H 13 N; cycloheptylamine, C 7 H 15 N; cyclooctylamine, C 8 H 17 N; and cyclododecylamine, C 12 H 25 N. Up through C 8 each is a colorless liquid at room temperature. There are numerous cycloaliphatic diamines. Cycloaliphatic amines are strong bases with chemistry similar to that of simpler primary, secondary, or tertiary amines. Salt formation with Brønsted and Lewis acids and exhaustive alkylation to form quaternary ammonium cations are part of the rich derivatization chemistry of these amines. Primary cycloaliphatic amines react with phosgene to form isocyanates. Cycloaliphatic diamines react with dicarboxylic acids or their chlorides, dianhydrides, diisocyanates and di‐ (or poly‐) epoxides as comonomers to form high molecular weight polyamides, polyimides, polyureas, and epoxies. Cycloaliphatic amine synthesis routes may be described as distinct synthetic methods, though practice often combines, or hybridizes, the steps. Among them are amination of cycloalkanols, reductive amination of cyclic ketones, ring reduction of cycloalkenylamines, and others. Larger volume cycloaliphatic amines and diamines are cyclohexylamine, isophoronediamine, methylenedi(cyclohexylamine), 3,3′‐dimethylmethylene/di(cyclohexylamine), dicyclohexylamine, dimethylcyclohexylamine, and 1,2‐cyclohexanediamine. Shipment of these liquid products is by nitrogen‐blanketed tank truck or tank car. Cycloaliphatic amines and diamines are extreme lung, skin, and eye irritatants. Before a 1/1/70 FDA ban (rescission proposed in early 1990), cyclamate noncaloric sweeteners were the major derivatives driving cyclohexylamine production. Cyclohexylamine condensed with mercaptobenzothiazole produces the large volume moderate rubber accelerator N ‐cyclohexyl‐2‐benzothiazolesulfenamide. 1,3‐Dicyclohexylcarbodiimide is an important peptide‐condensing agent and analytical reagent. trans ‐1,2‐Cyclohexanediamine is derivatized, then hydrolyzed to the tetraacetate and sold as a chelating agent. Methylenedi‐(cyclohexylisocyanate) (MDCHI, Desmodur W) is the dominant derivative of MDCHA and is used in light‐stable urethanes. Isophoronediisocyanate made by phosgenation of IPD competes effectively in this same polyurethane market, predominantly coatings, and is the major commercial application of isophoronediamine. A representative agrochemical application of cycloaliphatic amines is the crabgrass and weed control agent Siduron 1‐(2‐methylcyclohexyl)‐3‐phenylurea. Others are herbicides, Cycloate, used for sugar beets, and Hexazinone.

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Cyclohexylamine and Dicyclohexylamine

Cited by 48 publications

References 6 publications

Liquid−Liquid(−Liquid) Equilibria in Ternary Systems of Water + Cyclohexylamine + Aromatic Hydrocarbon (Toluene or Propylbenzene) or Aliphatic Hydrocarbon (Heptane or Octane)

Liquid−Liquid(−Liquid) Equilibria in Ternary Systems of Water + Cyclohexylamine + Aromatic Hydrocarbon (Toluene or Propylbenzene) or Aliphatic Hydrocarbon (Heptane or Octane)

Understanding the Differing Fluid Phase Behavior of Cyclohexane + Benzene and Their Hydroxylated or Aminated Forms

Amines, Cycloaliphatic

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