1,2-Diaminocyclohexane

Last updated
1,2-Diaminocyclohexane
1,2-Diaminocyclohexane Structural Formulae V.1.svg
Names
Preferred IUPAC name
Cyclohexane-1,2-diamine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.010.707 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 211-776-7
PubChem CID
UNII
UN number 2735
  • InChI=1S/C6H14N2/c7-5-3-1-2-4-6(5)8/h5-6H,1-4,7-8H2
    Key: SSJXIUAHEKJCMH-UHFFFAOYSA-N
  • C1CCC(C(C1)N)N
Properties
C6H14N2
Molar mass 114.192 g·mol−1
Hazards
GHS labelling:
GHS-pictogram-acid.svg GHS-pictogram-exclam.svg
Danger
H302, H312, H314, H317, H332, H335
P260, P261, P264, P270, P271, P272, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P333+P313, P363, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

1,2-Diaminocyclohexane (DACH) is an organic compound with the formula (CH2)4(CHNH2)2. It is a mixture of three stereoisomers: cis-1,2-diaminocyclohexane and both enantiomers of trans-1,2-diaminocyclohexane. The mixture is a colorless, corrosive liquid, although older samples can appear yellow. It is often called DCH-99 and also DACH.

Contents

Manufacture

The product is available commercially, manufactured by the hydrogenation of o-phenylenediamine. The two trans enantiomers can be resolved by conversion to diastereomeric salts of various chiral acids. [1]

Uses

The product is an epoxy curing agent for use in Coatings, Adhesives, Sealants and Elastomers - CASE. [2] It is particularly useful in epoxy flooring. [3] It may also be reacted with diethyl maleate utilizing the Michael reaction to produce a polyaspartic compound of CAS number 481040-92-0. [4] It may also be used in lubricants. [5] The product is also advertised as being useful as a chelating agent in a variety of applications including oil production. [6] It also is used in downfield oil and gas wells where there is an acidic stream to prevent corrosion to the bore piles. [7]

See also

Related Research Articles

<span class="mw-page-title-main">Stereoisomerism</span> When molecules have the same atoms and bond structure but differ in 3D orientation

In stereochemistry, stereoisomerism, or spatial isomerism, is a form of isomerism in which molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in space. This contrasts with structural isomers, which share the same molecular formula, but the bond connections or their order differs. By definition, molecules that are stereoisomers of each other represent the same structural isomer.

<span class="mw-page-title-main">Epoxy</span> Type of material

Epoxy is the family of basic components or cured end products of epoxy resins. Epoxy resins, also known as polyepoxides, are a class of reactive prepolymers and polymers which contain epoxide groups. The epoxide functional group is also collectively called epoxy. The IUPAC name for an epoxide group is an oxirane.

<span class="mw-page-title-main">Meso compound</span> Optically inactive isomer in a set of stereoisomers

A meso compound or meso isomer is an optically inactive isomer in a set of stereoisomers, at least two of which are optically active. This means that despite containing two or more stereocenters, the molecule is not chiral. A meso compound is superposable on its mirror image. Two objects can be superposed if all aspects of the objects coincide and it does not produce a "(+)" or "(-)" reading when analyzed with a polarimeter. The name is derived from the Greek mésos meaning “middle”.

Triethylamine is the chemical compound with the formula N(CH2CH3)3, commonly abbreviated Et3N. It is also abbreviated TEA, yet this abbreviation must be used carefully to avoid confusion with triethanolamine or tetraethylammonium, for which TEA is also a common abbreviation. It is a colourless volatile liquid with a strong fishy odor reminiscent of ammonia. Like diisopropylethylamine (Hünig's base), triethylamine is commonly employed in organic synthesis, usually as a base.

(<i>E</i>)-Stilbene Chemical compound

(E)-Stilbene, commonly known as trans-stilbene, is an organic compound represented by the condensed structural formula C6H5CH=CHC6H5. Classified as a diarylethene, it features a central ethylene moiety with one phenyl group substituent on each end of the carbon–carbon double bond. It has an (E) stereochemistry, meaning that the phenyl groups are located on opposite sides of the double bond, the opposite of its geometric isomer, cis-stilbene. Trans-stilbene occurs as a white crystalline solid at room temperature and is highly soluble in organic solvents. It can be converted to cis-stilbene photochemically, and further reacted to produce phenanthrene.

<span class="mw-page-title-main">Trost ligand</span> Chemical compound

The Trost ligand is a diphosphine used in the palladium-catalyzed Trost asymmetric allylic alkylation. Other C2-symmetric ligands derived from trans-1,2-diaminocyclohexane (DACH) have been developed, such as the (R,R)-DACH-naphthyl ligand derived from 2-diphenylphosphino-1-naphthalenecarboxylic acid. Related bidentate phosphine-containing ligands derived from other chiral diamines and 2-diphenylphosphinobenzoic acid have also been developed for applications in asymmetric synthesis.

<span class="mw-page-title-main">Ethylenediamine</span> Chemical compound

Ethylenediamine (abbreviated as en when a ligand) is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a basic amine. It is a widely used building block in chemical synthesis, with approximately 500,000 tonnes produced in 1998. Ethylenediamine is the first member of the so-called polyethylene amines.

<span class="mw-page-title-main">Hexamethylenediamine</span> Chemical compound

Hexamethylenediamine or hexane-1,6-diamine, is the organic compound with the formula H2N(CH2)6NH2. The molecule is a diamine, consisting of a hexamethylene hydrocarbon chain terminated with amine functional groups. The colorless solid (yellowish for some commercial samples) has a strong amine odor. About 1 billion kilograms are produced annually.

<i>trans</i>-1,2-Diaminocyclohexane Chemical compound

trans-1,2-Diaminocyclohexane is an organic compound with the formula C6H10(NH2)2. This diamine is a building block for C2-symmetric ligands that are useful in asymmetric catalysis.

<span class="mw-page-title-main">Diphenylethylenediamine</span> Chemical compound

1,2-Diphenyl-1,2-ethylenediamine, DPEN, is an organic compound with the formula H2NCHPhCHPhNH2, where Ph is phenyl (C6H5). DPEN exists as three stereoisomers: meso and two enantiomers S,S- and R,R-. The chiral diastereomers are used in asymmetric hydrogenation. Both diastereomers are bidentate ligands.

<span class="mw-page-title-main">Jacobsen's catalyst</span> Chemical compound

Jacobsen's catalyst is the common name for N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane­diaminomanganese(III) chloride, a coordination compound of manganese and a salen-type ligand. It is used as an asymmetric catalyst in the Jacobsen epoxidation, which is renowned for its ability to enantioselectively transform prochiral alkenes into epoxides. Before its development, catalysts for the asymmetric epoxidation of alkenes required the substrate to have a directing functional group, such as an alcohol as seen in the Sharpless epoxidation. This compound has two enantiomers, which give the appropriate epoxide product from the alkene starting material.

<span class="mw-page-title-main">Bisphenol A diglycidyl ether</span> Chemical compound

Bisphenol A diglycidyl ether is an organic compound and is a liquid epoxy resin. The compound is a colorless viscous liquid. It is a key component of many epoxy resin formulations. Addition of further Bisphenol A and a catalyst and heat can produce Bisphenol A glycidyl ether epoxy resins of higher molecular weight that are solid.

<span class="mw-page-title-main">1,2-Diaminopropane</span> Chemical compound

1,2-Diaminopropane (propane-1,2-diamine) is organic compound with the formula CH3CH(NH2)CH2NH2. A colorless liquid, it is the simplest chiral diamine. It is used as a bidentate ligand in coordination chemistry.

4,4'-Diaminodicyclohexylmethane is the name for organic compounds with the formula CH2(C6H10NH2)2. It is classified as a diamine. In the epoxy industry it is often referred to as PACM, short for para-diamino­dicyclohexyl­methane. It is used as a curing agent for epoxy resins It finds particular use in epoxy flooring. Another use is to produce diisocyanates, which are precursors to polyurethanes. The mixture is a colorless solid, but typical samples are yellowish and oily. The compound is produced as a mixture of three isomers by the hydrogenation of methylenedianiline. These isomers are, in decreasing order of their yield from the hydrogenation, trans-trans, cis-trans, and a small amount of cis-cis.

<span class="mw-page-title-main">Isophorone diamine</span> Chemical compound

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<span class="mw-page-title-main">1,3-Bis(aminomethyl)cyclohexane</span> Chemical compound

1,3-bis(aminomethyl)cyclohexane (1,3-BAC) are a collection of organic compounds with the formula C6H10(CH2NH2)2. The compounds belong to the sub class cycloaliphatic amine. Their key use is as an epoxy resin curing agent.

<span class="mw-page-title-main">2-Methylpentamethylenediamine</span> Chemical compound

2-Methylpentamethylenediamine is an organic compound part of the amine family with the formula H2NCH2CH2CH2CH(CH3)CCH2NCH2. A colorless liquid, this diamine is obtained by the hydrogenation of 2-methylglutaronitrile. It is better known by the trade name "Dytek A".

In organic chemistry, amine value is a measure of the nitrogen content of an organic molecule. Specifically, it is usually used to measure the amine content of amine functional compounds. It may be defined as the number of milligrams of potassium hydroxide (KOH) equivalent to one gram of epoxy hardener resin. The units are thus mg KOH/g.

<span class="mw-page-title-main">C12–C13 alcohol glycidyl ether</span> Chemical compound

C12-C13 alcohol glycidyl ether is a mixture of organic chemicals in the glycidyl ether family. It is a mixture of mainly 12 and 13 carbon chain alcohols, also called fatty alcohols that have been glycidated. It is an industrial chemical used as a surfactant but primarily for epoxy resin viscosity reduction. It has the CAS number 120547-52-6.

2,3-Butanediamine are organic compounds with the formula CH3CH(NH2)CH(NH2)CH3. Three stereoisomers exist, meso and a pair of enantiomers. These diamines form complexes with transition metals.

References

  1. Kouklovsky, Cyrille; Langlois, Yves; Aguilar, Enrique; Fernández-García, Jesús M.; Sikervar, Vikas (2014). "(1S,2S)-1,2-Diaminocyclohexane". Encyclopedia of Reagents for Organic Synthesis. pp. 1–23. doi:10.1002/047084289x.rn00145.pub3. ISBN   978-0-470-84289-8.
  2. "Dytek DCH-99 by INVISTA - Paint & Coatings". www.ulprospector.com. Retrieved 2020-04-13.
  3. "A New Epoxy Curing Agent with Long Pot Life and Fast Cure". www.pcimag.com. Retrieved 2021-05-18.
  4. "Dytek DCH-99 | 1,2-Diaminocyclohexane". Dytek. Retrieved 2020-04-13.
  5. "US Patent for Non-aromatic based antioxidants for lubricants Patent (Patent # 9,273,266 issued March 1, 2016) - Justia Patents Search". patents.justia.com. Retrieved 2020-04-13.
  6. "Technical Data Sheet Dytek DCH 99" (PDF). Archived (PDF) from the original on 2020-08-19.
  7. Materials, Ascend. "FlexaTram-DAM". Ascend Performance Materials. Retrieved 2020-05-21.