Isophorone diamine

Names
IUPAC name

3-(Aminomethyl)-3,5,5-trimethylcyclohexan-1-amine

Other names

Isophorondiamine; IPDA

Identifiers

CAS Number

* 2855-13-2 (isomeric mixture) Y

3D model (JSmol)

* Interactive image

ChEMBL |

* ChEMBL1876029

ChemSpider |

* 16867

EC Number |

* 220-666-8

PubChem CID

* 17857

UNII |

* X5WYA841BU Y

UN number | 2289

InChI

* InChI=1S/C10H22N2/c1-9(2)4-8(12)5-10(3,6-9)7-11/h8H,4-7,11-12H2,1-3H3

Key: RNLHGQLZWXBQNY-UHFFFAOYSA-N

SMILES

* CC1(CC(CC(C1)(C)CN)N)C

Properties

Chemical formula

| C10H22N2
Molar mass | 170.300 g·mol−1
Appearance  | Colourless liquid
Density | 0.922
Melting point |  10 °C (50 °F; 283 K)
Boiling point |  247 °C (477 °F; 520 K)

Solubility in water

| Very good

Refractive index (nD)

| 1.4880
Hazards
GHS pictograms |
GHS Signal word | Danger

GHS hazard statements

| H302, H312, H314, H317, H318, H412

GHS precautionary statements

| P260, P261, P264, P270, P272, P273, P280, P301+312, P301+330+331, P302+352, P303+361+353, P304+340, P305+351+338, P310, P312, P321, P322, P330, P333+313, P363, P405, P501
Flash point | 117°C

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Tracking categories (test):

* SizeSet

Isophorone diamine (usually shortened to IPDA) is a diamine with the formula (CH3)3C6H7(NH2)(CH2NH2). It is a colorless liquid. It is a precursor to polymers and coatings.[1]

## Contents

* 1 Production
* 2 Uses
* 3 See also
* 4 References
* 5 External links

## Production

It is usually produced as a mixture of the cis\- and trans-isomers. It is produced by hydrocyanation of isophorone followed by reductive amination and hydrogenation of the nitrile.[1]

## Uses

IPDA is used as a precursor in the manufacture of isophorone diisocyanate by phosgenation.[2]

Like other diamines or amines in general, it is a curing agent for epoxy resins. When used in coatings applications the higher cost compared to other amines is justified by the enhanced UV stability and thus lower yellowing tendency. In the production of Advanced composite materials (engineering) its higher cost compared to other amines is less critical as performance is the key criteria.[3][4] Cycloaliphatic amines such as IPDA also are known to have lower yellowing tendency than other amines and are thus used in coatings applications where this feature is important for aesthetics. Although it is not the only cycloaliphatic amine used in epoxy flooring, it has the largest use by volume.[5] Other cycloaliphatic amines used in flooring include 1,3-BAC, MXDA, PACM and DCH-99.

In laboratory tests, Tokyo Metropolitan University found that IPDA was able to remove more than 99 percent of CO2 from air with a concentration of 400 parts per million (ppm) – about the level currently in the atmosphere. This process also happened much faster than other carbon capture techniques, removing 201 millimoles of CO2 per hour, per mole of the compound. That’s at least twice as fast as other Direct Air Capture lab systems, and far faster than the leading artificial leaf device.

The pollutant separated out into flakes of a solid carbamic acid material, which could be removed from the liquid relatively easily. If need be, it can be converted back into gaseous CO2 by heating it to 60 °C (140 °F), which also releases the original liquid IPDA ready for reuse. Whether the carbon is kept as a solid or a gas, it can then be stored or reused in industrial or chemical processes. The research was published in the journal ACS Environmental Au.[6]

## See also

* Epoxy
* 1,3-BAC
* MXDA
* PACM
* DCH-99

## References

1. ↑ 1.0 1.1 Hardo Siegel, Manfred Eggersdorfer (2005). "Ketones". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a15_077. ISBN 9783527306732.
2. ↑ The polyurethanes book. Randall, David, Lee, Steve, 1941-. [Everberg, Belgium]: [Huntsman Polyurethanes]. 2002. ISBN 0470850418. OCLC 50479333. https://www.worldcat.org/oclc/50479333.
3. ↑ Pilato, Louis A.; Michno, Michael J. (1994-11-04) (in en). Advanced Composite Materials. Springer Science & Business Media. ISBN 9783540575634. https://books.google.com/books?id=O379nM3QZwsC&q=Advanced+Composite+Materials.
4. ↑ "Cycloaliphatic Amines - Hexion.com" (in en-US). http://www.hexion.com/en-us/chemistry/epoxy-resins-curing-agents-modifiers/curing-agents/cycloaliphatic-amines.
5. ↑ "A New Epoxy Curing Agent with Long Pot Life and Fast Cure" (in en). https://www.pcimag.com/articles/96269-a-new-epoxy-curing-agent-with-long-pot-life-and-fast-cure?v=preview.
6. ↑ Kikkawa, Soichi; Amamoto, Kazushi; Fujiki, Yu; Hirayama, Jun; Kato, Gen; Miura, Hiroki; Shishido, Tetsuya; Yamazoe, Seiji (2022-05-10). "Direct Air Capture of CO 2 Using a Liquid Amine–Solid Carbamic Acid Phase-Separation System Using Diamines Bearing an Aminocyclohexyl Group" (in en). ACS Environmental Au 2 (4): 354–362. doi:10.1021/acsenvironau.1c00065. ISSN 2694-2518. https://pubs.acs.org/doi/10.1021/acsenvironau.1c00065.

## External links

* "US Patent Cycloaliphatic Epoxy Curing Agent". https://patentimages.storage.googleapis.com/ba/99/97/9fe0d282e62410/US20120142816A1.pdf.
* Safety Data Sheet
* BASF Product Data
* Technical Data Sheet
* Three Bond Epoxy article

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Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Isophorone_diamine&oldid=2210056"
*[CID]: Compound ID
*[H302]: Harmful if swallowed
*[H312]: Harmful in contact with skin
*[H314]: Causes severe skin burns and eye damage
*[H317]: May cause an allergic skin reaction
*[H318]: Causes serious eye damage
*[H412]: Harmful to aquatic life with long lasting effects
*[P260]: Do not breathe dust/fume/gas/mist/vapours/spray
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P270]: Do not eat, drink or smoke when using this product
*[P272]: Contaminated work clothing should not be allowed out of the workplace
*[P273]: Avoid release to the environment
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P301+312]: IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell
*[P301+330+331]: IF SWALLOWED: Rinse mouth. Do NOT induce vomiting
*[P302+352]: IF ON SKIN: Wash with soap and water
*[P303+361+353]: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P310]: Immediately call a POISON CENTER or doctor/physician
*[P312]: Call a POISON CENTER or doctor/physician if you feel unwell
*[P321]: Specific treatment (see … on this label)
*[P322]: Specific measures (see … on this label)
*[P330]: Rinse mouth
*[P333+313]: If skin irritation or a rash occurs: Get medical advice/attention
*[P363]: Wash contaminated clothing before reuse
*[P405]: Store locked up
*[P501]: Dispose of contents/container to …