ISOPHORONE DIAMINE

Isophorone diamine = IPDA 

CAS Number : 2855-13-2
EC Number: 220-666-8
Density: 0.922
Melting point: 10 °C (50 °F; 283 K)
Boiling point: 247 °C (477 °F; 520 K)
Chemical formula: C10H22N2
Molar mass: 170.300 g·mol−1

IPDA is a clear to light-yellow liquid. 
Isophorone diamine is highly soluble though slightly denser than water.
Isophorone diamine is corrosive to skin. 
IPDA is used to make other chemicals.
Isophorone diamine (usually shortened to IPDA) is a diamine with the formula (CH3)3C6H7(NH2)(CH2NH2). 
IPDA is a colorless liquid. 

Isophorone diamine is used as a hardner in heat cured epoxies.  
These hardeners are humidity resistant and have a less chance to form carbamates. 
Epoxy systems cured with Isophorone diamine have color stability and chemical resistance. 
In civil engineering applications like concrete protection, paving and repair, Isophorone diamine has applications as an epoxy-based self-levelling flooring systems. 

In the amine industry, Isophorone diamine is used to produce optically transparent and hard non-crystalline specialty polyamides. 
They are used as an intermediate to make leather, plastics, dyes and rubber products.  
Due to their weather properties, they are used in paving concreting and water proofing.   

Isophorone Diamine (IPDA) is an organic compound in the class known as isocyanates. 
More specifically, Isophorone diamine is an aliphatic diisocyanate. 
IPDA is produced in relatively small quantities, accounting for (with hexamethylene diisocyanate) only 3.4% of the global diisocyanate market in the year 2000. 
Isophorone Diamine (IPDA) is a cycloaliphatic amine based curing agent with low viscosity and moderate reactivity.
Isophorone Diamine (cis/trans Mixture) is one of the three epoxy networks based on diglycidyl ether of bisphenol-A epoxy prepolymer cured with aliphatic amines, namely triethylenetetramine (TETA), 1-(2-aminoethyl) piperazine (AEP) and isophoronediamine (IPD).

Applications of Isophorone diamine:
Isophorone Diamine (IPDA) is a cross linker for epoxy resins, building block for polyamides. 
IPDA is used in epoxy coatings, epoxy adhesives and epoxy composites. 
Isophorone diamine improves the hydrophobicity of epoxy resins with less sensitivity against humidity while film formation.
IPDA is a precursor to polymers and coatings.
Isophorone diamine is a cross linker for epoxy resins, building block for polyamides. 
Isophorone diamine is used in epoxy coatings, epoxy adhesives and epoxy composites. 
IPDA improves the hydrophobicity of epoxy resins with less sensitivity against humidity while film formation.

Uses of Isophorone diamine:
-Additive in adhesives and paints
-Biocides
-Dyes 
-Epoxy curing agent
-Isocyanates
-Leather productions
-Lubricant additive as scale and corrosion inhibitor
-Pesticides
-Pharmaceutical intermediates
-Plastics
-Polyamides for printing inks, dimer acids, textiles
-Rubber products
-Urethane and epoxy coatings for light-stable, weather-resistant properties
-Water proofing and paving concreting 
-Water treatment chemicals

Production
Isophorone diamine is usually produced as a mixture of the cis- and trans-isomers. 
Isophorone diamine is produced by hydrocyanation of isophorone followed by reductive amination and hydrogenation of the nitrile.
IPDA is used as a precursor in the manufacture of isophorone diisocyanate by phosgenation.

Like other diamines or amines in general, Isophorone diamine 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) Isophorone diamines higher cost compared to other amines is less critical as performance is the key criteria.
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 Isophorone diamine is not the only cycloaliphatic amine used in epoxy flooring, Isophorone diamine has the largest use by volume.
Other cycloaliphatic amines used in flooring include 1,3-BAC, MXDA, PACM and DCH-99.

Features of Isophorone diamine:
-High temperature resistance
-High mechanical strength
-Excellent chemical and moisture resistance
-Low color and good color stability

Applications of Isophorone diamine:
-Structural adhesive
-Flooring, grout, coating, etc. in construction
-Composite lamination
-Casting and encapsulation
-Heavy duty protective coating

Uses of Isophorone diamine:
One of the three epoxy networks based on diglycidyl ether of bisphenol-A epoxy prepolymer cured with aliphatic amines, namely triethylenetetramine (TETA), 1-(2-aminoethyl) piperazine (AEP) and isophoronediamine (IPD). 
Isophorondiamine mainly used as epoxy curing agents, mainly for applications requiring low color, low odor, high flexural strength and excellent chemical resistance of epoxy formulations. 
Isophorone diamine is suitable for floor coatings, fillers and paving mixes.

Features of Isophorone diamine:
-Characteristic peppermint-like smell
-Colorless to yellowish liquid
-Accurate composition
-Compatibility
-Low volatility
-Flexibility
-Excellent electrical characteristics
-Free from impurities
-Balanced chemical composition
-Nominal costs
-Precisely processed
-Long shelf life
 
Isophorone diamine [IPDA, 3-(aminomethyl)-3,5,5-trimethylcyclohexylamine] is a chiral non-C2-symmetric 1,4-diamine which is produced industrially on large scale as the mixture of all four stereoisomers (cis/trans ca. 3:1). 
Starting from this industrial bulk product, the preparation of the bis-tosyl, bis-Fmoc, bis-Boc and bis-Z derivatives of cis-IPDA, the preparation of the pure cis enantiomers by HPLC on chiral stationary phase, and the assignment of absolute configurations to the isolated enantiomers are described. 
We furthermore report an efficient method for the optical resolution of IPDA by salt formation with dibenzoyl tartaric acid. 
The latter method conveniently affords enantiomerically pure cis-IPDA in 100 g quantities. 
A number of salen ligands have been prepared from this enantiomerically pure 1,4-diamine and fully characterized. 
The nickel complex of one of the salen ligands was prepared and analyzed by X-ray crystallography. 
The crystal structure of the Ni4L4 complex illustrates the pronounced preference of cis-IPDA for adopting the chair conformation in which both the amino- and the aminomethyl substituents occupy equatorial positions. 
As a consequence, the two salicylidene imine moieties of one ligand molecule do not converge on one metal ion, but act as bridging ligands between two nickel ions.

Specifications & Other Information : 
Chemical Formula : C10H22N2
CAS Number : 2855-13-2
Molecular Weight : 170.30
Color No : 0.05
Water : 8
Aminonitrile : 0.06
Purity : 99.8

What is Isophorone diamine?
Isophorone diamine is common hardener for epoxy resin.

How do I avoid Isophorone diamine? 
You should avoid any contact with Isophorone diamine. 
Avoidance requires reading labels, package inserts, Material Safety Data Sheets (MSDS), and, on occasion, direct communication with the manufacturer.

An in-depth market share analysis, in terms of revenue, of the top companies is also included in the report. 
These numbers are arrived at based on key facts, annual financial information from SEC filings, annual reports, and interviews with industry experts, key opinion leaders such as CEOs, directors, and marketing executives. 
A detailed market share analysis of the major players in global isophorone diamine market has been covered in this report. 
Some of the major companies in this market are Evonic Industries, BASF SE, Bayer BMS, Perstorp etc.

Isophorone (IPHO) is used in many end markets such as agrochemicals, fine chemistry, coating, inks, epoxy systems, isocyanates.
IPHO, an unsaturated cyclic ketone, is a raw material in many chemical synthesis: IPDA/IPDI (isophorone diamine / isophorone diisocyanate), PCMX (antimicrobial derivatives of 3,5-xylenol), Trimethylcyclohexanone…
IPHO is also used as a solvent, especially in coatings, inks and agrochemicals.

Other names for Isophorone diamine: 
IPD
IPDA
5-Amino-1,3,3-Trimethyl Cyclohexanemethanamine
1-Amino-3-aminomethyl-3,5,5-trimethyl    cyclohexane
3-Aminomethyl-3,5,5-trimethyl cyclohexylamine

IUPAC name:
3-(Aminomethyl)-3,5,5-trimethylcyclohexan-1-amine
Other names:
Isophorondiamin
IPDA
Isophorone diamine is a mixture of stereoisomers for synthesis

Synonym(s): Isophoronediamine, 3-Aminomethyl-3,5,5-trimethylcyclohexylamine
Empirical Formula (Hill Notation): C10H22N2
CAS Number: 2855-13-2
Molecular Weight: 170.30
MDL number: MFCD00019397
EC Index Number: 220-666-8

Isophorone Diamine (IPDA) is an organic compound in the class known as isocyanates. 
More specifically, Isophorone diamine is an aliphatic diisocyanate. 
Isophorone diamine is produced in relatively small quantities, accounting for (with hexamethylene diisocyanate) only 3.4% of the global diisocyanate market in the year 2000. 
Isophorone Diamine (IPDA) is a cycloaliphatic amine based curing agent with low viscosity and moderate reactivity.

CAS Number: 2855-13-2 (isomeric mixture)
ChEMBL: ChEMBL1876029
ChemSpider: 16867
ECHA InfoCard: 100.018.788 
EC Number: 220-666-8
PubChem CID: 17857
UNII: X5WYA841BU 
UN number: 2289
CompTox Dashboard (EPA): DTXSID6027503

Isophorone diamine appearance ：
Isophoronediamine appears as a clear to light-yellow liquid. Highly soluble though slightly denser than water. 
May be toxic by inhalation and skin absorption. Corrosive to skin. Isophorone diamine is used to make other chemicals.

Isophorone diamine stability ：
Stable. 
Incompatible with strong oxidizing agents.

Specific Rotation ：
Specific optical rotation: 0 deg @ 20 °C/D (neat)

Description
Isophoronediamine is a colorless to yellow liquid with an amine-like odor. 
Isophorone diamine is fully miscible in water and soluble in other solvents.

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

Method for preparing isophorone diamine
Abstract
The invention discloses a method for preparing isophorone diamine, and is characterized in that the method comprises the following steps: 
1) under the condition of an organic amine catalyst, with isophorone and nitromethane as raw materials, synthesizing 3-nitromethyl-3,5,5-trimethylcyclohexanone, wherein the reaction temperature is 0 DEG C-150 DEG C, and the amount of the organic amine catalyst is 1-300% of the mass of the substance amount of isophorone; and 
2) under conditions of liquid ammonia, hydrogen and a metal cobalt catalyst, allowing 3-nitromethyl-3,5,5-trimethylcyclohexanone to undergo a reaction to generate isophorone diamine, wherein the reaction temperature is 30-300 DEG C, the liquid ammonia amount is 1-50 times of the substance amount of 3-nitromethyl-3,5,5-trimethylcyclohexanone, and the hydrogen pressure is 0.1-10 MPa. 
The nitromethane with lower toxicity is used for replacing highly-toxic hydrogen cyanide or thiocyanate, and thus the method is a technical route which is safer in process and friendlier to the environment.

storage conditions:Store below +30°C.
vapor pressure:0.02 hPa ( 20 °C)
Quality Level:200
autoignition temp.:380 °C
potency:1030 mg/kg LD50, oral (Rat)
expl. lim.:1.2 % (v/v)
pH:11.6 (20 °C, 10 g/L in H2O)
bp:247 °C/1013 hPa
mp:10 °C
transition temp:flash point 112 °C
density:0.92 g/cm3 at 20 °C
storage temp.:2-30°C
InChI:1S/C10H22N2.C7H8O3S/c1-9(2)4-8(12)5-10(3,6-9)7-11;1-6-2-4-7(5-3-6)11(8,9)10/h8H,4-7,11-12H2,1-3H3;2-5H,1H3,(H,8,9,10)
InChI key: ZBVBXDSQFYHMPD-UHFFFAOYSA-N

Using isophorone as the initial material, isophoronediamine was synthesized through three steps including cyanidation, imidization and hydrogenation. 
The reaction conditions of each reaction step were optimized. 
The optimized reaction conditions for the intermediate product isophoronenitrile are as follows: NH4Cl as an acidification reagent, DMF as a reaction medium, 0.0669 mol isophorone, 0.048 mol NaCN, 5 mL NH4Cl (6 mol·L-1), 70℃ and 4 h of reaction time. 
The yield of isophoronenitrile is 94.9%. 
The optimized reaction conditions for the intermediate product isophoroneimine are as follows: CaO as a catalyst, ammonia pressure 0.2 MPa, 70℃ and 4 h of reaction time. 
The conversion of isophoronenitrile is 97.4% and the yield of isophoroneimine is 87.6%. 
The optimized reaction conditions for isophoronediamine are as follows: reaction temperature 120℃, hydrogen pressure 6 MPa, ammonia pressure 0.2 MPa, 2 g Raney Co as catalyst and reaction time 8 h. 
The conversion of isophoroneimine is 100% and the yield of isophoronediamine is 95.6%. 
In addition, the structures of the intermediates and the final product were confirmed by IR, MS and 1H-NMR.

isophorone diamine
Where is isophorone diamine found?
Isophorone diamine is a polymer used to bind plastics.
How can you avoid contact with isophorone diamine?
Avoid products that list any of the following names in the ingredients:
-3-Aminomethyl-3,5,5-trimethylcyclohexylamine
-5-Amino-1,3,3-trimethylcyclohexanemethylamine
-CCRIS 6680
-Cyclohexanemethanamine, 5-amino
-1,3,3-trimethyl-
-Cyclohexanemethylamine, 5-amino
-1,3,3-trimethyl-
-EINECS 220-666-8
-HSDB 4058

What are some products that may contain isophorone diamine?
Household Products

Synonyms:
ipd;IPDA;DAIP;D 230;luxamipd;Epikure 943;vestaminipd;aminomethyl-5;aralditehy5083;chemamminaca17

Features of Isophorone diamine:
Characteristic peppermint-like smell
Colorless to yellowish liquid
Accurate composition
Compatibility
Low volatility
Flexibility
Excellent electrical characteristics
Free from impurities
Balanced chemical composition
Nominal costs
Precisely processed
Long shelf life

Isophorone diamine is a colorless to yellow liquid of low viscosity. 
IPDA is denser than water and highly soluble in it. 
Isophorone diamine is also miscible in alcohols, esters, ketones and ethers. 
Isophorone diamine is an amine and is thus a base. 
IPDA has an amine odor. 
Isophorone diamine has two amino groups, aromatic diamines and aliphatic diamines which are used to produce polyesters, nylons etc. where they are used as monomers. 
IPDA is a type of cycloaliphatic diamine and its peers are 1,2- diaminocyclohexane, 1,3-bis(aminomethyl)cyclohexane and 1,4-bis(aminocyclohexyl)methane.

Density: 0.9±0.1 g/cm3
Boiling Point: 217.2±8.0 °C at 760 mmHg
Melting Point: 10 °C(lit.)
Molecular Formula: C10H22N2
Molecular Weight: 170.295
Flash Point: 98.7±17.9 °C
Exact Mass: 170.178299
PSA: 52.04000
LogP: 1.68
Vapour Pressure: 0.1±0.4 mmHg at 25°C
Index of Refraction: 1.458
Stability: Stable. Incompatible with strong oxidizing agents.
Water Solubility: miscible

Isophorone Diamine (IPDA) is a cross linker for epoxy resins, building block for polyamides. 
Isophorone diamine is used in epoxy coatings, epoxy adhesives and epoxy composites. 
IPDA improves the hydrophobicity of epoxy resins with less sensitivity against humidity while film formation.

Specifications & Other Information about Isophorone diamine: 
Chemical Formula : C10H22N2
CAS Number : 2855-13-2
Molecular Weight : 170.30
Color No : 0.05
Water : 8
Aminonitrile : 0.06
Purity : 99.8

Formula: C10H22N2
Molecular mass: 170.30
Boiling point: 247°C
Melting point: 10°C
Relative density (water = 1): 0.92
Solubility in water: very good
Vapour pressure, Pa at 20°C: 2
Flash point: 117°C c.c., 110°C o.c.
Explosive limits, vol% in air: 1.2-? 

Isophorone diamine [IPDA, 3-(aminomethyl)-3,5,5-trimethylcyclohexylamine] is a chiral non-C2-symmetric 1,4-diamine which is produced industrially on large scale as the mixture of all four stereoisomers (cis/trans ca. 3:1). 
Starting from this industrial bulk product, the preparation of the bis-tosyl, bis-Fmoc, bis-Boc and bis-Z derivatives of cis-IPDA, the preparation of the pure cis enantiomers by HPLC on chiral stationary phase, and the assignment of absolute configurations to the isolated enantiomers are described. 
We furthermore report an efficient method for the optical resolution of IPDA by salt formation with dibenzoyl tartaric acid. 
The latter method conveniently affords enantiomerically pure cis-IPDA in 100 g quantities. 
A number of salen ligands have been prepared from this enantiomerically pure 1,4-diamine and fully characterized. 
The nickel complex of one of the salen ligands was prepared and analyzed by X-ray crystallography. 
The crystal structure of the Ni4L4 complex illustrates the pronounced preference of cis-IPDA for adopting the chair conformation in which both the amino- and the aminomethyl substituents occupy equatorial positions. 
As a consequence, the two salicylidene imine moieties of one ligand molecule do not converge on one metal ion, but act as bridging ligands between two nickel ions.

ISOPHORONE DIAMINE
2855-13-2
Isophoronediamine
Isophorondiamine
3-Aminomethyl-3,5,5-trimethylcyclohexylamine
Cyclohexanemethanamine, 5-amino-1,3,3-trimethyl-
3-(Aminomethyl)-3,5,5-trimethylcyclohexanamine
3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine
5-Amino-1,3,3-trimethylcyclohexanemethylamine
Cyclohexanemethylamine, 5-amino-1,3,3-trimethyl-
Isophoronediamine (cis- and trans- mixture)
1-Amino-3-aminomethyl-3,5,5-trimethylcyclohexane
DSSTox_CID_7503
DSSTox_RID_78476
DSSTox_GSID_27503
CAS-2855-13-2
IPDA
CCRIS 6680
HSDB 4058
3-(aminomethyl)-3,5,5-trimethylcyclohexylamine
Isophorondiamine, 99+%, mixture of cis and trans
EINECS 220-666-8
UN2289
Vestamin IPD
Araldite HY 5083
EC 220-666-8
SCHEMBL15383
SCHEMBL8745864
CHEMBL1876029
DTXSID6027503
Tox21_201401
Tox21_303122
ANW-43123
MFCD00019397
SBB061667
AKOS000120367
Isophorone Diamine (cis/trans Mixture)
MCULE-8499525000
UN 2289
NCGC00164044-01
NCGC00164044-02
NCGC00257083-01
NCGC00258952-01
LS-13908
Isophoronediamine [UN2289] [Corrosive]
FT-0627445
I0228
ST50406054
3,3,5-Trimethyl-5-aminomethylcyclohexylamine
5-Amino-1,3,3-trimethylcyclohexanemethanamine
3-Aminomethyl-3,5,5-trimethyl cyclohexylamine
1,3,3-Trimethyl-1-aminomethyl-5-aminocyclohexane
1-Amino-3,3,5-trimethyl-5-aminomethylcyclohexane
3-(Aminomethyl)-3,5,5-trimethylcyclohexanamine #
1-amino-3,3,5-trimethyl-5-aminomethyl cyclohexane
1-amino-3-aminomethyl-3,5,5-trimethyl cyclohexane
1-aminomethyl-5-amino-1,3,3-trimethyl cyclohexane
J-017123
Q1674522
1-Amino-3-(aminomethyl)-3,5,5-trimethylcyclohexane
F2191-0270
1-Amino-3-aminomethyl-3,5,5-trimethylcyclohexane (cis- and trans- mixture)
5-Amino-1,3,3-trimethylcyclohexanemethylamine, mixture of cis and trans, >=99%
5-Amino-1,3,3-trimethylcyclohexanemethanamine
5-Amino-1,3,3-trimethyl- cyclohexanemethylamine
5-Amino-1,3,3-trimethylcyclohexanemethylamine
Araldite HY 5083
Araldite HY 5161
Chemammina CA 17
D 230
Epikure 943
Epilox H 10-31
Epilox IPD
HY 3484
HY 5161
IPD
IPDA
Isophorone Diamine
LH 281
Luxam IPD
Polypox IPD
RIM 137
Rutadur SG
Rutapox H 550L
Vestamin IPD
Vestamine IPDA