Page 177 - CW E-Magazine (11-3-2025)

Special Article 1 (11.03.2025)

Isophorone & derivatives – a techno-commercial profile

Isophorone (IP) is an organic compound that belongs to the cyclic enones and is an important solvent for various
areas of industry. The substance is produced from the simple ketone, acetone, in a multi-step aldol condensation
process. In each case, three molecules of the starting material combine to form one molecule of isophorone.
Intermediates of this process are diacetone alcohol and mesityl oxide.

Isophoronediamine (IPDA) is a cycloaliphatic amine with the formula (CH 3 ) 3 C 6 H 7 (NH 2 )(CH 2 NH 2 ). It is a
precursor to polymers and coatings.
Special Report
It is produced by hydrocyanation of isophorone followed by reductive amination and hydrogenation of the
nitrile. It is usually produced as a mixture of the cis- and trans-isomers.IPDA is used as a precursor in the
manufacture of isophorone diisocyanate (IPDI) by phosgenation.

Isophorone & derivatives – a techno-commercial
IPDI belongs to the class of aliphatic diisocyanates (ADI), which also include hexamethylene diisocyanate
(HDI), dicyclohexylmethane-4 ,4’-Diisocyanate (HMDI), methylcyclohexane diisocyanate (HTDI), xylylene
profi le diisocyanate (XDI), trimethylhexamethylene diisocyanate (TMDI), and tetramethyl-m-benzene dimethylene
diisocyanate (TMXDI).

sophorone (IP) is an organic com-
pound that belongs to the cyclic
Ienones and is an important solvent
for various areas of industry. The sub-
stance is produced from the simple
ketone, acetone, in a multi-step aldol Isophorone (IP) Isophoronediamine (IPDA) Isophorone diisocyanate (IPDI_

condensation process. In each case, for IPDA in 2017 and over $700-mn and the UV fi lter homosalate (P11).
Applications
three molecules of the starting mate- for IPDI in 2021. Additionally, IP is It can also be used as a solvent for
IP is used as a solvent in the production and processing of paints, varnishes, coatings, oils, fats, resins,
nitrocellulose, pesticides and adhesives.
rial combine to form one molecule a starting material for the manufactu- vinyl resins, lacquers, varnishes,

of isophorone. Intermediates of this ring of several important compounds paints and other coatings.
The most important products synthesized from IP are IPDA and IPDI with a market value of over $600-mn
process are diacetone alcohol and (Figure 1).
forIPDA in 2017 and over $700-mn for IPDI in 2021.Additionally, IP is a starting material for the
mesityl oxide. manufacturing of several important compounds (Figure 1).
3,3-Dimethylglutaric acid [4839-46-7]

 Ketoisophorone (P2) can be synthe- is manufactured from IP by oxida-
Ketoisophorone (P2) can be synthesized directly from IP but is often synthesized through the
•
Isophoronediamine (IPDA) is a sized directly from IP but is often tion with hydrogen peroxide in the
intermediate beta-IP (P1) via oxidation. Ketoisophorone is used to synthesize carotenoids, vitamin E,
and flavouring agents, and is used as a fragrance additive.
cycloaliphatic amine with the formula synthesized through the inter- presence of concentrated sulphuric acid
•
3,5-Xylenol (P3), produced via catalytic isomerization of IP, is a starting material for various products,
(CH ) C H (NH )(CH NH ). It is a mediate beta-IP (P1) via oxidation. or by ozonolysis in methanolic solution
such as the disinfectants 4-chloroxylenol (P4) and 2,4-dichloroxylenol, resins, the insecticide
2
7
6
2
3 3
2
precursor to polymers and coatings. Ketoisophorone is used to synthe- and subsequent oxidation with hydro-
Methiocarb, vitamin E, and DL-alpha-tocopherol acetate.
size carotenoids, vitamin E, and gen peroxide. This acid is used in the
• 3,3,5-trimethyl-1-cyclohexanon (P5), which is produced through partial hydrogenation of IP, can be
used as a solvent and for the synthesis of peroxide polymerization initiators. It can be oxidized by nitric
It is produced by hydrocyanation fl avouring agents, and is used as a manufacture of pesticides and lube oil
acid to 2,4,4- and 2,2,4-trimethyladipic acid (P6). P6 is used to produce 2,2,4-trimethylhexane-1,6-
of isophorone followed by reductive fragrance additive. additives.
diamine (P7) and 2,2,4-trimethylhexane-1,6-diol (P8). P7 can be used to synthesize polyamides and P8
is used for polyester synthesis.
amination and hydrogenation of the  3,5-Xylenol (P3), produced via cata-

nitrile. It is usually produced as a mix- lytic isomerization of IP, is a starting Like other diamines or amines in
• 3,3,5-Trimethyl-1-cyclohexanol (TMCH) (P9) is produced through the complete hydrogenation of IP.
It is used as a fragrance, as a fuel, and to produce vasodilator drugs, the combat agent EA 1511 (P10)
ture of the cis- and trans-isomers. IPDA material for various products, such general, IPDA is a curing agent for
and the UV filter homosalate (P11). It can also be used as a solvent for vinyl resins, lacquers,
is used as a precursor in the manufac- as the disinfectants 4-chloroxylenol epoxy resins. Epoxy coatings, cross-
varnishes, paints and other coatings.
(P4) and 2,4-dichloroxylenol, resins, linked with IPDA, are used as primers
ture of isophorone diisocyanate (IPDI) 3,3-Dimethylglutaric acid [4839-46-7] is manufactured from IP by oxidation with hydrogen peroxidein the
the insecticide Methiocarb, vitamin and intermediate layers because they
by phosgenation. presence of concentrated sulphuric acid or by ozonolysis in methanolic solution and subsequent oxidation with
E, and DL-alpha-tocopherol acetate. offer outstanding mechanical, chemical
hydrogen peroxide. This acid is used in the manufacture of pesticides and lube oil additives.

IPDI belongs to the class of ali-  3,3,5-trimethyl-1-cyclohexanon and water resistance. They are extre-
phatic diisocyanates (ADI), which also (P5), which is produced through mely durable and have excellent adhe-
include hexamethylene diisocyanate partial hydrogenation of IP, can be sion to a variety of substrates. Typical
(HDI), dicyclohexylmethane-4 ,4’-Di- used as a solvent and for the syn- applications include industrial fl oor-
isocyanate (HMDI), methylcyclohexane thesis of peroxide polymerization ings, marine & anticorrosive paints, as 1
diisocyanate (HTDI), xylylene diiso- initiators. It can be oxidized by well as high-performance composites.
cyanate (XDI), trimethylhexamethylene nitric acid to 2,4,4- and 2,2,4-
diisocyanate (TMDI), and tetramethyl-m- trimethyladipic acid (P6). P6 is Cycloaliphatic amines such as IPDA
benzene dimethylene diisocyanate used to produce 2,2,4-trimethyl- are also known to have lower yellow-
(TMXDI). hexane-1,6-diamine (P7) and 2,2,4- ing tendency than other amines and are
trimethylhexane-1,6-diol (P8). P7 thus used in coatings applications where
Applications can be used to synthesize poly- this feature is important for aesthetics.
IP is used as a solvent in the pro- amides and P8 is used for poly- Although it is not the only cycloaliphatic
duction and processing of paints, var- ester synthesis. amine used in epoxy fl ooring, it has the
nishes, coatings, oils, fats, resins, nitro-  3,3,5-Trimethyl-1-cyclohexanol largest use by volume. IPDI is one of
cellulose, pesticides and adhesives. (TMCH) (P9) is produced through the main aliphatic diisocyanates, being
the complete hydrogenation of IP. widely employed in polyurethanes
The most important products syn- It is used as a fragrance, as a fuel, production for coating applications.
thesized from IP are IPDA and IPDI and to produce vasodilator drugs, It is highly reactive, so it can undergo
with a market value of over $600-mn the combat agent EA 1511 (P10) several addition reactions across the
Chemical Weekly March 11, 2025 177
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