Method for manufacture of isophoronediamine

Patent metadata

Field	Value
Publication number	US-2025304525-A1
Application number	US-202218277233-A
Country	US
Kind code	A1
Filing date	Feb 10, 2022
Priority date	Feb 16, 2021
Publication date	Oct 2, 2025
Grant date	—

Abstract

A process for the manufacture of isophorone diamine (IPDA), comprising the steps of:a) providing a feed stream comprising trans-IPDA, cis-IPDA, isophorone nitrile amine (IPNA), components having a lower boiling point than trans-IPDA and components having a higher boiling point than IPNA, including isophorone amino alcohol (IPAA) and components having a higher boiling point than IPAA;b) separating the feed stream into(i) a fraction (ii) comprising a higher mass fraction of cis-IPDA content, compared to the feed stream;(ii) a fraction (iii) comprising a higher mass fraction of IPNA compared to the feed stream and a higher mass fraction of components having a boiling point higher than the boiling point of IPNA, including IPAA and components having a higher boiling point than IPAA, compared to the feed stream and optionally IPDA;c) further separating fraction (iii) into(iii) a fraction (iii-1) comprising a higher mass fraction of IPDA, compared to fraction (iii); and/or(iv) a fraction (iii-3) comprising a higher mass fraction of IPAA, compared to fraction (iii).

First claim

1 . A process for the manufacture of isophorone diamine (IPDA), comprising the steps of:
a) providing a feed stream comprising trans-IPDA, cis-IPDA, isophorone nitrile amine (IPNA), components having a lower boiling point than trans-IPDA and components having a higher boiling point than IPNA, including isophorone amino alcohol (IPAA) and components having a higher boiling point than IPAA; b) separating the feed stream into
(i) a fraction (ii) comprising a higher mass fraction of cis-IPDA content, compared to the feed stream;
(ii) a fraction (iii) comprising a higher mass fraction of IPNA compared to the feed stream and a higher mass fraction of components having a boiling point higher than the boiling point of IPNA, including IPAA and components having a higher boiling point than IPAA, compared to the feed stream and optionally IPDA;
c) further separating fraction (iii) into
(iii) a fraction (iii- 1 ) comprising a higher mass fraction of IPDA, compared to fraction (iii); and/or
(iv) a fraction (iii- 3 ) comprising a higher mass fraction of IPAA, compared to fraction (iii).

2 . A process according to claim 1 , wherein the feed stream is separated into an additional fraction (i) comprising a higher mass fraction of trans-IPDA, compared to the feed stream.

3 . A process according to at least one of claims 1 to 2 , wherein the feed stream is separated into an additional fraction (iv) comprising a higher mass fraction of components having a boiling point lower than trans-IPDA compared to the feed stream.

4 . A process according to claim 3 , wherein fraction (iv) is further separated into an organic phase (iv-a) and an aqueous phase (iv-b).

5 . A process according to at least one of claims 1 to 4 , wherein fraction (iii) is further separated into one or more of the following fractions:
a fraction (iii- 2 ) comprising a higher mass fraction of IPNA compared to fraction (iii); and/or a fraction (iii- 4 ) comprising a higher mass fraction of components having a boiling point higher than IPAA compared to fraction (iii).

6 . A process according to at least one of claims 1 to 5 , wherein fraction (iii) is separated into a fraction (iii- 1 ); and a fraction (iii-b), which comprises fractions (iii- 2 ), (iii- 3 ) and (iii- 4 ).

7 . A process according to claim 6 , wherein fraction (iii-b) is further separated in fractions (iii- 2 ), (iii- 3 ) and (iii- 4 ) in an additional column.

8 . A process according to at least one of claims 1 to 5 , wherein fraction (iii) is separated into fractions (iii- 1 ), (iii- 2 ), (iii- 3 ) and (iii- 4 ) in a single column.

9 . A process according to at least one of claims 1 to 5 , wherein fraction (iii) is separated into a fraction (iii-a), comprising fraction (iii- 2 ) and fraction (iii- 1 ); and
into a fraction (iii- 3 ); and into a fraction (iii- 4 ) in a single column.

10 . A process according to claims 6, 7 or 8 , wherein the cis-trans ratio (CTR) of IPDA in the feed is 75:25 or less.

11 . A process according to claim 9 , wherein the cis-trans ratio (CTR) of IPDA in the feed is 75:25 or more.

12 . A process according to claim 10 or 11 , wherein the feed stream comprises:
83.4 to 91.0 percent by weight: IPDA (cis and trans); 7-10 percent by weight: water; 0.5-2.5 percent by weight: components having a boiling point lower than trans-IPDA; 0.1 to 0.4 percent by weight: IPNA; 1 to 3 percent by weight: IPAA; 0.4 to 0.7 percent by weight: components having a boiling point higher than IPAA.

13 . A process according to at least of claims 1 to 10 wherein the feed stream is obtained by either (A) converting isophorone nitrile (IPN) in the presence of NH 3 , H 2 and a hydrogenation catalyst in a single step or (B) converting IPN in the presence of NH 3 , H 2 and a hydrogenation catalyst in at least two stages, by first converting IPN fully or partly with NH 3 in the presence of an imination catalyst to obtain isophorone nitrile imine (IPNI) and further reacting IPNI with hydrogen in the presence of a hydrogenation catalyst and optionally ammonia.

14 . A process according to at least one of claims 1 to 13 wherein fraction (i) and/or fraction (ii) each comprise less than 0.2 percent by weight of IPNA.

15 . A process according to claim 14 and carrying out an additional step in which the IPDA of fraction (i) is converted to isophone diisocyanate (IPDI) by conversion of IPDA of fraction (i) with phosgene to IPDI and optionally carrying out an additional step by converting IPDI with polyols to obtain polyurethanes.

16 . A process according to at least one of claims 1 to 15 , wherein feed stream is prepared comprising the steps of
I) converting isophorone (IP) and hydrogen cyanide (HCN) to isophorone nitrile (IPN); II) converting IPN to isophoronenitrile imine (IPNI) in the presence of ammonia and an imination catalyst III) converting IPNI to IPDA in the presence of hydrogen and a hydrogenation catalyst.

17 . A process according to claim 16 , wherein in step III) is conducted in a single fixed bed reactor.

Assignees

• Basf Se

Inventors

• Krause Alfred
• Stavrou Marina-Eleni
• Schloderer Martin

Classifications

• C08G18/755 Primary

  and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate · CPC title

• C07C263/10

  by reaction of amines with carbonyl halides, e.g. with phosgene · CPC title

• C07C209/84

  Purification · CPC title

• C07C209/48

  by reduction of nitriles · CPC title

• C07C2601/14

  The ring being saturated · CPC title