IP Library Granted Patent US 8,106,242
Granted Patent B2
US 8,106,242 · App. 12/301,113 · Granted Jan 31, 2012

Process for the production of compounds via hazardous intermediates in a series of microreactors

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Quick Facts
Patent No.
US 8,106,242
App. No.
12/301,113
Granted
Jan 31, 2012
Kind
B2
Abstract

Multi-step process for the preparation of compounds via hazardous intermediates comprising the steps of a) preparing in a microreactor a hazardous intermediate and b) optionally performing one or more reaction steps on the hazardous intermediate in one or more additional microreactors and c) further converting the hazardous intermediate with a suitable reaction agent in a subsequent microreactor until a stable end product is formed.

Claims (26)

1. A multi-step process for the preparation of an amine compound via a hazardous organic azide intermediate, comprising the steps of:

a) reacting N 3 − in a continuous microreactor with an organic compound suitable for reaction with N 3 − to form a corresponding organic azide,

b) optionally performing one or more reaction steps on the organic azide in one or more additional microreactors, and

c) further reducing the organic azide with a suitable reducing agent in a subsequent continuous microreactor to form an amine compound.

2. A multi-step process for the preparation of an amine compound via a hazardous organic azide intermediate, comprising the steps of:

a) reacting N 3 − in a first continuous microreactor with an organic compound suitable for reacting with N 3 − to form a corresponding organic azide, and

b) directly further reducing the formed organic azide with a suitable reducing agent in a second continuous microreactor to form an amine compound.

3. A multi-step process for the preparation of alcohol, aldehyde or ketone compounds, optionally protected as the hydrate, hemiacetal or acetal, via hazardous organic peroxide or hydroperoxide intermediates, comprising the steps of:

a) reacting in a continuous microreactor an organic compound suitable for reacting with hydrogen peroxide, ozone or (singlet) oxygen, with hydrogen peroxide, ozone or (singlet) oxygen to form a corresponding hazardous organic peroxide or hydroperoxide intermediate,

b) optionally performing one or more reaction steps on the hazardous organic peroxide or hydroperoxide intermediate in one or more additional microreactors, and

c) further reducing the hazardous organic peroxide or hydroperoxide intermediate with a suitable reducing agent in a subsequent continuous microreactor to form a stable alcohol, or a stable aldehyde or ketone compound, optionally protected as the hydrate, hemiacetal or acetal.

4. A multi-step process for the preparation of alcohol, aldehyde or ketone compounds, optionally protected as the hydrate, hemiacetal or acetal, via hazardous organic peroxide or hydroperoxide intermediates, comprising the steps of:

a) reacting in a continuous microreactor an organic compound suitable for reacting with hydrogen peroxide, ozone or (singlet) oxygen, with hydrogen peroxide, ozone or (singlet) oxygen to form a corresponding hazardous organic peroxide or hydroperoxide intermediate, and

b) directly further reducing the hazardous organic peroxide or hydroperoxide intermediate with a suitable reducing agent in a second continuous microreactor to form a stable alcohol, or a stable aldehyde or ketone, optionally protected as the hydrate, hemiacetal or acetal.

5. The multi-step process according to claim 1 , wherein step c) is a hydrogenation step.

6. The multi-step process according to claim 2 , wherein step b) is a hydrogenation step.

7. The multi-step process according to claim 1 , wherein step a) and b) are performed in a continuous microreactor in a homogeneous solution or in a continuous liquid/liquid microreactor and wherein step c) is performed in a gas/liquid microreactor.

8. The multi-step process according to claim 2 , wherein step a) is performed in a continuous microreactor in a homogeneous solution or in a continuous liquid/liquid microreactor and wherein step b) is performed in a gas/liquid microreactor.

9. The multi-step process according to claim 3 , wherein step a) and b) are performed in a continuous microreactor in a homogeneous solution, in a continuous liquid/liquid microreactor or in a continuous gas/liquid microreactor and wherein step c) is performed in a gas/liquid microreactor.

10. The multi-step process according to claim 4 , wherein step a) is performed in a continuous microreactor in a homogeneous solution, in a continuous gas/liquid or in a continuous liquid/liquid microreactor and wherein step b) is performed in a gas/liquid microreactor.

11. The multi-step process according to claim 4 wherein step a) and step b) are performed in a gas/liquid microreactor.

12. The multi-step process according to claim 1 , wherein step c) is performed in a gas/liquid microreactor with an immobilized catalyst.

13. The multi-step process according to claim 2 , wherein step b) is performed in a gas/liquid microreactor with an immobilized catalyst.

14. The multi-step process according to claim 4 , wherein step a) comprises performing a reaction of naphthalene with ozone in a gas/liquid microreactor, and wherein step b) comprises reducing the hazardous peroxo intermediate to o-phthalic aldehyde in a second microreactor.

15. The multi-step process according to claim 14 , wherein step b) comprises performing the reduction of the hazardous peroxo intermediate by hydrogenation in a gas/liquid microreactor with an immobilized catalyst.

16. The multi-step process according to claim 3 , wherein the reaction of step a) is performed in a combustible solvent.

Assignments (5)
CHANGE OF NAME Recorded Sep 23, 2025
From: DPX HOLDINGS B.V.
To: PATHEON HOLDINGS I B.V.
Reel/Frame 072951/0839 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 1, 2014
From: DSM IP ASSETS B.V.
To: JLL/DELTA DUTCH NEWCO B.V.
Reel/Frame 034282/0574 →
CHANGE OF NAME Recorded Dec 1, 2014
From: JLL/DELTA DUTCH NEWCO B.V.
To: DPX HOLDINGS B.V.
Reel/Frame 034500/0795 →
CHANGE OF ADDRESS Recorded Dec 1, 2014
From: DPX HOLDINGS B.V.
To: DPX HOLDINGS B.V.
Reel/Frame 034500/0851 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 15, 2009
From: REINTJENS, RAFAEL WILHELMUS ELISABETH GHISLAIN; BROXTERMAN, QUIRINUS BERNARDUS; KOTTHAUS, MARTINA; POECHLAUER, PETER
To: DSM IP ASSETS B.V.
Reel/Frame 022962/0267 →