IP Library Granted Patent US 10,450,254
Granted Patent B2
US 10,450,254 · App. 16/327,041 · Granted Oct 22, 2019

Method for the combined production of polyols in the presence of an inorganic base

Inventors: Guido D. Frey (Mülheim, DE); Melanie Bothe (Düsseldorf, DE); Heinz Strutz (Moers, DE); William E. Slinkard (Richmond, TX)
Assignee: OXEA GMBH
C07C29/38C07C31/20C07C31/22
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Quick Facts
Patent No.
US 10,450,254
App. No.
16/327,041
Granted
Oct 22, 2019
Kind
B2
Abstract

The present invention relates to a process for simultaneously consecutive preparation of polyols by base-catalyzed reaction of at least two different mid-chain aldehydes with formaldehyde. The simultaneous consecutive mode of operation makes it possible to achieve high conversions and high selectivities for both aldehydes, with additional achievement of a distinct reduction in the amount of unreacted formaldehyde remaining. This leads to improved process economics, since the energy costs for workup of the formaldehyde stream are distinctly reduced.

Claims (20)

1. A process for simultaneously consecutive preparation of at least two different polyols by reaction of aliphatic aldehydes with formaldehyde in the presence of an inorganic base, characterized in that, in a 1st process step, an aliphatic C2-C9 aldehyde is reacted with formaldehyde in the presence of an inorganic base and, without workup of the reaction solution, in a 2nd process step, the reaction solution from the 1st process step is converted further with addition of at least one aliphatic C2-C9 aldehyde other than the aldehyde from the 1st process step.

2. The process according to claim 1 , wherein, in the 1st process step, an aliphatic C2-C9 aldehyde unbranched in the 2 position is reacted, and, in the 2nd process step, an aliphatic C2-C9 aldehyde branched in the 2 position.

3. The process according to claim 1 , wherein the aldehyde used in the 1st process step is selected from the group consisting of n-propanal, n-butanal, valeraldehyde, and the aldehyde used in the 2nd process step is i-butanal.

4. The process according to claim 1 , wherein the 1st and 2nd process step are conducted at a temperature of greater than or equal 10° C. and less than or equal 105° C.

5. The process according to claim 1 , wherein, in the 2nd process step, an inorganic base is additionally added to the reaction solution.

6. The process according to claim 5 , wherein the same inorganic base is used in the 1st and 2nd process step.

7. The process according to claim 1 , wherein the inorganic base is selected from the group consisting of NaOH, KOH, Ca(OH) 2 or mixtures thereof.

8. The process according to claim 1 , wherein the molar ratio of inorganic base to aliphatic aldehyde in the two process steps is greater than or equal 1:1 and less than or equal 1.6:1.

9. The process according to claim 1 , wherein the formaldehyde is added in the 1st process step in the form of an aqueous formaldehyde solution having a formaldehyde content of greater than or equal 5% by weight and less than or equal 50% by weight.

10. The process according to claim 1 , wherein the molar ratio of formaldehyde to aliphatic aldehyde in the first process step is greater than or equal 3.1:1 and less than or equal 12:1 and the molar ratio of formaldehyde to aliphatic aldehyde in the 2nd process step is greater than or equal 2.1:1 and less than or equal 7:1.

11. The process according to claim 1 , wherein formaldehyde is added only in the 1st process step.

12. The process according to claim 1 , wherein the addition of at least one reactant in the 1st and/or in the 2nd process step is effected stepwise.

13. The process according to claim 12 , wherein the aliphatic aldehyde in the 1st process step is added stepwise to the reaction mixture.

14. The process according to claim 1 , wherein the conversion of aldehyde in the reaction mixture at the end of the 1st process step is greater than or equal 50%.

15. The process according to claim 1 , wherein the reactant volume throughput per unit reactor volume and time (V/Vh) in the two process steps is greater than or equal 0.3 and less than or equal 4.0.

16. The process according to claim 2 , wherein an inorganic base is additionally added to the reaction solution in the 2nd process step.

17. The process according to claim 2 , wherein the molar ratio of inorganic base to aliphatic aldehyde in the two process steps is greater than or equal 1:1 and less than or equal 1.6:1.

18. The process according to claim 2 , wherein formaldehyde is added only in the 1st process step.

19. The process according to claim 2 , wherein the aliphatic aldehyde in the 1st process step is added stepwise to the reaction mixture.

20. The process according to claim 1 , wherein formaldehyde is added only in the 1st process step; the aliphatic aldehyde in the 1st process step is selected from the group consisting of n-propanal, n-butanal, and valeraldehyde and is added stepwise to the reaction mixture; the aliphatic aldehyde in the 2 nd process step is i-butanal; an inorganic base is additionally added to the reaction solution in the 2nd process step; the molar ratio of inorganic base to aliphatic aldehyde in the two process steps is greater than or equal 1:1 and less than or equal 1.6:1; and the reactant volume throughput per unit reactor volume and time (V/Vh) in the two process steps is greater than or equal 0.3 and less than or equal 4.0.

Assignments (2)
CHANGE OF NAME Recorded Aug 25, 2021
From: OXEA GMBH
To: OQ CHEMICALS GMBH
Reel/Frame 057312/0979 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 22, 2019
From: FREY, GUIDO D; BOTHE, MELANIE; STRUTZ, HEINZ; SLINKARD, WILLIAM E
To: OXEA GMBH
Reel/Frame 048404/0489 →
Priority Claims (1)
EP 16198007 · Nov 9, 2016 · regional
Continuity (2)
Provisional Application 62412306 · Oct 25, 2016
Related Publication 20190241492A1 · Aug 8, 2019