IP Library › Granted Patent US 12,503,412
Granted Patent B2
US 12,503,412 · App. 18/546,856 · Granted Dec 23, 2025

Recycling of styrene oligomers by de-polymerization process

Inventors: Norbert Niessner (Friedelsheim, DE); Bianca Wilhelmus (Hanau, DE); Achim Schmidt-Rodenkirchen (Bayreuth, DE); Konstantin Mierdel (Bayreuth, DE)
Assignee: INEOS STYROLUTION GROUP GMBH
C07C4/22
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,503,412
App. No.
18/546,856
Granted
Dec 23, 2025
Kind
B2
Abstract

A process for producing styrene monomers from styrene oligomers comprises the following steps: a) providing a composition (A) comprising at least one type of styrene oligomer, wherein the composition (A) comprises at least 15 wt.-% of styrene dimers and/or styrene trimers; b) providing a depolymerization reactor (R) with a reaction zone (Z); c) feeding the composition (A) into the reaction zone (Z) of the reactor (R); d) depolymerizing the at least one type of styrene oligomer in the reaction zone (Z) to obtain a composition (B), comprising styrene monomers; e) removing the composition (B) from the reaction zone (Z); and f) isolating the styrene monomers from the composition (B); wherein the temperature (T) inside the reaction zone (Z) is above 500° C. to below 800° C. and the average residence time (tA) of the composition (A) in the reaction zone (Z) is greater than 0.01 s and less than 60 s.

Claims (28)

1 . A process for producing styrene monomers from styrene oligomers comprising the following steps:

a) providing a composition (A) comprising at least one type of styrene oligomer, wherein the composition (A) comprises at least 15 wt.-%, based on the total weight of composition (A), of styrene dimers and/or styrene trimers;

b) providing a depolymerization reactor (R) with a reaction zone (Z);

c) feeding the composition (A) into the reaction zone (Z) of the reactor (R);

d) depolymerizing at least a portion of the at least one type of styrene oligomer in the reaction zone (Z) to obtain a composition (B), comprising styrene monomers;

e) removing the composition (B) from the reaction zone (Z); and

f) isolating at least a portion of the styrene monomers from the composition (B);

wherein the temperature (T) inside the reaction zone (Z) of the reactor is set to a value of greater than 500° C. to a value of less than or equal to 670° C.; and

wherein the average residence time (tA) of the composition (A) in the reaction zone (Z) of the reactor is set to a value greater than 0.01 s but less than 60 s.

2 . The process of claim 1 , wherein the average residence time (tA) of the composition (A) in the reaction zone (Z) is set to a value of less than 30 s.

3 . The process of claim 1 , wherein the composition (A) comprises at least 10 wt.-%, based on the total weight of composition (A), of styrene dimers, and at least 5 wt.-%, based on the total weight of composition (A), of styrene trimers.

4 . The process of claim 1 , wherein the composition (A) is obtained as a byproduct of a process for producing styrene monomers from at least one type of styrene polymer or co-polymer (P).

5 . The process of claim 1 , wherein the composition (A) is fed into the reaction zone (Z) of the reactor (R) in the absence of polymers or co-polymers.

6 . The process of claim 1 , wherein the composition (A) is fed into the reaction zone (Z) of the reactor (R) together with at least one styrene polymer or styrene co-polymer.

7 . The process of claim 6 , wherein the at least one type of styrene polymer or styrene co-polymer (P) is not densified.

8 . The process of claim 4 , wherein the process for producing styrene monomers from at least one type of styrene polymer or styrene co-polymer (P) takes place in the reaction zone (Z) of the depolymerization reactor (R) at the temperature (T) and an average residence time (tP) of the styrene polymer or styrene co-polymer (P) in the reaction zone (Z) set to a value greater than 0.01 s but less than 60 s, and the composition (A) is re-fed into the reaction zone (Z) alongside the at least one type of styrene polymer or styrene co-polymer (P).

9 . The process of claim 8 , wherein the styrene polymer or styrene copolymer is not densified.

10 . The process of claim 1 , wherein the temperature (T) is set to a value of 550° C. to 670° C.

11 . The process of claim 1 , wherein the temperature (T) is set to a value of 595° C. to 605° C.

12 . The process of claim 1 , wherein the process takes place under a nitrogen atmosphere.

13 . The process of claim 1 , wherein the average residence time (tA) is controlled by a stream of nitrogen.

14 . The process of claim 1 , wherein the depolymerization reactor (R) is a fluidized bed reactor.

15 . The process of claim 14 , wherein the fluidized bed reactor contains silicon carbide (SiC) particles.

16 . The process of claim 1 , wherein step f) comprises condensation and/or distillation of at least a portion of composition (B).

17 . The process of claim 1 , wherein the composition (A) comprises at least 40 wt.-%, based on the total weight of composition (A), of styrene dimers and styrene trimers.

18 . The process of claim 1 , wherein the maximum degree of polymerization of any of the styrene oligomers in composition (A) does not exceed 20 styrene repeating units.

19 . The process of claim 1 , wherein the maximum degree of polymerization of any of the styrene oligomers in composition (A) does not exceed 5 styrene repeating units.

20 . The process of claim 1 , wherein the styrene monomers comprise less than 0.01 wt.-% of styrene dimers and/or styrene trimers.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 31, 2023
From: NIESSNER, NORBERT, DR.; WILHELMUS, BIANCA, DR.; SCHMIDT-RODENKIRCHEN, ACHIM; MIERDEL, KONSTANTIN
To: INEOS STYROLUTION GROUP GMBH
Reel/Frame 064765/0046 →
Priority Claims (1)
EP 21159259 · Feb 25, 2021 · regional
Continuity (1)
Related Publication 20240140884A1 · May 2, 2024
References Cited (13)
US 5055167A · Dummersdorf et al. · 1991 [cited by applicant]
US 5672794A · Northemann · 1997 [cited by applicant]
US 10301235B1 · Cavinaw et al. · 2019 [cited by applicant]
EP 1966291A1 · 2008 [cited by applicant]
GB 1369964A · 1974 [cited by applicant]
JP 2003267896A · 2003 [cited by examiner]
WO 2007063462A1 · 2007 [cited by applicant]
Kamiyama, JP 2003-267896 A, English translation. [cited by examiner]
G. Grause et al., Feedstock recycling of waste polymeric material, in: Journal of Material Cycles and Waste Management, 13(4), 2011, 265-282. [cited by applicant]
C. Bouster et al., Study of the pyrolysis of polystyrenes: Kinetics of thermal decomposition, Journal of Analytical and Applied Pyrolysis, 1 (1980) 297-313. [cited by applicant]
C. Bouster et al., Evolution of the product yield with temperature and molecular weight in the pyrolysis of polystyrene, in: Journal of Analytical and Applied Pyrolysis 15 (1989) 249-259. [cited by applicant]
D. S. Achilias et al. (Chemical recycling of polystyrene by pyrolysis: Potential use of the liquid product for the reproduction of polymer, in: Macromolecular Materials and Engineering, 292(8) (2007) 923-934. [cited by applicant]
D. Baskaran, Anionic Vinyl Polymerization, Controlled and Living Polymerizations: From Mechanisms to Applications, John Wiley & Sons, 2009, 1-56. [cited by applicant]