IP Library Granted Patent US 12,606,667
Granted Patent B2
US 12,606,667 · App. 17/954,786 · Granted Apr 21, 2026

Process and system for production of polypropiolactone

Inventors: Jay J. Farmer (Rochester, NY); Peter Galebach (Rochester, NY); Kyle Sherry (Rochester, NY); Sadesh H. Sookraj (Rochester, NY)
Assignee: Novomer, Inc.
C08G63/08C08G63/823B01D3/14Y02P20/10
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Quick Facts
Patent No.
US 12,606,667
App. No.
17/954,786
Granted
Apr 21, 2026
Kind
B2
Abstract

Provided are integrated processes for the conversion of ethylene oxide to polypropiolactone. Systems for the production of polypropiolactone are also provided.

Claims (23)

1 . A system for converting ethylene oxide to polypropiolactone (PPL), comprising:

an ethylene oxide source;

a carbon monoxide source;

a carbonylation catalyst source;

a carbonylation solvent source;

a polymerization catalyst source;

a first reaction zone configured to receive ethylene oxide from the ethylene oxide source, carbon monoxide from the carbon monoxide source, carbonylation catalyst from the carbonylation catalyst source, and carbonylation solvent from the carbonylation solvent source, and to output a beta propiolactone (BPL) product stream from contacting the ethylene oxide and the carbon monoxide with the carbonylation catalyst in the presence of the carbonylation solvent in the first reaction zone, wherein the BPL product stream comprises carbonylation solvent and BPL;

a solvent removal unit configured to remove at least a portion of the carbonylation solvent from the BPL product stream; and

a second reaction zone configured to receive the BPL product stream from the solvent removal unit, and polymerization catalyst from the polymerization catalyst source, and to output a PPL product stream from contacting the BPL product stream with the polymerization catalyst in the second reaction zone, wherein the PPL product stream comprises PPL, wherein the polymerization catalyst is comprised of recycled polymerization catalyst.

2 . The system of claim 1 , further comprising a second solvent source, wherein the second solvent source is configured to output a polymerization solvent for combining with the BPL product stream, wherein the second solvent is different from the carbonylation solvent.

3 . The system of claim 2 , wherein the polymerization solvent is less polar than the carbonylation solvent as measured by dielectric constant.

4 . The system of claim 2 , wherein the polymerization solvent comprises a Lewis base and is less polar than 1,3-dioxane, ortho-difluorobenzene, or metadifluorobenzene.

5 . The system of claim 2 , wherein the polymerization solvent has a dielectric constant at 20° C. of less than about 13.6.

6 . The system of claim 1 , wherein the carbonylation solvent comprises a polar donating solvent.

7 . The system of claim 1 , wherein the polymerization catalyst is a salt of a compound of formula:

wherein p is from 0 to 9, and R a is a non-volatile moiety.

8 . The system of claim 1 , wherein the polymerization catalyst is a salt of a compound of formula:

wherein p is 0 to 9.

9 . The system of claim 1 , wherein the BPL product stream is neat when introduced into the second reaction zone.

10 . The system of claim 2 , wherein the polymerization catalyst along with the polymerization solvent is introduced to the BPL product stream.

11 . The system of claim 1 , further comprising a nanofiltration membrane configured to separate at least a portion of carbonylation catalyst from the BPL product stream.

12 . The system of claim 1 , wherein the second reaction zone is a reactive extruder.

13 . The system of claim 1 , wherein the carbonylation solvent has a boiling point below 160° C. at 1 atm.

Assignments (2)
CHANGE OF NAME Recorded Mar 24, 2026
From: NMER WINDDOWN, INC.
To: NOVOMER LLC
Reel/Frame 075187/0876 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 28, 2022
From: FARMER, JAY J.; GALEBACH, PETER; SHERRY, KYLE; SOOKRAJ, SADESH H.
To: NOVOMER, INC.
Reel/Frame 061568/0988 →
Continuity (4)
Division 16851517 · Apr 17, 2020
Division 15550234
Provisional Application 62116326 · Feb 13, 2015
Related Publication 20230085963A1 · Mar 23, 2023
References Cited (105)
US 3169945A · Hostettler · 1965 [cited by applicant]
US 3678069A · Busler · 1972 [cited by applicant]
US 5310948A · Drent et al. · 1994 [cited by applicant]
US 5359081A · Drent et al. · 1994 [cited by applicant]
US 5648452A · Schechtman et al. · 1997 [cited by applicant]
US 5705688A · Fauconet et al. · 1998 [cited by applicant]
US 6133402A · Coates et al. · 2000 [cited by applicant]
US 6316590B1 · Coates et al. · 2001 [cited by applicant]
US 6538101B2 · Coates et al. · 2003 [cited by applicant]
US 6541665B1 · Bastiaensen et al. · 2003 [cited by applicant]
US 6608170B1 · Coates · 2003 [cited by applicant]
US 7420064B2 · Luinstra et al. · 2008 [cited by applicant]
US 8445703B2 · Allen et al. · 2013 [cited by applicant]
US 8796475B2 · Allen et al. · 2014 [cited by applicant]
US 9096510B2 · Porcelli et al. · 2015 [cited by applicant]
US 9156803B2 · Allen et al. · 2015 [cited by applicant]
US 9206144B2 · Allen et al. · 2015 [cited by applicant]
US 9327280B2 · Lee et al. · 2016 [cited by applicant]
US 9403788B2 · Lee et al. · 2016 [cited by applicant]
US 9493391B2 · Allen et al. · 2016 [cited by applicant]
US 9914689B2 · Porcelli et al. · 2018 [cited by applicant]
US 10099988B2 · Farmer et al. · 2018 [cited by applicant]
US 10099989B2 · Sookraj · 2018 [cited by applicant]
US 10221150B2 · Farmer et al. · 2019 [cited by applicant]
US 10221278B2 · Lee et al. · 2019 [cited by applicant]
US 20120123137A1 · Allen et al. · 2012 [cited by applicant]
US 20130165670A1 · Allen et al. · 2013 [cited by applicant]
US 20130281715A1 · Allen et al. · 2013 [cited by applicant]
US 20140018570A1 · Pazicky et al. · 2014 [cited by applicant]
US 20140275575A1 · Allen et al. · 2014 [cited by applicant]
US 20140296522A1 · Lee et al. · 2014 [cited by applicant]
US 20140309399A1 · Porcelli et al. · 2014 [cited by applicant]
US 20150005513A1 · Lee et al. · 2015 [cited by applicant]
US 20150141693A1 · Allen et al. · 2015 [cited by applicant]
US 20150299083A1 · Porcelli et al. · 2015 [cited by applicant]
US 20150368394A1 · Allen · 2015 [cited by applicant]
US 20160016876A1 · Mahoney · 2016 [cited by applicant]
US 20160102040A1 · Allen et al. · 2016 [cited by applicant]
US 20160102068A1 · Allen et al. · 2016 [cited by applicant]
US 20160288057A1 · Lapointe et al. · 2016 [cited by applicant]
US 20170029352A1 · Sookraj et al. · 2017 [cited by applicant]
US 20170073463A1 · Lee et al. · 2017 [cited by applicant]
US 20170080409A1 · Farmer et al. · 2017 [cited by applicant]
US 20170096407A1 · Sookraj · 2017 [cited by applicant]
US 20170107103A1 · Sookraj et al. · 2017 [cited by applicant]
US 20170145126A1 · Mahoney · 2017 [cited by applicant]
US 20170225157A1 · Lee · 2017 [cited by applicant]
US 20170247309A1 · Porcelli et al. · 2017 [cited by applicant]
US 20180016219A1 · Farmer et al. · 2018 [cited by applicant]
US 20180022677A1 · Sookraj · 2018 [cited by applicant]
US 20180029005A1 · Sookraj · 2018 [cited by applicant]
US 20180030014A1 · Sookraj et al. · 2018 [cited by applicant]
US 20180030015A1 · Farmer et al. · 2018 [cited by applicant]
US 20180057619A1 · Sookraj · 2018 [cited by applicant]
US 20180094100A1 · Farmer et al. · 2018 [cited by applicant]
US 20180354881A1 · Farmer et al. · 2018 [cited by applicant]
US 20180354882A1 · Sookraj · 2018 [cited by applicant]
US 20190030520A1 · Lee · 2019 [cited by applicant]
JP 2015529644A · 2015 [cited by applicant]
WO 03050154A2 · 2003 [cited by applicant]
WO 2004089923A1 · 2004 [cited by applicant]
WO 2010118128A1 · 2010 [cited by applicant]
WO 2012030619A1 · 2012 [cited by applicant]
WO 2012158573A1 · 2012 [cited by applicant]
WO 2013063191A1 · 2013 [cited by applicant]
WO 2013122905A1 · 2013 [cited by applicant]
WO 2013126375A1 · 2013 [cited by applicant]
WO 2014004858A1 · 2014 [cited by applicant]
WO 2014008232A2 · 2014 [cited by applicant]
WO 2015085295A2 · 2015 [cited by applicant]
WO 2015138975A1 · 2015 [cited by applicant]
WO 2015171372A1 · 2015 [cited by applicant]
WO 2015184289A1 · 2015 [cited by applicant]
WO 2016015019A1 · 2016 [cited by applicant]
WO 2016130947A1 · 2016 [cited by applicant]
WO 2016130977A1 · 2016 [cited by applicant]
WO 2016130988A1 · 2016 [cited by applicant]
WO 2016130993A1 · 2016 [cited by applicant]
WO 2016130998A1 · 2016 [cited by applicant]
WO 2016131001A1 · 2016 [cited by applicant]
WO 2016131003A1 · 2016 [cited by applicant]
WO 2016131004A1 · 2016 [cited by applicant]
WO 2017023777A1 · 2017 [cited by applicant]
WO 2017023820A1 · 2017 [cited by applicant]
WO 2017165344A1 · 2017 [cited by applicant]
WO 2017165345A1 · 2017 [cited by applicant]
WO 2018085251A1 · 2018 [cited by applicant]
WO 2018085254A1 · 2018 [cited by applicant]
WO 2018136638A1 · 2018 [cited by applicant]
WO 2018170006A1 · 2018 [cited by applicant]
WO 2019051184A1 · 2019 [cited by applicant]
Kricheldorf et al Polylactones 33. The role of deprotonation in the anionic polymerization of beta-Propiolactone, Polymer vol. 37 No. 8, pp. 1405 1411, 1996, published on Oct. 1996. [cited by examiner]
Agostini et al., “Synthesis and Characterization of Poly-13-Hydroxybutyrate. I. Synthesis of Crystalline DL-Poly-13-Hydroxybutyrate from DL-13-Butyrolactone”, Journal of Polymer Science, Part A-1, vol. 9, 1971, pp. 2775… [cited by applicant]
Billingham et al., “Polymerization and Copolymerizationof 13-Butyrolactone by Aluminium Compounds”, Journal of Organometallic Chemistry, vol. 341, No. 1-3, 1988, pp. 83-89. [cited by applicant]
Church et al., “Carbonylation of Heterocycles by Homogeneous Catalysts”, Chemical Communication, 2007, pp. 657-674. [cited by applicant]
Extended European Search Report (includes Supplementary European Search Report and European Search Opinion) received for European Patent Application No. 16750024.8, mailed on Aug. 13, 2018, 7 pages. [cited by applicant]
Getzler et al., “Synthesis of 13-Lactones: A Highly Active and Selective Catalyst for Epoxide Carbonylation”, Journal of the American Chemical Society. vol. 124, No. 7, 2002, pp. 1174-1175. [cited by applicant]
Gross et al., “Polymerization of 13-Monosubstituted-13-Propiolactones using Trialkylaluminum-Water Catalytic Systems and Polymer Characterization”, Macromolecules, vol. 21, No. 9, 1988, pp. 2657-2668. [cited by applicant]
Hori et al., “Ring-Opening Polymerization of Optically Active 13-Butyrolactone using Distannoxane Catalysts: Synthesis of High-Molecular-Weight Poly (3-Hydroxybutyrate)”, Macromolecules, vol. 26, No. 20, 1993, pp. 5533-… [cited by applicant]
International Preliminary Report on Patentability received for PCT Patent Application No. PCTUS2016017878, mailed on Aug. 24, 2017, 7 pages. [cited by applicant]
International Search Report and Written Opinion received for PCT Patent Application No. PCTUS2016017878, mailed on May 2, 2016, 9 pages. [cited by applicant]
Rieth et al., “Single-Site Beta-Diiminate Zinc Catalysts for the Ring-Opening Polymerization of Beta-Butyrolactone and Beta-Valerolactone to Poly (3-Hydroxyalkanoates).”, Journal of the American Chemical Society, vol. 1… [cited by applicant]
Schechtman et al, “Chemical Synthesis of Isotactic Poly(3-Hydroxyalkanoates)”, Polymer Preprints, Division of Polymer Chemistry, Inc., vol. 40, No. 1, 1999, pp. 508-509. [cited by applicant]
Tanahashi et al., “Thermal Properties and Stereoregularity of Poly (3-Hydroxybutyrate) prepared from Optically Active 13-Butyrolactone with a Zinc-based Catalyst”, Macromolecules, vol. 24, No. 20, 1991, pp. 5732-5733. [cited by applicant]
Zhang et al., “Stereochemistry of the Ring-Opening Polymerization of (S)-13-Butyrolactone”, Macromolecules, vol. 23, No. 13, 1990, pp. 3206-3212. [cited by applicant]