Method for the manufacture of a polyhydroxy-carboxylic acid

Patent metadata

Field	Value
Publication number	US-9637587-B2
Application number	US-201113985770-A
Country	US
Kind code	B2
Filing date	Nov 15, 2011
Priority date	Feb 18, 2011
Publication date	May 2, 2017
Grant date	May 2, 2017

Abstract

Disclosed is a method to prepare a polylactic acid comprising the steps of performing a ring opening polymerization using a catalyst and either a catalyst killer compound or an endcapping additive to obtain a raw polylactic acid of MW greater than 10,000 g/mol, purifying the raw polylactic acid by removing and separating low boiling compounds comprising lactide and impurities from the raw polylactic acid by devolatization of the low boiling compounds as a gas phase stream, and purifying the lactide from the devolatization and removing the impurities from the gas phase stream of evaporated low boiling compounds by means of crystallization by desublimation from the gas phase, wherein the lactide is purified and the removed impurities include a catalyst residue and a compound containing at least one hydroxyl group such that the purified lactide is then polymerized by feeding it back into the ring opening polymerization. The invention further relates to an apparatus for carrying out the method comprising a polymerization reactor for performing a ring opening polymerization to obtain a raw polylactic acid, a devolatization apparatus for separating low boiling compounds comprising lactide and impurities from a raw polylactic acid, and a crystallization apparatus for purifying a lactide and removing impurities by means of a desublimation and a crystallization in the same crystallization apparatus.

First claim

What is claimed is:

1. An apparatus for preparing polylactic acid, comprising:
a polymerization reactor adapted for performing a ring opening polymerization to obtain a raw polylactic acid having a Mw of at least 20,000 g/mol,
a devolatization apparatus adapted for separating low boiling compounds comprising lactide and impurities from the raw polylactic acid having a Mw of at least 20,000 g/mol,
a crystallization apparatus for purifying lactide from the low boiling compounds separated in the devolatization apparatus and removing impurities by means of a desublimation and a crystallization in the same crystallization apparatus, and
a recycle line connecting the crystallization apparatus and the polymerization reactor for recycling purified lactide from the crystallization apparatus back into the polymerization reactor
wherein:
lactide and a raw polylactic acid having a Mw of at least 20,000 g/mol are present in the polymerization reactor,
a ring opening polymerization reaction of lactide to form polylactic acid having a Mw of at least 20,000 g/mol is occurring within the polymerization reactor, and
purified lactide from the crystallization apparatus is present in the recycle line.

2. A method to prepare a polylactic acid comprising providing the apparatus of claim 1 and further comprising the steps of:
(i) performing a ring opening polymerization in the polymerization reactor using a catalyst and either a catalyst killer compound or an endcapping additive to obtain a raw polylactic acid of MW greater than 20,000 g/mol,
(ii) purifying the raw polylactic acid in the devolatization apparatus by removing and separating low boiling compounds comprising lactide and impurities from the raw polylactic acid by devolatization of the low boiling compounds as a gas phase stream,
(iii) purifying the lactide from the devolatization and removing the impurities from the gas phase stream of evaporated low boiling compounds in the crystallization apparatus by means of crystallization by desublimation from the gas phase,
wherein the lactide is purified and the removed impurities include a catalyst residue and a compound containing at least one hydroxyl group such that the purified lactide is then polymerized by feeding it back into the ring opening polymerization through the recycle line.

3. The method of claim 2 , wherein the desublimation occurs on a cooled surface.

4. The method of claim 2 , wherein an apparatus for the crystallization and an apparatus for the devolatization operate substantially under a same vacuum condition.

5. The method of claim 2 , wherein the desublimation and the crystallization occur in a same apparatus.

6. The method of claim 4 , wherein the apparatus for the crystallization has no inert gas stream.

7. The method of claim 2 , wherein the evaporated gas phase stream from the devolatization contains at least 30% of lactide, preferably at least 60%, most preferred at least 90%.

8. The method of claim 2 , wherein the lactide is first subjected to a sweating step, followed by a melting step, prior to feeding it back into the ring opening polymerization.

9. The method of claim 2 , wherein the devolatization operates under a lactide partial pressure of less than 20 mbar, preferably less than 10 mbar, particularly preferred less than 5 mbar.

10. The method of claim 2 , wherein the removed impurities include either an organometallic compound or a carboxylic acid.

11. The method of claim 2 , wherein at least a portion of a purge stream from the crystallization is recycled to a raw lactide purification step, a pre-polymerization and dimerization step, or a solvent removal step in the production of a purified lactide.

12. The method of claim 8 , wherein a liquid from the sweating step is collected and recrystallized in order to recover the lactide.

13. The apparatus of claim 1 , wherein no throttling means or vacuum pumps are arranged between the crystallization apparatus and the devolatization apparatus.

14. The apparatus of claim 1 , wherein a heat exchanger is arranged between the devolatization apparatus and the crystallization apparatus.

15. The apparatus of claim 1 , wherein the crystallization apparatus has heat exchanging surfaces for the solidification of a gaseous stream.

Assignees

• Stepanski Manfred
• Loviat Francois
• Kuszlik Andrzej
• Sulzer Chemtech Ag

Inventors

• Stepanski Manfred
• Loviat Francois
• Kuszlik Andrzej

Classifications

• C08G63/90

  Purification; Drying · CPC title

• C08F124/00

  Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a heterocyclic ring containing oxygen (cyclic esters of polyfunctional acids C08F118/00; cyclic anhydrides of unsaturated acids C08F120/00, C08F122/00) · CPC title

• C08G63/08 Primary

  Lactones or lactides · CPC title

• C08G63/78

  Preparation processes · CPC title

• C07D319/12

  not condensed with other rings · CPC title