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(12) Patent Application Publication (10) Pub. No.: US 2004/0122240 A1 Yamane Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2004/0122240 A1 Yamane Et Al US 2004.0122240A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2004/0122240 A1 Yamane et al. (43) Pub. Date: Jun. 24, 2004 (54) GLYCOLIDE PRODUCTION PROCESS, AND (52) U.S. Cl. .............................................................. 549/274 GLYCOLIC ACID OLIGOMER FOR GLYCOLDE PRODUCTION (57) ABSTRACT (76) Inventors: Kazuyuki Yamane, Fukushima (JP); Yukichika Kawakami, Fukushima (JP) The invention relates to a glycolide production process Correspondence Address: wherein a depolymerization reaction System comprising a DINSMORE & SHOHL, LLP glycolic acid oligomer or a glycolic acid oligomer and a 1900 CHEMED CENTER polar organic Solvent is heated to depolymerize the glycolic 255 EAST FIFTH STREET acid oligomer into glycolide, the resulting glycolide or the CINCINNATI, OH 45202 (US) glycolide and polar organic Solvent are distilled out of the depolymerization reaction System, and the glycolide is (21) Appl. No.: 10/472,719 recovered from distillates obtained by distillation. The gly colic acid oligomer or the glycolic acid oligomer and polar (22) PCT Filed: Apr. 10, 2002 organic Solvent are continuously or intermittently charged into the depolymerization reaction System, thereby carrying (86) PCT No.: PCT/JP02/03570 out depolymerization reactions continuously or repeatedly. (30) Foreign Application Priority Data During the depolymerization reactions, a compound having an alcoholic hydroxyl group is permitted to exist at a specific Apr. 12, 2001 (JP)...................................... 2001-113577 quantitative ratio in the depolymerization reaction System. The invention is also concerned with a glycolic acid oligo Publication Classification mer for the production of glycolide, which is obtained by condensation of glycolic acid in the presence of the com (51) Int. Cl." ............................................. C07D 323/04 pound having an alcoholic hydroxyl group. US 2004/O122240 A1 Jun. 24, 2004 GLYCOLIDE PRODUCTION PROCESS, AND 0007 To produce polyglycolic acid (also called “polyg GLYCOLIC ACID OLIGOMER FOR GLYCOLIDE lycolide') having a high molecular weight by the ring PRODUCTION opening polymerization of glycolide, it is required to use high-purity polyglycolide as the Starting material. To use TECHNICAL FIELD glycolide as the Starting material to produce polyglycolic 0001. The present invention relates generally to a process acid on an industrial Scale, it is thus essential to economi for the production of glycolide that is a cyclic dimer ester of cally feed Such high-purity glycolide. glycolic acid, and more particularly to a glycolide produc 0008 Glycolide is a cyclic ester compound having the tion process by depolymerization by heating of glycolic acid Structure wherein two water molecules are eliminated from oligomers, which ensures the long-term Stability of a depo two glyclolic acid molecules. Only by the esterification lymerization reaction System comprising a glycolic acid reaction of glycolic acid, however, any glycolide cannot be oligomer, So that the depolymerization reaction can be obtained because of the formation of glycolic acid oligo performed in a stable yet efficient manner even when the mers. So far, various glycolide production processes have depolymerization reaction is carried out continuously or been proposed. repeatedly. 0009 U.S. Pat. No. 2,668,162 discloses a process in 0002 The present invention is also concerned with a which a glycolic acid oligomer is crushed into powders and novel glycolic acid oligomer, which can reduce or Substan heated at 270 to 285 C. under an ultra-high vacuum (12 to tially eliminate adverse influences ascribable to impurities 15 Torr (1.6 to 2.0 kPa)) while the powders are fed to a contained in glycolic acid that is the raw material for reaction vessel in Small portions (about 20 g/hour) for glycolic acid oligomers, So that the depolymerization reac depolymerization, and the resultant glycolide-containing tion can be carried out in a stable yet efficient fashion even Vapor is entrapped. This process, albeit being Suitable for when the depolymerization reaction is conducted continu Small-scale production, is found to have difficulty in large ously or repeatedly over an extended period of time. Scale production and So unsuitable for mass production. In addition, this proceSS causes the oligomer to become heavy BACKGROUND ART upon heating and So remain in the form of much residues in the reaction vessel, resulting in decreased glycolide yields 0.003 Polyglycolic acid is a polyester formed by dehy and the need of cleaning off the residues. To add to this, the dration-polycondensation of glycolic acid (i.e., C.-hydroxy process makes glycolide (having a melting point of 82 to 83 lacetic acid) and having the following formula: C.) and byproducts likely to separate out in recovery lines, ending up with troubles Such as line clogging. O O 0010 U.S. Pat. No. 4,727,163 shows a glycolide produc tion proceSS wherein a polyether having good thermal Sta in HC o v Hedehydration HC-C-O bility is used as a Substrate, a Small amount of glycolic acid OH OH is then block copolymerized with the substrate to obtain a block copolymer, and the block copolymer is finally heated for depolymerization. However, this block copolymerization 0004 Polyglycolic acid is a biodegradable polymer that process is intractable and incurs Some considerable produc is hydrolyzed in Vivo and, in natural environments, is tion cost. In addition, the proceSS makes glycolide and metabolized and decomposed by microorganisms into water byproducts likely to Separate out in recovery lines, leading and carbonic acid gas. For this reason, the polyglycolic acid to troubles Such as line clogging. now attracts attention as environment-friendly polymer Sub 0.011 U.S. Pat. Nos. 4,835,293 and 5,023,349 teach a Stitutes for medical materials or general-purpose. However, process wherein an O-hydroxycarboxylic acid oligomer Such it is still difficult to obtain any polyglycolic acid having a as a polyglycolic acid oligomer is heated into a melt, and a high molecular weight by means of the dehydration-poly cyclic dimer esterS Such as glycolide generated and vapor condensation of glycolic acid. ized out of the Surface of the melt is entrained in an inert gas 0005 According to another polyglycolic acid production Such as nitrogen gas and Stripped in a low-boiling Solvent proceSS So far known in the art, glycolide of the following such as acetone or ethyl acetate for recovery. With this formula, which is a cyclic dimer ester of glycolic acid is first process, it is still difficult to cut back on production costs, Synthesized. because of problems Such as a slow formation rate of the cyclic dimer ester, possible formation of heavy materials in the melt, and the need for preheating for blowing a large H H O amount of inert gas into the melt. 0012 French Patent No. 2692263-A1 discloses a process for the production of a cyclic dimer ester wherein an O O oligomer of an O-hydroxycarboxylic acid or its ester or Salt is added to a Solvent with a catalyst added thereto, and then O H. H. Stirred in the presence of heat for catalytic decomposition. This process is carried out under normal or applied pressure, using a Solvent Suitable for entraining the cyclic dimer ester 0006 Then, this glycolide is subjected to ring-opening therein in a gaseous phase State. The gaseous phase is then polymerization in the presence of a catalyst Such as Stannous condensed for the recovery of the cyclic dimer ester and Octoate. Solvent. The Specification refers to only an example wherein US 2004/O122240 A1 Jun. 24, 2004 a lactic acid oligomer is used as the raw feed and dodecane colic acid, organic acids Such as diglycolic acid and methoxy (having a boiling point of about 214 C.) is employed as the acetic acid. Although depending on how to produce glycolic solvent. However, the results of follow-up experimentation acid, oxalic acid may also be detected. made by the inventors under the same conditions as 0019. When the depolymerization reaction is carried out described in the example and using a glycolic acid oligomer continuously or repeatedly while this System IS replenished and dodecane showed that heavy materials begin to form with a fresh glycolic acid oligomer and a fresh polar organic Simultaneously with the Start of the depolymerization reac Solvent, these organic acids are built up in the depolymer tion, the formation of glycolide Stops at a point of time when ization reaction System because of their relatively high a very slight amount of glycolide is formed, and much labor boiling points. The accumulation of the organic acids within is needed for cleaning reaction residues because they are too the depolymerization reaction System has now been found to Viscous. have adverse influences on the depolymerization reaction. 0013 JP-A 09-328481 filed by the applicant of this 0020. The instability of the depolymerization reaction application discloses a process comprising the Steps of System and the decreased formation rate of glycolide due to heating and depolymerizing an O-hydroxycarboxylic acid Such organic acid impurities may possibly be prevented by oligomer Such as a glycolic acid oligomer in a polar organic using an aqueous Solution of high-purity glycolic acid or Solvent having a high boiling point, and distilling out the purifying an industrial-grade acqueous Solution of glycolic resultant cyclic dimer ester Such as glycolide together with acid thereby reducing the organic acid impurity content the polar organic Solvent, and removing the cyclic dimer thereof. However, the glycolic acid purification Step costs ester from the distillates. much, and So goes against glycolide production cost reduc 0.014. The results of the inventors subsequent investiga tions and eventually provides an obstacle to versatile appli tion have showed that if a polyalkylene glycol ether having cations of polyglycolic acid. Satisfactory thermal Stability is used as the polar organic 0021. In addition, even with a glycolic acid oligomer Solvent in this process, cost reductions can then be achieved Synthesized using an aqueous Solution of high-purity gly by recycling the Solvent.
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