Lactide production from dehydration of aqueous lactic acid feed

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

549379, C07D31912, C07D31900

Patent

active

052741273

ABSTRACT:
The present invention is directed to a method for making L-lactide from aqueous L-lactic acid. Aqueous lactic acid feed for present purposes comprehends an aqueous mixture of one or more of L.sub.1 A, L.sub.2 A, and L.sub.3 A, optionally with LD being present. L-lactic acid is the preferred feed configuration for making L-lactide, and is to be understood even though the configuration symbol is not used throughout this application. Aqueous lactic acid feed is treated for removal of water therefrom until a degree of polymerization (DP) not substantially above about 2 is reached. The treatment then is ceased to produce a crude LD product. LD then is separated from the crude LD product. A preferred treatment involves heating the feed at elevated temperature to remove water. LD can be separated from the crude LD product by a variety of techniques to produce an LD-depleted product. This LD-depleted product, optionally augmented with additional aqueous lactic acid and/or water then can be readmitted to the process for making additional lactide. This cyclic or recycle process embodiment of the present invention enables very high lactide conversions to be realized.

REFERENCES:
patent: 1095205 (1914-05-01), Gruter et al.
patent: 1594843 (1926-08-01), Lawrie
patent: 1995970 (1935-03-01), Dorough
patent: 2163268 (1939-06-01), Carothers et al.
patent: 2174491 (1939-09-01), Watson
patent: 2189572 (1940-02-01), Watson
patent: 2668162 (1954-02-01), Lowe
patent: 2703316 (1955-03-01), Schneider
patent: 2758987 (1956-08-01), Salzberg
patent: 2768973 (1956-10-01), Castle et al.
patent: 3322719 (1967-05-01), Peilstocker
patent: 3435008 (1969-03-01), Schmitt et al.
patent: 3457280 (1969-07-01), Schmitt et al.
patent: 3597450 (1971-08-01), Schmitt et al.
patent: 3736646 (1973-06-01), Schmitt et al.
patent: 3867190 (1975-02-01), Schmitt et al.
patent: 3960152 (1976-06-01), Augurt et al.
patent: 4033938 (1977-07-01), Augurt et al.
patent: 4797468 (1989-01-01), DeVries
patent: 4835293 (1989-05-01), Bhatia
patent: 4990222 (1991-02-01), Aigner et al.
patent: 5023349 (1991-06-01), Bhatia
patent: 5023350 (1991-06-01), Bhatia
patent: 5043458 (1991-08-01), Bhatia
patent: 5053485 (1991-10-01), Nieuwenhuis et al.
patent: 5053522 (1991-10-01), Muller
patent: 5068418 (1991-11-01), Kulprathipanja et al.
patent: 5075115 (1991-12-01), Brine
patent: 5089632 (1992-02-01), Paul
patent: 5091544 (1992-02-01), Bhatia
Bezzi, "The Constitution of Some Polyglycolides", pp. 219-233, 1949, Gazz Chim. Ital. vol. 79.
Bezzi, "Transformation of Cyclic Esters Into Linear Polyesters", pp. 215-224, 1938; Gazz. Chim. Ital. vol. 68.
Bezzi et al., "Dehydration Products of Lactic Acid Typifying the Transformation of Cyclic Esters into Linear Polyesters", 1936, Meeting of the Italian Academy of Science, Nov.
Bischoff et al., "Ueber Das Glycolid und Seine Homologen", pp. 262-265, 1893; Chem. Ber., vol. 26.
Carothers et al., "Studies of Polymerization and Ring Formation. X. The Reversible Polymerization of Six-Membered Cyclic Esters", pp. 761-771, (1932), J. Am. Chem. Soc., vol. 54.
Carothers, "Polymers and Polyfunctionality", pp. 39-53 (1936), Transactions of The Faraday Society, vol. 32.
Dietzel et al., "Uber Das Chemische Gleichgewicht Zwischen Der Milchsaure und Ihren Anhydriden in Wassriger Losung", pp. 1307-1314, (1925), Chem. Ber., vol. 58B.
Deibig et al., "I. Synthesis and Properties of Polytetramethyl Glycolide", pp. 123-131, (1971), Die Makromolekulare Chemie, vol. 145.
Deibig et al., "II. Thermal Behavior of Polytetramethyl Glycolide", pp. 133-139, (1971), Die Makromolekulare Chemie, vol. 145.
Filachione et al., "Lactic Acid Condensation Polymers: Preparation By Batch and Continuous Methods", pp. 223-228, (1944), Industrial and Engineering Chemistry, Mar., vol. 36, No. 3.
Hill et al., "Cyclic and Polymeric Formals", pp. 925-928, (1935), J. Am. Chem. Soc., vol. 57.
Holten, "Lactic Acid; Properties and Chemistry of Lactic Acid and Derivatives", pp. 221-231, (1971), Verlag Chemie.
Imasaka et al., "Synthesis of Degradable Terpolymers Responding to External Stimuli Such as Ph, Ionic Strength, and Temperature", pp. 715-722, (1991), Makromol. Chem. vol. 192.
Ikada et al., "Stereocomplex Formation Between Enantiomeric Poly(Lactides)", pp. 904-906, (1987), American Chemical Society, Macromolecules, 20.
Jackanicz et al., "Polylactic Acid as a Biodegradable Carrier for Contraceptive Steroids", pp. 227-234, (1973), The Population Counsel, Sep., vol. 8, No. 3.
Jungfleisch et al., "Organic Chemistry--of Lactyllactyllactic Acid and the Dilactide of Racemic Lactic Acid", pp. 502-505, (1905), Academie Des Sciences, Meeting of Feb. 20.
Jungfleisch et al., "Organic Chemistry--on The Dilactide of the Right", pp. 111-113, (1905) Academie Des Sciences, Meeting of Jul. 10.
Jungfleisch et al., "Organic Chemistry--on the Dilactide of Left Lactic Acid", pp. 637-639, (1906), Academie Des Sciences, Meeting of Mar. 12.
Jungfleisch et al., "Organic Chemistry--on Ethyl Lactyllactate", (1907), Academie Des Sciences, Meeting of Feb. 25.
Jungfleisch et al., "Organic Chemistry--on Inactive Dilactylic Acid", p. 979, (1907), Academie Des Sciences, Meeting of May 6.
Kleine et al., "High Molecular Weight, Especially Optically Active Polyesters of Lactic Acid: An Investigation of the Stereochemistry of Macromolecular Compounds", pp. 1-21, (1958), Report from the Research laboratory for Macromolecular Chemistry, Dec.
Kulkarni et al., "Polylactic Acid for Surgical Implants", pp. 839-843, (1966), Arch. Surg., vol. 93, Nov.
Light, "Lactic Acid Resins", pp. 135-136, (1940), Paint Manufacture, Jun.
Montgomery, "Acidic Constituents of Lactic Acid-Water Systems", pp. 1466-1468, (1952), J. Am. Chem. Soc., vol. 74.
Watson, "Composition of Lactic Acid, Production of a Highly Concentrated Acid", pp. 399-401, (1940), Industrial and Engineering Chemistry, vol. 32, No. 3.
Wise, "Biopolymeric Controlled Release Systems", pp. 3-28, (1984), CRC Press, vol. 1.
Wise, "Biopolymeric Controlled Release Systems", pp. 187-199, (1984), CRC Press, vol. 2.
Wise, et al., "Lactic/Glycolic Acid Polymers", pp. 237-270, Dynatech R/D Company, Cambridge, Mass., U.S.A. (1984).
Wislicenus, "On the Optically Active Lactic Acid of Sarcolactic Liquid, the Paralactic Acid", pp. 318-319, (1873), Liebigs Ann. Chem. vol. 167.

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Lactide production from dehydration of aqueous lactic acid feed does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Lactide production from dehydration of aqueous lactic acid feed, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Lactide production from dehydration of aqueous lactic acid feed will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-1544203

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.