Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1993-09-29
1995-05-30
Ivy, C. Warren
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
549379, C07D31900, C07D31912
Patent
active
054203040
ABSTRACT:
Disclosed is a novel integrated process for production of cyclic esters which includes recovery of starting materials, such as lactic acid from a dilute aqueous lactic acid-containing solution, by solvent extraction. The starting materials are then formed into cyclic esters by removal of water wherein the concentration of higher molecular weight oligomers is maintained below about 20 wt % of the reaction composition. The process further includes providing a recovery solvent for the reaction composition and separating the cyclic esters from the starting materials and higher molecular weight oligomers by liquid-liquid equilibrium separation. The present invention is further directed toward independent novel unit operations of the overall process. The present invention provides for the efficient production and recovery of cyclic esters due to integration of the various unit operations by use of appropriate solvents and recycle streams. In addition, high rates of conversion of starting materials and high rates of selective production of cyclic esters are achieved by appropriate control of process parameters.
REFERENCES:
patent: 1095205 (1914-05-01), Gruter et al.
patent: 1594843 (1926-08-01), Lawrie
patent: 1906068 (1933-04-01), Jenemann
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: 4070375 (1978-01-01), Suzuki
patent: 4435595 (1984-03-01), Agreda et al.
patent: 4727163 (1988-02-01), Bellis
patent: 4730082 (1988-03-01), Amiet
patent: 4771001 (1988-09-01), Bailey et al.
patent: 4797468 (1989-01-01), De Vries
patent: 4835293 (1989-05-01), Bhatia
patent: 4939294 (1990-07-01), Agreda et al.
patent: 4966982 (1990-10-01), Ono et al.
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
patent: 5264592 (1993-11-01), Fridman et al.
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.
Cleary et al., "Separation Of Closely Boiling Mixtures By Reactive Distillation. 2. Experiments", pp. 1071-1073, 1985, Ind. Eng. Chem. Process Des. Dev., vol. 24.
Dadgar et al., "Improving The Acetone-Butanol Fermentation Process With Liquid-Liquid Extraction", pp. 36-39, 1988, Biotechnology Progress, vol. 4, No. 1.
DeGarmo et al., "Consider Reactive Distillation", pp. 43-50, 1992, Chemical Engineering Progress, Mar.
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.
Earhart et al., "Waste Recovery: Recovery Of Organic Pollutants Via Solvent Extraction", pp. 67-73, 1977, CEP, May.
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 Dilacide Of Racemic Lactic Acid", pp. 502-505, 1905, Academie Des Sciences, Meeting of 20 Feb.
Jungfleisch et al., "Organic Chemistry--On The Dilactide Of The Right", pp. 111-113, 1905 Academie Des Sciences, Meeting Of 10 Jul.
Jungfleisch et al., "Organic Chemistry--On The Dilactide Of Left Lactic Acid", pp. 637-639, 1906, Academie Des Sciences, Meeting Of 12 Mar.
Jungfleisch et al., "Organic Chemistry--On Ethyl Lactyllactate", 1907, Academie Des Sciences, Meeting Of 25 Feb.
Jungfleisch et al., "Organic Chemistry--On Active Dilactylic Acid", p. 979, 1907, Academie Des Sciences, Meeting of 6 May.
King, "Amine-Based Systems For Carboxylic Acid Recovery", pp. 285-291, 1992, Chemtech, Mar.
Kleine et al., "High Molecule 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.
Marlatt et al., "Acetone-Butanol Fermentation Process Development And Economic Evaluation", pp. 23-28, 1986, Biotechnology Progress, vol. 2, No. 1.
Montgomery, "Acidic Constituents Of Lactic Acid-Water Systems", pp. 1466-1468, 1952, J. Am. Chem. Soc., vol. 74.
Alen et al., "Condensation Of Glycolic, Lactic And 2-Hydroxybutanoic Acids During Heating And Identification Of The Condensation Products By GLC-MS", pp. 633-636, 1980, Acta Chemica Scandinavica B, vol. 34, No. 9.
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", 1893, pp. 262-265, Chem. Ber, vol. 26.
Busche, "Recovering Chemical Products From Dilute Fermentation Broths", pp. 597-615, 1983, Biotechnology And Bioengineering Symp., No. 13.
Othmer, "Acetic Acid Recovery Methods", pp. 48-59, 1958, Chemical Engineering Progress, vol. 54, No. 7.
Ricker et al., "Solvent Extraction For Treatment Of Wastewaters From Acetic-Acid Manufacture," pp. 204-209, 1978, The American Institute Of Chemical Engineers, vol. 74, No. 178.
Tamada et al., "Extraction Of Carboxylic Acids With Amine Extractants. 1. Equilibria And Law Of Mass Action Modeling", pp. 1319-1326, 1990, Ind. Eng. Chem. Res., vol. 29, No. 7.
Tamada et al., "Extraction Of Carboxylic Acids With Amine Extractants. 2. Chemical Interactions And Interpretation Of Data", pp. 1327-1333, 1990, Ind. Eng. Chem. Res., vol. 29, No. 7.
Tamada et al., "Extraction Of Carboxylic Acids With Amine Extractants. 3. Effect Of Temperature, Water Coextraction, and Process Considerations", pp. 1333-1338, 1990, Ind. Eng. Chem. Res., vol. 29, No. 7.
Terrill et al., "Separation Of Closely Boiling Mixtures By Reactive Distillation 1. Theory", pp. 1062-1071, 1985, Ind. Eng. Chem. Process Des. Dev., vol. 24, No. 4.
Watson, "Composition Of Lactic Acid. Production Of A Highly Concentrated Acid", pp. 399-401, 1940, Industrial And Engineering Chemistry, vol. 32, No. 3.
Wise
Allen Anthony E.
Cheung Alex
Cremeans George E.
Eggeman Timothy J.
Evanko William A.
BioPak Technology, Ltd.
Covington Raymond
Ivy C. Warren
LandOfFree
Method to produce cyclic esters does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Method to produce cyclic esters, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Method to produce cyclic esters will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-363368