US3419588A - Process for continuously deacidifying glyceride oils - Google Patents

Process for continuously deacidifying glyceride oils Download PDF

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Publication number
US3419588A
US3419588A US580390A US58039066A US3419588A US 3419588 A US3419588 A US 3419588A US 580390 A US580390 A US 580390A US 58039066 A US58039066 A US 58039066A US 3419588 A US3419588 A US 3419588A
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oil
alkaline liquid
soap
free fatty
washing
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US580390A
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Man Willem De
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Lever Brothers Co
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Lever Brothers Co
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B3/00—Refining fats or fatty oils
    • C11B3/02—Refining fats or fatty oils by chemical reaction
    • C11B3/06—Refining fats or fatty oils by chemical reaction with bases

Definitions

  • the invention relates to deacidification and especially to a continuous process for deacidifying lyceride oils using an alkaline liquid.
  • glyceride oils used in this specification includes both fatty acid glycerides that are normally solid and also those that are liquid at the normal temperature. Glyceride oils obtained by extraction, expression, or other processes from vegetable or animal raw material always contain a larger or smaller proportion of free fatty acids. Before these oils can be used for the preparation of foodstuffs, the free fatty acids and other accompanying impurities, erg. phosphatides, must be removed or separated.
  • the invention relates to a process for the continuous deacidification of glyceride oils by means of an alkaline liquid in which the losses of neutral oil are reduced to a minimum.
  • the oil is caused to flow in the form of a thin layer and along its surface or a part of it, it is brought into contact with a mist of the alkaline liquid to bring about the neutralisation of the free fatty acids.
  • neutralisation occurs after which the aqueous phase containing soap and impurities is separated from the neutral oil.
  • the alkaline liquid in finely divided form is brought into contact with a thin layer of oil in order to obtain a large contact area, so that a very short time of neutralisation is achieved and, moreover, the inclusion of oil droplets in larger soap droplets is avoided.
  • the formation of emulsions is almost completely avoided by means of the gentle addition of small droplets of alkaline liquid to the slowly flowing thin layer of oil.
  • this process requires only a small excess of alkaline liquid, so that the saponification of neutral oil is reduced in a desirable :manner.
  • the angle of incidence of the drops of alkaline liquid accelerated in the direction of flow of the oil should be as small as possiblenot more than -and the velocity and the kinetic energy of the droplets of alkaline liquid should be so low that, when they meet, the velocities of the oil and the alkaline liquid are as nearly as possible equal and the reaction therefore takes place in cocurrent flow.
  • the cocurrent cont-act of oil and alkaline liquid is advantageous since no shear forces occur between oil and alkaline liquid, so that the use of very fine droplets of alkaline liquid is possible without the danger of the formation of an emulsion.
  • the uniform distribution of the droplets of alkaline liquid in the cocurrent contact guarantees that stoichiometric neutralisation conditions prevail throughout the mixture. In this way the saponification of neutral oil caused by local excesses of alkaline liquid and the formation of acid soaps due to local deficiencies of alkaline liquid are avoided.
  • the mixture moves in substantially nonturbulent flow, preferably at Reynolds numbers between 1000 and 5000.
  • the time of contact between oil and alkaline liquid will be less than 15 seconds. After the brief and gentle cocurrent contact between oil and alkaline liquid, a coalescence of the droplets both of oil and soap occurs.
  • the mixture of oil and soap is led to a settling vessel where a direct separation of the two phases takes place, since no stable emulsions are present.
  • the thickness of the oil layer must be between certain limits since when the oil layer is too thick the droplets of alkaline liquid are not distributed uniformly in the oil and when the oil layer is too thin the throughput of the unit concerned will be unnecessarily low. In general, the thickness of the oil layer to achieve optimum results is 1 to 3 mm.
  • a suitable process for obtaining a continuously flowing uniform layer of oil consists in passing the oil over downwardly inclined surfaces making a small angle, for example, between 0 and 25, with the horizontal. At larger angles, the uniform and continuous flow of the oil may be disturbed by excessively high rates of flow leading to turbulence which can promote the formation of emulsions.
  • the droplets of the alkaline liquid that are brought into contact with the slowly flowing layer of oil. should have a diameter of not more than 1.0 mm., i.e., a diameter between 0.01 mm. and 1.0 mm., preferably a mean diameter of 0.1 mm. These droplets, which are obtained, for example, by spraying the alkaline liquid by means of a nozzle, are caused to contact the layer of oil practically without having any residual kinetic energy. When the droplets of alkaline liquid are greater than 1.0 mm., the good contact between oil and droplets of alkaline liquid may be effected.
  • the oil layer need not be uniform or coherent during the whole process.
  • alkaline liquid it is advantageous to use sodium hydroxide for the alkaline liquid, but other alkaline agents may be used as well provided that they can be sprayed.
  • an alkaline liquid with a concentration of 005-20 N is used, the range from 0.1 N to 1.2 N being preferred.
  • the optimum concentration of the alkaline liquid may be different from each oil and, moreover, different for the same type oil according to the lecithin content of the oil.
  • a certain excess of alkaline liquid for example, l80%--may be used, but this again depends on the oil being treated.
  • Small amounts of electrolytes such as, for example, NaCl may be advantageous in the alkaline liquid.
  • the temperature during the process is chosen according to the type of oil present but is usually above 80 C., although temperatures higher than 100 are possible and are necessary in certain cases to achieve optimum results. In the latter case, the whole process is carried out in a closed apparatus under pressure and the alkaline liquid is sprayed in inert gases. All steps of the process must then be carried out under a pressure high enough to prevent the boiling of the soap solution.
  • the upper temperature limit is determined by the increasing hydrolysis reactions at these temperatures. In this process, the pressure will in general be in the range up to 6 atm. gauge, under which conditions reaction temperatures up to 160 C. may be used.
  • the process according to the invention can be used for a large number of crude oils. Even those oils which have a very high content of free fatty acids can be refined until their content of free fatty acids is reduced to less than 0.15%.
  • the process condtions such as temperature, concentration of alkali, concentration of electro lytes, etc., may be varied so that even oils which are difficult to deacidify because of their high content of mainly C and higher saturated fatty acids can be treated in a satisfactory manner without appreciable emulsification occurring.
  • oils of the lauric acid group especially coconut and palm kernel oils
  • oleic-linoleic group especially cottonseed, groundnut, corn oil, sunflower and safflower oil (all containing over 40% of combined linoleic acid and composed substantially of glycerides of C and C fatty acids the latter predominating and more highly unsaturated acids than linoleic being substantially absent, and palm oil (which palmitic and oleic acids predominate, with a much smaller proportion of linoleic); of the linolenic group especially those which contain only small proportions, e.g., 2 to 5 or of this acid with over 40% of linoleic acid and substantially no C to C acids, e.g., soyabean and wheat germ oil; and of the erucic acid group, especially rape seed and mustard oils.
  • the process is also applicable to the neutralisation of tallow.
  • the direct separation of the two phases may take place in a settling vessel.
  • the deacidified oil ca b t e t d f h r in a p cked c l m o s i countercurrent extraction apparatus by washing with water or a dilute alkaline solution to remove traces of soap.
  • a suitable washing column contains packing consisting of spheres, saddles, or rings, the deacidified oil being fed into the device at the bottom below the layer of packing and the washing liquid being fed in above the layer of packing.
  • the washing column may contain several layers of packing.
  • the mixture of soap and oil is, for example, fed into a centrifugal separator, the neutral oil issuing at the top and the soap at the bottom.
  • a post-deacidification/ washing process may take place in a layer of packing in a packed column following the separator in which the oil is fed in at the bottom and rises in subdivided form in countercurrent to the continuous water phase, which may also contain alkali.
  • the issuing washing liquid which contains traces of soap, can be fed to the separator or be combined with the soap leaving the separator.
  • the oil can be treated with washing water in a second washing column or in the second part of the same washing column. In this case, the oil phase remains continuous and the wash water, fed in at the top, is finely subdivided.
  • a centrifuge can be used as a highoutput separator when care is taken that turbulence and, therefore, the formation of emulsions in the two-phase system is avoided at its entry into the centrifuge. Because no emulsion is present, the centrifuge can separate the mixture satisfactorily.
  • the oil can be passed over an inclined surface and the alkaline liquid be sprayed onto this layer of oil.
  • This surface may have the form of a funnel, with one or more spray nozzles for the alkaline solution being arranged in such a way that the droplets of alkaline liquid come into contact with the layer of oil uniformly, after which the mixture of oil and soap flows through the central discharge tube into a separating device.
  • the oil may also flow in a thin layer over a plate connected with a hori zontal channel which leads the mixture of oil and soap via a discharge tube to the separating device.
  • the spray nozzles which spray the droplets of alkaline liquid onto the flowing layer of oil can be arranged over the end of the plate where the plate leads into the channel.
  • the oil may be allowed to flow in the form of a layer over a horizontal or slightly inclined surface on which an overflow weir is arranged.
  • a chamber containing the spray nozzles for the alkaline liquid is arranged over the overflow weir.
  • the layer of oil may be present on a moving surface for example, rollers or plates-which is sprayed with droplets of alkaline liquid and from which the mixture of oil and soap can be scraped off or thrown off by centrifugal force.
  • the layer of oil can be put in motion by means of a slowly rotating drum, the droplets. of alkaline liquid being sprayed onto the layer of oil, and the resulting mixture of oil and soap being scraped off.
  • the oil can be fed from below onto a stationary or slowly rotating plate which is horizontal or has a slight downward Slope outwards, so that it spreads out uniformly in all directions.
  • the alkaline liquid is sprayed uniformly on to the thin layer of oil.
  • the resulting mixture of oil and soap runs into a collecting channel arranged round the plate and from this into the separating device.
  • the crude oil is pumped by means of pump 1 to a heating device 2 where it is heated to about 95 C.
  • the heated oil is fed via conduit 5, provided with a Rotarneter 3 into the lower conical part 7 of vessel 4.
  • the oil is distributed in a thin layer along the inner surface of the conical part of the vessel by means of an annular conduit 6 provided at the bottom with small holes.
  • the alkaline solution is pumped from the container 9 through a filter 10 and a heating device 12 by means of pump 11 into the neutralisation vessel 4.
  • the alkaline liquid is heated to a temperature of about 95 C.
  • a rotameter 13 is again provided in the conduit.
  • the alkaline liquid flows into the upper part of the neutralisation vessel through the feed conduit 14 and is sprayed by means of nozzle 15 on to the layer of oil.
  • the nozzle is so directed that the mist comes into contact uniformly with the layer of oil present on the conical part of the neutralisation vessel.
  • the mixture of oil and soap leaves the neutralisation vessel through the discharge pipe 8, which is connected with a separating device 16, for in stance a centrifuge.
  • the discharge pipe 8 has an inspection sight glass 19 below the cone and a sample cock 20. In the device 16, the soaps formed and other impurities of the oil are separated from the oil.
  • the neutral oil is taken ofi through outlet 17 and the soap through outlet 18 (FIG. 1).
  • the deacidified oil can 'be washed with a weakly alkaline liquid and/or hot water in a subsequent packed washing column 21 shown in FIGURE 2 in order to remove traces of soap that may still be present.
  • the alkaline liquid is fed into the bottom 21 and the hot water into the top 22 of the washing column.
  • a post-deacidification process can be carried out in the same apparatus, if desired.
  • EXAMPLE 1 A crude coconut oil with a free fatty acid content of 15.35% was deacidified at 8085 C. with 0.9 N caustic soda solution in an apparatus as shown in the figures. The throughput of crude oil was 280 kg./hour. The excess of alkali was 5%.
  • the oil and the alkaline solution or oil and soap were in close contact for approximately 15 seconds, after which the mixture of oil and soap entered the separator.
  • a sample taken from the sample cock showed that the neutralisation of the free fatty acids in the oil was complete.
  • the mixture of oil and soap of this sample separated after a short time.
  • the analysis of the separated oil showed a free fatty acid content below the prescribed percentage content of free fatty acid for neutral oil namely 0.1%.
  • the deacidified oil was treated in countercurrent with a 0.1 N solution of caustic soda in the lower part of the washing column at a temperature of 95 C.
  • the column was filled with packing rings with a diameter of 2.5 cm.
  • the oil was washed with hot water litres/hour) at a temperature of 90 C. in the top part of the same apparatus.
  • 3379 kg. of water-free neutral oil was obtained from 3575 kg. of crude coconut oil, the content of free fatty acids being 0.07% and the content of soap 0.03%.
  • the alkali used had a normality of 1.0 N.
  • the throughput was 300 kg. of crude oil per hour
  • the deacidification and separation were carried out in the apparatus described.
  • the separating vessel was followed by a packed column for washing.
  • the alkali used had a normality of 1.0 N.
  • the throughput was 400 kg. of crude oil per hour.
  • the deacidification and separation took place in the apparatus described.
  • the separating vessel was followed 1 by a packed column for washing.
  • Acid number 262 saponification number 266 Degree of splitting percent 98.5 Content of free fatty acids in the acid oil percent 97.0
  • the alkali used had a normality of 0.5 N.
  • the throughput was 450 kg. of crude oil per hour.
  • the deacidification and separation were carried out in the apparatus described.
  • the separating vessel was followed by a packed column for washing.
  • the alkali used had a normality of 0.5 N.
  • the throughput was 450 kg. of crude oil per hour.
  • the deacidification and separation were carried out in the apparatus described.
  • the separating vessel was followed by a packed column for washing.
  • a process for continuously deacidifying glyceride oil containing free fatty acids and other impurities while avoiding substantial emulsification and saponification which comprises flowing said oil through a contact zone in which the oil in the form of a coherent thin film is contacted with an aqueous alkaline liquid by spraying the film with droplets of the said liquid having an average particle size of from 0.1 to 1 mm. diameter, in a non-disruptive impact, maintaining the resultant substantially non-turbulent mixture in cocurrent flow and subsequently separating the resultant neutral oil from the resultant soap-containing and impurity-containing aqueous phase.
  • a process for continuously deacidifying glyceride oil containing free fatty acids and other impurities while avoiding substantial emulsification and saponification which comprises flowing a thin layer of said oil having a thickness of from about 1 to about 3 millimeters at an incline of from to about 25 from the horizontal, spraying droplets having an average diameter of from about 0.01 to about 1.0 millimeter in a nondisruptive impact of an aqueous alkaline liquid onto said oily layer, maintaining the resultant laminar cocurrent flow of the substantially non-turbulent mixture for a neutralization period of time up to about 15 seconds and thereafter separating the resultant neutral oil from the resultant soap-containing and impurity-containing aqueous phase.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Fats And Perfumes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US580390A 1965-09-30 1966-09-19 Process for continuously deacidifying glyceride oils Expired - Lifetime US3419588A (en)

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US (1) US3419588A (de)
BE (1) BE687590A (de)
DE (1) DE1642902A1 (de)
GB (1) GB1154229A (de)
LU (1) LU52070A1 (de)
NL (1) NL6613644A (de)

Cited By (16)

* Cited by examiner, † Cited by third party
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WO2014165859A1 (en) * 2013-04-06 2014-10-09 Agilyx Corporation Systems and methods for conditioning synthetic crude oil
US9145520B2 (en) 2006-08-24 2015-09-29 Agilyx Corporation Systems, and methods for recycling plastic
US9795567B2 (en) 2008-11-04 2017-10-24 Jazz Pharmaceuticals, Inc. Immediate release formulations and dosage forms of gamma-hydroxybutyrate
US10398662B1 (en) 2015-02-18 2019-09-03 Jazz Pharma Ireland Limited GHB formulation and method for its manufacture
US10758488B2 (en) 2010-03-24 2020-09-01 Jazz Pharmaceuticals, Inc. Controlled release dosage forms for high dose, water soluble and hygroscopic drug substances
US11400065B2 (en) 2019-03-01 2022-08-02 Flamel Ireland Limited Gamma-hydroxybutyrate compositions having improved pharmacokinetics in the fed state
US11400052B2 (en) 2018-11-19 2022-08-02 Jazz Pharmaceuticals Ireland Limited Alcohol-resistant drug formulations
US11407947B2 (en) 2020-12-10 2022-08-09 Agilyx Corporation Systems and methods for recycling waste plastics
US11426373B2 (en) 2017-03-17 2022-08-30 Jazz Pharmaceuticals Ireland Limited Gamma-hydroxybutyrate compositions and their use for the treatment of disorders
US11504347B1 (en) 2016-07-22 2022-11-22 Flamel Ireland Limited Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics
US11583510B1 (en) 2022-02-07 2023-02-21 Flamel Ireland Limited Methods of administering gamma hydroxybutyrate formulations after a high-fat meal
US11602513B1 (en) 2016-07-22 2023-03-14 Flamel Ireland Limited Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics
US11602512B1 (en) 2016-07-22 2023-03-14 Flamel Ireland Limited Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics
US11779557B1 (en) 2022-02-07 2023-10-10 Flamel Ireland Limited Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics
US11839597B2 (en) 2016-07-22 2023-12-12 Flamel Ireland Limited Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics
US11986451B1 (en) 2016-07-22 2024-05-21 Flamel Ireland Limited Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2327569A (en) * 1941-03-29 1943-08-24 Refining Inc Process of refining
US2906606A (en) * 1951-11-05 1959-09-29 Signer Rudolf Apparatus for the separation of mixtures of substances
US3226407A (en) * 1962-10-22 1965-12-28 Bergman Lars Olof Process for acid and then alkaline refining fatty oils

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2327569A (en) * 1941-03-29 1943-08-24 Refining Inc Process of refining
US2906606A (en) * 1951-11-05 1959-09-29 Signer Rudolf Apparatus for the separation of mixtures of substances
US3226407A (en) * 1962-10-22 1965-12-28 Bergman Lars Olof Process for acid and then alkaline refining fatty oils

Cited By (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9145520B2 (en) 2006-08-24 2015-09-29 Agilyx Corporation Systems, and methods for recycling plastic
US9795567B2 (en) 2008-11-04 2017-10-24 Jazz Pharmaceuticals, Inc. Immediate release formulations and dosage forms of gamma-hydroxybutyrate
US10959956B2 (en) 2010-03-24 2021-03-30 Jazz Pharmaceuticals, Inc. Controlled release dosage forms for high dose, water soluble and hygroscopic drug substances
US10966931B2 (en) 2010-03-24 2021-04-06 Jazz Pharmaceuticals, Inc. Controlled release dosage forms for high dose, water soluble and hygroscopic drug substances
US11207270B2 (en) 2010-03-24 2021-12-28 Jazz Pharmaceuticals, Inc. Controlled release dosage forms for high dose, water soluble and hygroscopic drug substances
US11090269B1 (en) 2010-03-24 2021-08-17 Jazz Pharmaceuticals, Inc. Controlled release dosage forms for high dose, water soluble and hygroscopic drug substances
US10758488B2 (en) 2010-03-24 2020-09-01 Jazz Pharmaceuticals, Inc. Controlled release dosage forms for high dose, water soluble and hygroscopic drug substances
US10813885B1 (en) 2010-03-24 2020-10-27 Jazz Pharmaceuticals, Inc. Controlled release dosage forms for high dose, water soluble and hygroscopic drug substances
US10987310B2 (en) 2010-03-24 2021-04-27 Jazz Pharmaceuticals, Inc. Controlled release dosage forms for high dose, water soluble and hygroscopic drug substances
US9493713B2 (en) 2013-04-06 2016-11-15 Agilyx Corporation Systems and methods for conditioning synthetic crude oil
WO2014165859A1 (en) * 2013-04-06 2014-10-09 Agilyx Corporation Systems and methods for conditioning synthetic crude oil
US9162944B2 (en) 2013-04-06 2015-10-20 Agilyx Corporation Systems and methods for conditioning synthetic crude oil
US11077079B1 (en) 2015-02-18 2021-08-03 Jazz Pharmaceuticals Ireland Limited GHB formulation and method for its manufacture
US10398662B1 (en) 2015-02-18 2019-09-03 Jazz Pharma Ireland Limited GHB formulation and method for its manufacture
US11147782B1 (en) 2015-02-18 2021-10-19 Jazz Pharmaceuticals Ireland Limited GHB formulation and method for its manufacture
US11364215B1 (en) 2015-02-18 2022-06-21 Jazz Pharmaceuticals Ireland Limited GHB formulation and method for its manufacture
US11839597B2 (en) 2016-07-22 2023-12-12 Flamel Ireland Limited Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics
US12109186B2 (en) 2016-07-22 2024-10-08 Flamel Ireland Limited Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics
US12115144B2 (en) 2016-07-22 2024-10-15 Flamel Ireland Limited Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics
US12115143B2 (en) 2016-07-22 2024-10-15 Flamel Ireland Limited Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics
US11504347B1 (en) 2016-07-22 2022-11-22 Flamel Ireland Limited Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics
US12115145B2 (en) 2016-07-22 2024-10-15 Flamel Ireland Limited Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics
US11602513B1 (en) 2016-07-22 2023-03-14 Flamel Ireland Limited Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics
US11602512B1 (en) 2016-07-22 2023-03-14 Flamel Ireland Limited Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics
US11766418B2 (en) 2016-07-22 2023-09-26 Flamel Ireland Limited Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics
US12115142B2 (en) 2016-07-22 2024-10-15 Flamel Ireland Limited Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics
US11826335B2 (en) 2016-07-22 2023-11-28 Flamel Ireland Limited Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics
US12097175B2 (en) 2016-07-22 2024-09-24 Flamel Ireland Limited Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics
US11896572B2 (en) 2016-07-22 2024-02-13 Flamel Ireland Limited Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics
US11986451B1 (en) 2016-07-22 2024-05-21 Flamel Ireland Limited Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics
US12097176B2 (en) 2016-07-22 2024-09-24 Flamel Ireland Limited Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics
US11426373B2 (en) 2017-03-17 2022-08-30 Jazz Pharmaceuticals Ireland Limited Gamma-hydroxybutyrate compositions and their use for the treatment of disorders
US11400052B2 (en) 2018-11-19 2022-08-02 Jazz Pharmaceuticals Ireland Limited Alcohol-resistant drug formulations
US11400065B2 (en) 2019-03-01 2022-08-02 Flamel Ireland Limited Gamma-hydroxybutyrate compositions having improved pharmacokinetics in the fed state
US11407947B2 (en) 2020-12-10 2022-08-09 Agilyx Corporation Systems and methods for recycling waste plastics
US11779557B1 (en) 2022-02-07 2023-10-10 Flamel Ireland Limited Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics
US11583510B1 (en) 2022-02-07 2023-02-21 Flamel Ireland Limited Methods of administering gamma hydroxybutyrate formulations after a high-fat meal

Also Published As

Publication number Publication date
DE1642902A1 (de) 1971-05-19
LU52070A1 (de) 1968-03-30
BE687590A (de) 1967-03-29
NL6613644A (de) 1967-03-31
GB1154229A (en) 1969-06-04

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