CN1304414A - Preparation of organic salt of aspartame - Google Patents
Preparation of organic salt of aspartame Download PDFInfo
- Publication number
- CN1304414A CN1304414A CN99807046A CN99807046A CN1304414A CN 1304414 A CN1304414 A CN 1304414A CN 99807046 A CN99807046 A CN 99807046A CN 99807046 A CN99807046 A CN 99807046A CN 1304414 A CN1304414 A CN 1304414A
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- apm
- salt
- ace
- aqueous solution
- aspartame
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06104—Dipeptides with the first amino acid being acidic
- C07K5/06113—Asp- or Asn-amino acid
- C07K5/06121—Asp- or Asn-amino acid the second amino acid being aromatic or cycloaliphatic
- C07K5/0613—Aspartame
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
- A23L27/31—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives
- A23L27/32—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives containing dipeptides or derivatives
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Health & Medical Sciences (AREA)
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- Genetics & Genomics (AREA)
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- General Health & Medical Sciences (AREA)
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- Biochemistry (AREA)
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- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
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Abstract
The invention relates to a process for the preparation of the salt of aspartame and acesulphamic acid on solid and dried form by preparation in a liquid medium and separation therefrom as a wet solid product by means of solid-liquid separation and subsequent drying, characterised in that said wet solid product, before being dried, is subjected to a washing operation in one or more steps, with at least the last of these washing oparations being effected with the aid of a basic aqueous solution having a pH of 8 or higher. The obtained solid dried procuct has an improved stability as compared with the product of the state of the art. The invention also relates to salt of aspartame and acesulphamic acid having such an increased stability that the acetoecetamide content upon heating of that salt in dry form at a temperature of 80 DEG C for 48 hours remains lower than 10 ppm relative to the dry weight of the salt.
Description
Thereby the present invention relates to a kind ofly separate method with the salt of the isolated in form of wet solid product and aspartame that subsequent drying prepares solid and dried forms and acesulfame acid by preparation in liquid medium and by solids liq.According to the present invention, obtain dried forms, stability-enhanced, especially under being exposed to the temperature of rising, its salt shows to form the dangerous aspartame that reduces of aceto-acetamide and the salt of acesulfame acid.The invention still further relates to the salt of new aspartame and acesulfame acid.
The salt of aspartame and acesulfame acid is a kind of sweetener, sugar about 200 times increases sweet ability when having by weight, it is particularly useful in powdered mixture, chewing gum, candy and the dried food, especially except that sweetener, also be used for the various products that comprise as the compound of aldehyde etc., wherein these compounds may with sweetener, the reaction do not expect takes place as aspartame.
The salt of aspartame and acesulfame acid is by strong sweetener aspartame, and 2-L-aspartyl-L-phenylalanine methyl esters (hereinafter being also referred to as APM) and acesulfame acid are formed, and wherein the former is had for a long time by known.Acesulfame acid is for deriving from the acid of strong sweetener acesulfame potassium, and wherein this sylvite structural formula is the 6-methyl isophthalic acid, and 2,3-Evil thiazine-4 (3K)-ketone-2,2-dioxide (hereinafter being also referred to as AceK), it is also had for a long time by known.Acesulfame acid also is called as AceH hereinafter, and the salt of APM and AceH also is called as APM.Ace.
Preparation with APM.Ace of fabulous thermostability and agent of low hygroscopicity form is disclosed among the EP-A-0768041.Among the preparation method of APM.Ace in being disclosed in EP-A-0768041, this salt obtains with the solid form as the result of anti-salify (trans-salification) process of carrying out in liquid medium.As the composition in the reaction system of using (being generally slurry), specifically by (ⅰ) aspartame, (ⅱ) inorganic salt, for example sylvite of acesulfame acid and (ⅲ) strong acid, for example hydrochloric acid is formed.Described composition can be added in the reaction system with any required order, but system keeps moving and keeping whipped state with being stabilized, produces component distribution relatively uniformly like this, and can not have undesirable too high local acid concentration.Described in applying for as described, pass through method relatively fast usually, preferably in water-bearing media, under the temperature of-20 ℃ of-+90 ℃ of scopes, carry out preparation according to the APM.Ace of described patent application.EP-A-0768041 does not provide relevant recovery, drying and/or is further purified the information of the APM.Ace of formation.Used standard method as the solid that obtains with the frozen water washing and filtering, is satisfied acquisition fully in the requirement that has the product of fabulous thermostability aspect the thermal properties of the APM of salt part.
EP-A-0768041 pays particular attention to the thermostability of the APM part of salt, because the thermostability of known APM is usually less than AceK.Explanatorily be in passing, also known acid corresponding to AceK, acesulfame acid (AceH), itself has ratio such as the lower stability of AceK.Therefore Ace among APM.Ace part, never notes any degradation production of the Ace part among the APM.Ace to exist with mode identical in AceK.
According to EP-A-0768041, when 120 ℃ of heating 1 hour, or 70 ℃ of heating 70 hours, when taking place less than 0.5% decomposition, APM.Ace (dried forms) has good thermostability.Obviously as seen, among the comparative experiments 1C and 1D that only carries out in methyl alcohol, the decomposition of the Ace of APM.Ace part is tangible from the table of described patent application.
Yet, simultaneously clearly, when being exposed to the temperature of rising for a long time with dried forms, particularly-this is construed to standard conditions-for example hereinafter, 80 ℃, 48 hours, even under the low water capacity of the dry APM.Ace that the method according to EP-A-0768041 prepares, in APM.Ace, form detectable aceto-acetamide concentration, promptly than the high concentration of limit of detection based on the 10ppm of the dry weight of APM.Ace.Aceto-acetamide also is called as 3A hereinafter.
Owing to the toxicity reason, in food and the material that uses in food thus, particularly aceto-acetamide is limited in lower concentration.With reference to European Pharmacopoeia (supplementary issue, 1998) acetoacetyl amine moiety, for example, maximum acceptable concentration is 1250.Therefore, it is considered to important according to the applicant, and also because the applicant has confirmed that the formation of aceto-acetamide is that autocatalytically is carried out simultaneously, promptly concentration is high more, but carry out soon more-prevent the formation of the 3A of detectable level in APM.Ace.
The objective of the invention is to address the above problem, especially at the formation that prevents or stop 3A among the APM.Ace.
Be unexpectedly, the present invention reaches this purpose, before drying, separate the washing operation of the one or more steps of wet solid product process that obtain by solid-liquid, wherein the final step washing operation carries out by means of pH8 or higher alkaline aqueous solution at least.
After the drying, the APM.Ace of Huo Deing reaches the standard of setting like this, and in the temperature that is exposed to rising with dried forms for a long time, promptly 80 ℃ the time, in the time of 48 hours, based on the dry weight of APM.Ace, the content of 3A is not higher than 10ppm.
In the temperature that is lower than 80 ℃, for example under 70 ℃, according to applicant's observation, in APM.Ace the formation of 3A slower, even under lower temperature, the effect of its formation almost can be ignored.For example, APM.Ace (produced according to the present invention) stores the concentration that can not produce detectable 3A in 12 months for 60 ℃, and APM.Ace not prepared in accordance with the present invention stores the 3A that contained 10-20ppm in 1 month at 60 ℃.Store APM.Ace during 1 year at 40 ℃, but in beginning to comprise the APM.Ace of 3A, not have the 3A of formation detection limit.
According to the applicant, the formation of 3A now may be interpreted as the result of the micro-AceH reaction of existence.Its reason is under the influence of (2 molecule) water, and aceto-acetamide-N-sulfonic acid can be formed by (1 molecule) AceH, especially should acid can react the formation aceto-acetamide subsequently.The applicant has now found that this reacts autocatalytically and carries out.
Notice-also resemble described EP-A-0768041 described-if this is to be similar to the preparation of the described method of ES-A-8604766, the water capacity of APM.Ace is usually above the method according to EP-A-0768041.In this case, under the condition of storage and long-time heating, the problems referred to above of formation 3A thereby bigger.
For prepare the APM.Ace that adopts among the present invention at liquid medium, can adopt any suitable method.The case description of these methods is in EP-A-0768041 and ES-A-8604766 that this paper quotes.In order further to explain liquid medium and the condition and the solid-liquid separation method of method, the therefore content of the described patent application of reference that can be used in those methods.Be equally applicable to explain in order to obtain the APM.Ace of dried forms, finish the drying step that carries out behind the washing operation in the present invention.
In the method according to the invention, can carry out the washing operation of one or more steps, should understand in all cases, last washing step uses pH8 or higher basic solution to carry out.If carry out a step washing operation, and therefore use this basic solution to wash, should give special concern to washing out the inorganic salt that are present in the product so at once.In the case, needs alkalescence is stronger washing liq is to obtain identical wash result.
As having pH8 or higher alkaline aqueous solution, can be chosen in any inorganic or solution of organic compound that produces pH8 or higher solution under the concentration of use in principle.Relate to the place of pH in this patent application, in all cases, the pH of the solution of discussion refers to the value of using the pH meter of calibration to measure in room temperature (20 ℃).For those skilled in the art, obviously do not use in the present invention, or use the back in the product that obtains, to stay the alkali of undesirable pollutent or undesirable smell or taste properties with undesirable mode and APM.Ace reaction.Preferably, use the alkali that in the APM.Ace that reclaims, does not stay or stay few resistates.
The example that can be used for the alkali of the alkali aqueous solution among the present invention comprises inorganic hydroxide, as alkali metal hydroxide and alkaline earth metal hydroxides, for example sodium, potassium, calcium and magnesium oxyhydroxide, but for example also has ammonium hydroxide, and organic bases, for example Sodium Benzoate or potassium and be applicable to the preparation food similar alkali.
Preferred sodium hydroxide of alkaline aqueous solution and/or potassium hydroxide solution.
Preferably, use the aqueous solution of the alkali of pH 8-13 to carry out the neutralizing treatment step, especially use the aqueous solution of pH for the alkali of about 11.5 scopes of about 10.5-.If select high pH, for example 13.5 or higher pH, exist the APM among the APM.Ace to begin racemize and/or undesirable side reaction takes place, the danger that increases as the formation degree of ester hydrolysis or diketopiperazine.The pH of alkaline aqueous solution of washing step is selected to be lower than 8 if be used for, and the effect of washing step is too little.
Usually, the temperature that is used for the basic solution of washing step will not be higher than 20 ℃, preferably in 15-5 ℃ scope.Washing step itself also preferably carries out under the above-mentioned temperature that is used for basic solution.This prevents the unnecessary temperature variation in the washing operation.When the temperature of carrying out washing operation is higher, increase from the amount of the required product of mother liquor separation losses.In fact the amount of the dissolved APM.Ace that removes from mother liquor can be recovered, but this needs unnecessary other treatment step.
The time that is used for the neutralizing treatment step, promptly the residence time of the solid APM.Ace that reclaims in the presence of basic solution is not very crucial.Those skilled in the art can easily determine the top condition of washing operation.Obviously, along with the neutralizing treatment operation is carried out the longer time, decompose and/or form the danger increase of undesirable by product.Usually, APM.Ace contacts the several seconds at least with basic solution, be no more than several minutes usually, for example 2-20 minute.The time that is used for the neutralizing treatment operation obviously depends in part on amount and the equipment used of the APM.Ace of washing for those skilled in the art, and the liquid medium that is present in during this period in the wet crystal cake is in fact substituted by basic solution.
Basic solution washing operation and any washing operation the preceding can use any crystal washing methods known in the art to carry out.In a specific embodiments, to separate by solid-liquid, the APM.Ace crystal block that for example horizontal filter cloth obtains is handled with alkaline washing liquid on identical filter cloth, choose wantonly and using superpressure on the filter cloth or under filter cloth, using negative pressure, at first on (little) layer at the top of crystal block, use alkaline washing liquid, then discharge it by crystal block and filter cloth.Filter cloth also can be contained in the whizzer.
Before carrying out washing step with basic solution, preferably at first carry out at least water washing operation according to the present invention.This feasible amount and because formation of any by product that the alkaline washing step causes itself that can limit according to alkali wash water required for the present invention.If desired, before dry concentrated APM.Ace, also alkaline washing step according to the present invention can be repeated one or many to obtain required desciccate by means of method known to those skilled in the art.
The amount that is used for according to the alkaline detergent solution of the inventive method is not crucial usually.Preferably, use is with respect to the basic solution of at least 10% (weight) of the amount of APM.Ace (in dry weight basis).The optimum quantity of washing liq can be determined by those skilled in the art simply that it depends on the mode for preparing APM.Ace and depends on condition of being got and the equipment that carries out the alkaline washing step.For example the residual water capacity of wet crystal block is low more, and the amount of the alkaline detergent solution that need use is low more.
The thus obtained APM.Ace that remains wet can be by then with any known mode drying after carrying out washing step.Especially when those specific embodiments according to the above-mentioned EP-0768041 that is prepared in water-bearing media prepare APM.Ace, acquisition has good especially thermostability, extremely low residual water capacity and extremely low hygroscopic APM.Ace also have simultaneously at elevated temperatures with dried forms and reduce the danger that forms 3A when long time stored greatly.
So the method according to this invention, a kind of stable increase is provided, especially is exposed to the condition of the temperature of rising for a long time, promptly 80 ℃ at the APM.Ace that relates to dried forms, under 48 hours, the APM.Ace of the new improved form that stability increases in the time of may forming 3A.In the APM.Ace of this new improved form, the content of 3A keeps below the limit of detection based on the 10ppm of APM.Ace dry weight when described the exposure.
Therefore, this new APM.Ace is characterised in that under 80 ℃ of temperature, and in the time of 48 hours, its acetoacetyl amine content keeps below 10ppm with respect to the dry weight of APM.Ace with the APM.Ace heating of dried forms.Other character of APM.Ace are corresponding to the character of the product that obtains among the APM.Ace preparation method who used before the present invention.This new product itself is only forming the product that is different from prior art aspect 3A dangerous.
With reference to following embodiment and comparing embodiment explanation the present invention.Embodiment never limits the present invention.
Use HPLC (high performance liquid chromatography) technology to carry out all analyses, particularly gradient elution method.Volume injected under all situations is 250 microlitres; Total operating time is 50 minutes, and flow velocity is 1.5ml/ minute.
Equipment: the thermostatic control column oven is set to 20 ℃ (Hewlett Packard HP1090); Column length 250mm, internal diameter 4mm is filled with LiChrospher 100 RP-18 (5 micron particle; Merck); (Spectra physics, Spectra200), 300nm UV detects variable-wavelenght detector.The limit of detection of 3A is about 10ppm (with respect to the dry weight of exsiccant APM.Ace).
Moving phase: from following component, promptly;
(1) redistilled water
(2) methyl alcohol, HPLC level (Chromasolv; Riedel de Haen 34860)
(3) tetrabutylammonium Hydroxysulfate (TBAHS); Fluka 86875
(4) 0.1M potassium hydroxide aqueous solution,
Prepare three kinds of solvents (C), it has following component for A, B:
| Component | Solvent orange 2 A | Solvent B | Solvent C |
| ????(1) | ????2000ml | ????1800ml | ????2000ml |
| ????(2) | ????200ml | ||
| ????(3) | ????6.8g | ????6.8g | ????6.8g |
| ????(4) | ????5.6g |
The use gradient is as follows:
| Time (minute) | Solvent orange 2 A (%) | Solvent B (%) | Solvent C (%) |
| ????0 | ????40 | ????10 | ????50 |
| ????16 | ????20 | ????30 | ????50 |
| ????18 | ????50 | ????50 | |
| ????33 | ????50 | ????50 | |
| ????35 | ????40 | ????10 | ????50 |
ROSS is equipped with in use
The KnickPortamess752 Calimatic pH meter of Combination pH electrode 8155SC carries out the mensuration of pH value.
The embodiment I
Component below in case temperature is 1 liter of crystallizer of 50 ℃, mixing: 466g softening water, (0.21 mole of 141g AceK (0.70 mole) and 65g APM; Water capacity 4%).Then using transfer pipet to drip 33% aqueous hydrochloric acid in 25 minutes is 3.5 until pH.Subsequently, added 5g APM (add 150g altogether in addition, or 0.49 mole) in per 5 minutes, pH is controlled to be 3.5 by other dripping hydrochloric acid solution.After adding all APM, add 33% hydrochloric acid of last amount, added the hydrochloric acid of 77g 33% (0.70 mole) altogether like this.The experiment beginning began to cool down (cryostat is 10 ℃) after 3 hours.Cool off after 3 hours, obtain the 716g slurry altogether.With wall temperature is that 10 ℃ refrigerative B ü chner funnel filters slurry, and then washed twice is used the softening water of 10 ℃ of 180ml at every turn, by solid KOH its pH is risen to 11.0.The water capacity of the wet piece of collecting is 19.2 wt.%.Under 50 ℃, the piece drying that in fluidized-bed, will wet 1 hour.Dry back water capacity is less than 0.1 wt.%.Susceptible of proof does not have aceto-acetamide (3A) in this product.
Desciccate was kept 48 hours for 80 ℃, after this, measure 3A content once more.Still 3A fails to detect.After 60 ℃ of 13 weeks of storage, fail to detect 3A.Store after 1 year for 60 ℃, still fail to detect 3A.
Comparative Example A An
In 25 liters of crystallizers of 20 ℃ of wall temperatures, add 20 liters of softening waters, and to wherein adding 6.03kg AceK (30 moles).The shell temperature of thermostat container is set to 50 ℃, and the temperature of crystallizer raises gradually in experiment like this.In addition, in 2 minutes, stir (10 moles of adding 3.07 kg APM; Water capacity 4%).During whole adding APM, add 33% hydrochloric acid soln with the speed of 35g/min.After 9 minutes, can not the restir reaction mixture, after this, add 5kg water in addition.After 10 minutes, but the restir mixture.After other 10 minutes, add 500gAPM.Then added a 500g APM in 20 minutes in per 5 minutes.Along with reaction mixture multiviscosisty once more, stopped to add APM in 15 minutes.Then, add a 500g APM in per 5 minutes in 30 minutes, then add last a 630g APM.The total amount of the APM that adds is 9.2kg (30 moles), and the total amount of the hydrochloric acid soln of adding is 3.3kg (30 moles).Subsequently, thermostat container is set to 10 ℃.Cool off after 3 hours, mould temperature is 22.8 ℃, lifts away from heart slurry with every part 3.Every part of washed twice is used 20 ℃ of softening waters of 300ml at every turn.The water capacity of the wet piece of collecting is 5.7 wt.%.Under 50 ℃, with low rate (about 70rpm) dry 3 hours of the piece that in the vane-type moisture eliminator, will wet.Obtaining total amount is 12.25kg exsiccant APM.Ace.Dried water capacity is less than 0.1wt.%.In this product, fail to detect the existence of aceto-acetamide (3A).
Desciccate was kept 48 hours for 80 ℃, after this, measure 3A content once more.At this moment, the content of 3A is 17ppm
After 40 ℃ in exsiccant APM.Ace blade stored for 14 weeks, in product, fail to detect 3A.
After 1 month, discovery 3A is 17ppm with 60 ℃ of storages of dry APM.Ace.After 60 ℃ of 13 weeks of storage, the concentration of 3A increases to 32ppm.
Claims (9)
1. thereby one kind is separated method with the salt of the isolated in form of wet solid product and aspartame that subsequent drying prepares solid and dried forms and acesulfame acid by preparation in liquid medium and by solids liq, before being characterised in that drying, described wet solid product is carried out the washing operation of one or more steps, and wherein last washing operation carries out by means of pH8 or higher alkaline aqueous solution at least.
2. according to the method for claim 1, be characterised in that this alkaline aqueous solution is sodium hydroxide and/or potassium hydroxide solution.
3. according to the method for claim 1 or 2, be characterised in that alkaline aqueous solution pH scope is that 8-13, especially scope are about 10.5-about 11.5.
4. according to each method of claim 1-3, be characterised in that the temperature of alkaline aqueous solution is not higher than 20 ℃, especially 15-5 ℃ scope.
5. according to each method of claim 1-4, be characterised in that washing operation carries out not being higher than under 20 ℃ the temperature, especially be 15-5 ℃ scope.
6. according to each method of claim 1-5, be characterised in that the salt with aspartame and acesulfame acid contacts the several seconds at least with alkaline aqueous solution, preferred 2-20 minute.
7. according to each method of claim 1-6, be characterised in that before using alkaline aqueous solution to carry out washing operation, at first carry out at least water washing.
8. according to each method of claim 1-7, be characterised in that use is with respect to the amount (with dry weight basis) of the APM.Ace alkaline aqueous solution of 10wt.% at least.
9. the aspartame that increases of stability and the salt of acesulfame acid were characterised in that under 80 ℃ described salt heating with dried forms after 48 hours, kept below 10ppm with respect to the content of the dry weight aceto-acetamide of salt.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL1009324 | 1998-06-05 | ||
| NL1009324A NL1009324C2 (en) | 1998-06-05 | 1998-06-05 | Preparation and purification of an organic salt of aspartame. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1304414A true CN1304414A (en) | 2001-07-18 |
Family
ID=19767258
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN99807046A Pending CN1304414A (en) | 1998-06-05 | 1999-06-01 | Preparation of organic salt of aspartame |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP1084139A1 (en) |
| JP (1) | JP2002517510A (en) |
| KR (1) | KR20010052585A (en) |
| CN (1) | CN1304414A (en) |
| AU (1) | AU4173799A (en) |
| NL (1) | NL1009324C2 (en) |
| WO (1) | WO1999064444A1 (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10120413A1 (en) * | 2001-04-26 | 2002-10-31 | Nutrinova Gmbh | Acesulfame salt, process for its preparation and its use |
| DE10330025A1 (en) * | 2003-07-03 | 2005-01-20 | Nutrinova Nutrition Specialties & Food Ingredients Gmbh | Process for the preparation of a sweetener salt based on aspartame and acesulfame |
| CN104292181B (en) * | 2014-09-27 | 2016-10-26 | 安徽金禾实业股份有限公司 | A kind of MVR system concentrates the method for acesulfame potassium mother solution |
| RS59840B1 (en) | 2016-09-21 | 2020-02-28 | Celanese Int Corp | Acesulfame potassium compositions and processes for producing same |
| DK3319948T3 (en) | 2016-09-21 | 2021-09-27 | Celanese Int Corp | Acesulfame-potassium compositions and methods for their preparation |
| JP6912582B2 (en) | 2016-09-21 | 2021-08-04 | セラニーズ・インターナショナル・コーポレーション | Acesulfame potassium composition and its production method |
| SI3319949T1 (en) | 2016-09-21 | 2020-11-30 | Celanese International Corporation, | Acesulfame potassium compositions and processes for producing same |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE1009660A3 (en) * | 1995-10-11 | 1997-06-03 | Holland Sweetener Co | Sweetener salts. |
| NL1006243C2 (en) * | 1997-06-06 | 1998-12-08 | Holland Sweetener Co | Process for the preparation of salts of aspartame from N-protected aspartame. |
-
1998
- 1998-06-05 NL NL1009324A patent/NL1009324C2/en not_active IP Right Cessation
-
1999
- 1999-06-01 EP EP99925471A patent/EP1084139A1/en not_active Withdrawn
- 1999-06-01 JP JP2000553452A patent/JP2002517510A/en active Pending
- 1999-06-01 WO PCT/NL1999/000338 patent/WO1999064444A1/en not_active Application Discontinuation
- 1999-06-01 CN CN99807046A patent/CN1304414A/en active Pending
- 1999-06-01 AU AU41737/99A patent/AU4173799A/en not_active Abandoned
- 1999-06-01 KR KR1020007013766A patent/KR20010052585A/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NL1009324C2 (en) | 1999-12-07 |
| JP2002517510A (en) | 2002-06-18 |
| KR20010052585A (en) | 2001-06-25 |
| EP1084139A1 (en) | 2001-03-21 |
| AU4173799A (en) | 1999-12-30 |
| WO1999064444A1 (en) | 1999-12-16 |
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