CN110563797A - Method for removing viscous components in neotame - Google Patents
Method for removing viscous components in neotame Download PDFInfo
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- CN110563797A CN110563797A CN201910967803.7A CN201910967803A CN110563797A CN 110563797 A CN110563797 A CN 110563797A CN 201910967803 A CN201910967803 A CN 201910967803A CN 110563797 A CN110563797 A CN 110563797A
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- China
- Prior art keywords
- neotame
- crystallization
- solution
- temperature
- stirring
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- 239000004384 Neotame Substances 0.000 title claims abstract description 51
- HLIAVLHNDJUHFG-HOTGVXAUSA-N neotame Chemical compound CC(C)(C)CCN[C@@H](CC(O)=O)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 HLIAVLHNDJUHFG-HOTGVXAUSA-N 0.000 title claims abstract description 51
- 235000019412 neotame Nutrition 0.000 title claims abstract description 51
- 108010070257 neotame Proteins 0.000 title claims abstract description 51
- 238000000034 method Methods 0.000 title claims abstract description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 27
- 238000002425 crystallisation Methods 0.000 claims abstract description 20
- 230000008025 crystallization Effects 0.000 claims abstract description 20
- 239000008213 purified water Substances 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000003756 stirring Methods 0.000 claims abstract description 8
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 6
- 150000007529 inorganic bases Chemical class 0.000 claims abstract description 5
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 5
- 238000000926 separation method Methods 0.000 claims abstract description 5
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000011345 viscous material Substances 0.000 abstract description 6
- 230000008569 process Effects 0.000 abstract description 5
- 238000005119 centrifugation Methods 0.000 abstract description 3
- 230000002035 prolonged effect Effects 0.000 abstract description 3
- 239000007788 liquid Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 230000001953 sensory effect Effects 0.000 description 4
- 238000005054 agglomeration Methods 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 150000003839 salts Chemical group 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 150000001413 amino acids Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000003765 sweetening agent Substances 0.000 description 2
- -1 3, 3-dimethylbutyl Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000010413 mother solution Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
the invention belongs to the technical field of neotame products, and particularly relates to a method for removing viscous components in neotame. Dissolving neotame in a system of purified water and methanol, and heating to dissolve neotame; adding inorganic base, stirring, and controlling the pH value of the solution to be 9-10; then adding inorganic acid to adjust the pH value of the solution to 6.0-8.0 for neutralization; and standing for crystallization, and performing centrifugal separation to obtain the neotame with the viscosity components removed. The method for removing the viscous components in the neotame has the advantages of reasonable process, simple steps and easy realization, the content of the viscous substances of the neotame obtained by treatment and centrifugation is obviously reduced and is lower than the traditional content by 0.1 percent, and the quality guarantee period of the neotame product is obviously prolonged.
Description
Technical Field
The invention belongs to the technical field of neotame products, and particularly relates to a method for removing viscous components in neotame.
Background
Neotame (N- [ N- (3, 3-dimethylbutyl) -L-alpha-aspartic acid ] -L-phenylalanine-1-methyl ester) is a high-potency sweetener developed by Neutravist, USA, and has the advantages of high sweetness, low calorie, high stability and the like, and the potential of neotame as a good sweetener is gradually discovered along with the further application.
however, in the process of storing the neotame product, the phenomenon that the neotame product is easy to generate bonding blocks is a ubiquitous phenomenon, the storage property and the usability of the product are seriously influenced, and the further industrial development of the neotame is limited.
Disclosure of Invention
The technical problem to be solved by the invention is as follows: overcomes the defects of the prior art and provides a method for removing viscous components in neotame. The method has the advantages of reasonable process, simple steps and easy realization, the content of the neotame sticky substances obtained by treatment and centrifugation is obviously reduced and is lower than the traditional content of 0.1 percent, and the shelf life of the neotame product is obviously prolonged.
The method for removing the viscous components in the neotame comprises the following steps:
(1) dissolving neotame in a system of purified water and methanol, and heating to dissolve neotame;
(2) adding inorganic base, stirring, and controlling the pH value of the solution to be 9-10;
(3) Then adding inorganic acid to adjust the pH value of the solution to 6.0-8.0 for neutralization;
(4) And standing for crystallization, and performing centrifugal separation to obtain the neotame with the viscosity components removed.
Wherein:
The sticky substance is a product of partial hydrolysis in the neotame production process, and a small amount of this product will cause the product to become sticky and lumpy, and the content of the sticky substance is about 0.1% to 1%.
The mass ratio of the neotame to the purified water to the methanol in the step (1) is 1: 4: 0.5.
The temperature rise in the step (1) is to raise the temperature to 20-80 ℃ to melt the mixture.
The inorganic base in the step (2) is one of sodium carbonate, sodium bicarbonate or sodium hydroxide.
the stirring time in the step (2) is 0.5 to 3 hours, and the stirring temperature is 5 to 100 ℃.
The inorganic acid in the step (3) is one of hydrochloric acid, citric acid or phosphoric acid.
the crystallization temperature in the step (4) is 0-40 ℃, and the crystallization time is 12-36 hours; the rotation speed of the centrifugal machine for centrifugal separation is 1000-1200 r/min.
The reaction mechanism of the method for removing the viscous components in the neotame is as follows: the neotame has an ester structure, a small amount of hydrolysis occurs in the reaction process, the product after partial hydrolysis is an amino acid structure and has certain viscosity, the product is easy to be sticky and caked, the application performance of the product is influenced, the salt structure is formed by alkali and the amino acid structure, and the salt has high solubility in the crystallization process of the neotame, so that the salt can be dissolved in the mother solution and can be well separated from the neotame product.
Compared with the prior art, the invention has the following beneficial effects:
the method for removing the viscous components in the neotame has the advantages of reasonable process, simple steps and easy realization, the content of the viscous substances in the neotame obtained by treatment and centrifugation is obviously reduced and is lower than the traditional content by 0.1 percent, and the quality guarantee period of the neotame product is obviously prolonged.
Drawings
FIG. 1 is a high performance liquid chromatogram of neotame prepared in example 1;
FIG. 2 is a high performance liquid chromatogram of neotame prepared in example 2;
FIG. 3 is a high performance liquid chromatogram of neotame prepared in example 3;
FIG. 4 is a high performance liquid chromatogram of neotame prepared in comparative example 1.
Detailed Description
the present invention is further described below with reference to examples.
Example 1
(1) 500 g of neotame is dissolved in a system consisting of 2000 g of purified water and 250 g of methanol, and the temperature is raised to 50 ℃ to be dissolved.
(2) Sodium hydroxide was added and stirred at 70 ℃ for 1.5h, controlling the pH of the solution at 10.
(3) Hydrochloric acid was added to adjust the pH of the solution to 7.0, and neutralization was carried out.
(4) Standing for crystallization, wherein the crystallization temperature is 40 ℃, the crystallization time is 12 hours, centrifuging, the rotation speed of a centrifuge is 1200 revolutions per minute, detecting by using GB 29944-2013, and obtaining the neotame viscous substance with the content of 0 which is lower than the traditional content of 0.1% by a high performance liquid chromatogram shown in figure 1, wherein no obvious agglomeration is generated after 2 months of observation, and the sensory index is good.
Example 2
(1) 500 g of neotame is dissolved in a system consisting of 2000 g of purified water and 250 g of methanol, and the temperature is raised to 80 ℃ to be dissolved.
(2) Sodium bicarbonate was added and stirred at 95 ℃ for 1.0h, controlling the pH of the solution at 9.5.
(3) hydrochloric acid was added to adjust the pH of the solution to 8, and neutralization was carried out.
(4) Standing for crystallization, wherein the crystallization temperature is 20 ℃, the crystallization time is 24 hours, centrifuging, the rotation speed of a centrifuge is 1100 r/min, detecting by using GB 29944-2013, and obtaining the neotame viscous substance with the content of 0 which is lower than the traditional content of 0.1% by a high performance liquid chromatogram shown in figure 2, wherein no obvious agglomeration is generated after 2 months of observation, and the sensory index is good.
Example 3
(1) Neotame, 500 g, was dissolved in a system consisting of 2000 g purified water and 250 g methanol and was dissolved at 20 ℃.
(2) Sodium carbonate was added and stirred at 35 ℃ for 3h, controlling the pH of the solution to 9.
(3) hydrochloric acid was added to adjust the pH of the solution to 7.0, and neutralization was carried out.
(4) Standing for crystallization, wherein the crystallization temperature is 0 ℃, the crystallization time is 36 hours, centrifuging, the rotation speed of a centrifuge is 1200 revolutions per minute, detecting by using GB 29944-2013, and obtaining the neotame viscous substance with the content of 0 which is lower than the traditional content by 0.1% by using a high performance liquid chromatogram shown in figure 3, wherein no obvious agglomeration is generated after 2 months of observation, and the sensory index is good.
Comparative example 1
dissolving 500 g of neotame in a system consisting of 2000 g of purified water and 250 g of methanol, heating to 50 ℃, stirring for 90min to dissolve, standing for crystallization, wherein the crystallization temperature is 40 ℃, the crystallization time is 12 hours, centrifuging, the rotating speed of a centrifuge is 1200 r/min, detecting by using GB 29944-2013, and obtaining a high performance liquid chromatogram which is shown in figure 4, wherein the content of neotame viscous substances is 0.35 percent and is far higher than the traditional content by 0.1 percent, and the neotame is obviously caked after 2 months of observation and has poor sensory index.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (7)
1. A method for removing viscous components in neotame is characterized by comprising the following steps: the method comprises the following steps:
(1) Dissolving neotame in a system of purified water and methanol, and heating to dissolve neotame;
(2) adding inorganic base, stirring, and controlling the pH value of the solution to be 9-10;
(3) Then adding inorganic acid to adjust the pH value of the solution to 6.0-8.0 for neutralization;
(4) And standing for crystallization, and performing centrifugal separation to obtain the neotame with the viscosity components removed.
2. The method of claim 1, further comprising the step of: the mass ratio of the neotame to the purified water to the methanol in the step (1) is 1: 4: 0.5.
3. The method of claim 1, further comprising the step of: the temperature rise in the step (1) is to raise the temperature to 20-80 ℃ to melt the mixture.
4. The method of claim 1, further comprising the step of: the inorganic base in the step (2) is one of sodium carbonate, sodium bicarbonate or sodium hydroxide.
5. The method of claim 1, further comprising the step of: the stirring time in the step (2) is 0.5 to 3 hours, and the stirring temperature is 5 to 100 ℃.
6. the method of claim 1, further comprising the step of: the inorganic acid in the step (3) is one of hydrochloric acid, citric acid or phosphoric acid.
7. The method of claim 1, further comprising the step of: the crystallization temperature in the step (4) is 0-40 ℃, and the crystallization time is 12-36 hours; the rotation speed of the centrifugal machine for centrifugal separation is 1000-1200 r/min.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910967803.7A CN110563797A (en) | 2019-10-12 | 2019-10-12 | Method for removing viscous components in neotame |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910967803.7A CN110563797A (en) | 2019-10-12 | 2019-10-12 | Method for removing viscous components in neotame |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN110563797A true CN110563797A (en) | 2019-12-13 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910967803.7A Pending CN110563797A (en) | 2019-10-12 | 2019-10-12 | Method for removing viscous components in neotame |
Country Status (1)
| Country | Link |
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| CN (1) | CN110563797A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111704649A (en) * | 2020-08-20 | 2020-09-25 | 山东奔月生物科技股份有限公司 | Method for removing viscous substances in neotame |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5227007A (en) * | 1990-09-28 | 1993-07-13 | Kyowa Hakko Kogyo Co., Ltd. | Process for producing crystals of salt of acidic amino acid and basic amino acid |
| JPH11221100A (en) * | 1998-02-05 | 1999-08-17 | Japan Organo Co Ltd | Purification of beet sugar liquid |
| WO2000052019A2 (en) * | 1999-03-03 | 2000-09-08 | The Nutrasweet Company | Crystallization products of neotame and methods for producing same |
| US6627431B1 (en) * | 2000-05-12 | 2003-09-30 | The Nutrasweet Company | Chemoenzymatic synthesis of neotame |
| CA2657163A1 (en) * | 2009-03-02 | 2010-09-02 | Mcneil Nutritionals, Llc | Cohesive non-free flowing sweetener compositions including low-density ingredients |
| CN102863511A (en) * | 2012-09-27 | 2013-01-09 | 嘉兴百思食品科技有限公司 | Neotame preparation method |
| CN109467586A (en) * | 2018-12-15 | 2019-03-15 | 山东诚汇双达药业有限公司 | A kind of refining methd of neotame |
-
2019
- 2019-10-12 CN CN201910967803.7A patent/CN110563797A/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5227007A (en) * | 1990-09-28 | 1993-07-13 | Kyowa Hakko Kogyo Co., Ltd. | Process for producing crystals of salt of acidic amino acid and basic amino acid |
| JPH11221100A (en) * | 1998-02-05 | 1999-08-17 | Japan Organo Co Ltd | Purification of beet sugar liquid |
| WO2000052019A2 (en) * | 1999-03-03 | 2000-09-08 | The Nutrasweet Company | Crystallization products of neotame and methods for producing same |
| US6627431B1 (en) * | 2000-05-12 | 2003-09-30 | The Nutrasweet Company | Chemoenzymatic synthesis of neotame |
| CA2657163A1 (en) * | 2009-03-02 | 2010-09-02 | Mcneil Nutritionals, Llc | Cohesive non-free flowing sweetener compositions including low-density ingredients |
| CN102863511A (en) * | 2012-09-27 | 2013-01-09 | 嘉兴百思食品科技有限公司 | Neotame preparation method |
| CN109467586A (en) * | 2018-12-15 | 2019-03-15 | 山东诚汇双达药业有限公司 | A kind of refining methd of neotame |
Non-Patent Citations (2)
| Title |
|---|
| 王毛生: "各种甜味料的特性及其在焙烤食品生产中的应用", 《食品工业科技》 * |
| 邓虹: "纽甜的特性及稳定性研究", 《饲料博览》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111704649A (en) * | 2020-08-20 | 2020-09-25 | 山东奔月生物科技股份有限公司 | Method for removing viscous substances in neotame |
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Address after: No.15, Yinhai Third Road, Dongying Port Economic Development Zone, Dongying City, Shandong Province Applicant after: Shandong Benyue Biotechnology Co.,Ltd. Address before: 257453 Shandong city of Dongying province Lijin County diaokouhe resident township government Applicant before: Shandong Benyue Biotechnology Co.,Ltd. |
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Application publication date: 20191213 |