RU96123230A - Способ получения производного аспартама, пригодного в качестве подслащивающего средства - Google Patents
Способ получения производного аспартама, пригодного в качестве подслащивающего средстваInfo
- Publication number
- RU96123230A RU96123230A RU96123230/04A RU96123230A RU96123230A RU 96123230 A RU96123230 A RU 96123230A RU 96123230/04 A RU96123230/04 A RU 96123230/04A RU 96123230 A RU96123230 A RU 96123230A RU 96123230 A RU96123230 A RU 96123230A
- Authority
- RU
- Russia
- Prior art keywords
- palladium
- platinum
- activated carbon
- solution
- obtaining
- Prior art date
Links
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 6
- LTNUSYNQZJZUSY-UHFFFAOYSA-N 3,3-dimethylbutanal Chemical compound CC(C)(C)CC=O LTNUSYNQZJZUSY-UHFFFAOYSA-N 0.000 claims 3
- IAOZJIPTCAWIRG-QWRGUYRKSA-N Aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 claims 3
- 229960003438 Aspartame Drugs 0.000 claims 3
- 108010011485 Aspartame Proteins 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 239000000605 aspartame Substances 0.000 claims 3
- 235000010357 aspartame Nutrition 0.000 claims 3
- 238000005984 hydrogenation reaction Methods 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- -1 3,3-dimethylbutyl Chemical group 0.000 claims 1
- 230000001476 alcoholic Effects 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 229910052697 platinum Inorganic materials 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
Claims (8)
1. Способ получения сложного метилового эфира N-[N-(3,3-диметилбутил)-Lαаспартил]-L-фенилаланина формулы (I):
отличающийся тем, что раствор аспартама и 3,3-диметил-бутиральдегида при комнатной температуре обрабатывают водородом при относительном давлении, равном или ниже 1 бар (0,1 МПа), в присутствии катализатора на основе платины или палладия.
отличающийся тем, что раствор аспартама и 3,3-диметил-бутиральдегида при комнатной температуре обрабатывают водородом при относительном давлении, равном или ниже 1 бар (0,1 МПа), в присутствии катализатора на основе платины или палладия.
2. Способ по п.1, отличающийся тем, что катализатор выбирают из группы, состоящей из платины на активном угле, палладия на активном угле, платиновой черни и палладиевой черни.
3. Способ по п.1, отличающийся тем, что гидрирование осуществляют в присутствии 5%-ной платины на активном угле, при относительном давлении 1 бар.
4. Способ по п.1, отличающийся тем, что гидрирование осуществляют в присутствии 10%-ного палладия на активном угле, при относительном давлении 1 бар или при атмосферном давлении.
5. Способ по п.1, отличающийся тем, что гидрирование осуществляют в присутствии платиновой черни или палладиевой черни, при атмосферном давлении.
6. Способ по п.1, отличающийся тем, что раствор аспартама и 3,3-диметил-бутиральдегида представляет собой водно-спиртовой раствор с pH 4,5 - 5, получаемый путем смешения 0,1 М раствора уксусной кислоты с метанолом.
7. Способ по пп.1 - 6, отличающийся тем, что концентрация аспартама в водно-спиртовом растворителе составляет 50 - 60 г/л, а концентрация 3,3-диметилбутиральдегида составляет 20 - 30 г/л.
8. Способ по пп.1 - 7, отличающийся тем, что полученный продукт очищают путем осаждения и отфильтровывания, после удаления в вакууме спиртовой части растворителя.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9405674 | 1994-05-09 | ||
| FR9405674A FR2719590B1 (fr) | 1994-05-09 | 1994-05-09 | Procédé perfectionné de préparation d'un composé dérivé de l'aspartame utile comme agent édulcorant. |
| PCT/FR1995/000589 WO1995030689A1 (fr) | 1994-05-09 | 1995-05-05 | Procede perfectionne de preparation d'un compose derive de l'aspartame utile comme agent edulcorant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU96123230A true RU96123230A (ru) | 1999-02-20 |
| RU2138510C1 RU2138510C1 (ru) | 1999-09-27 |
Family
ID=9463024
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU96123230A RU2138510C1 (ru) | 1994-05-09 | 1995-05-05 | Способ получения производного аспартама, пригодного в качестве подслащивающего средства |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US5510508A (ru) |
| EP (1) | EP0759031B1 (ru) |
| JP (1) | JP3303921B2 (ru) |
| KR (1) | KR100304320B1 (ru) |
| CN (1) | CN1114615C (ru) |
| AT (1) | ATE169636T1 (ru) |
| AU (1) | AU681523B2 (ru) |
| BG (1) | BG62813B1 (ru) |
| BR (1) | BR9507635A (ru) |
| CA (1) | CA2187901C (ru) |
| CZ (1) | CZ285612B6 (ru) |
| DE (1) | DE69504059T2 (ru) |
| DK (1) | DK0759031T3 (ru) |
| EE (1) | EE03402B1 (ru) |
| ES (1) | ES2122610T3 (ru) |
| FI (1) | FI114313B (ru) |
| FR (1) | FR2719590B1 (ru) |
| GE (1) | GEP19991647B (ru) |
| HK (1) | HK1012406A1 (ru) |
| HU (1) | HU219829B (ru) |
| MD (1) | MD1175G2 (ru) |
| NO (1) | NO313832B1 (ru) |
| NZ (1) | NZ285777A (ru) |
| OA (1) | OA10334A (ru) |
| PL (1) | PL180471B1 (ru) |
| RO (1) | RO115732B1 (ru) |
| RU (1) | RU2138510C1 (ru) |
| SK (1) | SK280376B6 (ru) |
| UA (1) | UA41403C2 (ru) |
| WO (1) | WO1995030689A1 (ru) |
Families Citing this family (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2719591B1 (fr) * | 1994-05-09 | 1996-07-26 | Claude Nofre | Nouveau composé utile comme agent édulcorant, son procédé de préparation. |
| FR2744454B1 (fr) * | 1996-02-07 | 1998-04-24 | Nofre Claude | Acide n-(3,3-dimethylbutyl)-l-aspartyl-d-alpha- aminoalcanoique n-(s)-1-phenyl-1-alcanamide utile comme agent edulcorant |
| US5728862A (en) * | 1997-01-29 | 1998-03-17 | The Nutrasweet Company | Method for preparing and purifying an N-alkylated aspartame derivative |
| US5770775A (en) * | 1997-02-10 | 1998-06-23 | The Nutrasweet Company | Method for preparing 3,3-dimethylbutyraldehyde |
| US5973209A (en) * | 1997-07-11 | 1999-10-26 | The Nutrasweet Company | Method for preparing 3, 3-dimethybutyraldehyde |
| US6146680A (en) * | 1997-09-11 | 2000-11-14 | The Nutrasweet Company | Metal complexes of N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester |
| US6291004B1 (en) | 1997-09-11 | 2001-09-18 | The Nutrasweet Company | Basic salts of n-[n-(3,3-dimethylbutyl)-l-α-aspartyl]-l-phenylalanine 1-methyl ester |
| US6180156B1 (en) | 1997-09-11 | 2001-01-30 | The Nutrasweet Company | Acid salts of N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester |
| US6129942A (en) * | 1997-09-11 | 2000-10-10 | The Nutrasweet Company | Sweetener salts of N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester |
| JPH1180108A (ja) * | 1997-09-12 | 1999-03-26 | Ajinomoto Co Inc | 甘味料の精製法 |
| JPH11130794A (ja) * | 1997-10-23 | 1999-05-18 | Ajinomoto Co Inc | アスパルテーム誘導体の精製方法 |
| JPH11171895A (ja) * | 1997-12-11 | 1999-06-29 | Ajinomoto Co Inc | アスパルテームとアスパルテーム誘導体の分離精製方法 |
| JPH11169132A (ja) * | 1997-12-15 | 1999-06-29 | Ajinomoto Co Inc | アスパルテームとアスパルテーム誘導体の混晶及びその製造方法 |
| JPH11169133A (ja) * | 1997-12-15 | 1999-06-29 | Ajinomoto Co Inc | アスパルテーム及びアスパルテーム誘導体を含有する甘味料組成物 |
| AU1936499A (en) * | 1997-12-17 | 1999-07-05 | Nutrasweet Company, The | Use of n-{n-(3,3-dimethylbutyl)-l-alpha-aspartyl}-l-phenylalanine 1-methyl esterin dairy and dairy analogue products |
| AU1924899A (en) * | 1997-12-17 | 1999-07-05 | Nutrasweet Company, The | Tabletop sweetener compositions comprising sweetener with extremely high potency |
| AR014129A1 (es) * | 1997-12-17 | 2001-02-07 | Nutrasweet Co | Bebida que comprende fundamentalmente un ester n-[n-(3,3-dimetilbutil)-l- alfa-aspartil]-l-fenilamina 1 - metilico, bebida sin alcohol carbonatada,bebida de jugo, bebida envasada caliente y bebida deportiva de bajas calorias. |
| JPH11322788A (ja) * | 1998-05-08 | 1999-11-24 | Ajinomoto Co Inc | 新規アスパルテーム誘導体結晶及びその製造方法 |
| JP2000026496A (ja) | 1998-05-08 | 2000-01-25 | Ajinomoto Co Inc | 新規アスパルテーム誘導体結晶及びその製造法 |
| US5905175A (en) * | 1998-05-20 | 1999-05-18 | The Nutrasweet Company | Synthesis and purification of 3,3-dimethylbutyraldehyde via oxidation of 1-chloro-3,3-dimethylbutane with dimethyl sulfoxide |
| US6692778B2 (en) * | 1998-06-05 | 2004-02-17 | Wm. Wrigley Jr. Company | Method of controlling release of N-substituted derivatives of aspartame in chewing gum |
| AU7822398A (en) * | 1998-06-05 | 1999-12-20 | Wm. Wrigley Jr. Company | Method of controlling release of n-substituted derivatives of aspartame in chewing gum and gum produced thereby |
| AU752473B2 (en) * | 1998-06-26 | 2002-09-19 | Ajinomoto Co., Inc. | Novel aspartyl dipeptide ester derivatives and sweeteners |
| US5977415A (en) * | 1998-08-20 | 1999-11-02 | The Nutrasweet Company | Preparation of 3, 3-dimethylbutyraldehyde from a tert-butyl cation precursor, vinyl chloride and an acidic catalyst |
| NL1010063C2 (nl) * | 1998-09-10 | 2000-03-13 | Holland Sweetener Co | Werkwijze voor de bereiding van neotaam. |
| US5994593A (en) * | 1998-09-17 | 1999-11-30 | The Nutrasweet Company | Synthesis and purification of 3,3-dimethylbutyraldehyde via hydrolysis of 1,1-dichloro-3,3-dimethylbutane or 1-bromo-1-chloro-3,3-dimethylbutane |
| US6214402B1 (en) | 1998-09-17 | 2001-04-10 | The Nutrasweet Company | Co-crystallization of sugar and n-[n-(3,3-dimethylbutyl)-l αaspartyl]-l-phenylalanine 1-methyl ester |
| CA2348162A1 (en) * | 1998-10-30 | 2000-05-11 | Ajinomoto Co., Inc. | Method for preparing crystal of aspartame derivative excellent in stability |
| US6844465B2 (en) | 1998-10-30 | 2005-01-18 | Ajinomoto Co., Inc. | Method for preparing highly stable crystals of aspartame derivative |
| KR20010075419A (ko) | 1998-10-30 | 2001-08-09 | 에가시라 구니오 | 안정성이 우수한 아스파르탐 유도체 결정의 결정 석출법 |
| US6465677B1 (en) | 1998-11-19 | 2002-10-15 | The Nutrasweet Company | Method for the preparation of N-neohexyl-α-aspartyl-L-phenylalanine methyl ester from imidazolidin-4-one intermediates |
| AU1628700A (en) * | 1998-11-20 | 2000-06-13 | Nutrasweet Company, The | Amorphous N-(N-(3,3-dimethylbutyl)-l-alpha-aspartyl)-l-phenylalanine 1-methyl ester |
| WO2000032622A1 (en) | 1998-11-25 | 2000-06-08 | The Nutrasweet Company | PURIFICATION OF N-[N-(3,3-DIMETHYLBUTYL)-L-α-ASPARTYL]-L-PHENYLALANINE 1-METHYL ESTER VIA CRYSTALLIZATION |
| WO2000036924A1 (en) * | 1998-12-18 | 2000-06-29 | The Nutrasweet Company | N-[N-(3,3-DIMETHYLBUTYL)-L-α-ASPARTYL]-L-PHENYLALANINE 1-METHYL ESTER AS A SWEETENER IN CHEWING GUM |
| US6077962A (en) * | 1998-12-24 | 2000-06-20 | The Nutrasweet Company | N-3, 3-dimethylbutyl-L-aspartic acid and esters thereof, the process of preparing the same, and the process for preparing N-(N-(3,3-dimethylbutyl) -α L-aspartyl)-L- phenylalanine 1-methyl ester therefrom |
| US6048999A (en) * | 1999-01-25 | 2000-04-11 | The Nutrasweet Company | N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester synergistic sweetener blends |
| US6180157B1 (en) | 1999-02-18 | 2001-01-30 | The Nutrasweet Company | Process for preparing an N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester agglomerate |
| EP1164872A1 (en) | 1999-03-26 | 2002-01-02 | The NutraSweet Company | PARTICLES OF N- N-(3,3-DIMETHYLBUTYL)-L-$g(a)-ASPARTYL]-L-PHENYLALANINE 1-METHYL ESTER |
| US6726922B1 (en) | 1999-06-28 | 2004-04-27 | Minu, L.L.C. | Process and composition for temporarily suppressing pain |
| US6573409B1 (en) * | 1999-07-02 | 2003-06-03 | The Nutrasweet Company | Process for the preparation of 3,3-dimethylbutanal |
| AU4459400A (en) | 1999-07-28 | 2001-02-19 | Nutrasweet Company, The | A method for the purification of n-[n-(3,3-dimethylbutyl)-l-alpha-aspartyl]-l-phenylalanine 1-methyl ester |
| AU7627800A (en) | 1999-08-06 | 2001-03-05 | Nutrasweet Company, The | Process for coating n-[n-(3,3-dimethylbutyl)-l-alpha-aspartyl]-l-phenylalanine 1-methyl ester onto a carrier |
| WO2001010236A1 (en) * | 1999-08-11 | 2001-02-15 | The Nutrasweet Company | CONFECTIONERY FOOD PRODUCTS SWEETENED WITH N-[N-(3,3-DIMETHYLBUTYL)-1-α-ASPARTYL]-L-PHENYLALANINE METHYL ESTER |
| AU6727300A (en) * | 1999-09-07 | 2001-04-10 | Ajinomoto Co., Inc. | Process for producing aspartame derivative, method of purifying the same, crystals thereof and use of the same |
| KR20020038797A (ko) * | 1999-10-08 | 2002-05-23 | 에가시라 구니오 | 아스파탐 유도체의 제조방법, 이의 결정, 이를 위한신규한 제조 중간체 및 당해 중간체의 제조방법 |
| US6627431B1 (en) | 2000-05-12 | 2003-09-30 | The Nutrasweet Company | Chemoenzymatic synthesis of neotame |
| EP1403276B1 (en) * | 2000-05-18 | 2005-11-16 | The NutraSweet Company | Synthesis of N-[N-(3,3-dimethylbutyl)-L-alpha-aspartyl]-L-phenylalanine 1-methyl ester using L-alpha-aspartyl-L-phenylalanine 1-methyl ester precursors |
| WO2001087927A2 (en) * | 2000-05-18 | 2001-11-22 | The Nutrasweet Company | gYNTHESIS OF N-[N-(3,3-DIMETHYLBUTYL)-L-α-ASPARTYL]-L-PHENYLALANINE 1-METHYL ESTER USING L-α-ASPARTYL-L-PHENYLALANINE 1-METHYL ESTER PRECURSORS |
| ES2233647T3 (es) * | 2000-05-19 | 2005-06-16 | The Nutrasweet Company | Sintesis de n- n-(3,3-dimetilbutil)-l-alfa- aspartil-l- fenilalanina 1-metil ester utilizando "nuevos derivados de laoxazolidinona". |
| US7326430B2 (en) * | 2000-07-18 | 2008-02-05 | The Nutrasweet Company | Method of preparing liquid compositions for delivery of N-[N- (3,3-dimethylbutyl-L-α-aspartyl]-L-phenylalanine 1-methyl ester in food and beverage systems |
| WO2002065853A2 (en) * | 2000-11-06 | 2002-08-29 | The Nutrasweet Company | Catalyst modification to enhance neotame production |
| CN100482681C (zh) * | 2003-05-06 | 2009-04-29 | 纽特拉斯威特公司 | 使用3,3-二甲基丁醛前体合成N-[N-(3,3-二甲基丁基)-L-α-天冬氨酰基]-L-苯基丙氨酸1-甲基酯的方法 |
| CA2558683A1 (en) * | 2004-03-05 | 2005-09-22 | Sunil Srivastava | High-intensity sweetener-polyol compositions |
| US20060188629A1 (en) * | 2005-01-21 | 2006-08-24 | Greg Liesen | Method for the purification of sucralose |
| EP1971217A2 (en) * | 2005-12-02 | 2008-09-24 | The Coca-Cola Company | Reduced calorie frozen beverage |
| CN101270092B (zh) * | 2008-04-30 | 2010-12-08 | 厦门大学 | 一种合成纽甜的方法 |
| US20100125146A1 (en) * | 2008-11-19 | 2010-05-20 | Johnson Matthey Public Limited Company | Method for making pharmaceutical compounds |
| CN105131081A (zh) * | 2015-09-08 | 2015-12-09 | 南京工业大学 | 一种廉价高效的纽甜制备方法 |
| FR3102041A1 (fr) | 2019-10-22 | 2021-04-23 | Aroma Sens | Edulcorant pour liquides de cigarette électronique |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2533210A1 (fr) * | 1982-09-17 | 1984-03-23 | Lyon I Universite Claude | Edulcorants de synthese |
| FR2630304B1 (fr) * | 1988-04-22 | 1990-08-31 | Bernard Lyon I Universite Clau | Derives n-hydrocarbones des acides aspartique et glutamique alpha-monoamides utiles comme agents edulcorants |
| FR2697844B1 (fr) * | 1992-11-12 | 1995-01-27 | Claude Nofre | Nouveaux composés dérivés de dipeptides ou d'analogues dipeptidiques utiles comme agents édulcorants, leur procédé de préparation. |
-
1994
- 1994-05-09 FR FR9405674A patent/FR2719590B1/fr not_active Expired - Lifetime
-
1995
- 1995-05-05 AT AT95919484T patent/ATE169636T1/de active
- 1995-05-05 CZ CZ963299A patent/CZ285612B6/cs not_active IP Right Cessation
- 1995-05-05 EP EP95919484A patent/EP0759031B1/fr not_active Expired - Lifetime
- 1995-05-05 RO RO96-02111A patent/RO115732B1/ro unknown
- 1995-05-05 KR KR1019960706255A patent/KR100304320B1/ko not_active IP Right Cessation
- 1995-05-05 NZ NZ285777A patent/NZ285777A/en not_active IP Right Cessation
- 1995-05-05 MD MD96-0387A patent/MD1175G2/ru not_active IP Right Cessation
- 1995-05-05 GE GEAP19953483A patent/GEP19991647B/en unknown
- 1995-05-05 ES ES95919484T patent/ES2122610T3/es not_active Expired - Lifetime
- 1995-05-05 AU AU25285/95A patent/AU681523B2/en not_active Expired
- 1995-05-05 EE EE9600179A patent/EE03402B1/xx unknown
- 1995-05-05 UA UA96114348A patent/UA41403C2/ru unknown
- 1995-05-05 JP JP52872695A patent/JP3303921B2/ja not_active Expired - Fee Related
- 1995-05-05 DE DE69504059T patent/DE69504059T2/de not_active Expired - Lifetime
- 1995-05-05 PL PL95317053A patent/PL180471B1/pl not_active IP Right Cessation
- 1995-05-05 CN CN95192973A patent/CN1114615C/zh not_active Expired - Lifetime
- 1995-05-05 WO PCT/FR1995/000589 patent/WO1995030689A1/fr active IP Right Grant
- 1995-05-05 DK DK95919484T patent/DK0759031T3/da active
- 1995-05-05 HU HU9602990A patent/HU219829B/hu not_active IP Right Cessation
- 1995-05-05 CA CA002187901A patent/CA2187901C/en not_active Expired - Fee Related
- 1995-05-05 SK SK1449-96A patent/SK280376B6/sk not_active IP Right Cessation
- 1995-05-05 BR BR9507635A patent/BR9507635A/pt not_active Application Discontinuation
- 1995-05-05 RU RU96123230A patent/RU2138510C1/ru not_active IP Right Cessation
- 1995-05-08 US US08/436,576 patent/US5510508A/en not_active Expired - Lifetime
-
1996
- 1996-10-14 FI FI964106A patent/FI114313B/fi not_active IP Right Cessation
- 1996-10-29 OA OA60912A patent/OA10334A/fr unknown
- 1996-11-08 BG BG100967A patent/BG62813B1/bg unknown
- 1996-11-08 NO NO19964745A patent/NO313832B1/no not_active IP Right Cessation
-
1998
- 1998-12-16 HK HK98113669A patent/HK1012406A1/xx not_active IP Right Cessation
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