CN102718803A - Preparation method and application of N-carbamoyl-L-chromium glutamate complex - Google Patents
Preparation method and application of N-carbamoyl-L-chromium glutamate complex Download PDFInfo
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- CN102718803A CN102718803A CN2012101801690A CN201210180169A CN102718803A CN 102718803 A CN102718803 A CN 102718803A CN 2012101801690 A CN2012101801690 A CN 2012101801690A CN 201210180169 A CN201210180169 A CN 201210180169A CN 102718803 A CN102718803 A CN 102718803A
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- 229910052804 chromium Inorganic materials 0.000 title claims abstract description 47
- 239000011651 chromium Substances 0.000 title claims abstract description 47
- 238000002360 preparation method Methods 0.000 title claims abstract description 23
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 title abstract 4
- 229930195712 glutamate Natural products 0.000 title abstract 4
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- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- 238000005406 washing Methods 0.000 claims abstract description 11
- 238000001816 cooling Methods 0.000 claims abstract description 3
- 229960002989 glutamic acid Drugs 0.000 claims description 51
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 45
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- 150000003839 salts Chemical class 0.000 claims description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 6
- PHFQLYPOURZARY-UHFFFAOYSA-N chromium trinitrate Chemical compound [Cr+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PHFQLYPOURZARY-UHFFFAOYSA-N 0.000 claims description 6
- QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 claims description 6
- 229910021556 Chromium(III) chloride Inorganic materials 0.000 claims description 5
- 229960000359 chromic chloride Drugs 0.000 claims description 5
- WYYQVWLEPYFFLP-UHFFFAOYSA-K chromium(3+);triacetate Chemical compound [Cr+3].CC([O-])=O.CC([O-])=O.CC([O-])=O WYYQVWLEPYFFLP-UHFFFAOYSA-K 0.000 claims description 4
- GRWVQDDAKZFPFI-UHFFFAOYSA-H chromium(III) sulfate Chemical compound [Cr+3].[Cr+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRWVQDDAKZFPFI-UHFFFAOYSA-H 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 3
- 235000017550 sodium carbonate Nutrition 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 2
- 235000015320 potassium carbonate Nutrition 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 238000000034 method Methods 0.000 abstract description 4
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- 229940049906 glutamate Drugs 0.000 abstract 3
- 239000003674 animal food additive Substances 0.000 abstract 1
- LCQLHJZYVOQKHU-VKHMYHEASA-N carglumic acid Chemical compound NC(=O)N[C@H](C(O)=O)CCC(O)=O LCQLHJZYVOQKHU-VKHMYHEASA-N 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000000843 powder Substances 0.000 description 9
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- 238000004458 analytical method Methods 0.000 description 8
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- 239000007787 solid Substances 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
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- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 3
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- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229910021555 Chromium Chloride Inorganic materials 0.000 description 1
- 235000019750 Crude protein Nutrition 0.000 description 1
- 102000004877 Insulin Human genes 0.000 description 1
- 108090001061 Insulin Proteins 0.000 description 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
- IDSGFSCSMXRJON-UHFFFAOYSA-N N-Carbamyl-L-glutamicacid Chemical compound C1=CC([N+](=O)[O-])=CC=C1CC1=CC=CC=C1 IDSGFSCSMXRJON-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
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- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
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- FFQKYPRQEYGKAF-UHFFFAOYSA-N carbamoyl phosphate Chemical compound NC(=O)OP(O)(O)=O FFQKYPRQEYGKAF-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention discloses a preparation method and application of an N-carbamyl-L-chromium glutamate complex, which comprises the following steps: adding N-carbamoyl-L-glutamic acid into water, adjusting the pH value of the solution to 5.5-6.0, continuously adding trivalent chromium salt, reacting at 30-80 ℃ for 1-2 hours, cooling after the reaction is finished, filtering, washing and drying to obtain the N-carbamoyl-L-chromium glutamate complex. The preparation method has the advantages of simple process, high product purity, stable quality and suitability for industrial application. The obtained N-carbamyl-L-chromium glutamate complex can be used as a feed additive, and can improve the production performance and the immunity of piglets.
Description
Technical field
The present invention relates to a kind of preparation method of organic complex, be specifically related to the preparation method and the application of a kind of N-carbamyl-L-L-glutamic acid chromium complex.
Background technology
N-carbamyl-L-L-glutamic acid (N-Carbamyl-L-glutamic acid is the analog of N-acetyl-L-L-glutamic acid (NAG) NCG), and its structure is following:
N-carbamyl-L-L-glutamic acid can replace NAG to become the allosteric catalyzer of carbamylphosphate synthetase-I (GPS-I); Thereby promote proline(Pro) and Stimulina to transform to N.delta.-carbamylornithine and l-arginine; Increase arginic endogenous synthesizing, keep the balance and stability of l-arginine environment in the body.This shows that NCG stress situation have good effect for what answer between reply animal weaning period that the l-arginine deficiency causes, is a kind of potential fodder additives.
Chromium is essential trace element in the animal body, is the important component part of glucose tolerance factor (GTF).Chromium influence the metabolism of carbohydrate, fat, protein and nucleic acid through strengthening Regular Insulin physiological function in vivo, so promote animal growth, improve reproductive performance, improve carcass quality, reduce meet an urgent need, enhance immunity power.Correlative study shows that chrome uptake and its chemical species are closely related, and inorganic chromium is difficult to be absorbed; Specific absorption is merely 1% ~ 3%, and specific absorption and daily ration intake be inversely proportional to, and organic chromium is prone to be absorbed; Its specific absorption is 10% ~ 25%, and the specific absorption of different organo-chromium compounds is different.
At present, the synthetic existing report of N-carbamyl-L-L-glutamic acid is also very few about the information of synthetic its metal complex.
Summary of the invention
An object of the present invention is to provide the preparation method of a kind of N-carbamyl-L-L-glutamic acid chromium complex.
Another object of the present invention provides the application of N-carbamyl-L-L-glutamic acid chromium complex in the preparation fodder additives.
The technical scheme that the present invention adopted is:
The preparation method of N-carbamyl-L-L-glutamic acid chromium complex comprises the steps:
1) N-carbamyl-L-L-glutamic acid is added in the entry, regulator solution pH value is 5.5 ~ 6.0;
2) continue to add chromic salt, 30 ~ 80 ℃ were reacted 1~2 hour;
3) cooling is finished in reaction, filter, and washing, oven dry promptly gets N-carbamyl-L-L-glutamic acid chromium complex.
The mol ratio of chromium element is 1 ~ 2:1 in N-carbamyl-L-L-glutamic acid and the chromic salt.
Preferably, the mol ratio of chromium element is 3:2 in N-carbamyl-L-L-glutamic acid and the chromic salt.
The adding proportion of step 1) N-carbamyl-L-L-glutamic acid and water is 1mol:1000~2000ml.
Step 1) is used sodium hydroxide, yellow soda ash, Pottasium Hydroxide or salt of wormwood regulator solution pH value.
Step 2) said chromic salt is at least a in chromium sulphate, chromium trichloride, chromium nitrate, the chromium acetate.
The application of N-carbamyl-L-L-glutamic acid chromium complex in the preparation fodder additives.
Beneficial effect of the present invention is:
(1) to have a synthesis technique simple for compound method of the present invention, and product purity is higher, steady quality, and technology is convenient to advantages such as popularization;
(2) can be used as fodder additives according to the inventive method synthetic N-carbamyl-L-L-glutamic acid chromium complex, improve immunity and the production performance of animal.
Description of drawings
Fig. 1 is the infared spectrum of N-carbamyl of the present invention-L-L-glutamic acid chromium complex;
Fig. 2 is the infared spectrum of N-carboxamide-L-L-glutamic acid.
Embodiment
Below in conjunction with embodiment the present invention is further described, but is not limited thereto.
The preparation method of a kind of N-carbamyl-L-L-glutamic acid chromium complex, its step is following:
(1) 0.15molN-carboxamide-L-L-glutamic acid adds 150ml water, with about 0.3mol sodium hydrate regulator solution pH=6.0;
(2) add the 0.1mol chromium trichloride, be heated to 80 ℃ of reactions 1 hour;
(3) reaction is complete is cooled to below 50 ℃, filters, and solid is used water washing, and 105 ℃ of oven dry are pulverized, and get N-carbamyl-L-L-glutamic acid chromium complex powder 26.5g, and sample presentation carries out ultimate analysis, and chromium content is 15.22%, and nitrogen content is 12.33%.
Embodiment 2
The preparation method of a kind of N-carbamyl-L-L-glutamic acid chromium complex, its step is following:
(1) 0.15mol N-carboxamide-L-L-glutamic acid adds 200ml water, with about 0.3mol sodium hydrate regulator solution pH=5.5;
(2) add the 0.05mol chromium sulphate, be heated to 80 ℃ of reactions 2 hours;
(3) reaction is complete is cooled to below 50 ℃, filters, and solid is used water washing, and 105 ℃ of oven dry are pulverized, and get N-carbamyl-L-L-glutamic acid chromium complex powder 26.7g, and sample presentation carries out ultimate analysis, and chromium content is 15.05%, and nitrogen content is 12.26%.
Embodiment 3
The preparation method of a kind of N-carbamyl-L-L-glutamic acid chromium complex, its step is following:
(1) 0.15molN-carboxamide-L-L-glutamic acid adds 150ml water, with about 0.3mol sodium hydrate regulator solution pH=6.0;
(2) add the 0.1mol chromium nitrate, be heated to 80 ℃ of reactions 1.5 hours;
(3) reaction is complete is cooled to below 50 ℃, filters, and solid is used water washing, and 105 ℃ of oven dry are pulverized, and get N-carbamyl-L-L-glutamic acid chromium complex powder 25.8g, and sample presentation carries out ultimate analysis, and chromium content is 15.10%, and nitrogen content is 12.29%.
Embodiment 4
The preparation method of a kind of N-carbamyl-L-L-glutamic acid chromium complex, its step is following:
(1) 0.15molN-carboxamide-L-L-glutamic acid adds 200ml water, with about 0.3mol sodium hydrate regulator solution pH=6.0;
(2) add the 0.1mol chromium acetate, be heated to 80 ℃ of reactions 1 hour;
(3) reaction is complete is cooled to below 50 ℃, filters, and solid is used water washing, and 105 ℃ of oven dry are pulverized, and get N-carbamyl-L-L-glutamic acid chromium complex powder 26.1g, and sample presentation carries out ultimate analysis, and chromium content is 15.15%, and nitrogen content is 12.30%.
Embodiment 5:
The preparation method of a kind of N-carbamyl-L-L-glutamic acid chromium complex, its step is following:
(1) 0.15molN-carboxamide-L-L-glutamic acid adds 225ml water, with about 0.3mol Pottasium Hydroxide regulator solution pH=6.0;
(2) add the 0.15mol chromium trichloride, be heated to 50 ℃ of reactions 2 hours;
(3) reaction is complete is cooled to below 50 ℃, filters, and solid is used water washing, and 105 ℃ of oven dry are pulverized, and get N-carbamyl-L-L-glutamic acid chromium complex powder 28.5g, and sample presentation carries out ultimate analysis, and chromium content is 15.17%, and nitrogen content is 12.28%.
Embodiment 6:
The preparation method of a kind of N-carbamyl-L-L-glutamic acid chromium complex, its step is following:
(1) 0.2mol N-carboxamide-L-L-glutamic acid adds 200ml water, with about 0.2mol sodium carbonate regulating solution pH=6.0;
(2) add the 0.1mol chromium trichloride, be heated to 30 ℃ of reactions 2 hours;
(3) reaction is finished, and filters, and solid is used water washing, and 105 ℃ of oven dry are pulverized, and get N-carbamyl-L-L-glutamic acid chromium complex powder 27.6g, and sample presentation carries out ultimate analysis, and chromium content is 15.25%, and nitrogen content is 12.30%.
Embodiment 7:
The preparation method of a kind of N-carbamyl-L-L-glutamic acid chromium complex, its step is following:
(1) 0.1molN-carboxamide-L-L-glutamic acid adds 200ml water, with about 0.2mol sodium hydrate regulator solution pH=6.0;
(2) add the 0.1mol chromium acetate, be heated to 60 ℃ of reactions 1 hour;
(3) reaction is complete is cooled to below 50 ℃, filters, and solid is used water washing, and 105 ℃ of oven dry are pulverized, and get N-carbamyl-L-L-glutamic acid chromium complex powder 19.5g, and sample presentation carries out ultimate analysis, and chromium content is 15.16%, and nitrogen content is 12.23%.
The product that embodiment 1 obtains is used hot water injection's multipass, use absolute ethanol washing again, oven dry can get the higher N-carbamyl of purity-L-L-glutamic acid chromium complex, for the blue-greenish colour powder, is slightly soluble in water, is insoluble to ethanol, methyl alcohol, acetone and other organic solvent.Sample presentation is surveyed infrared spectrogram, and the gained collection of illustrative plates is as shown in Figure 1.The infared spectrum of corresponding N-carboxamide-L-L-glutamic acid is as shown in Figure 2.This chromium complex sample presentation carries out ultimate analysis, and Cr, C, H, N content are respectively 15.39%, 32.11%, 3.45%, 12.35%.Embodiment 2 ~ 7 products obtained therefroms are similarly the blue-greenish colour powder, are slightly soluble in water, are insoluble to ethanol, methyl alcohol, acetone and other organic solvent, and after same treatment, sample presentation detects, and infrared spectrogram is extremely similar with embodiment 1.
Experimentation on animals
1, experiment is provided with
72 close batch, body weight 35 age in days weanling pigs close, that be in a good state of health are raised a week in advance; Be divided into 9 groups at random; 7 experimental group (adding N-carbamyl-L-L-glutamic acid chromium complex 0.80ppm of embodiment 1~7 in the basal diet respectively); A negative control group (basal diet), a positive control group (basal diet adds the 1.0ppm chromium chloride), every group of 8 pigs.
This experiment is carried out in the insulation pig house, and trial period was 8 weeks.Duration of test, free choice feeding drinking-water; Natural lighting, temperature is at 22-28 ℃, and humidity is at 60-70%.The crude protein content of basal diet is 18.5%, and metabolizable energy is 3340Kcal/kg, and calcium contents is 0.7%, and available phosphorus content is 0.32%.
2, production performance test
Food consumption, diarrhea rate, the ight soil index of the every hurdle of time recording every day piglet; Measure the individual weight of each piglet weekly; Add up feedstuff-meat ratio weekly, calculate all food consumptions, day weight gain.Experiment is got blood urea nitrogen and glucose level in the blood sample measuring serum after finishing.
3, experimental result
Experimental result shows, it is higher that all add the experimental group ight soil index of N-carbamyl-L-L-glutamic acid chromium complexes, and diarrhea piglet number is all far below negative control group, and do not have significant difference between the positive control group.But the day weight gain rate of experimental group piglet all is significantly higher than positive and negative control group (P ﹤ 0.05), is illustrated in the N-carbamyl-L-L-glutamic acid chromium complex that adds 0.80ppm in the feed and can significantly improves production performance and the immune performance of piglet.
More than experiment shows that N-carbamyl-L-L-glutamic acid chromium complex can be used as fodder additives, improves the production performance of animal.
Above embodiment is merely and introduces preferred case of the present invention, and to those skilled in the art, any conspicuous variation and the improvement in the scope that does not deviate from spirit of the present invention, carried out all should be regarded as a part of the present invention.
Claims (6)
1.N-the preparation method of carbamyl-L-L-glutamic acid chromium complex comprises the steps:
1) N-carbamyl-L-L-glutamic acid is added in the entry, regulator solution pH value is 5.5 ~ 6.0;
2) continue to add chromic salt, 30 ~ 80 ℃ were reacted 1~2 hour;
3) cooling is finished in reaction, filter, and washing, oven dry promptly gets N-carbamyl-L-L-glutamic acid chromium complex.
2. preparation method according to claim 1 is characterized in that, the mol ratio of chromium element is 1 ~ 2:1 in N-carbamyl-L-L-glutamic acid and the chromic salt.
3. preparation method according to claim 1 is characterized in that, the adding proportion of step 1) N-carbamyl-L-L-glutamic acid and water is 1mol:1000~2000ml.
4. preparation method according to claim 1 is characterized in that step 1) is used sodium hydroxide, yellow soda ash, Pottasium Hydroxide or salt of wormwood regulator solution pH value.
5. preparation method according to claim 1 is characterized in that step 2) said chromic salt is at least a in chromium sulphate, chromium trichloride, chromium nitrate, the chromium acetate.
6.N-the application of carbamyl-L-L-glutamic acid chromium complex in the preparation fodder additives.
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Cited By (2)
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CN102942506A (en) * | 2012-11-16 | 2013-02-27 | 长沙道勤生物科技有限公司 | Preparation method for feed additive of N-carbamyl glutamate chelated zinc |
CN112209821A (en) * | 2020-11-05 | 2021-01-12 | 建明(中国)科技有限公司 | Preparation method of chromium propionate |
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谢文磊等,: "饲料添加剂谷氨酸铬配合物的合成研究", 《郑州粮食学院学报》 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102942506A (en) * | 2012-11-16 | 2013-02-27 | 长沙道勤生物科技有限公司 | Preparation method for feed additive of N-carbamyl glutamate chelated zinc |
CN112209821A (en) * | 2020-11-05 | 2021-01-12 | 建明(中国)科技有限公司 | Preparation method of chromium propionate |
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