CN107333975B - A kind of novel processing step of chromium picolinate based food additive - Google Patents
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- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
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Abstract
The invention discloses a kind of novel processing steps of chromium picolinate based food additive, belong to food additives synthesis technical field.A kind of chromium picolinate based food additive, has the following structure:
Description
Technical field
The invention belongs to food additives synthesis technical fields, and in particular to a kind of chromium picolinate based food additive
Novel processing step.
Background technique
Chromium is well known as a kind of necessary micronutrient of people and mammal, and trivalent chromium passes through glucose
The effect of tolerance factor (GTF) synergistic effect and the sensibility of enhancing insulin is to influence lipid, carbohydrate, protein and nucleic acid
Metabolism.Currently, trivalent Chroma-Pak has been widely used in the health care product, medicine and video of people.From in the 1990s, trivalent
Effect of the chromium in Animal nutrition gets more and more attention and pays close attention to.As nutritional additive, chromium picolinate has been obtained extensively
Application.Chromium picolinate is pyridine carboxylic acid and Cr3+Complex compound, cell membrane can be passed through and directly act on cell tissue,
Can enhance insulin active, improve human body glycometabolism, be it is a kind of it is permitted by the Ministry of Public Health, can be added in health food
Functional component.In recent years, propolis because of it with antibacterial, anti-inflammatory, antipruritic, anti-oxidant, immune, the hypoglycemic, reducing blood lipid of enhancing, anti-swell
The multiple functions such as tumor have extensive medical treatment, health-care effect to human body, it has also become emerging health care product is by high praise, in the market
Occur needing that there is the bee glue soft capsule class health food for adjusting blood glucose function, in part of bee glue soft capsule class health care product
It is added to chromium picolinate, as nutritional supplement.In addition, lot of experiments proves that chromium has the work for promoting growth of animals or poultry really
With, for example, chromium trichloride can stimulate feeding low-protein diet rat growth performance.To produce ox mend chromium, can increase feed intake and
The output of milk, while also improving butterfat, lactose and newborn total solid.Postpartum 50 days or so milk cow addition chromium can be significantly reduced
Material milk ratio.The chromic salts that doses are added in aquatic animal feed can promote the growth of juvenile fish, increase fish body weight and mention
High feed efficiency etc..It is added nicotinate chromium two months in fattening pannage, compared with the control group, adding weight is respectively increased
11.7%, 11.1% and 12.5%, feed-weight ratio has been respectively increased 5.5%, 5.6% and 4.2%.We pass through new side in laboratory
Method has synthesized a kind of new pyridine acid chromium class food additives, which has synthetic method simple, bioconcentration it is low and
The advantages that under getting fat effect.
Summary of the invention
The technical problem to be solved by the present invention is to provide it is a kind of operation is simple, raw material is cheap and easy to get, reaction efficiency compared with
A kind of novel processing step of high and reproducible chromium picolinate based food additive.
The present invention adopts the following technical scheme that solve above-mentioned technical problem, a kind of chromium picolinate based food additive
Novel processing step, it is characterised in that specific steps are as follows:
A, cyanoacetic acid reacts with ammonium hydroxide under carbonyl reduction catalyst action and generates 3- aminoacrylonitrile；
B, vinyl ethyl ether and trifluoroacetic acid generate 4- ethyoxyl -1,1,1- trifluoro under pyridine and phosphorus pentachloride effect
Butyl- 3- alkene -2- ketone；
C, 3- aminoacrylonitrile and the generation substitution reaction of 4- ethyoxyl-1,1,1- trifluoro butyl- 3- alkene-2- ketone obtain 2-(ammonia
Methylene) three fluoro- 5- oxo hex- 3- alkene nitrile hydrochloride of -6,6,6-；
D, the fluoro- 5- oxo hex- 3- alkene nitrile hydrochloride of 2-(aminomethylene)-6,6,6- three is at DCC and phosphorous acid effect
Itself cyclization obtains 6- (trifluoromethyl) nicotinic acid nitrile；
E, 6- (trifluoromethyl) nicotinic acid nitrile is oxidized to obtain 6- (trifluoromethyl) pyridine carboxylic acid；
F, 6- (trifluoromethyl) pyridine carboxylic acid reacts to obtain in ultrasound reactor with chromium trichloride
It further limits, the detailed process of step A are as follows: cyanoacetic acid and methanol are added in reaction flask, adds carbonyl
Reducing catalyst NaBH (OAc)3, nitrogen protection reaction system is slowly added dropwise ammonium hydroxide, and control temperature is no more than 60 during being added dropwise
DEG C, heating reflux reaction after completion of dropwise addition, TLC monitors raw material fully reacting, and filtering reacting liquid is added methylene chloride extraction, has
Machine is mutually washed with saturated sodium bicarbonate solution, until water phase PH=8, repeatedly, organic phase is dry for washing, and revolving obtains 3- ammonia except solvent
Base acrylonitrile.
It further limits, the detailed process of step B are as follows: vinyl ethyl ether, pyridine and dichloro are sequentially added in reaction flask
Methane.Phosphorus pentachloride is added in there-necked flask, trifluoroacetic acid is added dropwise overnight in ice salt bath constant pressure funnel, in room temperature after being added dropwise
Under be stirred to react, be washed with water after reaction, 10% salt pickling, saturated sodium bicarbonate solution is washed, dry, filter, obtain crude product, weight
Crystallize to obtain 4- ethyoxyl -1,1,1- trifluoro butyl- 3- alkene -2- ketone.
It further limits, the detailed process of step C are as follows: 3- aminoacrylonitrile, 4- ethyoxyl-are sequentially added in reaction flask
1,1,1- trifluoro butyl- 3- alkene -2- ketone and toluene.N-hexane is added after for a period of time in heating reflux reaction while hot, adds certain
The dilute hydrochloric acid of amount is precipitated solid, stirs 1h under ice bath, filter, dry to obtain 2-(aminomethylene)-6,6,6- tri- fluoro- 5- oxos
Hex- 3- alkene nitrile hydrochloride.
It further limits, the detailed process of step D are as follows: 2-(aminomethylene)-6 are added in reaction flask, 6,6- tri- is fluoro-
As reaction dissolvent, nitrogen protection reaction system adds phosphorous acid by 5- oxo hex- 3- alkene nitrile hydrochloride and DCC, DMSO, in
Be stirred to react certain time at room temperature, in the reaction system plus water, extracted with toluene, merge organic phase, washing twice, saturation food
Salt washing is primary, and dry organic phase, revolving obtains bronzing liquid 6- (trifluoromethyl) nicotinic acid nitrile.
It further limits, the detailed process of step E are as follows: water, sulfuric acid and glacial acetic acid are added in reaction flask, is slowly added to 6-
(trifluoromethyl) nicotinic acid nitrile.It is refluxed overnight reaction.Ice cube is added in cooling, and cooling with brine ice, white solid is precipitated, after filtering
Filtrate is extracted with ethyl acetate, and merges organic phase, twice, the dry revolving of organic phase, pickling decolourizes to obtain beige solid for washing
6- (trifluoromethyl) pyridine carboxylic acid.
It further limits, the detailed process of step F are as follows: be passed through nitrogen into the ultrasonic response container for being equipped with agitating device
Then the dichloromethane solution dissolved with 6- (trifluoromethyl) pyridine carboxylic acid is added in gas, anti-to ultrasonic wave in 25 DEG C after ammonium hydroxide is added
The methanol solution being added dropwise in container dissolved with chromium trichloride is answered, agitating device and ultrasonic generator is opened during being added dropwise, surpasses
The setpoint frequency of sound wave generating device is 80KHz, and dripping rear solution is clear state, stops stirring, keeps ultrasonic wave
Device works on, and is cooled to 0 DEG C of standing reaction solution, opens the gas vent on ultrasonic response container, keeps the nitrogen being passed through
It is discharged from gas vent, makes nitrogen that ultrasonic response container be discharged with reaction dissolvent, have clear crystal precipitation, crystallization is complete after 5h
Entirely, reaction solution is filtered, filter cake is washed with methanol repeatedly to wash away extra chromium chloride, and filter cake obtains after drying at room temperature
It further limits, the gained compound of step F specifically acts on are as follows:It is right
Store pig plays good growth；With very low bioconcentration.
Specific embodiment
Above content of the invention is described in further details by the following examples, but this should not be interpreted as to this
The range for inventing above-mentioned theme is only limitted to embodiment below, and all technologies realized based on above content of the present invention belong to this hair
Bright range.
Embodiment 1
Cyanoacetic acid 170g (2mol) and methanol 200mL are added in 2000mL reaction flask, adds carbonyl reduction catalysis
Agent NaBH (OAc)3Ammonium hydroxide 800mL is slowly added dropwise in 10g, nitrogen protection reaction system, and control temperature is no more than during being added dropwise
60 DEG C, heating reflux reaction after completion of dropwise addition, TLC monitors raw material fully reacting, and methylene chloride 500mL is added in filtering reacting liquid
It extracts reaction solution twice, merges organic phase, organic phase is washed with saturated sodium bicarbonate solution, until water phase PH=8, is washed with water
2 times, organic phase is dry, and revolving obtains 3- aminoacrylonitrile 125g, yield 92% except solvent.
Embodiment 2
Vinyl ethyl ether 375.9g (5.23mol), pyridine 826.8g, methylene chloride are sequentially added in the there-necked flask of 10L
5000mL.Phosphorus pentachloride 1084.2g is added in there-necked flask, trifluoroacetic acid 444.6g is added dropwise overnight in ice salt bath constant pressure funnel
(3.89mol), is stirred to react 48h at room temperature after being added dropwise.Reaction system is washed with water, 10% salt pickling, unsaturated carbonate hydrogen
Sodium solution is washed, dry, is filtered, is obtained crude product, recrystallizes to obtain sterling 4- ethyoxyl -1,1,1- trifluoro butyl- 3- alkene -2- ketone 602.0g,
Yield is 92.1%.
Embodiment 3
3- aminoacrylonitrile 136g (2mol), 4- ethyoxyl -1,1,1- trifluoro butyl- are sequentially added in the there-necked flask of 10L
3- alkene -2- ketone 370g (2.2mol) and toluene 1800mL.N-hexane 3900mL is added while hot, adds by heating reflux reaction 48h
Solid is precipitated after cooling in dilute hydrochloric acid solution 1000mL.1h is stirred under ice bath, filters, dry to obtain 2-(aminomethylene)-6,6,6-
Three fluoro- 5- oxo hex- 3- alkene nitrile hydrochloride 410g, yield 91%.
Embodiment 4
The fluoro- 5- oxo hex- 3- alkene nitrile hydrochloric acid of 2-(aminomethylene)-6,6,6- three is sequentially added in the there-necked flask of 10L
Salt 450g (2.0mol), DCC400g (2mol) and DMSO 1000mL are stirred to react.Under nitrogen protection, it is slowly added dropwise dissolved with Asia
The DMSO100mL of phosphoric acid 20g, is stirred to react 2h at room temperature, and TLC monitors raw material fully reacting.In the reaction system plus water
10L is extracted with toluene, merges organic phase, twice, saturated common salt washing is primary for washing, and dry organic phase, revolving obtains bronzing
Liquid 6- (trifluoromethyl) nicotinic acid nitrile 300g, yield 88%.
Embodiment 5
Water 1420g, sulfuric acid 2440g, glacial acetic acid 150mL are added in the there-necked flask of 10L, is slowly added to 6- (trifluoromethyl)
Nicotinic acid nitrile 870g (5mol).It is refluxed overnight reaction.Ice cube is added in cooling, and cooling with brine ice, and white solid is precipitated.Filtering, filter
Liquid is extracted with ethyl acetate, and merges organic phase, twice, the dry revolving of organic phase, pickling decolourizes to obtain beige solid 5- for washing
(trifluoromethyl) pyridine carboxylic acid 930g, yield 97.3%.
Embodiment 6
It is passed through nitrogen into the ultrasonic response container for being equipped with agitating device, is then added dissolved with 6- (trifluoromethyl) pyrrole
The methylene chloride 800mL solution of pyridine formic acid 190g (1mol), after the ammonium hydroxide 100mL that concentration is 25% is added, in 25 DEG C to ultrasound
The methanol solution 500mL dissolved with six hydrated chromium trichloride 133g (0.5mol) is added dropwise in wave reaction vessel, is opened during being added dropwise
Agitating device and ultrasonic generator, the setpoint frequency of ultrasonic generator are 80KHz, drip rear solution as clarification shape
State stops stirring, and ultrasonic generator is kept to work on, and is cooled to 0 DEG C of standing reaction solution, opens ultrasonic response container
On gas vent, keep the nitrogen being passed through from gas vent be discharged, make nitrogen with reaction dissolvent be discharged ultrasonic response container, have
Clear crystal is precipitated, and crystallization is complete after 5h, filters reaction solution, and filter cake is washed with methanol repeatedly to wash away extra chromium chloride, filter
Cake obtains after drying at room temperature81g, yield 93%.
Embodiment 7
Ternary Pig ternary fattening pig 60 is selected in test, control group and test group is assigned randomly to according to weight, in every group
If 3 repetitions, 10 test pigs of each repetition.Test pig point circle raising, is freely eaten and drinking-water, pig house keep hygienically clean and
Air circulation periodically sterilizes.Control group fed basal diet, test group added on the basis of basal diet 300 μ g/kg (with
Chromium meter) chromium picolinate.The total 67d of test period, wherein preliminary trial period 7d, positive to try phase 60d.
Two groups of basal diet formula is consistent, and test daily ration is prepared referring to U.S. NRC (1998 editions) fattening pig nutritional need.
Daily gain and feed intake: on-test and at the end of, weigh on an empty stomach to each group pig in breakfast 8:00 respectively,
Every group of feed consumption rate is counted, the daily gain of each group pig, feed intake and feedstuff-meat ratio are calculated.
Data analysis: data analysis is carried out using SPSS12.0 statistical analysis software, makees Multiple range test with duncan's method, is tried
Testing data is indicated with mean+SD.
Influence of the target compound to growing and fattening daily gain in pigs, feed intake and feedstuff-meat ratio
Embodiment 8
To rat feed high chromium daily ration (5000ng/g, withForm) 3 weeks, greatly
Mouse kidney, liver, heart, the accumulation of chromium is respectively 211,29,16,11ng/g in leg gastrocnemius, these accumulations are lower than body
Outer test can generate the concentration of mutation effect.
Embodiment above describes basic principles and main features of the invention and advantage, the technical staff of the industry should
Understand, the present invention is not limited to the above embodiments, and the above embodiments and description only describe originals of the invention
Reason, under the range for not departing from the principle of the invention, various changes and improvements may be made to the invention, these changes and improvements are each fallen within
In the scope of protection of the invention.
Claims (8)
1. a kind of novel processing step of chromium picolinate based food additive, it is characterised in that specific steps are as follows:
A, cyanoacetic acid reacts with ammonium hydroxide under carbonyl reduction catalyst action and generates 3- aminoacrylonitrile；
B, vinyl ethyl ether and trifluoroacetic acid generate 4- ethyoxyl -1,1,1- trifluoro butyl- 3- under pyridine and phosphorus pentachloride effect
Alkene -2- ketone；
C, 3- aminoacrylonitrile and the generation substitution reaction of 4- ethyoxyl-1,1,1- trifluoro butyl- 3- alkene-2- ketone obtain 2-(amino Asias
Methyl) three fluoro- 5- oxo hex- 3- alkene nitrile hydrochloride of -6,6,6-；
D, the fluoro- 5- oxo hex- 3- alkene nitrile hydrochloride of 2- (aminomethylene) -6,6,6- three DCC and phosphorous acid effect under itself
Cyclization obtains 6- (trifluoromethyl) nicotinic acid nitrile；
E, 6- (trifluoromethyl) nicotinic acid nitrile is oxidized to obtain 6- (trifluoromethyl) pyridine carboxylic acid；
F, 6- (trifluoromethyl) pyridine carboxylic acid reacts to obtain in ultrasound reactor with chromium trichloride
2. a kind of novel processing step of chromium picolinate based food additive according to claim 1, it is characterised in that
The detailed process of step A are as follows: cyanoacetic acid and methanol are added in reaction flask, adds carbonyl reduction catalyst n aBH
(OAc)3, nitrogen protection reaction system is slowly added dropwise ammonium hydroxide, and control temperature is no more than 60 DEG C, after completion of dropwise addition during being added dropwise
Heating reflux reaction, TLC monitor raw material fully reacting, and methylene chloride extraction, organic phase unsaturated carbonate is added in filtering reacting liquid
The washing of hydrogen sodium solution, until water phase PH=8, is washed 2 times, organic phase is dry, and revolving obtains 3- aminoacrylonitrile except solvent.
3. a kind of novel processing step of chromium picolinate based food additive according to claim 1, it is characterised in that
The detailed process of step B are as follows: vinyl ethyl ether, pyridine and methylene chloride are sequentially added in reaction flask；It is added in there-necked flask
Phosphorus pentachloride is added dropwise trifluoroacetic acid in ice salt bath constant pressure funnel overnight, is stirred to react at room temperature after being added dropwise；Reaction system
It being washed with water, 10% salt pickling, saturated sodium bicarbonate solution is washed, and it is dry, it filters, obtains crude product, recrystallize to obtain 4- ethyoxyl -1,1,1-
Trifluoro butyl- 3- alkene -2- ketone.
4. a kind of novel processing step of chromium picolinate based food additive according to claim 1, it is characterised in that
The detailed process of step C are as follows: 3- aminoacrylonitrile, 4- ethyoxyl -1,1,1- trifluoro butyl- 3- alkene-are sequentially added in reaction flask
N-hexane is added after for a period of time in 2- ketone and toluene, heating reflux reaction while hot, adds a certain amount of dilute hydrochloric acid, is precipitated solid
Body；1h is stirred under ice bath, filters, dry to obtain 2-(aminomethylene)-6,6,6- tri- fluoro- 5- oxo hex- 3- alkene nitrile hydrochlorides.
5. a kind of novel processing step of chromium picolinate based food additive according to claim 1, it is characterised in that
The detailed process of step D are as follows: the fluoro- 5- oxo hex- 3- alkene nitrile hydrochloric acid of 2-(aminomethylene)-6,6,6- three is added in reaction flask
Salt and DCC, DMSO add phosphorous acid as reaction dissolvent, nitrogen protection reaction system, are stirred to react a timing at room temperature
Between, it in the reaction system plus water, is extracted with toluene, merges organic phase, twice, saturated common salt washing is primary, and drying is organic for washing
Phase, revolving obtain bronzing liquid 6- (trifluoromethyl) nicotinic acid nitrile.
6. a kind of novel processing step of chromium picolinate based food additive according to claim 1, it is characterised in that
The detailed process of step E are as follows: water, sulfuric acid and glacial acetic acid are added in reaction flask, is slowly added to 6- (trifluoromethyl) nicotinic acid nitrile, flows back
Reaction overnight；Ice cube is added after reaction, and cooling with brine ice, white solid, filtrate ethyl acetate after filtering is precipitated
Extraction merges organic phase, and twice, the dry revolving of organic phase, pickling decolourizes to obtain beige solid 6- (trifluoromethyl) pyrrole for washing
Pyridine formic acid.
7. a kind of novel processing step of chromium picolinate based food additive according to claim 1, it is characterised in that
The detailed process of step F are as follows: be passed through nitrogen into the ultrasonic response container for being equipped with agitating device, be then added dissolved with 6-
The dichloromethane solution of (trifluoromethyl) pyridine carboxylic acid, be added ammonium hydroxide after, in 25 DEG C into ultrasonic response container be added dropwise dissolved with
The methanol solution of chromium trichloride opens agitating device during being added dropwise and ultrasonic generator, ultrasonic generator is set
Determining frequency is 80KHz, and dripping rear solution is clear state, stops stirring, and ultrasonic generator is kept to work on, and is cooled down
To 0 DEG C of standing reaction solution, the gas vent on ultrasonic response container is opened, keeps the nitrogen being passed through to be discharged from gas vent, makes nitrogen
Ultrasonic response container is discharged with reaction dissolvent in gas, there is clear crystal precipitation, and crystallization is complete after 5h, filters reaction solution, filter cake
It is washed with methanol repeatedly to wash away extra chromium chloride, filter cake obtains after drying at room temperature
8. a kind of chromium picolinate based food additive as described in claim 1 is preparing the application in food additives.
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| Synthesis of Triflouromethylated Pyridinecarbonitriles;Maria Teresa Cocco et al.;《Journal of Heterocyclic Chemistry》;19950430;第32卷;543-545 * |
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