CN106290673B - A kind of method that eutectic solvent extraction liquid chromatography quickly measures rhodamine B - Google Patents
A kind of method that eutectic solvent extraction liquid chromatography quickly measures rhodamine B Download PDFInfo
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- CN106290673B CN106290673B CN201610854066.6A CN201610854066A CN106290673B CN 106290673 B CN106290673 B CN 106290673B CN 201610854066 A CN201610854066 A CN 201610854066A CN 106290673 B CN106290673 B CN 106290673B
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Abstract
The present invention provides the methods that a kind of eutectic solvent extraction liquid chromatography quickly measures rhodamine B, it comprises the following steps, first prepare the solution of rhodamine B, and it is diluted to the rhodamine B standard working solution of various concentration, the liquid chromatogram of rhodamine B standard working solution is detected using liquid chromatograph, and makes calibration curve；Eutectic solvent is prepared, the eutectic solvent includes hydrogen bond acceptor compounds and hydrogen bond donor compound；Seasoning oil samples are weighed, the eutectic solvent and alkane reagent is added in, is extracted, oil reservoir above is removed after centrifugation, residue is detected to obtain the chromatogram of sample after being washed with alkane using liquid chromatograph；The chromatogram of sample is qualitative compared with the chromatogram of standard working solution, it is quantified further according to the concentration on the standard curve corresponding to peak area.Technical scheme is highly practical, easy to operate, and complicated pretreatment process is not required, and experimental cost is low.
Description
Technical field
The invention belongs to non-food coloring detection technique field in food more particularly to a kind of eutectic solvent extraction liquid phases
The method that chromatography quickly measures rhodamine B.
Background technology
Rhodamine B also known as basic rhodamine, pollen are red, are a kind of artificial synthesized oxa anthracenes fluorescent dyes, main to use
Glazed paper, typing paper, glazed paper etc. are contaminated in paper industry, also has application in industries such as coloured glass, characteristic fireworks and firecrackers.Due to
Rhodamine B is easier to dye in chafing dish bottom flavorings, chilli powder, flavored oils etc. than other edible water-soluble dyestuffs, and not fugitive color,
It is at low cost, therefore some illegal retailers dye these food with rhodamine, adulterate.International cancer research aircraft
The evaluation of structure (International Agency for Research on Cancer, IARC) chemicals carcinogenic risk shows：It takes the photograph
It takes, suck and skin contact rhodamine B, can cause acute or chronic middle toxicity damage.Zoopery shows rhodamine B
There is carcinogenesis, mutagenesis or teratogenesis may be caused.Ministry of Health of China is listed in《The non-edible object of possible illegal addition in food
Matter and the food additives kind list (the 1st batch) easily abused》In, it is forbidden to be used in food, the national explicit order such as America and Europe
Forbid rhodamine B in food processing.However, it in recent years, is increased in government and illegal food additive additive color element tonyred is beaten
It hits after dynamics, the situation of illegal addition rhodamine B is more prominent in food.At present, China there is no rhodamine B in detection food
National standard, common detection method be then 2010 promulgate inspection and quarantining for import/export professional standard SN/T 2430-
2010, but this method during chilli oil is detected, it is necessary to which GPC cleanup system system carries out sample pre-treatments, process is multiple
Miscellaneous, of high cost, time-consuming.
The content of the invention
For more than technical problem, the invention discloses a kind of eutectic solvent extraction liquid chromatography quickly to measure Luo Dan
The method of bright B, this method is easy to operate, and detection is quick, of low cost.
In this regard, the technical solution adopted by the present invention is：
A kind of method that eutectic solvent extraction liquid chromatography quickly measures rhodamine B, comprises the following steps：
Step S1：The solution of rhodamine B is prepared, and is diluted to the rhodamine B standard working solution of various concentration, is respectively adopted
Liquid chromatograph is detected to obtain the liquid chromatogram of the rhodamine B standard working solution of various concentration；According to liquid chromatogram
Peak area and corresponding concentration make calibration curve；
Step S2：Eutectic solvent is prepared, the eutectic solvent includes hydrogen bond acceptor compounds and hydrogen bond donor chemical combination
Object；
Step S3：Seasoning oil samples are weighed, eutectic solvent and alkane reagent described in step S2 is added in, is extracted,
Oil reservoir above is removed after centrifugation, residue is detected to obtain the chromatography of sample after being washed with alkane using liquid chromatograph
Figure；Wherein, the volume ratio of the eutectic solvent and alkane reagent is more than 0.0025；
Step S4：The chromatogram of sample is determined whether compared with the chromatogram of standard working solution containing rhodamine B,
The content of rhodamine B in sample is determined further according to the concentration on the standard curve corresponding to the chromatogram peak area of sample.
Using this technical solution, the rhodamine B in seasoning oil samples, alkanes reagent oil removing are extracted using eutectic solvent
Removal of impurities, then by machine testing on eutectic solvent, realize quick detection, step is simple, without complicated sample pretreatment process,
Reduce the use of solvent, while eliminate the interference of complex matrices in flavored oils again, ensure that the accuracy of testing result.
As a further improvement on the present invention, the hydrogen bond acceptor compounds be quaternary amine, the hydrogen bond donor compound
For at least one of glycerine and ethylene glycol, the molar ratio of the hydrogen bond acceptor compounds and hydrogen bond donor compound is 1：(1
~3).
The dosage of the eutectic solvent is according to every gram of 0.05~5.0mL of seasoning oil samples.
As a further improvement on the present invention, the quaternary amine is choline chloride, and the choline chloride is supplied with the hydrogen bond
The molar ratio of body compound is 1:1、1:2 or 1:3.
As a further improvement on the present invention, the hydrogen bond donor compound is glycerine.
As a further improvement on the present invention, the alkane reagent is aliphatic reagent；Further, the alkane reagent
Including at least one of n-hexane, hexamethylene, octane, heptane.
As a further improvement on the present invention, the volume ratio of the eutectic solvent and alkane reagent is 0.5~5.
As a further improvement on the present invention, the alkane reagent is n-hexane or normal heptane.
As a further improvement on the present invention, in step S3, the mode of the extraction is shaking table concussion extraction or ultrasonic wave
Extraction, the Extracting temperature are 10-50 DEG C.It is further preferred that the mode of the extraction is shaking table concussion extraction.
As a further improvement on the present invention, in step S3, residue is washed with alkane and removes remaining oil, then will be low
Congruent melting solvent directly goes up machine or constant volume to upper machine testing after required volume.
Compared with prior art, beneficial effects of the present invention are：
First, technical scheme is highly practical, big for viscosity such as chilli oil, chilly oil, Arnotto orange oils,
The seasoning oil samples of matrix complexity can carry out the accurate detection of rhodamine B.
Second, technical scheme is easy to operate, at low cost, present invention only requires simple sample extraction process,
Complicated pretreatment process is not required, the use of organic solvent can be saved by extracting eutectic solvent used, be greatly reduced
Experimental cost.
3rd, technical scheme detection is quick, since this method can save time for sample pretreatment, contracts significantly
Rhodamine B detects the required time in Duan Liao flavored oils.
4th, recovery of standard addition is high, and detection limit is low, and eutectic solvent can effectively extract rhodamine B from flavored oils,
Alkanes reagent can remove complicated oil matrix simultaneously, and impurity is avoided to disturb, thus can ensure the sufficiently high rate of recovery and
Relatively low detection limit, the rate of recovery is in 75.2%-105%, and detection limit is up to 2.5 μ g/kg.
Description of the drawings
Fig. 1 is the fluorescence chromatogram that the rhodamine B content of an embodiment of the present invention is the standard solution of 5.0 μ g/L.
Fig. 2 is an embodiment of the present invention rhodamine B standard working solution calibration curve.
Specific embodiment
The present invention is made with reference to Figure of description and specific embodiment and further being elaborated, the embodiment
It is served only for explaining the present invention, is not intended to limit the scope of the present invention.Material, reagent, instrument used in following embodiments
Equipment etc. is commercially available unless otherwise specified.
Methanol：Chromatographically pure is purchased from Merck ＆ Co., Inc.；N-hexane：Chromatographically pure is purchased from Merck ＆ Co., Inc.；Normal heptane：Chromatographically pure, purchase
In Merck ＆ Co., Inc.；Choline chloride：Analyze pure, Aladdin；Glycerine：Analyze pure, Shanghai Ling Feng；Water is ultra-pure water.
Rhodamine B standard items：Purity 95.00%, purchased from Dr.Ehrenstorfer.
Ultra Performance Liquid Chromatography instrument：It is equipped with quaternary gradient pump, degasser, microsyringe, fluorescence detector.
Liquid phase chromatogram condition parameter is as follows：
Chromatographic column：1.7 μm of ACQUITY UPLC BEH C18,2.1 × 50mm
Column temperature：25℃
Detector excitation wavelength：550nm
Detector launch wavelength：580nm
The concrete condition of mobile phase is as shown in table 1.
Table 1
Follow the steps below detection：
Step S1：The solution of rhodamine B is first prepared, and is diluted to the rhodamine B standard working solution of various concentration, is adopted respectively
It is detected to obtain the liquid chromatogram of the rhodamine B standard working solution of various concentration with liquid chromatograph；According to liquid chromatogram
The peak area of figure and corresponding concentration make calibration curve；Rhodamine B content is the fluorescence chromatogram of the standard solution of 5.0 μ g/L
As shown in Figure 1；Rhodamine B standard working solution calibration curve is as shown in Figure 2.
Step S2：The preparation of eutectic solvent DES-1：The glycerine for weighing 20g choline chlorides and 13.19g is anti-in 100mL
It answers in bottle, until being warming up to 90 DEG C and stirring to clarify, is cooled to room temperature spare.
The preparation of eutectic solvent DES-2：The glycerine of 20g choline chlorides and 26.38g are weighed in 100mL reaction bulbs,
Until being warming up to 90 DEG C and stirring to clarify, it is cooled to room temperature spare.
The preparation of eutectic solvent DES-3：The glycerine of 20g choline chlorides and 39.57g are weighed in 100mL reaction bulbs,
Until being warming up to 90 DEG C and stirring to clarify, it is cooled to room temperature spare.
Step S3：Seasoning oil samples are weighed, eutectic solvent and alkane reagent described in step S2 is added in, is extracted,
Oil reservoir above is removed after centrifugation, residue is detected to obtain the chromatography of sample after being washed with alkane using liquid chromatograph
Figure；Wherein, the volume ratio of the eutectic solvent and alkane reagent is more than 0.0025；
Step S4：The chromatogram of sample is determined whether compared with the chromatogram of standard working solution containing rhodamine B,
The content of rhodamine B in sample is determined further according to the concentration on the standard curve corresponding to the chromatogram peak area of sample.
Embodiment 1
Sample：Chilli oil 1g is weighed in 15mL centrifuge tubes, adds in 1.0mL eutectic solvent DES-1 and 5mL n-hexanes,
Shaking table concussion extraction 10 minutes, 7500r/min is centrifuged 2 minutes, and the oil reservoir drawn above with plastic suction pipe discards, and adds 5mL
N-hexane, concussion washing 1 minute, 7500r/min is centrifuged 2 minutes, and oil reservoir above is siphoned away with plastic suction pipe to be discarded.It is remaining low
Congruent melting solvent DES-1 part methanol constant volumes to 5.0mL, vortex mixing crosses 0.22 μm of organic filter membrane, examination with computer.
Mark-on sample：Chilli oil 1g is weighed in 15mL centrifuge tubes, adds the concentration level of rhodamine B as 5.0 μ g/kg,
6 mark-on samples are made respectively.1.0mL eutectic solvent DES-1 and 5mL n-hexanes, shaking table are separately added into mark-on sample
Concussion extraction 10 minutes, 10 DEG C of Extracting temperature, 7500r/min is centrifuged 2 minutes, and the oil reservoir drawn above with plastic suction pipe discards,
Add 5mL n-hexanes, concussion washing 1 minute, 7500r/min centrifuges 2 minutes, and oil reservoir above is siphoned away with plastic suction pipe to be abandoned
It goes.Remaining eutectic solvent DES-1 parts methanol constant volume to 5.0mL, vortex mixing crosses 0.22 μm of organic filter membrane, upper machine
Test.
The chromatogram of sample is determined whether compared with the chromatogram of standard working solution containing rhodamine B, further according to
The concentration on standard curve corresponding to the chromatogram peak area of sample determines the content of rhodamine B in sample, obtained result
As shown in table 2.
The testing result table of 2 embodiment 1 of table
Wherein, RSD is relative standard deviation (relative standard deviation).
Embodiment 2
Sample：Chilly oil 1g is weighed in 15mL centrifuge tubes, adds in 0.6mL eutectic solvent DES-2 and 6mL normal heptanes,
Shaking table concussion extraction 15 minutes, 7500r/min is centrifuged 3 minutes, and the oil reservoir drawn above with plastic suction pipe discards, and adds 5mL
Normal heptane, concussion washing 1 minute, 7500r/min is centrifuged 2 minutes, and oil reservoir above is siphoned away with plastic suction pipe to be discarded.It is remaining low
Congruent melting solvent DES-2 part methanol constant volumes to 5.0mL, vortex mixing crosses 0.22 μm of organic filter membrane, examination with computer.
Mark-on sample：Chilly oil 1g is weighed in 15mL centrifuge tubes, adds the concentration level of rhodamine B as 5.0 μ g/kg,
6 mark-on samples are made respectively.0.6mL eutectic solvent DES-2 and 6mL normal heptanes, shaking table are separately added into mark-on sample
Concussion extraction 15 minutes, 30 DEG C of Extracting temperature, 7500r/min is centrifuged 3 minutes, and the oil reservoir drawn above with plastic suction pipe discards,
Add 5mL normal heptanes, concussion washing 1 minute, 7500r/min centrifuges 2 minutes, and oil reservoir above is siphoned away with plastic suction pipe to be abandoned
It goes.Remaining eutectic solvent DES-2 parts methanol constant volume to 5.0mL, vortex mixing crosses 0.22 μm of organic filter membrane, upper machine
Test.
The chromatogram of sample is determined whether compared with the chromatogram of standard working solution containing rhodamine B, further according to
The concentration on standard curve corresponding to the chromatogram peak area of sample determines the content of rhodamine B in sample, obtained result
As shown in table 3.
The testing result table of 3 embodiment 2 of table
Embodiment 3
Sample：Arnotto orange oil 1g is weighed in 15mL centrifuge tubes, is adding in 0.5mL eutectic solvents DES-3 and 10mL just
Heptane, shaking table concussion extraction 20 minutes, 7500r/min is centrifuged 2 minutes, and the oil reservoir drawn above with plastic suction pipe discards, then is added
Enter 6mL normal heptanes, concussion washing 1 minute, 7500r/min centrifuges 2 minutes, and oil reservoir above is siphoned away with plastic suction pipe to be discarded.It is residual
The eutectic solvent DES-3 part methanol constant volumes stayed to 5.0mL, vortex mixing crosses 0.22 μm of organic filter membrane, examination with computer.
Mark-on sample：Arnotto orange oil 1g is weighed in 15mL centrifuge tubes, the concentration level for adding rhodamine B is 5.0 μ g/
Kg makes 6 mark-on samples respectively.0.5mL eutectic solvent DES-3 and 10mL normal heptanes are separately added into mark-on sample,
Shaking table concussion extraction 20 minutes, 50 DEG C of Extracting temperature, 7500r/min is centrifuged 2 minutes, and the oil reservoir drawn above with plastic suction pipe is abandoned
It goes, adds 6mL normal heptanes, concussion washing 1 minute, 7500r/min is centrifuged 2 minutes, and oil reservoir above is siphoned away with plastic suction pipe
It discards.Remaining eutectic solvent DES-3 parts methanol constant volume to 5.0mL, vortex mixing crosses 0.22 μm of organic filter membrane, on
Machine is tested.
The chromatogram of sample is determined whether compared with the chromatogram of standard working solution containing rhodamine B, further according to
The concentration on standard curve corresponding to the chromatogram peak area of sample determines the content of rhodamine B in sample, obtained result
As shown in table 4.
The testing result table of 4 embodiment 3 of table
And be found through experiments that, other eutectic solvents, such as the eutectic solvent that choline chloride and metal salt form, viscosity
It is too big, it is not suitable for the sample pre-treatments operation of liquid-liquid extraction.It is drawn by repetition test, recovery of standard addition is in 75.2%-
105%, detection limit is up to 2.5 μ g/kg.
The above content is a further detailed description of the present invention in conjunction with specific preferred embodiments, it is impossible to assert
The specific implementation of the present invention is confined to these explanations.For those of ordinary skill in the art to which the present invention belongs, exist
On the premise of not departing from present inventive concept, several simple deduction or replace can also be made, should all be considered as belonging to the present invention's
Protection domain.
Claims (7)
1. a kind of method that eutectic solvent extraction liquid chromatography quickly measures rhodamine B, it is characterised in that：It includes following
Step：
Step S1：The solution of rhodamine B is prepared, and is diluted to the rhodamine B standard working solution of various concentration, liquid phase is respectively adopted
Chromatograph is detected to obtain the liquid chromatogram of the rhodamine B standard working solution of various concentration；According to the peak of liquid chromatogram
Area and corresponding concentration make calibration curve；
Step S2：Eutectic solvent is prepared, the eutectic solvent includes hydrogen bond acceptor compounds and hydrogen bond donor compound；
Step S3：Seasoning oil samples are weighed, eutectic solvent and alkane reagent described in step S2 is added in, is extracted, are centrifuged
Oil reservoir above is removed afterwards, and residue is detected to obtain the chromatogram of sample after being washed with alkane using liquid chromatograph；Its
In, the volume ratio of the eutectic solvent and alkane reagent is more than 0.0025；
Step S4：The chromatogram of sample is determined whether compared with the chromatogram of standard working solution containing rhodamine B, then root
The content of rhodamine B in sample is determined according to the concentration on the standard curve corresponding to the chromatogram peak area of sample；The hydrogen bond
Acceptor compound is choline chloride, and the hydrogen bond donor compound is at least one of glycerine and ethylene glycol；It is described low common
The dosage of molten solvent is according to every gram of 0.05 ~ 5.0 mL of seasoning oil samples；The choline chloride and the hydrogen bond donor compound
Molar ratio is 1:1、1:2 or 1:3；The alkane reagent includes at least one of n-hexane, hexamethylene, octane, heptane.
2. the method that eutectic solvent extraction liquid chromatography according to claim 1 quickly measures rhodamine B, feature
It is：The hydrogen bond donor compound is glycerine.
3. the method that eutectic solvent extraction liquid chromatography according to claim 1 quickly measures rhodamine B, feature
It is：The volume ratio of the eutectic solvent and alkane reagent is 0.5 ~ 5.
4. the method that eutectic solvent extraction liquid chromatography according to claim 1 quickly measures rhodamine B, feature
It is：The alkane reagent is n-hexane or normal heptane.
5. the eutectic solvent extraction liquid chromatography according to claim 1 ~ 4 any one quickly measures rhodamine B
Method, it is characterised in that：In step S3, the mode of the extraction is extracted for shaking table concussion or ultrasonic wave extraction, the extraction
Temperature is at 10-50 DEG C.
6. the method that eutectic solvent extraction liquid chromatography according to claim 5 quickly measures rhodamine B, feature
It is：The mode of the extraction is shaking table concussion extraction.
7. the method that eutectic solvent extraction liquid chromatography according to claim 5 quickly measures rhodamine B, feature
It is：In step S3, residue is washed with alkane and removes remaining oil, then directly goes up machine or constant volume to required volume
Upper machine testing afterwards.
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| CN107748211B (en) * | 2017-09-14 | 2020-05-19 | 大连大学 | Method for extracting and measuring 5 macamides in maca by using deep eutectic solvent |
| CN108627373B (en) * | 2018-04-20 | 2021-11-09 | 三明出入境检验检疫局综合技术服务中心 | Preparation method and application of papaverine standard substance serving as hot pot food matrix |
| CN108572231B (en) * | 2018-06-26 | 2020-10-02 | 河南师范大学 | Method for detecting Sudan red I by using hydrophobic eutectic solvent vortex-assisted dispersion liquid microextraction-high performance liquid chromatography |
| CN109001332A (en) * | 2018-09-06 | 2018-12-14 | 河南工业大学 | The measuring method of the original additive amount of TBHQ in a kind of edible oil and fat |
| CN110231423B (en) * | 2019-07-05 | 2022-04-22 | 山西农业大学 | Method for measuring pyrethroid pesticides in grains by dispersion liquid microextraction-high performance liquid chromatography |
| CN110270130B (en) * | 2019-07-21 | 2021-06-25 | 河南师范大学 | Lidocaine-based hydrophobic eutectic solvent and preparation method and application thereof |
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