CN111965182A - Method for manufacturing ethylene oxide rapid detection test paper - Google Patents
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- CN111965182A CN111965182A CN202010741532.6A CN202010741532A CN111965182A CN 111965182 A CN111965182 A CN 111965182A CN 202010741532 A CN202010741532 A CN 202010741532A CN 111965182 A CN111965182 A CN 111965182A
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- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
- G01N21/77—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator
- G01N21/78—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator producing a change of colour
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Abstract
The invention provides a method for manufacturing ethylene oxide rapid detection test paper, which is characterized in that pyridine derivatives capable of performing ring-opening color change reaction with ethylene oxide and auxiliary reagents capable of improving the reaction rate are pre-loaded on the test paper. The ethylene oxide detection method by means of chemical color development can avoid the use of high temperature and power supply and is applied to the detection requirement under milder and safer conditions.
Description
The technical field is as follows:
the invention provides a detection method based on colorimetric method ethylene oxide and a detection test paper manufacturing method, which are characterized by high reaction speed and high sensitivity.
Background art:
ethylene Oxide (C)2H4O), also known as ethylene oxide, dioxane. The boiling point is 10.8 ℃, and the gas is colorless gas at normal temperature and normal pressure. Ethylene oxide is an important chemical product of ethylene industrial derivatives, second only to polyethylene and polyvinyl chloride, and is mainly used for producing ethylene glycol and synthesizing nonionic surfactants, ethanolamine, polyethylene glycol, choline, medical intermediates and other derivatives. In addition, the ethylene oxide is a second generation high-efficiency low-temperature disinfection preparation following formaldehyde, and is widely applied to the sterilization and disinfection of medical instruments, various fabrics, plastic products, fur products and the like.
The ethylene oxide molecule is in a ternary ring structure, the chemical property is extremely active, and the explosion limit in the air is 3-100%. In addition, the ethylene oxide has biological toxicity, belongs to a class of carcinogens in a carcinogen list published by international cancer research institution of world health organization in 2017, and has a national standard specified time weighted average allowable concentration of only 2mg/m3. Therefore, the concentration of the ethylene oxide is monitored on the use site of the ethylene oxide, the gas leakage phenomenon is discovered as soon as possible, and the method has great practical significance for preventing explosion accidents and personal safety protection.
At present, a gas sensor is mainly adopted as a detection method in the field of ethylene oxide production and use, a catalytic combustion method is adopted, the advantages of real-time online monitoring and convenient connection with an alarm device are achieved, and the defect that a power supply is needed to maintain the gas sensing element to be continuously in a high-temperature working state is overcome, so that the explosion-proof requirement on the device is high, and the device is not suitable for being used in a scene without the power supply or in a mobile scene.
The invention aims to provide the ethylene oxide detection method which takes the test paper as the carrier of the detection reagent and develops color by means of a chemical method, thereby avoiding the use of high temperature and power supply and being applied to the detection requirement under the milder and safer condition.
The invention content is as follows:
foreign researchers have disclosed a number of methods for making ethylene oxide test strips based on chemical titration or colorimetric methods.
(1) Manufacturing method of ethylene oxide detection test paper based on acid-base indicator
Nicolet et al[1]The first epoxide quantification method reported in 1930, which quantitatively determined the concentration of two epoxide compounds using ethereal HCl. Since then, numerous scholars developed a series of ring-opening reactions based on hydrohalic acids on epoxy compounds and established titration analysis methods with an acid-base indicator to indicate the endpoint[2-5]. However, in many of these analysis methods, the reaction rate is slow and heating is required for 1 hour or more. Wherein, HBr/acetic acid[4]And inorganic halide salts/perchloric acid[5]Both systems are believed to have relatively fast reaction rates and are capable of direct titration. In addition to halogens, diethylamine has also been developed[6]、Na2S2O3 [7]Mercapto compounds (RSH)[8]Is a quantitative analysis method of nucleophilic reagent. Based on this, researchers use the reaction salt with nucleophilicity, acid-base indicator, nonvolatile acid or base, etc. to prepare solution, negativeThe product is carried on a solid carrier such as test paper and the like, and is used for detecting ethylene oxide in the environment after being dried. When the water-absorbing agent is used, water in the air is absorbed by the water-absorbing substance of the system, or the water is prevented from volatilizing by the humectant, so that a saturated aqueous solution is formed on the surface. The ethylene oxide gas detection methods involving the addition of an acid-base indicator are listed in table 1.
TABLE 1 principle and Properties of ethylene oxide detection based on acid-base indicator method
The ethylene oxide detection method based on the acid-base indicator assumes that the pH change in the reaction system is caused by the ring-opening reaction of ethylene oxide. However, in practice, the change in pH of the system can be caused not only by the ring-opening reaction of ethylene oxide but also by acidic/basic gases in the air (e.g., CO)2、NH3) Temperature, etc. This is the main cause of false detection by this method.
(2) Method for manufacturing ethylene oxide detection test paper with color change based on ring-opening reaction
Lohmann[14]The color reaction between the pyridine derivative and the epoxy compound is reported for the first time in 1939, and a quantitative analysis method for titrating epichlorohydrin by pyridine in a methanol solvent is established, wherein the sensitivity is 0.05%. Based on this principle, Gunther et al[15]4-methylquinoline is used as a nucleophilic reagent and an indicator to carry out quantitative analysis on the ethylene oxide; brewer, etc[16]Characterization of ethylene oxide gas during the sterilization process was performed using 4- (4-nitrobenzyl) pyridine as the indicator.
Other gaseous alkylating agents (e.g., MeBr, MeCl, MeI, etc.) may also undergo ring-opening reactions with pyridine derivatives, resulting in a color change. However, in practical applications, these alkylating agents are not common. Thus, the method is less disturbed than the detection method with the addition of an acid-base indicator.
Reported patents for the detection of ethylene oxide based on the ring-opening reaction of pyridine derivatives are: quyi et al[17]Sodium carbonate, 4- (4-nitrobenzyl) pyridine, bacillus stearothermophilus spores and bacillus stearothermophilus spore liquid are loaded on neutral filter paper of 0.6 multiplied by 2.5cm to prepare a sterilizing gas quick detection reagent paste, the sterilizing degree of ethylene oxide is detected by adopting a chemical-biological method, and the sterilizing time is marked. Hamano et al[18]4- (4-nitrobenzyl) pyridine solution was dropped on a test paper and p-ethylene oxide and CO were used2Coating the polyester film with good barrier property to eliminate CO2Inhibiting effect on color change of 4- (4-nitrobenzyl) pyridine and prolonging the color change time. Eastmen et al[19]The mixture of polyethylene glycol, 4- (4-nitrobenzyl) pyridine, thiourea and water is loaded on the test paper, one side of the test paper is coated with a breathable liquid-proof film, and the other side of the test paper is coated with a common transparent film, so that the ethylene oxide test paper is prepared.
The above-mentioned published ethylene oxide detection methods are mostly used to distinguish between ethylene oxide sterilized and non-sterilized articles, such as color-changing inks, which are applied to the articles to be sterilized when in use, and the sterilized articles will change color after a sufficient period of time, while the non-sterilized articles will keep the original color, so that they can be easily distinguished. Since the ethylene oxide sterilization process requires a sufficiently long contact time and the concentration of ethylene oxide in the gas used is high, and the sterilization process also requires a temperature rise, the reaction rate is required to be relatively slow, so that in many documents it is even necessary to use a polymer to reduce the reaction rate.
Reference documents:
[1]NICOLET B H,POULTER T C.EPOXY ACIDS FROM OLEIC AND ELAIDIC ACIDS1[J].Journal of the American Chemical Society,American Chemical Society,1930,52(3):1186–1191.
[2]HAEBERER E T,MAERKER G.Analysis of soaps with hydrogen bromide in glacial acetic acid[J].Journal of the American Oil Chemists’Society,1963,40(7):274–275.
[3]DANNENBERG H,HARP W R.Determination of Cure and Analysis of Cured Epoxy Resins[J].Analytical Chemistry,1956,28(1):86–90.
[4]DURBETAKI A J.Direct Titration of Oxirane Oxygen with Hydrogen Bromide in Acetic Acid[J].Analytical Chemistry,1956,28(12):2000–2001.
[5]DIJKSTRA R,DAILMEN E A M F.An improved direct titration of α-epoxy compounds using crystal violet as the indicator[J].Analytica Chimica Acta,1964,31:38–44.
[6]Hilton F.Analytical methods in rubber chemistry.V.Estimation of the oxygen of highly oxidized rubber contained in carboxyl,ester,carbonyl,epoxide and hydroxyl groups[J].Trans.Inst.Rubber Ind.,1942,17:319.
[7]ROSS W C J.The reactions of certain epoxides in aqueous solutions[J].Journal of the Chemical Society(Resumed),1950:2257–2272.
[8]GUDZINOWICZ B J.Quantitative Determination of Ethylene Epoxide,Propylene Epoxide,and Higher Molecular Weight Epoxides Using Dodecanethiol[J].Analytical Chemistry,1960,32(11):1520–1522.
[9]OLSON M.Procédéet dispositif pour le
de la présence et de l’action de l’oxyde d’éthylèneMinnesota Mining and Manufacturing Co[P]belgium BE610387,1962-05-16.
[10]HALMO F,STRESINKOVA D.
prípravy
papierkov naetylénoxid[P].Czech:CS267944B1,1990-02-12.
[11] JP-A- エチレンオキサイドにより -changing color する was used at インキ [ P ]. Japanese JP55018269B,1980-05-17.
[12]DECKERT W.Eisen(III)-rhodanidpapier als analytisches Reagens bei Luftuntersuchungen[J].Fresenius’Zeitschrift für Analytische Chemie,1956,150(6):421–425.
[13]DECKERT W.Der Gasrestnachweis bei
[J].Angewandte Chemie,1932,45(49):758–759.
[14]LOHMANN H.Eine neue Nachweisreaktion von
und Pyridinderivaten[J].Angewandte Chemie,1939,52(23):407–407.
[15] Microbial of 2- (p-tert-butyl-phenoxy) isoproyl-2-chloroethyl sulfate reactions [ J ]. Analytical Chemistry,1951,23(12): 1835) -1842.
[16]BREWER J H,ARNSBERGER R J.Biological-chemical indicator for ethylene oxide sterilization[J].Journal of Pharmaceutical Sciences,1966,55(1):57–59.
[17] Yeast wine, sterilizing gas fast detecting reagent paste [ P ], China CN101463383A,2009-06-24.
[18] Hamano M, Inoue I, Takeuchi S.indicator for detecting ethylene oxide [ P ]. Europe: EP0060723A1,1982-09-22.
[19] EASTMAN C A, WHITBOURNE J E.ethylene oxide hybridization indicator [ P ]. US: US3992154A,1976-11-16.
The technical scheme is as follows:
the invention aims to provide a method for rapidly detecting semi-quantitative ethylene oxide on site and a method for manufacturing test paper thereof.
The invention aims to solve the following technical problems:
(1) the reaction substrate is screened. A pyridine derivative is found, the requirements of nucleophilic addition reaction with ethylene oxide at normal temperature, obvious color change, high reaction rate and the like are met, and the pyridine derivative is loaded on test paper, so that the qualitative detection of the ethylene oxide can be completed in a short time.
(2) The reaction rate is improved. In order to achieve the goal of rapidly detecting low-concentration ethylene oxide gas at normal temperature, the reaction rate of the color reaction must be accelerated. Factors influencing the reaction rate include the nature of the reactants themselves, the reaction temperature, the concentration of the reactants, the influence of the catalyst, the solvent, etc.
(3) And realizing semi-quantitative detection. The method for semi-quantitatively detecting gas by using the test paper mainly comprises the following two methods: firstly, the test paper is exposed in the atmosphere to be detected, and the colors generated by the test paper are different because the test paper reacts in the atmosphere with different concentrations of the gas to be detected within the same time (or after the test paper reaches the reaction limit), and the approximate concentration can be obtained by comparing the colors with the colors of a colorimetric card; and secondly, the test paper is made into a long strip and is arranged in a thin glass tube with an opening at one end, then the glass tube is exposed in the atmosphere to be tested, and the concentration of the gas to be tested can be calculated according to the length because the diffusion speed of the gas to be tested with different concentrations into the glass tube is different and the discoloration length of the test paper strip is different in the same time.
(4) And (4) eliminating interference factors. In order to ensure the accuracy of the detection result, the influence of various environmental factors on the detection result needs to be determined, including: storage conditions, temperature, humidity, common gases, etc.
In view of the above technical problems, the present invention provides the following technical solutions.
(1) And (4) selecting paper. Considering that the test strip preparation process may require multiple soakings in a drying process, and the requirement of the test strip for the reaction substrate loading, a strong absorbent paper needs to be selected. The Whatman 3MM CHR chromatography paper is used as a carrier for screening.
(2) The test paper manufacturing method comprises the following steps: the color-developing agent (pyridine derivative), auxiliary agent, and the like described below were prepared as ethanol solutions at a certain concentration, respectively. Then, respectively and uniformly dripping the ethanol solution on test paper, and air-drying; and (4) dropwise adding again and air drying when necessary, and repeating for multiple times. After drying, the mixture is stored in a dryer in a sealed and dark place.
(3) And (4) selecting a color developing agent. Can be selected from pyridine derivatives such as 4-methylquinoline and 4- (4-nitrobenzyl) pyridine. 4- (4-nitrobenzyl) pyridine can change color after contacting ethylene oxide for a plurality of minutes at normal temperature, but 4-methylquinoline can not be observed obviously for a long time. From the viewpoint of the reaction rate, 4- (4-nitrobenzyl) pyridine is preferably selected.
(4) And (4) selecting an auxiliary reagent. Analysis on the reaction mechanism shows that the enhancement of the nucleophilicity of 4- (4-nitrobenzyl) pyridine or the enhancement of the electrophilicity of ethylene oxide is helpful for increasing the rate of the ring-opening reaction. For this purpose, Lewis acids can be used to complex with ethylene oxide, or strongly basic substances can be added, or polar aprotic solvents can be used to increase the nucleophilicity of 4- (4-nitrobenzyl) pyridine. The specific scheme is as follows:
i) lewis acids, obtainable from boron trifluoride etherate (BF)3·Et2O), anhydrous aluminum chloride (AlCl)3) To select. From the practical effect, after the Lewis acid is added into the system, the Lewis acid firstly complexes with the 4- (4-nitrobenzyl) pyridine to form crystal precipitation, and after the complexation, the nucleophilicity of the 4- (4-nitrobenzyl) pyridine is reduced, so that the ring-opening reaction rate of the 4- (4-nitrobenzyl) pyridine and the ethylene oxide is reduced.
ii) the alkaline substance can be selected from caustic (NaOH, KOH, etc.) or a highly hindered strong base (e.g.: (CH)3)3CONa，NaN(CH3)2Etc.). From the practical effect, the effect of the strong alkali with large steric hindrance is better than that of caustic alkali, and the effect of accelerating the reaction rate can be obtained under the condition of smaller addition amount.
iii) the polar aprotic solvent may be selected from acetonitrile, dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, and the like. In practical terms, higher boiling solvents (e.g., hexamethylphosphoric triamide) are more effective than lower boiling solvents (e.g., acetonitrile).
The specific implementation mode is as follows:
the present invention is illustrated but not limited by the following examples.
Example 1 control experiment
Preparing 5 wt% of 4-methylEthanol solution of quinolinyl, 2 wt% BF3·Et2Oethanol solution and 5 wt% AlCl3Ethanol solution. The ethanol solution was dropped onto a 2X 5cm filter paper in this order and then air-dried. The dropping and the air drying are repeated for a plurality of times according to the requirement. The test paper was exposed to an ethylene oxide atmosphere of 2% (by volume) and observed for discoloration. The results obtained are shown in Table 2.
TABLE 24 color development of methylquinolines as color developers
Example 2
5 wt% 4- (4-nitrobenzyl) pyridine ethanol solution is prepared, and is uniformly dropped on a filter paper of 2X 5cm, and is naturally dried in the air. The test paper was exposed to an ethylene oxide atmosphere of 2% (by volume) and observed for discoloration. The results obtained are shown in Table 3.
TABLE 34 color development of (4-nitrobenzyl) pyridine as developer
The phenomenon that 4- (4-nitrobenzyl) pyridine is easier to generate ring-opening reaction with ethylene oxide to cause color change than 4-methylquinoline is demonstrated, so that the pyridine is more suitable for being used as the color developing agent of the invention.
Example 3
Preparing 5 wt% 4-methylquinoline ethanol solution and 2 wt% BF3·Et2Oethanol solution and 5 wt% AlCl3Ethanol solution. The solution was dropped onto a 2X 5cm filter paper in this order and air-dried. The test paper was exposed to an ethylene oxide atmosphere of 2% (by volume) and observed for discoloration. The results obtained are shown in Table 4.
TABLE 44 color development of (4-nitrobenzyl) pyridine as developer
The phenomenon shows that after the Lewis acid is added into the system, the Lewis acid is firstly complexed with the 4- (4-nitrobenzyl) pyridine to form crystal precipitation, and after the complexing, the nucleophilicity of the 4- (4-nitrobenzyl) pyridine is reduced, so that the ring-opening reaction rate of the 4- (4-nitrobenzyl) pyridine and the ethylene oxide is reduced.
Example 4
Preparing 5 wt% 4- (4-nitrobenzyl) pyridine ethanol solution, 2 wt% NaOH ethanol solution and 2 wt% NaN (CH)3)2The ethanol solution was dropped onto 2X 5cm filter paper in sequence and air-dried. The test paper was exposed to an ethylene oxide atmosphere of 2% (by volume) and observed for discoloration. The results obtained are shown in Table 5.
TABLE 54 color development of (4-nitrobenzyl) pyridine as developer
The phenomenon shows that the ring-opening reaction rate of the ethylene oxide and the 4- (4-nitrobenzyl) pyridine can be improved by adding strong base or strong base with large steric hindrance into a reaction system, so that the color development time is shortened. Among them, the alkali with strong steric hindrance has better effect than caustic alkali.
Example 5
Preparing 5 wt% 4- (4-nitrobenzyl) pyridine ethanol solution and 2 wt% NaN (CH)3)2An ethanol solution, a 5 wt% acetonitrile ethanol solution and a 2 wt% hexamethylphosphoric triamide ethanol solution were uniformly dropped in this order onto a 2X 5cm filter paper, and then air-dried. The test paper was exposed to an ethylene oxide atmosphere of 2% (by volume) and observed for discoloration. The results obtained are shown in Table 5.
TABLE 54 color development of (4-nitrobenzyl) pyridine as developer
The results show that the ring-opening reaction rate of the ethylene oxide and the 4- (4-nitrobenzyl) pyridine can be improved by simultaneously adding the large steric hindrance strong and polar aprotic solvent into the reaction system, so that the color development time is further shortened. Wherein, hexamethylphosphoric triamide with higher boiling point has better effect than acetonitrile with lower boiling point.
Claims (6)
1. A method for preparing test paper for quickly detecting epoxy ethane features that pyridine derivative which can generate ring-opening discolouring reaction with epoxy ethane and auxiliary reagent for increasing reaction rate are pre-loaded on the test paper.
2. A method for making a test strip for rapid detection of ethylene oxide as claimed in claim 1, comprising at least the steps of: respectively preparing a pyridine derivative and an auxiliary reagent into ethanol solutions according to certain concentrations; respectively and uniformly dripping the ethanol solution on tough paper with strong water absorption, and air-drying; dripping again and air drying when necessary, and repeating for several times; drying, placing in dry place, sealing, and storing in dark place.
3. The method for preparing test paper for rapid detection of ethylene oxide according to claim 1, wherein the pyridine derivative is selected from 4-methylquinoline and 4- (4-nitrobenzyl) pyridine; from the viewpoint of faster reaction rate, 4- (4-nitrobenzyl) pyridine is preferably selected.
4. The method of claim 1 wherein the auxiliary reagent comprises a Lewis acid selected from boron trifluoride etherate (BF)3·Et2O), anhydrous aluminum chloride (AlCl)3) To select.
5. A method of making a rapid test strip for the detection of ethylene oxide as in claim 1, wherein the auxiliary reagent comprises an alkaline substance selected from the group consisting of caustic alkali and strong bases with high steric hindrance; from the viewpoint of a smaller amount of addition, a strong base having a large steric hindrance is preferable.
6. A method for making a rapid test strip for ethylene oxide as claimed in claim 1, wherein the auxiliary reagent further comprises a polar aprotic solvent selected from acetonitrile, dimethylformamide, dimethylsulfoxide, hexamethylphosphoric triamide. From the practical effect, the high boiling point solvent, such as: hexamethylphosphoric triamide is preferred.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3992154A (en) * | 1975-12-22 | 1976-11-16 | Sybron Corporation | Ethylene oxide sterilization indicator |
| CN101029877A (en) * | 2006-02-27 | 2007-09-05 | 权力敏 | Sterilizing gas indicating card |
| CN101463383A (en) * | 2007-12-19 | 2009-06-24 | 曲奕 | Sterilizing gas rapid detection reagent label |
| CN111378328A (en) * | 2020-04-23 | 2020-07-07 | 南京巨鲨显示科技有限公司 | Indicator and indicator card for low-temperature ethylene oxide sterilization |
| CN111410869A (en) * | 2020-04-23 | 2020-07-14 | 南京巨鲨显示科技有限公司 | Indicator and indicator label for low-temperature ethylene oxide sterilization |
-
2020
- 2020-07-28 CN CN202010741532.6A patent/CN111965182A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3992154A (en) * | 1975-12-22 | 1976-11-16 | Sybron Corporation | Ethylene oxide sterilization indicator |
| CN101029877A (en) * | 2006-02-27 | 2007-09-05 | 权力敏 | Sterilizing gas indicating card |
| CN101463383A (en) * | 2007-12-19 | 2009-06-24 | 曲奕 | Sterilizing gas rapid detection reagent label |
| CN111378328A (en) * | 2020-04-23 | 2020-07-07 | 南京巨鲨显示科技有限公司 | Indicator and indicator card for low-temperature ethylene oxide sterilization |
| CN111410869A (en) * | 2020-04-23 | 2020-07-14 | 南京巨鲨显示科技有限公司 | Indicator and indicator label for low-temperature ethylene oxide sterilization |
Non-Patent Citations (2)
| Title |
|---|
| 吕萍等: ""有机反应中的亲核性和碱性"", 《大学化学》 * |
| 王庆培等: ""消毒效果的快速评价方法研究进展"", 《中国消毒学杂志》 * |
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Application publication date: 20201120 |