A method for synthesizing aldehyde compounds

Abstract

The application discloses a kind of synthesis aldehyde compound's method, it is related to green synthesis chemical field, the present application is synthesized by aldehyde synthesis device, the aldehyde compound synthesis device includes ionization source channel, gas sampling channel and mass spectrometer;First, ionization source channel is ionized into water radical cation cluster (H2O) 2 +· Ion;Then water radical cation cluster (H2O) 2 +· Ion and the positive alkane steam reacted by gas sampling channel output, produce alkane peroxide intermediate and aldehyde ion, finally using mass spectrometer to detect product, the present application provides a kind of green environmental protection synthesis aldehyde compound's method, can make a supplement to the existing synthesis aldehyde technical method, and reaction device is simple, need not catalyst, fast and efficient, high yield.

Description

Technical Field

[0001] This invention relates to the field of green synthetic chemistry, and more specifically to a method for synthesizing aldehyde compounds. Background Technology

[0002] Water-free radical cations possess high catalytic activity and good redox capabilities, making them well-suited for synthetic applications. For example, they can accelerate chemical reactions, enabling reactions that are difficult to perform in the liquid or gas phase. Recent years have seen extensive research on water-free radical cations, such as their reaction with benzene to synthesize phenol and release hydrogen. Since water-free radical cations are highly reactive oxidants with strong electric fields, and aldehydes are ubiquitous in nature and widely used in various fields, aldehyde synthesis has significant practical value and is technically mature. However, there is relatively little information available on aldehyde synthesis. This invention utilizes the strong reactivity of water-free radical cations to directly oxidize n-alkanes to alkane peroxides, which are then dehydrated to form aldehydes. The apparatus and synthetic approach presented here show great promise in the synthesis of aldehydes. Alkanes are common precursors in everyday life, primarily composed of C and H atoms, and are important organic compounds. Therefore, research on synthesizing substances using alkanes as precursors is highly valuable. Currently, the synthesis of such substances rarely involves the field of aldehydes. It is more common in the synthesis of some materials by using the C and H bonds in alkane compounds to graft some groups, thereby changing the activity of n-alkanes and synthesizing some probe compounds and organic materials.

[0003] To date, the synthesis of aldehydes has been relatively limited. Therefore, there is a need to develop simpler and more environmentally friendly methods and apparatus for synthesizing straight-chain aldehydes. Summary of the Invention

[0004] The purpose of this invention is to provide an apparatus and method for synthesizing alkane peroxide intermediates and straight-chain aldehyde compounds, so as to solve the problems of difficult and costly synthesis of aldehydes in the prior art. This invention provides simple, green and environmentally friendly, and low-cost conditions for synthesizing alkane peroxides and their dehydration product aldehyde compounds.

[0005] This invention discloses a method for synthesizing aldehyde compounds, which is prepared using an aldehyde synthesis apparatus, including an ionization source channel, a gas injection channel, and a mass spectrometer.

[0006] First, the ionization source channel ionizes water molecules into water radical cation clusters (H2O)2. +· Ions; then water free radical cation clusters (H2O)2 +· Ions react with n-alkane vapor output from the gas injection channel to produce alkane peroxide intermediates, which are then dehydrated to form straight-chain aldehyde compounds. Finally, the products are detected by mass spectrometry.

[0007] As a preferred embodiment of the present invention, the flow rate of the n-alkane vapor is 0.3-0.5 mL / min.

[0008] As a preferred embodiment of the present invention, the n-alkane includes C6H 12 C 11 H 24 C 13 H 28 C 14 H 30 C 19 H 40 C 20 H 42 At least one of them.

[0009] In a preferred embodiment of the present invention, the ionization channel includes a first carrier gas channel, a first sample release device, a high-voltage source, a capillary tube, and a discharge needle, wherein the discharge needle is fixed in the capillary tube, and the high-voltage source is used to provide a certain high voltage to the discharge needle; and / or;

[0010] The ionization channel also includes a first flow meter, which is located on the first carrier gas channel.

[0011] As a preferred embodiment of the present invention

[0012] The gas injection channel includes a carrier gas source, a second carrier gas channel, a second flow meter, and a second sample release device;

[0013] The carrier gas source is connected to the second carrier gas channel, which is connected to the second flow meter via a hose. The second flow meter is connected to the outlet hose and then to the second sample release device. The second sample release device is connected to the Peck tube, which is perpendicular to the discharge needle at an angle of 50°-70° and is 2-3 cm away from the mass spectrometer inlet.

[0014] As a preferred embodiment of the present invention, the discharge needle is a stainless steel conical discharge needle.

[0015] As a preferred embodiment of the present invention, the specific steps include:

[0016] Close the gas inlet channel, open the carrier gas switch of the first carrier gas channel of the ionization channel, adjust the gas flow rate of the first flow meter, add a certain volume of pure water to the sample release device of the ionization channel, so that the carrier gas carrying water vapor can reach the tip of the discharge needle through the pipeline; at the same time, set the high voltage source parameters to apply a high voltage of 1.5-2.5 kV to the discharge needle to prepare a high abundance of water radical cations (H2O)2. +· ;

[0017] Simultaneously, the carrier gas source in the gas injection channel is turned on. The carrier gas passes through a hose and a second flow meter. The flow rate of the carrier gas is controlled by adjusting the size of the second flow meter. n-Alkanes are added to the sample release device. Driven by the carrier gas argon, the n-alkanes are carried by the carrier gas in vapor form to the outlet of the pipeline, where they rapidly react with the water radical cations (H₂O) formed in the ionization channel. +· The interaction in three-dimensional space produces alkane peroxides, which are then dehydrated to form straight-chain aldehyde compounds.

[0018] Taking n-hexane as an example, the reaction principle is as follows:

[0019]

[0020] As a preferred embodiment of the present invention, the detection of the product using a mass spectrometer includes the following steps:

[0021] Using deuterium labeling and isotope 18 The O labeling replaced the pure water in the sample device within the ionization channel with D2O and H2, respectively. 18 With other conditions remaining constant, signals at m / z 38 and m / z 40 were clearly observed on the mass spectrometer, representing D substitution and [other conditions not specified]. 18 The O-substituted isotopic water radical cations were analyzed using primary and secondary mass spectrometry data to determine that the ions with mass numbers increased by 13 Da and 31 Da were complexes formed by the interaction of water radical cations with n-alkane compounds.

[0022] The present invention has the following beneficial effects:

[0023] The apparatus and method described above for synthesizing straight-chain aldehydes and alkane peroxide intermediates offer several advantages. When air humidity is low, a carrier gas can be used to introduce water vapor; when air humidity is high, water vapor in the air can be directly ionized without a carrier gas, making the process convenient and simple. By adjusting the voltage, the abundance of water radical cation clusters generated by the ionization of water vapor can be controlled. These water radical cation clusters interact with n-alkane compounds to produce abundant alkane peroxide intermediates and the resulting aldehydes formed through dehydration. The entire apparatus is quick, simple, and inexpensive to modify, requiring no sample pretreatment or catalysts. The entire analytical process is highly efficient and rapid, and the reaction can proceed quickly at room temperature and pressure. Using water as the reaction carrier, it is green, pollution-free, energy-saving, and environmentally friendly. The reaction time between water radical cation clusters and n-alkane compounds is very fast, enabling high-yield synthesis of aldehydes and alkane peroxide intermediates in a short time. This is of great significance for the rapid synthesis of alkane peroxide intermediates and aldehydes. This invention provides a rapid, simple, catalyst-free, and low-cost method and apparatus for the synthesis of alkane peroxide intermediates and aldehydes. Attached Figure Description

[0024] The above and / or additional aspects and advantages of the present invention will become apparent and readily understood from the description of the embodiments taken in conjunction with the following drawings, in which:

[0025] Figure 1 This is a schematic diagram of the linear aldehyde synthesis apparatus of the present invention;

[0026] Figure 2 This is the mass spectrum of water radical cations prepared by regulating the charge transfer mechanism in Example 1 (gas injection channel closed);

[0027] Figure 3 The primary and secondary mass spectra of the hexane peroxide intermediate and the straight-chain hexanal ion products (m / z 117 and m / z 99) formed by the interaction of water radical cations formed in the ionization channel with n-hexane, as well as the corresponding isotope labeling diagrams;

[0028] Figure 4 Total ion chromatogram and selected ion chromatogram for the interaction of water radical cations with n-hexane;

[0029] Figure 5 Structural diagrams of different n-alkane compounds and mass spectra of the products of their reaction with water free radical cations;

[0030] Figure 6 The figure shows the results of the optimized conditions for the reaction involving n-alkane, with the n-alkane flow rate (a), the distance between the sample outlet and the mass spectrometer port (b), the capillary temperature (c), and the applied voltage (d) respectively. Detailed Implementation

[0031] To make the objectives, features, and advantages of this invention more readily apparent, the specific embodiments of the invention are described in detail below with reference to the accompanying drawings. Several examples of the invention are shown in the drawings. However, the invention can be presented in many different forms and is not limited to the examples described herein. Rather, these examples are provided to provide a more transparent and comprehensive demonstration of the invention and to enhance the reader's understanding of it.

[0032] It should be noted that when an element is referred to as being "fixed to" or "attached to" another element, it can be directly on, enclosed in, or enclosed by another element. When an element is considered to be "connected to" another element, it can be directly connected to the other element or there may be an intervening element present. The terms "vertical," "horizontal," "left," "right," "upper," "lower," and similar expressions used herein are for illustrative purposes only and are not intended to indicate or imply that the device or element referred to must have a specific orientation, be constructed and operated in a specific orientation, and therefore should not be construed as limiting the invention.

[0033] In this invention, unless otherwise explicitly specified and limited, the terms "installation," "connection," "linking," "fixing," etc., should be interpreted broadly. For example, they can refer to a fixed connection, a detachable connection, or an integral connection; they can refer to a mechanical connection or an electrical connection; they can refer to a direct connection or an indirect connection through an intermediate medium; and they can refer to the internal communication between two components. Those skilled in the art can understand the specific meaning of the above terms in this invention according to the specific circumstances. The term "and / or" as used herein includes any and all combinations of one or more of the related listed items.

[0034] Please see Figure 1 An embodiment of the present invention provides an apparatus for synthesizing alkane peroxide intermediates and straight-chain aldehyde compounds, comprising an ionization channel, a gas injection channel, and a mass spectrometer 13;

[0035] The ionization channel includes a discharge needle 4, a first conduit 10, a first carrier gas channel 9, a high-pressure source 5, a capillary tube 3, and a first sample release device 2.

[0036] The first sample placement device 2 can be used to store samples or pure water, etc. The first carrier gas channel 9 is inserted into the sample placement device 2 and is used to provide an inert gas, such as argon, to the sample placement device 2. The purpose of providing an inert gas in the ionization channel is to carry out the water and, at the same time, to avoid interference from other impurities when the water is ionized at the tip of the discharge needle 4.

[0037] One end of the first conduit 10 is inserted into the first sample placement device 2, and the other end of the first conduit 10 is connected to the capillary 3 via a first flow meter, such as a two-way valve (not shown). The discharge needle 4 is disposed in the capillary 3. The high-voltage source 5 is used to provide high voltage to the discharge needle 4, for example, applying a high voltage of 2kV to the discharge needle 4 to ionize water vapor and generate water free radical cation clusters through corona discharge. Specifically, the discharge needle 4 is a stainless steel conical discharge needle.

[0038] The function of the first sample release device 2 in the ionization channel is to hold water and provide water vapor for ionization to generate water free radical cations. The function of the second sample release device 7 in the gas injection channel is to hold and store n-alkane samples to enhance the three-dimensional interaction between sample vapor and water free radical cations in front of the mass spectrometer port, thereby reacting to synthesize straight-chain aldehydes and alkane peroxide intermediates.

[0039] The capillary tube 3 serves two purposes: (1) to wrap the discharge needle 4 and prevent the entire discharge needle 4 from being exposed; and (2) to introduce a neutral water flow so that the water flow can fully interact and contact with the discharge needle 4.

[0040] The gas injection channel includes a carrier gas source, a carrier gas channel 11, a second flow meter 6, and a second sample release device 7;

[0041] The carrier gas source is connected to the carrier gas channel 11, the carrier gas channel 11 is connected to the second flow meter 6, and the second flow meter 6 is connected to the second sample release device 7 via a hose. Specifically, a Peck tube can be used to connect to the outlet of the second sample release device 7. The second flow meter 6 is used to control the magnitude of the carrier gas flow.

[0042] The carrier gas source can be argon, an inert gas. The second flow meter 6 is used to control the carrier gas flow rate and keep it stable. The carrier gas channel 11 is used to transport the gas flow, thereby introducing the chemical components and water vapor in the carrier gas to the front end of the mass spectrometer 13 inlet. The carrier gas can also be other types of inert gas.

[0043] The outlet end of the capillary tube 3 is located at the front end of the inlet of the mass spectrometer 13, and the distance from the front end of the inlet of the mass spectrometer 13 is a = 15mm to 20mm. The outlet end of the Peck tube 8 is also located at the front end of the inlet of the mass spectrometer 13, and the distance from the front end of the inlet of the mass spectrometer 13 is a = 15mm to 20mm. The ports of the two are vertically parallel in space. The distance between the outlet end of the capillary tube 3 and the outlet end of the Peck tube 8 is b = 3 to 5mm. The angle between the outlet end of the capillary tube 3 and the front end of the inlet of the mass spectrometer 13 is... α is 150°, and the angle α between the outlet end of the Peck tube 8 and the front end of the inlet of the mass spectrometer 13 is also 150°. The angle β between the outlet end of the capillary 3 and the outlet end of the Peck tube 8 is 60°. The outlet ends of the capillary 3, the outlet ends of the Peck tube 8, and the front end of the inlet of the mass spectrometer 13 are all in a sealed device. This allows the water free radical cation clusters formed in the ionization channel and the n-alkane compounds in the carrier gas to converge and fully interact at the front end of the inlet of the mass spectrometer 13, minimizing sample loss and saving economic costs.

[0044] Preferably, the ionization channel further includes a first flow meter 1, which is disposed on the carrier gas channel 9 and is used to control the flow rate of the carrier gas in the ionization channel.

[0045] Based on the above apparatus, a method for synthesizing straight-chain aldehydes and alkane peroxide compounds includes:

[0046] Inert gas is introduced into the water-containing sample device 2 through the first carrier gas channel 9 to form an inert gas containing water vapor. At the same time, the carrier gas introduces the water in the sample device in the form of gas to the front end of the inlet of the mass spectrometer 13 through the first carrier gas channel 9.

[0047] A high voltage of 1.5 to 2.5 kV is applied to the tip of the discharge needle 4 through the high voltage source 5, so that the water free radical cations are the base peaks. Moist water vapor is introduced into the tip of the discharge needle 4 through the pipeline to generate water free radical cation clusters through corona discharge ionization.

[0048] The formed water free radical cation clusters interact with the n-alkane sample molecules carried by the carrier gas in the gas injection channel in three-dimensional space, producing aldehyde ion and alkane peroxide ion base peaks; in specific applications, the flow rate of the n-alkane sample is controlled at 0.3-0.5 mL / min.

[0049] The formed aldehyde-containing ion and alkane peroxide ion products are detected by the mass spectrometer 13. The mass spectrometer 13 is used to analyze them to obtain characteristic ion fragments whose structures can be determined, thereby realizing the structural analysis of the synthesis of straight-chain aldehyde and alkane peroxide intermediates.

[0050] The present invention will be further described below through various embodiments. Unless otherwise specified, the conditions are the optimized conditions used in this experiment.

[0051] Example 1

[0052] use Figure 1 The apparatus shown, with the gas channel closed, introduces moist water vapor into the ionization channel to the tip of the discharge needle while simultaneously applying a high voltage of 2 kV to the discharge needle, thus preparing highly abundant water radical cation clusters (H2O)2. +· Ion m / z 36, specifically as follows Figure 2 As shown. Where m / z54 is (H2O)3 +· The ion with m / z 55 is (H₂O)₃H. + ion.

[0053] Example 2

[0054] use Figure 1 The apparatus shown involves adding n-hexane (Mw86) sample to the sample release device in the gas injection channel. In this embodiment, the flow rate of n-alkane is controlled at 0.3 mL / min. Simultaneously, a high voltage of 2 kV is applied to the discharge needle, causing it to react with the water radical cations (H2O)2 formed by the ionization channel. +· The reaction occurs through three-dimensional interaction, further producing product ions with mass numbers increasing by 13 Da and 31 Da, m / z 99 and m / z 117, respectively. Preliminary inference suggests these are hexanal ions and hexane peroxide intermediate ions. Figure 3 (as shown in c). Further methods include deuterium labeling and isotope labeling. 18 The O-labeling experiment replaced water with D2O and H2. 18With other conditions remaining constant, analysis of the corresponding primary mass spectrometry and CID data confirmed that the ion with a mass number increase of 13 Da is H₂O. +· The hexanal formed by the reaction with n-hexane, while the ion with a mass number increase of 31 Da is a product of the reaction between alkane and water radical cations, an intermediate ion of alkane peroxide. Further analysis using a secondary mass spectrum at m / z 117... Figure 3 (As shown in e), the secondary mass spectrum and isotopes of m / z 117 18 Comparative analysis of the second-order mass spectra at m / z 119 formed by O-labeling experiments revealed that m / z 117 primarily undergoes dehydrogenation after collisions to form ionized hexanal at m / z 99. Figure 3 (as shown in e); m / z 118 mainly loses HOD after collisions, forming hexanal m / z 99 after HOD loss; m / z 119 mainly loses H2 after collisions. 18 O forms hexanal- 18 The O ion has a m / z of 100. Therefore, the ions with mass numbers increasing by 13 Da and 31 Da can be identified as H₂O. +· Hexanal, a product of interaction with n-hexane, and alkane peroxide intermediates generated by the reaction of n-hexane with water free radical cations.

[0055] Please see Figure 2 and Figure 3 , Figure 3 This demonstrates the process by which water radical cations interact with n-hexane to form hexanal and hexane peroxide intermediates, and in tandem mass spectrometry, the intermediate compounds further fragment and lose H2O to form ionized hexanal (m / z 99 and (...)). Figure 5 b).

[0056] Please see Figure 4 , Figure 4 The diagram illustrates the total ion chromatogram (TIC) and selected ion chromatogram (EIC) obtained by first introducing water vapor into the ionization channel with the gas inlet channel closed, and then opening the gas inlet channel and using a carrier gas to introduce a certain amount of hexane vapor to react with water radical cations. It can be observed that after introducing the hexane sample, m / z 36 decreases rapidly, while m / z 117 and m / z 99 increase rapidly. This indicates that m / z 36 is reacted away to form new m / z 117 and m / z 99.

[0057] Example 3

[0058] use Figure 1The apparatus shown employs the same method and mass spectrometry experimental conditions as in Example 2. Hexane is added to the sample device in the gas injection channel to control the carrier gas flow rate using a flow meter. This allows for a good linear relationship between the reaction of hexane and hydrated radical cations to form a signal m / z 117 product under different carrier gas flow rates. The results are referenced. Figure 6 a.

[0059] Additionally, the distance between the sample outlet and the mass spectrometer outlet ( Figure 6 b) Capillary temperature Figure 6 c) and applied voltage ( Figure 6 d) A single-factor study was conducted, and the results are shown in the figure, revealing the optimal conditions.

[0060] Example 4

[0061] use Figure 1 The apparatus shown is used to evaluate the generality of the method. The same experiments were performed on a series of n-alkanes under the same conditions as in Example 2. The structures of the n-alkanes are as follows: Figure 5 As shown (C respectively) 11 H 24 C 13 H 28 C 14 H 30 C 19 H 40 C 20 H 42 First, close the gas inlet channel, add water to the sample release device in the ionization channel, open the gas inlet channel, and add n-alkane samples to the sample device. Signals from the interaction of various types of n-alkane compounds with hydrated free radical cations can be obtained. This indicates that n-alkane compounds readily form alkane peroxide intermediates and straight-chain alkane aldehyde ions with hydrated free radical cations. This device is suitable for the rapid synthesis of corresponding straight-chain aldehydes and alkane peroxides from n-alkane compounds and is expected to be applied in the field of pharmaceutical synthesis, etc.

[0062] In summary, the aforementioned apparatus and method for synthesizing corresponding aldehydes and alkane peroxides from n-alkanes offer several advantages. When air humidity is low, a carrier gas can be used to carry water vapor; when air humidity is high, no carrier gas is needed, as water vapor in the air can be directly ionized, making it convenient to use. By adjusting the voltage, water vapor ionization generates a large number of water radical cation clusters. These clusters interact with n-alkanes in the carrier gas to produce numerous aldehyde and alkane peroxide intermediate compound free radical cation product peaks. The entire apparatus is simple, has low modification costs, requires no catalyst or sample pretreatment, and the entire analysis process takes less than one minute. It can be performed at room temperature and pressure. Using water as a carrier, the reaction between water radical cation clusters and n-alkanes is green and pollution-free, with a fast reaction time, enabling efficient synthesis. This method is of great significance for the rapid synthesis of aldehydes and alkane peroxides from alkanes in a carrier gas using free radical cations.

[0063] In the description of this specification, references to terms such as "one embodiment," "some embodiments," "embodiment," "specific embodiment," or "some embodiments," etc., indicate that a specific feature, structure, material, or characteristic described in connection with that embodiment or embodiment is included in at least one embodiment or embodiment of the invention. In this specification, the illustrative expressions of the above terms do not necessarily refer to the same embodiment or embodiment. Furthermore, the specific features, structures, materials, or characteristics described may be combined in any suitable manner in one or more embodiments or embodiments.

[0064] The embodiments described above are merely illustrative of several implementations of the present invention, and while the descriptions are specific and detailed, they should not be construed as limiting the scope of the present invention. It should be noted that those skilled in the art can make various modifications and improvements without departing from the concept of the present invention, and these modifications and improvements all fall within the scope of protection of the present invention. Therefore, the scope of protection of this patent should be determined by the appended claims.

Claims

1. A method of synthesizing an aldehyde compound, characterized by, The aldehyde is synthesized by an aldehyde synthesis device, and the aldehyde synthesis device comprises an ionization channel, a gas sampling channel and a mass spectrometer; First, the ionization channel ionizes water molecules into water radical cation clusters (H2O)2 +· ions; then the water radical cation clusters (H2O)2 +· react with the positive alkane vapor output by the gas sampling channel to produce alkane peroxide and aldehyde compound ion products, and finally the products are detected by a mass spectrometer; The flow rate of the normal alkane steam is 0.3-0.5 mL / min. said n-alkane is selected from n-hexane, C 11 H 24 , C 13 H 28 , C 14 H 30 , C 19 H 40 , C 20 H 42 at least one of The ionization channel comprises a first carrier gas channel, a first sample discharge device, a high-voltage source, a capillary and a discharge needle, the discharge needle is fixed in the capillary, and the high-voltage source is used to provide a high voltage of 2-2.5 kV to the discharge needle.

2. The method for synthesizing aldehyde compounds according to claim 1, wherein, The ionization channel further comprises a first flow meter, and the first flow meter is arranged on the first carrier gas channel.

3. The method for synthesizing aldehyde compounds according to claim 2, wherein, The gas sampling channel comprises a carrier gas source, a second carrier gas channel, a second flow meter, and a second sample discharge device. The carrier gas source is connected to the second carrier gas channel, the second carrier gas channel is connected to the second flow meter through a hose, the second flow meter is connected to an outlet hose and connected to the second sample discharge device, the second sample discharge device is connected to a peck tube, the peck tube is vertically parallel to the discharge needle at an angle of 50-70°, and the distance between the peck tube and the inlet of the mass spectrometer is 2-3 cm.

4. The method of claim 2, wherein the aldehyde compound is synthesized by the reaction of the compound of formula (2) with the compound of formula (3) in the presence of a base. The discharge needle is a conical stainless steel discharge needle.

5. The method of claim 3, wherein the aldehyde compound is synthesized by the reaction of the compound of formula (2) with the compound of formula (3) in the presence of a base. Specifically comprising the following steps: Close the gas inlet channel, open the carrier gas switch of the first carrier gas channel of the ionization channel, adjust the gas flow size of the first flow meter, add a certain volume of pure water in the first sample device of the ionization channel, so that the carrier gas carrying water vapor passes through the pipeline to the needle tip of the discharge needle; at the same time, set the high-voltage source parameter size, apply a high voltage of 2-2.5kV to the discharge needle, and prepare a high-abundance water radical cation (H2O)2 +· ; At the same time, open the carrier gas source of the gas inlet channel, the carrier gas passes through the second flow meter, and the size of the second flow meter is adjusted to control the carrier gas flow rate. Add normal alkanes in the second sampling device. The normal alkanes are carried by the carrier gas argon and reach the pipeline outlet in the form of vapor, and quickly form water radical cations (H2O)2 with the ionization channel +· In three-dimensional space interaction, alkane peroxide is generated, and then dehydrated to form aldehyde compound ions.

6. The method of claim 5, wherein the aldehyde compound is synthesized by the reaction of the compound of formula (2) with the compound of formula (3) in the presence of a base. The product is detected by using the mass spectrometer, and the detection comprises the following steps: Isotopically deuterium labeled and isotopically 18 O labeled water in the ionization channel and the first sample device were replaced by D2O and H2O, respectively 18 O, other conditions remain unchanged, m / z 38 and m / z 40 signals were obviously seen on the mass spectrometer, respectively, D substitution and 18 O, substitution of isotopic water radical cation, and through the corresponding mass spectrum data and secondary mass spectrum data analysis to determine the mass number of 13 Da and 31 Da ions are water radical cation and the formation of the complex of the interaction of n-alkane compounds.

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