CN1641071A - Alkyl hydroxylamine and its salt electrochemical synthesis method - Google Patents

Abstract

The invention relates to an electrochemical synthesis method of alkyl hydroxylamine containing 1 to 6 carbon atoms and its salt, especially an electrochemical synthesis method of isopropyl hydroxylamine salt. The method uses the corresponding nitro-substituted alkanes as raw materials, adopts a plate-and-frame diaphragm type electrolytic cell, uses a cationic homogeneous membrane as a diaphragm, and uses an aqueous solution of sulfuric acid or hydrochloric acid with a concentration of 5 to 35% as electrolysis for the cathode or anode. The electrolysis product containing alkyl hydroxylamine salt is synthesized through electrolytic reduction reaction, the electrolysis product is separated and purified to obtain the alkyl hydroxylamine salt, and the generated alkyl hydroxylamine salt is neutralized to generate the corresponding alkyl hydroxylamine. The method has a short synthesis route, simple process flow, can synthesize products in one step, reduces production links, and reduces production costs; the Faraday efficiency of the synthesis process can be as high as more than 90%, the reaction conditions are mild, the control is simple, and the production process is basically pollution-free; The product has high purity, the raw material is easy to get, and the price is cheap.

Description

A kind of electrochemical synthesis method of alkylhydroxylamine and salt thereof

(1) Technical field

The invention relates to an electrochemical synthesis method of alkyl hydroxylamine containing 1 to 6 carbon atoms and its salt, especially an electrochemical synthesis method of isopropyl hydroxylamine salt.

(2) Background technology

Alkyl hydroxylamines containing 1 to 6 carbon atoms and their salts, especially isopropyl hydroxylamine salts, are important intermediates in organic synthesis and are widely used in the synthesis of pesticides, medicines, cosmetics, etc. or as additives.

In the prior art, isopropyl hydroxylamine and its salts are generally prepared by chemical oxidation of 2-propylamine oxidation and catalytic hydrogenation to reduce 2-nitropropane. The reaction of 2-propylamine oxidation is difficult to control, the side reactions are complicated, and the yield Low, poor product quality; Catalytic hydrogenation requires the use of precious metals as catalysts, and the catalysts are easily poisoned during the reaction process, which increases the cost of industrial production. Both methods are difficult to industrialize, and there are no relevant research reports in China , and there is no manufacturer to produce, the product has long been dependent on imports, and the price is high, which limits the wide application of this product. Containing the preparation of the alkyl hydroxylamine salt of 1～6 carbon atoms, also exists above-mentioned problem equally.

(3) Contents of the invention

In order to solve the shortcomings of high production cost, poor product quality and complex synthesis process of existing chemical synthesis of isopropyl hydroxylamine salt, the present invention provides a high-efficiency, low-cost and low-pollution electrochemical synthesis method of isopropyl hydroxylamine salt , This method is also suitable for the synthesis of alkyl hydroxylamine salts containing 1 to 6 carbon atoms and the preparation of alkyl hydroxylamines of 1 to 6 carbon atoms.

For achieving the purpose of the invention, the technical scheme adopted by the present invention is:

A kind of electrochemical synthesis method of the following general formula of alkyl hydroxylamine salt,

RNHOH·Y

Wherein R is an alkyl group containing 1 to 6 carbon atoms, Y is sulfuric acid or hydrochloric acid,

The method uses the corresponding nitro-substituted alkanes as raw materials, adopts a plate-and-frame diaphragm type electrolytic cell, uses a cationic homogeneous membrane as a diaphragm, and uses an aqueous solution of sulfuric acid or hydrochloric acid with a concentration of 5 to 35% as electrolysis for the cathode or anode. liquid, the molar ratio of the nitro-substituted alkane added in the cathode chamber to the sulfuric acid or hydrochloric acid in the electrolyte is 1:1-5, and the electrolytic product containing alkyl hydroxylamine salt is synthesized through electrolytic reduction reaction, and the electrolytic product is separated and purified to obtain the described of alkylhydroxylamine salts.

Nitro-substituted alkanes containing 1 to 6 carbon atoms undergo the following reactions on the surface of the cathode:

Wherein R is an alkyl group containing 1 to 6 carbon atoms;

The anode reaction is:

or

The electrolytic reduction reaction is carried out under the following conditions: the temperature of the electrolyte is 10-90°C, the current density is 100-3000A/m ² , the electrolysis voltage is 3.0-7.0V, and the concentration of the alkyl hydroxylamine salt in the catholyte reaches 15- 25% by weight, or when the electrolysis reaches 50-100% of the electricity required for the added alkyl nitro compound based on the Faraday electricity calculation, the electrolysis is stopped.

The negative electrode of described electrolyzer is one of following:

① Copper ② Copper-Zinc Alloy ③ Lead ④ Lead-Silver Alloy ⑥ Monel ⑦ Copper Amalgam ⑧ Graphite;

The anode of the electrolyzer is one of the following:

① electrode ② titanium iridium electrode ③ glassy carbon electrode ④ lead ⑤ lead-silver alloy ⑥ graphite ⑦ titanium-based metal oxide coated electrode (DSA);

The cationic homogeneous membrane is one of the following:

① Polystyrene sulfonic acid membrane ② Perfluorosulfonic acid membrane ③ Perfluorocarboxylic acid membrane.

The reactant nitro-substituted alkane is one of the following:

①Nitromethane ②Nitroethane ③1-Nitropropane ④2-Nitropropane ⑤1-Nitrobutane ⑥Nitropentane ⑦Nitrohexane ⑧Nitrocyclohexane

Further, the synthesis method of the described alkyl hydroxylamine salt refers to the synthesis of isopropyl hydroxylamine salt, and the reactant uses 2-nitropropane.

The most suitable electrolyte temperature for the electrolytic reduction reaction is 30-60°C, the most suitable current density is 1000-2000A/m ² , and the most suitable electrolytic voltage is 3.5-5.0V.

The separation and purification of the electrolytic product generated by the electrolytic reduction reaction can be carried out according to the following steps: the electrolytic product after the reaction is distilled under reduced pressure, with a boiling point of 30-70° C., and the product after the reduced-pressure distillation is frozen and crystallized, and the crystallization temperature is -10 ° C. At ~20°C, the crystallized product is centrifuged or vacuum filtered, and then vacuum-dried to obtain a high-purity alkylhydroxylamine salt.

Specifically, the electrochemical synthesis method of described more preferred alkyl hydroxylamine salt is carried out as follows:

(1) Using the pump circulation method, add 5-35% sulfuric acid or hydrochloric acid aqueous solution into the cathode chamber and the anode chamber of the electrolytic cell, and adopt the continuous dripping or intermittent feeding method to add the nitro-substituted alkanes to the cathode chamber, and the cathode chamber is nitrated The molar ratio of substituted alkanes to sulfuric acid or hydrochloric acid is 1:1～5;

(2) Control the temperature of the cathode chamber and the anode chamber at 10-90°C, adjust the reaction working current at 100-3000A/m ² , and the reaction tank voltage at 3.0-7.0V;

(3) Control electrolysis time, stop electrolysis when making alkyl hydroxylamine salt concentration reach 15～25wt% in catholyte; electrolysis.

(4) The electrolysis product after the reaction is distilled under reduced pressure, the boiling point is 30～70°C, the product after the reduced pressure distillation is subjected to freezing and crystallization, the crystallization temperature is -10～20°C, the crystallized product is centrifugally separated or vacuum filtered, and then carried out Vacuum drying can obtain high-purity alkyl hydroxylamine salt.

In particular, when the nitro-substituted alkane is 2-nitropropane, the synthesis method of the alkyl hydroxylamine salt refers to the synthesis method of isopropyl hydroxylamine salt, which is carried out as follows:

(1) Adopt the pump circulation method, add 5-35% sulfuric acid or hydrochloric acid aqueous solution into the cathode chamber and the anode chamber of the electrolytic cell, adopt continuous dripping or intermittent feeding mode, add 2-nitropropane into the cathode chamber, the cathode chamber The molar ratio of 2-nitropropane to sulfuric acid or hydrochloric acid is 1:1～5;

(2) Control the temperature of the cathode chamber and the anode chamber at 30-60°C, adjust the reaction working current to 1000-2000A/m ² , and the reaction tank voltage to 3.0-5.0V;

(3) control electrolysis time, stop electrolysis when making isopropyl hydroxylamine salt concentration reach 15～25wt% in catholyte;

(4) The electrolytic solution after the reaction is distilled under reduced pressure, the boiling point is 30-70°C, the product after the reduced-pressure distillation is frozen and crystallized, the crystallization temperature is -10-20°C, the crystallized product is centrifugally separated or vacuum filtered, and then Vacuum drying can obtain high-purity isopropyl hydroxylamine salt.

2-Nitropropane undergoes the following reaction on the cathode surface:

or

The anode reaction is:

or

A kind of electrochemical synthesis method of the following general formula of alkylhydroxylamine,

RNHOH

Wherein R is an alkyl group containing 1 to 6 carbon atoms, and the alkyl hydroxylamine salt is prepared according to the above method, and the alkyl hydroxylamine salt is neutralized with a strong base to generate the corresponding alkyl hydroxylamine. The strong base mentioned here usually refers to strong bases such as sodium hydroxide and potassium hydroxide, which can be neutralized with alkyl hydroxylamine salts.

The beneficial effects of the electrochemical synthesis method of a kind of alkylhydroxylamine salt of the present invention are mainly reflected in: (1) the synthetic route is short, the process flow is simple, the product can be synthesized in one step, the production link is reduced, and the production cost is reduced; ( 2) The Faraday efficiency of the synthesis process can be as high as more than 90%, the reaction conditions are mild, the control is simple, and the production process is basically pollution-free; (3) the product has high purity, and the raw materials are easy to obtain and cheap. The process is used to produce isopropyl hydroxylamine hydrochloride Or sulfate, the cost is only 1/5 to 1/10 of chemical synthesis, which is a kind of green electrosynthesis method with great development prospects.

(4) Specific implementation methods

The present invention will be further described below in conjunction with specific examples, but the methods and technical parameters involved in the scheme should not be construed as limitations on the present invention.

Embodiment 1～7: the preparation of isopropyl hydroxylamine hydrochloride

In ion-exchange membrane electrolyzer, adopting pure copper sheet is negative electrode, and area is 5.0cm * 6.0cm, and large area graphite is anode, and catholyte is the technical grade hydrochloric acid solution of 300mL 18wt% and adds 30mL technical grade 2-nitropropane, The anolyte is 400mL 18wt% industrial grade hydrochloric acid solution, the cathode is separated by a polystyrene sulfonic acid membrane homogeneous ionic membrane, and the catholyte and anolyte are circulated by a magnetic pump respectively. Then direct current is passed through the electrolytic cell for electrolysis. The reaction conditions and yield are shown in Table 1. During the reaction, the temperature of the cathode chamber and the anode chamber is controlled at 10-90°C, and the cell voltage is in the range of 3.0-7.0V. Chlorine gas is absorbed with NaOH solution. After the reaction is over, take out the electrolyte, carry out vacuum distillation in a 90°C water bath to remove most of the water, then freeze and crystallize in a -5°C water bath for 12 hours, and separate the solid isopropyl hydroxylamine hydrochloride crystals , Vacuum drying, the purity is over 98%. The experimental data are shown in Table 1, more than 90% of unreacted 2-nitropropane can be recovered in the distillation process.

         Table 1 Experimental data of Examples 1-7

Embodiment 8～14: the preparation of isopropyl hydroxylamine hydrochloride

In the ion-exchange membrane electrolyzer, copper, copper-zinc alloy, lead, lead-silver alloy, Monel alloy, amalgamated copper sheet or graphite are used as the cathode respectively, with an area of 5.0cm×6.0cm, and the large-area DSA electrode is Anode, catholyte is 300mL18wt% industrial grade hydrochloric acid solution plus 30mL industrial grade 2-nitropropane, anolyte is 400mL 18wt% industrial grade hydrochloric acid solution, cathode and anode are separated by perfluorosulfonic acid ion membrane, respectively The catholyte and anolyte are circulated by a magnetic pump. Then, direct current is applied to the electrolytic cell for electrolysis. The current density is 2000A/m ² , and the reaction time is 3 hours. Chlorine gas generated during the process is absorbed with NaOH solution. After the reaction is over, take out the electrolyte, carry out vacuum distillation in a 50-90°C water bath to remove most of the water, then freeze and crystallize in a 0°C water bath for 12 hours, and separate the solid crystal of isopropylhydroxylamine hydrochloride substances with a purity of over 98%. The experimental conditions and yields are shown in Table 2, and the unreacted 2-nitropropane can be recovered in the distillation process.

             Table 2 Experimental Data of Examples 8-14

The DSA electrodes in Table 2 are titanium-based metal oxide coated electrodes

Embodiment 15～17: the preparation of isopropyl hydroxylamine hydrochloride

In the ion-exchange membrane electrolyzer, adopt ruthenium-titanium electrode, glassy carbon, graphite electrode as anode respectively, copper plate is cathode, area is 5.0cm×6.0cm, catholyte is 300mL 18wt% industrial grade hydrochloric acid solution plus 30mL industrial grade 2-nitropropane, the anolyte is 400mL 18wt% industrial grade hydrochloric acid solution, the cathode and anode are separated by perfluorocarboxylic acid type ion membrane, and the cathode solution and anolyte are respectively circulated by a magnetic pump. Then, direct current is applied to the electrolytic cell for electrolysis, the current density is 2000A/m ² , and the reaction time is 3 hours. Chlorine gas generated during the process is absorbed with NaOH solution. After the reaction is over, take out the electrolyte, carry out vacuum distillation in a 50-90°C water bath to remove most of the water, then freeze and crystallize in a 0°C water bath for 12 hours, and separate the solid crystal of isopropyl hydroxylamine hydrochloride substances with a purity of over 98%. The experimental conditions and yield are shown in Table 3, and the unreacted 2-nitropropane can be recovered in the distillation process.

Table 3 Experimental data of Examples 15-17

Embodiment 18～20: the preparation of isopropyl hydroxylamine sulfate

In ion-exchange membrane electrolyzer, adopt pure copper sheet as negative electrode, area is 5.0cm * 6.0cm, with lead, lead-silver alloy, titanium-iridium alloy electrode respectively as anode, catholyte is the industrial grade sulfuric acid solution of 150mL 15wt%. 25mL industrial grade 2-nitropropane, the anolyte is 150mL 15wt% industrial grade sulfuric acid solution, the anode and cathode are separated by a homogeneous ionic membrane, and the catholyte and anolyte are circulated by a magnetic pump respectively. Then, direct current is applied to the electrolytic cell for electrolysis, the current density is 2500A/m ² , the reaction time is 3.0 hours, the temperature of the cathode chamber and the anode chamber is controlled at 20-30°C during the reaction, and the cell voltage is in the range of 3.8-4.1V. After the reaction is over, take out the electrolyte, and carry out vacuum distillation in a 90°C water bath to remove most of the water, then freeze and crystallize in a 10°C water bath for 12 hours, and separate the solid isopropyl hydroxylamine sulfate crystals. More than 98%. See Table 4 for experimental conditions and yields.

           Table 4 Experimental data of Examples 18-20

Embodiment 21: Preparation of isopropyl hydroxylamine hydrochloride

Copper is used as the cathode, DSA and graphite are respectively used as the anode, the catholyte is 6L and 7L of 20wt% industrial hydrochloric acid, 30L of industrial hydrochloric acid with an anolyte concentration of 20wt%, and the feeding amount of 2-nitropropane is 2000g. During the electrolysis process, the temperature of the cathode area is controlled at 30-60°C, the temperature of the anode area is 30-60°C, the cathode area and the anode area are circulated by mechanical pumps (20L/min), and the electrolysis current is 2000Ah. During the electrolysis process, the average cell voltage was 4.0-5.5V, and 4 batches were electrolyzed at a current density of 2000A/m ² . On average, 200g/batch of 2-nitropropane was recovered in each batch to obtain an average of 1845g/batch of isopropylhydroxylamine hydrochloride crude product. The average current efficiency is 88.7%, the average molar reaction yield is 81.8%, the product is light yellow to white crystal, and the purity exceeds 98%. When the current density is 1000A/m ² , the average current efficiency is 89.2%, and the average molar reaction yield is 82.3%. Chlorine gas produced during the reaction process is absorbed by NaOH solution, and unreacted 2-nitropropane is recovered during the distillation process.

Embodiment 22～29: the preparation of alkyl hydroxylamine salt

In ion-exchange membrane electrolyzer, adopt red copper as negative electrode, area is 5.0cm * 6.0cm, large area DSA electrode is anode, catholyte is the technical grade hydrochloric acid solution of 300mL18wt%, adds 2-nitropropane (30mL) respectively , nitromethane (20mL), nitroethane (25mL), 1-nitropropane (30mL), 1-nitrobutane (35mL), nitropentane (40mL), nitrohexane (45mL) and nitrocyclohexane (45mL), the anolyte is 400mL 18wt% industrial grade hydrochloric acid solution, the anode and cathode are separated by a perfluorosulfonic acid ion membrane, and a magnetic pump is used to circulate the catholyte and anolyte respectively. Then, direct current is applied to the electrolytic cell for electrolysis. The current density is 2000A/m ² , and the reaction time is 3 hours. Chlorine gas generated during the process is absorbed with NaOH solution. After the reaction is over, take out the electrolyte, carry out vacuum distillation in a 50-90°C water bath to remove most of the water, then freeze and crystallize in a 0°C water bath for 12 hours, and separate the solid isopropylhydroxylamine hydrochloride, Crystallized methylhydroxylamine hydrochloride, ethylhydroxylamine hydrochloride, n-propylhydroxylamine hydrochloride, n-butylhydroxylamine hydrochloride, amylhydroxylamine hydrochloride, hexylhydroxylamine hydrochloride and cyclohexylhydroxylamine hydrochloride substances with a purity of more than 92%. The experimental data are shown in Table 5, and the unreacted raw material nitro compounds can be recovered in the distillation process. The above alkyl hydroxylamine salts can be neutralized with sodium hydroxide to obtain corresponding hydroxylamines respectively.

Table 5 Experimental data of Examples 22 to 29 Reaction substrate product current efficiency yield Example 22 2-nitropropane 30mL Isopropyl Hydroxylamine Hydrochloride 93.6% 91.2% Example 23 Nitromethane 20mL Methylhydroxylamine hydrochloride 96.76% 95.2% Example 24 Nitroethane 25mL Ethylhydroxylamine hydrochloride 91.5% 87.1% Example 25 1-nitropropane 30mL N-Propyl Hydroxylamine Hydrochloride 90.5% 88.3% Example 26 1-nitrobutane 35mL n-Butylhydroxylamine hydrochloride 88.8% 87.4% Example 27 Nitropentane 40mL Amyl Hydroxylamine Hydrochloride 89.4% 85.2% Example 28 Nitrohexane 45mL Hexyl Hydroxylamine Hydrochloride 90.5% 86.1% Example 29 Nitrocyclohexane 45mL Cyclohexyl Hydroxylamine Hydrochloride 88.6% 83.5%

Claims (10)

1. An electrochemical synthesis method of alkyl hydroxylamine salt with the following general formula,

RNHOH·Y

wherein R is alkyl containing 1-6 carbon atoms, Y is sulfuric acid or hydrochloric acid, and the method is characterized in that: the method comprises the steps of taking corresponding nitro-substituted alkane as a raw material, adopting a plate-frame diaphragm type electrolytic cell, taking a cation homogeneous membrane as a diaphragm, taking a sulfuric acid or hydrochloric acid aqueous solution with the concentration of 5-35% as an electrolyte at a cathode or an anode, synthesizing an electrolytic product containing alkyl hydroxylamine salt through an electrolytic reduction reaction by taking nitro-substituted alkane added in a cathode chamber and the electrolyte sulfuric acid or hydrochloric acid in a molar ratio of 1: 1-5, and separating and purifying the electrolytic product to obtain the alkyl hydroxylamine salt.

2. The electrochemical synthesis method of alkylhydroxylamine salts according to claim 1, wherein the electrolytic reduction reaction is carried out under the following conditions: the electrolyte temperature is 10-90 ℃, and the current density is 100-3000A/m²The electrolyticvoltage is 3.0-7.0V, when the concentration of the alkyl hydroxylamine salt in the catholyte reaches 15-25 wt%, or the required electric quantity is calculated according to the faradaic electric quantity by electrolyzing the added alkyl nitro compoundAnd when the concentration is 50-100%, stopping electrolysis.

3. The electrochemical synthesis method of an alkylhydroxylamine salt according to claim 2, wherein: the cathode of the electrolytic cell is one of the following:

① copper ② copper-zinc alloy ③ lead ④ lead-silver alloy ⑥ monel ⑦ copper amalgam ⑧ graphite;

the anode of the electrolytic cell is one of the following:

① ruthenium titanium electrode ② titanium iridium electrode ③ glassy carbon electrode ④ lead ⑤ lead-silver alloy ⑥ graphite ⑦ titanium-based metal oxide coated electrode (DSA);

the cation homogeneous membrane is one of the following:

① polystyrene sulfonic acid membrane ② perfluorosulfonic acid membrane ③ perfluorocarboxylic acid membrane.

4. The electrochemical synthesis method of an alkylhydroxylamine salt according to claim 3, wherein the reactant nitro-substituted alkane is one of the following:

① Nitromethane ② Nitroethane ③ 1-Nitropropane ④ 2-Nitropropane

⑤ 1-Nitrobutane ⑥ Nitropentane ⑦ Nitro-Hexane ⑧ Nitro-cyclohexane

5. The electrochemical synthesis method of an alkylhydroxylamine salt according to claim 4, wherein the nitro-substituted alkane is 2-nitropropane.

6. The electrochemical synthesis method of alkyl hydroxylamine salts according to claim 2, wherein the temperature of the electrolyte is 30-60 ℃, and the current density is 1000-2000A/m²The electrolytic voltage is 3.5-5.0V.

7. The electrochemical synthesis method of alkylhydroxylamine salts according to claim 2, wherein the separation and purification are carried out by the following steps:

and (3) distilling the reacted electrolysis product under reduced pressure, wherein the boiling point is 30-70 ℃, freezing and crystallizing the product after the reduced pressure distillation, the crystallization temperature is-10-20 ℃, and performing centrifugal separation or vacuum filtration on the crystallized product, and then performing vacuum drying to obtain the high-purity alkyl hydroxylamine salt.

8. The electrochemical synthesis process of an alkylhydroxylamine salt according to claim 3, wherein said process comprises the steps of:

(1) adding 5-35% of sulfuric acid or hydrochloric acid aqueous solution into a cathode chamber and an anode chamber of an electrolytic cell in a pump circulation mode, and adding nitro-substituted alkane into the cathode chamber in a continuous dropwise or intermittent feeding mode, wherein the molar ratio of the nitro-substituted alkane in the cathode chamber to the sulfuric acid or hydrochloric acid is 1: 1-5;

(2) controlling the temperature of the cathode chamber and the anode chamber to be 10-90 ℃, and adjusting the reaction working current to be 100-3000A/m²The voltage of the reaction tank is 3.0-7.0V;

(3) controlling the electrolysis time to stop the electrolysis when the concentration of the alkyl hydroxylamine salt in the catholyte reaches 15-25 wt%; or the electrolysis is stopped until 50-100% of the required electric quantity of the added alkyl nitro compound is calculated according to the faradaic electric quantity.

(4) And (3) distilling the reacted electrolysis product under reduced pressure, wherein the boiling point is 30-70 ℃, freezing and crystallizing the product after the reduced pressure distillation, the crystallization temperature is-10-20 ℃, and performing centrifugal separation or vacuum filtration on the crystallized product, and then performing vacuum drying to obtain the high-purity alkyl hydroxylamine salt.

9. The electrochemical synthesis process of an alkylhydroxylamine salt according to claim 8, wherein said process comprises the steps of:

(1) adding 5-35% of sulfuric acid or hydrochloric acid aqueous solution into a cathode chamber and an anode chamber of an electrolytic cell in a pump circulation mode, adding 2-nitropropane into the cathode chamber in a continuous dropwise adding or intermittent feeding mode, wherein the molar ratio of the 2-nitropropane to the sulfuric acid or hydrochloric acid in the cathode chamber is 1: 1-5;

(2) controlling the temperature of the cathode chamber and the anode chamber to be 30-60 ℃, and adjustingThe reaction operating current is 1000-2000A/m²The voltage of the reaction tank is 3.0-5.0V;

(3) controlling the electrolysis time to stop the electrolysis when the concentration of the isopropyl hydroxylamine salt in the catholyte reaches 15-25 wt%;

(4) and (3) distilling the reacted electrolyte under reduced pressure, wherein the boiling point is 30-70 ℃, freezing and crystallizing the product after the reduced pressure distillation, the crystallization temperature is-10-20 ℃, and performing centrifugal separation or vacuum filtration on the crystallized product, and then performing vacuum drying to obtain the high-purity isopropyl hydroxylamine salt.

10. An electrochemical synthesis method of alkyl hydroxylamine with the following general formula,

RNHOH

wherein R is alkyl containing 1-6 carbon atoms, and is characterized in that: the alkylhydroxylamine salt prepared by the method according to claim 1 to 9, wherein the alkylhydroxylamine salt is neutralized with a strong base to produce the corresponding alkylhydroxylamine.