CN115772106A - Diamine bisdithiocarbamic acid sodium salt and preparation method thereof - Google Patents

Diamine bisdithiocarbamic acid sodium salt and preparation method thereof Download PDF

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CN115772106A
CN115772106A CN202211378155.XA CN202211378155A CN115772106A CN 115772106 A CN115772106 A CN 115772106A CN 202211378155 A CN202211378155 A CN 202211378155A CN 115772106 A CN115772106 A CN 115772106A
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hydrazine
sodium salt
carbon disulfide
temperature
reaction
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王永斌
张鑫
刘守信
周涛
王怡霖
王军
梁友乾
王源瑞
王亚平
牛永胜
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Northwest Research Institute of Mining and Metallurgy
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Abstract

The invention relates to a diamine bis-dithiocarbamate sodium salt, which is prepared by taking hydrazine hydrate, carbon disulfide and sodium hydroxide as raw materials; the main component of the compound is hydrazine bis-dithiocarbamate with molecular formula C 2 H 2 N 2 Na 2 S 4 The molecular weight is 228.30, and the molecular structural formula is as follows:

Description

Diamine bisdithiocarbamic acid sodium salt and preparation method thereof
Technical Field
The invention relates to a preparation method of an organic chemical and an aqueous solution thereof, in particular to a hydrazine bisdithiocarbamate sodium salt and a preparation method thereof.
Background
The dithiocarbamates are important organic compounds, and are mostly prepared by reacting organic amine with carbon disulfide at low temperature to generate alkyl dithiocarbamates and then neutralizing with alkali.
The dithiocarbamates can be used as an overspeed rubber vulcanization accelerator, a lubricating oil additive, a purifying agent for oil extraction sewage in oil fields, a wastewater treating agent containing metal ions, an agricultural bactericide, an antidote for heavy metal poisoning in medicine, an antioxidant for gasoline products, a flotation agent for metal sulfide minerals and the like, and can be widely applied to the fields of rubber, petroleum, agriculture, mining industry, medicine, environmental protection, analytical chemistry and the like. Therefore, the research and the development of the novel dithiocarbamates compounds are of great significance.
Disclosure of Invention
The invention aims to provide a high-purity hydrazine bis-dithiocarbamate sodium salt.
The invention also provides a preparation method of the diamine bisdithiocarbamate sodium salt.
In order to solve the above problems, the present invention provides a diamine bisdithiocarbamate sodium salt, which is characterized in that: the hydrazine bis-dithiocarbamate sodium salt is prepared by taking hydrazine hydrate, carbon disulfide and sodium hydroxide as raw materials; the main component of the compound is hydrazine bis-dithiocarbamate with molecular formula C 2 H 2 N 2 Na 2 S 4 The molecular weight is 228.30, and the molecular structural formula is as follows:
Figure 970379DEST_PATH_IMAGE001
the form of the hydrazine bisdithiocarbamate sodium salt is aqueous solution or solid.
The molar ratio of hydrazine hydrate to carbon disulfide to sodium hydroxide is 1: (2 to 8): 2.
the preparation method of the hydrazine bisdithiocarbamate sodium salt aqueous solution comprises the following steps:
firstly, adding excessive carbon disulfide with the mass percent concentration of more than 96% into reaction equipment at one time, keeping the temperature for 10 to 30 ℃, then slowly dropwise adding hydrazine hydrate with the mass percent concentration of 40 to 80 percent by weight while stirring, and reacting for 2 to 3 hours at 10 to 30 ℃ to obtain hydrazine dithiocarbamic acid;
adding a sodium hydroxide aqueous solution with the mass percentage concentration of 20 to 30 percent into the hydrazine dithiocarbamic acid, and carrying out neutralization reaction for 2h at the temperature of 20 to 40 ℃ to obtain a mixed solution containing the hydrazine dithiocarbamic acid sodium;
thirdly, placing the mixed solution containing the hydrazine sodium dithio-carbamate into a container, standing for layering, recovering the excessive carbon disulfide at the lower layer, wherein the upper layer solution is the aqueous solution of the hydrazine sodium dithio-carbamate with the mass percentage concentration of 40-47%.
The preparation method of the solid of the diamine bisdithiocarbamate sodium salt comprises the following steps:
(1) adding carbon disulfide raw material with mass percent concentration of more than 96% into a reaction vessel according to 3-5 times of theoretical dosage; adding granular or flaky sodium hydroxide solid with one time of theoretical dosage under stirring;
(2) gradually dripping hydrazine hydrate with the mass percent concentration of 80 percent by weight into a reaction container under the condition of keeping the temperature of reactants at 10-30 ℃, wherein the dripping time is controlled to be 2-3 h, and the dripping temperature is controlled to be 15-40 ℃; after the hydrazine hydrate is dripped, continuously keeping the reaction temperature at 30-40 ℃ for reacting for 1h to obtain a reaction product;
(3) and (3) carrying out reduced pressure evaporation on the reaction product at a vacuum pressure of-0.06 to-0.08 MPa and a temperature of 45 to 50 ℃ to recover carbon disulfide to obtain a solid product, wherein the solid product is the crystals of the hydrazine dithiocarbamic acid sodium salt.
Compared with the prior art, the invention has the following advantages:
1. the invention mixes carbon disulfide and hydrazine hydrate for reaction to generate hydrazine bis-dithiocarbamate, and then reacts with sodium hydroxide to obtain the hydrazine bis-dithiocarbamate sodium salt. By controlling the feeding temperature and the feeding sequence, the reaction is easier to control and more sufficient, and the product quality and the yield are improved.
2. According to the invention, a sodium hydroxide solution with the concentration of 20-30% is added to produce a sodium hydrazine dithio carbamate solution with the concentration of 40-47% by mass, and the solution is easy to layer due to the fact that carbon disulfide and reaction liquid are immiscible and the specific gravity difference is large, so that the recovery of excessive carbon disulfide can be realized by liquid separation after standing for 2 hours, and the raw material cost is saved.
3. According to the method, carbon disulfide is used as an autololvent, sodium hydroxide solid is added to produce a sodium hydrazine dithio carbamate crystal product, excessive carbon disulfide is recovered through vacuum reduced pressure distillation, the operability is high, the environmental pollution can be reduced, and the sustainability of the use is high.
4. The invention has the advantages of simple process, convenient operation, high purity of finished products and the like, and can be widely applied to the fields of rubber, petroleum, agriculture, mining industry, medicine, environmental protection, analytical chemistry and the like.
Detailed Description
The sodium salt of the hydrazine bis-dithiocarbamate is prepared by taking hydrazine hydrate, carbon disulfide and sodium hydroxide as raw materials; the main component is hydrazine bis-dithiocarbamate (also known as disodium 1, 2-dicarbamoyl disulfate or disodium hydrazine bis (dithiocarbamate), etc.), and the molecular formula is C 2 H 2 N 2 Na 2 S 4 The molecular weight is 228.30, and the molecular structural formula is as follows:
Figure 722434DEST_PATH_IMAGE001
the form of the hydrazine bisdithiocarbamate sodium salt is aqueous solution or solid.
Wherein: the molar ratio of hydrazine hydrate, carbon disulfide and sodium hydroxide is 1: (2 to 8): 2.
a method for preparing a hydrazine bis-dithiocarbamate sodium salt aqueous solution comprises the following steps:
firstly, adding carbon disulfide with the mass percent concentration of more than 96% into reaction equipment at one time, keeping the temperature for 10-30 ℃, then slowly dropwise adding hydrazine hydrate with the mass percent concentration of 40-80% by weight under stirring, and reacting for 2-3 h at 10-30 ℃ to obtain the hydrazine dithiocarbamic acid.
Since the reaction is exothermic, the cooling force needs to be increased to control the dropping speed in the reaction process so as to ensure that the reaction temperature does not exceed 40 ℃.
Figure 731848DEST_PATH_IMAGE002
Adding a sodium hydroxide aqueous solution with the mass percentage concentration of 20 to 30 percent into the hydrazine dithiocarbamic acid, and carrying out neutralization reaction for 2h at the temperature of 20 to 40 ℃ to obtain a mixed solution containing the hydrazine dithiocarbamic acid sodium.
Figure 467722DEST_PATH_IMAGE003
Thirdly, placing the mixed solution containing the hydrazine sodium dithio-carbamate into a container, standing for layering, recovering the excessive carbon disulfide at the lower layer, and obtaining the upper layer solution which is the aqueous solution of the hydrazine sodium dithio-carbamate with the mass percentage concentration of 40-47%.
A preparation method of a hydrazine bisdithiocarbamate sodium salt solid comprises the following steps:
(1) adding carbon disulfide raw material with mass percent concentration of more than 96% into a reaction vessel according to 3-5 times of theoretical dosage; granular or flake sodium hydroxide solids in an amount twice the theoretical amount were added with stirring.
(2) Gradually dripping 80 wt% of hydrazine hydrate into a reaction vessel under the condition of keeping the temperature of the reactants at 10-30 ℃, wherein the dripping time is controlled to be 2-3 h, and the dripping temperature is controlled to be 15-40 ℃; after the hydrazine hydrate is dripped, the reaction temperature is kept at 30 to 40 ℃ for 1 hour to obtain a reaction product.
(3) Transferring the reaction product to a vacuum evaporation recovery device system, and carrying out reduced pressure evaporation and recovery on carbon disulfide at the vacuum pressure of-0.06 to-0.08 MPa and the temperature of 45 to 50 ℃ to obtain a solid product, wherein the solid product is the hydrazine dithiocarbamic acid sodium salt crystal.
Example 1 a method for preparing an aqueous solution of a sodium salt of hydrazine bisdithiocarbamate comprises the steps of:
158g (equivalent to 2 moles) of carbon disulfide with the mass percentage concentration of more than 96% is added into a reaction device at one time, the temperature is kept for 10 to 30 ℃, then 125g (equivalent to 1 mole) of hydrazine hydrate solution with the weight of 40% is slowly dropped into the reaction device under stirring, the feeding time is controlled within 2 hours, after the feeding is finished, the stirring reaction is carried out for 0.5 to 1h at the temperature of 10 to 30 ℃, so that the materials are fully reacted, and 283g of hydrazine dithiocarbamic acid mixed solution with the main component content of 65% by weight is obtained.
Secondly, without replacing reaction equipment, 267g (equivalent to 2 moles) of 30 percent by weight of sodium hydroxide aqueous solution is continuously added into the mixed solution of the hydrazine dithiocarbamic acid, and the mixed solution is neutralized and reacted for 2h at 10 to 30 ℃ to obtain 550g of the product of the sodium hydrazine dithiocarbamic acid solution with the main component content of 41 percent by weight (note: the product has trace carbon disulfide content and does not need to be stood for layering), and the total recovery rate is 97 percent.
Example 2 a method for preparing an aqueous solution of a sodium salt of hydrazine bisdithiocarbamate comprises the steps of:
firstly, 237.5g (equivalent to 3 moles) of carbon disulfide with the mass percentage concentration of more than 96% is added into a reaction device at one time, the temperature is kept for 20 to 30 ℃, then 72.5g (equivalent to 1 mole) of hydrazine hydrate solution with the weight of 69% is slowly dripped under stirring, the feeding time is controlled within 2 hours, after the materials are added, the materials are stirred and reacted for 0.5 to 1h at the temperature of 20 to 40 ℃, and the materials are fully reacted to obtain 310g of hydrazine dithiocarbamic acid mixed solution with the main component content of 59.3 wt.
267g (equivalent to 2 moles) of aqueous sodium hydroxide solution (30% by weight) was continuously added to the mixed solution of the hydrazine dithiocarbamic acid without changing reaction equipment, and the mixed solution of the hydrazine dithiocarbamic acid was subjected to neutralization reaction at 20 to 30 ℃ for 2 hours to obtain 577g of a mixed solution of the hydrazine dithiocarbamic acid sodium.
Thirdly, placing the mixed solution containing the hydrazine bis-dithiocarbamate into a cone middle tank, standing for 2 hours to stratify the solution, recovering 79g of excessive carbon disulfide separated out from the lower layer through liquid separation operation, and obtaining 498g of the hydrazine bis-dithiocarbamate aqueous solution as the upper layer solution. The analysis showed that the content of sodium hydrazine bisdithiocarbamate in the solution was 45.8% by weight, and the recovery rate was 96%.
Example 3 a method for preparing an aqueous solution of a sodium salt of hydrazine bisdithiocarbamate, comprising the steps of:
316.7g (equivalent to 4 moles) of carbon disulfide with the mass percentage concentration of more than 96 percent is added into a reaction device at one time, the temperature is kept for 20 to 40 ℃, then 72.5g (equivalent to 1 mole) of hydrazine hydrate solution with the weight of 80 percent is slowly dripped under stirring, the feeding time is controlled within 2 hours, after the materials are added, the materials are stirred and reacted for 0.5 to 1h at the temperature of 20 to 40 ℃, and the materials are fully reacted, so that 389.2g of hydrazine dithiocarbamic acid mixed solution with the main component content of 47.2 percent by weight is obtained.
Next, without changing the reaction equipment, 267g (equivalent to 2 moles) of a 30% by weight aqueous sodium hydroxide solution was continuously added to the above mixed solution of the hydrazine dithiocarbamic acid, and the mixture was neutralized at 20 to 30 ℃ for 2 hours to obtain 656.2g of a mixed solution containing sodium hydrazine dithiocarbamic acid.
Placing the mixed solution containing the hydrazine dithiocarbamic acid sodium salt into a cone middle tank, standing for 2 hours to enable the solution to be layered, recovering 158g of the excessive carbon disulfide at the lower layer through liquid separation operation, and obtaining 487g of the hydrazine dithiocarbamic acid sodium salt aqueous solution at the upper layer. The solution was analyzed to contain 46.8% by weight of sodium hydrazine bisdithiocarbamate, and the recovery rate was 97%.
Example 4 a method for preparing a solid of the sodium salt of bisaminodithiocarbamic acid, comprising the steps of:
(1) in the reaction vessel, 475g (equivalent to 6 moles) of carbon disulphide was initially charged and 80g (equivalent to 2 moles) of the particulate sodium hydroxide solid was added with stirring at 150 rpm.
(2) Gradually dripping 62.5g (equivalent to 1 mol) of hydrazine hydrate accounting for 80 wt% into a reaction vessel under the condition of keeping the temperature of the reactants at 15-40 ℃, wherein the dripping time is controlled to be 2-3 h, and the dripping temperature is controlled to be 15-40 ℃; after the hydrazine hydrate is dripped, the reaction temperature is continuously kept at 30 to 40 ℃ for reaction for 1 hour to obtain 537g of slurry reaction product.
(3) Transferring the reaction product to a vacuum evaporation recovery device system, and carrying out reduced pressure evaporation to recover 316g of carbon disulfide under the conditions that the vacuum pressure is-0.06 to 0.08MPa and the temperature is 45 to 50 ℃ to obtain 282g of a solid product, namely hydrazine bisdithiocarbamic acid sodium salt. The solid was analyzed to have a content of sodium hydrazine bisdithiocarbamate of 80.8% by weight, and a recovery rate of 98%.
Example 5 a method for preparing a solid of the sodium salt of bisaminodithiocarbamic acid, comprising the steps of:
(1) in the reaction vessel, 633g of carbon disulfide (corresponding to 8 moles) was added, and 80g of granular sodium hydroxide solid (corresponding to 2 moles) was added at a stirring rate of 150 rpm.
(2) Gradually dripping 62.5g (equivalent to 1 mol) of hydrazine hydrate accounting for 80 wt% into a reaction vessel under the condition of keeping the temperature of the reactants at 15-40 ℃, wherein the dripping time is controlled to be 2-3 h, and the dripping temperature is controlled to be 15-40 ℃; after the hydrazine hydrate is dripped, the reaction temperature is kept at 30 to 40 ℃ for 1 hour to obtain 775.5g of reaction product.
(3) Transferring the reaction product to a vacuum evaporation recovery device system, and carrying out reduced pressure evaporation to recover 475g of carbon disulfide under the conditions that the vacuum pressure is-0.06 to 0.08MPa and the temperature is 45 to 50 ℃ to obtain 282g of a solid product, namely the hydrazine dithiocarbamic acid sodium formate crystal. The analysis shows that the content of the sodium hydrazine dithio carbamate in the crystal is 80 percent by weight, and the recovery rate is 97 percent.
Example 6 a method for preparing a solid of the sodium salt of hydrazinedithiocarbamic acid, comprising the steps of:
(1) in the reaction vessel, 554g of carbon disulphide (corresponding to 7 moles) was initially charged and 80g of particulate sodium hydroxide solid (corresponding to 2 moles) was added with stirring at 150 rpm.
(2) Gradually dripping 62.5g (equivalent to 1 mol) of hydrazine hydrate into a reaction vessel by weight under the condition of keeping the temperature of the reaction product between 15 and 40 ℃, wherein the dripping time is controlled to be between 2 and 3 hours, and the dripping temperature is controlled to be between 15 and 40 ℃; after the hydrazine hydrate is dripped, the reaction temperature is kept at 30 to 40 ℃ for 1 hour to obtain 696g of reaction product.
(3) Transferring the reaction product to a vacuum evaporation recovery device system, and carrying out reduced pressure evaporation to recover 400g of carbon disulfide under the conditions that the vacuum pressure is-0.06 to 0.08MPa and the temperature is 45 to 50 ℃ to obtain 282g of a solid product, namely the hydrazine dithiocarbamic acid sodium formate crystal. The crystals were analyzed to have a hydrazine bisdithiocarbamate content of 79.5% by weight, with a recovery of 98%.

Claims (5)

1. A sodium salt of a hydrazine bisdithiocarbamate, characterized by: the hydrazine bis-dithiocarbamate sodium salt is prepared by taking hydrazine hydrate, carbon disulfide and sodium hydroxide as raw materials; the main component of the compound is hydrazine bisdithiocarbamic acid sodium salt with the molecular formula of C 2 H 2 N 2 Na 2 S 4 The molecular weight is 228.30, and the molecular structural formula is as follows:
Figure DEST_PATH_IMAGE001
2. the sodium salt of a hydrazine bisdithiocarbamate according to claim 1, wherein: the form of the diamine bisdithiocarbamic acid sodium salt is aqueous solution or solid.
3. The method for producing an aqueous solution of a sodium salt of a hydrazine bisdithiocarbamate according to claim 1, wherein: the molar ratio of hydrazine hydrate, carbon disulfide and sodium hydroxide is 1: (2 to 8): 2.
4. the method for preparing an aqueous solution of a sodium salt of hydrazine bisdithiocarbamate according to claim 2, comprising the steps of:
firstly, adding excessive carbon disulfide with the mass percent concentration of more than 96% into reaction equipment at one time, keeping the temperature for 10 to 30 ℃, then slowly dropwise adding hydrazine hydrate with the mass percent concentration of 40 to 80 percent by weight while stirring, and reacting for 2 to 3 hours at 10 to 30 ℃ to obtain hydrazine dithiocarbamic acid;
adding a sodium hydroxide aqueous solution with the mass percentage concentration of 20 to 30 percent into the hydrazine dithiocarbamic acid, and carrying out neutralization reaction for 2h at the temperature of 20 to 40 ℃ to obtain a mixed solution containing the hydrazine dithiocarbamic acid sodium;
thirdly, placing the mixed solution containing the hydrazine sodium dithio-carbamate into a container, standing for layering, recovering the excessive carbon disulfide at the lower layer, wherein the upper layer solution is the aqueous solution of the hydrazine sodium dithio-carbamate with the mass percentage concentration of 40-47%.
5. The method for preparing a solid of a sodium salt of hydrazine bisdithiocarbamate according to claim 2, comprising the steps of:
(1) adding carbon disulfide raw materials with mass percent concentration of more than 96% into a reaction vessel according to 3-5 times of theoretical dosage; adding granular or flaky sodium hydroxide solid with one time of theoretical dosage under stirring;
(2) gradually dripping hydrazine hydrate with the mass percent concentration of 80 percent by weight into a reaction container under the condition of keeping the temperature of reactants at 10-30 ℃, wherein the dripping time is controlled to be 2-3 h, and the dripping temperature is controlled to be 15-40 ℃; after the hydrazine hydrate is dripped, continuously keeping the reaction temperature at 30 to 40 ℃ for reacting for 1h to obtain a reaction product;
(3) and (3) carrying out reduced pressure evaporation on the reaction product at a vacuum pressure of-0.06 to-0.08 MPa and a temperature of 45 to 50 ℃ to recover carbon disulfide to obtain a solid product, wherein the solid product is the crystals of the hydrazine dithiocarbamic acid sodium salt.
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102070235A (en) * 2010-11-11 2011-05-25 华南理工大学 Water-soluble organic thiamine heavy metal chelating agent and preparation method thereof
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CN110483353A (en) * 2019-09-06 2019-11-22 李延升 Hexa-methylene tetrathio carbamic acid or its salt and preparation method thereof, the solution containing hexa-methylene tetrathio carbamic acid or its salt

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102070235A (en) * 2010-11-11 2011-05-25 华南理工大学 Water-soluble organic thiamine heavy metal chelating agent and preparation method thereof
CN102942512A (en) * 2012-11-21 2013-02-27 南京师范大学 Preparation method of sulfide heavy metal trapping agent C2H4N2S4
CN110483353A (en) * 2019-09-06 2019-11-22 李延升 Hexa-methylene tetrathio carbamic acid or its salt and preparation method thereof, the solution containing hexa-methylene tetrathio carbamic acid or its salt

Non-Patent Citations (3)

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Title
MATTES, RAINER 等: "Salts of l, 2-Hydrazine-bis(dithiocarboxylates), Preparation, Crystal Structure, Vibrational Spectra", ZEITSCHRIFT FUER NATURFORSCHUNG, TEIL B: ANORGANISCHE CHEMIE, ORGANISCHE CHEMIE, pages 4 *
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