CN111039828A - Production method of organic guanidine bactericide - Google Patents
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- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/04—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from amines with formation of carbamate groups
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- C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
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- C07C277/00—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C277/02—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups of guanidine from cyanamide, calcium cyanamide or dicyandiamides
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Abstract
The invention provides a production method of an organic guanidine bactericide, belonging to the technical field of bactericide production. The organic guanidine bactericide is prepared by using cyanamide, ethyl chloroformate, dimethyl sulfate and dimethylamine as main raw materials through the steps of blending, substitution, one-step synthesis, dissolution, two-step synthesis and blending. According to the invention, the catalyst is added for blending before the substitution reaction, and the substitution reaction is carried out after the blending, so that the substitution reaction can be rapidly carried out due to the existence of the catalyst even if a water phase and an organic phase exist in the system at the same time, and the industrial production efficiency is ensured.
Description
Technical Field
The invention relates to the technical field of bactericide production, in particular to a production method of an organic guanidine bactericide.
Background
Guanidine exists in natural products such as protein, nucleic acid and streptomycin, and various plants such as beet, rice husk, mushroom and bean, and contains a trace amount of guanidine in human and animal bodies, but free guanidine is very unstable and easily absorbs carbon dioxide in the air to generate guanidine carbonate, so guanidine usually exists stably in the form of guanidine salt. Guanidine salts are an important component of guanidine compounds and can be derived into a wide variety of guanidine derivatives, which have good antibacterial properties. Guanidine antibacterial agents refer to antibacterial compounds containing guanidine groups in the structure, and are mainly used in the fields of medicines and pesticides.
The organic guanidine compound is also widely used as a bactericide, has various effects on fungi, and usually achieves the aim of inhibiting or killing organisms by influencing abnormal phenomena such as growth and division of the fungi, spore germination, respiratory depression, cell expansion, disruption of cytoplast, cell wall damage and the like. The guanidyl compound has high activity and is positively charged after being dissolved in water, so that the guanidyl compound is easily adsorbed on the surface of negatively charged microorganisms, the action of lysozyme of cells is blocked, and the structure of the cell surface layer is denatured and damaged, thereby inhibiting the propagation of bacteria.
Compared with the toxic and side effects (which can cause skin diseases, are harmful to human bodies and even cause cancers) of aldehyde, phenol, alcohol, peroxide and ether antibacterial agents, the defects of poor heat resistance, easiness in decomposition, odor and short service life, the guanidine antibacterial agent is not toxic (does not have carcinogenicity, denaturation and teratogenicity to human bodies), is tasteless, nonirritating, high-temperature resistant and antibacterial to the human bodies, and has good washing fastness and lasting antibacterial effect after being treated on textiles. The guanidine group in guanidino compounds is an effective active group that can interact with groups or elements in the organism, disrupting its normal substance and energy metabolism. Therefore, the guanidino compound with biological activity is commonly used as an antimicrobial agent in agricultural bactericides, disinfectants and industrial biocides, etc. The long-chain alkyl mono-guanidine and poly-guanidine, aryl guanidine, phthalylguanidine and the like have killing or inhibiting effects on a plurality of microorganisms (including bacteria, fungi, viruses and the like) and have certain biological activity.
The organic guanidine compounds are mainly synthesized by the action of amine (ammonia) and guanylated reagents such as cyanamide, isothiourea, isourea, hydrazine, isothiocyanate and the like, and in addition, the guanylated compounds can also be prepared by the condensation polymerization of guanidyl and amine. Butanamine (fine chemical raw material and intermediate, 2008, 9 th: 36-39) discloses a synthetic process of methyl N-methyl-N (N ', N' -dimethylamido) carbamate, which is synthesized as a synthetic cyclic keton preparation intermediate by the following steps: reacting lime nitrogen with water to prepare cyanamide, and reacting the cyanamide with methyl chloroformate to prepare methyl cyanamide formate; adjusting methyl cyanocarbamate to be neutral by using alkali, adding excessive 10% dimethyl sulfate, and controlling the reaction temperature to be 25 ℃ for esterification reaction to obtain a toluene solution of N-methyl cyanocarbamate; and finally, adding the toluene solution of the methyl N-methyl cyanocarbamate into the sulfate solution of dimethylamine under stirring, heating for azeotropic distillation, removing the toluene in vacuum, reacting at 90 ℃ for 5 hours, and cooling to obtain the methyl N-methyl-N-N (N ', N' -dimethyl amidino) carbamate.
The preparation process is simple in flow and uncomplicated in experimental conditions, but in practice, in the reaction process for preparing the cyanamide methyl formate, because a water phase and an organic phase exist in a system at the same time, the preparation reaction is slow, and the industrial production of the cyanamide methyl formate is influenced.
Disclosure of Invention
The invention aims to provide a method for producing an organic guanidine bactericide on the basis of the prior art, wherein a catalyst is added for blending before a substitution reaction, and the substitution reaction is carried out after the blending, so that the substitution reaction can be rapidly carried out due to the existence of the catalyst even if a water phase and an organic phase exist in a system at the same time, and the industrial production efficiency is ensured.
The production method of the organic guanidine bactericide provided by the invention comprises the following steps:
(1) blending: adding water, a catalyst and cyanamide into a liquid caustic soda blending kettle, and starting a kettle lower pump to circulate the materials;
(2) and (3) substitution: pumping the liquid caustic soda into an elevated tank, and pumping ethyl chloroformate into the elevated tank by using a vacuum pump; starting the chilled water of the liquid caustic soda blending kettle to keep the temperature of materials in the kettle below 15 ℃, dropwise adding the liquid caustic soda and ethyl chloroformate to react, keeping the reaction temperature at 15-25 ℃, stopping dropwise adding when the pH of the system is 6-7, and continuously stirring at 15-25 ℃ for 1-2 hours; transferring the material to a hydrolysate blending kettle, and starting a pump to circulate the material;
(3) one-step synthesis: pumping liquid caustic soda into a head tank, and pumping dimethyl sulfate into the head tank from a tank area; heating the materials in the hydrolysate blending kettle to 35-40 ℃, dropwise adding liquid caustic soda and dimethyl sulfate to react, controlling the pH = 7.0-7.2, and controlling the temperature at 35-40 ℃ after dropwise adding to react for 2-3 h; standing and layering after the reaction is finished, transferring the lower layer to a 15% hydrolysis kettle by a pump, and obtaining a one-step finished product of N-methyl cyanoethyl carbamate at the upper layer; extracting the lower layer liquid with organic solvent, merging the desolventizing product into one-step finished product after the organic solvent is extracted, pumping the raffinate into a liquid caustic soda dehydration kettle, raising the temperature with steam, cooling the residual organic solvent to a liquid caustic soda dehydration recovery tank through a condenser, and sending the raffinate to sewage treatment;
(4) dissolving: adding dimethylamine into a 50% dissolving kettle, and adding hydrochloric acid into an elevated tank; starting a 50% dissolving kettle for freezing, starting a kettle lower pump to circulate the materials at the temperature of below 15 ℃, dropwise adding hydrochloric acid, and dissolving to obtain dimethylamine hydrochloride;
(5) two-step synthesis: injecting hydrochloride of dimethylamine into a head tank, and pumping N-methyl cyanoethyl carbamate into a 15% dissolving kettle; starting 15% of dissolving kettle steam, heating to 75-85 ℃, starting a kettle lower pump, dropwise adding dimethylamine hydrochloride, and transferring the materials to a wastewater neutralization kettle through a pump after the reaction is finished; pumping the liquid caustic soda into a head tank; starting a wastewater neutralization kettle for refrigeration, starting a kettle lower pump to enable materials to be internally circulated, dropwise adding liquid caustic soda until the pH of the system is 7-8, pumping an organic solvent after the reaction is finished, standing for layering, transferring a lower layer to a scraper evaporator through a pump and a preheater, and transferring an upper layer to an acidified wastewater for transferring to a tank; preheating materials in a scraper evaporator by a preheater, cooling an organic solvent to a scraper water recovery tank by a condenser, cooling a second-step finished product N-ethoxy-carbonyl-N, N ', N' -trimethylguanidine by the condenser, transferring the cooled second-step finished product to a storage tank, and pumping a semi-finished product into the top of the scraper evaporator again by a wastewater circulating transfer tank for circulation;
(6) blending: pumping the second-step finished product into a finished product preparation kettle, pumping a blending solvent for blending to obtain a finished product, namely the organic guanidine bactericide, wherein the structural formula of the organic guanidine bactericide is as follows:
the production method of the organic guanidine bactericide further comprises the following steps: (7) recovering dimethylamine: pumping the liquid caustic soda into a high-level tank, transferring materials in a rotary tank in the acidified wastewater into a 50% hydrolysis kettle through a pump, dropwise adding the liquid caustic soda, adjusting the pH value to 7.0-7.2, starting steam, and cooling dimethylamine to a 50% hydrolysis recovery water tank through a condenser.
In the production method of the organic guanidine bactericide, in the step (1), the catalyst is benzyltriethylammonium chloride, and the adding amount of the catalyst is 3.0-4.5% of the feeding amount of ethyl chloroformate.
In the above method for producing an organic guanidine bactericide, further, in the production method, the organic solvent is chloroform (i.e., chloroform); the blending solvent is chloroform or toluene.
In the production method of the organic guanidine bactericide, the feeding molar ratio of the production raw materials of aminomethyl ethyl ester, cyanamide, dimethyl sulfate and dimethylamine is 1: 0.9-1.1: 0.9-1.1: 2.1 to 2.2.
The production method of the organic guanidine bactericide further comprises the step of controlling the content of the organic guanidine bactericide to be 80-82%.
The production method of the invention is adopted to produce the organic guanidine bactericide, and has at least the following beneficial effects: the catalyst is added for blending before the substitution reaction, and the substitution reaction is carried out after the blending, so that the substitution reaction can be rapidly carried out due to the existence of the catalyst even if a water phase and an organic phase exist in the system at the same time, and the industrial production efficiency is ensured.
Detailed Description
The present invention is further described below with reference to examples. It should be noted that the present invention is not limited to the following embodiments.
Example 1
The production process of organic guanidine bactericide includes the following steps:
(1) blending: adding 350Kg of water, 22Kg of 98% benzyltriethylammonium chloride and 800Kg of 30% cyanamide into a liquid caustic soda blending kettle, and starting a pump under the kettle to circulate the materials;
(2) and (3) substitution: 1670Kg of 30% caustic soda liquid is pumped into a head tank, and 665Kg of 98% ethyl chloroformate is pumped into the head tank by a vacuum pump; starting a liquid caustic soda blending kettle, freezing and keeping the temperature below 15 ℃, dropwise adding liquid caustic soda and ethyl chloroformate to react, keeping the reaction temperature at about 20 ℃, stopping dropwise adding when the pH =7 is the end point, and continuously stirring at about 20 ℃ for 1 h; after the reaction is finished, transferring the materials to a hydrolysate blending kettle, and starting a pump to make the materials internally circulate; the substitution reaction process is shown as the following formula:
(3) one-step synthesis: 30 Kg of 30% liquid caustic soda is thrown into a head tank, and 1065 Kg of 98% dimethyl sulfate is thrown into the head tank from a tank area; heating the materials in the hydrolysate blending kettle to 40 ℃, dropwise adding liquid caustic soda and dimethyl sulfate to react, controlling the pH to be =7.0, and controlling the temperature to be 40 ℃ for heat preservation reaction for 3 hours after dropwise adding; standing and layering after the reaction is finished, transferring the lower layer to a 15% hydrolysis kettle by a pump, and obtaining a one-step finished product of N-methyl cyanoethyl carbamate at the upper layer; extracting the lower layer liquid by using chloroform of 200L, and merging the desolventizing product after chloroform extraction into a finished product in one step; pumping the materials in the transfer tank into a liquid caustic soda dehydration kettle, heating the steam to about 40 ℃, cooling the residual chloroform to a liquid caustic soda dehydration recovery tank by a condenser, and sending the residual liquid to sewage treatment; the synthesis process is shown as the following formula;
(4) dissolving: 1440Kg of 40% dimethylamine was put into a 50% dissolution vessel, and 1556Kg of 30% hydrochloric acid was put into an overhead tank. Starting a dissolving kettle for freezing, starting a kettle lower pump to make the material internally circulate at 10 ℃, and dropwise adding hydrochloric acid to obtain the hydrochloride of dimethylamine;
(5) two-step synthesis: the hydrochloride of dimethylamine is pumped into a head tank, and the N-methyl cyanoethyl carbamate is pumped into a 15 percent dissolving kettle. Starting steam of the dissolution kettle, raising the temperature to 80 ℃, starting a kettle lower pump, dropwise adding hydrochloride of dimethylamine, and transferring the materials to a wastewater neutralization kettle through a pump after the reaction is finished; pumping the liquid caustic soda into a head tank; freezing a wastewater neutralization kettle, starting a kettle lower pump to circulate materials internally, dripping liquid alkali, pumping chloroform after the reaction is finished, standing for layering, enabling the lower layer to pass through a pump and a preheater to reach a scraper evaporator, and placing the upper layer into acidified wastewater for transferring to a tank; in the scraper evaporator, materials are preheated by a preheater (the heat source is from a hot water tank and is circulated by a pump), chloroform is cooled to a scraper water recovery tank by a condenser, a two-step finished product N-ethoxy-carbonyl-N, N ', N' -trimethylguanidine is cooled to a residual liquid storage tank by the condenser, and a semi-finished product is pumped to the top of the scraper evaporator again by a wastewater circulation transfer tank for circulation; the synthesis process is shown as the following formula, and the two-step finished product, namely the organic guanidine bactericide, is generated:
(6) blending: pumping the second-step finished product into a finished product preparation kettle, pumping chloroform for blending to obtain a finished product, namely the organic guanidine bactericide;
(7) recovering dimethylamine: pumping the liquid caustic soda into a head tank, transferring materials in a rotary tank in the acidified wastewater to a 50% hydrolysis kettle through a pump, dropwise adding the liquid caustic soda, adjusting the pH value to 7.0, starting steam, and cooling dimethylamine to a 50% hydrolysis recovery water tank through a condenser.
In the method, when the method is specifically implemented, the feeding molar ratio of the production raw materials of aminomethyl ethyl ester, cyanamide, dimethyl sulfate and dimethylamine is 1: 0.9-1.1: 0.9-1.1: 2.1-2.2, when the adding amount of the catalyst is 3.0-4.5% of the feeding amount of ethyl chloroformate, the substitution and synthesis reaction can be smoothly completed, and the production of the organic guanidine bactericide is realized; the dimethylamine is fed in excess, and can be used as reaction raw material, and can also be used as acid-binding agent by utilizing the alkalescence of the dimethylamine to absorb acidic substances in the reaction system, so that the acid does not influence the two-step synthesis reaction. In specific implementation, the organic solvent toluene can also be adopted to carry out two-step finished product blending to obtain the finished product of the organic guanidine bactericide.
The examples main equipment and results are as follows:
liquid caustic soda blending kettle, phi 1900 is multiplied by 2100mm, 5000L; a head tank with phi of 800 multiplied by 1000mm and 500L; a vacuum pump made of PP material; hydrolysate blending kettle, phi 1900 × 2100mm, 5000L; 15% hydrolysis kettle, phi 1900 x 2100mm, 5000L; condenser, contact area 30m2Stainless steel tubulation; 15% dissolving kettle, 1HF32-25-125 m; a wastewater neutralization kettle, CQB-50-32-125 combination; preheater, 20m2Stainless steel coil plate; scraper evaporator, 20m2(ii) a A finished product preparing kettle with phi 1900 multiplied by 2100mm and 5000L; a 50% hydrolysis recovery water tank with phi of 800X 2200mm and 1000L;
the raw materials adopted in the embodiment are obtained in a commercially available mode, and the preparation method is common knowledge in the industry; the results were as follows:
appearance: a light yellow oily liquid;
moisture content: 0.15 percent;
content of organic guanidine: 80.47 percent;
chloroform content: 0.72 percent.
In the finished bactericide product, during specific implementation, the content of the organic guanidine is detected by adopting an enterprise standard Q/JH0012-2019 gas chromatography, and a detection instrument of the bactericide product is GC-2010, a color matching spectrum workstation, an FID detector and a 10 mu L chromatography sample injector; the standard substance is purchased from Hubei on a network, and the content is 98.8 percent; the chromatographic conditions are as follows: a chromatographic column: HP-5, 30 m.times.0.32 m.times.0.25 um, column temperature: 145 ℃, vaporizer temperature: 270 ℃, detection chamber temperature: 270 ℃; carrier gas nitrogen gas: 5Mp, tail blown hydrogen: 0.1Mpa, combustion-supporting gas air: 0.08 MPa; feeding amount: 0.2 mu L; retention time: organoguanidine 10min, internal standard 7.231 min. Chloroform adopts GB/T4118-2008 industrial chloroform to detect the content, and the water content adopts a trace moisture tester to detect.
The standard requirement of the water content of the finished product is less than or equal to 0.2 percent, the standard requirement of the organic guanidine content is more than or equal to 80 percent, and the standard requirement of the chloroform content is less than or equal to 4 percent. The implementation result shows that the organic guanidine bactericide product produced by the production method meets the quality requirement.
Comparative example 1
The production method of the organic guanidine bactericide comprises the following production processes:
firstly, 350Kg of water and 22Kg of 98% benzyltriethylammonium chloride are added into a substitution reaction kettle, and a pump under the kettle is started to make the materials internally circulate; 1670Kg of 30% caustic soda liquid is pumped into a head tank, and 665Kg of 98% ethyl chloroformate is pumped into the head tank by a vacuum pump; starting a substitution reaction kettle, keeping the temperature below 15 ℃ for freezing, dropwise adding liquid caustic soda and ethyl chloroformate for reacting, keeping the reaction temperature at about 20 ℃, stopping dropwise adding when the pH =7 is the end point, and continuously stirring at about 20 ℃ for 1h to perform substitution reaction;
the rest of the one-step synthesis, dissolution, two-step synthesis and blending operations were the same as in example 1;
practice shows that in the substitution reaction of the comparative example, a water phase and an organic phase exist in the system at the same time, the substitution reaction is slow to carry out, and the dropwise addition needs 8 hours, so that the production efficiency is influenced; in example 1, after adding the catalyst in the blending step, the catalyst increases the transfer of the aqueous phase and the organic phase, and the dropwise addition of the base and the ethyl chloroformate only needs 2 to 3 hours, so that the substitution reaction can be rapidly carried out.
The present invention is not described in detail in the prior art.
Claims (6)
1. A production method of an organic guanidine bactericide is characterized by comprising the following steps: the production method comprises the following steps:
(1) blending: adding water, a catalyst and cyanamide into a liquid caustic soda blending kettle, and starting a kettle lower pump to circulate the materials;
(2) and (3) substitution: pumping the liquid caustic soda into an elevated tank, and pumping ethyl chloroformate into the elevated tank by using a vacuum pump; starting the chilled water of the liquid caustic soda blending kettle to keep the temperature of materials in the kettle below 15 ℃, dropwise adding the liquid caustic soda and ethyl chloroformate to react, keeping the reaction temperature at 15-25 ℃, stopping dropwise adding when the pH of the system is 6-7, and continuously stirring at 15-25 ℃ for 1-2 hours; transferring the material to a hydrolysate blending kettle, and starting a pump to circulate the material;
(3) one-step synthesis: pumping liquid caustic soda into a head tank, and pumping dimethyl sulfate into the head tank from a tank area; heating the materials in the hydrolysate blending kettle to 35-40 ℃, dropwise adding liquid caustic soda and dimethyl sulfate to react, controlling the pH = 7.0-7.2, and controlling the temperature at 35-40 ℃ after dropwise adding to react for 2-3 h; standing and layering after the reaction is finished, transferring the lower layer to a 15% hydrolysis kettle by a pump, and obtaining a one-step finished product of N-methyl cyanoethyl carbamate at the upper layer; extracting the lower layer liquid with organic solvent, merging the desolventizing product into one-step finished product after the organic solvent is extracted, pumping the raffinate into a liquid caustic soda dehydration kettle, raising the temperature with steam, cooling the residual organic solvent to a liquid caustic soda dehydration recovery tank through a condenser, and sending the raffinate to sewage treatment;
(4) dissolving: adding dimethylamine into a 50% dissolving kettle, and adding hydrochloric acid into an elevated tank; starting a 50% dissolving kettle for freezing, starting a kettle lower pump to circulate the materials at the temperature below 15 ℃, dropwise adding hydrochloric acid, and dissolving to obtain dimethylamine hydrochloride;
(5) two-step synthesis: injecting hydrochloride of dimethylamine into a head tank, and pumping N-methyl cyanoethyl carbamate into a 15% dissolving kettle; starting 15% of dissolving kettle steam, heating to 75-85 ℃, starting a kettle lower pump, dropwise adding dimethylamine hydrochloride, and transferring the materials to a wastewater neutralization kettle through a pump after the reaction is finished; pumping the liquid caustic soda into a head tank; starting a wastewater neutralization kettle for refrigeration, starting a kettle lower pump to enable materials to be internally circulated, dropwise adding liquid caustic soda until the pH of the system is 7-8, pumping an organic solvent after the reaction is finished, standing for layering, transferring a lower layer to a scraper evaporator through a pump and a preheater, and transferring an upper layer to an acidified wastewater for transferring to a tank; preheating materials in a scraper evaporator by a preheater, cooling an organic solvent to a scraper water recovery tank by a condenser, cooling a second-step finished product N-ethoxy-carbonyl-N, N ', N' -trimethylguanidine by the condenser, transferring the cooled second-step finished product to a storage tank, and pumping a semi-finished product into the top of the scraper evaporator again by a wastewater circulating transfer tank for circulation;
(6) blending: pumping the second-step finished product into a finished product preparation kettle, pumping a blending solvent for blending to obtain a finished product, namely the organic guanidine bactericide, wherein the structural formula of the organic guanidine bactericide is as follows:
2. the method for producing an organic guanidine bactericide as claimed in claim 1, wherein: the production method further comprises the following steps: (7) recovering dimethylamine: pumping the liquid caustic soda into a high-level tank, transferring materials in a rotary tank in the acidified wastewater into a 50% hydrolysis kettle through a pump, dropwise adding the liquid caustic soda, adjusting the pH value to 7.0-7.2, starting steam, and cooling dimethylamine to a 50% hydrolysis recovery water tank through a condenser.
3. The method for producing an organic guanidine bactericide as claimed in claim 1, wherein: in the step (1), the catalyst is benzyltriethylammonium chloride, and the adding amount of the catalyst is 4.0-4.5% of the feeding amount of ethyl chloroformate.
4. The method for producing an organic guanidine bactericide as claimed in claim 1, wherein: in the production method, the organic solvent is chloroform; the blending solvent is chloroform or toluene.
5. The method for producing an organic guanidine bactericide as claimed in claim 1, wherein: the production raw materials of aminomethyl ethyl ester, cyanamide, dimethyl sulfate and dimethylamine are fed in a molar ratio of 1: 0.9-1.1: 0.9-1.1: 2.1 to 2.2.
6. The method for producing an organic guanidine bactericide as claimed in claim 1, wherein: the content of the organic guanidine bactericide is 80-82%.
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| CN111825571A (en) * | 2020-06-24 | 2020-10-27 | 江苏蓝丰生物化工股份有限公司 | Method for synthesizing N-methyl cyanoethyl carbamate by using methylating reagent |
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Application publication date: 20200421 |