CN103804257A - Synthesis process based on control of pH value for diethyldithiocarbamate - Google Patents
Synthesis process based on control of pH value for diethyldithiocarbamate Download PDFInfo
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- CN103804257A CN103804257A CN201210480178.1A CN201210480178A CN103804257A CN 103804257 A CN103804257 A CN 103804257A CN 201210480178 A CN201210480178 A CN 201210480178A CN 103804257 A CN103804257 A CN 103804257A
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- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 22
- 230000008569 process Effects 0.000 title abstract description 10
- LMBWSYZSUOEYSN-UHFFFAOYSA-N diethyldithiocarbamic acid Chemical compound CCN(CC)C(S)=S LMBWSYZSUOEYSN-UHFFFAOYSA-N 0.000 title abstract description 9
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- 238000006243 chemical reaction Methods 0.000 claims abstract description 40
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- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 1
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- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 1
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- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a synthesis process based on control of the pH value for diethyldithiocarbamate. The process comprises the following steps: (a) adding a certain amount of carbon disulfide, alkali liquor and carbamide into a reaction container; (b) stirring continuously till mixing uniformly, controlling the temperature, and dropwise adding carbon disulfide; (c) controlling a reaction system within a certain temperature range, adjusting the pH value of the reaction system to 6.0-8.0, and stirring for a certain period; (d) heating to a certain temperature, and reacting at a constant temperature for a certain period; (e) after reacting, stirring and cooling for crystallizing, and filtering; (f) performing vacuum drying to obtain a product. The diethyldithiocarbamate is synthesized by using carbon disulfide and carbamide according to certain process parameters, the synthesis steps are simple, the synthesis efficiency is high, the synthesis cost is low, and the synthesized product is efficient, cheap and wide in the application range. Moreover, by controlling the pH value of the reaction system, the conversion rate of the entire process is increased, and the product quality is improved.
Description
Technical field
The present invention relates to a kind of synthesis technique of the dithiocar-bamate based on control pH value.
Background technology
Dithiocar-bamate, referred to as DTC, is just reacted and is synthesized with CS2 by organic primary amine or secondary amine in laboratory in mid-term in 19th century.At present, dithiocar-bamate and derivative thereof are widely used in the fields such as rubber, oil, agricultural, mining industry, medicine, environment protection and analytical chemistry as degreaser, water quality cleansing agent, Scale inhibitors, membrane-forming agent and resistance to compression additive etc.After, the Application Areas of such material will further expand.
In petroleum industry, dithiocarbamate(s) compound is mainly used as extreme pressure antiwear agent for lubricant oil, high-temperature antioxidant.Because can making the poisoning of catalyst of engine exhaust transfer equipment, the phosphoric in the dithiophosphates class lubricating oil wear preventive additive generally using now lost efficacy, moreover consideration based on environmental protection aspect, various countries have all made strict regulation to the content of phosphorus in the lubricating oil such as machine oil, require to use low ash, low-phosphorous lubricating oil.Dithiocarbamate(s) compound is because having excellent extreme-pressure anti-wear and high-temperature oxidation resistance, and phosphorus element-containing not, and toxicity is low, is expected to become the substitute products of dithiophosphates class lubricating oil wear preventive additive.To a study hotspot that synthesizes and become as the applied research of lubrication oil antiwear oxidation inhibitor current lubricating oil additive of novel dithiocarbamate(s) compound.
In rubber industry, dithiocarbamate(s) compound is mainly as thiofide.It promotes that sulfuration effect is very large, as the second promotor and time sulfonephthalein amine vulcanization accelerator use, can shorten curing time, and its consumption is only second to time sulfonephthalein amine type accelerator at present.
In plastics industry, the application of dithiocarbamate(s) compound mainly contains two aspects.The initiator while being used as high molecular polymerization on the one hand.Dithiocar-bamate can be controlled the putting in order and the taxis of some polymkeric substance etc. of molecular weight, molecular weight distribution, end-group structure, side group structure, monomer of resulting polymers effectively as photoactivation type agent, also can by molecular designing synthesize diversified, there is the multicomponent copolymer of specified property or function and have particular geometry Model Polymers etc.; Be as plastics oxidation inhibitor and photodegradation sensitizing agent on the other hand, study at most as plastics photodissociation sensitizing agent with dithiocarbamic acid iron class material.
In environment protection, because dithiocarbamate(s) compound has polar group, the sulfonium ion atomic radius in this polar group is larger; electronegative, be easy to waste water in metallic cation Cheng Jian, generate the dithiocar-bamate of indissoluble; therefore, be commonly used for extraction intercalating agent.Be mainly used in two aspects.Make precipitate flotation agent and solvent sublation collecting agent by low-molecular-weight dithiocar-bamate on the one hand, separate the heavy metal ion in wastewater treatment and be used as the complexing agent in supercritical fluid chelating extraction.Moreover be that amino dithio carbonyl is introduced to polystyrene polymethacrylate derivative, contained in the high molecular polymer such as polymkeric substance and the polyethers skeleton of polyethylene polyamine, preparation has chelate resin or the water miscible chelate resin of certain physical strength.Water miscible dithiocar-bamate chelate resin is the novel oilfield sewage-treating agent growing up in the U.S. nineteen nineties, has efficient degreasing performance, also has the functions such as sterilization, antiscale, inhibition simultaneously.
In mining industry, dithiocarbamate(s) compound is mainly as flotation collector.Dialkyl dithiocarbamate compounds is a kind of metal sulfide collecting agent efficiently, has the features such as collecting ability is strong, selectivity is high, dosage is few, flotation speed is fast.Be commonly used for the flotation collector of the mineral such as lead glance, chalcopyrite.As being used for carrying out lead glance and zink sulphide, pyritous flotation separation under Thiocarb (No. nine, sulphur nitrogen) the high-alkali condition of being everlasting, it is to the stronger collecting effect of lead glance performance.
In agricultural, dithiocarbamate(s) compound is mainly as disinfectant use in agriculture.Through the development of decades, develop the sterilant such as Karbam Black, ziram, thiram, Parzate, zineb, maneb and zinc manganese ethylenebisdithiocarbamate, what wherein purposes was the widest is zinc manganese ethylenebisdithiocarbamate.
Medically, dithiocarbamate(s) compound is mainly as the toxinicide of heavy metal poisoning, as carcinostatic agent, as immunomodulator, medical oxidation inhibitor and external application sterilant.
In analytical chemistry, dithiocarbamate(s) compound is mainly as extraction complexing agent, for separation and the pre-concentration of chromatogram, spectroscopic analysis.Can be used for analyzing the trace analysis of the various metals such as arsenic, chromium, lead, copper, nickel, zinc, manganese, silver and non-metallic element.
Although DTC and derivative thereof are the novel oilfield treatment agents growing up in the U.S. nineteen nineties, nowadays in ground widespread uses such as oil field, the North Sea, the Gulfian, and China is little to the research of this class chemical agent, as research and the practice situation thereof of inhibiter aspect, domestic report just still less.
At present domestic have two aspects to DTC class inhibiter Shortcomings part:
(1) exist raw materials used cost high, more difficult a large amount of acquisitions.To polyethylene polyamine materials such as quadrol, diethylenetriamine, triethylene tetramines as reactant, although research has confirmed that such material corrosion inhibition effect is pretty good, but because these raw materials cost are too high and more difficult obtaining, if promote the use of, there is great difficulty on a large scale in brill well-completion practice.
(2) to the research of corrosive medium system very little.Domestic this minute quantity research is the only research of the corrosion inhibition in acidic corrosive media system and the discussion at theoretical side for this class material of DTC also, and the not systematically research to DTC class inhibiter corrosion inhibition in corrosive medium system neutral, alkaline and that various different brine corrosion medium systems, particularly Oil/gas Well are more complicated.Therefore be necessary other corrosive medium system to carry out systematic Study.For this reason, synthesizing efficient cheapness, the dithiocarbamate(s) inhibiter having wide range of applications and research of the corrosion inhibition in different corrosive medium systems to it, just seem necessary.
In the process of synthetic dithiocar-bamate, the pH value of different reaction systems can be on the technique in building-up process transformation efficiency and the very large impact of mass formation of product, so, determine the pH value of a suitable reaction system, the synthesis technique of dithiocar-bamate is seemed to particularly important.
Summary of the invention
The object of the invention is to overcome the shortcoming and defect of above-mentioned prior art, a kind of synthesis technique of the dithiocar-bamate based on control pH value is provided, this synthesis technique is by synthesizing dithiocar-bamate by dithiocarbonic anhydride and carbonyl diamine according to certain processing parameter, synthesis step is simple, combined coefficient is high, synthetic cost is low, the product that synthesizes efficient cheap, have wide range of applications, and by controlling the pH value of reaction system, thereby improve the quality of transformation efficiency and the product of whole technique.
Object of the present invention is achieved through the following technical solutions: a kind of synthesis technique of the dithiocar-bamate based on control pH value, comprises the following steps:
(a) first, in reaction vessel, add a certain amount of dithiocarbonic anhydride, alkali lye and carbonyl diamine;
(b) constantly stir, after it mixes, control temperature, drip dithiocarbonic anhydride;
(c) reaction system is controlled in certain temperature range, and to regulate the pH value of reaction system be 6.0～8.0, stir for some time;
(d) then, reheat after certain temperature isothermal reaction certain hour;
(e) question response is complete, stirs crystallisation by cooling, filters;
(f) vacuum-drying, makes product.
After described step (f) finishes, weigh quality product, and sampling analysis product content, efficiency of pcr product calculated.
Described alkali lye is potassium hydroxide.
Described reaction vessel is there-necked flask.
In described step (c), regulating the pH value of reaction system is 6.5.
In described step (c), regulating the pH value of reaction system is 7.0.
In described step (c), regulating the pH value of reaction system is 7.5.
In sum, the invention has the beneficial effects as follows: by dithiocarbonic anhydride and carbonyl diamine are synthesized to dithiocar-bamate according to certain processing parameter, synthesis step is simple, combined coefficient is high, synthetic cost is low, the product that synthesizes efficient cheap, have wide range of applications, and by controlling the pH value of reaction system, thereby improve the quality of transformation efficiency and the product of whole technique.
Embodiment
Below in conjunction with embodiment, the present invention is described in further detail, but embodiments of the present invention are not limited only to this.
Embodiment:
The synthesis technique of a kind of dithiocar-bamate based on control pH value the present invention relates to, its concrete steps are as follows:
(a) first, in reaction vessel, add a certain amount of dithiocarbonic anhydride, alkali lye and carbonyl diamine;
(b) constantly stir, after it mixes, control temperature, drip dithiocarbonic anhydride;
(c) reaction system is controlled in certain temperature range, and to regulate the pH value of reaction system be 6.0～8.0, stir for some time;
(d) then, reheat after certain temperature isothermal reaction certain hour;
(e) question response is complete, stirs crystallisation by cooling, filters;
(f) vacuum-drying, makes product.
After described step (f) finishes, weigh quality product, and sampling analysis product content, efficiency of pcr product calculated.
Described alkali lye is potassium hydroxide.
Described reaction vessel is there-necked flask.
In described step (c), regulating the pH value of reaction system is 6.5.
In described step (c), regulating the pH value of reaction system is 7.0.
In described step (c), regulating the pH value of reaction system is 7.5.
In the process of synthetic dithiocar-bamate, the pH value of different reaction systems can be on the technique in building-up process transformation efficiency and the very large impact of mass formation of product, so, determine the pH value of a suitable reaction system, the synthesis technique of dithiocar-bamate is seemed to particularly important.In order to obtain the pH value of suitable reaction system, the present invention has done the transformation efficiency of technique of pH value on building-up process and the impact experiment of the quality of product of differential responses systems, result is known by experiment: in the time that the pH of reaction system value is positioned at 6.0～8.0, near neutral time, the transformation efficiency of reaction is all the trend increasing gradually, but, in the time that the pH of reaction system value exceedes 7.0, can reduce the quality of product, therefore should increase and consider, in the present invention, the pH value of reaction system is 6.0～8.0, and the best is 7.0.
The above, be only preferred embodiment of the present invention, not the present invention done to any pro forma restriction, every foundation technical spirit of the present invention, and any simple modification, equivalent variations that above embodiment is done, within all falling into protection scope of the present invention.
Claims (7)
1. the synthesis technique of the dithiocar-bamate based on control pH value, is characterized in that, comprises the following steps:
(a) first, in reaction vessel, add a certain amount of dithiocarbonic anhydride, alkali lye and carbonyl diamine;
(b) constantly stir, after it mixes, control temperature, drip dithiocarbonic anhydride;
(c) reaction system is controlled in certain temperature range, and to regulate the pH value of reaction system be 6.0～8.0, stir for some time;
(d) then, reheat after certain temperature isothermal reaction certain hour;
(e) question response is complete, stirs crystallisation by cooling, filters;
(f) vacuum-drying, makes product.
2. the synthesis technique of the dithiocar-bamate based on control pH value according to claim 1, is characterized in that, after described step (f) finishes, weighs quality product, and sampling analysis product content, calculates efficiency of pcr product.
3. the synthesis technique of the dithiocar-bamate based on control pH value according to claim 1, is characterized in that, described alkali lye is potassium hydroxide.
4. the synthesis technique of the dithiocar-bamate based on control pH value according to claim 1, is characterized in that, described reaction vessel is there-necked flask.
5. the synthesis technique of the dithiocar-bamate based on control pH value according to claim 1, is characterized in that, in described step (c), regulating the pH value of reaction system is 6.5.
6. the synthesis technique of the dithiocar-bamate based on control pH value according to claim 1, is characterized in that, in described step (c), regulating the pH value of reaction system is 7.0.
7. the synthesis technique of the dithiocar-bamate based on control pH value according to claim 1, is characterized in that, in described step (c), regulating the pH value of reaction system is 7.5.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2018122510A1 (en) | 2016-12-29 | 2018-07-05 | Arkema France | Functionalised cyclic dithiocarbamate synthesis method |
| US11643673B2 (en) | 2016-12-29 | 2023-05-09 | Arkema France | Functionalised cyclic dithiocarbamate synthesis method |
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