CN1520902A - Recovery processing method for production waste of organosilane coupling agent containing beta-qae-gamma-aminopropyl group - Google Patents
Recovery processing method for production waste of organosilane coupling agent containing beta-qae-gamma-aminopropyl group Download PDFInfo
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- CN1520902A CN1520902A CNA031128742A CN03112874A CN1520902A CN 1520902 A CN1520902 A CN 1520902A CN A031128742 A CNA031128742 A CN A031128742A CN 03112874 A CN03112874 A CN 03112874A CN 1520902 A CN1520902 A CN 1520902A
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- aminoethyl
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Abstract
The recovering treatment process of waste from organosilicon coupling agent production and containing beta-azyloxy-gamma-aminopropyl radical includes heating distillation and condensating recovery of the waste added with strong alkaline matter in some reactor to recover ethylenediamine; and subsequent cooling of the reaction mixture while adding water to regulate pH value for effective laminating separation to separate organosilicon coupling agent in the upper layer of the reaction mixture. The present invention has the advantages of less investment in apparatus, simple technological process, simple operation and elimination of secondary pollution.
Description
Technical Field
The invention belongs to the field of organic chemical industry, and particularly relates to a recovery treatment method of production waste generated in the production of an organosilane coupling agent containing β -aminoethyl-gamma-aminopropyl groups.
Background
The structural formula of the organosilane coupling agent is RSiX3The R group and the X group can be divided into a plurality of different varieties due to different difference, wherein the R group is a hydrocarbon group, an aromatic group or a composite group with amino, and the X group is a methoxy group, or a methoxy group and an alkyl group, or an ethoxy group and an alkyl group2-CH2-CH2-NH-CH2-CH2-CH2-，
For example, the chemical name of (A) is N- β -aminoethyl-gamma-aminopropyl-trimethoxy silane, the chemical formula is as follows:
the chemical name is N- β -aminoethyl-gamma-aminopropyl-methyldimethoxysilane, and the chemical formula is as follows:
the chemical name is N- β -aminoethyl-gamma-aminopropyl-methyldiethoxysilane, and the chemical formula is as follows:
the chemical name of the compound is N- β -aminoethyl-gamma-aminopropyl-triethoxysilane, and the chemical formula is as follows:
at present, enterprises producing organosilane coupling agents containing β -aminoethyl-gamma-aminopropyl groups are produced by a plurality of enterprises, and the enterprises inevitably generate corresponding organic production waste materials in the process of producing the organosilane coupling agents, and the organic production waste materials contain more ethylenediamine and ethylenediamine hydrochloride and also inevitably contain corresponding organosilane coupling agents due to the factors of production processes.
Themethod comprises the steps of (a) providing common people for local fish culture without compensation as fish feed, wherein the organic production waste possibly contains harmful substances, and after the fish is eaten for a long time, the harmful substances can be accumulated in the fish body, so that the physical health of people eating the fish can be influenced, (b) purchasing quicklime by some manufacturers for neutralization treatment, and then burying the waste subjected to the neutralization treatment, wherein the method not only needs certain treatment cost, but also needs about 300 yuan per treated organic waste through calculation, and causes secondary pollution to the environment due to the buried waste, and (c) sending the organic production waste to a fixed-point recovery treatment station of a local environmental protection department for centralized treatment, but generally needs a certain cost, about 300 yuan per ton, and additionally needs about 400 yuan per ton, so that the production cost of enterprises is greatly increased.
Disclosure of Invention
In view of the above problems, the present invention provides a novel recycling method, which is simple and convenient to operate, and can effectively recycle the active ingredients in the production waste generated in the process of producing the organic silane coupling agent containing β -aminoethyl- γ -aminopropyl group.
The main process principle of the technical scheme adopted by the invention is that the production waste material of the organosilane coupling agent containing β -aminoethyl-gamma-aminopropyl groups and excessive strong alkaline substances are put into a reaction kettle, then heating distillation is carried out, the ethylenediamine hydrochloride in the production waste material reacts with the strong alkaline substances, and the ethylenediamine is recovered by a condensation recovery treatment process during the heating distillation.
The above-mentioned ethylenediamine is called Ethylenediamine in English, and is abbreviated as EDA, and its molecular formula is C2H8N2Molecular weight of 60.11, and structural formula of H2N-CH2-CH2-NH2Is a commonly used organic compound. At normal temperature and normal pressure, the product is colorless, has strong basicity, is volatile, is viscous liquid, has ammonia smell, can be fuming in air, can be mutually soluble with solvents such as water, ethanol and the like in any proportion, is slightly soluble in ether, and is insoluble in benzene. Ethylenediamine (EDA) is commonly used in non-aqueous titration for ammine-hydroxo-complexing agents, for the detection of beryllium, cerium, magnesium, nickel, thorium, titanium, uranium, lanthanum, for the detection of antimony, bismuth, copper, mercury, silver, cadmium, uranium, as well as curing agents for epoxy resins, solvents for protein fiber glues, in the pharmaceutical industry and in organic synthesis, etc.
The following describes in detail the treatment method employed in the present invention:
the method for recycling the production waste of the organic silane coupling agent containing β -aminoethyl-gamma-aminopropyl groups mainly comprises the following steps:
(1) putting a certain amount of production waste of the organic silane coupling agent containing β -aminoethyl-gamma-aminopropyl groups and excessive strong alkaline substances into a reaction kettle, and then starting heating and distilling;
(2) the ethylene diamine can be recovered by condensing and recovering the distilled steam while heating and distilling.
A further scheme of the treatment method is as follows: ofthe two reaction materials described in the above step (1)The ratio of the production waste per 100 g of the organosilane coupling agent containing β -aminoethyl-gamma-aminopropyl groups is equivalent to the ratio of the production waste containing OH-The amount of the substance (b) is 1 mole or more of a strongly basic substance.
A further scheme of the treatment method is that the strong alkaline substance is NaOH, and the proportion of the production waste of the organic silane coupling agent containing β -aminoethyl-gamma-aminopropyl groups to the NaOH is 100: 40-80 by weight.
In another further scheme of the treatment method, the strong alkaline substance is CaO, and the proportion of the production waste of the organic silane coupling agent containing β -aminoethyl-gamma-aminopropyl groups to CaO is in the range of 100: 30-60 by weight.
In the above-mentioned process of heating and distilling, the temperature of heating and distilling is controlled to be 90 ℃ or higher. Wherein the optimal temperature range is between 100 ℃ and 140 ℃.
The other further scheme of the treatment method is as follows: after the ethylenediamine is completely recovered, standing and cooling the reaction mixture in the reaction kettle, and then adding water into the reaction kettle to adjust the pH value of the reaction mixture, so that the reaction mixture in the reaction kettle is naturally layered, and the organosilane coupling agent is positioned at the uppermost layer of the reaction mixture; finally, the corresponding organosilane coupling agent can be obtained by a liquid separation method.
In the above process of adjusting the pH value by adding water, the pH value of the reaction mixture in the reaction kettle can be controlled between 7.0 and 9.0. And the temperature in the reaction kettle is controlled within the range of 15-90 ℃ during cooling.
The method has the advantages that firstly, the equipment investment is less, the process is simple, the operation is convenient, secondly, the worries of enterprises producing organosilane coupling agents containing β -aminoethyl-gamma-aminopropyl groups can be solved, the production cost of the enterprises can be saved, about 500 yuan per ton of waste treatment cost can be saved, waste can be changed into valuable, the production waste can be sold at about 500 yuan per ton, so that the economic income of 1000 yuan per ton can be increased for the enterprises, thirdly, by adopting the treatment method, the equipment investment is less due to the cheap raw materials, the operation process is simple, the production cost is lower, the produced ethylenediamine and the corresponding organosilane coupling agent have extremely strong market competitiveness, for example, the market price of the ethylenediamine with the concentration of 90% produced by the common production process is about 11000 yuan per ton, and the market price of the ethylenediamine with the same concentration produced by the method is only about 9000 yuan per ton.
Detailed description of the preferred embodiments
The recycling method of the present invention will be further described with reference to examples.
In the examples, the production waste is the production waste of an organosilane coupling agent containing β -aminoethyl-gamma-aminopropyl groups, the strong alkaline substance adopts NaOH and CaO, and the reaction equation of the sodium hydroxide and the ethylenediamine hydrochloride is as follows:
the reaction equation of CaO andethylenediamine salt solution is:
example 1:
in this example, the concentrations of ethylenediamine hydrochloride and ethylenediamine in the production waste used were about 70%.
Taking 100 g of the production waste, putting the production waste into a flask, adding 60 g of NaOH, heating and distilling, and keeping the temperature at about 100 ℃, wherein the ethylenediamine hydrochloride in the production waste is reacted with the sodium hydroxide to generate ethylenediamine, and the ethylenediamine is gasified and volatilized, so that the distilled gas is condensed and recycled while distilling, and the ethylenediamine can be recovered; when the recovery of ethylenediamine was completed, 64.2 g of ethylenediamine was obtained in total by weighing. Then, the reaction mixture in the flask is cooled to below 80 ℃, generally to the normal temperature, and water is added into the flask to adjust the pH value of the reaction mixture and the pH value of the reaction mixture to about 7.0; the flask was allowed to stand for about 30 minutes until the reaction mixture was separated into layers, in which case the corresponding organosilane coupling agent was present in the upper layer of the reaction mixture and the NaCl solution was present in the lower layer of the reaction mixture, and the corresponding organosilane coupling agent was obtained by separation and separation, and weighed 8.9 g. Meanwhile, the NaCl solution can be separated out for other industrial purposes.
Therefore, the treatment method of the embodiment has no secondary pollution and has good economic, social and ecological benefits.
Example 2:
in this example, the concentrations of ethylenediamine hydrochloride and ethylenediamine in the production waste used were about 60%.
100 g of the above production waste was taken and put into a flask, and 45 g of CaO was added thereto, followed byHeating and distilling the mixture, and keeping the temperature at about 115 ℃, wherein the ethylenediamine generated by the reaction of ethylenediamine hydrochloride in the production waste and CaO is gasified and volatilized, so that the distilled gas is condensed and recycled while distilling, and the ethylenediamine can be recycled; when the recovery of ethylenediamine was completed, 56.2 g of ethylenediamine was obtained in total by weighing. Then, the reaction mixture in the flask is cooled to below 90 ℃, generally to normal temperature, and water is added into the flask to adjust the pH value of the reaction mixture and the pH value of the reaction mixture to about 8.0; the flask was allowed to stand for about 30 minutes until the reaction mixture therein was separated into layers, at which time the corresponding organosilane coupling agent was located in the upper layer of the reaction mixture and CaCl was located in the lower layer of the reaction mixture2The solution was separated by liquid separation to give the corresponding organosilane coupling agent, which was weighed to 9.2 g. Meanwhile, CaCl can also be added2The solution is separated out for other industrial uses.
Therefore, the treatment method of the embodiment has no secondary pollution and has good economic, social and ecological benefits.
Example 3:
in this example, the concentrations of ethylenediamine hydrochloride and ethylenediamine in the production waste used were about 70%.
Taking 100 g of the production waste, putting the production waste into a flask, adding 60 g of NaOH, heating and distilling, and keeping the temperature at about 130 ℃, wherein the ethylenediamine hydrochloride in the production waste is reacted with the sodium hydroxide to generate ethylenediamine, and the ethylenediamine is gasified and volatilized, so that the distilled gas is condensed and recycled while distilling, and the ethylenediamine can be recovered; when the recovery of ethylenediamine was completed, 64.2 g of ethylenediamine was obtained in total by weighing. Then, the reaction mixture in the flask is cooled to below 70 ℃, generally to the normal temperature, and water is added into the flask to adjust the pH value of the reaction mixture and the pH value of the reaction mixture to about 9.0; the flask was allowed to stand for about 30 minutes until the reaction mixture was separated into layers, in which case the corresponding organosilane coupling agent was present in the upper layer of the reaction mixture and the NaCl solution was present in the lower layer of the reaction mixture, and the corresponding organosilane coupling agent was obtained by separation and separation, and weighed 8.9 g. Meanwhile, the NaCl solution can be separated out for other industrial purposes.
Therefore, the treatment method of the embodiment has no secondary pollution and has good economic, social and ecological benefits.
Claims (9)
1. The method for recycling and treating the production waste of the organic silane coupling agent containing β -aminoethyl-gamma-aminopropyl groups is characterized by mainly comprising the following steps of:
(1) putting a certain amount of production waste of the organic silane coupling agent containing β -aminoethyl-gamma-aminopropyl groups and excessive strong alkaline substances into a reaction kettle, and then starting heating and distilling;
(2) the ethylene diamine can be recovered by condensing and recovering the distilled steam while heatingand distilling.
2. The recycling treatment method according to claim 1, wherein the ratio of the two reaction materials in the step (1) is in the range of β -aminoethyl- γ -aminopropyl group-containing organosilane coupling agent production waste per 100 g, which is equivalent to OH-containing organosilane coupling agent-The amount of the substance (b) is 1 mole or more of a strongly basic substance.
3. The recycling method according to claim 1 or 2, wherein the strongly alkaline substance is NaOH, and the ratio of the production waste of the organosilane coupling agent containing β -aminoethyl- γ -aminopropyl group to NaOH is in the range of 100: 40-80 by weight.
4. The recycling treatment method according to claim 1 or 2, wherein the strongly alkaline substance is CaO, and the ratio of the production waste of the organosilane coupling agent containing β -aminoethyl- γ -aminopropyl groups to CaO is in the range of 100: 30-60 by weight.
5. The recycling method according to claim 1, wherein: the temperature of the heating distillation is controlled to be above 90 ℃.
6. The recycling treatment method according to claim 1 or 5, characterized in that: the temperature of the heating distillation is controlled within the range of 100 ℃ to 140 ℃.
7. The recycling method according to claim 1, wherein: after the ethylenediamine is completely recovered, standing and cooling the reaction mixture in the reaction kettle, and then adding water into the reaction kettle to adjust the pH value of the reactionmixture, so that the reaction mixture in the reaction kettle is naturally layered, and the organosilane coupling agent is positioned at the uppermost layer of the reaction mixture; finally, the corresponding organosilane coupling agent can be obtained by a liquid separation method.
8. The recycling treatment method according to claim 7, wherein: after water is added, the pH value of the reaction mixture in the reaction kettle is controlled between 7.0 and 9.0.
9. The recycling treatment method according to claim 7, wherein: and controlling the temperature in the reaction kettle within the range of 15-90 ℃ during cooling.
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| CNB031128742A CN100413555C (en) | 2003-02-10 | 2003-02-10 | Recovery processing method for production waste of organosilane coupling agent containing beta-qae-gamma-aminopropyl group |
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| CNB031128742A CN100413555C (en) | 2003-02-10 | 2003-02-10 | Recovery processing method for production waste of organosilane coupling agent containing beta-qae-gamma-aminopropyl group |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102898460A (en) * | 2012-10-21 | 2013-01-30 | 荆州市江汉精细化工有限公司 | Technology for preparing double-amino silane and treating by-product |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2713676B2 (en) * | 1992-01-20 | 1998-02-16 | 信越化学工業株式会社 | Method for producing 3- [N- (2-aminoethyl)] aminopropylalkoxysilane and apparatus for producing the same |
| JP2785622B2 (en) * | 1992-10-26 | 1998-08-13 | 信越化学工業株式会社 | Method for producing 3- [N- (2-aminoethyl)] aminopropylalkoxysilane and apparatus for producing the same |
| US6452033B1 (en) * | 2002-02-11 | 2002-09-17 | Dow Corning Corporation | Method of making N-[2-aminoethyl] aminoalkylalkoxysilanes with ethyenediamine salt recycle |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102898460A (en) * | 2012-10-21 | 2013-01-30 | 荆州市江汉精细化工有限公司 | Technology for preparing double-amino silane and treating by-product |
| CN102898460B (en) * | 2012-10-21 | 2015-03-11 | 荆州市江汉精细化工有限公司 | Technology for preparing double-amino silane and treating by-product |
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