CN113416421B - Preparation method and application of bio-based deodorant - Google Patents
Preparation method and application of bio-based deodorant Download PDFInfo
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- CN113416421B CN113416421B CN202110544230.4A CN202110544230A CN113416421B CN 113416421 B CN113416421 B CN 113416421B CN 202110544230 A CN202110544230 A CN 202110544230A CN 113416421 B CN113416421 B CN 113416421B
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L95/00—Compositions of bituminous materials, e.g. asphalt, tar, pitch
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/101—Esters; Ether-esters of monocarboxylic acids
- C08K5/105—Esters; Ether-esters of monocarboxylic acids with phenols
- C08K5/107—Esters; Ether-esters of monocarboxylic acids with phenols with polyphenols
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K7/00—Use of ingredients characterised by shape
- C08K7/22—Expanded, porous or hollow particles
- C08K7/24—Expanded, porous or hollow particles inorganic
- C08K7/26—Silicon- containing compounds
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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Abstract
The invention relates to the technical field of highway asphalt, in particular to a bio-based deodorant, and a preparation method and application thereof, and the bio-based deodorant is prepared from 40-60 parts of 3, 4-dioleyloxy-a-methyl phenylpropenoic aldehyde, 40-60 parts of nano white carbon black, 0.3-0.5 part of antioxidant and 1-3 parts of polyethylene wax. In the using process, the Schefflerin can form Schefflerin substances with amino groups in the asphalt; and stable mercaptal is formed with hydrogen sulfide, mercaptan and the like generated in the development process of adding the stabilizer, so that toxic gas does not overflow any more, and the use pollution is reduced. The synthetic raw materials are all derived from natural substances, such as 3, 4-dihydroxy benzaldehyde extracted from root of Salvia miltiorrhiza Bunge of Labiatae, and linoleic acid extracted from various oil crops. The synthetic method is green, environment-friendly and pollution-free; the synthetic product can be degraded and can be degraded by bacteria microorganisms after the pavement reaches the service life. The synthetic raw materials have special plant fragrance, and can relieve the discomfort of operators caused by peculiar smell generated in the asphalt mixing process.
Description
Technical Field
The invention relates to the technical field of highway asphalt, in particular to a bio-based deodorant and a preparation method and application thereof.
Background
The minor components such as aromatic amino groups contained in the asphalt are the main sources of the odor of the base asphalt. When the asphalt is modified, a modifier containing sulfur simple substance is added, so that odorous gases such as hydrogen sulfide, mercaptan and the like can be generated at high temperature, and great harm is also brought to operators and natural environment. Asphalt, especially coal asphalt, can volatilize some polyaromatic hydrocarbon structure compounds when preparing asphalt mixture or paving road surface in hot mixing, and the compounds have been proved to have carcinogenic risk by research. Therefore, the method reduces or avoids the volatilization and overflow of odor substances in the asphalt in the treatment process at high temperature, and is very important for protecting the environment and creating a safe production environment for operators.
Disclosure of Invention
Aiming at the problems in the prior art, the invention aims to provide a bio-based deodorant which can react with odor substances of an asphalt mixture to convert the odor substances into non-toxic or low-toxic substances so as to achieve the aim of deodorizing. In addition, the invention also provides a preparation method and application of the biotechnology deodorant.
In order to realize the purpose, the technical scheme provided by the invention is as follows:
the invention provides a preparation method of a bio-based deodorant, which comprises the following steps:
step one, synthesizing 4-formyl-catechol dilinoleate;
step two, synthesizing 3, 4-dilinoleic acyloxy-a-methyl phenylpropenoic aldehyde;
and step three, preparing the bio-based deodorant from the 3, 4-dioleyloxy-a-methyl phenylpropenoic aldehyde, the nano white carbon black, the antioxidant and the separant.
On the basis of the scheme, step one, adding a toluene solvent, 1mol of 3, 4-dihydroxybenzaldehyde, 2mol of linoleic acid, 2.2mol of diethyl azodicarboxylate and 2.2mol of triphenylphosphine into a three-neck flask for stirring reaction; after vacuumizing and nitrogen replacement, the three-neck flask is continuously stirred and reacts for 12 hours at 120 ℃; cooling the reactant to 0 ℃ in an ice water bath, and adding ice water for quenching; after the organic phase is subjected to liquid separation, respectively washing, drying, filtering and concentrating to obtain a light yellow crude product; separating and purifying the crude product by column chromatography to obtain a white product 4-formyl-catechol dilinoleate;
step two, dissolving 1.1mol of n-propionaldehyde and 1mol of 4-formyl-catechol dilinoleate prepared in the step one in an ethanol solution under the protection of nitrogen, uniformly stirring and cooling to-10 ℃; slowly dropwise adding a saturated sodium bicarbonate solution into the reaction system, and reacting for 12 hours at-10 ℃; after detecting that 4-formyl-catechol dilinoleate reacts completely by an HPLC method, adding ice water into reaction liquid, violently stirring, separating out white solid, filtering, and drying at room temperature to obtain 3, 4-dilinoleoyloxy-a-methyl phenylpropyl aldehyde;
and step three, adding 40-60 parts of 3, 4-dioleyloxy-a-methyl phenylpropyl aldehyde, 40-60 parts of nano white carbon black and 0.3-0.5 part of antioxidant obtained in the step two into a mixing tank, mixing and stirring for 1h under the test conditions of the temperature of 30 ℃ and the rotation speed of 500rpm, then adding 1-3 parts of separant, and continuing mixing and stirring for 30min to obtain the bio-based deodorant.
The specific synthetic route of the invention is shown as follows, the final synthetic product of the invention mainly becomes active phenylpropenoic aldehyde in 3, 4-dilinoleic acyloxy-a-methyl phenylpropenoic aldehyde, under the action of the catalyst nano white carbon black and under the high temperature condition of preparing the asphalt mixture, the phenylpropenoic aldehyde derivative can rapidly form Schroff alkali substances with amino in the asphalt, and the phenylpropenoic aldehyde derivative and hydrogen sulfide, mercaptan and the like generated in the development process of adding a stabilizer form stable mercaptal, so that harmful gas can not overflow. Meanwhile, the unsaturated bond-containing fatty acid ester group introduced into the molecule can be crosslinked with the asphalt and the modified material, so that the thermal stability and the fluidity of the asphalt modified material are improved.
On one hand, the nano white carbon black adsorbs the phenylpropenoic aldehyde derivative, so that the nano white carbon black is easy to disperse in the asphalt mixture; on the other hand, the pH value of the nano white carbon black is 5-7, the nano white carbon black shows weak acidity, and the nano white carbon black can promote the reaction of the bio-based deodorant and odor substances containing sulfur and the like, and plays a role of a catalyst.
The addition of the antioxidant can prevent and slow down the oxidation of the phenylpropenoic aldehyde derivative serving as an active substance; the addition of the separant can form a protective layer in the asphalt mixing process, so that oxygen is isolated, the active substance phenylpropenoic aldehyde is prevented from being oxidized, and the active substance phenylpropenoic aldehyde derivative has a better effect.
On the basis of the scheme, the HPLC purity of the 3, 4-dilinoleoyloxy-a-methyl phenylpropenoic aldehyde in the second step is 97.3 percent, and the ratio of cis/trans isomers in the product is 4.5/95.5; the peak value of m/z-1 is 701 detected by HPLC-MS.
On the basis of the scheme, the particle size of the nano white carbon black in the third step is 15 nm.
On the basis of the scheme, the antioxidant in the step three is one of antioxidant BHT, antioxidant 1010, antioxidant 1076, antioxidant 168 and antioxidant 264 of Nanjing Pasteur chemical Co. The antioxidant can also be matched with a separant together, so that aldehyde groups in the active substances can be effectively prevented from being oxidized.
On the basis of the scheme, the separant in the third step is one of polyethylene wax, talcum powder, diatomite, oleamide, erucamide and ethylene bis stearamide.
On the basis of the scheme, the viscosity of the polyethylene wax in the step three is 10-20cps, and the penetration degree is less than or equal to 1 mm. Under the performance, a protective layer is easier to form to isolate air and prevent oxidation.
The invention also aims to provide a bio-based deodorant prepared by the preparation method.
The invention also aims to provide application of the bio-based deodorant prepared by the preparation method, wherein the bio-based deodorant is applied to the asphalt mixture, and the addition amount of the bio-based deodorant accounts for 0.03-0.1% of the weight of the asphalt mixture.
On the basis of the scheme, the preparation process of the bio-based deodorant applied to the asphalt mixture is as follows:
adding the prepared bio-based deodorant into the asphalt mixture according to the mass ratio of 0.03-0.1%, then mixing for 15-30min, and transporting to a construction site for paving operation after fully stirring. The technical scheme provided by the invention has the following beneficial effects:
1. in the using process of the asphalt mixture, the final product obtained by synthesis can form Schefflerae alkali substances with amino in the asphalt; and stable mercaptal is formed with hydrogen sulfide, mercaptan and the like generated in the development process of adding the stabilizer, so that the toxic gas overflow is reduced, and the use pollution is reduced.
2. The synthetic raw materials in the synthesis process are all derived from natural substances, such as 3, 4-dihydroxy benzaldehyde extracted from root of Salvia miltiorrhiza Bunge of Labiatae, and linoleic acid extracted from various oil crops. The synthetic method is green, environment-friendly and pollution-free; the synthetic product can be degraded, namely after the pavement reaches the service life, the pavement asphalt can be degraded by bacteria microorganisms under proper conditions after being shoveled and crushed, and no new pollution is generated.
3. The 3, 4-dihydroxy benzaldehyde, n-propionaldehyde and the like in the synthetic raw materials have special plant fragrance, and the discomfort of operators caused by the peculiar smell generated in the mixing process of the asphalt mixture can be relieved.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the contents in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used in the description of the invention herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items. It is to be understood that the various starting materials of the present invention are commercially available, unless otherwise specified.
A method for preparing a bio-based odor eliminating agent, comprising the steps of:
step one, adding a toluene solvent, 1mol of 3, 4-dihydroxy benzaldehyde, 2mol of linoleic acid, 2.2mol of diethyl azodicarboxylate and 2.2mol of triphenylphosphine into a three-neck flask for stirring reaction; after vacuumizing and nitrogen replacement, the three-neck flask is continuously stirred and reacts for 12 hours at 120 ℃; cooling the reactant to 0 ℃ in an ice water bath, and adding ice water for quenching; after the organic phase is subjected to liquid separation, respectively washing, drying, filtering and concentrating to obtain a light yellow crude product; separating and purifying the crude product by column chromatography to obtain a white product 4-formyl-catechol dilinoleate;
dissolving 1.1mol of n-propionaldehyde and 1mol of 4-formyl-catechol dilinoleate prepared in the step one in an ethanol solution under the protection of nitrogen, uniformly stirring, and cooling to-10 ℃; slowly dropwise adding a saturated sodium bicarbonate solution into the reaction system, and reacting for 12 hours at-10 ℃; after detecting that 4-formyl-catechol dilinoleate reacts completely by an HPLC method, adding ice water into reaction liquid, violently stirring, separating out white solid, filtering, and drying at room temperature to obtain 3, 4-dilinoleoyloxy-a-methyl phenylpropyl aldehyde;
and step three, adding 40-60 parts of 3, 4-dioleoyloxy-a-methyl phenylpropenoic aldehyde obtained in the step two, 40-60 parts of nano white carbon black and 0.3-0.5 part of antioxidant into a mixing tank, mixing and stirring for 1h under the test conditions of the temperature of 30 ℃ and the rotation speed of 500rpm, then adding 1-3 parts of separant, and continuing mixing and stirring for 30min to obtain the bio-based deodorant.
Example 1
And in the third step, 40 parts of 3, 4-dilinoleoyloxy-a-methyl phenylpropyl aldehyde, 56.7 parts of nano white carbon black and 10100.3 parts of antioxidant obtained in the second step are added into a mixing tank, mixed and stirred for 1h under the test conditions of the temperature of 30 ℃ and the rotation speed of 500rpm, and then 3.0 parts of polyethylene wax is added and mixed for 30min to obtain the bio-based deodorant.
Example 2
And in the third step, 58 parts of 3, 4-dilinoleoyloxy-a-methyl phenylpropyl aldehyde, 40 parts of nano white carbon black and 0.5 part of antioxidant BHT obtained in the second step are added into a mixing tank, mixed and stirred for 1h under the test conditions of the temperature of 30 ℃ and the rotating speed of 500rpm, then 1.5 parts of erucamide is added, and mixed and stirred for 30min continuously to obtain the bio-based deodorant.
Example 3
And in the third step, 50 parts of 3, 4-dilinoleoyloxy-a-methyl phenylpropyl aldehyde, 48.6 parts of nano white carbon black and 1680.4 parts of antioxidant obtained in the second step are added into a mixing tank, mixed and stirred for 1 hour under the test conditions of the temperature of 30 ℃ and the rotation speed of 500rpm, and then 1.0 part of diatomite is added and mixed for 30 minutes to obtain the bio-based deodorant.
Comparative example 1
Adding 40 parts of benzaldehyde, 56.7 parts of nano white carbon black and 10100.3 parts of antioxidant into a mixing tank, mixing at the temperature of 30 ℃ and the rotating speed of 500rpm for 1h, adding 3.0 parts of polyethylene wax, and continuously mixing for 30min to obtain the bio-based deodorant.
Comparative example 2
A commercial asphalt deodorant is selected, the pH value is neutral, the main component is plant essential oil, and the content of effective substances is 99%.
Experimental results and Performance analysis
The odor removing agents of examples 1 to 3 and comparative examples 1 to 2 were mixed in a mass ratio of bio-based odor removing agent/asphalt mixture of 0.05/100 to obtain mix 1, mix 2, mix 3, mix 4, and mix 5, and then the following test methods and indexes were used to obtain the following experimental results.
The main source of odor in the asphalt construction process is sulfur element contained in substances such as hydrogen sulfide and mercaptan, and as can be seen from table 1, the sulfur content in the gas tested in the mixtures 1-3 is very small, and the effect is better than that of the mixtures 4-5, which shows that the bio-based deodorant provided by the invention can effectively inhibit the overflow and volatilization of odor gas, and the deodorizing effect is obvious, wherein example 2 is the best example. The mixture 1-3 has higher viscosity and good adhesion performance of asphalt and aggregate while having excellent odor removal effect; before and after TFOT or RTFOT of a film oven aging test, the ductility of the mixture 1-3 is higher than that of the mixture 4-5, the elastic restoring force is good, and the anti-rutting performance is good.
While there have been shown and described what are at present considered the fundamental principles and essential features of the invention and its advantages, it will be apparent to those skilled in the art that the invention is not limited to the details of the foregoing exemplary embodiments, but is capable of other specific forms without departing from the spirit or essential characteristics thereof. The present embodiments are therefore to be considered in all respects as illustrative and not restrictive, the scope of the invention being indicated by the appended claims rather than by the foregoing description, and all changes which come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein.
Furthermore, it should be understood that although the present description refers to embodiments, not every embodiment may contain only a single embodiment, and such description is for clarity only, and those skilled in the art should integrate the description, and the embodiments may be combined as appropriate to form other embodiments understood by those skilled in the art.
Claims (8)
1. A method for preparing a bio-based odor eliminating agent, comprising the steps of:
step one, synthesis of 4-formyl-catechol dilinoleate: adding a toluene solvent, 1mol of 3, 4-dihydroxy benzaldehyde, 2mol of linoleic acid, 2.2mol of diethyl azodicarboxylate and 2.2mol of triphenylphosphine into a three-neck flask for stirring reaction; after vacuumizing and nitrogen replacement, the three-neck flask is continuously stirred and reacts for 12 hours at 120 ℃; cooling the reactant to 0 ℃ in an ice water bath, and adding ice water for quenching; after the organic phase is subjected to liquid separation, respectively washing, drying, filtering and concentrating to obtain a light yellow crude product; separating and purifying the crude product by column chromatography to obtain a white product 4-formyl-catechol dilinoleate;
step two, synthesizing 3, 4-dilinoleoyloxy-a-methyl phenylpropenoic aldehyde: under the protection of nitrogen, dissolving 1.1mol of n-propionaldehyde and 1mol of 4-formyl-catechol dilinoleate prepared in the step one in an ethanol solution, uniformly stirring and cooling to-10 ℃; slowly dropwise adding a saturated sodium bicarbonate solution into the reaction system, and reacting for 12 hours at-10 ℃; after detecting that 4-formyl-catechol dilinoleate reacts completely by an HPLC method, adding ice water into reaction liquid, violently stirring, separating out white solid, filtering, and drying at room temperature to obtain 3, 4-dilinoleoyloxy-a-methyl phenylpropyl aldehyde;
adding 40-60 parts of 3, 4-dioleoyloxy-a-methyl phenylpropyl aldehyde, 40-60 parts of nano white carbon black and 0.3-0.5 part of antioxidant obtained in the second step into a mixing tank, mixing and stirring for 1h under the test conditions of the temperature of 30 ℃ and the rotation speed of 500rpm, then adding 1-3 parts of separant, and continuing mixing and stirring for 30min to obtain a bio-based deodorant; the separant is one of polyethylene wax, talcum powder, diatomite, oleamide, erucamide and ethylene bis stearamide.
2. The method of claim 1, wherein the HPLC purity of 3, 4-dioleoyloxy-a-methyl phenylpropenal in step two is 97.3% and the ratio of cis/trans isomers in the product is cis/trans = 4.5/95.5; the peak value of m/z-1 is 701 detected by HPLC-MS.
3. The method for preparing bio-based deodorant according to claim 1, wherein the particle size of the nano white carbon black in step three is 15 nm.
4. The method for preparing a bio-based deodorant according to claim 1, wherein the antioxidant in step three is one of antioxidant BHT, antioxidant 1010, antioxidant 1076, antioxidant 168 and antioxidant 264 of baystading chemical limited, Nanjing.
5. The method for preparing bio-based deodorant according to claim 1, wherein the polyethylene wax viscosity is 10-20cps and the penetration is less than or equal to 1mm in step three.
6. A bio-based deodorant prepared by the method of any one of claims 1 to 5.
7. Use of the bio-based deodorant prepared according to the preparation method of any one of claims 1 to 5, wherein the bio-based deodorant is applied to the asphalt mixture and the addition amount of the bio-based deodorant is 0.03-0.1% by weight of the asphalt mixture.
8. Use of a bio-based odour remover according to claim 7, wherein the preparation process is as follows:
adding the prepared bio-based deodorant into the asphalt mixture according to the mass ratio of 0.03-0.1%, then mixing for 15-30min, and transporting to a construction site for paving operation after fully stirring.
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| WO2003078367A2 (en) * | 2002-03-19 | 2003-09-25 | Ciba Specialty Chemicals Holding Inc. | Benzyl alcohol derivatives and their use as antimicrobial agents |
| DE102007037534A1 (en) * | 2007-08-09 | 2009-02-12 | Air & D - Sarl | Odor reduction process for bitumen |
| CN105238270A (en) * | 2015-09-24 | 2016-01-13 | 天长市金牛防水防腐材料有限公司 | Flame-retardant and smoke-inhibition type non-cured rubber asphalt waterproof coating material |
| CN106723300A (en) * | 2016-12-08 | 2017-05-31 | 深圳市华加生物科技有限公司 | Electronics tobacco tar perfume base and electronics tobacco tar |
| CN108659558B (en) * | 2018-05-30 | 2020-08-04 | 栾海 | Rubber modified asphalt viscosity-reducing deodorant and preparation method and application thereof |
| CN109260927A (en) * | 2018-10-10 | 2019-01-25 | 四川桧元素生物科技有限公司 | A kind of deodorization taste removal concentrate composition of the oil of another name for containing Chinese juniper and preparation method thereof |
| CN109749466B (en) * | 2018-12-28 | 2021-02-23 | 北京东方雨虹防水技术股份有限公司 | Smoke-inhibiting and odor-removing additive, preparation method thereof and modified asphalt |
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