CN111269410A - Decoloring agent and production method of secondary alcohol polyoxyethylene ether using decoloring agent - Google Patents
Decoloring agent and production method of secondary alcohol polyoxyethylene ether using decoloring agent Download PDFInfo
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- CN111269410A CN111269410A CN201811475984.3A CN201811475984A CN111269410A CN 111269410 A CN111269410 A CN 111269410A CN 201811475984 A CN201811475984 A CN 201811475984A CN 111269410 A CN111269410 A CN 111269410A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/30—Post-polymerisation treatment, e.g. recovery, purification, drying
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
- C08G65/2609—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aliphatic hydroxyl groups
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Abstract
The invention relates to a decoloring agent and a production method of secondary alcohol polyoxyethylene ether using the decoloring agent, which mainly solve the problem that the chroma of the secondary alcohol polyoxyethylene ether obtained by the reaction of secondary alcohol and ethylene oxide is high under the condition of an alkaline catalyst in the prior art, and the decoloring agent comprises at least one of the following components (a), (b) and (c): (a) an alkali metal hypophosphite; (b) ethylenediaminetetraacetic acid and/or alkali metal salts thereof; (c) the technical scheme of the aromatic ether better solves the technical problem and can be used for industrial production of secondary alcohol polyoxyethylene ether.
Description
Technical Field
The invention relates to a decoloring agent and a production method of secondary alcohol polyoxyethylene ether using the decoloring agent.
Background
The secondary alcohol polyoxyethylene ether is a product obtained by initiating ethylene oxide polymerization by using a secondary alcohol as an initiator and an alkaline catalyst, and the product has high chroma which not only reflects the color shade of the product, but also directly reflects the inherent quality of the secondary alcohol polyoxyethylene ether. In some applications, the chroma has adverse effect on the use of the secondary alcohol polyoxyethylene ether, and the use performance of the product is finally affected, so that a method for reducing the chroma in the secondary alcohol polyoxyethylene ether is expected.
Disclosure of Invention
One of the technical problems to be solved by the invention is the problem that the secondary alcohol polyoxyethylene ether obtained by the reaction of a secondary alcohol and ethylene oxide has high chroma under the condition of an alkaline catalyst in the prior art, and the invention provides a novel decoloring agent which is used for producing the secondary alcohol polyoxyethylene ether and has the advantage of low chroma of a secondary alcohol polyoxyethylene ether product.
The second technical problem to be solved by the invention is to provide a method for producing secondary alcohol polyoxyethylene ether by using the decoloring agent.
In order to solve one of the above technical problems, the technical solution of the present invention is as follows:
a decoloring agent comprising at least one component selected from the group consisting of the following three components (a), (b) and (c):
(a) an alkali metal hypophosphite;
(b) ethylenediaminetetraacetic acid and/or alkali metal salts thereof;
(c) an aromatic ether.
The use of the decoloring agent can effectively reduce the chroma of the secondary alcohol polyoxyethylene ether.
In the technical scheme, the aromatic ether is preferably diphenyl ether.
In the above technical solution, it is more preferable that the decoloring agent includes at least two of the component (a), the component (b), and the component (c). The two components have an interaction promoting effect on reducing the chroma of the secondary alcohol polyoxyethylene ether. For example, but not limited to, the color destroying agent comprises component (a) and component (b), or the color destroying agent comprises component (a) and component (c), or the color destroying agent comprises component (b) and component (c).
When the decolorizing agent comprises at least two of component (a), component (b) and component (c), the weight ratio between the two is not particularly limited and all achieve comparable mutual promoting technical effects.
By way of non-limiting example, when the decolorizing agent includes component (a), component (b), the weight ratio of component (a) to component (b) can be selected from 0.1 to 10, more specific non-limiting weight ratios such as 0.15, 0.20, 0.25, 0.30, 0.35, 0.40, 0.45, 0.50, 0.55, 0.60, 0.65, 0.70, 0.75, 0.80, 0.85, 0.90, 0.95, 1.0, 1.5, 2.0, 2.5, 3.0, 3.5, 4.0, 4.5, 5.0, 5.5, 6.0, 6.5, 7.0, 7.5, 8.0, 8.5, 9.0, 9.5, and the like.
By way of non-limiting example, when the decolorizing agent includes component (b), component (c), the weight ratio of component (b) to component (c) can be selected from 0.1 to 10, more specific non-limiting weight ratios such as 0.15, 0.20, 0.25, 0.30, 0.35, 0.40, 0.45, 0.50, 0.55, 0.60, 0.65, 0.70, 0.75, 0.80, 0.85, 0.90, 0.95, 1.0, 1.5, 2.0, 2.5, 3.0, 3.5, 4.0, 4.5, 5.0, 5.5, 6.0, 6.5, 7.0, 7.5, 8.0, 8.5, 9.0, 9.5, and the like.
By way of non-limiting example, when the decolorizing agent includes component (a), component (c), the weight ratio of component (a) to component (c) can be selected from 0.1 to 10, more specific non-limiting weight ratios such as 0.15, 0.20, 0.25, 0.30, 0.35, 0.40, 0.45, 0.50, 0.55, 0.60, 0.65, 0.70, 0.75, 0.80, 0.85, 0.90, 0.95, 1.0, 1.5, 2.0, 2.5, 3.0, 3.5, 4.0, 4.5, 5.0, 5.5, 6.0, 6.5, 7.0, 7.5, 8.0, 8.5, 9.0, 9.5, and the like.
In the above technical solution, it is more preferable that the decoloring agent includes a component (a), a component (b), and a component (c), and in this case, the three components have a combined effect in reducing the chromaticity of the secondary alcohol polyoxyethylene ether.
For the technical scheme that the decoloring agent simultaneously comprises the component (a), the component (b) and the component (c), the proportion of the three components is not particularly limited and all can achieve a comparable combined effect.
By way of non-limiting example, when the decolorizing agent includes component (a), component (b), and component (c), component (a): component (b): component (c) can be selected to be 1: x: y, and x and y can be selected independently from 0.1 to 10 by weight, where x and y can be selected independently from a range of values, as further non-limiting examples of points, x and y can be selected independently from 0.15, 0.20, 0.25, 0.30, 0.35, 0.40, 0.45, 0.50, 0.55, 0.60, 0.65, 0.70, 0.75, 0.80, 0.85, 0.90, 0.95, 1.0, 1.5, 2.0, 2.5, 3.0, 3.5, 4.0, 4.5, 5.0, 5.5, 6.0, 6.5, 7.0, 7.5, 8.0, 8.5, 9.5, 9.0, etc.
In the above technical scheme, the alkali metal hypophosphite can be hypophosphorous acidPotassium phosphite and/or sodium hypophosphite; the alkali metal hypophosphite can be anhydrous salt or can contain crystal water, and can achieve comparable technical effects. In the embodiment of the invention, sodium hypophosphite is adopted, and the molecules contain 1 crystal water, namely the molecular formula is NaH2PO2·H2O。
In the above technical scheme, although the component (b) may be ethylenediamine tetraacetic acid, an additional base other than the catalyst amount is required in the reaction to neutralize the ethylenediamine tetraacetic acid into a salt. The alkali metal salt of ethylenediaminetetraacetic acid of component (b) may be a dialkali metal salt of ethylenediaminetetraacetic acid, and/or a tetraalkali metal salt of ethylenediaminetetraacetic acid, with di-salts also requiring the consumption of additional base compared to tetra-salts. The salt may be an anhydrous salt or may contain crystal water. The alkali metal salt of ethylenediaminetetraacetic acid may be a sodium and/or potassium salt of ethylenediaminetetraacetic acid. All of them can achieve comparable technical effects. For comparison, in the embodiment of the present invention, the component (b) is anhydrous ethylenediaminetetraacetic acid tetrasodium salt, which is represented as EDTA-4 Na.
To solve the second technical problem, the technical solution of the present invention is as follows:
the production method of the secondary alcohol polyoxyethylene ether comprises the following steps:
(1) in the presence of an alkaline catalyst, reacting a secondary alcohol with ethylene oxide to obtain high-chroma secondary alcohol polyoxyethylene ether;
(2) and contacting the high-chroma secondary alcohol polyoxyethylene ether with the decoloring agent in any one of the technical schemes for decoloring, adding diatomite for adsorption and filtration to obtain the low-chroma secondary alcohol polyoxyethylene ether.
In the technical scheme, the dosage of the alkaline catalyst in the step (1) is preferably 0.05-1% of the weight of the secondary alcohol polyoxyethylene ether. Such as, but not limited to, 0.06%, 0.07%, 0.08%, 0.09%, 0.10%, 0.15%, 0.20%, 0.25%, 0.30%, 0.35%, 0.40%, 0.45%, 0.50%, 0.55%, 0.60%, 0.65%, 0.70%, 0.75%, 0.80%, 0.85%, 0.90%, 0.95%, and the like.
In the above technical scheme, the temperature of the reaction in step (1) can be selected from 110 to 180 ℃, such as but not limited to 115 ℃, 120 ℃, 125 ℃, 130 ℃, 135 ℃, 140 ℃, 145 ℃, 160 ℃, 165 ℃, 170 ℃, 175 ℃ and the like.
In the technical scheme, the reaction pressure is preferably 0.05-0.5 MPa. Such as, but not limited to, 0.10MPa, 0.15MPa, 0.20MPa, 0.25MPa, 0.30MPa, 0.35MPa, 0.40MPa, 0.45MPa, and the like.
In the technical scheme, the key of the method is the selection of the decolorizing agent, the dosage of the decolorizing agent in the step (2), the treatment temperature and the treatment time are not particularly limited, and the method can obtain comparable technical effects.
As a non-limiting example, the decoloring agent used in step (2) may be 0.05-1% by weight of high chroma secondary alcohol polyoxyethylene ether. Such as, but not limited to, 0.06%, 0.07%, 0.08%, 0.09%, 0.10%, 0.15%, 0.20%, 0.25%, 0.30%, 0.35%, 0.40%, 0.45%, 0.50%, 0.55%, 0.60%, 0.65%, 0.70%, 0.75%, 0.80%, 0.85%, 0.90%, 0.95%, and the like.
As a non-limiting example, the temperature of the step (2) treatment may be 40 to 110 ℃, and further non-limiting temperature values may be 45 ℃, 50 ℃, 55 ℃, 60 ℃, 65 ℃, 70 ℃, 75 ℃, 80 ℃, 85 ℃, 90 ℃, 95 ℃, 100 ℃, 105 ℃, 110 ℃ and the like.
By way of non-limiting example, the time of the treatment of step (2) may be selected from 0.1 to 10 hours, such as but not limited to 0.15 hour, 0.2 hour, 0.25 hour, 0.3 hour, 0.4 hour, 0.5 hour, 0.6 hour, 0.7 hour, 0.8 hour, 0.9 hour, 1.0 hour, 1.5 hour, 2.0 hour, 2.5 hour, 3.0 hour, 3.5 hour, 4.0 hour, 4.5 hour, 5.0 hour, 5.5 hour, 6.0 hour, 6.5 hour, 7.0 hour, 7.5 hour, 8.0 hour, 8.5 hour, 9.0 hour, 9.5 hour, and the like.
In the technical scheme, the secondary alcohol can be C8-C18 secondary alcohol. Such as, but not limited to, C9 secondary alcohol, C10 secondary alcohol, C11 secondary alcohol, C12 secondary alcohol, C13 secondary alcohol, C14 secondary alcohol, C15 secondary alcohol, C16 secondary alcohol, C17 secondary alcohol, and the like.
In the above technical scheme, the addition number of ethylene oxide in the secondary alcohol polyoxyethylene ether is preferably 7-10, for example, but not limited to 7.5, 8, 8.5, 9, 9.5, and the like.
In the technical scheme, the molar ratio of the ethylene oxide to the secondary alcohol is preferably 7-10, such as but not limited to 7.5, 8, 8.5, 9, 9.5, and the like.
In the above technical scheme, the alkali is preferably alkali metal hydroxide and/or alkali metal alkoxide of C1-C2 alcohol.
In the above technical solution, the alkali metal may be K and/or Na.
In the technical scheme, the C1-C2 alcohol can be selected from methanol and/or ethanol.
Unless otherwise specified, the pressures described herein are in terms of gauge pressure.
The chroma analysis method in the specific embodiment of the invention comprises the following steps: GB/T9282.1-2008 transparent liquids rate color on a platinum-cobalt scale.
The inventors have experimentally found that the chroma of the secondary alcohol polyoxyethylene ether can be greatly reduced using the process described herein.
The present invention will be further described with reference to the following examples.
Detailed Description
[ COMPARATIVE EXAMPLE 1 ]
Adding 100g of sec-tridecanol and 1g of potassium hydroxide into a 1-pressure-rising reaction kettle with stirring, sealing the high-pressure reaction kettle, starting stirring, replacing with nitrogen for three times, evacuating and dehydrating at the temperature of 100 ℃ and the pressure of-0.096 MPa for 30 minutes, then introducing ethylene oxide into the reaction kettle, controlling the reaction temperature of 155 ℃ and the reaction pressure of 0.20MPa until the total amount of the introduced ethylene oxide is 198g, stopping introducing the ethylene oxide, then maintaining the reaction temperature until the pressure of the reaction kettle does not drop any more, indicating that the curing reaction is finished, cooling to the temperature of 75 ℃, adding 1g of acetic acid for neutralization, and obtaining the secondary alcohol polyoxyethylene (9) ether. And measuring the chromaticity index.
For comparison, the composition of the decolorizer and the results of the color measurements are shown in Table 1.
[ COMPARATIVE EXAMPLE 2 ]
(1) Adding 100g of sec-tridecanol and 1g of potassium hydroxide into a 1-pressure-rising reaction kettle with stirring, sealing the high-pressure reaction kettle, starting stirring, replacing nitrogen for three times, evacuating and dehydrating at the temperature of 100 ℃ and the pressure of-0.096 MPa for 30 minutes, then introducing ethylene oxide into the reaction kettle, controlling the reaction temperature of 155 ℃ and the reaction pressure of 0.20MPa until the total amount of the introduced ethylene oxide is 198g, stopping introducing the ethylene oxide, then maintaining the reaction temperature until the pressure of the reaction kettle does not drop any more, indicating that the curing reaction is finished, and cooling the temperature to 75 ℃ to obtain secondary alcohol polyoxyethylene (9) ether as an intermediate product.
(2) Stirring at 75 deg.C without decolorizing agent, heat treating for 1 hr, adding 1g of acetic acid, neutralizing at 75 deg.C, adding diatomaceous earth 0.3% of high chroma secondary alcohol polyoxyethylene (9) ether as filter aid, and filtering to obtain final product of secondary alcohol polyoxyethylene (9) ether. And measuring the chromaticity index.
For comparison, the composition of the decolorizer and the results of the color measurements are shown in Table 1.
[ example 1 ]
(1) Adding 100g of sec-tridecanol and 1g of potassium hydroxide into a 1-pressure-rising reaction kettle with stirring, sealing the high-pressure reaction kettle, starting stirring, replacing with nitrogen for three times, evacuating and dehydrating at the temperature of 100 ℃ and the pressure of-0.096 MPa for 30 minutes, introducing ethylene oxide into the reaction kettle, controlling the reaction temperature of 155 ℃ and the reaction pressure of 0.20MPa until the total amount of the introduced ethylene oxide is 198g, stopping introducing the ethylene oxide, maintaining the reaction temperature until the pressure of the reaction kettle does not drop any more, indicating that the curing reaction is finished, and cooling to 75 ℃ to obtain the high-chroma secondary alcohol polyoxyethylene (9) ether.
(2) Adding 1g of sodium hypophosphite, performing heat treatment at 75 ℃ for 1 hour under stirring, adding 1g of acetic acid for neutralization at 75 ℃, adding diatomite accounting for 0.3 percent of the weight of the high-chroma secondary alcohol polyoxyethylene (9) ether as a filter aid, and filtering to obtain a low-chroma secondary alcohol polyoxyethylene (9) ether final product. And measuring the chromaticity index.
For comparison, the composition of the decolorizer and the results of the color measurements are shown in Table 1.
[ example 2 ]
(1) Adding 100g of sec-tridecanol and 1g of potassium hydroxide into a 1-pressure-rising reaction kettle with stirring, sealing the high-pressure reaction kettle, starting stirring, replacing with nitrogen for three times, evacuating and dehydrating at the temperature of 100 ℃ and the pressure of-0.096 MPa for 30 minutes, introducing ethylene oxide into the reaction kettle, controlling the reaction temperature of 155 ℃ and the reaction pressure of 0.20MPa until the total amount of the introduced ethylene oxide is 198g, stopping introducing the ethylene oxide, maintaining the reaction temperature until the pressure of the reaction kettle does not drop any more, indicating that the curing reaction is finished, and cooling to 75 ℃ to obtain the high-chroma secondary alcohol polyoxyethylene (9) ether.
(2) Adding 1g of diphenyl ether, heating at 75 ℃ for 1 hour under stirring, adding 1g of acetic acid for neutralization at 75 ℃, adding diatomite accounting for 0.3 percent of the weight of the high-chroma secondary alcohol polyoxyethylene (9) ether as a filter aid, and filtering to obtain a low-chroma secondary alcohol polyoxyethylene (9) ether final product. And measuring the chromaticity index.
For comparison, the composition of the decolorizer and the results of the color measurements are shown in Table 1.
[ example 3 ]
(1) Adding 100g of sec-tridecanol and 1g of potassium hydroxide into a 1-pressure-rising reaction kettle with stirring, sealing the high-pressure reaction kettle, starting stirring, replacing with nitrogen for three times, evacuating and dehydrating at the temperature of 100 ℃ and the pressure of-0.096 MPa for 30 minutes, introducing ethylene oxide into the reaction kettle, controlling the reaction temperature of 155 ℃ and the reaction pressure of 0.20MPa until the total amount of the introduced ethylene oxide is 198g, stopping introducing the ethylene oxide, maintaining the reaction temperature until the pressure of the reaction kettle does not drop any more, indicating that the curing reaction is finished, and cooling to 75 ℃ to obtain the high-chroma secondary alcohol polyoxyethylene (9) ether.
(2) Adding 1g of EDTA-4Na, carrying out heat treatment at 75 ℃ for 1 hour under stirring, adding 1g of acetic acid for neutralization at 75 ℃, and adding diatomite accounting for 0.3 percent of the weight of the high-chroma secondary alcohol polyoxyethylene (9) ether as a filter aid for filtration to obtain a low-chroma secondary alcohol polyoxyethylene (9) ether final product. And measuring the chromaticity index.
For comparison, the composition of the decolorizer and the results of the color measurements are shown in Table 1.
[ example 4 ]
(1) Adding 100g of sec-tridecanol and 1g of potassium hydroxide into a 1-pressure-rising reaction kettle with stirring, sealing the high-pressure reaction kettle, starting stirring, replacing with nitrogen for three times, evacuating and dehydrating at the temperature of 100 ℃ and the pressure of-0.096 MPa for 30 minutes, introducing ethylene oxide into the reaction kettle, controlling the reaction temperature of 155 ℃ and the reaction pressure of 0.20MPa until the total amount of the introduced ethylene oxide is 198g, stopping introducing the ethylene oxide, maintaining the reaction temperature until the pressure of the reaction kettle does not drop any more, indicating that the curing reaction is finished, and cooling to 75 ℃ to obtain the high-chroma secondary alcohol polyoxyethylene (9) ether.
(2) Adding 0.5g of sodium hypophosphite and 0.5g of EDTA-4Na, performing heat treatment at 75 ℃ for 1 hour under stirring, adding 1g of acetic acid for neutralization at 75 ℃, and adding diatomite accounting for 0.3 percent of the weight of the high-chroma secondary alcohol polyoxyethylene (9) ether as a filter aid for filtration to obtain a low-chroma secondary alcohol polyoxyethylene (9) ether final product. And measuring the chromaticity index.
For comparison, the composition of the decolorizer and the results of the color measurements are shown in Table 1.
[ example 5 ]
(1) Adding 100g of sec-tridecanol and 1g of potassium hydroxide into a 1-pressure-rising reaction kettle with stirring, sealing the high-pressure reaction kettle, starting stirring, replacing with nitrogen for three times, evacuating and dehydrating at the temperature of 100 ℃ and the pressure of-0.096 MPa for 30 minutes, introducing ethylene oxide into the reaction kettle, controlling the reaction temperature of 155 ℃ and the reaction pressure of 0.20MPa until the total amount of the introduced ethylene oxide is 198g, stopping introducing the ethylene oxide, maintaining the reaction temperature until the pressure of the reaction kettle does not drop any more, indicating that the curing reaction is finished, and cooling to 75 ℃ to obtain the high-chroma secondary alcohol polyoxyethylene (9) ether.
(2) Adding 0.5g of sodium hypophosphite and 0.5g of diphenyl ether, performing heat treatment at 75 ℃ for 1 hour under stirring, adding 1g of acetic acid for neutralization at 75 ℃, and adding diatomite accounting for 0.3 percent of the weight of the high-chroma secondary alcohol polyoxyethylene (9) ether as a filter aid for filtration to obtain a low-chroma secondary alcohol polyoxyethylene (9) ether final product. And measuring the chromaticity index.
For comparison, the composition of the decolorizer and the results of the color measurements are shown in Table 1.
[ example 6 ]
(1) Adding 100g of sec-tridecanol and 1g of potassium hydroxide into a 1-pressure-rising reaction kettle with stirring, sealing the high-pressure reaction kettle, starting stirring, replacing with nitrogen for three times, evacuating and dehydrating at the temperature of 100 ℃ and the pressure of-0.096 MPa for 30 minutes, introducing ethylene oxide into the reaction kettle, controlling the reaction temperature of 155 ℃ and the reaction pressure of 0.20MPa until the total amount of the introduced ethylene oxide is 198g, stopping introducing the ethylene oxide, maintaining the reaction temperature until the pressure of the reaction kettle does not drop any more, indicating that the curing reaction is finished, and cooling to 75 ℃ to obtain the high-chroma secondary alcohol polyoxyethylene (9) ether.
(2) Adding 0.5g diphenyl ether and 0.5g EDTA-4Na, heating at 75 deg.C for 1 hr under stirring, adding 1g acetic acid, neutralizing at 75 deg.C, adding diatomite in an amount of 0.3% of the high chroma secondary alcohol polyoxyethylene (9) ether as filter aid, and filtering to obtain the final product. And measuring the chromaticity index.
For comparison, the composition of the decolorizer and the results of the color measurements are shown in Table 1.
[ example 7 ]
(1) Adding 100g of sec-tridecanol and 1g of potassium hydroxide into a 1-pressure-rising reaction kettle with stirring, sealing the high-pressure reaction kettle, starting stirring, replacing with nitrogen for three times, evacuating and dehydrating at the temperature of 100 ℃ and the pressure of-0.096 MPa for 30 minutes, introducing ethylene oxide into the reaction kettle, controlling the reaction temperature of 155 ℃ and the reaction pressure of 0.20MPa until the total amount of the introduced ethylene oxide is 198g, stopping introducing the ethylene oxide, maintaining the reaction temperature until the pressure of the reaction kettle does not drop any more, indicating that the curing reaction is finished, and cooling to 75 ℃ to obtain the high-chroma secondary alcohol polyoxyethylene (9) ether.
(2) Adding 0.8g of sodium hypophosphite, 0.1g of diphenyl ether and 0.1g of EDTA-4Na, performing heat treatment at 75 ℃ for 1 hour under stirring, adding 1g of acetic acid for neutralization at 75 ℃, and adding diatomite accounting for 0.3 percent of the weight of the high-chroma secondary alcohol polyoxyethylene (9) ether as a filter aid for filtration to obtain a low-chroma secondary alcohol polyoxyethylene (9) ether final product. And measuring the chromaticity index.
For comparison, the composition of the decolorizer and the results of the color measurements are shown in Table 1.
[ example 8 ]
(1) Adding 100g of sec-tridecanol and 1g of potassium hydroxide into a 1-pressure-rising reaction kettle with stirring, sealing the high-pressure reaction kettle, starting stirring, replacing with nitrogen for three times, evacuating and dehydrating at the temperature of 100 ℃ and the pressure of-0.096 MPa for 30 minutes, introducing ethylene oxide into the reaction kettle, controlling the reaction temperature of 155 ℃ and the reaction pressure of 0.20MPa until the total amount of the introduced ethylene oxide is 198g, stopping introducing the ethylene oxide, maintaining the reaction temperature until the pressure of the reaction kettle does not drop any more, indicating that the curing reaction is finished, and cooling to 75 ℃ to obtain the high-chroma secondary alcohol polyoxyethylene (9) ether.
(2) Adding 0.1g of sodium hypophosphite, 0.8g of diphenyl ether and 0.1g of EDTA-4Na, performing heat treatment at 75 ℃ for 1 hour under stirring, adding 1g of acetic acid for neutralization at 75 ℃, and adding diatomite accounting for 0.3 percent of the weight of the high-chroma secondary alcohol polyoxyethylene (9) ether as a filter aid for filtration to obtain a low-chroma secondary alcohol polyoxyethylene (9) ether final product. And measuring the chromaticity index.
For comparison, the composition of the decolorizer and the results of the color measurements are shown in Table 1.
[ example 9 ]
(1) Adding 100g of sec-tridecanol and 1g of potassium hydroxide into a 1-pressure-rising reaction kettle with stirring, sealing the high-pressure reaction kettle, starting stirring, replacing with nitrogen for three times, evacuating and dehydrating at the temperature of 100 ℃ and the pressure of-0.096 MPa for 30 minutes, introducing ethylene oxide into the reaction kettle, controlling the reaction temperature of 155 ℃ and the reaction pressure of 0.20MPa until the total amount of the introduced ethylene oxide is 198g, stopping introducing the ethylene oxide, maintaining the reaction temperature until the pressure of the reaction kettle does not drop any more, indicating that the curing reaction is finished, and cooling to 75 ℃ to obtain the high-chroma secondary alcohol polyoxyethylene (9) ether.
(2) Adding 0.1g of sodium hypophosphite, 0.1g of diphenyl ether and 0.8g of EDTA-4Na, performing heat treatment at 75 ℃ for 1 hour under stirring, adding 1g of acetic acid for neutralization at 75 ℃, and adding diatomite accounting for 0.3 percent of the weight of the high-chroma secondary alcohol polyoxyethylene (9) ether as a filter aid for filtration to obtain a low-chroma secondary alcohol polyoxyethylene (9) ether final product. And measuring the chromaticity index.
For comparison, the composition of the decolorizer and the results of the color measurements are shown in Table 1.
[ example 10 ]
(1) Adding 100g of sec-tridecanol and 1g of potassium hydroxide into a 1-pressure-rising reaction kettle with stirring, sealing the high-pressure reaction kettle, starting stirring, replacing with nitrogen for three times, evacuating and dehydrating at the temperature of 100 ℃ and the pressure of-0.096 MPa for 30 minutes, introducing ethylene oxide into the reaction kettle, controlling the reaction temperature of 155 ℃ and the reaction pressure of 0.20MPa until the total amount of the introduced ethylene oxide is 198g, stopping introducing the ethylene oxide, maintaining the reaction temperature until the pressure of the reaction kettle does not drop any more, indicating that the curing reaction is finished, and cooling to 75 ℃ to obtain the high-chroma secondary alcohol polyoxyethylene (9) ether.
(2) Adding 0.3g of sodium hypophosphite, 0.3g of diphenyl ether and 0.4g of EDTA-4Na, performing heat treatment at 75 ℃ for 1 hour under stirring, adding 1g of acetic acid for neutralization at 75 ℃, and adding diatomite accounting for 0.3 percent of the weight of the high-chroma secondary alcohol polyoxyethylene (9) ether as a filter aid for filtration to obtain a low-chroma secondary alcohol polyoxyethylene (9) ether final product. And measuring the chromaticity index.
For comparison, the composition of the decolorizer and the results of the color measurements are shown in Table 1.
[ example 11 ]
(1) Adding 100g of sec-tridecanol and 1g of potassium hydroxide into a 1-pressure-rising reaction kettle with stirring, sealing the high-pressure reaction kettle, starting stirring, replacing with nitrogen for three times, evacuating and dehydrating at the temperature of 100 ℃ and the pressure of-0.096 MPa for 30 minutes, introducing ethylene oxide into the reaction kettle, controlling the reaction temperature of 155 ℃ and the reaction pressure of 0.20MPa until the total amount of the introduced ethylene oxide is 198g, stopping introducing the ethylene oxide, maintaining the reaction temperature until the pressure of the reaction kettle does not drop any more, indicating that the curing reaction is finished, and cooling to 75 ℃ to obtain the high-chroma secondary alcohol polyoxyethylene (9) ether.
(2) Adding 0.4g of sodium hypophosphite, 0.3g of diphenyl ether and 0.3g of EDTA-4Na, performing heat treatment at 75 ℃ for 1 hour under stirring, adding 1g of acetic acid for neutralization at 75 ℃, and adding diatomite accounting for 0.3 percent of the weight of the high-chroma secondary alcohol polyoxyethylene (9) ether as a filter aid for filtration to obtain a low-chroma secondary alcohol polyoxyethylene (9) ether final product. And measuring the chromaticity index.
For comparison, the composition of the decolorizer and the results of the color measurements are shown in Table 1.
[ example 12 ]
(1) Adding 100g of sec-tridecanol and 1g of potassium hydroxide into a 1-pressure-rising reaction kettle with stirring, sealing the high-pressure reaction kettle, starting stirring, replacing with nitrogen for three times, evacuating and dehydrating at the temperature of 100 ℃ and the pressure of-0.096 MPa for 30 minutes, introducing ethylene oxide into the reaction kettle, controlling the reaction temperature of 155 ℃ and the reaction pressure of 0.20MPa until the total amount of the introduced ethylene oxide is 198g, stopping introducing the ethylene oxide, maintaining the reaction temperature until the pressure of the reaction kettle does not drop any more, indicating that the curing reaction is finished, and cooling to 75 ℃ to obtain the high-chroma secondary alcohol polyoxyethylene (9) ether.
(2) Adding 0.3g of sodium hypophosphite, 0.4g of diphenyl ether and 0.3g of EDTA-4Na, performing heat treatment at 75 ℃ for 1 hour under stirring, adding 1g of acetic acid for neutralization at 75 ℃, and adding diatomite accounting for 0.3 percent of the weight of the high-chroma secondary alcohol polyoxyethylene (9) ether as a filter aid for filtration to obtain a low-chroma secondary alcohol polyoxyethylene (9) ether final product. And measuring the chromaticity index.
For comparison, the composition of the decolorizer and the results of the color measurements are shown in Table 1.
TABLE 1
Claims (10)
1. A decoloring agent comprising at least one component selected from the group consisting of the following three components (a), (b) and (c):
(a) an alkali metal hypophosphite;
(b) ethylenediaminetetraacetic acid and/or alkali metal salts thereof;
(c) an aromatic ether.
2. The production method of the secondary alcohol polyoxyethylene ether comprises the following steps:
(1) in the presence of an alkaline catalyst, reacting a secondary alcohol with ethylene oxide to obtain high-chroma secondary alcohol polyoxyethylene ether;
(2) the high-chroma secondary alcohol polyoxyethylene ether is contacted with a decoloring agent for decoloring, and diatomite is added for adsorption and filtration to obtain low-chroma secondary alcohol polyoxyethylene ether;
the decoloring agent comprises at least one of the following components (a), (b) and (c):
(a) an alkali metal hypophosphite;
(b) ethylenediaminetetraacetic acid and/or alkali metal salts thereof;
(c) an aromatic ether.
3. The method according to claim 2, wherein the amount of the basic catalyst used in step (1) is preferably 0.05 to 1% by weight of the secondary alcohol polyoxyethylene ether.
4. The production process according to claim 2, wherein the reaction temperature in the step (1) is 110 to 180 ℃.
5. The production process according to claim 2, wherein the pressure of the reaction in the step (1) is 0.05 to 0.5 MPa.
6. The production method as claimed in claim 2, wherein the decoloring agent in step (2) is used in an amount of 0.05 to 1% by weight based on the high-chroma secondary alcohol polyoxyethylene ether.
7. The method according to claim 2, wherein the temperature of the treatment in the step (2) is 40 to 150 ℃.
8. The method according to claim 2, wherein the treatment time in the step (2) is 0.1 to 10 hours.
9. The method of claim 2, wherein the secondary alcohol is a C8-C18 secondary alcohol.
10. The process according to claim 2, wherein the basic catalyst is an alkali metal hydroxide and/or an alkali metal alkoxide of a C1-C2 alcohol.
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| US4621127A (en) * | 1984-09-18 | 1986-11-04 | Basf Aktiengesellschaft | Preparation of carboxyl-containing polymers |
| CN103467495A (en) * | 2013-09-29 | 2013-12-25 | 天津理工大学 | Method for preparing cefixime compound |
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