CN110665500B - Composite catalyst and preparation method of alcohol ether carboxylate - Google Patents
Composite catalyst and preparation method of alcohol ether carboxylate Download PDFInfo
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- C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
- C07C51/235—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups of —CHO groups or primary alcohol groups
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Abstract
The invention relates to a composite catalyst and a preparation method of alcohol ether carboxylate. The preparation method of the composite catalyst comprises the following steps: (1) pretreatment of activated carbon: reacting activated carbon with an aqueous solution of an activating reagent under a heating condition to obtain pretreated activated carbon; (2) mixing divalent palladium, divalent non-noble metal, hydrochloric acid and the pretreated activated carbon, and reacting; adjusting pH to be alkaline, adding a reducing agent, reacting and separating to obtain a composite catalyst; the activating reagent in the step (1) comprises at least one of hydrochloric acid, nitric acid and hydrogen peroxide; the divalent non-noble metal in the step (2) comprises at least one of divalent nickel, divalent tin and divalent cobalt. The composite catalyst prepared by the method can catalyze alcohol ether to synthesize alcohol ether carboxylate with high conversion rate and high recycling times.
Description
Technical Field
The invention relates to the field of chemical synthesis, in particular to a preparation method of a composite catalyst and alcohol ether carboxylate.
Background
The Alcohol Ether Carboxylate (AEC) is a novel anionic surfactant, has the characteristics of other anionic surfactants, such as low toxicity, easy biodegradation, low surface tension, good compatibility with other surfactants and the like, and is a multifunctional green surfactant. Due to its special properties, fatty alcohol ether carboxylates have found wide application in the fields of cosmetics, detergents, biochemistry, plastics, leather, pharmaceuticals, food processing and the petroleum industry.
The research on AEC in China has been carried out for more than ten years, and the main process routes are two kinds of AEC prepared by reacting sodium chloroacetate with alcohol ether and preparing AEC by catalytically oxidizing alcohol ether by noble metal. The preparation process of the sodium chloroacetate method is a solid-liquid reaction, the viscosity of a material system is high, the process amplification is difficult to a certain degree, the residual chloroacetic acid in the product is difficult to remove, and meanwhile, the chloroacetic acid has toxic action on a human body, so that the alcohol ether carboxylate prepared by the chloroacetic acid method is difficult to enter the daily chemical industry. The alcohol ether carboxylate prepared by the noble metal catalysis method is easy to lose and even inactivate when the catalyst is recycled due to high cost. Therefore, the alcohol ether carboxylic acid prepared by the existing noble metal oxidation method cannot be produced in an industrial large scale.
The general structural formula of the alcohol ether capable of being catalytically oxidized by using a metal oxidation method is as follows: RO (PO) m (EO) n H; wherein R can be alkane or alkene, PO is propylene oxide, m is more than or equal to 0, EO is ethylene oxide, and n is more than 0. The catalytic reaction formula is as follows:
disclosure of Invention
Based on the above, one of the objects of the present invention is to provide a composite catalyst, which can catalyze alcohol ether to synthesize alcohol ether carboxylate with low cost, high conversion rate and high recycling times.
The specific technical scheme is as follows:
a preparation method of the composite catalyst comprises the following steps:
(1) pretreatment of activated carbon: reacting activated carbon with an aqueous solution of an activating reagent under a heating condition to obtain pretreated activated carbon;
(2) mixing divalent palladium, divalent non-noble metal, hydrochloric acid and the obtained pretreated activated carbon, and reacting; adjusting pH to be alkaline, adding a reducing agent, reacting and separating to obtain a composite catalyst;
the activating reagent in the step (1) comprises at least one of hydrochloric acid, nitric acid and hydrogen peroxide;
the divalent non-noble metal in the step (2) comprises at least one of divalent nickel, divalent tin and divalent cobalt.
The invention also aims to provide the composite catalyst prepared by the preparation method.
The invention further aims to provide application of the composite catalyst in preparing alcohol ether carboxylate.
Still another object of the present invention is to provide a method for preparing an alcohol ether carboxylate, comprising the steps of:
(S1) mixing the alcohol ether and the composite catalyst, adjusting the pH to be alkaline by using an aqueous solution of alkali, and reacting;
(S2) the reaction solution is heated by introducing oxygen gas, and the reaction is carried out by solid-liquid separation to adjust the pH of the resulting solution to acidity.
Compared with the prior art, the invention has the following beneficial effects:
the invention firstly carries out pretreatment on the carrier activated carbon by a specific activation step, introduces functional groups on the activated carbon, promotes the dispersion of metals on the carrier and further improves the catalytic activity. In addition, the pretreated activated carbon has a mesoporous characteristic, and abundant gaps further contribute to the dispersion and loading of metal, so that the activity and the metal utilization rate of the catalyst can be further improved, and meanwhile, the stability of the composite catalyst is remarkably improved through the synergistic effect of noble metal palladium and non-noble metal. The composite catalyst prepared by the method can be recycled for a long time and keeps good catalytic activity. After the composite catalyst disclosed by the invention is subjected to catalytic reaction for 1000 hours, the high conversion rate of the alcohol ether can still be realized, and the difference between the yield of the alcohol ether carboxylate and the yield of the alcohol ether carboxylate in the first use is less than or equal to 15%. In addition, the catalytic activity of the composite catalyst is equivalent to that of a pure noble metal catalyst through the synergistic effect of the noble metal palladium and the non-noble metal, so that the cost of the catalyst is greatly reduced, and the large-scale industrial production of the catalyst is favorably realized.
Detailed Description
In order that the invention may be more readily understood, reference will now be made to the following more particular description of the invention, examples of which are set forth below. This invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. These embodiments are provided so that this disclosure will be thorough and complete.
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.
The embodiment provides a preparation method of a composite catalyst, which comprises the following steps:
(1) pretreatment of activated carbon: reacting activated carbon with an aqueous solution of an activating reagent under a heating condition to obtain pretreated activated carbon;
(2) mixing divalent palladium, divalent non-noble metal, hydrochloric acid and the obtained pretreated activated carbon, and reacting; adjusting pH to be alkaline, adding a reducing agent, reacting and separating to obtain a composite catalyst;
the activating reagent in the step (1) comprises at least one of hydrochloric acid, nitric acid and hydrogen peroxide;
the divalent non-noble metal in the step (2) comprises at least one of divalent nickel, divalent tin and divalent cobalt.
Specifically, the preparation method of the composite catalyst comprises the following steps:
(1) pretreatment of activated carbon: reacting activated carbon with an aqueous solution of an activating reagent under a heating condition, filtering, washing filter residues until the pH value is neutral, and drying to obtain pretreated activated carbon;
(2) mixing divalent palladium, divalent non-noble metal and hydrochloric acid, diluting with water, adding the pretreated activated carbon, stirring for reaction, adding an alkali aqueous solution to adjust the pH to be alkaline, adding a sodium borohydride aqueous solution, separating after reaction, and washing until the pH is neutral to obtain the composite catalyst.
In one embodiment, the preprocessing in step (1) comprises: mixing the activated carbon with an aqueous solution of an activating reagent, refluxing for 2-6 h at 70-100 ℃, filtering, washing and drying.
In one embodiment, the mesh number of the activated carbon is 100-300 meshes.
In one embodiment, the mass concentration of the activating reagent in the aqueous solution of the activating reagent in the step (1) is 5-20%. Preferably, the mass concentration of the activating reagent in the aqueous solution of the activating reagent in the step (1) is 8-12%.
In one embodiment, the mass-to-volume ratio of the activated carbon to the aqueous solution of the activating reagent in the step (1) is: (1-10) g (50-200) ml. Preferably, the mass-to-volume ratio of the activated carbon to the aqueous solution of the activating reagent in the step (1) is as follows: (4-6) g, (50-80) ml.
In one embodiment, the mass ratio of the divalent palladium, the divalent non-noble metal and the pretreated activated carbon in the step (2) is as follows: (2-6):(2-6):(45-55).
In one embodiment, in step (2), the adjusting the pH to basic is: adjusting pH to 8-9.
In one embodiment, the reducing agent in step (2) comprises at least one of sodium borohydride, formaldehyde, ethylene glycol, and hydrogen.
This example provides a composite catalyst prepared by the above-mentioned preparation method.
The present example provides the use of the above-described composite catalyst in the preparation of alcohol ether carboxylates.
A method for preparing an alcohol ether carboxylate, comprising the steps of:
(S1) mixing alcohol ether with the composite catalyst obtained by the preparation method, adjusting the pH to be alkaline by using an aqueous solution of alkali, and reacting;
(S2) the reaction solution is heated by introducing oxygen gas, and the reaction is carried out by solid-liquid separation to adjust the pH of the resulting solution to acidity.
In one embodiment, in the step (S1), the mass ratio of the alcohol ether to the composite catalyst is: 100:(1-20).
In one embodiment, in step (S1), the base is sodium hydroxide or potassium hydroxide.
In one embodiment, in step (S1), the pH is adjusted to 10-13; in step (S2), the pH is adjusted to 1-2.
In one embodiment, the alcohol ether is capped with ethylene oxide.
In one embodiment, the alcohol ether has the following general structural formula: RO (PO) m (EO) n H; wherein R is alkyl or alkenyl; PO is epoxypropyl group, m is more than or equal to 0; EO is ethylene oxide, n > 0. The alkyl or alkenyl group contains 1 to 30 carbon atoms.
In one embodiment, the alcohol ether comprises AEO-6, AEO-7, AEO-8, AEO-9, 350, or OE-10.
The present invention will be described in further detail with reference to specific examples.
Example 1
(1) Pretreatment of activated carbon: 5.0g of activated carbon with the particle size of 200 meshes is weighed into a three-necked flask, 60mL of 10% hydrochloric acid aqueous solution is added, and the mixture is stirred and refluxed for 5 hours at 90 ℃. Filtering and washing the activated carbon until the pH value of the filtrate is neutral, and vacuum-drying at 80 ℃ for 12h to obtain the pretreated activated carbon.
(2) Preparation of the composite catalyst: dissolving 32mg of palladium chloride and 41mg of cobalt chloride hexahydrate in 4ml of concentrated hydrochloric acid (37 wt%), diluting with 35ml of water, stirring the solution uniformly, adding 0.5g of pretreated activated carbon, continuing stirring for 3 hours, adding Na 2 CO 3 Adjusting the pH value of the system to 8-9 by using the aqueous solution, continuously stirring for 1h, and adding 200mg of NaBH 4 Dissolved in 2ml of water, added dropwise to the solution, reacted for 3 hours, the solution was centrifuged and washed with water until the pH was neutral.
(3) Preparing alcohol ether carboxylate: 0.25g of the composite catalyst, 2.5g of fatty alcohol-polyoxyethylene ether AEO-9, 0.32g of sodium hydroxide and 40ml of water are added into a three-neck flask. Oxygen was bubbled into the reaction mixture and the reaction was continued with stirring at a constant temperature of 110 ℃ for 8 h. After the reaction, the reaction mixture was centrifuged, the liquid was transferred to a flask, concentrated hydrochloric acid was added to the liquid to adjust the pH to 1, and the product was washed with water to obtain a product. The centrifugally separated catalyst was washed three times with distilled water to remove the residual reactant, dispersed in 20ml of distilled water, and reduced by adding sodium borohydride. The catalyst was washed three times with distilled water and put into next use.
The AEO-9(R-O- (CH) 2 CH 2 O) n H; (R-C12-14, n-9)) is fatty alcohol-polyoxyethylene ether prepared by reacting fatty alcohol with 12-14 carbon atoms with 9 EO. The reaction formula for this example is as follows:
example 2
(1) Pretreatment of activated carbon: 5.0g of activated carbon with the particle size of 200 meshes is weighed into a three-necked bottle, 80mL of aqueous hydrogen peroxide solution with the mass concentration of 8% is added, and the mixture is stirred and refluxed for 5 hours at the temperature of 90 ℃. Filtering and washing the activated carbon until the pH value of the filtrate is neutral, and vacuum-drying at 80 ℃ for 12h to obtain the pretreated activated carbon.
(2) Preparation of the composite catalyst: dissolving 41mg of palladium chloride and 23mg of stannic chloride dihydrate in 4ml of concentrated hydrochloric acid (37 wt%), diluting with 30ml of water, stirring the solution uniformly, adding 0.5g of pretreated activated carbon, continuing stirring for 3 hours, adding Na 2 CO 3 Adjusting pH of the system to 8-9 with water solution, stirring for 1 hr, adding 200mg NaBH 4 Dissolved in 2ml of water, added dropwise to the solution, reacted for 3 hours, the solution was centrifuged and washed with water until the pH was neutral.
(3) Preparing alcohol ether carboxylate: 0.2g of the composite catalyst, 2.5g of fatty alcohol-polyoxyethylene ether AEO-9, 0.32g of sodium hydroxide and 40ml of water are added into a three-neck flask. Oxygen was bubbled into the reaction mixture and the reaction was continued with stirring at a constant temperature of 95 ℃ for 14 h. After the reaction, the reaction mixture was centrifuged, the liquid was transferred to a flask, concentrated hydrochloric acid was added to the liquid to adjust the pH to 1, and the product was washed with water to obtain a product. The centrifugally separated catalyst was washed three times with distilled water to remove the residual reactant, and the catalyst was dispersed in 20ml of distilled water and reduced by adding formaldehyde. The catalyst was washed three times with distilled water and put into next use.
The reaction formula for this example is as follows:
example 3
(1) Pretreatment of activated carbon: weighing 5.0g of active carbon with the particle size of 200 meshes in a three-necked bottle, and respectively adding 80mL of HNO with the mass concentration of 8% 3 The aqueous solution was stirred at 90 ℃ under reflux for 2 h. Filtering and washing the activated carbon until the pH value of the filtrate is neutral, and vacuum-drying at 80 ℃ for 12h to obtain the pretreated activated carbon.
(2) Preparation of the composite catalyst: dissolving 31mg of palladium chloride and 34mg of nickel chloride hexahydrate in 4ml of concentrated hydrochloric acid (37 wt%), diluting with 30ml of water, stirring the solution uniformly, adding 0.5g of pretreated activated carbon, continuing stirring for 3 hours, adding Na 2 CO 3 Adjusting pH of the system to 8-9 with water solution, stirring for 1 hr, adding 200mg NaBH 4 Dissolving in 2ml water, adding dropwise into the solution, reacting for 3 hr, centrifuging the solution, washing with water until pH is neutral
(3) Preparing alcohol ether carboxylate: 0.22g of composite catalyst, 2.5g of fatty alcohol-polyoxyethylene ether AEO-9, 0.32g of sodium hydroxide and 40ml of water are added into a three-neck flask. Oxygen was bubbled into the reaction mixture and the reaction was continued with stirring at 105 ℃ for 15 h. After the reaction, the reaction mixture was centrifuged, the liquid was transferred to a flask, concentrated hydrochloric acid was added to the liquid to adjust the pH to 1, and the product was washed with water to obtain a product. The centrifugally separated catalyst was washed three times with distilled water to remove the residual reactant, dispersed in 20ml of distilled water, and reduced by adding sodium borohydride. The catalyst was washed three times with distilled water and put into next use.
The reaction formula for this example is as follows:
example 4
(1) Pretreatment of activated carbon: weighing 5.0g of active carbon with the particle size of 200 meshes in a three-necked bottle, and respectively adding 80mL of HNO with the mass concentration of 8% 3 The aqueous solution was stirred at 90 ℃ under reflux for 2 h. Filtering and washing the activated carbon until the pH value of the filtrate is neutral, and vacuum-drying at 80 ℃ for 12h to obtain the pretreated activated carbon.
(2) Preparation of the composite catalyst: dissolving 31mg of palladium chloride and 34mg of nickel chloride hexahydrate in 4ml of concentrated hydrochloric acid (37 wt%), diluting with 30ml of water, stirring the solution uniformly, adding 0.5g of pretreated activated carbon, continuing stirring for 3 hours, adding Na 2 CO 3 Adjusting pH of the system to 8-9 with water solution, stirring for 1 hr, adding 200mg NaBH 4 Dissolving in 2ml of water, adding into the solution drop by drop, reacting for 3h,the solution was centrifuged and washed with water until the pH was neutral.
(3) Preparing alcohol ether carboxylate: 0.2g of the composite catalyst, 1.0g of fatty alcohol polyether 350, 0.1g of sodium hydroxide and 40ml of water are added into a three-neck flask. Oxygen was bubbled into the reaction mixture and the reaction was continued with stirring at a constant temperature of 110 ℃ for 24 h. After the reaction, the reaction mixture was centrifuged, the liquid was transferred to a flask, concentrated hydrochloric acid was added to the liquid to adjust the pH to 1, and the product was washed with water to obtain a product. The centrifugally separated catalyst was washed three times with distilled water to remove the residual reactant, and the catalyst was dispersed in 20ml of distilled water and reduced by introducing hydrogen gas. The catalyst was washed three times with distilled water and put into next use.
Wherein 350(R-O- (CH) 2 CH 2 CH 2 O) m (CH 2 CH 2 O) n H; (R-C16-18, m-6, n-4)) is fatty alcohol polyether prepared by reacting alkane with 16-18 carbons with 6 PO and 4 EO. The reaction formula of this example is as follows:
example 5
(1) Pretreatment of activated carbon: 5.0g of active carbon with the particle size of 200 meshes is weighed into a three-necked bottle, 80mL of aqueous hydrogen peroxide solution with the mass concentration of 8% is respectively added, and stirring and refluxing are carried out for 5h at the temperature of 90 ℃. Filtering and washing the activated carbon until the pH value of the filtrate is neutral, and vacuum-drying at 80 ℃ for 12h to obtain the pretreated activated carbon.
(2) Preparation of the composite catalyst: dissolving 38mg of palladium chloride and 25mg of stannic chloride dihydrate in 4ml of concentrated hydrochloric acid (37 wt%), diluting with 30ml of water, stirring the solution uniformly, adding 0.5g of pretreated activated carbon, continuing stirring for 3 hours, adding Na 2 CO 3 Adjusting pH of the system to 8-9 with water solution, stirring for 1 hr, adding 200mg NaBH 4 Dissolved in 2ml of water, added dropwise to the solution, reacted for 3 hours, the solution was centrifuged and washed with water until the pH was neutral.
(3) Preparing alcohol ether carboxylate: 0.2g of the composite catalyst, 3g of fatty alcohol polyether OE-10, 0.35g of sodium hydroxide and 40ml of water are added into a three-neck flask. Oxygen was introduced into the reaction mixture and the reaction was continued with stirring at a constant temperature of 100 ℃ for 8 h. After the reaction, the reaction mixture was centrifuged, the liquid was transferred to a flask, concentrated hydrochloric acid was added to the liquid to adjust the pH to 1, and the product was washed with water to obtain a product. The centrifugally separated catalyst was washed three times with distilled water to remove the residual reactant, dispersed in 20ml of distilled water, and reduced by adding sodium borohydride. The catalyst was washed three times with distilled water and put into next use.
Wherein OE-10 is fatty alcohol polyoxyethylene ether prepared by reacting 16-18 carbon fatty alcohol with a double bond with 10 EO. The reaction formula of this example is as follows:
example 6
This example differs from example 1 in that, in step (1), 10% aqueous hydrogen peroxide was used instead of 10% aqueous hydrochloric acid.
Example 7
This example is different from example 1 in that in step (1), the particle size of activated carbon was 400 mesh.
Example 8
This example differs from example 3 in that in step (1), stirring was carried out at 40 ℃ for 5 h.
Comparative example 1
This comparative example differs from example 1 in that 0.25g of palladium on carbon catalyst (4.9 wt%) was used in place of the composite catalyst.
Comparative example 2
This comparative example differs from example 1 in that 10% sulfuric acid was used instead of 10% hydrochloric acid aqueous solution in step (1).
Comparative example 3
This comparative example differs from example 1 in that, in step (2), an equimolar amount of platinum chloride was used instead of cobalt chloride hexahydrate.
The conversion and catalyst cycle efficiency of the above examples are shown in table 1:
TABLE 1
From the results in table 1, it can be seen that the noble metal palladium, in combination with non-noble metals, cobalt, tin, and nickel, is loaded on the activated carbon after special pretreatment, and has high selectivity when used for catalyzing the oxidation of alcohol ether into alcohol ether carboxylate, and the product can be obtained with high conversion rate. From example 1 and comparative examples 1 and 3, it can be seen that the synergistic effect between the noble metal and the non-noble metal in the composite catalyst of the present invention makes the catalyst less prone to deactivation, can significantly prolong the stability of the catalyst after recycling, and still has a high conversion rate after a long cycle time. Meanwhile, the cost of the non-noble metal catalyst is lower than that of the palladium-carbon catalyst, so that the cost required by the composite catalyst is obviously lower than that of the palladium-carbon catalyst, and the alcohol ether carboxylate can be produced on a large scale.
The technical features of the embodiments described above may be arbitrarily combined, and for the sake of brevity, all possible combinations of the technical features in the embodiments described above are not described, but should be considered as being within the scope of the present specification as long as there is no contradiction between the combinations of the technical features.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (14)
1. The preparation method of the composite catalyst for preparing the alcohol ether carboxylate is characterized by comprising the following steps of:
(1) pretreatment of activated carbon: reacting activated carbon with an aqueous solution of an activating reagent under a heating condition to obtain pretreated activated carbon;
(2) mixing divalent palladium, divalent non-noble metal, hydrochloric acid and the obtained pretreated activated carbon, and reacting; adjusting pH to be alkaline, adding a reducing agent, reacting and separating to obtain a composite catalyst;
the activating reagent in the step (1) is at least one of hydrochloric acid, nitric acid and hydrogen peroxide, and the pretreatment process in the step (1) comprises the following steps: mixing the activated carbon with an aqueous solution of an activating reagent, refluxing for 2-6 h at 90 ℃, filtering, washing and drying;
in the step (2), the divalent non-noble metal is at least one of divalent nickel, divalent tin and divalent cobalt.
2. The method as claimed in claim 1, wherein the mesh size of the activated carbon is 100-300 mesh.
3. The method according to claim 1, wherein the mass concentration of the activating reagent in the aqueous solution of the activating reagent in the step (1) is 5 to 20%.
4. The preparation method according to claim 1, wherein the mass-to-volume ratio of the activated carbon to the aqueous solution of the activating reagent in the step (1) is as follows: (1-10) g, (50-200) ml.
5. The preparation method according to claim 4, wherein the mass volume ratio of the activated carbon to the aqueous solution of the activating reagent in the step (1) is as follows: (4-6) g, (50-80) ml.
6. The preparation method according to claim 1, wherein the mass ratio of the divalent palladium, the divalent non-noble metal and the pretreated activated carbon in the step (2) is as follows: (2-6):(2-6):(45-55).
7. The method according to claim 1, wherein in the step (2), the pH adjustment to alkalinity is: adjusting the pH value to 8-9; and/or, the reducing agent in the step (2) comprises at least one of sodium borohydride, formaldehyde, ethylene glycol and hydrogen.
8. A composite catalyst prepared by the method of any one of claims 1 to 7.
9. The preparation method of the alcohol ether carboxylate is characterized by comprising the following steps:
(S1) mixing the alcohol ether and the composite catalyst of claim 8, adjusting the pH to be alkaline with an aqueous solution of alkali, and reacting;
(S2) the reaction solution is heated by introducing oxygen gas, and the reaction is carried out by solid-liquid separation to adjust the pH of the resulting solution to acidity.
10. The preparation method according to claim 9, wherein in the step (S1), the mass ratio of the alcohol ether to the composite catalyst is: 100:(1-20).
11. The production method according to any one of claims 9 to 10, wherein in the step (S1), the base is sodium hydroxide or potassium hydroxide.
12. The production method according to any one of claims 9 to 10, wherein in the step (S1), the pH is adjusted to 10 to 13; in the step (S2), the pH is adjusted to 1-2.
13. A method of preparation according to any one of claims 9 to 10, characterized in that the alcohol ether is end-capped with ethylene oxide.
14. The method of any one of claims 9-10, wherein the alcohol ether comprises AEO-6, AEO-7, AEO-8, AEO-9, 350 or OE-10.
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| CN101357333A (en) * | 2008-09-20 | 2009-02-04 | 中国日用化学工业研究院 | Pd/C catalyst for preparing alcohol ether carboxylate and production method and use thereof |
| CN109053429A (en) * | 2018-05-31 | 2018-12-21 | 上海发凯化工有限公司 | A kind of preparation method of fatty alcohol ether carboxylic acid |
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