CN102585194A - Method for synthesizing allyl fatty alcohol-polyoxyethylene ether or allyl alkylphenol ethoxylate - Google Patents
Method for synthesizing allyl fatty alcohol-polyoxyethylene ether or allyl alkylphenol ethoxylate Download PDFInfo
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- CN102585194A CN102585194A CN2011104316673A CN201110431667A CN102585194A CN 102585194 A CN102585194 A CN 102585194A CN 2011104316673 A CN2011104316673 A CN 2011104316673A CN 201110431667 A CN201110431667 A CN 201110431667A CN 102585194 A CN102585194 A CN 102585194A
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Abstract
The invention discloses a method for synthesizing allyl fatty alcohol-polyoxyethylene ether or allyl alkylphenol ethoxylate. The method comprises the following steps of: adding fatty alcohol-polyoxyethylene ether or alkylphenol ethoxylate and a solid alkali hydroxide into a stainless steel high pressure reactor, keeping the vacuum degree of the reactor to be 0.085 to 0.1MPa, rising the temperature of the reactor to 70 to 200 DEG C, performing reaction for 1 to 5 hours, stopping a vacuum system, continuing adding allyl halide dropwise into the reactor with continuously stirring, performing reaction under 30 to 100 DEG C and 0.1 to 0.5MPa for 1 to 8 hours, starting the vacuum system to remove residual allyl halide from a product, and discharging a raw product; and adding hot water into the raw product, uniformly mixing the hot water and the raw product, and standing and demixing the mixture to obtain the allyl fatty alcohol-polyoxyethylene ether or the allyl alkylphenol ethoxylate. The method has the advantages of no pollution, low cost and high conversion rate.
Description
Technical field
The present invention relates to the compound method of a kind of allyl group AEO or allyl group TX10.
Background technology
Contain polyoxyethylene groups in allyl group AEO or the allyl group TX10 molecular structure, end group contains two keys, has active chemical property, can be used as tensio-active agent synthetic midbody, like pure ether sulfonate etc.Its synthetic employing Williamson reaction is carried out; AEO or TX10 and alkali metal hydroxide reaction; Generate corresponding alcohol ether salt; In alcohol ether salt, add allyl halide and carry out nucleophilic substitution reaction, generate product allyl group AEO or allyl group TX10 and alkali metal halide.
The preparation method of allyl ethers has following several kinds: (1) AEO or TX10 and hydroxide aqueous solution; Under the condition that phase-transfer catalyst exists, react (US4588534, FR2566401); Preparation aliphatic alcohol polyethenoxy alcohol ether salt or TX10 polyxyethylated alcohol salt add allyl halide after reaction is accomplished and obtain corresponding allyl ethers.(2) AEO or TX10 and solid hydroxide, allyl halide carry out single step reaction and prepare corresponding allyl ethers (EP265856) under the condition that organic solvent exists.Above-mentioned two kinds of methods have added water, phase-transfer catalyst and organic solvent respectively in order to improve reactive behavior in reaction system, in hydroxide aqueous solution, carry out allyl ethers and synthesize, and the water in the system has influenced molecular balance, and transformation efficiency is low; In reaction process, need to add phase-transfer catalyst, phase-transfer catalyst is difficult to from product, separate; Adopted organic solvent,, with an organic solvent must bring environmental problem, in engineering, also need increase units such as solvent removal, increased reaction cost though reaction conversion ratio increases.
Summary of the invention
The purpose of this invention is to provide a kind of pollution-freely, cost is low, a kind of allyl group AEO that transformation efficiency is high or the compound method of allyl group TX10.
The present invention adopts two-step reaction method to carry out the allyl group AEO or the allyl group TX10 is synthetic; At first; AEO or TX10 and solid alkali are under high vacuum condition; Reaction generates aliphatic alcohol polyethenoxy alcohol ether salt or TX10 polyxyethylated alcohol salt, and adopting high vacuum is the moisture that produces in the reaction process in order to remove, and impels molecular balance to carry out to the direction that generates alcohol ether salt.
In the formula: R representes C
8-C
30Straight chained alkyl, branched-chain alkyl or C
8-C
30Phenolic group; N representes oxyethyl group adduction number, 30＞n＞1; M representes a kind of in II family of the I family alkali metal
Aliphatic alcohol polyethenoxy alcohol ether salt or alkylphenol-polyethenoxy alcohol ether salt generate allyl group AEO or allyl group TX10 with the allyl halide reaction again.
In the formula: R representes C
8-C
30Straight chained alkyl, branched-chain alkyl or C
8-C
30Phenolic group; N representes oxyethyl group adduction number, 30＞n＞1; M representes a kind of in II family of the I family alkali metal; Y representes a kind of in the VII family element
Present method has solved the separation problem of transformation efficiency in the allyl ethers building-up process low and phase-transfer catalyst and solvent simultaneously.
Reactions step of the present invention comprises:
(1), the mol ratio by AEO or TX10 and solid alkali is 1: 1-1.5; With AEO or TX10 and solid alkali metal oxyhydroxide adding stainless steel autoclave, the reinforced unlatching simultaneously stirred, and the back that feeds intake is sealed reaction kettle; Air in the nitrogen replacement reaction kettle; Start vacuum system after displacement is accomplished, keeping reaction kettle vacuum tightness is 0.085-0.1MPa, in this process, holds the stirring material that continues; Reaction kettle is warming up to 70-200 ℃, preferred 100-150 ℃; Reaction times 1-5 hour, preferred 2-3 hour, stop heating, be cooled to room temperature, close vacuum system;
(2), the mol ratio by AEO or TX10 and allyl halide is 1: 1-1.5; Continuation drips allyl halide in step (1) reaction kettle; The dropping process continues to stir material, temperature of reaction: 30-100 ℃, preferred 50-80 ℃; Reaction times: 1-8 hour, preferred 2-5 hour; Reaction pressure 0.1-0.5MPa, open vacuum system remove remaining allyl halide in the product, and discharging obtains thick product;
(3), in thick product, add hot water, mix the back standing demix, lower floor is the saturated solution of alkali metal halide, and the upper strata is refined prod allyl group AEO or allyl group TX10.
Aforesaid AEO or TX10 have following general formula (1):
In the formula: R representes C
8-C
30Straight chained alkyl, branched-chain alkyl or C
8-C
30Phenolic group; N representes oxyethyl group adduction number, 30＞n＞1
Aforesaid allyl group AEO or allyl group TX10 have following general formula (2):
In the formula: R representes C
8-C
30Straight chained alkyl, branched-chain alkyl or C
8-C
30Phenolic group; N representes oxyethyl group adduction number, 30＞n＞1.
Aforesaid solid alkali comprises II family of I family alkali metal hydroxide, like sodium hydroxide, Pottasium Hydroxide, Lithium Hydroxide MonoHydrate, Marinco H, calcium hydroxide etc., and preferred sodium hydroxide, Pottasium Hydroxide, Lithium Hydroxide MonoHydrate.That the shape of solid alkali comprises is granular, sheet, bulk, and particle diameter is the solid alkali of 0.01-1mm.
Aforesaid allyl halide is chlorallylene or allyl bromide 98.
Advantage of the present invention is following:
1, the present invention adopts high vacuum to remove the moisture that generates in the reaction process in the first step of reaction, impels sufficient reacting to carry out to the direction that generates midbody aliphatic alcohol polyethenoxy alcohol ether salt or alkylphenol-polyethenoxy alcohol ether salt, has improved reaction conversion ratio.
2, the compound method that the present invention adopted has not with an organic solvent reduced the solvent removal unit, has simplified reaction process.
3, the compound method that the present invention adopted is not used phase-transfer catalyst, has solved the problem of phase-transfer catalyst separation difficulty in the traditional technology.
4, method non-environmental-pollution, the cost that the present invention adopted is low, processing condition are gentle.
Embodiment
The analysis that following embodiment adopts is that the analysis of hydroxyl valency is adopted in AEO or the analysis of TX10 transformation efficiency.
Embodiment 1:
The first step reaction: in 500ml stainless steel autoclave, drop into AEO AEO-7 (molecular weight 501) 200 grams and solid sodium hydroxide 22 grams (particle diameter 1mm), mol ratio is 1: 1, and the reinforced material that carries out simultaneously stirs; After feeding intake reaction kettle is sealed, the air in the nitrogen replacement reaction kettle starts vacuum system after displacement is accomplished; Keeping reaction kettle vacuum tightness is 0.085MPa, in this process, continues to stir material, and reaction kettle is warming up to 200 ℃; React after 5 hours; Stop heating, be cooled to room temperature, close vacuum system;
Second step reaction: in aforesaid reaction vessel, drip chlorallylene 39 grams; The mol ratio of AEO or TX10 and chlorallylene is 1: 1, continue to stir material in the dropping process, drips end of a period exothermic heat of reaction to 30 ℃; Reaction kettle pressure 0.1MPa; Stir stopped reaction after 1 hour, remaining chlorallylene in the product, discharging are removed by the open vacuum system.
Aftertreatment: in product, add 70 gram hot water, mix the back standing demix, lower floor is the saturated solution of sodium-chlor, and the upper strata is refined prod allyl group AEO or allyl group TX10.Conversion rate of products is 82%.
Embodiment 2:
The first step reaction: in 500ml stainless steel autoclave, drop into TX10 NP-8 (molecular weight 520) 200 grams and solid hydrogen Lithium Oxide 98min 12 grams (particle diameter 0.1mm), mol ratio is 1: 1.3, and the reinforced material that carries out simultaneously stirs; After feeding intake reaction kettle is sealed, the air in the nitrogen replacement reaction kettle starts vacuum system after displacement is accomplished; Keeping reaction kettle vacuum tightness is 0.1MPa, in this process, continues to stir material, and reaction kettle is warming up to 140 ℃; React after 3 hours; Stop heating, be cooled to room temperature, close vacuum system;
Second step reaction: in aforesaid reaction vessel, drip allyl bromide 98 60 grams; The mol ratio of AEO or TX10 and allyl bromide 98 is 1: 1.3, continue to stir material in the dropping process, drips end of a period exothermic heat of reaction to 60 ℃; Reaction kettle pressure 0.2MPa; Stir stopped reaction after 3 hours, remaining allyl bromide 98 in the product, discharging are removed by the open vacuum system.
Aftertreatment: in product, add 40 gram hot water, mix the back standing demix, lower floor is the saturated solution of lithiumbromide, and the upper strata is refined prod allyl group AEO or allyl group TX10.Conversion rate of products is 93%.
Embodiment 3:
The first step reaction: in 500ml stainless steel autoclave, drop into TX10 TX-10 (molecular weight 601) 200 grams and solid potassium hydroxide 28 grams (particle diameter 0.01mm), mol ratio is 1: 1.5, and the reinforced material that carries out simultaneously stirs; After feeding intake reaction kettle is sealed, the air in the nitrogen replacement reaction kettle starts vacuum system after displacement is accomplished; Keeping reaction kettle vacuum tightness is 0.1MPa, in this process, continues to stir material, and reaction kettle is warming up to 70 ℃; React after 1 hour; Stop heating, be cooled to room temperature, close vacuum system;
Second step reaction: in aforesaid reaction vessel, drip chlorallylene 38 grams; AEO or TX10 and chlorallylene mol ratio are 1: 1.5, continue to stir material in the dropping process, drip end of a period exothermic heat of reaction to 100 ℃; Reaction kettle pressure 0.5MPa; Stir stopped reaction after 5 hours, remaining chlorallylene in the product, discharging are removed by the open vacuum system.
Aftertreatment: in product, add 80 gram hot water, mix the back standing demix, lower floor is the saturated solution of Repone K, and the upper strata is refined prod allyl group AEO or allyl group TX10.Conversion rate of products is 94%.
Embodiment 4:
The first step reaction: in 500ml stainless steel autoclave, drop into TX10 AEO-9 (molecular weight 590) 200 grams and solid hydrogen Natural manganese dioxide 8 grams (particle diameter 0.3mm), mol ratio is 1: 1.2, and the reinforced material that carries out simultaneously stirs; After feeding intake reaction kettle is sealed, the air in the nitrogen replacement reaction kettle starts vacuum system after displacement is accomplished; Keeping reaction kettle vacuum tightness is 0.1MPa, in this process, continues to stir material, and reaction kettle is warming up to 100 ℃; React after 2 hours; Stop heating, be cooled to room temperature, close vacuum system;
Second step reaction: in aforesaid reaction vessel, drip allyl bromide 98 49 grams; AEO or TX10 and allyl halide mol ratio are 1: 1.2, continue to stir material in the dropping process, drip end of a period exothermic heat of reaction to 70 ℃; Reaction kettle pressure 0.2MPa; Stir stopped reaction after 2 hours, remaining allyl bromide 98 in the product, discharging are removed by the open vacuum system.
Aftertreatment: in product, add 70 gram hot water, mix the back standing demix, lower floor is the saturated solution of magnesium bromide, and the upper strata is refined prod allyl group AEO or allyl group TX10.Conversion rate of products is 91%.
Embodiment 5:
The first step reaction: in 500ml stainless steel autoclave, drop into TX10 NP-30 (molecular weight 1480) 200 grams and solid hydrogen quicklime 5 grams (particle diameter 0.05mm), mol ratio is 1: 1.3, and the reinforced material that carries out simultaneously stirs; After feeding intake reaction kettle is sealed, the air in the nitrogen replacement reaction kettle starts vacuum system after displacement is accomplished; Keeping reaction kettle vacuum tightness is 0.1MPa, in this process, continues to stir material, and reaction kettle is warming up to 160 ℃; React after 4 hours; Stop heating, be cooled to room temperature, close vacuum system;
Second step reaction: in aforesaid reaction vessel, drip chlorallylene 14 grams; AEO or TX10 and chlorallylene mol ratio are 1: 1.3, continue to stir material in the dropping process, drip end of a period exothermic heat of reaction to 60 ℃; Reaction kettle pressure 0.2MPa; Stir stopped reaction after 4 hours, remaining chlorallylene in the product, discharging are removed by the open vacuum system.
Aftertreatment: in product, add 40 gram hot water, mix the back standing demix, lower floor is the saturated solution of calcium chloride, and the upper strata is refined prod allyl group AEO or allyl group TX10.Conversion rate of products is 90%.
Embodiment 6:
The first step reaction: in 500ml stainless steel autoclave, drop into TX10 AEO-3 (molecular weight 325) 200 grams and solid sodium hydroxide 27 grams (particle diameter 0.8mm), mol ratio is 1: 1.1, and the reinforced material that carries out simultaneously stirs; After feeding intake reaction kettle is sealed, the air in the nitrogen replacement reaction kettle starts vacuum system after displacement is accomplished; Keeping reaction kettle vacuum tightness is 0.1MPa, in this process, continues to stir material, and reaction kettle is warming up to 90 ℃; React after 1 hour; Stop heating, be cooled to room temperature, close vacuum system;
Second step reaction: in aforesaid reaction vessel, drip chlorallylene 52 grams; AEO or TX10 and allyl halide mol ratio are 1: 1.1, continue to stir material in the dropping process, drip end of a period exothermic heat of reaction to 50 ℃; Reaction kettle pressure 0.2MPa; Stir stopped reaction after 5 hours, remaining chlorallylene in the product, discharging are removed by the open vacuum system.
Aftertreatment: in product, add 60 gram hot water, mix the back standing demix, lower floor is the saturated solution of sodium-chlor, and the upper strata is refined prod allyl group AEO or allyl group TX10.Conversion rate of products is 89%.
Claims (11)
1. the compound method of allyl group AEO or allyl group TX10 is characterized in that comprising the steps:
(1), be 1 by the mol ratio of AEO or TX10 and solid alkali: 1-1.5, AEO or TX10 and solid alkali metal oxyhydroxide are added the stainless steel autoclave, the reinforced unlatching simultaneously stirred; After feeding intake reaction kettle is sealed, the air in the nitrogen replacement reaction kettle starts vacuum system after displacement is accomplished; Keeping reaction kettle vacuum tightness is 0.085-0.1MPa, in this process, holds the stirring material that continues, and reaction kettle is warming up to 70-200 ℃; Reaction times 1-5 hour,, stop heating; Be cooled to room temperature, close vacuum system;
(2), be 1 by the mol ratio of AEO or TX10 and allyl halide: 1-1.5, continue in step (1) reaction kettle, to drip allyl halide, the dropping process continues to stir material; Temperature of reaction: 30-100 ℃; Reaction times: 1-8 hour, reaction pressure 0.1-0.5MPa, remaining allyl halide in the product is removed by the open vacuum system; Discharging obtains thick product;
(3), in thick product, add hot water, mix the back standing demix, lower floor is the saturated solution of alkali metal halide, and the upper strata is refined prod allyl group AEO or allyl group TX10.
2. the compound method of a kind of allyl group AEO as claimed in claim 1 or allyl group TX10 is characterized in that described AEO or TX10 have following general formula:
In the formula: R representes C
8-C
30Straight chained alkyl, branched-chain alkyl or C
8-C
30Phenolic group; N representes oxyethyl group adduction number, 30＞n＞1
3. the compound method of a kind of allyl group AEO as claimed in claim 1 or allyl group TX10 is characterized in that described solid alkali is I family or II family alkali metal hydroxide.
4. the compound method of a kind of allyl group AEO as claimed in claim 2 or allyl group TX10 is characterized in that described I family alkali metal hydroxide is sodium hydroxide, Pottasium Hydroxide or Lithium Hydroxide MonoHydrate.
5. the compound method of a kind of allyl group AEO as claimed in claim 4 or allyl group TX10 is characterized in that described II family alkali metal hydroxide is Marinco H or calcium hydroxide.
6. the compound method of a kind of allyl group AEO as claimed in claim 4 or allyl group TX10 is characterized in that described I family or II family alkali metal hydroxide are sodium hydroxide, Pottasium Hydroxide or Lithium Hydroxide MonoHydrate.
7. the compound method of a kind of allyl group AEO as claimed in claim 1 or allyl group TX10 is characterized in that being shaped as of described solid alkali is granular, sheet or bulk, and particle diameter is the solid alkali of 0.01-1mm.
8. the compound method of a kind of allyl group AEO as claimed in claim 1 or allyl group TX10 is characterized in that described allyl halide is chlorallylene or allyl bromide 98.
9. the compound method of a kind of allyl group AEO as claimed in claim 1 or allyl group TX10 is characterized in that reaction kettle is warming up to 100-150 ℃ in the described step (1); Reaction times 2-3 hour.
10. the compound method of a kind of allyl group AEO as claimed in claim 1 or allyl group TX10 is characterized in that described step (2) temperature of reaction is 50-80 ℃; Reaction times is 2-5 hour.
11. the compound method of a kind of allyl group AEO as claimed in claim 1 or allyl group TX10 is characterized in that described allyl group AEO or allyl group TX10 have following general formula:
In the formula: R representes C
8-C
30Straight chained alkyl, branched-chain alkyl or C
8-C
30Phenolic group; N representes oxyethyl group adduction number, 30＞n＞1.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103980437A (en) * | 2014-05-28 | 2014-08-13 | 中国日用化学工业研究院 | Polycarboxylic acid water reducing agent and preparation method thereof |
| CN104448284A (en) * | 2014-11-28 | 2015-03-25 | 浙江皇马科技股份有限公司 | Preparation method of diallyl-capped polyether |
| CN113956465A (en) * | 2021-10-22 | 2022-01-21 | 南京清研新材料研究院有限公司 | End capping method of allyl polyether |
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| CN103980437A (en) * | 2014-05-28 | 2014-08-13 | 中国日用化学工业研究院 | Polycarboxylic acid water reducing agent and preparation method thereof |
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| CN104448284A (en) * | 2014-11-28 | 2015-03-25 | 浙江皇马科技股份有限公司 | Preparation method of diallyl-capped polyether |
| CN113956465A (en) * | 2021-10-22 | 2022-01-21 | 南京清研新材料研究院有限公司 | End capping method of allyl polyether |
| CN113956465B (en) * | 2021-10-22 | 2024-04-09 | 南京清奇新材料科技有限公司 | End capping method of allyl polyether |
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Application publication date: 20120718 |