CN102786679B - Preparation method for polyoxyethylene mono-caprylic-capric acid glyceride - Google Patents
Preparation method for polyoxyethylene mono-caprylic-capric acid glyceride Download PDFInfo
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- CN102786679B CN102786679B CN201210283149.6A CN201210283149A CN102786679B CN 102786679 B CN102786679 B CN 102786679B CN 201210283149 A CN201210283149 A CN 201210283149A CN 102786679 B CN102786679 B CN 102786679B
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Abstract
The invention discloses a preparation method for polyoxyethylene mono-caprylic-capric acid glyceride. The preparation method comprises the following steps of: 1) esterification reaction: glycerol and caprylic-capric acid are taken as raw materials, a solid catalyst is added, water is separated from the mixture under nitrogen flow, a temperature is increased to 150 DEG C to 180 DEG C, heat is preserved for 3-6 hours, and the temperature is decreased at 50 DEG C to 70 DEG C; 2) purification of mono-caprylic-capric acid ester; and 3) condensation reaction of ethylene oxide: mono-caprylic-capric acid ester after purification is taken as the raw material, an alkaline catalyst is added, nitrogen is substituted, the temperature is increased to 100 DEG C to 120 DEG C, after 20-40 minutes, ethylene oxide is slowly led into for 3-5 hours, after the addition is finished, processes of aging, pressure reduction, temperature lowering and degassing are carried out, and the product is obtained after the discharging. The preparation method has the characteristics of reasonable process, high product purity and good use performance.
Description
Technical field
The present invention relates to a kind of preparation method of polyoxyethylene list Glycerin, mixed triester with caprylic acid capric acid, belong to the synthesis technical field of nonionogenic tenside in organic chemistry.
Background technology
Polyoxyethylene list Glycerin, mixed triester with caprylic acid capric acid belongs to polyol-based non-ionic surfactant, is a kind of high-quality and efficient emulsifying agent, has good emulsification, dispersion and stabilization.Glycerine has good softness, emulsification, lubricated, anti-fog, antistatic and add dissolubility, and toxicity is low, little to skin irritation, and easily the characteristic such as degraded, has been widely used at food, medicine, makeup and metal processing and other fields tool.Particularly this product is a kind of food emulsifier of colourless (or micro-yellow) tasteless high-hydrophilic, its existing good hydrophilic and oleophilic performance, has acid-fast ability again, and along with the raising of oxyethane, HLB value can reach higher level.Due to its middle carbon structure, more can embody consistency and the emulsifying stability of this product and other products, so the application of this product must be up-and-coming, have been widely used at food, medicine, makeup and metal processing and other fields tool.This product can replace tween series product in food-processing, is a kind of New-type emulsifier.The condensation number of oxyethane can not be greater than 20, and too high words lipophilicity can not embody.
Have report alkali to do the crude product of the pungent decylate of Catalyst Production glycerine list, it is very dark that alkali does the esterified prod color of Catalyst Production; With the pungent decylate of Methods For Purification glycerine list of solvent recrystallization, technique is pretty troublesome, and environmental pollution is large.
The content of invention
The preparation method who the object of the present invention is to provide a kind of polyoxyethylene list Glycerin, mixed triester with caprylic acid capric acid, technique is reasonable, and product purity is high, has the feature of better use properties.
For achieving the above object, technical scheme of the present invention is:
A preparation method for polyoxyethylene list Glycerin, mixed triester with caprylic acid capric acid, comprises the steps: 1) esterification: taking glycerine and pungent capric acid as raw material, add solid catalyst, under the condition of nitrogen gas stream, separate the water that esterification generates, be warming up to 150 DEG C-180 DEG C, insulation 3-6h, is down to 50-70 DEG C; 2) the single pungent decylate of purification; 3) ethylene oxide condensation reaction: the single Glycerin, mixed triester with caprylic acid capric acid obtaining to purify is raw material, adds basic catalyst, nitrogen replacement, be warmed up to 100 DEG C-120 DEG C, after 20-40min, slowly pass into oxyethane 3-5h, add slaking, the step-down degassed discharging of lowering the temperature, obtains product.
The weight ratio of described glycerine and pungent capric acid is 1:1.60-1.85.
Solid catalyst add-on in described esterification is the 0.01%-0.08% of glycerine and pungent capric acid gross weight.
Described solid catalyst adopts the one in tin protochloride, tin protoxide.
The described pungent decylate of purification list is to use rotary scraper film evaporator, and the collection temperature of single Glycerin, mixed triester with caprylic acid capric acid is 130-140 DEG C, and pressure is 8-12Pa.
The weight ratio of the pungent decylate of described glycerine list and oxyethane is 1:1-3.0; Basic catalyst in described ethylene oxide condensation reaction is the 0.1%-0.5% of single pungent decylate and oxyethane gross weight.
Basic catalyst in described ethylene oxide condensation reaction is the one adopting in potassium hydroxide, sodium hydroxide.
The invention has the beneficial effects as follows: the preparation method of a kind of polyoxyethylene list Glycerin, mixed triester with caprylic acid capric acid that the application of the invention obtains has the following advantages: 1, adopt the esterification under solid catalyst effect, conversion unit is simple.2, the present invention adopts rotary scraper film evaporator to obtain than other separation methods the product that purity is higher, easy to operate.3, the polyoxyethylene list Glycerin, mixed triester with caprylic acid capric acid being made by the present invention, has hydrophilic and oleophilic base, has excellent emulsifying property, has good consistency and emulsifying stability with other products.4, the present invention does not almost pollute environment.
Embodiment
Embodiment 1
1) esterification: add by weight 644 grams of glycerine in the flask of 2L, 1036 grams of pungent capric acid, under stirring, add 0.336 gram of solid catalyst tin protochloride, slowly heat up, under the condition of nitrogen gas stream, separate in time the water that esterification generates, be warming up under the reaction conditions of 180 DEG C, be incubated 3.0 hours, after be cooled to 60 DEG C, blowing, acid transformation efficiency be 99.9%.
2) the single pungent decylate of purification: with rotary scraper film evaporator, collecting temperature is 130 DEG C, 700 grams of single Glycerin, mixed triester with caprylic acid capric acid in left and right of lighting end of pressure 8Pa, another cut is two Glycerin, mixed triester with caprylic acid capric acid by products.
3) ethylene oxide condensation reaction: add 400 grams of single Glycerin, mixed triester with caprylic acid capric acid in the addition still of 2L, stirring adds 7.6 grams, potassium hydroxide, nitrogen replacement heats up for three times afterwards, and temperature to 100 DEG C, after dehydration 30min, temperature is transferred to 100 DEG C and is slowly passed into 1153 grams, oxyethane, 5 hours time, adds slaking, and equipressure drops to only can not be reduced to, the degassed discharging of lowering the temperature, obtains 1555 grams of product polyoxyethylene list Glycerin, mixed triester with caprylic acid capric acid.
The preparation method of a kind of polyoxyethylene list Glycerin, mixed triester with caprylic acid capric acid obtaining by use the present embodiment has the following advantages: 1, adopt the esterification under solid catalyst effect, conversion unit is simple.2, the present embodiment adopts rotary scraper film evaporator to obtain than other separation methods the product that purity is higher, easy to operate.3, the polyoxyethylene list Glycerin, mixed triester with caprylic acid capric acid being made by the present embodiment, has hydrophilic and oleophilic base, has excellent emulsifying property, has good consistency and emulsifying stability with other products.4, the present embodiment does not almost pollute environment.
Embodiment 2
1) esterification: add by weight 644 grams of glycerine in the flask of 2L, 1085 grams of pungent capric acid, under stirring, add 0.5187 gram of solid catalyst tin protoxide, slowly heat up, under the condition of nitrogen gas stream, separate in time the water that esterification generates, be warming up under the reaction conditions of 150 DEG C, be incubated 6.0 hours, after be cooled to 50 DEG C, blowing, acid transformation efficiency be 99.8%.
2) the single pungent decylate of purification: with rotary scraper film evaporator, collecting temperature is 140 DEG C, 750 grams of single Glycerin, mixed triester with caprylic acid capric acid in left and right of lighting end of pressure 10Pa, another cut is two Glycerin, mixed triester with caprylic acid capric acid by products.
3) ethylene oxide condensation reaction: add 400 grams of single Glycerin, mixed triester with caprylic acid capric acid in the addition still of 2L, stirring adds 3.6 grams, sodium hydroxide, nitrogen replacement heats up for three times afterwards, and temperature to 120 DEG C, after dehydration 40min, temperature is transferred to 120 DEG C and is slowly passed into 776 grams, oxyethane, 4.5 hours time, adds slaking, and equipressure drops to only can not be reduced to, the degassed discharging of lowering the temperature, obtains 1175 grams of product polyoxyethylene list Glycerin, mixed triester with caprylic acid capric acid.
The preparation method of a kind of polyoxyethylene list Glycerin, mixed triester with caprylic acid capric acid obtaining by use the present embodiment has the following advantages: 1, adopt the esterification under solid catalyst effect, conversion unit is simple.2, the present embodiment adopts rotary scraper film evaporator to obtain than other separation methods the product that purity is higher, easy to operate.3, the polyoxyethylene list Glycerin, mixed triester with caprylic acid capric acid being made by the present embodiment, has hydrophilic and oleophilic base, has excellent emulsifying property, has good consistency and emulsifying stability with other products.4, the present embodiment does not almost pollute environment.
Embodiment 3
1) esterification: add by weight 644 grams of glycerine in the flask of 2L, 1141 grams of pungent capric acid, under stirring, add 0.7140 gram of solid catalyst tin protochloride, slowly heat up, under the condition of nitrogen gas stream, separate in time the water that esterification generates, be warming up under the reaction conditions of 160 DEG C, be incubated 5.0 hours, after be cooled to 70 DEG C, blowing, acid transformation efficiency be 99.99%.
2) the single pungent decylate of purification: with rotary scraper film evaporator, collecting temperature is 135 DEG C, 790 grams of single Glycerin, mixed triester with caprylic acid capric acid in left and right of lighting end of pressure 12Pa, another cut is two Glycerin, mixed triester with caprylic acid capric acid by products.
3) ethylene oxide condensation reaction: add 400 grams of single Glycerin, mixed triester with caprylic acid capric acid in the addition still of 2L, stirring adds 2.4 grams, sodium hydroxide, nitrogen replacement heats up for three times afterwards, and temperature to 110 DEG C, after dehydration 20min, temperature is transferred to 110 DEG C and is slowly passed into 400 grams, oxyethane, 3 hours time, adds slaking, and equipressure drops to only can not be reduced to, the degassed discharging of lowering the temperature, obtains 795 grams of product polyoxyethylene list Glycerin, mixed triester with caprylic acid capric acid.
The preparation method of a kind of polyoxyethylene list Glycerin, mixed triester with caprylic acid capric acid obtaining by use the present embodiment has the following advantages: 1, adopt the esterification under solid catalyst effect, conversion unit is simple.2, the present embodiment adopts rotary scraper film evaporator to obtain than other separation methods the product that purity is higher, easy to operate.3, the polyoxyethylene list Glycerin, mixed triester with caprylic acid capric acid being made by the present embodiment, has hydrophilic and oleophilic base, has excellent emulsifying property, has good consistency and emulsifying stability with other products.4, the present embodiment does not almost pollute environment.
Embodiment 4
1) esterification: add by weight 644 grams of glycerine in the flask of 2L, 1190 grams of pungent capric acid, under stirring, add 0.9170 gram of solid catalyst tin protoxide, slowly heat up, under the condition of nitrogen gas stream, separate in time the water that esterification generates, be warming up under the reaction conditions of 170 DEG C, be incubated 4.0 hours, after be cooled to 60 DEG C, blowing, acid transformation efficiency be 99.8%.
2) the single pungent decylate of purification: with rotary scraper film evaporator, collecting temperature is 130 DEG C, 780 grams of single Glycerin, mixed triester with caprylic acid capric acid in left and right of lighting end of pressure 10Pa, another cut is two Glycerin, mixed triester with caprylic acid capric acid by products.
3) ethylene oxide condensation reaction: add 400 grams of single Glycerin, mixed triester with caprylic acid capric acid in the addition still of 2L, stirring adds 3.1 grams, potassium hydroxide, nitrogen replacement heats up for three times afterwards, and temperature to 100 DEG C, after dehydration 30min, temperature is transferred to 100 DEG C and is slowly passed into 620 grams, oxyethane, 4 hours time, adds slaking, and equipressure drops to only can not be reduced to, the degassed discharging of lowering the temperature, obtains 1015 grams of product polyoxyethylene list Glycerin, mixed triester with caprylic acid capric acid.
The preparation method of a kind of polyoxyethylene list Glycerin, mixed triester with caprylic acid capric acid obtaining by use the present embodiment has the following advantages: 1, adopt the esterification under solid catalyst effect, conversion unit is simple.2, the present embodiment adopts rotary scraper film evaporator to obtain than other separation methods the product that purity is higher, easy to operate.3, the polyoxyethylene list Glycerin, mixed triester with caprylic acid capric acid being made by the present embodiment, has hydrophilic and oleophilic base, has excellent emulsifying property, has good consistency and emulsifying stability with other products.4, the present embodiment does not almost pollute environment.
In above-described embodiment, its esterification equation is:
R is:
(CH
2)
6cH
3or (CH
2)
8cH
3
In above-described embodiment, its ethylene oxide condensation reaction equation is:
R is:
(CH
2)
6cH
3or (CH
2)
8cH
3m+n=5～15.
Claims (5)
1. the preparation method of a polyoxyethylene list Glycerin, mixed triester with caprylic acid capric acid, it is characterized in that comprising the steps: 1) esterification: taking glycerine and pungent capric acid as raw material, add solid catalyst, under the condition of nitrogen gas stream, separate the water that esterification generates, be warming up to 150 DEG C-180 DEG C, insulation 3-6h, is down to 50-70 DEG C; 2) the single pungent decylate of purification; 3) ethylene oxide condensation reaction: the single Glycerin, mixed triester with caprylic acid capric acid obtaining to purify is raw material, adds basic catalyst, and nitrogen replacement is warmed up to 100 DEG C-120 DEG C, after 20-40min, slowly pass into oxyethane 3-5h, add slaking, step-down, the degassed discharging of lowering the temperature, obtain product
Wherein, described solid catalyst adopts the one in tin protochloride, tin protoxide, and the described pungent decylate of purification list is to use rotary scraper film evaporator, and the collection temperature of single Glycerin, mixed triester with caprylic acid capric acid is 130-140 DEG C, and pressure is 8-12Pa.
2. the preparation method of a kind of polyoxyethylene list Glycerin, mixed triester with caprylic acid capric acid according to claim 1, is characterized in that: the weight ratio of described glycerine and pungent capric acid is 1:1.60-1.85.
3. the preparation method of a kind of polyoxyethylene list Glycerin, mixed triester with caprylic acid capric acid according to claim 1, is characterized in that: the solid catalyst add-on in described esterification is the 0.01%-0.08% of glycerine and pungent capric acid gross weight.
4. the preparation method of a kind of polyoxyethylene list Glycerin, mixed triester with caprylic acid capric acid according to claim 1, is characterized in that: the weight ratio of the pungent decylate of described glycerine list and oxyethane is 1:1-3.0; Basic catalyst in described ethylene oxide condensation reaction is the 0.1%-0.5% of single pungent decylate and oxyethane gross weight.
5. according to the preparation method of a kind of polyoxyethylene list Glycerin, mixed triester with caprylic acid capric acid described in claim 1 or 4, it is characterized in that: the basic catalyst in described ethylene oxide condensation reaction is for adopting sodium hydroxide.
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| CN102963577B (en) * | 2012-11-28 | 2015-01-07 | 广州嘉德乐生化科技有限公司 | Method for packaging glycerin monostearate |
| CN103145554A (en) * | 2013-02-22 | 2013-06-12 | 玛耀生物医药（上海）有限公司 | Preparation method of 1-decanoyl-rac-glycerol compound |
| CN104974340B (en) * | 2015-06-25 | 2017-03-29 | 淄博德信联邦化学工业有限公司 | The preparation method of the polyether polyol with high activity containing ester bond in main chain |
| CN105399941A (en) * | 2015-12-10 | 2016-03-16 | 浙江皇马科技股份有限公司 | A preparing method of polyether polyol aliphatic esters |
| CN108299638B (en) * | 2017-12-29 | 2020-04-28 | 浙江皇马科技股份有限公司 | Synthesis method of allyl alcohol polyoxyethylene ether carboxylic glycidyl ester |
| CN108822289A (en) * | 2018-07-12 | 2018-11-16 | 广州汇科精细化工有限公司 | Composite catalyst and its application and the method for preparing water-soluble aliphatic ester |
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| "丙三醇辛酸酯聚氧乙烯醚的合成及应用";杨勇军等;《精细石油化工》;19961130(第6期);第9-12页 * |
| JP特开2003-253175A 2003.09.10 |
| 杨勇军等."丙三醇辛酸酯聚氧乙烯醚的合成及应用".《精细石油化工》.1996,(第6期),第9-12页. |
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Effective date of registration: 20150706 Address after: 312363 Shangyu City, Zhejiang Province Zhang Town Industrial Zone Patentee after: Zhejiang Huangma Technology Co., Ltd. Address before: 312363, Zhejiang, Shangyu, Shaoxing Province town industrial zone, Zhejiang Real Madrid Chemical Group Co., Ltd. Patentee before: Huangma Chemical Group Co., Zhejiang |