CN105777568A - Preparation method of vinyl distearamide - Google Patents
Preparation method of vinyl distearamide Download PDFInfo
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- CN105777568A CN105777568A CN201610218117.6A CN201610218117A CN105777568A CN 105777568 A CN105777568 A CN 105777568A CN 201610218117 A CN201610218117 A CN 201610218117A CN 105777568 A CN105777568 A CN 105777568A
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- preparation
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- antioxidant
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
Abstract
The invention belongs to the technical field of chemical engineering and particularly relates to a preparation method of vinyl distearamide. The preparation method uses stearic acid and ethylenediamine as reacting raw materials, uses a composite antioxidant prepared by compounding an antioxidant 1076, an antioxidant DLTDP and an antioxidant T501 as a reacting antioxidant and uses a composite catalyst prepared by compounding a p-Toluene sulfonic acid/SAPO-34 supported solid acid catalyst and a phosphoric acid/SiO2-Al2O3 supported solid acid catalyst as a reaction catalyst. The preparation method of the vinyl distearamide is simple in process, no 'three wastes' emission is produced in the process of preparing the vinyl distearamide, the yield is high, and the prepared vinyl distearamide is high in purity, low in chromaticity and narrow in melting range.
Description
Technical field
The invention belongs to chemical technology field, be specifically related to the preparation method of a kind of vinyl bis-stearamides.
Background technology
Fatty acid bis-amides compounds is widely used in various macromolecular material and Wood-plastic material, has lubrication, the demoulding, anti-stick
Connect, antistatic and the dispersion of promotion pigment, increase the several functions such as product surface gloss.Vinyl bis-stearamides be also known as N, N '-
Ethylene bis stearamide (EBS), is to develop one of fatty bis-amide series products the earliest, containing polar amide in EBS structure
Group and the hydrophobic group of two Long carbon chain so that it is have the feature such as high temperature lubricating and low temperature antistick characteristic, add itself and synthesis
Resin such as acrylonitrile-butadiene-styrene (ABS) polymer (ABS), polrvinyl chloride, phenolic resin, polystyrene etc. have good
The compatibility, is that one has multi-functional processing aid, can be used for inside and outside lubricant agent, defoamer, dispersant, antistatic additive,
Pore formers etc., have extremely wide application in the industrial production.EBS is harmless to human body and organism, therefore also act as
Packaging material for food, auxiliary agent, additive etc..
The synthetic method of EBS mainly has four kinds: 1) fatty acid ester and aminated compounds react generation EBS, the product of this method gained
Product purity is higher, but energy consumption is big, and in the esterification of fatty acid and course of reaction, the process of alcohol makes complex process, and operation is long；2)
Acyl chlorides and aminated compounds react preparation EBS, reduce reaction temperature, and product purity is high, and color and luster is good, but production cost is high,
Technological process is long；3) hydrolysis of nitrile cyanogen compound, owing to cyanide is poisonous, production process environmental pollution is serious, and this method is
Eliminate；4) fatty acid and aminated compounds react preparation EBS, and method technique is simple, reaction condition is gentle, raw material is easy to get for this, three
Useless few, it is current domestic main EBS synthetic route.It is double hard that Chinese patent application CN102964266A discloses a kind of ethylene
The synthesis technique of acyl amine height yield, with stearic acid and ethylenediamine as reaction raw materials, phosphoric acid and acetic anhydride are catalyst, sulfurous acid
Salt is antioxidant, and this invention synthesis technique is simple, and easy to operate, the three wastes are few, but color is relatively deep, and product melting range is wider.
The method technique that stearic acid and reacting ethylenediamine prepare EBS is simple, it is easy to large-scale production, but the EBS prepared
Product is commonly present the problems such as product purity is low, color is easily turned to be yellow, colourity is higher, melting range width, and therefore its synthesis technique need to change
Enter.
Summary of the invention
It is an object of the invention to overcome existing technological deficiency, it is provided that the preparation method of a kind of vinyl bis-stearamides.This
The preparation method technique of the vinyl bis-stearamides of bright offer is simple, without the three wastes during preparing vinyl bis-stearamides
Discharge, productivity is high, and the vinyl bis-stearamides purity prepared is high, and colourity is low, and melting range is narrow, and technology requires to meet or super
The more relevant criterion of HG/T 4784-2014.
Technical scheme is as follows:
The preparation method of a kind of vinyl bis-stearamides, comprises the steps:
Stearic acid and composite antioxidant are added in reactor, is passed through N while stirring2, after 8-15min, it is to slowly warm up to
80-100 DEG C, make stearic acid all melt, add ethylenediamine and composite catalyst, isothermal reaction 1-2 hour, more slowly heat up
To 170-180 DEG C, isothermal reaction is allowed to carry out dehydration for 3-5 hour, and the water generated in course of reaction is by N2Take out of, measure
Product acid number, when acid number is less than 10mgKOH/g, stopped reaction, it is cooled to 160 DEG C of dischargings；
Wherein, the mol ratio of described stearic acid and ethylenediamine is 1: 0.56-0.60；Described composite antioxidant consumption is stearic acid matter
The 0.20-0.32% of amount；The consumption of described composite catalyst is the 0.15-0.25% of stearic acid quality.
Preferably, described composite antioxidant includes antioxidant 1076, antioxidant DLTDP and antioxidant T501, the most excellent
Selection of land, the mass ratio of antioxidant 1076, antioxidant DLTDP and antioxidant T501 is 0.15-0.28: 0.30-0.46: 1.
Preferably, described composite catalyst includes p-methyl benzenesulfonic acid/SAPO-34 load-type solid acid catalyst and phosphoric acid
/SiO2-Al2O3Load-type solid acid catalyst, it is further preferred that p-methyl benzenesulfonic acid/SAPO-34 supported solid acid catalysis
Agent and phosphoric acid/SiO2-Al2O3The mass ratio of load-type solid acid catalyst is 1: 2-5.
Preferably, the preparation method of described p-methyl benzenesulfonic acid/SAPO-34 load-type solid acid catalyst comprises the following steps: will
P-methyl benzenesulfonic acid is dissolved in deionized water, prepares p-methyl benzenesulfonic acid solution as impregnation liquid, with through 450-550 DEG C of roasting 3-5h
After SAPO-34 molecular sieve be placed in p-methyl benzenesulfonic acid solution by liquid-solid ratio 1.5-2.8mL/g as carrier, use ultrasound wave
Infusion process impregnates, and dip time is 8-15h；By the dry 10-15h of material 100-120 DEG C good for above-mentioned dipping, use air
Atmosphere is 500-600 DEG C of roasting 3-5h in Muffle furnace, to obtain final product.
Preferably, in the preparation method of described p-methyl benzenesulfonic acid/SAPO-34 load-type solid acid catalyst, p-methyl benzenesulfonic acid
The mass fraction of solution is 25-35%.
Preferably, described phosphoric acid/SiO2-Al2O3The preparation method of load-type solid acid catalyst comprises the following steps: divide with quality
Number is impregnation liquid for the phosphoric acid solution of 80-85%, with SiO2-Al2O3Composite oxides press liquid-solid ratio 0.8-1.2mL/g as carrier
Being placed in phosphoric acid solution, use ultrasound wave infusion process to impregnate, dip time is 10-16h；The material good by above-mentioned dipping
100-120 DEG C of dry 10-15h, uses air atmosphere 500-600 DEG C of roasting 2-5h in Muffle furnace, to obtain final product.
Preferably, described phosphoric acid/SiO2-Al2O3In the preparation method of load-type solid acid catalyst, the mass fraction of phosphoric acid solution
For 50-60%.
In the molten state, stearic acid and reacting ethylenediamine, generate intermediate amine salt, amine salt decomposes more than 140 DEG C, sloughs
Two molecular waters, prepare vinyl bis-stearamides.Intermediate amine salt easily colours, and salification process is an exothermic reaction, should
Controlling reaction temperature, the too high meeting of temperature causes ethylenediamine steam raising, and antioxidant consumption increases, and also results in aminolysis reaction, shadow
Ring product colourity, it is therefore desirable to select suitable catalyst and antioxidant, to ensure that in building-up process, material is not oxidized, it is ensured that
Product colourity.The present invention passes through the control of course of reaction temperature and selects composite antioxidant and composite solid-acid catalyst as tristearin
Acid and reacting ethylenediamine prepare the catalyst during vinyl bis-stearamides and antioxidant, reduce the colourity of product, subtract simultaneously
The generation of few side reaction, the vinyl bis-stearamides colourity prepared is low, and fusing point is excellent, and purity is high, and productivity is high.
Compared with prior art, the invention has the beneficial effects as follows: the preparation method work of the vinyl bis-stearamides that the present invention provides
Skill is simple, three-waste free discharge during preparing vinyl bis-stearamides, and control and selection by course of reaction temperature are multiple
Close antioxidant and composite solid-acid catalyst and prepare the catalysis during vinyl bis-stearamides as stearic acid and reacting ethylenediamine
Agent and antioxidant, reduce the colourity of product, reduce the generation of side reaction, the vinyl bis-stearamides purity prepared simultaneously
Height, colourity is low, and melting range is narrow, and productivity is high, and technology requires to meet or surmount the relevant criterion of HG/T 4784-2014..
Detailed description of the invention
Further describe the present invention below by way of detailed description of the invention, but the present invention is not limited only to following example.In the present invention
In the range of or without departing from present disclosure, spirit and scope, pharmaceutical composition of the present invention is carried out suitably
Improve, replace the component that effect is identical, will become apparent to those skilled in the art that they are considered as being included in
Within the scope of the present invention.
Embodiment 1 prepares p-methyl benzenesulfonic acid/SAPO-34 load-type solid acid catalyst
P-methyl benzenesulfonic acid is dissolved in deionized water, prepares p-methyl benzenesulfonic acid solution that mass fraction is 30% as impregnation liquid,
It is placed in p-methyl benzenesulfonic acid solution as carrier by liquid-solid ratio 2.0mL/g using the SAPO-34 molecular sieve after 500 DEG C of roasting 3.5h
In, use ultrasound wave infusion process to impregnate, dip time is 12h；By 120 DEG C of dry 12h of material good for above-mentioned dipping, adopt
With air atmosphere 550 DEG C of roasting 4h in Muffle furnace, obtain p-methyl benzenesulfonic acid/SAPO-34 load-type solid acid catalyst.
Embodiment 2 prepares phosphoric acid/SiO2-Al2O3 load-type solid acid catalyst
S1: take aluminum nitrate, is dissolved in dehydrated alcohol by solid-to-liquid ratio 0.10g/mL, prepares aluminum nitrate ethanol solution, adds its volume
The tetraethyl orthosilicate of 40% and the aqueous solution of urea that volume fraction is 30% of its volume 15%, stir 10min, in 80 DEG C of stirrings
Backflow plastic, 120 DEG C of dry 8h, 550 DEG C of roasting 3h in Muffle furnace, prepare SiO2-Al2O3Composite oxides；
S2: with phosphoric acid solution that mass fraction is 55% as impregnation liquid, the SiO prepared with S12-Al2O3Composite oxides conduct
Carrier is placed in phosphoric acid solution by liquid-solid ratio 1.0mL/g, uses ultrasound wave infusion process to impregnate, and dip time is 16h；Will
120 DEG C of dry 12h of material that above-mentioned dipping is good, use air atmosphere 550 DEG C of roasting 4h in Muffle furnace, obtain phosphoric acid
/ SiO2-Al2O3 load-type solid acid catalyst.
Embodiment 3 prepares the double stearoylketene amine of vinyl
The composite antioxidant of stearic acid and stearic acid quality 0.28% is added in reactor, is passed through N while stirring2, after 10min,
It is to slowly warm up to 100 DEG C, makes stearic acid all melt, add ethylenediamine and the composite catalyst of stearic acid quality 0.20%, constant temperature
Reacting 2 hours, then be to slowly warm up to 180 DEG C, isothermal reaction is allowed to carry out dehydration for 4 hours, generates in course of reaction
Water is by N2Take out of, stopped reaction, be cooled to 160 DEG C of dischargings.Wherein, the mol ratio of stearic acid and ethylenediamine is 1: 0.58；
In composite antioxidant, the mass ratio of antioxidant 1076, antioxidant DLTDP and antioxidant T501 is 0.20: 0.36: 1；Composite catalyzing
Agent uses embodiment 1 and embodiment 2 prepared p-methyl benzenesulfonic acid/SAPO-34 load-type solid acid catalyst and phosphoric acid
/SiO2-Al2O3Load-type solid acid catalyst, its mass ratio is 1: 3.5.The productivity recording vinyl bis-stearamides is 94.3%.
Embodiment 4 prepares the double stearoylketene amine of vinyl
The composite antioxidant of stearic acid and stearic acid quality 0.23% is added in reactor, is passed through N while stirring2, after 12min,
It is to slowly warm up to 90 DEG C, makes stearic acid all melt, add ethylenediamine and the composite catalyst of stearic acid quality 0.18%, constant temperature
Reacting 2 hours, then be to slowly warm up to 175 DEG C, isothermal reaction is allowed to carry out dehydration for 3.8 hours, generates in course of reaction
Water is by N2Take out of, stopped reaction, be cooled to 160 DEG C of dischargings.Wherein, the mol ratio of stearic acid and ethylenediamine is 1: 0.56；
In composite antioxidant, the mass ratio of antioxidant 1076, antioxidant DLTDP and antioxidant T501 is 0.23: 0.40: 1；Composite catalyzing
Agent uses embodiment 1 and embodiment 2 prepared p-methyl benzenesulfonic acid/SAPO-34 load-type solid acid catalyst and phosphoric acid
/SiO2-Al2O3Load-type solid acid catalyst, its mass ratio is 1: 4.The productivity recording vinyl bis-stearamides is 93.6%.
Comparative example 1 prepares the double stearoylketene amine of vinyl
In preparation process, antioxidant uses antioxidant 1076 and the composite antioxidant of antioxidant DLTDP, and its mass ratio is 1: 0.62,
Remaining is with embodiment 3.The productivity recording vinyl bis-stearamides is 62.8%.
Comparative example 2 prepares the double stearoylketene amine of vinyl
In preparation process, antioxidant uses antioxidant DLTDP and the composite antioxidant of antioxidant T501, and its mass ratio is 0.45: 1,
Remaining is with embodiment 3.The productivity recording vinyl bis-stearamides is 82.4%.
Comparative example 3 prepares the double stearoylketene amine of vinyl
In preparation process, catalyst uses p-methyl benzenesulfonic acid and the composite catalyst of phosphoric acid, and its mass ratio is 1: 3.5, and remaining is same
Embodiment 3.The productivity recording vinyl bis-stearamides is 84.7%.
Reference People's Republic of China (PRC) chemical industry standard HG/T 4784-2014 " N, N '-ethylene bis stearamide (EBS) " right
Vinyl bis-stearamides prepared by the present invention carries out the detection of index of correlation, and testing result is shown in Table 1.
Table 1 vinyl bis-stearamides Indexs measure result
From table 1 result of the test, the vinyl bis-stearamides indices that the present invention prepares all meets HG/T
The relevant criterion of 4784-2014, product purity is high, and colourity is low, and melting range is narrow, and productivity is high, the second that wherein embodiment 3 prepares
Thiazolinyl bis-stearamides reaches the quality standard of high-class product, for preferred embodiment.Compared with comparative example 1-2, the present invention
The vinyl bis-stearamides colourity that embodiment 3 prepares is low, and acid number is low, and melting range is narrow, illustrate the present invention use antioxidant 1076,
The composite antioxidant that antioxidant DLTDP and antioxidant T501 compounds, as reaction antioxidant, advantageously reduces and prepares
The colourity of vinyl bis-stearamides and acid number；Compared with comparative example 3, the embodiment of the present invention 3 uses p-methyl benzenesulfonic acid
/ SAPO-34 load-type solid acid catalyst and phosphoric acid/SiO2-Al2O3The composite catalyzing that load-type solid acid catalyst compounds
Agent is superior to urge with p-methyl benzenesulfonic acid and phosphoric acid for reaction as the vinyl bis-stearamides indices that catalysts prepares
The vinyl bis-stearamides that agent prepares, meanwhile, solid acid catalyst is easily recycled, repeatable utilization, can be to a certain degree
Upper reduction production cost.
Above content is to combine concrete preferred implementation further description made for the present invention, it is impossible to assert the present invention
Be embodied as be confined to these explanations.For general technical staff of the technical field of the invention, without departing from this
On the premise of inventive concept, it is also possible to make some simple deduction or replace, all should be considered as belonging to protection scope of the present invention.
Claims (9)
1. the preparation method of a vinyl bis-stearamides, it is characterised in that described preparation method comprises the steps:
Stearic acid and composite antioxidant are added in reactor, is passed through N while stirring2, after 8-15min, it is to slowly warm up to
80-100 DEG C, make stearic acid all melt, add ethylenediamine and composite catalyst, isothermal reaction 1-2 hour, more slowly heat up
To 170-180 DEG C, isothermal reaction is allowed to carry out dehydration for 3-5 hour, and the water generated in course of reaction is by N2Take out of, measure
Product acid number, when acid number is less than 10mgKOH/g, stopped reaction, it is cooled to 160 DEG C of dischargings；
Wherein, the mol ratio of described stearic acid and ethylenediamine is 1: 0.56-0.60；Described composite antioxidant consumption is stearic acid matter
The 0.20-0.32% of amount；The consumption of described composite catalyst is the 0.15-0.25% of stearic acid quality.
The preparation method of vinyl bis-stearamides the most according to claim 1, it is characterised in that described compound anti-oxidation
Agent includes antioxidant 1076, antioxidant DLTDP and antioxidant T501.
The preparation method of vinyl bis-stearamides the most according to claim 2, it is characterised in that described composite oxidant
In, the mass ratio of antioxidant 1076, antioxidant DLTDP and antioxidant T501 is 0.15-0.28: 0.30-0.46: 1.
The preparation method of vinyl bis-stearamides the most according to claim 1, it is characterised in that described composite catalyst
Including p-methyl benzenesulfonic acid/SAPO-34 load-type solid acid catalyst and phosphoric acid/SiO2-Al2O3Load-type solid acid catalyst.
The preparation method of vinyl bis-stearamides the most according to claim 4, it is characterised in that described composite catalyst
In, p-methyl benzenesulfonic acid/SAPO-34 load-type solid acid catalyst and phosphoric acid/SiO2-Al2O3The matter of load-type solid acid catalyst
Amount ratio is 1: 2-5.
6. according to the preparation method of the vinyl bis-stearamides described in claim 4 or 5, it is characterised in that described to methyl
The preparation method of benzenesulfonic acid/SAPO-34 load-type solid acid catalyst comprises the following steps: p-methyl benzenesulfonic acid is dissolved in deionization
In water, prepare p-methyl benzenesulfonic acid solution as impregnation liquid, make with the SAPO-34 molecular sieve after 450-550 DEG C of roasting 3-5h
It is placed in p-methyl benzenesulfonic acid solution by liquid-solid ratio 1.5-2.8mL/g for carrier, uses ultrasound wave infusion process to impregnate, during dipping
Between be 8-15h；By the dry 10-15h of material 100-120 DEG C good for above-mentioned dipping, use air atmosphere in Muffle furnace 500-600 DEG C
Roasting 3-5h, to obtain final product.
The preparation method of vinyl bis-stearamides the most according to claim 6, it is characterised in that described to methylbenzene sulphur
In the preparation method of acid/SAPO-34 load-type solid acid catalyst, the mass fraction of p-methyl benzenesulfonic acid solution is 25-35%.
8. according to the preparation method of the vinyl bis-stearamides described in claim 4 or 5, it is characterised in that described phosphoric acid
/SiO2-Al2O3The preparation method of load-type solid acid catalyst comprises the following steps: with phosphoric acid solution as impregnation liquid, with
SiO2-Al2O3Composite oxides are placed in phosphoric acid solution by liquid-solid ratio 0.8-1.2mL/g as carrier, use ultrasound wave infusion process to enter
Row dipping, dip time is 10-16h；By the dry 10-15h of material 100-120 DEG C good for above-mentioned dipping, use air atmosphere in
In Muffle furnace, 500-600 DEG C of roasting 2-5h, to obtain final product.
The preparation method of vinyl bis-stearamides the most according to claim 8, it is characterised in that described phosphoric acid
/SiO2-Al2O3In the preparation method of load-type solid acid catalyst, the mass fraction of phosphoric acid solution is 50-60%.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107353218A (en) * | 2017-06-30 | 2017-11-17 | 广州煌垅生物科技有限公司 | A kind of method that vinyl bis-stearamides are prepared using hydrogenated oil and fat |
| CN108003051A (en) * | 2017-12-30 | 2018-05-08 | 徐州诺克非医药科技有限公司 | A kind of synthetic method of pharmaceutical intermediate Flutamide |
| CN115487861A (en) * | 2021-06-18 | 2022-12-20 | 中国石油化工股份有限公司 | Shaped esterification catalyst, preparation method thereof and application thereof in isoamyl acetate synthesis |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000191610A (en) * | 1998-12-28 | 2000-07-11 | Kao Corp | Production of higher fatty acid bisamide |
| CN101665447A (en) * | 2009-09-22 | 2010-03-10 | 如皋市双马化工有限公司 | Method for synthesizing ethylene stearamide with octadecanoic acid |
-
2016
- 2016-04-08 CN CN201610218117.6A patent/CN105777568B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000191610A (en) * | 1998-12-28 | 2000-07-11 | Kao Corp | Production of higher fatty acid bisamide |
| CN101665447A (en) * | 2009-09-22 | 2010-03-10 | 如皋市双马化工有限公司 | Method for synthesizing ethylene stearamide with octadecanoic acid |
Non-Patent Citations (1)
| Title |
|---|
| 陈信鹍等: ""直接酰胺化反应合成乙撑双硬脂酸酰胺"", 《化工生产与技术》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107353218A (en) * | 2017-06-30 | 2017-11-17 | 广州煌垅生物科技有限公司 | A kind of method that vinyl bis-stearamides are prepared using hydrogenated oil and fat |
| CN107353218B (en) * | 2017-06-30 | 2019-12-13 | 广州煌垅生物科技有限公司 | Method for preparing vinyl bis-stearamide by using hydrogenated oil |
| CN108003051A (en) * | 2017-12-30 | 2018-05-08 | 徐州诺克非医药科技有限公司 | A kind of synthetic method of pharmaceutical intermediate Flutamide |
| CN115487861A (en) * | 2021-06-18 | 2022-12-20 | 中国石油化工股份有限公司 | Shaped esterification catalyst, preparation method thereof and application thereof in isoamyl acetate synthesis |
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Address after: No. 6, Huafeng Road, Yonghe District, Guangzhou Economic and Technological Development Zone, Guangdong 510530 Patentee after: Guangdong Jiadele Technology Co.,Ltd. Address before: No. 6, Huafeng Road, Yonghe District, Guangzhou Economic and Technological Development Zone, Guangdong 510530 Patentee before: GUANGZHOU CARDLO BIOCHEMICAL TECHNOLOGY Co.,Ltd. |