CN107513025A - A kind of synthetic method of fatty diglycollic amide - Google Patents
A kind of synthetic method of fatty diglycollic amide Download PDFInfo
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- CN107513025A CN107513025A CN201710991303.8A CN201710991303A CN107513025A CN 107513025 A CN107513025 A CN 107513025A CN 201710991303 A CN201710991303 A CN 201710991303A CN 107513025 A CN107513025 A CN 107513025A
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- dea
- diethanol amine
- diglycollic amide
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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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
- C07C231/24—Separation; Purification
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Present invention relates particularly to a kind of synthetic method of fatty diglycollic amide, comprise the following steps：1) raw fatty acid, diethanol amine（DEA）Pretreatment purification；2) under N2 air-flow protections, by aliphatic acid and diethanol amine（DEA）Carry out amidatioon and ammonolysis two-step reaction；3）Adsorption treatment finally is carried out with activated carbon, filters to obtain fatty diglycollic amide.Pass through made from the above method 1:The advantages such as 1 type fatty diglycollic amide possesses purity height, lighter color, smell is light, amine value is low.
Description
Technical field
The invention belongs to the synthesis technical field of amides compound in organic chemistry, and in particular to a kind of aliphatic acid diethyl
The synthetic method of alkylolamides.
Background technology
Fatty diglycollic amide meets below formula：
Fatty diglycollic amide has the performances such as excellent foam enhancing, foam stabilizing, thickening, decontamination and emulsification, and has certain anti-quiet
Electric energy power and rust-preventing characteristic, therefore foam booster, foam stabilizer, antirust agent, antistatic additive and dispersant etc. can be used as, purposes is very
Extensively.
Different according to used raw material, industrial production fatty acid alkanol amides typically have following three routes at present：
1st, glycerine ester process
By coconut oil, palm fibre the directly reaction of the greases such as benevolence oil and diethanol amine is put to be made, this route reaction is not easy completely, generation it is sweet
Oil can form a series of accessory substances, and the by-product glycerin remained in product is up to 10% or so.
2nd, methyl esters method
Reacted at reduced pressure conditions by fatty acid methyl ester and diethanol amine, in products obtained therefrom the purity of fatty diglycollic amide compared with
Height, but fatty acid methyl ester complex operation is produced, and the larger and inflammable and explosive methanol of toxicity is used, secure context, which lacks, to be protected
Barrier.
3rd, fatty acid process
Production fatty acid alkanol amides are directly reacted with alkanolamine with aliphatic acid, its synthetic method mainly has the following two kinds：It is a kind of
It is direct method, aliphatic acid mixes with alkanolamine, directly heats dehydrating step completion；Also a kind of two-step method, first step aliphatic acid
With first being reacted under diethanol amine high temperature, amino ester and carboxylic acid amide esters, second step addition base catalyst, unreacted diethanol are generated
Amine carries out ammonolysis reaction at a lower temperature with amino ester and carboxylic acid amide esters, produces fatty acid alkanol amides；Two in one-step method reaction
For monoethanolamine in addition to amino and fatty acid response generation acid amides, its alcoholic extract hydroxyl group can also generate ester, therefore product with fatty acid response
In in addition to purpose product, it is relatively low also to have accessory substance, the product purities such as amine ester, carboxylic acid amide esters, amine soap.And two-step method is exactly one-step method
The optimization of reaction, carboxylic acid amide esters carry out aminolysis with the diethanol amine of excess under base catalyst effect, can promptly changed
For alkanolamide, technique is simple, by-product significantly reduces, and purity significantly improves.
The content of the invention
Simple to operate it is an object of the invention to provide a kind of rational technology, one kind that product color is more shallow, purity is higher is high
The synthetic method of quality fat acid diglycollic amide.
This invention takes following technical scheme：
A kind of fatty diglycollic amide and its synthetic method, comprise the following steps：With aliphatic acid and diethanol amine（DEA）For original
Material, carries out pretreatment purification by this two raw material first；Then under N2 air-flow protections, by aliphatic acid and a certain amount of diethanol amine
（DEA）Carry out amidation process；Add remaining diethanol amine（DEA）And base catalyst, it is anti-that heating stirring carries out ammonolysis
Should；Finally handled with charcoal absorption, filter to obtain fatty diglycollic amide product.
The aliphatic acid and diethanol amine（DEA）Molal weight ratio be 1:1.1 ~ 1.5, wherein added in amidation process
Diethanol amine（DEA）For the 40 ~ 60% of its gross weight, remaining diethanol amine（DEA）Added in ammonolysis reaction.
The aliphatic acid is stearic acid, palmitic acid, arachidic acid, any one or more mixtures of behenic acid.
In the pretreatment purification step of the raw fatty acid, after raw fatty acid heating melting, clear water washing is added
Twice, soap therein, glycerine and some other water-solubility impurity are removed, moisture content is then evaporated off, is purified
Aliphatic acid.
The raw material diethanol amine（DEA）Pretreatment purification step in, be in diethanol amine（DEA）Add in the aqueous solution
Enter sodium hydroxide, sodium hydroxide can generate salt with the triethanolamine reaction wherein mixed and separate out, and be filtered to remove precipitate, then enter
Water-filling steam distillation removes monoethanolamine impurity, is finally evaporated under reduced pressure the diethanol amine that must can be refined.
In the amidatioon and ammonolysis reaction, the inert nitrogen gas that shields, out of, displacement system before reaction
Air can guarantee that contact of each reactive material with air in isolation chemical reaction, prevent from reacting to the purging of whole course of reaction
Thing is oxidized and deepens color and luster, effectively prevent the coloring in course of reaction, the color and luster of product has been obtained very big improvement；Nitrogen
Air-flow can also take the water of reaction generation out of, promote reaction to be smoothed out to positive direction.
In the amidatioon and ammonolysis reaction, aliphatic acid is molten state, wherein diethanol amine（DEA）With diethanol amine
（DEA）1 ~ 2%/min of total amount speed is added in reaction system with peristaltic pump；Molten state is easier to reaction and carried out.
The base catalyst is sodium methoxide, and its addition is aliphatic acid and diethanol amine（The 0.4 of DEA gross weights ~
1.0%, and the sodium methoxide is the methanol solution of the sodium methoxide of concentration 30%.
The temperature of the amidation process is 135 ~ 155 DEG C, and the reaction time is 4 ~ 7h；The temperature of ammonolysis reaction is 60 ~ 100
DEG C, mixing time is 2 ~ 5h.
The dosage of the activated carbon is the 2 ~ 10% of fatty acid wt.Adsorbed compared to atlapulgite, the advantages of activated carbon
Show that particle is big, very easily filtered out after the completion of absorption, and carclazyte is in fine powdered, plus diethanol amine（DEA）Viscosity compared with
Greatly, difficulty is filtered out.
The present invention synthesis main reaction equation be：
The present invention compared with prior art, has advantage following prominent and good effect：
1st, raw material diethanol amine（DEA）In more or less containing impurity and the moisture content such as monoethanolamine, triethanolamine, it is preprocessed to carry
After pure, above-mentioned impurity is separated and removed；Raw fatty acid eliminates the soaps wherein contained, glycerine and other miscellaneous by purification
Matter, consequently, it is possible to which the raising of two material purities, so as to reduce possible side reaction in synthetic reaction of the present invention, produces purpose
Thing purity is lifted；
2nd, 1 is synthesized using two step feeding methods:1 type fatty diglycollic amide, technique is simple, reaction condition is gentle, side reaction is few,
Avoid using the stronger methanol of toxicity, energy consumption is less, is beneficial to green；
3rd, the pretreatment purification, the condition control of building-up process and the several keys of adsorption treatment of activated carbon that the present invention passes through raw material
Step, obtained fatty diglycollic amide, it shows as：Not only purity is significantly improved compared with existing level up to more than 93%,
And the function admirable such as lighter color, smell are light, emulsification, thickening, foam stabilizing, suitable for fields such as textile printing and dyeing, daily use chemicals washings.
Embodiment
The present invention is described in further detail with reference to embodiment, it should be appreciated that these embodiments are only used for
Illustrate the application of the present invention rather than the limitation present invention.
Embodiment 1
Take 200 grams of stearic acid and 105 grams of diethanol amine to make pretreatment purification respectively, after opening nitrogen stream protection, make described 200 grams
Stearic acid is heated to after being in molten state, is slowly dropped into 48 grams of diethanol amine with 30 drops/min speed, and be heated to 145
DEG C, keep reaction 5h.Then reaction is cooled to 80 DEG C, adds 5 grams of sodium methoxide solutions, be slowly dropped into 30 drops/min speed
Remaining diethanol amine（DEA）, insulation reaction 3h.18 grams of activated carbons are eventually adding, is kept for half an hour, filters, obtain stearic while hot
Fat acid diglycollic amide, near-white waxy solid, purity 93.37%.
Comparative example
After opening nitrogen stream protection, it will not carry out pre-processing 200 grams of industrial goods stearic acid (200 type) of purification, be heated to melting,
It is slowly dropped into not pretreated 48 grams of diethanol amine to enter in reaction bulb, and is heated to 145 DEG C, keeps reaction 6h.Then will be anti-
80 DEG C should be cooled to, adds 5 grams of sodium methoxide solutions, instills remaining 57 grams of diethanol amine, insulation reaction 3h.It is eventually adding 18 grams of work
Property charcoal, keep half an hour, filter while hot, obtain Stearic acid diethanolamine salt, pale yellow waxy solid, purity 83.58%.
Comparative illustration：Compared with Example 1, except reduce to two raw materials pretreatment purification, other conditions all with reality
Apply that example 1 is identical, the results show good effect that carries out the importance of pretreatment of raw material purification and played.
Embodiment 2
After opening nitrogen stream protection, 200 grams of stearic acid by pretreatment are heated to melting, it is slow with 40 drops/min speed
Instill 52.5 grams of diethanol amine to enter in reaction bulb, and be heated to 135 DEG C, keep reaction 6h.Then reaction is cooled to 90 DEG C, added
Enter 5 grams of sodium methoxide solutions, instill remaining 52.5 grams of diethanol amine, insulation reaction 4h.20 grams of activated carbons are eventually adding, keep half
Hour, filter while hot, obtain Stearic acid diethanolamine salt, near-white waxy solid, purity 91.86%.
Embodiment 3
After opening nitrogen stream protection, 250 grams of behenic acids by pretreatment are heated to melting, it is slow with 20 drops/min speed
Instill 50 grams of diethanol amine to enter in reaction bulb, and be heated to 155 DEG C, keep reaction 7h.Then reaction is cooled to 100 DEG C, added
Enter 59 grams of diethanol amine, 8.5 grams of sodium methoxide solutions, insulation reaction 4h.23 grams of activated carbons are eventually adding, are kept for half an hour, while hot
Filtering, obtains behenic acid diglycollic amide, near-white waxy solid, purity 90.25%.
Embodiment 4（Comparative example 1）
200 grams of stearic acid and 105 grams of diethanol amine are taken to make pretreatment purification respectively,To reaction system applying vacuum, make system Pressure is maintained at 50mmHg or lower, 200 grams of stearic acid are heated to（It is in）After molten state, with 30 drops/min speed
48 grams of diethanol amine are slowly dropped into, and are heated to 145 DEG C, keep reaction 5h.Then reaction is cooled to 80 DEG C, adds 5 grams of first
Alcohol sodium solution, remaining diethanol amine, insulation reaction 3h are slowly dropped into 30 drops/min speed.After the completion of reaction, remove true
Sky, 18 grams of activated carbons are added, kept for half an hour, filter while hot, obtain Stearic acid diethanolamine salt, dark brown waxy solid, purity
93.23%。
Embodiment 5
Take 200 grams of stearic acid and 85 grams of diethanol amine to make pretreatment purification respectively, after opening nitrogen stream protection, make described 200 grams
Stearic acid is heated to after being in molten state, is slowly dropped into 33 grams of diethanol amine with 20 drops/min speed, and be heated to 155
DEG C, keep reaction 4h.Then reaction is cooled to 70 DEG C, adds 9 grams of sodium methoxide solutions, be slowly dropped into 20 drops/min speed
Remaining diethanol amine（DEA）, insulation reaction 5h.25 grams of activated carbons are eventually adding, is kept for half an hour, filters, obtain stearic while hot
Fat acid diglycollic amide, near-white waxy solid, purity 93.09%.
Described above is only the better embodiment of the present invention, therefore all constructions according to described in present patent application scope,
The equivalent change or modification that feature and principle are done, is included in the range of present patent application.
Claims (9)
- A kind of 1. synthetic method of fatty diglycollic amide, with aliphatic acid and diethanol amine（DEA）For raw material, its feature exists In comprising the following steps:1）By raw fatty acid and raw material diethanol amine（DEA）Pretreatment purification is carried out respectively；2）In N2Under air-flow protection, with the aliphatic acid of above-mentioned preprocessed purification and a certain amount of diethanol amine（DEA）It is former for reaction Material, carry out amidation process；Then remaining diethanol amine is added（DEA）And base catalyst, it is anti-that heating stirring carries out ammonolysis Should；The aliphatic acid and diethanol amine（DEA）Mol ratio be 1:1.1~1.5；The diethanol added in the amidation process Amine（DEA）For the 40 ~ 60% of its gross weight, remaining diethanol amine（DEA）Added in ammonolysis reaction；3）Handled with charcoal absorption, filter to obtain fatty diglycollic amide.
- A kind of 2. synthetic method of fatty diglycollic amide as described in claim 1, it is characterised in that：The aliphatic acid is Laurate, palmitic acid, stearic acid, arachidic acid, any one or more mixtures of behenic acid.
- A kind of 3. synthetic method of fatty diglycollic amide as described in claim 1, it is characterised in that：Step 1）Described in The pretreatment purification step of raw fatty acid is：Raw fatty acid is washed by heating melting, clear water successively, is evaporated under reduced pressure, The aliphatic acid purified.
- A kind of 4. synthetic method of fatty diglycollic amide as described in claim 1, it is characterised in that：Step 1）Described in Raw material diethanol amine（DEA）Pretreatment purification step be：By raw material diethanol amine（DEA）Steamed successively by washing, filtering, water Steam distillation and vacuum distillation, the diethanol amine purified（DEA）；In diethanol amine during the water-washing step（DEA）The aqueous solution Middle addition sodium hydroxide.
- A kind of 5. synthetic method of fatty diglycollic amide as described in claim 1, it is characterised in that：The step 2）Close When starting into reaction, aliphatic acid is molten state, diethanol amine（DEA）With diethanol amine（DEA）1 ~ 2%/min of total amount speed Add.
- A kind of 6. synthetic method of fatty diglycollic amide as described in claim 1, it is characterised in that：The base catalysis Agent is sodium methoxide, and its addition is aliphatic acid and diethanol amine（DEA）The 0.4 ~ 1.0% of gross weight, the sodium methoxide are concentration The methanol solution of 30% sodium methoxide.
- A kind of 7. synthetic method of fatty diglycollic amide as described in claim 1, it is characterised in that:The amidatioon is anti- The reaction temperature answered is 135 ~ 155 DEG C, and the reaction time is 4 ~ 7h；
- A kind of 8. synthetic method of fatty diglycollic amide as described in claim 1, it is characterised in that:The ammonolysis is anti- The reaction temperature answered is 60 ~ 100 DEG C, and mixing time is 2 ~ 5h.
- A kind of 9. synthetic method of fatty diglycollic amide as described in claim 1, it is characterised in that：The activated carbon Dosage is the 2 ~ 10% of fatty acid wt.
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| CN201710991303.8A CN107513025A (en) | 2017-10-23 | 2017-10-23 | A kind of synthetic method of fatty diglycollic amide |
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| CN201710991303.8A CN107513025A (en) | 2017-10-23 | 2017-10-23 | A kind of synthetic method of fatty diglycollic amide |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111511885A (en) * | 2017-12-27 | 2020-08-07 | 欧荔安股份有限公司 | Composition useful as a friction modifier |
| CN112479915A (en) * | 2020-11-27 | 2021-03-12 | 德旭新材料(广州)股份有限公司 | N-octanoic acid diisopropanolamine, preparation method thereof and corrosion inhibitor |
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| CN100999482A (en) * | 2006-11-28 | 2007-07-18 | 王伟松 | Synthesizing process of fatty diglycollic amide |
| CN102212017A (en) * | 2011-04-07 | 2011-10-12 | 上虞市佳华高分子材料有限公司 | High-content synthesis method of diethanolamide stearate |
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2017
- 2017-10-23 CN CN201710991303.8A patent/CN107513025A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100999482A (en) * | 2006-11-28 | 2007-07-18 | 王伟松 | Synthesizing process of fatty diglycollic amide |
| CN102212017A (en) * | 2011-04-07 | 2011-10-12 | 上虞市佳华高分子材料有限公司 | High-content synthesis method of diethanolamide stearate |
Non-Patent Citations (1)
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|---|
| 郑延成等: "脂肪酸二乙醇酰胺类表面活性剂合成研究", 《长江大学学报（自然科学版）》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111511885A (en) * | 2017-12-27 | 2020-08-07 | 欧荔安股份有限公司 | Composition useful as a friction modifier |
| CN112479915A (en) * | 2020-11-27 | 2021-03-12 | 德旭新材料(广州)股份有限公司 | N-octanoic acid diisopropanolamine, preparation method thereof and corrosion inhibitor |
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Application publication date: 20171226 |