CN110982061A - Preparation method and application of polyethylene glycol long-chain alkylamide - Google Patents
Preparation method and application of polyethylene glycol long-chain alkylamide Download PDFInfo
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- CN110982061A CN110982061A CN201911068446.7A CN201911068446A CN110982061A CN 110982061 A CN110982061 A CN 110982061A CN 201911068446 A CN201911068446 A CN 201911068446A CN 110982061 A CN110982061 A CN 110982061A
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- polyethylene glycol
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- monomethyl ether
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
- C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
- C08G65/3322—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof acyclic
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
- C08G65/325—Polymers modified by chemical after-treatment with inorganic compounds containing nitrogen
- C08G65/3255—Ammonia
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
- C10M149/12—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M173/00—Lubricating compositions containing more than 10% water
- C10M173/02—Lubricating compositions containing more than 10% water not containing mineral or fatty oils
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
- C08G2650/50—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing nitrogen, e.g. polyetheramines or Jeffamines(r)
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
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- Oil, Petroleum & Natural Gas (AREA)
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- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- Lubricants (AREA)
Abstract
The invention provides a preparation method and application of polyethylene glycol long-chain alkylamide, wherein polyethylene glycol monomethyl ether and ammonia gas are used for preparing polyethylene glycol amine monomethyl ether in the presence of silicon dioxide and alumina, and the polyethylene glycol amine monomethyl ether and long-chain alkyl carboxylate are dehydrated at high temperature to obtain a target product polyethylene glycol long-chain alkylamide; the method is simple and convenient to operate, has cheap and easily-obtained reagents, is green, safe, efficient and environment-friendly, and is suitable for industrial production; the polyethylene glycol long-chain alkylamide prepared by the invention has excellent lubricating property and extreme pressure wear resistance, can completely or partially replace the traditional extreme pressure wear-resistant agent containing chlorine, sulfur and phosphorus and be used in trace lubricant, a small amount of trace lubricant can meet the requirements of metal processing on lubricating cooling, extreme pressure wear resistance and rust prevention, and the polyethylene glycol long-chain alkylamide can save the use amount of the lubricant by more than 90 percent when being matched with a trace lubricating device for use, thereby having obvious effects of energy conservation, emission reduction and environmental protection.
Description
Technical Field
The invention relates to the technical field of organic synthesis and lubrication, in particular to a preparation method and application of polyethylene glycol long-chain alkylamide.
Background
The traditional metal cutting processing adopts mineral oil or vegetable oil or cutting fluid to carry out a large amount of flushing type lubrication and cooling, the using amount of the lubricant is large, resources are wasted, huge pollution to processing places and environment is caused, and meanwhile, the health of operators is seriously influenced.
Nowadays, energy conservation and emission reduction, environmental protection and green manufacturing are advocated, and a new metal cutting machining process is urgently needed. The micro-lubricating technology is a new metal green processing technology developed in recent years, namely a micro-lubricating system is used for spraying micro-lubricating oil with good extreme pressure abrasion resistance and lubricating property to a processing cutter and a processing surface for lubricating and cooling in the metal cutting processing process, and the problems of large consumption of cutting oil and liquid, large waste leakage amount and the like in the traditional processing are solved.
Disclosure of Invention
Aiming at the defects in the prior art, the invention provides a preparation method and application of polyethylene glycol long-chain alkylamide.
The present invention achieves the above-described object by the following technical means.
A preparation method of polyethylene glycol long-chain alkylamide specifically comprises the following steps:
the first step is as follows: preparing polyethylene glycol amine monomethyl ether by using polyethylene glycol monomethyl ether and ammonia gas in the presence of silica and alumina;
the second step is that: dehydrating the polyethylene glycol amine monomethyl ether and the long-chain alkyl carboxylic ester at high temperature to obtain the target product polyethylene glycol long-chain alkyl amide.
The polyethylene glycol monomethyl ether is selected from one or more of polyethylene glycol monomethyl ether with the molecular weight of 200-1000;
the polyethylene glycol monomethyl ether is preferably one or more of mPEG200, mPEG300, mPEG400, mPEG500, mPEG600, mPEG800 and mPEG 1000;
the long-chain Alkyl carboxylic acid ester (Alkyl-COOR), wherein the Alkyl is selected from straight-chain or branched Alkyl containing 6-30 carbons, and R is selected from methyl or ethyl;
in the first step, the mass ratio of the silicon dioxide to the mPEG is 0.2-0.5: 1;
in the first step, the mass ratio of the alumina to the mPEG is 1-1.5: 1;
further, in the first step, the pressure of the used ammonia gas is 2-5 atmospheric pressures;
further, in the first step, the reaction temperature is 160-200 ℃, preferably 180 ℃;
furthermore, in the second step, the mass ratio of the used long-chain alkyl carboxylic ester to the polyethylene glycol amine monomethyl ether is 1-1.2: 1;
furthermore, in the second step, the reaction temperature is 150-180 ℃, preferably 160 ℃.
The invention also relates to the application of the polyethylene glycol long-chain alkyl amide in a lubricant, and the prepared polyethylene glycol long-chain alkyl amide can be directly used as a trace lubricant. Or directly adding water with the amount less than 5 times of the amount of the lubricant per se to be used as a trace lubricant. It can also be used in trace amount together with other components.
The invention has the beneficial effects that:
the invention provides a method for preparing polyethylene glycol long-chain alkylamide, which is simple and convenient to operate, has cheap and easily-obtained reagents, is green, safe, efficient and environment-friendly, and is suitable for industrial production; the polyethylene glycol long-chain alkylamide prepared by the invention has excellent lubricating property and extreme pressure wear resistance, can completely or partially replace the traditional extreme pressure wear-resistant agent containing chlorine, sulfur and phosphorus and be used in trace lubricant, a small amount of trace lubricant can meet the requirements of metal processing on lubricating cooling, extreme pressure wear resistance and rust prevention, and the polyethylene glycol long-chain alkylamide can save the use amount of the lubricant by more than 90 percent when being matched with a trace lubricating device for use, thereby having obvious effects of energy conservation, emission reduction and environmental protection.
Drawings
FIG. 1 is a schematic diagram of the synthetic route of the present invention.
Detailed Description
The present invention will be further described with reference to the following specific examples, but the scope of the present invention is not limited thereto.
The first embodiment is as follows:
100 g (0.1mol) of polyethylene glycol monomethyl ether (mPEG1000) having a molecular weight of 1000, 3 g (0.05mol) of silica and 10 g (0.1mol) of alumina were sequentially charged into a 500ml autoclave, ammonia gas was introduced and the pressure was adjusted to 2 atmospheres, and after reacting at 180 ℃ for 36 hours, the mixture was extracted three times with water and ethyl acetate to remove the water layer, and the organic layer was dried over anhydrous sodium sulfate. Removing the solvent by using a rotary evaporator, extracting the product by using dichloromethane, and then evaporating the solvent to obtain 87 g of polyethylene glycol amine monomethyl ether, wherein the yield is 87%, and repeating the steps for multiple times to obtain sufficient polyethylene glycol amine monomethyl ether;
polyethylene glycol amine monomethyl ether (mPEG NH) is added into a 500ml high-pressure reaction kettle in sequence2) After 100 g (0.1mol) and 28 g (0.1mol) of methyl octadecanoate reacted at 160 ℃ for 36 hours, the volatiles were removed by a rotary evaporator to give 101 g of polyethylene glycol long-chain alkylamide with a yield of 81%.
The polyethylene glycol long-chain alkylamide prepared by the method is diluted by adding 2 times of water to form an environment-friendly trace lubricant, the environment-friendly trace lubricant is applied to turning and milling of aluminum alloy parts, the emulsified cutting fluid (with the concentration of about 5%) is used for circulating lubrication and cooling, the environment-friendly trace lubricant is used for trace lubrication at present, the excellent lubrication effect can be achieved by only using the trace lubricant with the volume of 2% of the original emulsified cutting fluid, the ground oil stain is less, the workpiece is clean, and the environment is clean and tidy.
Example two:
in a 500ml autoclave, 80 g (0.1mol) of polyethylene glycol monomethyl ether (mPEG800) having a molecular weight of 800, 3 g (0.05mol) of silica and 10 g (0.1mol) of alumina were sequentially charged, ammonia gas was introduced and the pressure was adjusted to 2 atmospheres, and after reacting at 180 ℃ for 36 hours, extraction was carried out three times with water and ethyl acetate to remove the water layer, and the organic layer was dried over anhydrous sodium sulfate. Removing the solvent by using a rotary evaporator, extracting a product by using dichloromethane, and then evaporating the solvent to obtain 67 g of polyethylene glycol amine monomethyl ether, wherein the yield is 84%, and repeating the steps for multiple times to obtain sufficient polyethylene glycol amine monomethyl ether;
polyethylene glycol amine monomethyl ether (mPEG NH) is added into a 500ml high-pressure reaction kettle in sequence2)80 g (0.1mol) and 24 g (0.1mol) of methyl dodecanoate were reacted at 160 ℃ for 36 hours, and then volatiles were removed by a rotary evaporator to obtain 82 g of polyethylene glycol long-chain alkylamide with a yield of 82%.
The polyethylene glycol long-chain alkylamide prepared by the method is diluted by adding 2 times of water to form an environment-friendly trace lubricant, the environment-friendly trace lubricant is applied to turning and milling of aluminum alloy parts, the emulsified cutting fluid (with the concentration of about 5%) is used for circulating lubrication and cooling, the environment-friendly trace lubricant is used for trace lubrication at present, the excellent lubrication effect can be achieved by only using the trace lubricant with the volume of 2% of the original emulsified cutting fluid, the ground oil stain is less, the workpiece is clean, and the environment is clean and tidy.
The present invention is not limited to the above-described embodiments, and any obvious improvements, substitutions or modifications can be made by those skilled in the art without departing from the spirit of the present invention.
Claims (10)
1. The preparation method of the polyethylene glycol long-chain alkylamide is characterized by comprising the following steps:
the first step is as follows: preparing polyethylene glycol amine monomethyl ether by using polyethylene glycol monomethyl ether and ammonia gas in the presence of silica and alumina;
the second step is that: dehydrating the polyethylene glycol amine monomethyl ether and the long-chain alkyl carboxylic ester at high temperature to obtain the target product polyethylene glycol long-chain alkyl amide.
2. The method for preparing polyethylene glycol long-chain alkylamide as claimed in claim 1, wherein the polyethylene glycol monomethyl ether is selected from one or more of polyethylene glycol monomethyl ethers with molecular weight of 200-1000.
3. The method for preparing polyethylene glycol long-chain alkyl amide as claimed in claim 2, wherein the polyethylene glycol monomethyl ether is preferably one or more selected from mPEG200, mPEG300, mPEG400, mPEG500, mPEG600, mPEG800 and mPEG 1000.
4. The method for preparing polyethylene glycol long-chain alkylamide according to claim 1, wherein the long-chain alkylcarboxylate (Alkyl-COOR) is selected from linear or branched Alkyl groups having 6 to 30 carbons, and R is selected from methyl or ethyl.
5. The preparation method of polyethylene glycol long-chain alkylamide according to claim 1, wherein the mass ratio of the silicon dioxide to the mPEG is 0.2-0.5: 1.
6. the preparation method of polyethylene glycol long-chain alkylamide according to claim 1, wherein the mass ratio of the alumina to the mPEG is 1-1.5: 1.
7. the method of claim 1, wherein the ammonia gas used in the first step is at a pressure of 2 to 5 atmospheres.
8. The preparation method of the polyethylene glycol long-chain alkylamide according to claim 1, wherein in the second step, the mass ratio of the long-chain alkyl carboxylic ester to the polyethylene glycol amine monomethyl ether is 1-1.2: 1.
9. the method for preparing polyethylene glycol long-chain alkylamide according to claim 1, wherein the reaction temperature in the first step is 160-200 ℃ and the reaction temperature in the second step is 150-180 ℃.
10. Use of a polyethylene glycol long chain alkylamide according to any of claims 1-9 in a lubricant.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201911068446.7A CN110982061A (en) | 2019-11-05 | 2019-11-05 | Preparation method and application of polyethylene glycol long-chain alkylamide |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201911068446.7A CN110982061A (en) | 2019-11-05 | 2019-11-05 | Preparation method and application of polyethylene glycol long-chain alkylamide |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5766612A (en) * | 1993-10-22 | 1998-06-16 | Basf Aktiengesellschaft | Use of endgroup-capped fatty amide alkoxylates |
| CN103361151A (en) * | 2013-07-26 | 2013-10-23 | 上海金兆节能科技有限公司 | Lubricant composite, preparation method thereof and trace lubricant made of same |
| CN106905149A (en) * | 2017-02-10 | 2017-06-30 | 上海金兆节能科技有限公司 | Polyethylene glycol isomery alcohol ester and preparation method thereof and prepare environmentally friendly micro lubricating agent with the ester |
-
2019
- 2019-11-05 CN CN201911068446.7A patent/CN110982061A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5766612A (en) * | 1993-10-22 | 1998-06-16 | Basf Aktiengesellschaft | Use of endgroup-capped fatty amide alkoxylates |
| CN103361151A (en) * | 2013-07-26 | 2013-10-23 | 上海金兆节能科技有限公司 | Lubricant composite, preparation method thereof and trace lubricant made of same |
| CN106905149A (en) * | 2017-02-10 | 2017-06-30 | 上海金兆节能科技有限公司 | Polyethylene glycol isomery alcohol ester and preparation method thereof and prepare environmentally friendly micro lubricating agent with the ester |
Non-Patent Citations (1)
| Title |
|---|
| 屈撑囤等: "《精细有机合成反应与工艺》", 30 September 2000, 西北大学出版社 * |
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