CN102633671A - Method for preparing n-undecarbamide diacid - Google Patents
Method for preparing n-undecarbamide diacid Download PDFInfo
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- CN102633671A CN102633671A CN2012101084221A CN201210108422A CN102633671A CN 102633671 A CN102633671 A CN 102633671A CN 2012101084221 A CN2012101084221 A CN 2012101084221A CN 201210108422 A CN201210108422 A CN 201210108422A CN 102633671 A CN102633671 A CN 102633671A
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- diacid
- undecanoyl
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Abstract
The invention discloses a method for preparing n-undecarbamide diacid. Water-soluble fatty acid derivative antirust additives have predominant advantages, and are important additives for water-based metalworking fluid. Compared with the conventional antirust additives, the method for preparing n-undecarbamide diacid is characterized in that n-undecarbamide diacid is equivalent to long-chain n-tribasic carboxylic acid; and the water solubility and the emulsifying performance are enhanced in the presence of amido compared with the similar tribasic organic carboxylic acid, and n-undecarbamide diacid has obvious performance advantages.
Description
Technical field
The present invention relates to the organic chemistry synthesis technical field, refer to a kind of preparation method of positive undecanoyl diamide diacid especially.
Background technology
Water-based metal working fluid has obtained fast development because of having advantages such as good cooling property, cleaning, rust-preventing characteristic, economy and security, and is widely used in metal manufacture fields such as cutting, grinding, calendering, punching press and tapping,
Long-chain biatomic acid is meant the straight-chain dicarboxylic acid of containing 10 above carbon atoms, is important fine chemical material, and long-chain biatomic acid is non-existent at nature; At present, the U.S., Germany, Japan produce long-chain biatomic acid and mainly utilize chemical synthesis, but its synthesis condition is harsh; Yield is low; Cost is high, and environmental pollution is serious, and can only produce SL-AH.
The country that the present really unique using microbe fermentation technique of China is realized multiple long carbochain biatomic acid large-scale industrial production; Intracellular enzyme through mikrobe synthesizes long-chain biatomic acid with NPH catalysis; This process is accomplished in intracellular microsome; NPH with in the light wax of petroleum by-product oil is a raw material, and the incomparable meliority of chemical synthesis process is arranged, and its state of the art and industry size all are in the first place in the world.
Water-soluble grease pipecolic acid derivative class rust-inhibiting additive has outstanding advantage, is one type of important additives of water-based metal working fluid, and at first the raw material synthesis technique of water-soluble grease pipecolic acid derivative class rust-inhibiting additive is ripe, for suitability for industrialized production provides condition; Secondly, the derivative of fatty acid class rust-inhibiting additive of different chain length has different antirust selectivity, is the water-soluble anti-rust additive that has more industrial practice to use at present; Its three, China's using microbe fermentation technique is realized the large-scale production of multiple long carbochain biatomic acid, also makes to utilize positive 11 carbon dicarboxylic anhydrides to become possibility for the synthetic positive undecanoyl diamide diacid of raw material.
Compare with traditional rust-inhibiting additive, positive undecanoyl diamide diacid is equivalent to positive long-chain tribasic carboxylic acid, because the existence of carboxamido-group has strengthened water-soluble and emulsifying property than similar ternary organic carboxyl acid again, feature performance benefit is obvious.
Summary of the invention
The preparation method of a kind of positive undecanoyl diamide diacid of the present invention; It is characterized in that, overcome the deficiency of prior art, utilize the molecular designing viewpoint; To have water miscible hydrophilic radical and have butyrous adsorptivity group and gather in an intramolecularly; Synthetic a kind of rust-preventing characteristic is equivalent to tribasic carboxylic acid, has good rustless property, has concurrently water-soluble and water-based metal working fluid additive emulsifying property.
To achieve these goals; Technical solution of the present invention is: positive 11 carbon dicarboxylic anhydrides and hexanolactam microwave heating reaction; The intermediate product that its reaction generates is hydrolyzed under alkaline condition, under acidic conditions, carries out acid out afterwards; Obtain positive undecanoyl diamide diacid after filtering, washing, specifically comprise following steps:
1). positive 11 carbon dicarboxylic anhydrides (I) and hexanolactam (II) are outstanding to be mixed in xylene solvent, under catalyst action, in 110
℃～140
℃Behind following microwave heating reaction 4～6h, air distillation goes out organic solvent and catalyzer, obtains intermediate product (III), and its main chemical reactions is:
Further be, described catalyzer is selected from the liquid organic bases, and particular methanol sodium and sodium ethylate, its consumption are 0.1%～1.5% of positive 11 carbon dicarboxylic anhydride consumptions.
Its consumption of described YLENE is 1～3 times of positive 11 carbon dicarboxylic anhydride consumptions.
The mol ratio of described hexanolactam and positive 11 carbon dicarboxylic acid acid anhydrides is 1 : 1～1.2.
2). intermediate product (III) in 20～50 ℃ of reaction 1～3h that are hydrolyzed, filters in the presence of alkali, gets filtrating, can get positive undecanoyl diamide diacid salt (IV), and its main chemical reactions is:
Further be the X in described positive undecanoyl diamide diacid salt (IV) structural formula
1And X
2Be K or Na.
Described alkali is selected from carbonate or the sodium hydroxide of sodium and potassium, in the Pottasium Hydroxide one or more.
3). positive undecanoyl diamide diacid salt (IV) carries out acid out under acidic conditions, obtain positive long-chain carbon alkane diamide two caproic acids (V) after filtering, washing, and its main chemical reactions is:
Further be that described acid usefulness acid is selected from one or more in acetic acid, hydrochloric acid and the sulfuric acid.
Embodiment
Embodiment 1
In whipping appts, reflux exchanger and TM there-necked flask were housed, adding 200 gram positive 11 carbon dicarboxylic anhydrides and 110 are restrained oneself, and lactan is outstanding to be mixed in 300 gram xylene solvents, under 3 gram sodium ethylate catalyst actions, in 110
℃～120
℃Behind the following microwave heating reaction 4h, air distillation goes out organic solvent YLENE; In the there-necked flask that reactant is housed, add 20% KOH solution, in 20～50 ℃ of reaction 1～3h that are hydrolyzed, until the pH value of solution value stabilization be 9～10 and no longer change till, filter, get filtrating, can get positive undecanoyl diamide diacid potassium solution; In positive undecanoyl diamide diacid potassium solution, add 60% sulfuric acid, until the pH value of solution value stabilization be 2～3 and no longer change till, leave standstill, filter, obtain positive undecanoyl diamide diacid after the washing.
Embodiment 2
In whipping appts, reflux exchanger and TM there-necked flask were housed, adding 230 gram positive 11 carbon dicarboxylic anhydrides and 120 are restrained oneself, and lactan is outstanding to be mixed in 400 gram xylene solvents, under 2 gram sodium methoxide catalyst effects, in 120
℃～130
℃Behind the following microwave heating reaction 5h, air distillation goes out organic solvent YLENE; In the there-necked flask that reactant is housed, add 20% KOH solution, in 20～50 ℃ of reaction 1～3h that are hydrolyzed, until the pH value of solution value stabilization be 9～10 and no longer change till, filter, get filtrating, can get positive undecanoyl diamide diacid and receive solution; In positive undecanoyl diamide diacid sodium solution, add 35% hydrochloric acid, until the pH value of solution value stabilization be 2～3 and no longer change till, leave standstill, filter, obtain positive undecanoyl diamide diacid after the washing.
The above; Embodiment only is that preferred implementation of the present invention is described; Be not that scope of the present invention is limited; Under the prerequisite of the spirit that does not break away from the present invention's technology, various distortion and improvement that this area engineering technical personnel make technical scheme of the present invention all should fall in the definite protection domain of claims of the present invention.
Claims (3)
1. the preparation method of a kind of positive undecanoyl diamide diacid of the present invention; It is characterized in that: positive 11 carbon dicarboxylic anhydrides and hexanolactam microwave heating reaction; The intermediate product that its reaction generates is hydrolyzed under alkaline condition, under acidic conditions, carries out acid out afterwards; Obtain positive undecanoyl diamide diacid after filtering, washing, specifically comprise following steps:
1), be the branch aqua with toluene, equimolar 6-chlorine caproic acid and methyl alcohol are under 80 ℃～90 ℃, back flow reaction 3～5h generates 6-chlorine methyl caproate,
2), be solvent with toluene, 6-chlorine methyl caproate and trimeric cyanamide in the presence of alkali, in 110～120 ℃ of reaction 4～6h, generate intermediate compound;
3), intermediate compound in the presence of alkali, in 80～100 ℃ of hydrolysis reaction 5～7h, after standing separation goes out water, filter, through after acid out, washing and the drying, can get the nitrogen heterocyclic ring hexosamine.
2. the preparation method of a kind of positive undecanoyl diamide diacid according to claim 1 is characterized in that: the mol ratio of described hexanolactam and positive 11 carbon dicarboxylic acid acid anhydrides is 1 : 1～1.2.
3. the preparation method of a kind of positive undecanoyl diamide diacid according to claim 1 is characterized in that: described acid usefulness acid is selected from one or more in acetic acid, hydrochloric acid and the sulfuric acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012101084221A CN102633671A (en) | 2012-04-14 | 2012-04-14 | Method for preparing n-undecarbamide diacid |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012101084221A CN102633671A (en) | 2012-04-14 | 2012-04-14 | Method for preparing n-undecarbamide diacid |
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| CN102633671A true CN102633671A (en) | 2012-08-15 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111040827A (en) * | 2019-12-11 | 2020-04-21 | 富兰克润滑科技（太仓）有限公司 | Organic carboxylic acid compound, preparation method and steel plate water-based processing fluid |
-
2012
- 2012-04-14 CN CN2012101084221A patent/CN102633671A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111040827A (en) * | 2019-12-11 | 2020-04-21 | 富兰克润滑科技（太仓）有限公司 | Organic carboxylic acid compound, preparation method and steel plate water-based processing fluid |
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Application publication date: 20120815 |