CN102633661A - Method for preparing 1-[di-(2-hydroxyethyl)amino]-3-cardanol oxyisopropanol by one-pot process - Google Patents
Method for preparing 1-[di-(2-hydroxyethyl)amino]-3-cardanol oxyisopropanol by one-pot process Download PDFInfo
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- CN102633661A CN102633661A CN2012100863030A CN201210086303A CN102633661A CN 102633661 A CN102633661 A CN 102633661A CN 2012100863030 A CN2012100863030 A CN 2012100863030A CN 201210086303 A CN201210086303 A CN 201210086303A CN 102633661 A CN102633661 A CN 102633661A
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Abstract
The invention relates to a preparation method of cardanol oxyisopropanol, particularly a method for preparing 1-[di-(2-hydroxyethyl)amino]-3-cardanol oxyisopropanol by a one-pot process. The invention aims to solve the problems of low yield, complex operation and high emulsification tendency in the existing method for preparing 1-[di-(2-hydroxyethyl)amino]-3-cardanol oxyisopropanol. The method comprises the following steps: 1. preparing sodium cardanol; 2. adding [2,3]-(3-hydroxy-2-nitrogen)hydrindone-18-crown-6 and epoxy chloropropane to obtain a pre-reaction product; 3. adding diethanolamine to obtain a final reaction product; and 4. purifying sequentially by a rotary evaporation method, water-ethanol mixed solvent washing and silicagel column chromatography to obtain the fine 1-[di-(2-hydroxyethyl)amino]-3-cardanol oxyisopropanol product. The invention is mainly used for preparing the 1-[di-(2-hydroxyethyl)amino]-3-cardanol oxyisopropanol.
Description
Technical field
The present invention relates to a kind of preparation method of cardanol oxygen base Virahol.
Background technology
Cardanol is the cashew nut main body of oil, in cashew nut oil, contains 90%, is good sustainable biomass resource; Because of containing the structure and the unsaturated terminal chain of phenol in its structure; Therefore can derive many compounds, substitute macromolecular materials such as petroleum products production of phenol resol and urethane, be widely used in fields such as automobile, electronics, building, boats and ships with special purpose; Be eco-friendly biomaterial, on scientific research and industrial production, have crucial meaning.Polyol is the material that must not lack in the preparation polyurethane products.Utilize cardanol to synthesize 1-[two-(2-hydroxyethyl) amino]-3-cardanol oxygen base Virahol, this is the polyol that contains three hydroxyls, can be used for preparing macromolecular materials such as urethane.The method that in the past prepared this material in two steps, the first step is a preparation cardanol epoxy propyl ether, reaction is in the presence of Zinc Chloride Anhydrous, cardanol and epichlorohydrin reaction under alkaline condition.Second step was that the reaction of cardanol epoxy propyl ether and diethylolamine obtains 1-[two-(2-hydroxyethyl) amino]-3-cardanol oxygen base Virahol under the neutrallty condition, and two go on foot overall yields 56%.This method is easy to generate emulsion, reduces productive rate, and midbody separates will pass through abstraction purification process, complex operation.Therefore there is low, the complicated operation of productive rate in the existing method for preparing 1-[two-(2-hydroxyethyl) amino]-3-cardanol oxygen base Virahol, and is easy to generate the problem of emulsion.
Summary of the invention
The present invention will solve the existing method for preparing 1-[two-(2-hydroxyethyl) amino]-3-cardanol oxygen base Virahol and have low, the complicated operation of productive rate; And be easy to generate the problem of emulsion, and provide a kind of one kettle way to prepare the method for 1-[two-(2-hydroxyethyl) amino]-3-cardanol oxygen base Virahol.
One kettle way prepares the method for 1-[two-(2-hydroxyethyl) amino]-3-cardanol oxygen base Virahol; Specifically accomplish according to the following steps: one, at first cardanol is added in the aqueous sodium hydroxide solution of mass concentration 20%～40%; And be heated to 70 ℃～100 ℃ from room temperature; Low whipping speed is that 800 commentaries on classics/min～1200 commentaries on classics/min, temperature are 70 ℃～100 ℃ reaction 1h～3h down then, obtains cardanol sodium; Two, in the cardanol sodium that step 1 obtains, add [2 successively; 3]-(3-hydroxyl-2-nitrogen) indone and 18-hat-6 and epoxy chloropropane; And low whipping speed is that 800 commentaries on classics/min～1200 commentaries on classics/min, temperature are 80 ℃～120 ℃ down reaction 3h～6h, obtains the pre-reaction product; Three, the pre-reaction product that at first step 2 is obtained is cooled to room temperature; And adopt Hydrogen chloride that cooled pre-reaction product pH regulator is extremely neutral; Be heated to 50 ℃～90 ℃ from room temperature then; And dropwise adding diethylolamine, low whipping speed is that 800 commentaries on classics/min～1200 commentaries on classics/min, temperature are 50 ℃～90 ℃ reaction 4h～8h down, obtains final reacting product; Four, the final reacting product that earlier step 3 is obtained is cooled to room temperature; Then till 40 ℃～60 ℃ prolong absence of liq that adopt the rotary evaporation method to be concentrated into Rotary Evaporators down distillate; Obtain brown thick product; Adopt water-ethanol mixed solvent to wash brown thick product 3～5 times; Obtain brown 1-[two-(2-hydroxyethyl) amino]-3-cardanol oxygen base Virahol bullion, adopt silica gel column chromatography to purify at last, promptly obtain 1-[two-(2-hydroxyethyl) amino]-3-cardanol oxygen base Virahol elaboration; The ratio of the aqueous sodium hydroxide solution volume of cardanol quality described in the step 1 and mass concentration 20%～40% is (50g～70g): 100mL; [2,3] that add described in the step 2-(3-hydroxyl-2-nitrogen) indone and 18-hat-6 are 1 with the mass ratio of the cardanol described in the step 1: (14～16); The epoxy chloropropane that adds described in the step 2 and the mol ratio of the cardanol described in the step 1 are (0.9～1.1): 1; The diethylolamine that adds described in the step 3 and the mol ratio of the cardanol described in the step 1 are (0.9～1.1): 1.
Advantage of the present invention: one, the present invention adopts one kettle way to synthesize 1-[two-(2-hydroxyethyl) amino]-3-cardanol oxygen base Virahol, has simplified reactions step, and is simple to operate; Two, the present invention adopts [2; 3]-(3-hydroxyl-2-nitrogen) indone and 18-hat-6 is as phase-transfer catalyst; Improved the ultimate yield of 1-[two-(2-hydroxyethyl) amino]-3-cardanol oxygen base Virahol; Ultimate yield is 85%～90%, prepares 1-[two-(2-hydroxyethyl) amino]-3-cardanol oxygen base Virahol with the existing method of fractional steps and compares and improved 29%～34%.
Description of drawings
Fig. 1 is the hydrogen nuclear magnetic resonance spectrogram of test one preparation 1-[two-(2-hydroxyethyl) amino]-3-cardanol oxygen base Virahol elaboration.
Embodiment
Embodiment one: this embodiment is the method that one kettle way prepares 1-[two-(2-hydroxyethyl) amino]-3-cardanol oxygen base Virahol, specifically accomplishes according to the following steps:
One, at first cardanol is added in the aqueous sodium hydroxide solution of mass concentration 20%～40%; And be heated to 70 ℃～100 ℃ from room temperature; Low whipping speed is that 800 commentaries on classics/min～1200 commentaries on classics/min, temperature are 70 ℃～100 ℃ reaction 1h～3h down then, obtains cardanol sodium; Two, in the cardanol sodium that step 1 obtains, add [2 successively; 3]-(3-hydroxyl-2-nitrogen) indone and 18-hat-6 and epoxy chloropropane; And low whipping speed is that 800 commentaries on classics/min～1200 commentaries on classics/min, temperature are 80 ℃～120 ℃ down reaction 3h～6h, obtains the pre-reaction product; Three, the pre-reaction product that at first step 2 is obtained is cooled to room temperature; And adopt Hydrogen chloride that cooled pre-reaction product pH regulator is extremely neutral; Be heated to 50 ℃～90 ℃ from room temperature then; And dropwise adding diethylolamine, low whipping speed is that 800 commentaries on classics/min～1200 commentaries on classics/min, temperature are 50 ℃～90 ℃ reaction 4h～8h down, obtains final reacting product; Four, the final reacting product that earlier step 3 is obtained is cooled to room temperature; Then till 40 ℃～60 ℃ prolong absence of liq that adopt the rotary evaporation method to be concentrated into Rotary Evaporators down distillate; Obtain brown thick product; Adopt water-ethanol mixed solvent to wash brown thick product 3～5 times; Obtain brown 1-[two-(2-hydroxyethyl) amino]-3-cardanol oxygen base Virahol bullion, adopt silica gel column chromatography to purify at last, promptly obtain 1-[two-(2-hydroxyethyl) amino]-3-cardanol oxygen base Virahol elaboration.
The ratio of the aqueous sodium hydroxide solution volume of cardanol quality described in this embodiment step 1 and mass concentration 20%～40% is (50g～70g): 100mL.
[2,3] that add described in this embodiment step 2-(3-hydroxyl-2-nitrogen) indone and 18-hat-6 are 1 with the mass ratio of the cardanol described in the step 1: (14～16); The epoxy chloropropane that adds described in this embodiment step 2 and the mol ratio of the cardanol described in the step 1 are (0.9～1.1): 1,
The diethylolamine that adds described in this embodiment step 3 and the mol ratio of the cardanol described in the step 1 are (0.9～1.1): 1.
This embodiment adopts the synthetic 1-[two-(2-hydroxyethyl) amino] of one kettle way-3-cardanol oxygen base Virahol, has simplified reactions step, and is simple to operate.
This embodiment adopts [2; 3]-(3-hydroxyl-2-nitrogen) indone and 18-hat-6 is as phase-transfer catalyst; Improved the ultimate yield of 1-[two-(2-hydroxyethyl) amino]-3-cardanol oxygen base Virahol; Ultimate yield is 85%～90%, prepares 1-[two-(2-hydroxyethyl) amino]-3-cardanol oxygen base Virahol with the existing method of fractional steps and compares and improved 29%～34%.
Embodiment two; This embodiment with the difference of embodiment one is: be heated to 90 ℃～98 ℃ from room temperature in the step 1; Low whipping speed is that 900 commentaries on classics/min～1100 commentaries on classics/min, temperature are 90 ℃～98 ℃ reaction 1.5h～2.5h down then, obtains cardanol sodium.Other is identical with embodiment one.
Embodiment three: this embodiment with one of embodiment one or two difference is: low whipping speed is that 900 commentaries on classics/min～1100 commentaries on classics/min, temperature are 90 ℃～110 ℃ reaction 3.5h～4.5h down in the step 2, obtains the pre-reaction product.Other is identical with embodiment one or two.
Embodiment four: this embodiment with one of embodiment one to three difference is: be heated to 60 ℃～80 ℃ from room temperature in the step 3; And dropwise add diethylolamine; Low whipping speed is that 900 commentaries on classics/min～1100 commentaries on classics/min, temperature are 60 ℃～80 ℃ reaction 5h～7h down, obtains final reacting product.Other is identical with embodiment one to three.
Adopt following verification experimental verification effect of the present invention:
Test one: one kettle way prepares the method for 1-[two-(2-hydroxyethyl) amino]-3-cardanol oxygen base Virahol, specifically accomplishes according to the following steps:
One, at first cardanol is added in the aqueous sodium hydroxide solution of mass concentration 30%, and be heated to 95 ℃ from room temperature, low whipping speed is that 1000 commentaries on classics/min, temperature are 95 ℃ of reaction 2h down then, obtains cardanol sodium; Two, in the cardanol sodium that step 1 obtains, add [2,3]-(3-hydroxyl-2-nitrogen) indone and 18-hat-6 and epoxy chloropropane successively, and low whipping speed is that 1000 commentariess on classics/min, temperature are 100 ℃ and react 4h down, obtains the pre-reaction product; Three, the pre-reaction product that at first step 2 is obtained is cooled to room temperature; And adopt Hydrogen chloride that cooled pre-reaction product pH regulator is extremely neutral; Be heated to 70 ℃ from room temperature then; And dropwise adding diethylolamine, low whipping speed is that 1000 commentaries on classics/min, temperature are 70 ℃ of reaction 6h down, obtains final reacting product; Four, the final reacting product that earlier step 3 is obtained is cooled to room temperature; Then till 50 ℃ of prolong absence of liq that adopt the rotary evaporation method to be concentrated into Rotary Evaporators down distillate; Obtain brown thick product; Adopt water-ethanol mixed solvent to wash brown thick product 4 times; Obtain brown 1-[two-(2-hydroxyethyl) amino]-3-cardanol oxygen base Virahol bullion, adopt silica gel column chromatography to purify at last, promptly obtain 1-[two-(2-hydroxyethyl) amino]-3-cardanol oxygen base Virahol elaboration.
The ratio of the aqueous sodium hydroxide solution volume of cardanol quality described in this testing sequence one and mass concentration 20%～40% is 59.7g: 100mL.
The mass ratio of the cardanol described in [2,3]-(3-hydroxyl-2-nitrogen) indone that adds described in this testing sequence two and 18-hat-6 and the step 14: 59.7; The epoxy chloropropane that adds described in this testing sequence two and the mol ratio of the cardanol described in the step 1 are 1: 1.
The diethylolamine that adds described in this testing sequence three and the mol ratio of the cardanol described in the step 1 are 1: 1.
[2,3] described in this testing sequence two-(3-hydroxyl-2-nitrogen) indone and 18-hat the-6th, the method that provides according to patent " closing of cardanol epoxy propyl ether " prepares, and the application number of this patent is: CN201010558619.6.
Calculate and to know through product; The productive rate that this test finally obtains 1-[two-(2-hydroxyethyl) amino]-3-cardanol oxygen base Virahol elaboration is 88%, prepares 1-[two-(2-hydroxyethyl) amino]-3-cardanol oxygen base Virahol with the existing method of fractional steps and compares and improved 32%.
Adopt NMR to detect 1-[two-(2-hydroxyethyl) the amino]-3-cardanol oxygen base Virahol elaboration of this test preparation, the hydrogen nuclear magnetic resonance spectrogram that obtains is as shown in Figure 1, and detected result is:
1HNMR (CDCl
3) δ: 0.88 (m broad 2H), 1.3 (sbroad, 12H), 1.6 (s broad, 2H), 2.1 (s broad; 2H), 2.6～2.8 (m, 8H), 3.6 (d broad, 4H), 3.8 (t broatd; 4H), 3.9 (d broad, 2H), 4.1 (d, 2H), 4.7 (s broad; 1H), 5.5 (m, 3H), 6.7～7.3 (m, 4H).
But the structure through magnetic resonance detection knowledge capital test synthetic 1-[two-(2-hydroxyethyl) amino]-3-cardanol oxygen base Virahol is
Claims (5)
1. one kettle way prepares the method for 1-[two-(2-hydroxyethyl) amino]-3-cardanol oxygen base Virahol, it is characterized in that one kettle way prepares 1-[two-(2-hydroxyethyl) amino]-3-cardanol oxygen base Virahol and accomplishes according to the following steps:
One, at first cardanol is added in the aqueous sodium hydroxide solution of mass concentration 20%～40%; And be heated to 70 ℃～100 ℃ from room temperature; Low whipping speed is that 800 commentaries on classics/min～1200 commentaries on classics/min, temperature are 70 ℃～100 ℃ reaction 1h～3h down then, obtains cardanol sodium; Two, in the cardanol sodium that step 1 obtains, add [2 successively; 3]-(3-hydroxyl-2-nitrogen) indone and 18-hat-6 and epoxy chloropropane; And low whipping speed is that 800 commentaries on classics/min～1200 commentaries on classics/min, temperature are 80 ℃～120 ℃ down reaction 3h～6h, obtains the pre-reaction product; Three, the pre-reaction product that at first step 2 is obtained is cooled to room temperature; And adopt Hydrogen chloride that cooled pre-reaction product pH regulator is extremely neutral; Be heated to 50 ℃～90 ℃ from room temperature then; And dropwise adding diethylolamine, low whipping speed is that 800 commentaries on classics/min～1200 commentaries on classics/min, temperature are 50 ℃～90 ℃ reaction 4h～8h down, obtains final reacting product; Four, the final reacting product that earlier step 3 is obtained is cooled to room temperature; Then till 40 ℃～60 ℃ prolong absence of liq that adopt the rotary evaporation method to be concentrated into Rotary Evaporators down distillate; Obtain brown thick product; Adopt water-ethanol mixed solvent to wash brown thick product 3～5 times; Obtain brown 1-[two-(2-hydroxyethyl) amino]-3-cardanol oxygen base Virahol bullion, adopt silica gel column chromatography to purify at last, promptly obtain 1-[two-(2-hydroxyethyl) amino]-3-cardanol oxygen base Virahol elaboration; The ratio of the aqueous sodium hydroxide solution volume of cardanol quality described in the step 1 and mass concentration 20%～40% is (50g～70g): 100mL; [2,3] that add described in the step 2-(3-hydroxyl-2-nitrogen) indone and 18-hat-6 are 1 with the mass ratio of the cardanol described in the step 1: (14～16); The epoxy chloropropane that adds described in the step 2 and the mol ratio of the cardanol described in the step 1 are (0.9～1.1): 1; The diethylolamine that adds described in the step 3 and the mol ratio of the cardanol described in the step 1 are (0.9～1.1): 1.
2. one kettle way according to claim 1 prepares the method for 1-[two-(2-hydroxyethyl) amino]-3-cardanol oxygen base Virahol; It is characterized in that being heated to 90 ℃～98 ℃ from room temperature in the step 1; Low whipping speed is that 900 commentaries on classics/min～1100 commentaries on classics/min, temperature are 90 ℃～98 ℃ reaction 1.5h～2.5h down then, obtains cardanol sodium.
3. one kettle way according to claim 2 prepares the method for 1-[two-(2-hydroxyethyl) amino]-3-cardanol oxygen base Virahol; It is characterized in that low whipping speed is that 900 commentaries on classics/min～1100 commentaries on classics/min, temperature are 90 ℃～110 ℃ reaction 3.5h～4.5h down in the step 2, obtain the pre-reaction product.
4. one kettle way according to claim 3 prepares the method for 1-[two-(2-hydroxyethyl) amino]-3-cardanol oxygen base Virahol; It is characterized in that being heated to 60 ℃～80 ℃ from room temperature in the step 3; And dropwise add diethylolamine; Low whipping speed is that 900 commentaries on classics/min～1100 commentaries on classics/min, temperature are 60 ℃～80 ℃ reaction 5h～7h down, obtains final reacting product.
5. the method for preparing 1-[two-(2-hydroxyethyl) amino]-3-cardanol oxygen base Virahol according to claim 1,2,3 or 4 described one kettle ways; It is characterized in that the water-ethanol mixed solvent described in the step 4 is mixed by deionized water and absolute ethyl alcohol, and the volume ratio of described deionized water and absolute ethyl alcohol is (0.5～1.5): 1.
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| WO2015090442A1 (en) * | 2013-12-20 | 2015-06-25 | Basf Coatings Gmbh | Aqueous primary dispersions, method for producing same, and use thereof |
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Application publication date: 20120815 |