CN117229122A - Method for preparing jojoba alcohol from jojoba oil - Google Patents
Method for preparing jojoba alcohol from jojoba oil Download PDFInfo
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- CN117229122A CN117229122A CN202311033029.5A CN202311033029A CN117229122A CN 117229122 A CN117229122 A CN 117229122A CN 202311033029 A CN202311033029 A CN 202311033029A CN 117229122 A CN117229122 A CN 117229122A
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- jojoba
- jojoba oil
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 95
- 229940119170 jojoba wax Drugs 0.000 title claims abstract description 51
- 241000221095 Simmondsia Species 0.000 title claims abstract description 36
- 235000004433 Simmondsia californica Nutrition 0.000 title claims abstract description 36
- 238000000034 method Methods 0.000 title claims abstract description 20
- 239000003054 catalyst Substances 0.000 claims abstract description 54
- 238000006243 chemical reaction Methods 0.000 claims abstract description 41
- 150000002191 fatty alcohols Chemical class 0.000 claims abstract description 26
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 24
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 19
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims abstract description 16
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims abstract description 16
- 239000000047 product Substances 0.000 claims abstract description 12
- 239000002994 raw material Substances 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 42
- 238000003756 stirring Methods 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 30
- 239000011347 resin Substances 0.000 claims description 29
- 229920005989 resin Polymers 0.000 claims description 29
- 238000004821 distillation Methods 0.000 claims description 28
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 24
- 239000008367 deionised water Substances 0.000 claims description 22
- 229910021641 deionized water Inorganic materials 0.000 claims description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
- 239000003463 adsorbent Substances 0.000 claims description 20
- 238000005406 washing Methods 0.000 claims description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 238000010438 heat treatment Methods 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 15
- 238000001816 cooling Methods 0.000 claims description 14
- 238000001035 drying Methods 0.000 claims description 14
- 239000000725 suspension Substances 0.000 claims description 10
- 238000001179 sorption measurement Methods 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 8
- 230000004913 activation Effects 0.000 claims description 7
- 239000003480 eluent Substances 0.000 claims description 7
- 239000000706 filtrate Substances 0.000 claims description 7
- 238000011068 loading method Methods 0.000 claims description 7
- 238000007789 sealing Methods 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 5
- 238000005303 weighing Methods 0.000 claims description 5
- 239000012295 chemical reaction liquid Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 239000012279 sodium borohydride Substances 0.000 claims description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- 235000014113 dietary fatty acids Nutrition 0.000 abstract description 9
- 229930195729 fatty acid Natural products 0.000 abstract description 9
- 239000000194 fatty acid Substances 0.000 abstract description 9
- 150000004665 fatty acids Chemical class 0.000 abstract description 9
- 239000012043 crude product Substances 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 21
- 238000006722 reduction reaction Methods 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000012018 catalyst precursor Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 230000003020 moisturizing effect Effects 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 238000002604 ultrasonography Methods 0.000 description 2
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- 229920000832 Cutin Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 210000002374 sebum Anatomy 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
Abstract
The invention discloses a method for preparing joba alcohol from jojoba oil, which comprises the steps of utilizing hydrogen and a catalyst to decompose the jojoba oil into fatty acid and fatty alcohol with high efficiency, utilizing three-stage rectification treatment to separate the fatty acid and the fatty alcohol, and finally purifying a crude product of the fatty alcohol, wherein the raw materials of the catalyst comprise the following components in percentage: 15-30% of nickel powder, 18-29% of cobalt powder, 2-6% of platinum dioxide, 10-25% of ferric chloride and 25-40% of a reducing agent, and the purity of the jojoba alcohol product prepared by the method can reach more than 90%, so that high conversion rate relative to jojoba oil can be realized.
Description
Technical Field
The invention relates to the technical field of alcohol preparation, in particular to a method for preparing jojoba alcohol from jojoba oil.
Background
The jojoba oil is an ester substance prepared by grinding, extracting and purifying seeds of shrub jojoba in mexico and esterifying the seeds, is stable and not easy to oxidize, has the effects of supplementing skin sebum and balancing skin moisture loss, can soften skin cutin, enables the skin to keep soft, elastic and in a natural moisturizing state for a long time, and can also ease the skin and improve the skin sensitivity problem. Jojoba oil also contains a large amount of fatty acids and fatty alcohols, of which jojoba alcohol is an important ingredient.
However, jojoba oil is a long-chain unsaturated acid ester, has a relatively high molecular weight, a relatively low skin penetration rate, a relatively poor penetration rate, and a relatively short duration of skin moisturizing effect, and therefore, an efficient preparation method is needed to extract jojoba oil from jojoba alcohol.
Disclosure of Invention
The present invention provides a process for the preparation of jojoba alcohol from jojoba oil, which process enables high conversion rates and the preparation of very high purity jojoba alcohol.
The invention solves the technical problems by adopting the following technical scheme:
a process for the preparation of jojoba alcohol from jojoba oil, comprising the steps of:
s1, adding jojoba oil and propanol into a reaction kettle, and heating to 65-75 ℃ under the condition of stirring and refluxing for reaction for 2-5 hours; the addition amount of the propanol is 50-60% of the mass of jojoba oil, and the mass fraction of the propanol is 60-70%;
s2, adding a catalyst into the reaction liquid in the step S1 for reduction and activation treatment, sealing the kettle, using high-purity nitrogen or hydrogen to replace air in the kettle, then introducing hydrogen to the reaction pressure of 3.0-6.0 MPa, heating to 150-200 ℃, starting stirring reaction at the stirring speed of 1000-1500 r/min for 6-12 h, cooling, and filtering to obtain a mixture;
s3, carrying out three-stage rectification on the mixture in the step S2 through a packed rectifying tower, and introducing filtrate into a first rectifying tower for rectification, wherein the operation temperature of the tower top is 100-110 ℃, and the vacuum degree of the tower top is 1.0-2.0 KPa; introducing the residue at the bottom of the first rectifying tower into a second rectifying tower for rectifying, wherein the operation temperature of the tower top is 150-180 ℃, and the vacuum degree of the tower top is 2.0-3.0 KPa; introducing the second distillation column fraction into a third distillation column for distillation, wherein the operation temperature of the top of the third distillation column is 200-250 ℃, and the vacuum degree of the top of the third distillation column is 3.0-4.0 KPa; cooling to obtain crude fatty alcohol;
s4, extracting the crude fatty alcohol product with ethyl acetate for 2-4 times, each time for 2-3 hours, concentrating the extract to 1.2-1.5 g/ml at 40-60 ℃ and dissolving the extract in ethanol with the mass concentration of 70%; loading the extract solution on macroporous adsorption resin, eluting with deionized water at the eluting speed of 2-2.5 BV/h, collecting water eluate, discarding the water eluate, desorbing with 80-90% ethanol, and collecting eluate;
and S5, washing the eluent in the step S4 with 20-30% acetone for 1-3 times, and drying at 50-60 ℃ until the weight is constant, thus obtaining the jojoba alcohol.
Preferably, the flow rate of macroporous adsorption resin on the extract solution in the step S4 is 1.5-2 mL/min.
Preferably, in the step S4, the mass of deionized water is 5-8 times that of the macroporous adsorption resin, and the mass of ethanol is 1.5-5 times that of the macroporous adsorption resin.
Preferably, the macroporous adsorbent resin is selected from HPD-100, HPD-750, HPD-826, and HPD-750 is more preferred.
Preferably, the catalyst comprises the following components in weight percent: 15-30% of nickel powder, 18-29% of cobalt powder, 2-6% of platinum dioxide, 10-25% of ferric chloride and 25-40% of a reducing agent.
Preferably, the catalyst raw material comprises the following components in percentage by weight: 22% of nickel powder, 24% of cobalt powder, 4% of platinum dioxide, 17% of ferric chloride and 33% of a reducing agent.
The catalyst provided by the invention can further improve the performance of the catalyst and reduce the consumption of noble metals by introducing transition metal iron; active components nickel and cobalt are fully loaded on a platinum dioxide carrier through ultrasound, so that the catalytic property of the catalyst can be effectively improved, and the reduction reaction efficiency is higher; the reasonable active component ratio in the catalyst can effectively improve the catalytic activity of the catalyst and increase the conversion rate of fatty acid and fatty alcohol in the hydrogen reduction reaction.
The preparation method of the catalyst comprises the following steps:
s11, weighing nickel powder, cobalt powder, platinum dioxide and ferric chloride according to the mass percentage, dissolving the nickel powder, the cobalt powder, the platinum dioxide and the ferric chloride in deionized water, carrying out ultrasonic mixing for 0.5-1 h, and obtaining suspension at the frequency of 50-80 KHz; the mass of the deionized water is 2.5-4 times of that of the catalyst;
s12, dissolving a reducing agent in methanol or ethanol to prepare a solution with the concentration of 1.0-2.0 mol/L, adding the reducing agent into the suspension under stirring, and reacting for 1-2 hours to obtain a mixture;
s13, performing solid-liquid separation on the mixture obtained in the step S12, washing with water for 2-3 times, washing with ethanol for 2-3 times, and drying at 60-80 ℃ for 2-3 hours to obtain the catalyst.
Preferably, the reducing agent is sodium borohydride or potassium borohydride.
Preferably, the addition amount of the catalyst is 0.5-1.5% of the mass of jojoba oil.
The invention has the beneficial effects that:
the catalyst provided by the invention can further improve the performance of the catalyst and reduce the consumption of noble metals by introducing transition metal iron; active components nickel and cobalt are fully loaded on a platinum dioxide carrier through ultrasound, so that the catalytic property of the catalyst can be effectively improved, and the reduction reaction efficiency is higher; the reasonable active component composition ratio in the catalyst can effectively improve the catalytic activity of the catalyst and increase the conversion rate of fatty alcohol in the hydrogen reduction reaction;
according to the invention, hydrogen and a catalyst are utilized to decompose jojoba oil into fatty acid and fatty alcohol, three-stage rectification is utilized to remove fatty acid, and finally, a crude product of fatty alcohol is purified, so that the purity of the obtained jojoba oil product can reach more than 90%, and high conversion rate relative to jojoba oil can be realized.
Detailed Description
The following description of the embodiments of the present invention will be made clearly and fully with reference to the accompanying drawings, in which it is evident that the embodiments described are only some, but not all embodiments of the invention. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Example 1.
The method for preparing jojoba alcohol from jojoba oil in the embodiment comprises the following steps:
s1, adding jojoba oil and propanol into a reaction kettle, and heating to 65 ℃ under the condition of stirring and refluxing for reaction for 2 hours; the addition amount of the propanol is 50% of the mass of jojoba oil, and the mass fraction of the propanol is 60%;
s2, adding a catalyst into the reaction solution in the step S1 for reduction and activation treatment, using hydrogen to replace air in the kettle after sealing the kettle, introducing hydrogen to the reaction pressure of 3.0MPa, heating to 150 ℃, starting stirring reaction at the stirring speed of 1000r/min for 6h, cooling, and filtering to obtain a mixture;
s3, carrying out three-stage rectification on the mixture obtained in the step S2 through a packed rectifying tower, and introducing filtrate into a first rectifying tower for rectification, wherein the operation temperature of the tower top is 100 ℃, and the vacuum degree of the tower top is 1.0KPa; introducing the residue at the bottom of the first rectifying tower into a second rectifying tower for rectifying, wherein the operation temperature at the top of the tower is 150 ℃, and the vacuum degree at the top of the tower is 2.0KPa; feeding the second distillation column fraction into a third distillation column for rectification, wherein the top operation temperature of the third distillation column is 200 ℃, and the top vacuum degree is 3.0KPa; cooling to obtain crude fatty alcohol;
s4, extracting the crude fatty alcohol product with ethyl acetate for 2 times and 2 hours each time, concentrating the extract to 1.2g/ml at 40 ℃ and dissolving the extract in ethanol with the mass concentration of 70%; loading the extract solution onto macroporous adsorbent resin, eluting with deionized water at a rate of 2BV/h, collecting water eluate, discarding the water eluate, desorbing with 80% ethanol, and collecting eluate;
s5, washing the eluent in the step S4 with 20% acetone for 1 time, and drying at 50 ℃ until the weight is constant, thus obtaining the jojoba alcohol.
The flow rate of the macroporous adsorbent resin on the extract solution of this example was 1.5mL/min.
The mass of deionized water in this example was 5 times that of the macroporous adsorbent resin, and the mass of ethanol was 1.5 times that of the macroporous adsorbent resin.
The macroporous adsorbent resin of this example was HPD-100.
The catalyst of the present example comprises the following components in weight percent: 15% of nickel powder, 18% of cobalt powder, 2% of platinum dioxide, 25% of ferric chloride and 40% of a reducing agent.
The preparation method of the catalyst of the embodiment comprises the following steps:
s11, weighing nickel powder, cobalt powder, platinum dioxide and ferric chloride according to the mass percentage, dissolving in deionized water, and carrying out ultrasonic mixing for 0.5h at the frequency of 50KHz to obtain a suspension; the mass of the deionized water is 2.5 times of that of the catalyst;
s12, dissolving a reducing agent in methanol or ethanol to prepare a solution with the concentration of 1.0mol/L, adding the reducing agent into the suspension under stirring, and reacting for 1h to obtain a mixture;
s13, performing solid-liquid separation on the mixture obtained in the step S12, washing with water for 2 times, washing with ethanol for 2 times, and drying at 60 ℃ for 2 hours to obtain the catalyst.
The reducing agent of this example is sodium borohydride.
The catalyst of this example was added in an amount of 0.5% by mass of jojoba oil.
Example 2.
The method for preparing jojoba alcohol from jojoba oil in the embodiment comprises the following steps:
s1, adding jojoba oil and propanol into a reaction kettle, and heating to 75 ℃ under the condition of stirring and refluxing for reaction for 5 hours; the addition amount of the propanol is 60% of the mass of jojoba oil, and the mass fraction of the propanol is 70%;
s2, adding a catalyst into the reaction liquid in the step S1 for reduction and activation treatment, sealing the kettle, using high-purity nitrogen to replace air in the kettle, then introducing hydrogen to the reaction pressure of 6.0MPa, heating to 200 ℃, starting stirring reaction, wherein the stirring speed is 1500r/min, the reaction time is 12h, cooling, and filtering to obtain a mixture;
s3, carrying out three-stage rectification on the mixture obtained in the step S2 through a packed rectifying tower, and introducing filtrate into a first rectifying tower for rectification, wherein the operation temperature of the tower top is 110 ℃, and the vacuum degree of the tower top is 2.0KPa; introducing the residue at the bottom of the first rectifying tower into a second rectifying tower for rectifying, wherein the operation temperature at the top of the tower is 180 ℃, and the vacuum degree at the top of the tower is 3.0KPa; feeding the second distillation column fraction into a third distillation column for rectification, wherein the top operation temperature of the third distillation column is 250 ℃, and the top vacuum degree is 4.0KPa; cooling to obtain crude fatty alcohol;
s4, extracting the crude fatty alcohol product with ethyl acetate for 4 times and 3 hours each time, concentrating the extract at 60 ℃ to 1.5g/ml, and dissolving the extract in ethanol with the mass concentration of 70%; loading the extract solution on macroporous adsorption resin, eluting with deionized water at the eluting speed of 2.5BV/h, collecting water eluate, discarding the water eluate, desorbing with 80-90% ethanol, and collecting eluate;
and S5, washing the eluent in the step S4 with 20-30 times of acetone, and drying at 60 ℃ until the weight is constant, thus obtaining the jojoba alcohol.
The flow rate of the macroporous adsorbent resin on the extract solution of this example was 2mL/min.
The mass of deionized water in this example was 8 times that of the macroporous adsorbent resin, and the mass of ethanol was 5 times that of the macroporous adsorbent resin.
The macroporous adsorbent resin of this example was HPD-826.
The catalyst of the present example comprises the following components in weight percent: 30% of nickel powder, 29% of cobalt powder, 6% of platinum dioxide, 10% of ferric chloride and 25% of a reducing agent.
The preparation method of the catalyst of the embodiment comprises the following steps:
s11, weighing nickel powder, cobalt powder, platinum dioxide and ferric chloride according to the mass percentage, dissolving in deionized water, and carrying out ultrasonic mixing for 1h at the frequency of 80KHz to obtain a suspension; the mass of the deionized water is 4 times of that of the catalyst;
s12, dissolving a reducing agent in methanol or ethanol to prepare a solution with the concentration of 2.0mol/L, adding the reducing agent into the suspension under stirring, and reacting for 2 hours to obtain a mixture;
s13, performing solid-liquid separation on the mixture obtained in the step S12, washing with water for 3 times, washing with ethanol for 3 times, and drying at 80 ℃ for 3 hours to obtain the catalyst.
The reducing agent of this example is potassium borohydride.
The catalyst of this example was added in an amount of 1.5% by mass of jojoba oil.
Example 3.
The method for preparing jojoba alcohol from jojoba oil in the embodiment comprises the following steps:
s1, adding jojoba oil and propanol into a reaction kettle, and heating to 70 ℃ under the condition of stirring and refluxing for reaction for 4 hours; the addition amount of the propanol is 55% of the mass of jojoba oil, and the mass fraction of the propanol is 65%;
s2, adding a catalyst into the reaction solution in the step S1 for reduction and activation treatment, using hydrogen to replace air in the kettle after sealing the kettle, introducing hydrogen to the reaction pressure of 4.0MPa, heating to 180 ℃, starting stirring reaction at the stirring speed of 1200r/min for 9h, cooling, and filtering to obtain a mixture;
s3, carrying out three-stage rectification on the mixture obtained in the step S2 through a packed rectifying tower, and introducing filtrate into a first rectifying tower for rectification, wherein the operation temperature of the tower top is 105 ℃, and the vacuum degree of the tower top is 1.5KPa; introducing the residue at the bottom of the first rectifying tower into a second rectifying tower for rectifying, wherein the operation temperature at the top of the tower is 170 ℃, and the vacuum degree at the top of the tower is 2.5KPa; feeding the second distillation column fraction into a third distillation column for rectification, wherein the top operation temperature of the third distillation column is 220 ℃, and the top vacuum degree is 3.5KPa; cooling to obtain crude fatty alcohol;
s4, extracting the crude fatty alcohol product with ethyl acetate for 3 times and 2.5 hours each time, concentrating the extract to 1.3g/ml at 50 ℃ and dissolving the extract in 70% ethanol; loading the extract solution onto macroporous adsorbent resin, eluting with deionized water at a rate of 2.2BV/h, collecting water eluate, discarding the water eluate, desorbing with 85% ethanol, and collecting eluate;
s5, washing the eluent in the step S4 with 25% acetone for 2 times, and drying at 55 ℃ until the weight is constant, thus obtaining the jojoba alcohol.
The flow rate of the macroporous adsorbent resin on the extract solution of this example was 1.7mL/min.
The mass of deionized water in this example was 7 times that of the macroporous adsorbent resin, and the mass of ethanol was 3.5 times that of the macroporous adsorbent resin.
The macroporous adsorbent resin of this example was HPD-750.
The catalyst raw material of the embodiment comprises the following components in percentage by weight: 22% of nickel powder, 24% of cobalt powder, 4% of platinum dioxide, 17% of ferric chloride and 33% of a reducing agent.
The preparation method of the catalyst of the embodiment comprises the following steps:
s11, weighing nickel powder, cobalt powder, platinum dioxide and ferric chloride according to the mass percentage, dissolving in deionized water, and carrying out ultrasonic mixing for 0.8h at the frequency of 65KHz to obtain a suspension; the mass of the deionized water is 3 times of that of the catalyst;
s12, dissolving a reducing agent in methanol or ethanol to prepare a solution with the concentration of 1.5mol/L, adding the reducing agent into the suspension under stirring, and reacting for 1.5 hours to obtain a mixture;
s13, performing solid-liquid separation on the mixture obtained in the step S12, washing with water for 2 times, washing with ethanol for 3 times, and drying at 70 ℃ for 2.5 hours to obtain the catalyst.
The reducing agent of this example is sodium borohydride.
The catalyst of this example was added in an amount of 1.0% by mass of jojoba oil.
S1, adding jojoba oil and propanol into a reaction kettle, and heating to 70 ℃ under the condition of stirring and refluxing for reaction for 4 hours; the addition amount of the propanol is 55% of the mass of jojoba oil, and the mass fraction of the propanol is 65%;
s2, adding a catalyst into the reaction solution in the step S1 for reduction and activation treatment, using hydrogen to replace air in the kettle after sealing the kettle, introducing hydrogen to the reaction pressure of 4.0MPa, heating to 180 ℃, starting stirring reaction at the stirring speed of 1200r/min for 9h, cooling, and filtering to obtain a mixture;
s3, carrying out three-stage rectification on the mixture in the step S2 through a packed rectifying tower, and introducing filtrate into a first rectifying tower for rectification, wherein the operation temperature of the tower top is 105 ℃, and the vacuum degree of the tower top is 1.5KPa; introducing the residue at the bottom of the first rectifying tower into a second rectifying tower for rectifying, wherein the operation temperature at the top of the tower is 170 ℃, and the vacuum degree at the top of the tower is 2.5KPa; feeding the second distillation column fraction into a third distillation column for rectification, wherein the top operation temperature of the third distillation column is 220 ℃, and the top vacuum degree is 3.5KPa; cooling to obtain crude fatty alcohol;
s4, extracting the crude fatty alcohol product with ethyl acetate for 3 times and 2.5 hours each time, concentrating the extract to 1.3g/ml at 50 ℃ and dissolving the extract in 70% ethanol; loading the extract solution onto macroporous adsorbent resin, eluting with deionized water at a rate of 2.2BV/h, collecting water eluate, discarding the water eluate, desorbing with 85% ethanol, and collecting eluate;
s5, washing the eluent in the step S4 with 25% acetone for 2 times, and drying at 55 ℃ until the weight is constant, thus obtaining the jojoba alcohol.
Comparative example 1.
The difference from example 3 is that no catalyst is added in the process for preparing jojoba alcohol.
Comparative example 2.
Unlike example 3, the process for preparing jojoba alcohol is:
s1, adding jojoba oil and propanol into a reaction kettle, and heating to 65-75 ℃ under the condition of stirring and refluxing for reaction for 2-5 hours; the addition amount of the propanol is 50-60% of the mass of jojoba oil, and the mass fraction of the propanol is 60-70%;
s2, adding a catalyst into the reaction liquid in the step S1 for reduction and activation treatment, sealing the kettle, using high-purity nitrogen or hydrogen to replace air in the kettle, then introducing hydrogen to the reaction pressure of 3.0-6.0 MPa, heating to 150-200 ℃, starting stirring reaction at the stirring speed of 1000-1500 r/min for 6-12 h, cooling, and filtering to obtain a mixture;
s3, carrying out three-stage rectification on the mixture in the step S2 through a packed rectifying tower, and introducing filtrate into a first rectifying tower for rectification, wherein the operation temperature of the tower top is 100-110 ℃, and the vacuum degree of the tower top is 1.0-2.0 KPa; introducing the residue at the bottom of the first rectifying tower into a second rectifying tower for rectifying, wherein the operation temperature of the tower top is 150-180 ℃, and the vacuum degree of the tower top is 2.0-3.0 KPa; introducing the second distillation column fraction into a third distillation column for distillation, wherein the operation temperature of the top of the third distillation column is 200-250 ℃, and the vacuum degree of the top of the third distillation column is 3.0-4.0 KPa; cooling to obtain crude fatty alcohol;
and S4, washing the crude fatty alcohol product in the step S3 with 20-30% acetone for 1-3 times, and drying at 50-60 ℃ until the weight is constant, thus obtaining the jojoba alcohol.
Comparative example 3.
Unlike example 3, the process for preparing jojoba alcohol is:
s1, adding jojoba oil and propanol into a reaction kettle, and heating to 70 ℃ under the condition of stirring and refluxing for reaction for 4 hours; the addition amount of the propanol is 55% of the mass of jojoba oil, and the mass fraction of the propanol is 65%;
s2, sequentially placing the mixture obtained in the step S1 into a secondary continuous molecular distiller to separate fatty acid components in the mixture, wherein the feeding amount of the secondary continuous molecular distiller is controlled to be 5-15L/min, the temperature in the primary distiller is 100-120 ℃, and the vacuum degree is 100Pa; the temperature in the secondary distiller is 130-150 ℃ and the vacuum degree is 500Pa, so that a crude fatty alcohol product is obtained;
s3, extracting the crude fatty alcohol product with ethyl acetate for 3 times and 2.5 hours each time, concentrating the extract to 1.3g/ml at 50 ℃ and dissolving the extract in 70% ethanol; loading HPD-100 macroporous adsorbent resin on the extract solution with flow rate of 1.7mL/min, eluting with deionized water 7 times the mass of macroporous adsorbent resin at elution rate of 2.2BV/h, collecting water eluate, discarding the water eluate, desorbing with 85% ethanol 3.5 times the mass of macroporous adsorbent resin, and collecting eluate;
s4, washing the eluent in the step S3 with 25% acetone for 2 times, and drying at 55 ℃ until the weight is constant, thus obtaining the jojoba alcohol.
Comparative example 4.
The difference from example 3 is that the catalyst comprises, in weight percent: 45% of nickel powder, 35% of cobalt powder and 20% of titanium dioxide; the preparation method comprises the steps of uniformly mixing the components according to the proportion.
Comparative example 5.
The difference from example 3 is that the catalyst is prepared by the following steps:
s11, dissolving nickel powder, cobalt powder and platinum dioxide in acetone, and uniformly stirring at normal temperature to obtain a platinum-containing mixed solution;
s12, preparing ferric chloride into a solution with the concentration of 0.5-4.0 mol/L, pouring the solution into a platinum-containing mixed solution, uniformly stirring, transferring the solution into a high-temperature high-pressure kettle, and placing the solution at the temperature of 120-180 ℃ for thermal reaction for 6-10 hours;
s13, adding a reducing agent ammonium nitrate into the metal salt mixed solution cooled in the step S12 under stirring, and stirring for 3 hours to obtain a mixture;
s14, filtering the mixture obtained in the step S13 to obtain a solid, washing the solid with water until washing liquid is neutral, and obtaining a catalyst precursor; and drying the catalyst precursor at 80-120 ℃ to obtain the catalyst.
The purities, conversions, etc. of the jojoba alcohol products prepared in examples 1-3 and comparative examples 1-5 were compared, and the specific results are shown in the following table:
as is clear from examples 1 to 3, comparative example 1, comparative example 4 and comparative example 5, the reduction reaction of hydrogen was not efficient without adding a catalyst, and the catalytic reduction was achieved to some extent by adjusting the components of the catalyst and changing the preparation method of the catalyst, but the conversion rate relative to jojoba oil was not high.
From examples 1-3, comparative example 2, comparative example 3, it is seen that the step of removing hydrogen reduction makes it difficult to convert jojoba oil into fatty acids and fatty alcohols, fatty acids and fatty alcohols cannot be separated effectively by distillation treatment alone, and the reduction of the final purification step of crude product also affects the purity of jojoba alcohol.
It will be evident to those skilled in the art that the invention is not limited to the details of the foregoing illustrative embodiments, which are to be construed as exemplary and not limiting, the scope of the invention being defined by the appended claims rather than by the foregoing description, and all changes which come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein.
Furthermore, it should be understood that although the present disclosure describes embodiments, not every embodiment is provided with a separate embodiment, and that this description is provided for clarity only, and that the disclosure is not limited to the embodiments described in detail below, and that the embodiments described in the examples may be combined as appropriate to form other embodiments that will be apparent to those skilled in the art.
Claims (10)
1. A process for the preparation of jojoba alcohol from jojoba oil, comprising the steps of:
s1, adding jojoba oil and propanol into a reaction kettle, and heating to 65-75 ℃ under the condition of stirring and refluxing for reaction for 2-5 hours; the addition amount of the propanol is 50-60% of the mass of jojoba oil, and the mass fraction of the propanol is 60-70%;
s2, adding a catalyst into the reaction liquid in the step S1 for reduction and activation treatment, sealing the kettle, using high-purity nitrogen or hydrogen to replace air in the kettle, then introducing hydrogen to the reaction pressure of 3.0-6.0 MPa, heating to 150-200 ℃, starting stirring reaction at the stirring speed of 1000-1500 r/min for 6-12 h, cooling, and filtering to obtain a mixture;
s3, carrying out three-stage rectification on the mixture in the step S2 through a packed rectifying tower, and introducing filtrate into a first rectifying tower for rectification, wherein the operation temperature of the tower top is 100-110 ℃, and the vacuum degree of the tower top is 1.0-2.0 KPa; introducing the residue at the bottom of the first rectifying tower into a second rectifying tower for rectifying, wherein the operation temperature of the tower top is 150-180 ℃, and the vacuum degree of the tower top is 2.0-3.0 KPa; introducing the second distillation column fraction into a third distillation column for distillation, wherein the operation temperature of the top of the third distillation column is 200-250 ℃, and the vacuum degree of the top of the third distillation column is 3.0-4.0 KPa; cooling to obtain crude fatty alcohol;
s4, extracting the crude fatty alcohol product with ethyl acetate for 2-4 times, each time for 2-3 hours, concentrating the extract to 1.2-1.5 g/ml at 40-60 ℃ and dissolving the extract in ethanol with the mass concentration of 70%; loading the extract solution on macroporous adsorption resin, eluting with deionized water at the eluting speed of 2-2.5 BV/h, collecting water eluate, discarding the water eluate, desorbing with 80-90% ethanol, and collecting eluate;
and S5, washing the eluent in the step S4 with 20-30% acetone for 1-3 times, and drying at 50-60 ℃ until the weight is constant, thus obtaining the jojoba alcohol.
2. The method for preparing jojoba alcohol from jojoba oil according to claim 1, wherein the flow rate of macroporous adsorption resin on the extract solution in the step S4 is 1.5-2 ml/min.
3. The method for extracting jojoba alcohol from jojoba oil according to claim 1, wherein in the step S4, the mass of deionized water is 5-8 times that of macroporous adsorption resin, and the mass of ethanol is 1.5-5 times that of macroporous adsorption resin.
4. The method for preparing jojoba alcohol from jojoba oil according to claim 1, wherein the macroporous adsorbent resin is one of the group consisting of HPD-100, HPD-750, and HPD-826.
5. A process for the preparation of jojoba alcohol from jojoba oil according to claim 1, wherein the catalyst comprises the following components in weight percent: 15-30% of nickel powder, 18-29% of cobalt powder, 2-6% of platinum dioxide, 10-25% of ferric chloride and 25-40% of a reducing agent.
6. The method for preparing jojoba alcohol from jojoba oil according to claim 1, wherein the catalyst raw materials comprise the following components in percentage by weight: 22% of nickel powder, 24% of cobalt powder, 4% of platinum dioxide, 17% of ferric chloride and 33% of a reducing agent.
7. The method for preparing jojoba alcohol from jojoba oil according to claim 1, wherein the catalyst is prepared by the following steps:
s11, weighing nickel powder, cobalt powder, platinum dioxide and ferric chloride according to the mass percentage, dissolving the nickel powder, the cobalt powder, the platinum dioxide and the ferric chloride in deionized water, carrying out ultrasonic mixing for 0.5-1 h, and obtaining suspension at the frequency of 50-80 KHz; the mass of the deionized water is 2.5-4 times of that of the catalyst;
s12, dissolving a reducing agent in methanol or ethanol to prepare a solution with the concentration of 1.0-2.0 mol/L, adding the reducing agent into the suspension under stirring, and reacting for 1-2 hours to obtain a mixture;
s13, performing solid-liquid separation on the mixture obtained in the step S12, washing with water for 2-3 times, washing with ethanol for 2-3 times, and drying at 60-80 ℃ for 2-3 hours to obtain the catalyst.
8. A process for the preparation of jojoba alcohol from jojoba oil as claimed in claim 7, wherein the reducing agent is sodium borohydride or potassium borohydride.
9. The method for preparing jojoba alcohol from jojoba oil according to claim 1, wherein the addition amount of the catalyst is 0.5-1.5% of the mass of the jojoba oil.
10. Use of a composition according to any one of claims 1 to 9 for the preparation of jojoba alcohol in jojoba oil.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999020224A2 (en) * | 1997-10-17 | 1999-04-29 | International Flora Technologies, Ltd. | Emollient compositions based on jojoba oil |
| US20010053800A1 (en) * | 1998-06-01 | 2001-12-20 | Verbiscar Anthony J. | Long chain monounsaturated alcohol mixtures |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999020224A2 (en) * | 1997-10-17 | 1999-04-29 | International Flora Technologies, Ltd. | Emollient compositions based on jojoba oil |
| EP1024783A2 (en) * | 1997-10-17 | 2000-08-09 | International Flora Technologies, Ltd. | Emollient compositions based on jojoba oil |
| US20010053800A1 (en) * | 1998-06-01 | 2001-12-20 | Verbiscar Anthony J. | Long chain monounsaturated alcohol mixtures |
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