CN103804135A - Method used for preparing higher alkanols via sunflower wax normal pressure reduction - Google Patents
Method used for preparing higher alkanols via sunflower wax normal pressure reduction Download PDFInfo
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- CN103804135A CN103804135A CN201210440650.9A CN201210440650A CN103804135A CN 103804135 A CN103804135 A CN 103804135A CN 201210440650 A CN201210440650 A CN 201210440650A CN 103804135 A CN103804135 A CN 103804135A
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- sunflower wax
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- 241000208818 Helianthus Species 0.000 title claims abstract description 42
- 235000003222 Helianthus annuus Nutrition 0.000 title claims abstract description 42
- 238000000034 method Methods 0.000 title claims abstract description 36
- 230000009467 reduction Effects 0.000 title claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000003960 organic solvent Substances 0.000 claims abstract description 12
- 230000007935 neutral effect Effects 0.000 claims abstract description 6
- 238000003756 stirring Methods 0.000 claims abstract description 6
- 239000012074 organic phase Substances 0.000 claims abstract description 5
- 239000002904 solvent Substances 0.000 claims abstract description 4
- 239000002994 raw material Substances 0.000 claims abstract description 3
- 239000003638 chemical reducing agent Substances 0.000 claims abstract 5
- 239000012071 phase Substances 0.000 claims abstract 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- -1 lithium aluminum hydride Chemical compound 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 3
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 3
- 239000003921 oil Substances 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- 239000012153 distilled water Substances 0.000 claims 1
- 239000003651 drinking water Substances 0.000 claims 1
- 235000020188 drinking water Nutrition 0.000 claims 1
- 125000001033 ether group Chemical group 0.000 claims 1
- 239000008399 tap water Substances 0.000 claims 1
- 235000020679 tap water Nutrition 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 12
- 238000006243 chemical reaction Methods 0.000 abstract description 5
- 230000008901 benefit Effects 0.000 abstract description 3
- 230000007613 environmental effect Effects 0.000 abstract description 3
- 208000012839 conversion disease Diseases 0.000 abstract description 2
- 230000008569 process Effects 0.000 abstract description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 4
- 239000007787 solid Substances 0.000 abstract 1
- REZQBEBOWJAQKS-UHFFFAOYSA-N triacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO REZQBEBOWJAQKS-UHFFFAOYSA-N 0.000 description 38
- 239000001993 wax Substances 0.000 description 29
- 238000009413 insulation Methods 0.000 description 8
- 150000002191 fatty alcohols Chemical group 0.000 description 7
- 238000000605 extraction Methods 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 239000004367 Lipase Substances 0.000 description 2
- 102000004882 Lipase Human genes 0.000 description 2
- 108090001060 Lipase Proteins 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- IRHTZOCLLONTOC-UHFFFAOYSA-N hexacosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCO IRHTZOCLLONTOC-UHFFFAOYSA-N 0.000 description 2
- 235000019421 lipase Nutrition 0.000 description 2
- CNNRPFQICPFDPO-UHFFFAOYSA-N octacosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCO CNNRPFQICPFDPO-UHFFFAOYSA-N 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- TYWMIZZBOVGFOV-UHFFFAOYSA-N tetracosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCO TYWMIZZBOVGFOV-UHFFFAOYSA-N 0.000 description 2
- 229960002666 1-octacosanol Drugs 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004164 Wax ester Substances 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000002929 anti-fatigue Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229960000735 docosanol Drugs 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 230000000324 neuroprotective effect Effects 0.000 description 1
- 230000000508 neurotrophic effect Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 208000023958 prostate neoplasm Diseases 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000036299 sexual function Effects 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000019386 wax ester Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明提供一种向日葵蜡还原法制备高级烷醇的方法，其特征在于以向日葵蜡为原料，不需要有机溶剂参与反应的条件下，于常压开放体系中还原制备高级烷醇混合物。在85～120℃、持续搅拌的条件下，用还原剂∶向日葵蜡＝1∶10～30的质量比进行反应；再按向日葵蜡：水：有机溶剂=1：10～30：0～30的质量比加入水和有机溶剂，加热至45～96℃，按向日葵蜡：HCl=1：0.1～0.9的质量比加入2M的HCl溶液，45～96℃保温10～30min；抽出水相，在有机相中加水和盐酸溶液45～96℃保温10～30min，调节pH值为中性；抽出水相，蒸干有机相中的溶剂，冷却后的固体即为高级烷醇的混合物。本发明具有工艺简洁、易于操作、环境友好安全、反应在常压开放体系中进行、成本低、反应转化率高、适宜工业化应用等优点。The invention provides a sunflower wax reduction method for preparing higher alkanols, which is characterized in that the sunflower wax is used as a raw material, and the higher alkanol mixture is prepared by reduction in an open system at normal pressure without the need for an organic solvent to participate in the reaction. Under the condition of 85～120℃ and continuous stirring, react with reducing agent: sunflower wax=1:10～30 mass ratio; then press sunflower wax: water: organic solvent=1:10～30:0～30 Add water and organic solvent in mass ratio, heat to 45-96°C, add 2M HCl solution according to the mass ratio of sunflower wax: HCl=1:0.1-0.9, keep warm at 45-96°C for 10-30min; extract the water phase, and put it in the organic Add water and hydrochloric acid solution to the phase and keep it warm at 45-96°C for 10-30 minutes, adjust the pH value to be neutral; extract the water phase, evaporate the solvent in the organic phase, and the cooled solid is a mixture of higher alkanols. The invention has the advantages of simple process, easy operation, environmental friendliness and safety, the reaction is carried out in an open system at normal pressure, low cost, high reaction conversion rate, suitable for industrial application and the like.
Description
Technical field
The method that the present invention relates to the waxed standby high triacontanol mixture of a kind of Sunflower Receptacle, especially a kind of normal pressure reduction method is prepared the method for high triacontanol mixture.
Background technology
[0002] Sunflower Receptacle wax is the seed oil of Sunflower Receptacle and the wax of planting shell surface, and its main component is the senior ester that higher fatty acid and high fatty alcohol form, and senior ester can be converted into high triacontanol through saponification or reduction.
High triacontanol claims again high fatty alcohol, is to contain 12 chain saturated monohydroxy alcohols more than carbon atom.High triacontanol is extensively present in occurring in nature, but exists with natural free fatty alcohol form hardly, but exists with the form of wax ester.Both at home and abroad about the research of high triacontanol concentrates on C
22～C
36the technical fields such as preparation, separation and the utilization of alcohol mixture.Behenyl alcohol in high triacontanol mixture can be used for suppressing tumor of prostate; Tetracosanol can strengthen the function of neural factor; Hexacosyl alcohol has neuroprotective and neurotrophic effect; Octacosanol is universally acknowledged antifatigue material, and has the effect such as reducing blood-fat and sexual function improving; Triacontanol is plant-growth regulator, has the effect of Promoting plant growth.The method being adopted by the waxed standby high triacontanol of Sunflower Receptacle at present has: (l) saponification method: wax saponification under alkaline condition decomposed and remove after soap with calcium precipitation, then obtaining the mixture of high fatty alcohol with solvent extraction.This method technical process is long, adds the solvability of high-grade aliphatic ester in water and dispersed poor, so yield is lower, and product purity is not high, because the method will be used a large amount of alkali, and not only trivial operations, but also cause serious environmental pollution etc.(2) ester-interchange method: it is transesterification reaction that wax is carried out to alcoholysis, then according to the different boiling of reaction product, by the method for vacuum distilling, isolate different products, thereby obtain the method for the mixture of high fatty alcohol.The method chemical reaction process complexity, the reaction product kind obtaining is more, separates object product more difficult.(3) wax is hydrolyzed under acidic conditions, then leaches the method for fatty alcohol through supercutical fluid.In the method, because the acidic hydrolysis of wax is a reversible reaction, its trim point depends on again the ratio of water and the character of ester, and the solubleness of wax basis in water is very little, therefore, under acidic conditions, wax is difficult to be distributed in water, is difficult to carry out so be hydrolyzed this step, and yield is lower.(4) first wax is carried out to enzyme decomposition, extract again afterwards the method for fatty alcohol.This wax that allows is through lipase or the zymolytic method of ester, it is the very promising biological extraction process of one, can under gentle condition, realize the hydrolysis of high-grade aliphatic ester, and the advantage of lipase maximum is that its selectivity is high, this comprises the selectivity of regioselectivity and fatty acid ester, so be the important directions of Future Development.But at present because the enzyme of decomposition wax is unstable, easily poisoning and deactivation, production cost is high, and processing condition are immature, therefore, still in groping property experimental stage, do not obtain commercial application.
Above several method is being prepared the part that all comes with some shortcomings aspect high triacontanol, but is all more traditional and conventional method.Preparing high triacontanol mixture take Sunflower Receptacle wax as raw material through reduction method have not been reported up till now.
Summary of the invention
The object of the present invention is to provide that a kind of technique is succinct, easy handling, cost are low, mild condition, environmental friendliness, the method by the waxed standby high triacontanol mixture of Sunflower Receptacle that yield is high.
The present invention completes by following technical proposal: a kind of normal pressure reduction method is prepared the method for Sunflower Receptacle wax high triacontanol mixture, it is characterized in that through the following step:
A, Sunflower Receptacle wax is heated to 83～120 ℃, under the condition that continues to stir, by reductive agent: Sunflower Receptacle wax=1: 10～30 mass ratio, joins reductive agent in Sunflower Receptacle wax.
B, according to Sunflower Receptacle wax: water: the mass ratio of organic solvent=1:10～30:0～30 adds water and organic solvent in reaction mixture, be heated to 45～96 ℃, by Sunflower Receptacle wax: the mass ratio of HCl=1:0.1～0.9 adds the HCl solution of 2 M, 45～96 ℃ of insulation 10～30 min.
C, extraction water, add the water of 15～30 times of quality of Sunflower Receptacle wax and the HCl solution of a small amount of 2 M, 45～96 ℃ of insulation 10～30 min; Extremely neutral by the pH value of 2 M NaOH solution regulator solutions afterwards.
D, extraction water, the solvent in evaporate to dryness organic phase, is cooled to normal temperature, obtains block Sunflower Receptacle wax high triacontanol.
Described reductive agent can be Ranny-Ni, lithium aluminum hydride; Described organic solvent is one or more in the organic solvents such as ether, sherwood oil, methyl alcohol, ethanol, chloroform, acetone, ethyl acetate, benzene, butanols.
The present invention has following advantages and effect: adopt such scheme, in comparatively gentle normal pressure open system, by the waxed high triacontanol mixture that obtains of Sunflower Receptacle, not only technique is simple, be easy to control, and reaction process organic solvent-free participates in, environmental friendliness safety, cost is low, and reaction conversion ratio is high, good product quality.
Embodiment
Below in conjunction with specific embodiment, the present invention is described further.
Embodiment 1
A, in 1000 ml beakers, 100 g Sunflower Receptacle waxes are heated to 85 ℃, under the condition that continues to stir, slowly add 10 g reductive agent Ranny-Ni.
B, in reaction mixture, add 300 ml water, be heated to 96 ℃, add HCl solution 150 ml of 2 M, 96 ℃ of insulation 20 min.
C, extract water out, add HCl solution 5 ml of 300 ml water and 2 M, 96 ℃ of insulation 10 min; Extremely neutral by the pH value of 2 M NaOH solution regulator solutions afterwards.
D, extraction water, be cooled to normal temperature, obtains Sunflower Receptacle wax high triacontanol 95 g.
Embodiment 2
A, in 20 L flasks, 1000 g Sunflower Receptacle waxes are heated to 90 ℃, under the condition that continues to stir, 80 g lithium aluminum hydrides are joined in Sunflower Receptacle wax.
B, in flask, add 5 L water and 2 L chloroforms, be heated to 50 ℃, add HCl solution 4 L of 2 M, flask meets 50 ℃ of insulation 30 min of condenser.
C, extract water out, add HCl solution 100 ml of Sunflower Receptacle wax 5 L water and 2 M, 50 ℃ of insulation 10 min; Extremely neutral by the pH value of 2 M NaOH solution regulator solutions afterwards.
D, extraction water, the organic solvent in evaporate to dryness organic phase, is cooled to normal temperature, obtains block Sunflower Receptacle wax high triacontanol 960 g.
Embodiment 3
A, in 100 L reactors, 15 kg Sunflower Receptacle waxes are heated to 85 ℃, under the condition that continues to stir, slowly add lithium aluminum hydride 1.5 kg.
B, in reactor, add 35 L water, 20 L sherwood oils, 5 L butanols, be heated to 55 ℃, add HCl solution 10 L of 2 M, 55 ℃ of insulation 30 min.
C, extract water out, add HCl solution 100 ml of 30 L water and 2 M, 80 ℃ of insulation 30 min; Extremely neutral by the pH value of 2 M NaOH solution regulator solutions afterwards.
D, extraction water, the organic solvent in evaporate to dryness organic phase, is cooled to normal temperature, obtains block Sunflower Receptacle wax high triacontanol 14.6 kg.
Claims (4)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210440650.9A CN103804135A (en) | 2012-11-07 | 2012-11-07 | Method used for preparing higher alkanols via sunflower wax normal pressure reduction |
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| CN201210440650.9A CN103804135A (en) | 2012-11-07 | 2012-11-07 | Method used for preparing higher alkanols via sunflower wax normal pressure reduction |
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| CN103804135A true CN103804135A (en) | 2014-05-21 |
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| CN201210440650.9A Pending CN103804135A (en) | 2012-11-07 | 2012-11-07 | Method used for preparing higher alkanols via sunflower wax normal pressure reduction |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112500263A (en) * | 2020-12-07 | 2021-03-16 | 中国林业科学研究院资源昆虫研究所 | Method for preparing higher alkanol by reducing white wax with red aluminum under normal pressure |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020183236A1 (en) * | 1999-11-10 | 2002-12-05 | Hubert Mimoun | Use of a fatty alcohol in a perfume composition |
| CN1834079A (en) * | 2006-04-18 | 2006-09-20 | 浙江大学 | Process of preparing high-grade fatty alcohol through non-catalytic hydrolysis of rice bran wax in near critical aqueous medium |
| CN101293811A (en) * | 2008-06-24 | 2008-10-29 | 中国林业科学研究院资源昆虫研究所 | Method for preparing higher alkanol mixture from white wax |
| CN101386562A (en) * | 2008-08-29 | 2009-03-18 | 中国林业科学研究院资源昆虫研究所 | Method for preparing policosanol mixture by nonsolvent reduction method |
-
2012
- 2012-11-07 CN CN201210440650.9A patent/CN103804135A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020183236A1 (en) * | 1999-11-10 | 2002-12-05 | Hubert Mimoun | Use of a fatty alcohol in a perfume composition |
| CN1834079A (en) * | 2006-04-18 | 2006-09-20 | 浙江大学 | Process of preparing high-grade fatty alcohol through non-catalytic hydrolysis of rice bran wax in near critical aqueous medium |
| CN101293811A (en) * | 2008-06-24 | 2008-10-29 | 中国林业科学研究院资源昆虫研究所 | Method for preparing higher alkanol mixture from white wax |
| CN101386562A (en) * | 2008-08-29 | 2009-03-18 | 中国林业科学研究院资源昆虫研究所 | Method for preparing policosanol mixture by nonsolvent reduction method |
Non-Patent Citations (1)
| Title |
|---|
| 马李一灯: "虫白蜡还原法制备高级烷醇混合物研究", 《林产化学与工业》, vol. 29, no. 5, 31 October 2009 (2009-10-31), pages 6 - 10 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112500263A (en) * | 2020-12-07 | 2021-03-16 | 中国林业科学研究院资源昆虫研究所 | Method for preparing higher alkanol by reducing white wax with red aluminum under normal pressure |
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Application publication date: 20140521 |