CN105294402A - Method of extracting natural fenchol with high purity from a fenchol-containing by-product of turpentine - Google Patents
Method of extracting natural fenchol with high purity from a fenchol-containing by-product of turpentine Download PDFInfo
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- CN105294402A CN105294402A CN201510857281.7A CN201510857281A CN105294402A CN 105294402 A CN105294402 A CN 105294402A CN 201510857281 A CN201510857281 A CN 201510857281A CN 105294402 A CN105294402 A CN 105294402A
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- fenchol
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- IAIHUHQCLTYTSF-UHFFFAOYSA-N 2,2,4-trimethylbicyclo[2.2.1]heptan-3-ol Chemical compound C1CC2(C)C(O)C(C)(C)C1C2 IAIHUHQCLTYTSF-UHFFFAOYSA-N 0.000 title claims abstract description 278
- 229930006727 (-)-endo-fenchol Natural products 0.000 title claims abstract description 140
- 239000006227 byproduct Substances 0.000 title claims abstract description 43
- 238000000034 method Methods 0.000 title claims abstract description 17
- 241000779819 Syncarpia glomulifera Species 0.000 title abstract description 14
- 239000001739 pinus spp. Substances 0.000 title abstract description 14
- 229940036248 turpentine Drugs 0.000 title abstract description 14
- 239000000047 product Substances 0.000 claims abstract description 58
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 45
- 238000002425 crystallisation Methods 0.000 claims abstract description 26
- 230000008025 crystallization Effects 0.000 claims abstract description 25
- 238000000926 separation method Methods 0.000 claims abstract description 25
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims abstract description 23
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 18
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 15
- 239000000203 mixture Substances 0.000 claims abstract description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000007710 freezing Methods 0.000 claims abstract description 6
- 230000008014 freezing Effects 0.000 claims abstract description 6
- 229930003658 monoterpene Natural products 0.000 claims abstract description 6
- 150000002773 monoterpene derivatives Chemical class 0.000 claims abstract description 6
- 235000002577 monoterpenes Nutrition 0.000 claims abstract description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 67
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 32
- 229910052799 carbon Inorganic materials 0.000 claims description 25
- 238000007598 dipping method Methods 0.000 claims description 22
- 239000011259 mixed solution Substances 0.000 claims description 18
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 claims description 17
- 229910000360 iron(III) sulfate Inorganic materials 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- 150000007513 acids Chemical class 0.000 claims description 16
- 238000005119 centrifugation Methods 0.000 claims description 16
- 239000000463 material Substances 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000000376 reactant Substances 0.000 claims description 12
- 230000035484 reaction time Effects 0.000 claims description 12
- 238000010992 reflux Methods 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 10
- 230000002378 acidificating effect Effects 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 9
- 238000000643 oven drying Methods 0.000 claims description 9
- 239000012047 saturated solution Substances 0.000 claims description 9
- 235000011149 sulphuric acid Nutrition 0.000 claims description 8
- 239000001117 sulphuric acid Substances 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 239000002994 raw material Substances 0.000 abstract description 6
- 230000008901 benefit Effects 0.000 abstract description 5
- 238000009835 boiling Methods 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 3
- 238000011031 large-scale manufacturing process Methods 0.000 abstract description 3
- 125000000524 functional group Chemical group 0.000 abstract description 2
- 238000005406 washing Methods 0.000 abstract description 2
- 239000003377 acid catalyst Substances 0.000 abstract 2
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 abstract 1
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 abstract 1
- 238000004134 energy conservation Methods 0.000 abstract 1
- 229930007744 linalool Natural products 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 23
- 239000007788 liquid Substances 0.000 description 11
- WUOACPNHFRMFPN-SECBINFHSA-N (S)-(-)-alpha-terpineol Chemical group CC1=CC[C@@H](C(C)(C)O)CC1 WUOACPNHFRMFPN-SECBINFHSA-N 0.000 description 10
- OVKDFILSBMEKLT-UHFFFAOYSA-N alpha-Terpineol Natural products CC(=C)C1(O)CCC(C)=CC1 OVKDFILSBMEKLT-UHFFFAOYSA-N 0.000 description 10
- 229940088601 alpha-terpineol Drugs 0.000 description 10
- 239000003205 fragrance Substances 0.000 description 10
- LHXDLQBQYFFVNW-UHFFFAOYSA-N Fenchone Chemical compound C1CC2(C)C(=O)C(C)(C)C1C2 LHXDLQBQYFFVNW-UHFFFAOYSA-N 0.000 description 6
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 4
- 238000005194 fractionation Methods 0.000 description 4
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 4
- LHXDLQBQYFFVNW-XCBNKYQSSA-N (+)-Fenchone Natural products C1C[C@]2(C)C(=O)C(C)(C)[C@H]1C2 LHXDLQBQYFFVNW-XCBNKYQSSA-N 0.000 description 3
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 3
- 235000011613 Pinus brutia Nutrition 0.000 description 3
- 241000018646 Pinus brutia Species 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 229930006735 fenchone Natural products 0.000 description 3
- 235000013599 spices Nutrition 0.000 description 3
- 150000003505 terpenes Chemical group 0.000 description 3
- 235000007586 terpenes Nutrition 0.000 description 3
- 239000000341 volatile oil Substances 0.000 description 3
- WTARULDDTDQWMU-RKDXNWHRSA-N (+)-β-pinene Chemical compound C1[C@H]2C(C)(C)[C@@H]1CCC2=C WTARULDDTDQWMU-RKDXNWHRSA-N 0.000 description 2
- WTARULDDTDQWMU-IUCAKERBSA-N (-)-Nopinene Natural products C1[C@@H]2C(C)(C)[C@H]1CCC2=C WTARULDDTDQWMU-IUCAKERBSA-N 0.000 description 2
- 241000675108 Citrus tangerina Species 0.000 description 2
- WTARULDDTDQWMU-UHFFFAOYSA-N Pseudopinene Natural products C1C2C(C)(C)C1CCC2=C WTARULDDTDQWMU-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 2
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 description 2
- UAHWPYUMFXYFJY-UHFFFAOYSA-N beta-myrcene Chemical compound CC(C)=CCCC(=C)C=C UAHWPYUMFXYFJY-UHFFFAOYSA-N 0.000 description 2
- 229930006722 beta-pinene Natural products 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- -1 fenchol ester Chemical class 0.000 description 2
- LCWMKIHBLJLORW-UHFFFAOYSA-N gamma-carene Natural products C1CC(=C)CC2C(C)(C)C21 LCWMKIHBLJLORW-UHFFFAOYSA-N 0.000 description 2
- 230000036571 hydration Effects 0.000 description 2
- 238000006703 hydration reaction Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- GRWFGVWFFZKLTI-UHFFFAOYSA-N rac-alpha-Pinene Natural products CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- NPNUFJAVOOONJE-ZIAGYGMSSA-N β-(E)-Caryophyllene Chemical compound C1CC(C)=CCCC(=C)[C@H]2CC(C)(C)[C@@H]21 NPNUFJAVOOONJE-ZIAGYGMSSA-N 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- DTGKSKDOIYIVQL-MRTMQBJTSA-N (-)-isoborneol Chemical compound C1C[C@@]2(C)[C@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-MRTMQBJTSA-N 0.000 description 1
- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- 239000001169 1-methyl-4-propan-2-ylcyclohexa-1,4-diene Substances 0.000 description 1
- NVEQFIOZRFFVFW-UHFFFAOYSA-N 9-epi-beta-caryophyllene oxide Natural products C=C1CCC2OC2(C)CCC2C(C)(C)CC21 NVEQFIOZRFFVFW-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- 241001647745 Banksia Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- 241000190410 Citrus longispina Species 0.000 description 1
- IAIHUHQCLTYTSF-MRTMQBJTSA-N Fenchyl alcohol Chemical compound C1C[C@]2(C)[C@H](O)C(C)(C)[C@H]1C2 IAIHUHQCLTYTSF-MRTMQBJTSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- PDSNLYSELAIEBU-UHFFFAOYSA-N Longifolene Chemical compound C1CCC(C)(C)C2C3CCC2C1(C)C3=C PDSNLYSELAIEBU-UHFFFAOYSA-N 0.000 description 1
- ZPUKHRHPJKNORC-UHFFFAOYSA-N Longifolene Natural products CC1(C)CCCC2(C)C3CCC1(C3)C2=C ZPUKHRHPJKNORC-UHFFFAOYSA-N 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- 235000008124 Picea excelsa Nutrition 0.000 description 1
- 240000000020 Picea glauca Species 0.000 description 1
- 235000008127 Picea glauca Nutrition 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- FAMPSKZZVDUYOS-UHFFFAOYSA-N alpha-Caryophyllene Natural products CC1=CCC(C)(C)C=CCC(C)=CCC1 FAMPSKZZVDUYOS-UHFFFAOYSA-N 0.000 description 1
- VYBREYKSZAROCT-UHFFFAOYSA-N alpha-myrcene Natural products CC(=C)CCCC(=C)C=C VYBREYKSZAROCT-UHFFFAOYSA-N 0.000 description 1
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 1
- 230000001166 anti-perspirative effect Effects 0.000 description 1
- 239000003213 antiperspirant Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- NPNUFJAVOOONJE-UHFFFAOYSA-N beta-cariophyllene Natural products C1CC(C)=CCCC(=C)C2CC(C)(C)C21 NPNUFJAVOOONJE-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Natural products C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 description 1
- 229940116229 borneol Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229940117948 caryophyllene Drugs 0.000 description 1
- NPNUFJAVOOONJE-UONOGXRCSA-N caryophyllene Natural products C1CC(C)=CCCC(=C)[C@@H]2CC(C)(C)[C@@H]21 NPNUFJAVOOONJE-UONOGXRCSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 235000001510 limonene Nutrition 0.000 description 1
- 229940087305 limonene Drugs 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 150000007875 phellandrene derivatives Chemical class 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000010675 spruce oil Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
-
- 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
- C07C29/56—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by isomerisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Abstract
The invention discloses a method of extracting natural fenchol with high purity from a fenchol-containing by-product of turpentine. The fenchol-containing by-product mainly comprises a monoterpene alcohol mixture of linalool, the fenchol and the like, wherein the content of the fenchol is 50 to 60 percent. The method is characterized by comprising the steps of adding an acid catalyst p-toluenesulfonic acid into the fenchol-containing by-product of the turpentine to perform a catalytic reaction; washing an oil layer obtained by neutralization and standing with water, then performing rectification and freezing crystallization, finally performing centrifugal separation at low temperature to obtain a natural fenchol product of which the purity is greater than 96 percent. According to the acid catalyst p-toluenesulfonic acid, a selective catalysis is performed on the monoterpene alcohol mixture by utilizing the difference of functional group activity, isomerides of which the boiling point is similar to that of the fenchol are removed, so that the natural fenchol with high purity is obtained. By adopting the fenchol-containing by-product of the turpentine as a raw material, the source is extensive, the cost is low, energy conservation and environment protection are realized, and the method is suitable for large-scale production, has very good economic benefit and social benefit.
Description
Technical field
The invention belongs to and extract natural essence spices technical field, relate to a kind of from turps containing the method extracting high-purity natural fenchol fenchol by product.
Background technology
Fenchol, also known as fenchyl alcohol, chemistry 1,3,3-trimethylammonium-2-norbornanol by name, the camphor sample smell in oranges and tangerines aromatic, have bitter limette like local flavor, be slightly soluble in water, be dissolved in ethanol, natural mixture is present in white spruce oil and pine tree wet goods.Its main application: be defined as the food spices allowing to use in GB2760-1996.Fenchol is widely used in the banksia rose, hay-scented, oranges and tangerines type or some bouquet type composition and makeup, also can be used for, in the household chemicalss such as antiperspirant, fabric flexibility agent and liquid washing agent, also to carry out esterification with multiple organic acid and obtaining the spices such as fenchol ester.Current fenchol obtains mainly through two approach, and one is produced by organic synthesis, such as, be starting raw material with fenchone, carries out grignard reaction or reduce etc. with alcohol-sodium by ethylmagnesium bromide.Two is by from containing separation and Extraction in the natural essential oil of fenchol.
Turps is one of maximum natural essential oil kind of China, is green renewable resources.It is terpenes mixture mainly, as the α-pinene of monoterpenes, amphene, beta-pinene, myrcene, phellandrene, limonene, to flower umbrella hydrocarbon etc., the longifolene, caryophyllene etc. of sesquiterpenoids.It can not be used as industrial chemicals or perfume base as the monomeric compound that purity is higher, is often separated, therefrom obtained highly purified single-component compound in production.When turps carries out fractionation, the alcohol derivatives component of some monoterpenes can be obtained, as Terpineol 350, phantol, fenchol, can fenchol be extracted from these by-product alcohols.Factory generally adopts the method for fractionation therefrom to produce fenchol, but due to boiling point close, usually obtained fenchol product content is at 50-60%.
Chinese patent application CN102241567A, disclose a kind of method of turps one-step synthesis method fenchol, take turps as raw material, be catalyzer with CHKC-4, the catalysis characteristics of its high reactivity, highly selective is utilized to carry out catalytic isomerization, hydration to firpene (α-pinene, beta-pinene), isomery, hydration one step complete, combined with chemical process by physical method again, utilize the multiple advanced isolation technique assembling such as high-efficiency vacuum fractionation, fusion-crystallization integrated, prepare fenchol yield >=50%, purity is the fenchol product of 99%.
The main Problems existing of technology of existing synthesis fenchol: if be that starting raw material synthesizes with fenchone, then the fenchone of natural origin is less, causes product cost higher; If with firpene carry out isomery water and, then operational path is long, produces the isomers of more fenchol, as borneol, isocamphol etc., adds the difficulty of separation.Existing directly from containing the technology be separated fenchol essential oil, subject matter is need through repeatedly repeated isolation, and energy consumption is high, and usual product purity is not high (< 60%) also.
Summary of the invention
The present invention is in order to overcome the deficiencies in the prior art, and provide a kind of raw material sources extensive, energy-conserving and environment-protective, cost is low, and product purity is high, and what be suitable for large-scale production contains from turps the method extracting high-purity natural fenchol fenchol by product.
To achieve these goals, technical scheme of the present invention is as follows:
A kind of from turps containing the method extracting high-purity natural fenchol fenchol by product, described mainly contains the monoterpene such as phantol, fenchol alcohol mixture containing fenchol by product, wherein the content of fenchol is 50-60%, catalyzed reaction is carried out containing adding an acidic catalyst tosic acid in fenchol by product at turps, after the standing oil reservoir obtained of neutralization is washed, again by rectifying and freezing and crystallizing, last low-temperature centrifugation is separated, and obtains the natural fenchol product of purity > 96%; Concrete operation step is as follows:
(1) catalyzed reaction: will add in reactor containing fenchol by product, adds an acidic catalyst tosic acid of material weight concentration 0.2-3%, and stir, temperature of reaction controls at 50-100 DEG C, reaction times 2-3h;
(2) wash: the reactant that step (1) obtains is cooled to room temperature, then add sig water neutralization, staticly settle, isolate water layer and oil reservoir, isolated oil-reservoir water is washed till neutrality;
(3) rectifying: the oil reservoir after step (2) being washed drops into rectifying tower, vacuum tightness <-0.09MPa, and tower top temperature controls at 114-120 DEG C, with reflux ratio 4:1-6:1, obtains the fenchol primary products of purity >=80%;
(4) freezing and crystallizing: the fenchol primary products that step (3) obtains are put into freezer crystallization 15h, temperature of ice house control for≤-15 DEG C;
(5) centrifugation: the fenchol primary products after step (4) crystallization are carried out low-temperature centrifugation separation, the temperature be separated controls as < 0 DEG C, rotating speed > 5000r/min, obtains the product of fenchol content > 96%.
An acidic catalyst tosic acid described in above step (1) is that load is on carrier active carbon, concrete grammar is saturated solution carrier active carbon being put into tosic acid, after dipping 10-20h, filter, then carrier active carbon is put into oven drying, temperature controls at 110-115 DEG C, and time of drying is 2-3h, obtain activated carbon supported after toluenesulphonic acids.
Preferably, above-described carrier active carbon is through the impregnated gac of sulfuric acid, concrete dipping method is that conventional activated carbon to be put into volumetric concentration be 30-60% dilute sulphuric acid, dipping 5-8h, filter, then the gac being adsorbed with dilute sulphuric acid is put into baking oven and toast 2-3h at 120-150 DEG C, obtain carrier active carbon.
Preferably, above-described carrier active carbon is through the impregnated gac of ferric sulfate mixed solution, concrete dipping method is that carrier active carbon is put into ferric sulfate mixed solution, dipping 5-8h, filter, the carrier active carbon water being adsorbed with ferric sulfate is cleaned 2-3 time, is then filtered dry water, put into baking oven and toast 1-2h at 150-180 DEG C, obtain carrier active carbon.
Above-described ferric sulfate mixed solution is the mixed solution of saturated ferrum sulfuricum oxydatum solutum and sulfuric acid, and its weight ratio is saturated ferrum sulfuricum oxydatum solutum: sulfuric acid=2-3: 7-8, and mixed solution is for being acidity.
Relative to prior art, the advantage that the present invention has and positively effect as follows:
1, the present invention is by adding an acidic catalyst tosic acid at turps containing in fenchol by product, utilize the difference of functional group's activity, carry out selective catalysis, remove the isomers close with fenchol boiling point, be separated with freezing and crystallizing by rectifying again, obtain the natural fenchol product of purity > 96%, product purity is high.
2, China is the country that pine resin yield is maximum in the world, utilizes pine gum processing rosin, turps few hundred thousand tonnes of every year, aboundresources, produces active; Turps is terpene mixture, time every year by fractionation purification firpene, also obtains a large amount of sesquiterpenoidss and terpene derivant; The present invention selects in turps and contains fenchol by product as raw material, and wide material sources, cost is low, energy-conserving and environment-protective, is applicable to large-scale production, has good economic benefit and social benefit.
Embodiment
Below in conjunction with specific embodiment, the invention will be further described.
Embodiment 1:
Get that turpentine distilling goes out containing fenchol by product 10kg, proterties is weak yellow liquid, has the camphoraceous fragrance of class, and main component is alpha-terpineol 6.5%, phantol 27%, fenchol 59.3%.
To add in reactor containing fenchol by product, and add an acidic catalyst tosic acid of material weight concentration 0.02Kg, stir, temperature of reaction controls at 50 DEG C, reaction times 3h.After catalyzed reaction, the reactant obtained is cooled to room temperature, then adds sig water neutralization, staticly settle, isolate water layer and oil reservoir, isolated oil-reservoir water is washed till neutrality.Oil reservoir is dropped into rectifying tower, and control vacuum tightness <-0.09MPa, tower top temperature controls at 114-120 DEG C, with reflux ratio 4:1, obtains the fenchol primary products of purity >=80%.Again the fenchol primary products obtained are put into freezer crystallization 15h, temperature of ice house control for≤-15 DEG C.Fenchol primary products after crystallization are carried out low-temperature centrifugation separation, and the temperature of separation controls, for < 0 DEG C, rotating speed > 5000r/min, to obtain the product of fenchol content 97.1%.
Embodiment 2:
Get that turpentine distilling goes out containing fenchol by product 10kg, proterties is weak yellow liquid, has the camphoraceous fragrance of class, and main component is alpha-terpineol 4.7%, phantol 30.5%, fenchol 55.2%.
To add in reactor containing fenchol by product, and add an acidic catalyst tosic acid of material weight concentration 0.3Kg, stir, temperature of reaction controls at 100 DEG C, reaction times 2h.After catalyzed reaction, the reactant obtained is cooled to room temperature, then adds sig water neutralization, staticly settle, isolate water layer and oil reservoir, isolated oil-reservoir water is washed till neutrality.Oil reservoir is dropped into rectifying tower, and control vacuum tightness <-0.09MPa, tower top temperature controls at 114-120 DEG C, with reflux ratio 6:1, obtains the fenchol primary products of purity >=80%.Again the fenchol primary products obtained are put into freezer crystallization 15h, temperature of ice house control for≤-15 DEG C.Fenchol primary products after crystallization are carried out low-temperature centrifugation separation, and the temperature of separation controls, for < 0 DEG C, rotating speed > 5000r/min, to obtain the product of fenchol content 96.5%.
Embodiment 3:
Get that turpentine distilling goes out containing fenchol by product 10kg, proterties is weak yellow liquid, has the camphoraceous fragrance of class, and main component is alpha-terpineol 3.7%, phantol 27.4%, fenchol 60.3%.
To add in reactor containing fenchol by product, and add an acidic catalyst tosic acid of material weight concentration 0.25Kg, stir, temperature of reaction controls at 80 DEG C, reaction times 3h.After catalyzed reaction, the reactant obtained is cooled to room temperature, then adds sig water neutralization, staticly settle, isolate water layer and oil reservoir, isolated oil-reservoir water is washed till neutrality.Oil reservoir is dropped into rectifying tower, and control vacuum tightness <-0.09MPa, tower top temperature controls at 114-120 DEG C, with reflux ratio 5:1, obtains the fenchol primary products of purity >=80%.Again the fenchol primary products obtained are put into freezer crystallization 15h, temperature of ice house control for≤-15 DEG C.Fenchol primary products after crystallization are carried out low-temperature centrifugation separation, and the temperature of separation controls, for < 0 DEG C, rotating speed > 5000r/min, to obtain the product of fenchol content 97.5%.
Embodiment 4:
Get that turpentine distilling goes out containing fenchol by product 10kg, proterties is weak yellow liquid, has the camphoraceous fragrance of class, and main component is alpha-terpineol 2.3%, phantol 29.8%, fenchol 58.4%.Get the saturated solution that gac puts into tosic acid, dipping 20h after, filter, then gac is put into oven drying, temperature controls at 115 DEG C, and time of drying is 2h, obtain activated carbon supported after toluenesulphonic acids.
To add in reactor containing fenchol by product, add material weight concentration 0.02Kg activated carbon supported after toluenesulphonic acids, stir, temperature of reaction controls at 50 DEG C, reaction times 3h.After catalyzed reaction, the reactant obtained is cooled to room temperature, then adds sig water neutralization, staticly settle, isolate water layer and oil reservoir, isolated oil-reservoir water is washed till neutrality.Oil reservoir is dropped into rectifying tower, and control vacuum tightness <-0.09MPa, tower top temperature controls at 114-120 DEG C, with reflux ratio 4:1, obtains the fenchol primary products of purity >=80%.Again the fenchol primary products obtained are put into freezer crystallization 15h, temperature of ice house control for≤-15 DEG C.Fenchol primary products after crystallization are carried out low-temperature centrifugation separation, and the temperature of separation controls, for < 0 DEG C, rotating speed > 5000r/min, to obtain the product of fenchol content 96.8%.
Embodiment 5:
Get that turpentine distilling goes out containing fenchol by product 10kg, proterties is weak yellow liquid, has the camphoraceous fragrance of class, and main component is alpha-terpineol 2.3%, phantol 29.8%, fenchol 58.4%.Get the saturated solution that gac puts into tosic acid, dipping 10h after, filter, then gac is put into oven drying, temperature controls at 110 DEG C, and time of drying is 3h, obtain activated carbon supported after toluenesulphonic acids.
To add in reactor containing fenchol by product, add material weight concentration 0.1Kg activated carbon supported after toluenesulphonic acids, stir, temperature of reaction controls at 100 DEG C, reaction times 2h.After catalyzed reaction, the reactant obtained is cooled to room temperature, then adds sig water neutralization, staticly settle, isolate water layer and oil reservoir, isolated oil-reservoir water is washed till neutrality.Oil reservoir is dropped into rectifying tower, and control vacuum tightness <-0.09MPa, tower top temperature controls at 114-120 DEG C, with reflux ratio 6:1, obtains the fenchol primary products of purity >=80%.Again the fenchol primary products obtained are put into freezer crystallization 15h, temperature of ice house control for≤-15 DEG C.Fenchol primary products after crystallization are carried out low-temperature centrifugation separation, and the temperature of separation controls, for < 0 DEG C, rotating speed > 5000r/min, to obtain the product of fenchol content 97.0%.
Embodiment 6:
Get that turpentine distilling goes out containing fenchol by product 10.1kg, proterties is weak yellow liquid, has the camphoraceous fragrance of class, and main component is alpha-terpineol 4.5%, phantol 28.6%, fenchol 53.8%.Getting conventional activated carbon, to put into volumetric concentration be 60% dilute sulphuric acid, and dipping 5h, filters, then the gac being adsorbed with dilute sulphuric acid is put into baking oven and toast 2h at 150 DEG C, obtain carrier active carbon.Carrier active carbon is put into the saturated solution of tosic acid again, after dipping 20h, filter, then put into oven drying by flooding the gac that obtains, temperature controls at 115 DEG C, and time of drying is 2h, obtain activated carbon supported after toluenesulphonic acids.
To add in reactor containing fenchol by product, add material weight concentration 0.3Kg activated carbon supported after toluenesulphonic acids, stir, temperature of reaction controls at 100 DEG C, reaction times 2h.After catalyzed reaction, the reactant obtained is cooled to room temperature, then adds sig water neutralization, staticly settle, isolate water layer and oil reservoir, isolated oil-reservoir water is washed till neutrality.Oil reservoir is dropped into rectifying tower, and control vacuum tightness <-0.09MPa, tower top temperature controls at 114-120 DEG C, with reflux ratio 4:1, obtains the fenchol primary products of purity >=80%.Again the fenchol primary products obtained are put into freezer crystallization 15h, temperature of ice house control for≤-15 DEG C.Fenchol primary products after crystallization are carried out low-temperature centrifugation separation, and the temperature of separation controls, for < 0 DEG C, rotating speed > 5000r/min, to obtain the product of fenchol content 96.9%.
Embodiment 7:
Get that turpentine distilling goes out containing fenchol by product 10kg, proterties is weak yellow liquid, has the camphoraceous fragrance of class, and main component is alpha-terpineol 4.5%, phantol 28.6%, fenchol 53.8%.Getting conventional activated carbon, to put into volumetric concentration be 30% dilute sulphuric acid, and dipping 8h, filters, then the gac being adsorbed with dilute sulphuric acid is put into baking oven and toast 3h at 120 DEG C, obtain carrier active carbon.Carrier active carbon is put into the saturated solution of tosic acid again, after dipping 10h, filter, then put into oven drying by flooding the gac that obtains, temperature controls at 110 DEG C, and time of drying is 3h, obtain activated carbon supported after toluenesulphonic acids.
To add in reactor containing fenchol by product, add material weight concentration 0.2Kg activated carbon supported after toluenesulphonic acids, stir, temperature of reaction controls at 50 DEG C, reaction times 3h.After catalyzed reaction, the reactant obtained is cooled to room temperature, then adds sig water neutralization, staticly settle, isolate water layer and oil reservoir, isolated oil-reservoir water is washed till neutrality.Oil reservoir is dropped into rectifying tower, and control vacuum tightness <-0.09MPa, tower top temperature controls at 114-120 DEG C, with reflux ratio 6:1, obtains the fenchol primary products of purity >=80%.Again the fenchol primary products obtained are put into freezer crystallization 15h, temperature of ice house control for≤-15 DEG C.Fenchol primary products after crystallization are carried out low-temperature centrifugation separation, and the temperature of separation controls, for < 0 DEG C, rotating speed > 5000r/min, to obtain the product of fenchol content 96.7%.
Embodiment 8:
Get that turpentine distilling goes out containing fenchol by product 10kg, proterties is weak yellow liquid, has the camphoraceous fragrance of class, and main component is alpha-terpineol 8.1%, phantol 30%, fenchol 51.8%.With saturated ferrum sulfuricum oxydatum solutum and sulfuric acid by weight be saturated ferrum sulfuricum oxydatum solutum: sulfuric acid=2: 7 prepares ferric sulfate mixed solution, this mixed solution is for being acidity.Get gac and put into ferric sulfate mixed solution, dipping 5h, filters, the carrier active carbon water being adsorbed with ferric sulfate is cleaned 2 times, is then filtered dry water, put into baking oven and toast 2h at 150 DEG C, obtain carrier active carbon.Carrier active carbon is put into the saturated solution of tosic acid again, after dipping 10h, filter, then put into oven drying by flooding the gac that obtains, temperature controls at 110 DEG C, and time of drying is 3h, obtain activated carbon supported after toluenesulphonic acids.
To add in reactor containing fenchol by product, add material weight concentration 0.02Kg activated carbon supported after toluenesulphonic acids, stir, temperature of reaction controls at 50 DEG C, reaction times 3h.After catalyzed reaction, the reactant obtained is cooled to room temperature, then adds sig water neutralization, staticly settle, isolate water layer and oil reservoir, isolated oil-reservoir water is washed till neutrality.Oil reservoir is dropped into rectifying tower, and control vacuum tightness <-0.09MPa, tower top temperature controls at 114-120 DEG C, with reflux ratio 5:1, obtains the fenchol primary products of purity >=80%.Again the fenchol primary products obtained are put into freezer crystallization 15h, temperature of ice house control for≤-15 DEG C.Fenchol primary products after crystallization are carried out low-temperature centrifugation separation, and the temperature of separation controls, for < 0 DEG C, rotating speed > 5000r/min, to obtain the product of fenchol content 97.4%.
Embodiment 9:
Get that turpentine distilling goes out containing fenchol by product 10kg, proterties is weak yellow liquid, has the camphoraceous fragrance of class, and main component is alpha-terpineol 8.1%, phantol 30%, fenchol 51.8%.With saturated ferrum sulfuricum oxydatum solutum and sulfuric acid by weight be saturated ferrum sulfuricum oxydatum solutum: sulfuric acid=3: 7 prepares ferric sulfate mixed solution, this mixed solution is for being acidity.Get gac and put into ferric sulfate mixed solution, dipping 8h, filters, the carrier active carbon water being adsorbed with ferric sulfate is cleaned 3 times, is then filtered dry water, put into baking oven and toast 1h at 180 DEG C, obtain carrier active carbon.Carrier active carbon is put into the saturated solution of tosic acid again, after dipping 20h, filter, then put into oven drying by flooding the gac that obtains, temperature controls at 115 DEG C, and time of drying is 2h, obtain activated carbon supported after toluenesulphonic acids.
To add in reactor containing fenchol by product, add material weight concentration 0.15Kg activated carbon supported after toluenesulphonic acids, stir, temperature of reaction controls at 80 DEG C, reaction times 3h.After catalyzed reaction, the reactant obtained is cooled to room temperature, then adds sig water neutralization, staticly settle, isolate water layer and oil reservoir, isolated oil-reservoir water is washed till neutrality.Oil reservoir is dropped into rectifying tower, and control vacuum tightness <-0.09MPa, tower top temperature controls at 114-120 DEG C, with reflux ratio 4:1, obtains the fenchol primary products of purity >=80%.Again the fenchol primary products obtained are put into freezer crystallization 15h, temperature of ice house control for≤-15 DEG C.Fenchol primary products after crystallization are carried out low-temperature centrifugation separation, and the temperature of separation controls, for < 0 DEG C, rotating speed > 5000r/min, to obtain the product of fenchol content 97.7%.
Embodiment 10:
Get that turpentine distilling goes out containing fenchol by product 10kg, proterties is weak yellow liquid, has the camphoraceous fragrance of class, and main component is alpha-terpineol 4.4%, phantol 28.3%, fenchol 53.5%.With saturated ferrum sulfuricum oxydatum solutum and sulfuric acid by weight be saturated ferrum sulfuricum oxydatum solutum: sulfuric acid=2.5: 7.5 prepares ferric sulfate mixed solution, this mixed solution is for being acidity.Get gac and put into ferric sulfate mixed solution, dipping 6h, filters, the carrier active carbon water being adsorbed with ferric sulfate is cleaned 3 times, is then filtered dry water, put into baking oven and toast 1.5h at 160 DEG C, obtain carrier active carbon.Carrier active carbon is put into the saturated solution of tosic acid again, after dipping 15h, filter, then put into oven drying by flooding the gac that obtains, temperature controls at 115 DEG C, and time of drying is 2h, obtain activated carbon supported after toluenesulphonic acids.
To add in reactor containing fenchol by product, add material weight concentration 0.05Kg activated carbon supported after toluenesulphonic acids, stir, temperature of reaction controls at 100 DEG C, reaction times 2h.After catalyzed reaction, the reactant obtained is cooled to room temperature, then adds sig water neutralization, staticly settle, isolate water layer and oil reservoir, isolated oil-reservoir water is washed till neutrality.Oil reservoir is dropped into rectifying tower, and control vacuum tightness <-0.09MPa, tower top temperature controls at 114-120 DEG C, with reflux ratio 6:1, obtains the fenchol primary products of purity >=80%.Again the fenchol primary products obtained are put into freezer crystallization 15h, temperature of ice house control for≤-15 DEG C.Fenchol primary products after crystallization are carried out low-temperature centrifugation separation, and the temperature of separation controls, for < 0 DEG C, rotating speed > 5000r/min, to obtain the product of fenchol content 97.8%.
Claims (5)
1. one kind contains from turps the method extracting high-purity natural fenchol fenchol by product, described mainly contains the monoterpene such as phantol, fenchol alcohol mixture containing fenchol by product, wherein the content of fenchol is 50-60%, it is characterized in that: carry out catalyzed reaction at turps containing adding an acidic catalyst tosic acid in fenchol by product, after the standing oil reservoir obtained of neutralization is washed, again by rectifying and freezing and crystallizing, last low-temperature centrifugation is separated, and obtains the natural fenchol product of purity > 96%; Concrete operation step is as follows:
(1) catalyzed reaction: will add in reactor containing fenchol by product, adds an acidic catalyst tosic acid of material weight concentration 0.2-3%, and stir, temperature of reaction controls at 50-100 DEG C, reaction times 2-3h;
(2) wash: the reactant that step (1) obtains is cooled to room temperature, then add sig water neutralization, staticly settle, isolate water layer and oil reservoir, isolated oil-reservoir water is washed till neutrality;
(3) rectifying: the oil reservoir after step (2) being washed drops into rectifying tower, vacuum tightness <-0.09MPa, and tower top temperature controls at 114-120 DEG C, with reflux ratio 4:1-6:1, obtains the fenchol primary products of purity >=80%;
(4) freezing and crystallizing: the fenchol primary products that step (3) obtains are put into freezer crystallization 15h, temperature of ice house control for≤-15 DEG C;
(5) centrifugation: the fenchol primary products after step (4) crystallization are carried out low-temperature centrifugation separation, the temperature be separated controls as < 0 DEG C, rotating speed > 5000r/min, obtains the product of fenchol content > 96%.
2. according to claim 1 a kind of from turps containing the method extracting high-purity natural fenchol fenchol by product, it is characterized in that: an acidic catalyst tosic acid described in step (1) is that load is on carrier active carbon, concrete carrying method is saturated solution carrier active carbon being put into tosic acid, after dipping 10-20h, filter, then carrier active carbon is put into oven drying, temperature controls at 110-115 DEG C, time of drying is 2-3h, obtain activated carbon supported after toluenesulphonic acids.
3. according to claim 2 a kind of from turps containing the method extracting high-purity natural fenchol fenchol by product, it is characterized in that: described carrier active carbon is through the impregnated gac of sulfuric acid, concrete dipping method is that conventional activated carbon to be put into volumetric concentration be 30-60% dilute sulphuric acid, dipping 5-8h, filter, then the gac being adsorbed with dilute sulphuric acid is put into baking oven and toast 2-3h at 120-150 DEG C, obtain carrier active carbon.
4. according to claim 2 a kind of from turps containing the method extracting high-purity natural fenchol fenchol by product, it is characterized in that: described carrier active carbon is through the impregnated gac of ferric sulfate mixed solution, concrete dipping method is that conventional activated carbon is put into ferric sulfate mixed solution, dipping 5-8h, filter, the gac water being adsorbed with ferric sulfate is cleaned 2-3 time, is then filtered dry water, put into baking oven and toast 1-2h at 150-180 DEG C, obtain carrier active carbon.
5. according to claim 4 a kind of from turps containing the method extracting high-purity natural fenchol fenchol by product, it is characterized in that: described ferric sulfate mixed solution is the mixing solutions of saturated ferrum sulfuricum oxydatum solutum and sulfuric acid, its weight ratio is saturated ferrum sulfuricum oxydatum solutum: sulfuric acid=2-3: 7-8, and mixed solution is for being acidity.
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| CN110698323A (en) * | 2019-09-10 | 2020-01-17 | 云南林缘香料有限公司 | Method for extracting high-purity fenchyl alcohol from alcohol mixture as by-product in production of borneol |
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| CN110698323A (en) * | 2019-09-10 | 2020-01-17 | 云南林缘香料有限公司 | Method for extracting high-purity fenchyl alcohol from alcohol mixture as by-product in production of borneol |
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Application publication date: 20160203 Assignee: Guangxi Luchuan Lizizhai Breeding Professional Cooperative Assignor: GUANGXI ZHUANG AUTONOMOUS REGION FORESTRY Research Institute Contract record no.: X2023980045112 Denomination of invention: A method for extracting high-purity natural fenpropanol from by-products of turpentine oil containing fenpropanol Granted publication date: 20170322 License type: Common License Record date: 20231031 |