CN113480498A - Biomass-based gamma-octadecanolide synthesis method - Google Patents
Biomass-based gamma-octadecanolide synthesis method Download PDFInfo
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- 239000002028 Biomass Substances 0.000 title claims abstract description 17
- 238000001308 synthesis method Methods 0.000 title description 3
- 239000000654 additive Substances 0.000 claims abstract description 23
- 230000000996 additive effect Effects 0.000 claims abstract description 23
- 238000001035 drying Methods 0.000 claims abstract description 20
- 238000002156 mixing Methods 0.000 claims abstract description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000008367 deionised water Substances 0.000 claims abstract description 16
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 11
- 239000002904 solvent Substances 0.000 claims abstract description 11
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims abstract description 9
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims abstract description 9
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000005642 Oleic acid Substances 0.000 claims abstract description 9
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims abstract description 9
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims abstract description 9
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims abstract description 9
- 238000010189 synthetic method Methods 0.000 claims abstract description 7
- 239000000706 filtrate Substances 0.000 claims abstract description 6
- 238000001914 filtration Methods 0.000 claims abstract description 6
- 238000010438 heat treatment Methods 0.000 claims abstract description 6
- 239000012074 organic phase Substances 0.000 claims abstract description 6
- 238000010992 reflux Methods 0.000 claims abstract description 6
- 239000003513 alkali Substances 0.000 claims description 17
- 239000007787 solid Substances 0.000 claims description 12
- 238000005406 washing Methods 0.000 claims description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- GYDWWIHJZSCRGV-UHFFFAOYSA-N 5-tetradecyloxolan-2-one Chemical compound CCCCCCCCCCCCCCC1CCC(=O)O1 GYDWWIHJZSCRGV-UHFFFAOYSA-N 0.000 claims description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 6
- 238000007873 sieving Methods 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 239000012153 distilled water Substances 0.000 claims description 4
- 230000007935 neutral effect Effects 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims 6
- 230000015572 biosynthetic process Effects 0.000 abstract description 6
- 238000003786 synthesis reaction Methods 0.000 abstract description 6
- 239000002994 raw material Substances 0.000 abstract description 5
- 239000000047 product Substances 0.000 abstract description 4
- 239000002304 perfume Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 7
- 238000001816 cooling Methods 0.000 description 3
- 239000003205 fragrance Substances 0.000 description 3
- 235000019645 odor Nutrition 0.000 description 3
- 235000013599 spices Nutrition 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 241000208125 Nicotiana Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000015173 baked goods and baking mixes Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- -1 carbon cations Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 235000011850 desserts Nutrition 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
- 125000000457 gamma-lactone group Chemical group 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 235000019614 sour taste Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Seasonings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention relates to a synthetic method based on biomass-based gamma-octadecanolactone, which belongs to the technical field of perfume synthesis and specifically comprises the following steps: firstly, mixing a solvent and oleic acid, adding a catalyst and an additive at the temperature of 0-5 ℃, and heating and refluxing for 8-10 hours at the temperature of 70-85 ℃; and step two, after the reaction is finished, filtering, extracting the filtrate by using deionized water and diethyl ether, concentrating the obtained organic phase under reduced pressure, and drying to obtain the gamma-octadecanolactone. The invention also prepares an additive in the synthesis process, the additive takes the diatomite as a raw material, the micropore structure of the diatomite is more uniform after roasting, the peculiar smell generated in the reaction process can be better absorbed, and the product quality is improved.
Description
Technical Field
The invention belongs to the technical field of spice synthesis, and particularly relates to a biomass-based gamma-octadecanolide-based synthesis method.
Background
Saturated gamma-lactone compounds naturally exist in various fruits, are a very important edible flavor, and are widely used in various beverages, baked goods and desserts. The gamma-octadecanolide is a common spice substance in the daily chemical industry field, has fruit fragrance, and has the characteristics of lasting fragrance, soft fragrance, aroma enhancement and the like, so the gamma-octadecanolide is widely applied to the fields of foods, daily cosmetics, tobacco spices and the like.
The gamma-octadecanolide prepared in the existing synthesis process has obvious plastic odor or sour taste, which affects the quality of the gamma-octadecanolide.
Disclosure of Invention
The invention aims to provide a synthetic method based on biomass-based gamma-octadecanolide.
The purpose of the invention can be realized by the following technical scheme:
a synthetic method based on biomass-based gamma-octadecanolide comprises the following steps:
firstly, mixing a solvent and oleic acid, adding a catalyst and an additive at the temperature of 0-5 ℃, and heating and refluxing for 8-10 hours at the temperature of 70-85 ℃;
and step two, after the reaction is finished, filtering, extracting the filtrate by using deionized water and diethyl ether, concentrating the obtained organic phase under reduced pressure, and drying to obtain the gamma-octadecanolactone. In the reaction process, double bonds in oleic acid molecules firstly migrate, and under the action of a catalyst, carbon cations are quickly shifted from delta 9 to delta 4, and carbon chains are cyclized to generate gamma-octadecanolactone.
The reaction process is as follows:
further, the catalyst is one of concentrated sulfuric acid with a mass fraction of 98% and perchloric acid with a mass fraction of 70%.
Further, the solvent is one of n-hexane and chloroform.
Further, the temperature at the time of drying is 30 to 40 ℃.
Further, the additive is prepared by the following steps:
step S11, mixing diatomite and deionized water, stirring and mixing for 30-50min at 50-75 ℃, then sieving with a 100-mesh sieve, drying at 40 ℃ to constant weight, roasting for 2h at 800 ℃ at 700-;
and step S12, mixing the solid A and an alkali solution, reacting for 1h at the temperature of 50-60 ℃, washing the reacted solution with distilled water after the reaction is finished until the washing solution is neutral, and drying to constant weight at the temperature of 40 ℃ after the washing is finished to obtain the additive.
Further, in the step S11, the mass ratio of the diatomite to the deionized water is 1: 20.
further, the alkali solution in the step S12 is one of a sodium hydroxide aqueous solution and ammonia water, and the mass fraction of the alkali solution is 15%; the dosage ratio of the solid A to the alkali solution is 1 g: 3 mL.
The invention has the beneficial effects that:
the method takes biomass-based oleic acid as a raw material to prepare the gamma-octadecalactone, double bonds in oleic acid molecules are firstly transferred in the reaction process, and carbon chains are cyclized to generate the gamma-octadecalactone when carbocation is rapidly shifted from delta 9 to delta 4 under the action of a catalyst. The additive is prepared in the synthesis process, diatomite is used as a raw material, the micropore structure of the diatomite is more uniform after roasting, peculiar smell generated in the reaction process can be better absorbed, the product quality is improved, the synthesis procedures are reduced, on the other hand, alkali solution can react with metal oxide in the diatomite, the content of the metal oxide is reduced, the content of silicon dioxide is increased, the silicon dioxide has a certain catalytic effect on the isomerization reaction of olefin, and the product yield is improved.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
Preparing an additive:
step S11, mixing diatomite and deionized water, stirring and mixing for 30min at 50 ℃, then sieving with a 100-mesh sieve, drying at 40 ℃ to constant weight, roasting at 700 ℃ for 2h, and cooling to room temperature to obtain solid A; wherein the mass ratio of the diatomite to the deionized water is 1: 20;
and step S12, mixing the solid A and an alkali solution, reacting for 1h at the temperature of 50 ℃, washing the reacted solution with distilled water after the reaction is finished until the washing liquid is neutral, and drying to constant weight at the temperature of 40 ℃ after the washing is finished to obtain the additive. The aqueous alkali is sodium hydroxide aqueous solution, and the mass fraction of the aqueous alkali is 15%; the dosage ratio of the solid A to the alkali solution is 1 g: 3 mL.
Example 2
Preparing an additive:
step S11, mixing diatomite and deionized water, stirring and mixing for 50min at 75 ℃, then sieving with a 100-mesh sieve, drying at 40 ℃ to constant weight, roasting at 800 ℃ for 2h, and cooling to room temperature to obtain solid A; wherein the mass ratio of the diatomite to the deionized water is 1: 20;
and step S12, mixing the solid A and an alkali solution, reacting for 1h at the temperature of 60 ℃, washing the reacted solution with distilled water after the reaction is finished until the washing liquid is neutral, and drying to constant weight at the temperature of 40 ℃ after the washing is finished to obtain the additive. The aqueous alkali is ammonia, and the mass fraction of the aqueous alkali is 15%; the dosage ratio of the solid A to the alkali solution is 1 g: 3 mL.
Example 3
The synthetic method based on biomass-based gamma-octadecanolide comprises the following steps:
firstly, mixing a solvent and oleic acid, adding a catalyst and an additive at the temperature of 0 ℃, and heating and refluxing for 8 hours at the temperature of 70 ℃;
and step two, after the reaction is finished, filtering, extracting the filtrate by using deionized water and diethyl ether, concentrating the obtained organic phase under reduced pressure, and drying to obtain the gamma-octadecanolactone.
Wherein the catalyst is concentrated sulfuric acid with the mass fraction of 98%; the solvent is n-hexane. The temperature during drying was 30 ℃. The additive was prepared as in example 1.
Example 4
A synthetic method based on biomass-based gamma-octadecanolide comprises the following steps:
firstly, mixing a solvent and oleic acid, adding a catalyst and an additive at the temperature of 0 ℃, and heating and refluxing for 9 hours at the temperature of 80 ℃;
and step two, after the reaction is finished, filtering, extracting the filtrate by using deionized water and diethyl ether, concentrating the obtained organic phase under reduced pressure, and drying to obtain the gamma-octadecanolactone.
Wherein the catalyst is concentrated sulfuric acid with the mass fraction of 98%. The solvent is n-hexane. The temperature during drying was 30 ℃. The additive was prepared as in example 1.
Example 5
A synthetic method based on biomass-based gamma-octadecanolide comprises the following steps:
firstly, mixing a solvent and oleic acid, adding a catalyst and an additive at the temperature of 5 ℃, and heating and refluxing for 10 hours at the temperature of 85 ℃;
and step two, after the reaction is finished, filtering, extracting the filtrate by using deionized water and diethyl ether, concentrating the obtained organic phase under reduced pressure, and drying to obtain the gamma-octadecanolactone.
Wherein the catalyst is perchloric acid with the mass fraction of 70%. The solvent is chloroform. The temperature during drying was 40 ℃. The additive was prepared as in example 1.
Comparative example 1
Preparing an additive:
step S11, mixing diatomite and deionized water, stirring and mixing for 30min at 50 ℃, then sieving with a 100-mesh sieve, drying at 40 ℃ to constant weight, roasting at 700 ℃ for 2h, and cooling to room temperature to obtain solid A; wherein the mass ratio of the diatomite to the deionized water is 1: 20;
comparative example 2
The additive of example 4 was replaced with solid a prepared in comparative example 1, and the remaining raw materials and preparation process were kept unchanged.
Comparative example 3
The additive of example 4 was not added, and the remaining raw materials and preparation process remained unchanged.
The yields of the samples prepared in examples 3 to 5 and comparative examples 2 to 3, and the odors of the samples were measured; the results are shown in table 1 below:
TABLE 1
| Example 3 | Example 4 | Example 5 | Comparative example 2 | Comparative example 3 | |
| Smell(s) | No plastic smell | No plastic smell | No plastic smell | No plastic smell | Has plastic smell |
| Yield/% | 78.2 | 78.9 | 78.4 | 68.8 | 68.2 |
As can be seen from Table 1 above, the product obtained in the present invention has a better odor and a higher yield.
In the description herein, references to the description of "one embodiment," "an example," "a specific example" or the like are intended to mean that a particular feature, structure, material, or characteristic described in connection with the embodiment or example is included in at least one embodiment or example of the invention. In this specification, the schematic representations of the terms used above do not necessarily refer to the same embodiment or example. Furthermore, the particular features, structures, materials, or characteristics described may be combined in any suitable manner in any one or more embodiments or examples.
The foregoing is illustrative and explanatory only and is not intended to be exhaustive or to limit the invention to the precise embodiments described, and various modifications, additions, and substitutions may be made by those skilled in the art without departing from the scope of the invention or exceeding the scope of the claims.
Claims (7)
1. A synthetic method based on biomass-based gamma-octadecanolide is characterized by comprising the following steps:
firstly, mixing a solvent and oleic acid, adding a catalyst and an additive at the temperature of 0-5 ℃, and heating and refluxing for 8-10 hours at the temperature of 70-85 ℃;
and step two, after the reaction is finished, filtering, extracting the filtrate by using deionized water and diethyl ether, concentrating the obtained organic phase under reduced pressure, and drying to obtain the gamma-octadecanolactone.
2. The method for synthesizing gamma-octadecalactone based on biomass according to claim 1, wherein the catalyst is one of concentrated sulfuric acid with a mass fraction of 98% and perchloric acid with a mass fraction of 70%.
3. The method for synthesizing gamma-octadecalactone based on biomass according to claim 1, wherein the solvent is one of n-hexane and chloroform.
4. The method for synthesizing gamma-octadecalactone based on biomass according to claim 1, wherein the temperature for drying is 30-40 ℃.
5. The method for synthesizing gamma-octadecalactone based on biomass according to claim 1, wherein the additive is prepared by the following steps:
step S11, mixing diatomite and deionized water, stirring and mixing for 30-50min at 50-75 ℃, then sieving with a 100-mesh sieve, drying at 40 ℃ to constant weight, roasting for 2h at 800 ℃ at 700-;
and step S12, mixing the solid A and an alkali solution, reacting for 1h at the temperature of 50-60 ℃, washing the reacted solution with distilled water after the reaction is finished until the washing solution is neutral, and drying to constant weight at the temperature of 40 ℃ after the washing is finished to obtain the additive.
6. The method for synthesizing gamma-octadecalactone based on biomass according to claim 5, wherein the mass ratio of the diatomite to the deionized water in step S11 is 1: 20.
7. the method for synthesizing gamma-octadecalactone based on biomass according to claim 5, wherein the alkali solution in step S12 is one of sodium hydroxide solution and ammonia water, and the mass fraction of the alkali solution is 15%; the dosage ratio of the solid A to the alkali solution is 1 g: 3 mL.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4062786A (en) * | 1976-09-24 | 1977-12-13 | Exxon Research And Engineering Company | Lactone oxazolines as oleaginous additives |
| EP2241562A1 (en) * | 2009-03-31 | 2010-10-20 | Cognis IP Management GmbH | Process for the production of lactones |
| CN105693658A (en) * | 2016-03-14 | 2016-06-22 | 江南大学 | Stearolactone synthesis process |
| US20180186716A1 (en) * | 2016-12-29 | 2018-07-05 | The United States Of America, As Represented By The Secretary Of Agriculture | Saturated branched chain fatty acid production method |
-
2021
- 2021-07-26 CN CN202110844784.6A patent/CN113480498B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4062786A (en) * | 1976-09-24 | 1977-12-13 | Exxon Research And Engineering Company | Lactone oxazolines as oleaginous additives |
| EP2241562A1 (en) * | 2009-03-31 | 2010-10-20 | Cognis IP Management GmbH | Process for the production of lactones |
| CN105693658A (en) * | 2016-03-14 | 2016-06-22 | 江南大学 | Stearolactone synthesis process |
| US20180186716A1 (en) * | 2016-12-29 | 2018-07-05 | The United States Of America, As Represented By The Secretary Of Agriculture | Saturated branched chain fatty acid production method |
Non-Patent Citations (4)
| Title |
|---|
| JOHN S. SHOWELL等: "Perchloric acid isomerization of oleic acid", 《J. ORG. CHEM.》 * |
| STEVEN C. CERMAK等: "Synthesis of δ-Stearolactone from Oleic Acid", 《JAOCS》 * |
| YIBO ZHOU等: "Solid acid catalysis of tandem isomerization-lactonization of olefinic acids", 《APPLIED CATALYSIS, A: GENERAL》 * |
| 倪邦庆等: "催化油酸内酯化反应合成硬脂酸内酯", 《中国油脂》 * |
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