CN101921191A - Preparation method for synthesizing isobornyl acetate by esterification of camphene and acetic acid - Google Patents
Preparation method for synthesizing isobornyl acetate by esterification of camphene and acetic acid Download PDFInfo
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- CN101921191A CN101921191A CN2010102933931A CN201010293393A CN101921191A CN 101921191 A CN101921191 A CN 101921191A CN 2010102933931 A CN2010102933931 A CN 2010102933931A CN 201010293393 A CN201010293393 A CN 201010293393A CN 101921191 A CN101921191 A CN 101921191A
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- acetate
- camphene
- hmcm
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- CRPUJAZIXJMDBK-UHFFFAOYSA-N camphene Chemical compound C1CC2C(=C)C(C)(C)C1C2 CRPUJAZIXJMDBK-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- KGEKLUUHTZCSIP-UHFFFAOYSA-N Isobornyl acetate Natural products C1CC2(C)C(OC(=O)C)CC1C2(C)C KGEKLUUHTZCSIP-UHFFFAOYSA-N 0.000 title claims abstract description 14
- PXRCIOIWVGAZEP-UHFFFAOYSA-N Primaeres Camphenhydrat Natural products C1CC2C(O)(C)C(C)(C)C1C2 PXRCIOIWVGAZEP-UHFFFAOYSA-N 0.000 title claims abstract description 11
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 229930006739 camphene Natural products 0.000 title claims abstract description 11
- ZYPYEBYNXWUCEA-UHFFFAOYSA-N camphenilone Natural products C1CC2C(=O)C(C)(C)C1C2 ZYPYEBYNXWUCEA-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 230000032050 esterification Effects 0.000 title claims abstract description 10
- 238000005886 esterification reaction Methods 0.000 title claims abstract description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title abstract description 12
- 230000002194 synthesizing effect Effects 0.000 title abstract description 3
- WWJLCYHYLZZXBE-UHFFFAOYSA-N 5-chloro-1,3-dihydroindol-2-one Chemical compound ClC1=CC=C2NC(=O)CC2=C1 WWJLCYHYLZZXBE-UHFFFAOYSA-N 0.000 title abstract 5
- 239000001940 [(1R,4S,6R)-1,7,7-trimethyl-6-bicyclo[2.2.1]heptanyl] acetate Substances 0.000 title abstract 5
- 238000006243 chemical reaction Methods 0.000 claims abstract description 41
- 239000003054 catalyst Substances 0.000 claims abstract description 13
- 239000002994 raw material Substances 0.000 claims abstract description 8
- 239000002808 molecular sieve Substances 0.000 claims abstract description 7
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims abstract description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 16
- 238000003786 synthesis reaction Methods 0.000 claims description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 12
- -1 isoborneol ester Chemical class 0.000 claims description 12
- DTGKSKDOIYIVQL-MRTMQBJTSA-N Isoborneol Natural products C1C[C@@]2(C)[C@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-MRTMQBJTSA-N 0.000 claims description 11
- CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Natural products C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 claims description 11
- 238000013329 compounding Methods 0.000 claims description 11
- DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 9
- 229910021536 Zeolite Inorganic materials 0.000 claims description 8
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 8
- 239000010457 zeolite Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- 229910052680 mordenite Inorganic materials 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000012295 chemical reaction liquid Substances 0.000 claims 2
- 230000000694 effects Effects 0.000 abstract description 3
- 238000011031 large-scale manufacturing process Methods 0.000 abstract 1
- 238000005516 engineering process Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 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 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 241000723346 Cinnamomum camphora Species 0.000 description 3
- 229930008380 camphor Natural products 0.000 description 3
- 229960000846 camphor Drugs 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 229930004069 diterpene Natural products 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000010815 organic waste Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention relates to a preparation method for synthesizing isobornyl acetate by esterification of camphene and acetic acid. A synthesized molecular sieve is taken as a catalyst; the raw materials camphene and acetic acid are proportionally added into a fixed bed tubular reactor or reaction kettle respectively for reaction to obtain the target product isobornyl acetate. The invention has the advantages of mild reaction conditions, high catalyst activity, high selectivity of isobornyl acetate and is environmentally friendly and can be widely applied to industrial large-scale production of isobornyl acetate.
Description
Technical field
The present invention relates to the preparation method of a kind of amphene and acid esterification synthesis of acetic acid Isobornyl.
Background technology
Compounding acetic isoborneol ester is the important intermediate of artificial camphor process, mainly is to be that raw material obtains by esterification with amphene and acetate.Camphor is a kind of terpenoid, belongs to bicyclic diterpene, is widely used in the daily life, because the natural camphor scarcity, artificial camphor comes into one's own day by day, and synthesizing of its intermediate compounding acetic isoborneol ester is also more and more important.
The reaction of industrial amphene and acid esterification synthesis of acetic acid Isobornyl adopts sulfuric acid, ionic membrane, Zeo-karb etc. to make catalyzer more.There are shortcomings such as equipment corrosion is serious, environmental pollution big, aftertreatment trouble in the technology of traditional with sulfuric acid is catalyzer, and is superseded substantially at present.With the sulfonic acid type ion film is the intermittent reaction technology of catalyzer, has shortcomings such as labour intensity is big, environment is poor, once through yield is low, therefore needs exploitation to adopt the continuous reaction technology of new catalyst to replace.It is the method for catalyzer synthesis of acetic acid Isobornyl that Chinese patent CN101372453A has described with the acidic cation-exchange resin, adopts continuous fixed bed reaction or continuous technology, at 40 ℃ of temperature of reaction, air speed 1.2h
-1, acetate and amphene mass ratio be under 1.5 the condition, the once through yield 88.6% of compounding acetic isoborneol ester.Though this method has obtained higher once through yield, the ion-exchange resin catalyst life-span is short, and can not regenerate behind the inactivation, has increased production cost, and produces a large amount of organic waste and need to handle, and has increased environmental burden.It is the method for catalyzer synthesis of acetic acid Isobornyl that Chinese patent CN1014056B has described with the natural mordenite zeolite, adopts the reverse-flow continuous reaction process of fixed bed, at 65 ℃ of temperature of reaction, air speed 0.04h
-1, acetate and amphene mol ratio be that the content of compounding acetic isoborneol ester is greater than 75% in the product under 1 the condition, the purity of compounding acetic isoborneol ester can be regenerated behind the catalyst deactivation greater than 90% after fractionation.Though this method catalyzer can be regenerated, guaranteed the life-time service of catalyzer, but product yield is low, by product is difficult to separate, and causes product purity low, and this method reaction velocity is low excessively, cause the device processing power little, increase investment and energy consumption, and the structure of natural mordenite zeolite, form that influenced by the place of production bigger, the instability of its performance and fluctuation can cause producing and be difficult to steady running.
Synthesis of molecular sieve is the material of a kind of structure, stable in properties, and pore structure that it is unique and surface acidity make it have good reactivity worth and regenerability, are used widely in reaction fields such as esterification, isomerization, hydrations.
Summary of the invention
Technical problem to be solved by this invention is to provide the preparation method of a kind of amphene and acid esterification synthesis of acetic acid Isobornyl.It is catalyzer that the present invention adopts synthesis of molecular sieve, the reaction conditions gentleness, and catalyst activity height, selectivity are good, environmental friendliness, solved the problem that existing technology exists effectively,, solved the problem that prior art exists effectively for the synthesis of acetic acid Isobornyl provides a kind of new effective way.
In order to reach above purpose, the present invention realizes by the following technical solutions.
The preparation method of described amphene and acid esterification synthesis of acetic acid Isobornyl, the catalyzer that adopts is a synthesis of molecular sieve, preferred Hydrogen, more preferably a kind of among HZSM-5, HZSM-22, HZSM-35, HMCM-49, HMCM-22, HMCM-56, HMCM-36, HMCM-41, HMCM-48, mordenite, H β zeolite, HY zeolite, SAPO-34 or the SAPO-11 or their mixture; With material camphene, acetate by 0.5～5.0: 1 mol ratio adds respectively in fixed-bed tube reactor or the stainless steel cauldron reacts, and promptly makes the target product compounding acetic isoborneol ester.
Wherein material camphene, the acetate reaction conditions in fixed-bed tube reactor is: temperature of reaction is 20～100 ℃, is preferably 30～70 ℃; The amphene air speed is 0.1～10.0h
-1, be preferably 0.5～8.0h
-1Reaction pressure is normal pressure～1.0MPa, is preferably normal pressure～0.5MPa.
Wherein the reaction conditions in material camphene, the acetic acidreaction still is: catalyst consumption is 1%～40% of a reaction solution quality, is preferably 3%～20%; 30～100 ℃ of temperature of reaction are preferably 30～70 ℃; In 2～10 hours reaction times, be preferably 2～7 hours; Reaction pressure is normal pressure～1.0MPa, is preferably normal pressure～0.5MPa.
It is catalyzer that the present invention adopts synthesis of molecular sieve, the reaction conditions gentleness, and the catalyst activity height, amphene transformation efficiency height is greatly improved the selectivity of compounding acetic isoborneol ester.This reaction conditions is environmentally friendly, thereby can be widely used in large-scale industrialization production compounding acetic isoborneol ester.
Embodiment
Below in conjunction with specific embodiment technical scheme of the present invention is described in further detail, but protection scope of the present invention is not limited to following specific embodiment.
Embodiment 1～5
Synthetic molecular sieve catalyst 100 gram is respectively charged into fixed-bed tube reactor, by a certain percentage amphene and acetic acid raw material is squeezed into reactor with volume pump and carry out synthesis under normal pressure, concrete reaction conditions and reaction result are referring to table 1.
Table 1
Embodiment 6～10
In 500 milliliters of stainless steel stirred autoclaves, the catalyzer that adds 300 gram mixing raw materials and a certain amount of (is basic calculation with the reaction raw materials) respectively by certain acetate/amphene mol ratio, heat up then and carry out synthesis under normal pressure, concrete reaction conditions and reaction result see Table 2.
Table 2
From above-mentioned table 1, table 2 as can be seen: owing to selected highly active catalyzer, make the selectivity of the compounding acetic isoborneol ester that preparation method of the present invention makes up to 95.6%, the amphene transformation efficiency is up to 92.6%, and this preparation method's reaction conditions gentleness, environmentally friendly, the industrialization that can be widely used in compounding acetic isoborneol ester is synthetic.
Should be noted that at last, above embodiment is only unrestricted in order to technical scheme of the present invention to be described, although the present invention is had been described in detail with reference to preferred embodiment, those of ordinary skill in the art is to be understood that, can make amendment or be equal to replacement the technical scheme of invention, and not breaking away from the spirit and scope of technical solution of the present invention, it all should be encompassed in the claim scope of the present invention.
Claims (8)
1. the preparation method of amphene and acid esterification synthesis of acetic acid Isobornyl, it is characterized in that, the catalyzer that adopts is a synthesis of molecular sieve, with material camphene, acetate by 0.5～5.0: 1 mol ratio adds respectively in fixed-bed tube reactor or the reactor reacts, and promptly makes the target product compounding acetic isoborneol ester.
2. preparation method according to claim 1 is characterized in that, described synthetic zeolite catalyst is a Hydrogen.
3. preparation method according to claim 1, it is characterized in that described synthetic zeolite catalyst is a kind of among HZSM-5, HZSM-22, HZSM-35, HMCM-49, HMCM-22, HMCM-56, HMCM-36, HMCM-41, HMCM-48, mordenite MOR, H β zeolite, HY zeolite, SAPO-34 or the SAPO-11 or their mixture.
4. preparation method according to claim 1 is characterized in that, the mol ratio preferred 0.5～3.0: 1 of described reaction raw materials amphene, acetate.
5. preparation method according to claim 1 is characterized in that, material camphene, the acetate reaction conditions in fixed-bed tube reactor is: 20～100 ℃ of temperature of reaction, amphene air speed are 0.1～10.0h
-1, reaction pressure is normal pressure～1.0MPa.
6. preparation method according to claim 5 is characterized in that, material camphene, acetate are preferred at the reaction conditions of fixed-bed tube reactor: 30～70 ℃ of temperature of reaction, amphene air speed are 0.5～8.0h
-1, reaction pressure is normal pressure～0.5MPa.
7. preparation method according to claim 1, it is characterized in that material camphene, the acetate reaction conditions in reactor is: catalyst consumption be raw material reaction liquid quality summation 1%～40%, 30～100 ℃ of temperature of reaction, 2～10 hours reaction times, reaction pressure be normal pressure～1.0MPa.
8. preparation method according to claim 7, it is characterized in that material camphene, the acetate reaction conditions in reactor is preferred: catalyst consumption be raw material reaction liquid quality summation 3%～20%, 30～70 ℃ of temperature of reaction, 2～7 hours reaction times, reaction pressure be normal pressure～0.5MPa.
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|---|---|---|---|
| CN 201010293393 CN101921191B (en) | 2010-09-27 | 2010-09-27 | Preparation method for synthesizing isobornyl acetate by esterification of camphene and acetic acid |
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| CN 201010293393 CN101921191B (en) | 2010-09-27 | 2010-09-27 | Preparation method for synthesizing isobornyl acetate by esterification of camphene and acetic acid |
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| CN101921191A true CN101921191A (en) | 2010-12-22 |
| CN101921191B CN101921191B (en) | 2013-04-10 |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104370740A (en) * | 2014-10-20 | 2015-02-25 | 上海华谊（集团）公司 | Production method of isobornyl acetate |
| CN104529770A (en) * | 2014-12-16 | 2015-04-22 | 上海华谊（集团）公司 | Preparation method of isobornyl acrylate or isobornyl methacrylate |
| CN106699617A (en) * | 2017-02-08 | 2017-05-24 | 南安格泰建材有限公司 | Preparation method of trimethylolpropane tris(3-mercaptopropionate) |
| CN107088437A (en) * | 2017-05-16 | 2017-08-25 | 云南森美达生物科技有限公司 | A kind of synthetic method of compounding acetic isoborneol ester catalyst for synthesizing and compounding acetic isoborneol ester |
| CN107899612A (en) * | 2017-12-08 | 2018-04-13 | 河南大学 | A kind of more acids ionic-liquid catalysts of functionalization, preparation method and catalyze and synthesize the method for compounding acetic isoborneol ester with it |
| CN115850068A (en) * | 2022-11-29 | 2023-03-28 | 广西壮族自治区林业科学研究院 | Long-chain fatty acid isobornyl ester synthesized by camphene, method and application thereof |
-
2010
- 2010-09-27 CN CN 201010293393 patent/CN101921191B/en active Active
Non-Patent Citations (1)
| Title |
|---|
| 陶阿建等: "用强酸树脂催化合成高含量乙酸异龙脑酯", 《上海化工》 * |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104370740A (en) * | 2014-10-20 | 2015-02-25 | 上海华谊（集团）公司 | Production method of isobornyl acetate |
| CN104370740B (en) * | 2014-10-20 | 2016-03-23 | 上海华谊（集团）公司 | Compounding acetic isoborneol ester production method |
| CN104529770A (en) * | 2014-12-16 | 2015-04-22 | 上海华谊（集团）公司 | Preparation method of isobornyl acrylate or isobornyl methacrylate |
| CN106699617A (en) * | 2017-02-08 | 2017-05-24 | 南安格泰建材有限公司 | Preparation method of trimethylolpropane tris(3-mercaptopropionate) |
| CN107088437A (en) * | 2017-05-16 | 2017-08-25 | 云南森美达生物科技有限公司 | A kind of synthetic method of compounding acetic isoborneol ester catalyst for synthesizing and compounding acetic isoborneol ester |
| CN107088437B (en) * | 2017-05-16 | 2020-04-03 | 云南森美达生物科技有限公司 | A kind of catalyst for synthesizing isobornyl acetate and method for synthesizing isobornyl acetate |
| CN107899612A (en) * | 2017-12-08 | 2018-04-13 | 河南大学 | A kind of more acids ionic-liquid catalysts of functionalization, preparation method and catalyze and synthesize the method for compounding acetic isoborneol ester with it |
| CN107899612B (en) * | 2017-12-08 | 2020-09-08 | 河南大学 | Functionalized polyacid ionic liquid catalyst, preparation method and method for catalytically synthesizing isobornyl acetate by using functionalized polyacid ionic liquid catalyst |
| CN115850068A (en) * | 2022-11-29 | 2023-03-28 | 广西壮族自治区林业科学研究院 | Long-chain fatty acid isobornyl ester synthesized by camphene, method and application thereof |
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| CN101921191B (en) | 2013-04-10 |
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