CN103285613B - A kind of total reflux reaction distilling apparatus and synthetic method thereof of synthesizing terpinol - Google Patents
A kind of total reflux reaction distilling apparatus and synthetic method thereof of synthesizing terpinol Download PDFInfo
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Abstract
Synthesize total reflux reaction distilling apparatus and the synthetic method thereof of terpinol, relate to terpinol.Described device is provided with evaporimeter, evaporating column, condenser coil, catalyst material basket, heating jacket.Condenser coil is put into catalyst material basket, then catalyst and θ ring stainless steel cloth filler mixed packing are entered in catalyst material basket, be fixed on evaporating column interior and closed; Close dispensing valve, raw material is added evaporimeter, close material inlet valve; To evaporimeter heating, raw material and solvent are evaporated and condensation in catalyst material basket, and condensate liquid contact catalyst carries out catalytic reaction; Product in catalyst material basket and unreacted raw material rely in evaporimeter at the bottom of gravity reflux to tower, and terpinol is deposited in evaporimeter, and condensation in catalyst material basket, then secondary response; As the content & lt of sample analysis firpene from evaporimeter; When 10%, stop heating, cessation reaction, opens dispensing valve, and discharges material carries out rectifying separation again, obtains terpinol.
Description
Technical field
The present invention relates to terpinol, especially relate to a kind of total reflux reaction distilling apparatus and synthetic method thereof of synthesizing terpinol.
Background technology
Terpinol is a kind of important chemical products, is widely used in the industry such as essence and flavoring agent, medicine, plastics, soap and telecommunication.The prior synthesizing method of terpinol is two step method ([1] Chen little Peng, Zhang Yunming. the research [J] of terpini hydras catalytic dehydration terpinol. Guangxi Chemical Industry, 1992,21 (3): 4-6), namely turpentine oil (main component is firpene) is under fluid sulphuric acid catalysis, obtain terpini hydras through the hydration of open loop isomery, then dewater to obtain terpinol, but this technique has that the production cycle is long, energy consumption is high, equipment corrosion and the shortcoming such as seriously polluted.The catalyst of some scholars to one-step method direct hydration terpinol conducts extensive research at present, attempt with organic acid catalyst, molecular sieve catalyst ([3] Takakom, Ryuichiroo, Naotoh, etal.Hydrationofpineneoverhydrophobiczeolitesin1,4-dioxanewaterandinwater [J] .MicroporousandMesoporousMaterials, 2007,101 (1/2): 176-183), solid super acid catalyst ([4] Chen Shaofeng, Guo Haifu, Yan Peng, etc. solid super-strong acid Ni/SO
4 2--SnO
2terpinol [J] is prepared in the hydration of catalysis firpene. chemistry world, 2009 (7): 430-435), cation exchange resin catalyst, ionic-liquid catalyst and film catalyst etc. replace fluid sulphuric acid catalyst.In one-step technology, turpentine oil direct hydration under acidic catalyst effect generates terpinol, this technique have with short production cycle, substantially there is not equipment corrosion and the advantages such as basic non-pollutant discharge, but the optimizing research of technical process and exploitation are not, the problem such as have that feed stock conversion is not high, product terpinol yield is lower, side reaction is more and process energy consumption is higher.
In recent years, domestic and international researcher is studied exploration to the reaction process of one-step synthesis method terpinol and synthetic method thereof, the catalyst adopted mainly contains solid acid and liquid acid, and reaction process mainly contains the technical process such as stirred-tank reactor catalysis method, injection-type reactor catalysis method and fixed bed reactors catalysis method.([2] RomanAguirreM such as Roman, DelaTorreSaenzL, WilberAntunezFlore, etal.Synthesisofterpineolfroma-pinenebyhomogeneousacidca talysis [J] .CatalysisToday, 2005,107-108:310-314) utilize stirred-tank reactor, have studied respectively with liquid acid hydrochloric acid, monoxone, oxalic acid and acetic acid as catalyst one-step synthesis method terpinol, result shows, and chloroacetic catalytic effect is best.When temperature is 70 DEG C, when water, firpene and chloroacetic mol ratio are 1: 2.4: 1.68, the conversion ratio of australene is 100%, and the yield of terpinol is 69.6%.But this method take liquid organic acid as catalyst, still there is follow-up separation process complexity, the problem such as equipment corrosion, " three wastes " are seriously polluted.([5] Yang Gaodong, Liu Yong, the Shao Yuyin such as Yang Gaodong, Zhou Zheng, Zhang Zhi is bright. turpentine oil direct hydration repercussion study [J]. and Chemical Engineering, 2010,18(12): 48-52) utilize pilot-scale injection-type reactor, catalyst is made with cationic ion-exchange resin, reaction time is 4h, and research obtains terebinthine conversion ratio and is about 85%, and the yield of terpinol is about 35%, but terpinol yield is lower, process energy consumption is higher.Wei Yi, Huang Kelin etc. ([6] Chinese patent CN102229524A) utilize a set of fixed-bed catalytic reactor, take resin as the synthesis that catalyst carries out terpinol, but still there is the problems such as product back-mixing is serious, longer, the easy generation side reaction of catalytic reaction time.And the more employing stirred-tank reactor of the research of one-step method is carried out to the synthetic reaction of terpinol both at home and abroad, the method generally needs organic acid as auxiliary agent, and need a large amount of solvents to promote reaction to make raw material fully mix, therefore still there is follow-up separation process complexity, the problem such as equipment corrosion, " three wastes " are seriously polluted, the more important thing is that these class methods easily cause the crack damage of solid catalyst, seriously reduce the life-span of catalyst, therefore cost increases greatly.And although fixed bed reactors solve the life problems of catalyst, but still there is product terpinol in technical process and catalyst contact time long, byproduct compounds and the problem such as content is higher, terpinol yield is lower and energy consumption is higher, its technique is further improved.
Summary of the invention
The object of the invention is to prepare terpinol technical process Problems existing for existing one-step catalytic turpentine oil, a kind of total reflux reaction distilling apparatus and synthetic method thereof of synthesizing terpinol are provided.
The total reflux reaction distilling apparatus of described synthesis terpinol is provided with evaporimeter, evaporating column, condenser coil, catalyst material basket, heating jacket; Described evaporimeter is provided with higher pressure steam inlet, feed(raw material)inlet, hot water outlet, temperature sensor and control interface, pressure sensor and remote alarm interface and discharging opening; Described evaporimeter top is connected with evaporating column, catalyst material basket is located in evaporating column, condenser coil to be located in catalyst material basket and and catalyst exposure, described evaporating column outside is provided with heating jacket and heat-insulation layer, the bottom of evaporating column is provided with hot water inlet, and the top of evaporating column is provided with hot water outlet; Condenser coil two ends are cooling water inlet and coolant outlet.
Described feed(raw material)inlet can be provided with material inlet valve; Described discharging opening can be provided with dispensing valve.
The method of described synthesis terpinol, adopt the total reflux reaction distilling apparatus of synthesis terpinol, step is as follows:
1) condenser coil is put into catalyst material basket, then catalyst and θ ring stainless steel cloth filler mixed packing are entered in catalyst material basket, and catalyst material basket is fixed in evaporating column, closed evaporating tower;
2) close dispensing valve, raw pine fuel-economizing, water and solvent are joined in evaporimeter by material inlet valve, close material inlet valve;
3) heat evaporimeter, raw material and solvent are evaporated and condensation in catalyst material basket, and condensate liquid contact catalyst carries out catalytic reaction; Because evaporating column outer wall has heating jacket and heat-insulation layer, therefore steam only condensation in catalyst material basket; The mixed liquor of evaporation process Raw and solvent forms azeotropic; Product in catalyst material basket and unreacted raw material rely in evaporimeter at the bottom of gravity reflux to tower, and terpinol is deposited in evaporimeter, and raw material and solvent evaporate azeotropic again, and condensation in catalyst material basket, again react; When from evaporimeter during the content <10% of sample analysis firpene, stop the heating of evaporimeter, cessation reaction, open the dispensing valve of base of evaporator, discharges material carries out rectifying separation again, material is separated by rectifying and obtains terpinol product, and the unreacted raw material of rectifying gained and solvent are reused in Returning evaporimeter again.
In step 1), described catalyst can adopt cationic ion-exchange resin, and described cationic ion-exchange resin can select model to be the cationic ion-exchange resin of each model such as Amberlyst15, Amberlyst35, Amberlyst36; Voidage in described catalyst material basket can be 25% ~ 35%; The loadings of described catalyst can be 7% ~ 10% of raw material gross mass by mass percentage;
In step 2) in, described solvent can adopt low-carbon (LC) alcohols, and the mass ratio of described turpentine oil, water, solvent can be 5: (1.5 ~ 2): (3 ~ 3.5).
In step 3), the object that described evaporating column outside is provided with heating jacket and heat-insulation layer is to avoid steam in the condensation of tower wall; Described condenser coil is placed in catalyst material basket, controls condensation in catalyst material basket and reaction temperature by the flow of condensed water and temperature in adjustment condenser coil; Described catalytic reaction is within 6h, and in evaporimeter, the mass concentration of firpene can be less than 10%, and described product is separated through rectifying again, and unreacted raw material and solvent again return total reflux reaction distilling apparatus and reuse; Main containing a small amount of accessory substance such as citrene, terpinolene, amphene in described product, namely can obtain terpinol product by distillation operation.
The technical solution used in the present invention is for raw material with turpentine oil (main component is for firpene) and water, solvent is made with low-carbon (LC) alcohols or ester class (ethyl acetate), catalyst is made with large hole cation exchanger resin, under the proportioning of certain raw material and solvent, utilize the principle of reactive distillation, catalyzing and synthesizing of terpinol is carried out in the total reflux reaction distilling apparatus of designed, designed, obtain higher firpene conversion ratio and terpinol yield, catalyst is in continuous nearly 100 times reaction experiment, and catalytic performance is substantially constant.Product and accessory substance be mainly: alpha-terpineol, β-terpinol, γ-terpinol, 4-terpinol, D-citrene, terpinolene etc.
The as a whole apparatus for reactive distillation of total reflux reaction distilling apparatus of synthesis terpinol of the present invention, evaporimeter top is communicated with evaporating column, and catalyst material basket is placed in evaporating column inside, and condenser coil is placed in catalyst material basket and fully contacts with catalyst.Raw material and solvent evaporate in evaporimeter, because evaporating column outside is provided with heating jacket and heat-insulation layer, therefore steam only contacts cold catalyst material basket in evaporating column is condensed, condensate liquid (comprises water, firpene, solvent) contact and expect that the catalyst in basket reacts, the terpinol that reaction generates and unreacted raw material and solvent flow out material basket fast and depart from catalyst, gravity is relied on all to be back in evaporimeter at the bottom of tower, wherein lower boiling water, firpene and solvent continue evaporation, condensation, the cyclic process of reaction and backflow, the then enrichment in evaporimeter of high boiling product terpinol.When the terpinol analyzed in detection evaporimeter or firpene concentration reach certain index, discharged by evaporimeter by whole material and carry out rectifying separation, the unreacted raw material of rectifying gained and solvent can return this device and reuse.
Outstanding advantages of the present invention:
(1), in the present invention, do not use any organic acid as reaction promoter, the solvent of use be pollution-free, corrosion-free, and to be easily separated with product, recyclable recycling.
(2) in the present invention, whole technical process is carried out in a W-response distillation equipment, automatically completes the full step cycle of the evaporation of raw material, condensation, reaction continuously.Raw material and solvent form azeotropic vaporization in evaporimeter, upflowing vapor only condensation reacting in catalyst material basket.Product terpinol flows out rapidly disengaging catalyst from pit canal material basket, relies on gravity to be all back in evaporimeter at the bottom of tower, thus avoids Long contact time catalyst and side reaction occurs.In addition, the boiling point being back to the terpinol of evaporimeter is far above the azeotropic point of raw material and solvent, therefore terpinol can not evaporate contact catalyst again participates in reaction, thus avoids the generation of side reaction, effectively controls accessory substance and generates.
(3) in the present invention, catalyst material basket is suspended in evaporating column, and evaporimeter is placed in bottom evaporating column, the unreacted feed liquid refluxed downwards from catalyst material basket contacts with solvent vapo(u)r with the high temperature raw material of rising, part is vaporized rising and enters catalyst material basket, and condensation is reacted again, thus shortens the circulating path of reaction raw materials and solvent, reduce the heating load of evaporimeter, make the energy ezpenditure that whole process implementation is lower.Estimation result display energy consumption is lower than conventional two-step method more than 25%, and energy-saving effect is obvious.
Accompanying drawing explanation
Fig. 1 is the structure composition schematic diagram of the total reflux reaction distilling apparatus embodiment of synthesis terpinol.
Fig. 2 is the GC-MS spectrogram of product.
Detailed description of the invention
See Fig. 1, the total reflux reaction distilling apparatus embodiment of synthesis terpinol of the present invention is provided with evaporimeter A, evaporating column B, condenser coil C, catalyst material basket D, heating jacket E; Described evaporimeter A is provided with higher pressure steam inlet A1, feed(raw material)inlet A2, hot water outlet A3, temperature sensor and control interface A4, pressure sensor and remote alarm interface A5 and discharging port A 6; Described evaporimeter A top is connected with evaporating column B, catalyst material basket D is located in evaporating column B, condenser coil C to be located in catalyst material basket D and and catalyst exposure, described evaporating column B outside is provided with heating jacket E and heat-insulation layer (not drawing in FIG), the bottom of evaporating column B is provided with hot water inlet B1, and the top of evaporating column B is provided with hot water outlet B2; Condenser coil C two ends are cooling water inlet C1 and coolant outlet C2.Described feed(raw material)inlet A2 can be provided with material inlet valve V1; Described discharging port A 6 can be provided with dispensing valve V2.
TEMP and control system T comprise: the cooling of the heating of reaction raw materials in evaporimeter A, Temperature displaying and temperature control (with providing steam or direct computer heating control for oneself), condenser coil C, Temperature displaying and temperature control (use normal temperature cooling water control), evaporating column B outer wall chuck heating and temperaturel show (generally only needing Temperature displaying).
The total reflux reaction distil process process of Synthsis of Terpineol Catalyzed of the present invention is: first, condenser coil C is put into catalyst material basket D, again catalyst and θ ring stainless steel cloth filler mixed packing are entered in catalyst material basket D, and catalyst material basket D is fixed in evaporating column B, closed evaporating tower B; Secondly, dispensing valve V is closed
2, turpentine oil, water and solvent are passed through material inlet valve V according to certain proportioning
1add in evaporimeter A, close material inlet valve V
1; Heat evaporimeter A, raw material and solvent are evaporated and condensation in catalyst material basket D, and condensate liquid contact catalyst carries out catalytic reaction.Because evaporating column B outer wall has heating jacket E and heat-insulation layer, therefore steam only condensation in catalyst material basket D.The mixed liquor of evaporation process Raw and solvent forms azeotropic, and its temperature remains unchanged substantially.In catalyst material basket D, the temperature of condensate liquid and condensing liquid quantity are controlled by the flow and temperature regulating cooling water in condenser coil; Along with the carrying out of reaction, product in catalyst material basket D and unreacted raw material rely in evaporimeter A at the bottom of gravity quick backflow to tower, because the boiling point of product terpinol is far above the azeotropic point of raw material and solvent, therefore terpinol is deposited in evaporimeter A, and raw material and solvent evaporate azeotropic again, and condensation in catalyst material basket D, again react.When during the content <10% of sample analysis firpene, stopping the heating of evaporimeter A, cessation reaction from evaporimeter A.Open the dispensing valve V bottom evaporimeter A
2, discharges material goes rectifying to be separated, and material is separated by rectifying and obtains commodity terpinol, and the unreacted raw material of rectifying gained and solvent are reused in Returning evaporimeter A again.
Boiling point due to terpinol is high and do not form azeotropic mixture with other composition, therefore the product terpinol in evaporimeter A gradually enrichment concentrates, and water, solvent and firpene azeotropic vaporization according to a certain percentage, and condensation in catalyst material basket D, reaction repeated is also back in evaporimeter A.Due to the special role of reaction distillation, the product of catalyst surface is easily washed by the raw material condensate liquid of lasting evaporation and hightails catalyst, and does not stop on a catalyst or back-mixing, and side reaction is greatly reduced, and product terpinol yield significantly improves.
Below provide the embodiment utilizing total reflux reaction distilling apparatus to catalyze and synthesize terpinol.
Embodiment 1:
With turpentine oil and water for raw material, take isopropyl alcohol as solvent, the mass ratio of turpentine oil, water and isopropyl alcohol is 5: 2: 3, evaporator temperature is set as 155 DEG C, the temperature adjusting of reactor (catalyst material basket) is at 60 ~ 80 DEG C, the consumption of catalyst is 7.5% of reaction raw materials consumption, and the reaction time is 6h.After reaction, product is through simple rectifying except desolventizing, and through gas chromatographic analysis, the conversion ratio calculating firpene is 97.9%, and the total recovery of terpinol product is 79.8%, and the yield of alpha-terpineol is 49.4%.The GC-MS spectrogram of product is see Fig. 2.
Embodiment 2:
With turpentine oil and water for raw material, take isopropyl alcohol as solvent, the mass ratio of turpentine oil, water and isopropyl alcohol is 5: 2: 3, evaporator temperature is set as 155 DEG C, the temperature adjusting of reactor (catalyst material basket) is at 60 ~ 80 DEG C, and the consumption of catalyst is 10% of reaction raw materials consumption, and the reaction time is 6h.After reaction, product is through simple rectifying except desolventizing, and through gas chromatographic analysis, the conversion ratio calculating firpene is 98.7%, and the total recovery of terpinol product is 68.6%, and the yield of alpha-terpineol is 47.7%.
Embodiment 3:
With turpentine oil and water for raw material, take isopropyl alcohol as solvent, the mass ratio of turpentine oil, water and isopropyl alcohol is 5: 2: 3, evaporator temperature is set as 155 DEG C, the temperature adjusting of reactor (catalyst material basket) is at 45 ~ 65 DEG C, the consumption of catalyst is 7.5% of reaction raw materials consumption, and the reaction time is 6h.After reaction, product is through simple rectifying except desolventizing, and through gas chromatographic analysis, the conversion ratio calculating firpene is 94.0%, and the total recovery of terpinol product is 61.0%, and the yield of alpha-terpineol is 38.9%.
Embodiment 4:
With turpentine oil and water for raw material, take isopropyl alcohol as solvent, the mass ratio of turpentine oil, water and isopropyl alcohol is 5: 2: 3, evaporator temperature is set as 155 DEG C, the temperature adjusting of reactor (catalyst material basket) is at 70 ~ 80 DEG C, the consumption of catalyst is 7.5% of reaction raw materials consumption, and the reaction time is 6h.After reaction, product is through simple rectifying except desolventizing, and through gas chromatographic analysis, the conversion ratio calculating firpene is 98.67%, and the total recovery of terpinol product is 63.6%, and the yield of alpha-terpineol is 38.9%.
Embodiment 5:
With turpentine oil and water for raw material, take isopropyl alcohol as solvent, the mass ratio of turpentine oil, water and isopropyl alcohol is 5: 1.5: 3, evaporator temperature is set as 155 DEG C, the temperature adjusting of reactor (catalyst material basket) is at 70 ~ 80 DEG C, the consumption of catalyst is 7.5% of reaction raw materials consumption, and the reaction time is 6h.After reaction, product is through simple rectifying except desolventizing, and through gas chromatographic analysis, the conversion ratio calculating firpene is 95.9%, and the total recovery of terpinol product is 34.0%, and the yield of alpha-terpineol is 20.9%.
Embodiment 6:
With turpentine oil and water for raw material, take isopropyl alcohol as solvent, the mass ratio of turpentine oil, water and isopropyl alcohol is 5: 2: 3.5, evaporator temperature is set as 155 DEG C, the temperature adjusting of reactor (catalyst material basket) is at 70 ~ 80 DEG C, the consumption of catalyst is 7.5% of reaction raw materials consumption, and the reaction time is 6h.After reaction, product is through simple rectifying except desolventizing, and through gas chromatographic analysis, the conversion ratio calculating firpene is 99.6%, and the total recovery of terpinol product is 78.0%, and the yield of alpha-terpineol is 43.2%.
Claims (6)
1. synthesize a total reflux reaction distilling apparatus for terpinol, it is characterized in that being provided with evaporimeter, evaporating column, condenser coil, catalyst material basket, heating jacket; Described evaporimeter is provided with higher pressure steam inlet, feed(raw material)inlet, hot water outlet, temperature sensor and control interface, pressure sensor and remote alarm interface and discharging opening; Described evaporimeter top is connected with evaporating column, catalyst material basket is located in evaporating column, condenser coil to be located in catalyst material basket and and catalyst exposure, described evaporating column outside is provided with heating jacket and heat-insulation layer, the bottom of evaporating column is provided with hot water inlet, and the top of evaporating column is provided with hot water outlet; Condenser coil two ends are cooling water inlet and coolant outlet;
Described feed(raw material)inlet is provided with material inlet valve;
Described discharging opening is provided with dispensing valve.
2. synthesize a method for terpinol, it is characterized in that adopting the total reflux reaction distilling apparatus synthesizing terpinol as claimed in claim 1, its step is as follows:
1) condenser coil is put into catalyst material basket, then catalyst and θ ring stainless steel cloth filler mixed packing are entered in catalyst material basket, and catalyst material basket is fixed in evaporating column, closed evaporating tower; The loadings of described catalyst is 7% ~ 10% of raw material gross mass by mass percentage;
2) close dispensing valve, raw pine fuel-economizing, water and solvent are joined in evaporimeter by material inlet valve, close material inlet valve; Described solvent adopts low-carbon (LC) alcohols, and the mass ratio of described turpentine oil, water, solvent is 5: (1.5 ~ 2): (3 ~ 3.5);
3) heat evaporimeter, raw material and solvent are evaporated and condensation in catalyst material basket, and condensate liquid contact catalyst carries out catalytic reaction; Because evaporating column outer wall has heating jacket and heat-insulation layer, therefore steam only condensation in catalyst material basket; The mixed liquor of evaporation process Raw and solvent forms azeotropic; Product in catalyst material basket and unreacted raw material rely in evaporimeter at the bottom of gravity reflux to tower, and terpinol is deposited in evaporimeter, and raw material and solvent evaporate azeotropic again, and condensation in catalyst material basket, again react; When from evaporimeter during the content <10% of sample analysis firpene, stop the heating of evaporimeter, cessation reaction, open the dispensing valve of base of evaporator, discharges material carries out rectifying separation again, material is separated by rectifying and obtains terpinol product, and the unreacted raw material of rectifying gained and solvent are reused in Returning evaporimeter again.
3. a kind of method of synthesizing terpinol as claimed in claim 2, is characterized in that in step 1) in, described catalyst adopts cationic ion-exchange resin.
4. a kind of method of synthesizing terpinol as claimed in claim 3, is characterized in that described cationic ion-exchange resin selects model to be Amberlyst15, Amberlyst35, Amberlyst36 cationic ion-exchange resin.
5. a kind of method of synthesizing terpinol as claimed in claim 2, is characterized in that in step 1) in, the voidage in described catalyst material basket is 25% ~ 35%.
6. a kind of method of synthesizing terpinol as claimed in claim 2, is characterized in that in step 3) in, the object that described evaporating column outside is provided with heating jacket and heat-insulation layer is to avoid steam in the condensation of tower wall; Described condenser coil is placed in catalyst material basket, controls condensation in catalyst material basket and reaction temperature by the flow of condensed water and temperature in adjustment condenser coil; Described catalytic reaction is within 6h, and in evaporimeter, the mass concentration of firpene is less than 10%, and described product is separated through rectifying again, and unreacted raw material and solvent again return total reflux reaction distilling apparatus and reuse; Main containing citrene, terpinolene, a small amount of accessory substance of amphene in described product, namely obtain terpinol product by distillation operation.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1197053A (en) * | 1998-05-06 | 1998-10-28 | 中国科学院广州化学研究所 | Method of directly preparing terpene hydrate alcohol by terpene |
| CN101108788A (en) * | 2007-07-13 | 2008-01-23 | 中国林业科学研究院林产化学工业研究所 | Method of manufacturing high purity alpha-terpineol |
| CN101365531A (en) * | 2005-07-28 | 2009-02-11 | 杜邦公司 | Reactors, reactor assemblies, and production processes |
| CN103044202A (en) * | 2013-01-08 | 2013-04-17 | 江苏宏邦化工科技有限公司 | Preparation method of alpha-terpilenol |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH10287600A (en) * | 1997-04-16 | 1998-10-27 | Mitsubishi Chem Corp | Production of cyclohexanol |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1197053A (en) * | 1998-05-06 | 1998-10-28 | 中国科学院广州化学研究所 | Method of directly preparing terpene hydrate alcohol by terpene |
| CN101365531A (en) * | 2005-07-28 | 2009-02-11 | 杜邦公司 | Reactors, reactor assemblies, and production processes |
| CN101108788A (en) * | 2007-07-13 | 2008-01-23 | 中国林业科学研究院林产化学工业研究所 | Method of manufacturing high purity alpha-terpineol |
| CN103044202A (en) * | 2013-01-08 | 2013-04-17 | 江苏宏邦化工科技有限公司 | Preparation method of alpha-terpilenol |
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