CN105837435B - A kind of method that continuous esterification prepares compounding acetic isoborneol ester - Google Patents
A kind of method that continuous esterification prepares compounding acetic isoborneol ester Download PDFInfo
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- CN105837435B CN105837435B CN201610254757.2A CN201610254757A CN105837435B CN 105837435 B CN105837435 B CN 105837435B CN 201610254757 A CN201610254757 A CN 201610254757A CN 105837435 B CN105837435 B CN 105837435B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
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Abstract
The present invention relates to a kind of methods that continuous esterification prepares compounding acetic isoborneol ester.Using amphene and acetic acid as raw material, compounding acetic isoborneol ester is prepared by shell and tube Oscillatory Flow Reactor continuous esterification.The continuous production of compounding acetic isoborneol ester can be realized by using the method and its device of the present invention, heterogeneous solid particle is selected to be catalyst and be at fluidisation state, the heat transfer that can improve in traditional batch technique is bad, temperature is uneven, the problems such as side reaction is more, reach good heat transfer, prevents reaction heat accumulation to improve service life and the reaction selectivity of catalyst, and convenient for being detached with product；The reactor that this method uses uses the turbulance that special construction is flowed with strength imparting material, the mass-and heat-transfer during intensified response, and catalyst surface is made to timely update, to improve reaction rate and feed stock conversion.This method and its device are not only suitable for the industrialized production of fine chemistry industry compounding acetic isoborneol ester, are equally applicable to other same similar solid-liquid two-phase exothermal reaction process.
Description
Technical field
The invention belongs to field of fine chemical, are more particularly to a kind of method that continuous esterification prepares compounding acetic isoborneol ester.
Background technology
Compounding acetic isoborneol ester is mainly used for cosmetics, disinfectant due to can be used as fragrance with faint scent and Song Shan leaf smells
With air freshener etc.；In addition, compounding acetic isoborneol ester is also the important intermediate of artificial camphor, due to the scarcity of natural camphor,
So that the synthesis of the compounding acetic isoborneol ester as intermediate is also increasingly taken seriously.
Generally using amphene and acetic acid as raw material, esterification under the action of catalyst obtains industrial compounding acetic isoborneol ester.It is theoretical
On can be used for the esterification process catalyst type it is various, it is contemplated that catalyst life, to the environmental pollution of equipment burn into and rear place
The factors such as reason mainly use sulfonate ion-exchange membrane and acid cation exchange resin in domestic industry metaplasia production at present.But
The esterification process mostly uses greatly batch still operation at present, and it is longer that there are production process routes, and labor intensity is big, catalyst rapid wear
The deficiencies of bad, product composition is unstable, and once through yield is low and post-processing is difficult.Therefore, for the industrialization of compounding acetic isoborneol ester
Production process need to be advanced optimized and perfect.
The continuous production technology research that compounding acetic isoborneol ester is produced about camphene esterification is few.Patent CN1036950A exists
Just proposing within 1989 uses natural mordenite zeolite for catalyst, with fixed bed adverse current continuous esterification synthesis of acetic acid Isobornyl
Method, though this method realizes continuous operation, it is unstable that there are catalyst performances, and by-product is difficult to detach, product yield
It is low with purity, invest the deficiencies of big with energy consumption.Patent CN101372453A in 2008 discloses a kind of by controlling catalyst
Water content improves the fixed bed continuous esterification process of compounding acetic isoborneol ester yield, and patent CN101921191A in 2010 proposes
It is same to use fixed bed, and using synthesis of molecular sieve as catalyst, fixed bed reactors and catalyst that the two processes use
There are preferable conversion ratio and selectivity.But since the reaction is a stronger exothermic reaction, system poor heat radiation is easily caused,
Bed temperature is uneven and by-product is caused to increase；And solid catalyst is used, surface easily forms the product of high concentration and hinders
The forward direction of the reversible reaction is mobile, and only timely updating for catalyst surface could improve such case.But two above is special
There is no solve two above critical issue for the fixed bed reactors that profit uses.
The Oscillatory Flow Reactor that the present invention uses has good mass-and heat-transfer performance, and has under certain oscillating condition
Good mixed effect can also have the residence time destribution of approximate laminar flow at low flow rates, therefore for much chemically reacting
For, there is advantageous advantage.The most classical four classes chemical reaction of Oscillatory Flow Reactor application at present include suspension polymerisation,
Fermentation prepares biodiesel（CN103254997A）, catalysis reaction（US20140066667 A1）, and in solid-liquid two phase reaction body
The research of system is rarely reported.The esterification that the present invention studies is that a fuel factor is apparent and there are the system of solid catalyst,
It is badly in need of a kind of reactor with good heat transfer mass transfer effect to solve the problems, such as that current industry exists, Oscillatory Flow Reactor is exactly
One selection well.
Invention content
The purpose of the present invention is to provide a kind of methods that continuous esterification prepares compounding acetic isoborneol ester, and which overcome existing works
By-product existing for skill is more, and reaction rate is slow, and catalyst is easily inactivated because of moisture and polymer, heat transfer and mass transfer is bad etc. asks
Topic, this method can realize the good catalytic effect of catalyst and long lifespan；Reactor is due to using special construction and with outstanding
Heat transfer and mass transfer ability, interior temperature distribution uniform, controllable, catalyst surface realization timely update, and reaction rate is accelerated, choosing
The advantages that selecting property is high.
To achieve the above object, technical scheme is as follows：
A kind of continuous esterification prepares the method for compounding acetic isoborneol ester and its device includes the process of continuous esterification and realize should
Equipment two parts of process, are as follows：
The process of the continuous esterification is to be successively inputted to be mounted with admittedly according to a certain percentage by material camphene and acetic acid
It is reacted in the Oscillatory Flow Reactor of body catalyst, controls certain process conditions to get target product compounding acetic isoborneol ester.
The process apparatus refers to comprising Oscillatory Flow Reactor, clapp oscillator, raw material mixing channel, purification of products tower etc.
A series of equipment of the realization continuous esterification process of equipment composition, wherein Oscillatory Flow Reactor（See attached drawing 2）It is to realize to be esterified
Journey main reactor passes through clapp oscillator in reaction process（CN201520229309.8）To the material in reactor with one
The oscillation for determining intensity makes the catalyst in reactor that uniform fluidized suspension state be presented.
Specially：
（1）Using industrial amphene and industrial acetic as raw material, raw material mixing channel V-101 is separately input by certain mol proportion
In, it stirs evenly, and utilize steam or hot water by raw material preheating to 30 ~ 50 DEG C；
（2）Raw material after preheating is delivered to the shell and tube Oscillatory Flow Reactor for being mounted with solid catalyst with pump P-101A/B
In R-101；Oscillation generator P-102 is opened, esterification is carried out；The heat of Oscillatory Flow Reactor is by heat transferring medium in tube side
It is shifted；
（3）Esterification reaction product is stored to reaction product storage tank V-102, then is delivered to product by pump P-103 A/B and is carried
Pure tower T-101, after overhead product is purified, then by pump P-104 A/B be delivered to product storage tank V-103.
Step（1）The molar ratio of middle industry amphene and industrial acetic is 1:1.1~2.0.
Step（2）Described in solid catalyst be selected from zeolite molecular sieve, solid super-strong acid, heteropoly acid and cation exchange
One kind in resin；Solid catalyst loadings are the 10 ~ 30% of reactor volume.
Step（2）The condition of middle esterification is：20 ~ 100 DEG C of reaction temperature, industrial acetic, the air speed of industrial amphene are
0.1~6.0h-1, reaction pressure is 0.1 MPa ~ 1.0MPa.
Step（2）The amplitude of shell and tube Oscillatory Flow Reactor is 1 ~ 20mm, and frequency is 1 ~ 5Hz, vibrates Reynolds numberRe oFor
800-2500, net Reynolds numberRe nFor 800-1000, speed ratioψFor 1-2, make catalyst that uniform fluidisation state be presented.
Step（2）The quantity of the shell and tube Oscillatory Flow Reactor is one or more in parallel.
Step（2）The inner member of the shell and tube Oscillatory Flow Reactor is in baffle, periodic expansion section, screw rod
It is a kind of.
Device used by this method（Attached drawing 1）The characteristics of be：
Material camphene and acetic acid are squeezed into after raw material mixing channel to the row that one or more parallel connections are transported to by fluid delivery pump
Tubular type Oscillatory Flow Reactor（Attached drawing 2）, reactor is interior to be equipped with certain solid catalyst；The amplitude of the reactor is occurred by oscillation
Device（CN201520229309.8）Control, frequency of oscillation make the material in reactor exist by frequency converter adjusting control, the two cooperation
Reciprocating vibration under certain amplitude and frequency ensures that catalyst is in uniform fluidisation state；The heat of reactor is exchanged heat by shell side
Medium is shifted, and is ensured reaction temperature uniformly and is unlikely to excessively high；The esterification products of reactor outlet enter last product
Purifying column is purified.
Previous oscillation fluid bed is chiefly used in reducing the critical fludization velocity of solid particle, applies the drying in solid particle,
And have the characteristics that amplitude is small, frequency is high, and how not parallel orientation of oscillation and gravity direction be.And herein described oscillatory flow makeup
Amplitude is set far above dry use, frequency far below oscillation fluid bed, can be used for improving heat transfer, solid-liquid mass transfer and enhance mixing；Tool
Body is shown as：
Firstly, since oscillation and suspended state is presented in material and catalyst in reactor, and entire catalyst bed exists
It is evenly distributed on radial and axial, fixed bed and suspension bed is better than on heat-transfer effect, can not only make the temperature of reaction system
It is evenly distributed, while the heat that the exothermic reaction generates can be transferred out in time in time, it is not easy to generate heat accumulation, effectively
The generation of by-product amphene polymer and different camphane ester is prevented, reactant stops close to laminar flow on entire bed is axial in addition
Stay the time uniform, to reaction selectivity higher, feed stock conversion is high, and by-product is few, and product quality is stablized；
Secondly, there are a considerable amount of inner members in Oscillatory Flow Reactor, when the external world applies some strength oscillation, in phase
Position between adjacent inner member can form eddy-currents, i.e., be equivalent to full mixing reactor, therefore mass transfer between material radially
Well.For catalyst and reactant, since mixability is more preferable, the contact probability of reactant and catalytic active center is more
Greatly, then reaction rate is faster；For catalyst itself, since reaction may generate amphene polymer and be attached to catalyst
Activated centre, when system, which exists, to be vibrated, then catalyst surface is constantly washed away by material, it is not easy to be adhered to by polymer, and table
Face can timely update, you can so that the product generated in catalyst surface is spread in time, do not interfere with esterification it is positive into
Row.Therefore, the good mass-transfer of Oscillatory Flow Reactor, can make catalyst effect more preferable and the service life extends, and reaction rate is accelerated, one way
Conversion ratio is got higher；
Again, the oscillation intensity of reactor can be adjusted by adjusting amplitude and frequency, according to different reactants
The oscillation Reynolds number, net Reynolds number and speed ratio of respective range can be obtained in air speed or the fuel factor of different exothermic reactions so that urges
Agent is in preferable even fluidizing state, and reaction unit applicability and operating flexibility are larger, i.e., the device is not only available for second
The synthesis of sour Isobornyl can be used for the larger reaction of other fuel factors.
Compared with the prior art, the advantages of the present invention are as follows：
1）The shell and tube Oscillatory Flow Reactor that the present invention uses, since it can significantly improve the mixability of material, mass transfer
Heat transfer property is excellent, and technical process is easy to control, and has excellent residence time destribution characteristic under continuous operation state,
Huge industrial application value has been shown in chemical process industry.Industrial production compounding acetic isoborneol ester exists most at present
Big problem is that heat transfer, mass transfer and catalyst inactivation, then just solves above three using shell and tube Oscillatory Flow Reactor
Big problem；
2）Oscillatory Flow Reactor is applied in camphene esterification reaction by the present invention, is for the first time by the reactor applied to larger
In the solid-liquid two-phase system reaction of solid particle, continuous production is not only realized, but also solves heat dissipation unevenness and different camphane ester（It is secondary
Product）Too high levels problem, the selectivity of amphene and the service life of catalyst are much better than common fixed bed reactors or suspension bed；
In addition the device is applied equally to other solid-liquid two phase reactions, by keeping the solids at oscillation and suspended state, you can
Significantly improve the validity that solid material participates in reaction.
Description of the drawings
Fig. 1 is the process flow diagram that serialization of the present invention prepares compounding acetic isoborneol ester method；
Wherein：V-101 is raw material mixing channel；R-101 is shell and tube Oscillatory Flow Reactor；V-102 stores up for reaction product
Slot；T-101 is purification of products tower；V-103 is product storage tank；P-101A/B, P-103 A/B, P-104 A/B are material conveying
Pump；P-102 is oscillation generator；
Fig. 2 is shell and tube Oscillatory Flow Reactor of the present invention, wherein：A is oscillation mouth；B, e are drain；C, d according to
The secondary export and import for material；F is row's mouth；G, h are followed successively by the export and import of recirculated water.
Specific implementation mode
In order to describe the technical content, the structural feature, the achieved object and the effect of this invention in detail, and combination is embodied
Mode simultaneously coordinates attached drawing to be described in detail, but protection scope of the present invention is not limited to following specific examples, and the present apparatus is answered
The solid-liquid two-phase exothermic reaction system similar for other also belongs to this patent range.
A kind of method that continuous esterification prepares compounding acetic isoborneol ester includes the process of continuous esterification and realizes setting for the process
Standby two parts, are as follows：
The process of the continuous esterification is to continuously enter material camphene and acetic acid according to a certain percentage to be mounted with admittedly
It is reacted in the Oscillatory Flow Reactor of body catalyst, controls certain process conditions to get target product compounding acetic isoborneol ester.
The process apparatus refers to comprising Oscillatory Flow Reactor, clapp oscillator, raw material mixing channel, purification of products tower etc.
A series of equipment of the realization continuous esterification process of equipment composition, wherein Oscillatory Flow Reactor（See attached drawing 2）It is to realize to be esterified
Journey main reactor passes through clapp oscillator in reaction process（CN201520229309.8）To the material in reactor with one
The oscillation for determining intensity makes the catalyst in reactor that uniform fluidized suspension state be presented.
The molar ratio of the industrial amphene and industrial acetic is 1:1.1~2.0.
The solid catalyst is in zeolite molecular sieve, solid super-strong acid, heteropoly acid and cation exchange resin
It is a kind of；Solid catalyst loadings are the 10 ~ 30% of reactor volume.
The condition of the esterification is：20 ~ 100 DEG C of reaction temperature, industrial acetic, the air speed of industrial amphene be 0.1 ~
6.0h-1, reaction pressure is 0.1 MPa ~ 1.0MPa.
The amplitude of the shell and tube Oscillatory Flow Reactor is 1 ~ 20mm, and frequency is 1 ~ 5Hz, vibrates Reynolds numberRe oFor
800-2500, net Reynolds numberRe nFor 800-1000, speed ratioψFor 1-2, make catalyst that uniform fluidisation state be presented.
The quantity of the shell and tube Oscillatory Flow Reactor is one or more in parallel.
The inner member of the shell and tube Oscillatory Flow Reactor is one kind in baffle, periodic expansion section, screw rod.
Embodiment 1
Using industrial amphene and industrial acetic as raw material, by 1:1.1 molar ratio is squeezed into raw material mixing channel V-101 respectively
After stir evenly, and using hot water by raw material preheating to 40 DEG C；Raw material after preheating gets to list with pump with the flow velocity of 3.18ml/s
In one tubulation Oscillatory Flow Reactor.The reactor uses the inner member of annulus baffle-type, inside to be equipped with 10%（Reactor volume）
NKC-9 cation exchange resins, resin in advance use reaction raw materials impregnate, reaction temperature is controlled using constant temperature water bath
At 40 ± 1 DEG C, reaction pressure is normal pressure.Oscillation generator is opened, original frequency is set as 20HZ, waits for that catalyst distribution is completely reacted
Frequency is adjusted to 3 Hz, amplitude 7mm after device, catalyst can be uniformly distributed in reactor at this time；Esterification is carried out, and
After purified, product is obtained.
The yield of amphene selectivity 98.7% with this condition, compounding acetic isoborneol ester is 83.9%, in product obtained by side reaction
The content of different camphane ester is 0.13%（Mass fraction, similarly hereinafter）, the catalyst continuous use service life was at 60 days or more；Under equal conditions,
It has a rest the amphene selectivity 92.5% of still reaction, the yield of compounding acetic isoborneol ester is 65.3%, different camphane ester obtained by side reaction in product
Content be 0.66%, catalyst be used continuously the service life at 30 days or so.
Embodiment 2
Using industrial amphene and industrial acetic as raw material, by 1:1.1 molar ratio is squeezed into raw material mixing channel V-101 respectively
After stir evenly, and using hot water by raw material preheating to 50 DEG C；Raw material after preheating gets to list with pump with the flow velocity of 3.18ml/s
In one tubulation Oscillatory Flow Reactor.The reactor uses the inner member of annulus baffle-type, inside to be equipped with 10%（Reactor volume）
NKC-9 cation exchange resins, resin in advance use reaction raw materials impregnate, reaction temperature is controlled using constant temperature water bath
At 50 ± 1 DEG C, reaction pressure is normal pressure.Oscillation generator is opened, original frequency is set as 20HZ, waits for that catalyst distribution is completely reacted
Frequency is adjusted to 3 HZ, amplitude 7mm after device, catalyst can be uniformly distributed in reactor at this time；Esterification is carried out, and
After purified, product is obtained.
The yield of amphene selectivity 96.9% with this condition, compounding acetic isoborneol ester is 80.4%, in product obtained by side reaction
The content of different camphane ester is 0.54%, and the service life was used continuously at 60 days or more in catalyst；Under equal conditions, the camphane of batch tank reaction
The yield of alkene selectivity 89.2%, compounding acetic isoborneol ester is 63.5%, and the content of different camphane ester obtained by side reaction is 1.90% in product,
The service life was used continuously at 30 days or so in catalyst.
Embodiment 3
Using industrial amphene and industrial acetic as raw material, by 1:After 2 molar ratio is squeezed into raw material mixing channel V-101 respectively
It stirs evenly, and utilizes hot water by raw material preheating to 40 DEG C；Raw material after preheating is got to pump with the flow velocity of 3.18ml/s single
Tubulation Oscillatory Flow Reactor in.The reactor uses the inner member of annulus baffle-type, inside to be equipped with 10%（Reactor volume）'s
NKC-9 cation exchange resins, resin use reaction raw materials to impregnate in advance, are controlled reaction temperature using constant temperature water bath
40 ± 1 DEG C, reaction pressure is normal pressure.Oscillation generator is opened, original frequency is set as 20Hz, waits for that catalyst distribution expires reactor
Frequency is adjusted to 3 Hz, amplitude 7mm afterwards, catalyst can be uniformly distributed in reactor at this time；Esterification is carried out, and is passed through
After purification, product is obtained.
The yield of amphene selectivity 99.1% with this condition, compounding acetic isoborneol ester is 88.4%, in product obtained by side reaction
The content of different camphane ester is 0.09%, and the service life was used continuously at 45 days or more in catalyst；Under the same terms, the camphane of batch tank reaction
The yield of alkene selectivity 93.8%, compounding acetic isoborneol ester is 69.5%, and the content of different camphane ester obtained by side reaction is 0.35% in product,
The service life was used continuously at 25 days or so in catalyst.
Interval mistake is much better than by the result obtained by method and apparatus using the present invention it can be seen from the above case result
Journey.
The foregoing is merely presently preferred embodiments of the present invention, all equivalent changes done according to scope of the present invention patent with
Modification should all belong to the covering scope of the present invention.
Claims (4)
1. a kind of method that continuous esterification prepares compounding acetic isoborneol ester, it is characterised in that：Include the following steps：
（1）Using industrial amphene and industrial acetic as raw material, it is separately input into raw material mixing channel V-101, stirs by certain mol proportion
It mixes uniformly, and utilizes steam or hot water by raw material preheating to 30 ~ 50 DEG C；
（2）Raw material after preheating is delivered to the shell and tube Oscillatory Flow Reactor R- for being mounted with solid catalyst with pump P-101A/B
In 101；Oscillation generator P-102 is opened, esterification is carried out；The heat of Oscillatory Flow Reactor by heat transferring medium in tube side into
Row transfer；The amplitude of the shell and tube Oscillatory Flow Reactor is 1 ~ 20mm, and frequency is 1 ~ 5Hz, vibrates Reynolds numberRe oFor 800 ~
2500, net Reynolds numberRe nIt is 800 ~ 1000, speed ratioψIt is 1 ~ 2；It is super that the solid catalyst is selected from zeolite molecular sieve, solid
One kind in strong acid, heteropoly acid and cation exchange resin；Solid catalyst loadings are the 10 ~ 30% of reactor volume；It is described
The condition of esterification be：20 ~ 100 DEG C of reaction temperature, industrial acetic, the air speed of industrial amphene are 0.1 ~ 6.0h-1, reaction pressure
Power is 0.1 MPa ~ 1.0MPa；
（3）Esterification reaction product is stored to reaction product storage tank V-102, then is delivered to purification of products tower by pumping P-103 A/B
T-101, after overhead product is purified, then by pump P-104 A/B be delivered to product storage tank V-103.
2. the method that continuous esterification according to claim 1 prepares compounding acetic isoborneol ester, it is characterised in that：Step（1）In
The molar ratio of industrial amphene and industrial acetic is 1:1.1~2.0.
3. the method that continuous esterification according to claim 1 prepares compounding acetic isoborneol ester, it is characterised in that：Step（2）Institute
The quantity for the shell and tube Oscillatory Flow Reactor stated is one or more in parallel.
4. the method that continuous esterification according to claim 1 prepares compounding acetic isoborneol ester, it is characterised in that：Step（2）Institute
The inner member for the shell and tube Oscillatory Flow Reactor stated is one kind in baffle, periodic expansion section, screw rod.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102276453A (en) * | 2011-06-30 | 2011-12-14 | 福州大学 | Method for preparing isobomyl acetate through camphene esterification |
| CN104478666A (en) * | 2014-08-25 | 2015-04-01 | 福州大学 | Method for preparing isoborneol through continuous saponification of isobornyl acetate |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102276453A (en) * | 2011-06-30 | 2011-12-14 | 福州大学 | Method for preparing isobomyl acetate through camphene esterification |
| CN104478666A (en) * | 2014-08-25 | 2015-04-01 | 福州大学 | Method for preparing isoborneol through continuous saponification of isobornyl acetate |
Non-Patent Citations (1)
| Title |
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| 莰烯酯化连续化工艺的研究;赵海泉等;《安徽化工》;20110228;第37卷(第1期);43-45，50 * |
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