CN109384649A - A kind of method of sec-Butyl Acetate catalyzing hydrolysis production sec-butyl alcohol - Google Patents
A kind of method of sec-Butyl Acetate catalyzing hydrolysis production sec-butyl alcohol Download PDFInfo
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- CN109384649A CN109384649A CN201710686006.2A CN201710686006A CN109384649A CN 109384649 A CN109384649 A CN 109384649A CN 201710686006 A CN201710686006 A CN 201710686006A CN 109384649 A CN109384649 A CN 109384649A
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- butyl acetate
- butyl alcohol
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/095—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of organic acids
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Abstract
The present invention provides a kind of method of sec-Butyl Acetate catalyzing hydrolysis production sec-butyl alcohol, the following steps are included: using sec-Butyl Acetate as raw material, a continuous catalysis hydrolysis is fixed, catalyst uses commercially available styrene type cation exchange resin catalyst, it is loaded into the calandria type fixed bed continuous pipe of series connection, the calandria type fixed bed series connection includes multiple duplicate shell and tube reactors, raw material sec-Butyl Acetate and water enter shell and tube reactor, continuous catalysis hydrolysis generates sec-butyl alcohol crude product under the action of catalyst, then high-purity sec-butyl alcohol is made through refining.The high conversion rate of method production sec-butyl alcohol of the invention, and the application range of sec-Butyl Acetate can be improved, the added value of sec-Butyl Acetate is improved, is a kind of invention with market popularization value.
Description
Technical field
The present invention relates to a kind of method for producing sec-butyl alcohol, especially a kind of sec-Butyl Acetate catalyzing hydrolysis produces sec-butyl alcohol
Method.
Technical background
N-butene is a kind of lower petrochemical by-product of chemical industry utilization rate.Before the eighties, due to mixing C4
Isobutene fails to find the approach rationally applied in component, and n-butene exploitation chemical utilization is separated from C4 component needs special point
From unit, cause higher cost and seem inessential, with the construction of MTBE process units, in the C4 component after consuming isobutene
N-butene (1- butylene and 2- butylene) concentration have become very high.Especially in 1- butylene separating technology, by-product 2- butylene it is pure
Degree is up to 95%, if it is possible to develop the higher fine chemical product of added value, bigger effect will be relatively generated as fuel sales
Benefit.Wherein, producing sec-Butyl Acetate as raw material using n-butene becomes one of the utilization ways of n-butene.
At present there are two types of the production methods of sec-Butyl Acetate: alcohol esterification method and n-butene addition process.The former includes sec-butyl alcohol
With acetic acid esterified reaction and sec-butyl alcohol and anhydride reaction, and the latter is under acidic catalyst effect by anhydrous glacial acetic acid and positive fourth
Alkene (2- butylene) addition reaction and directly synthesize.Due to olefin processes production cost lower than alcohol esterification method 1/3 or more, alkene
Addition process is to synthesize the developing direction of sec-Butyl Acetate.
It is that can substitute MTBE work because of the features such as sec-Butyl Acetate has octane number high, nontoxic, non-corrosive, and oxygen content is low
For the new chemical product of gasoline addO-on therapy, certain application is obtained at home, but as country forbids adding vinegar in the oil
The regulation of the secondary butyl ester of acid is implemented, and surplus occurs in domestic sec-Butyl Acetate production capacity, and because of the market shrink, supply exceed demand for sec-Butyl Acetate.
So there is an urgent need to develop downstream product to carry out reducing the inventories.
A kind of process of continuously producing sec-butyl alcohol by direct hydration of n-butene of CN200810016495, in strong acid type ion
In the presence of exchange resin catalyst, fresh n-butene raw material and circulation n-butene are mixed into hydration reactor and be hydrated instead
It answers, is separated subsequently into crude product separative unit, add n-butene refined unit, isolated by crude product separative unit
Unreacted n-butene, a part are back to hydration reactor as circulation n-butene and continue to participate in hydration reaction, and another part is sent
It goes n-butene refined unit to be refined, removes butane, recycle n-butene, continue to use as fresh n-butene raw material.
The method of CN97116406 low-carbon alkene direct hydration continuous production low-carbon alcohols, in strongly acidic cation-exchange
In the presence of catalyst, after the raw material hydrocarbon containing low-carbon alkene is mixed with raw water and recycle hydrocarbons, into main reactor, subsequently into
Crude product separator, it is characterised in that auxiliary reactor and phase separator are additionally provided with after crude product separator, by crude product
Unreacted the hydrocarbon component a part containing low-carbon alkene in main reactor that separator comes out returns main anti-as recycle hydrocarbons
After answering device, another part to mix with deionized water, enter phase into further progress hydration reaction, reaction product in auxiliary reactor
It is separated in separator, separated aqueous solution of alcohol out, the raw water as main reactor enters main reactor, separated hydrocarbon
Phase discharger.
The above patent is the production line that sec-butyl alcohol is produced in the reaction of butylene direct hydration, is had the disadvantages that
(1), conversion per pass is low, less than 10%.
(2), height is required to raw material n-butene concentration, could be used after needing concentrate.
(3), reaction temperature is high, and 140 DEG C or more, energy consumption is high.
Li Fengyun is catalyst using heteropoly acid " synthesizing sec-butyl alcohol using heteropoly acid " in a text, anhydrous glacial acetic acid and
N-butene (2- butylene) addition reaction generates sec-Butyl Acetate, and then sec-Butyl Acetate hydrolysis generates sec-butyl alcohol, hydrolysis master
It to be hydrolyzed in acid condition directly to add water.This method makes butylene produce sec-butyl alcohol by indirect method, has widened acetic acid
The application market of secondary butyl ester.But this method has conversion ratio low using heteropoly acid as catalyst, and by-product is more, and hydrolysis is not thorough
The disadvantages of need to solve.
Summary of the invention
In view of the deficiencies of the prior art, the method for a kind of new production sec-butyl alcohol of the present invention is that a kind of sec-Butyl Acetate is urged
Change the method for hydrolysis production sec-butyl alcohol, comprising the following steps:
Using sec-Butyl Acetate as raw material, a continuous catalysis hydrolysis is fixed, catalyst is using commercially available polystyrene cation
Exchange resin catalyst is loaded into the calandria type fixed bed continuous pipe of series connection, and the series connection is calandria type fixed bed comprising more
A duplicate shell and tube reactor, raw material sec-Butyl Acetate and water enter shell and tube reactor, connect under the action of catalyst
Continuous catalytic hydrolysis reaction generates sec-butyl alcohol crude product, then high-purity sec-butyl alcohol is made through refining.
The styrene type cation exchange resin catalyst is selected from the A35 resin catalyst of U.S.'s ROHM AND HAAS production
Or the D006 resin catalyst of KaiRui Chemical Engineering Co., Ltd's production.
The calandria type fixed bed preferably concatenated 3 duplicate shell and tube reactors of the series connection.
The water ester molar ratio of the raw material sec-Butyl Acetate and water is 2~6.
The continuous catalysis hydrolysis, 80~100 DEG C of preferable reaction temperature, air speed 0.5-8/h, reaction pressure 1~
3MPa。
A kind of method of preferred sec-Butyl Acetate catalyzing hydrolysis production sec-butyl alcohol of the invention, passes through following steps reality
It is existing:
(1), sec-Butyl Acetate catalyzing hydrolysis
For hydrolysis using calandria type fixed bed continuous catalysis device of connecting, which includes 3 duplicate reaction towers, with
Series system connection；
Catalyst uses commercially available styrene type cation exchange resin catalyst, and resin catalyst loads reserved expansion space,
Mixed under sec-Butyl Acetate and water room temperature, with the molar ratio of water to ester ratio 2~6, the air speed of 0.5-8/h pass sequentially through 3 it is concatenated
Reactor, under the action of catalyst occur hydrolysis generate sec-butyl alcohol, 80~100 DEG C of reaction temperature, reaction pressure 1~
3MPa, cooling water in a co-current manner simultaneously exchange heat to 3 reaction towers, take away extra heat of reaction, control reaction temperature；
Sec-Butyl Acetate is directly fixed bed catalyst process with the raw hydrolysis of water catalytic reaction, in tubulation using heatproof sun from
Sub-exchange resin catalyst, raw material sec-Butyl Acetate is directly and water occurs to hydrolyze instead with liquid phase laminar condition by catalyst bed
It answers, reaction generates sec-butyl alcohol under the action of catalyst.
(2), the purification of sec-butyl alcohol
The mixture stratification of sec-butyl alcohol and water that step (1) obtains is separated, the sec-butyl alcohol of high-purity is obtained.
The preparation method of the invention has the advantages that
(1), it overcomes the reaction of butylene direct hydration and produces the low disadvantage of sec-butyl alcohol conversion ratio, conversion ratio is greater than 95%.
(2), the new application for having opened up sec-Butyl Acetate, solves the problems, such as product overloading.
Specific embodiment
Following instance is only to further illustrate the present invention, is not limitation the scope of protection of the invention.
Embodiment 1:
Primary raw material
Sec-Butyl Acetate, Hunan Zhongchuang Chemical Co., Ltd, carbon four and acetic acid addition process produce after ether.Deionized water, from
System.D006 resin catalyst, KaiRui Chemical Engineering Co., Ltd.
(1), sec-Butyl Acetate catalyzing hydrolysis
Test the calandria type fixed bed continuous catalysis experimental rig of series connection used.The system includes 3 duplicate reaction towers,
It connects in a series arrangement, reaction tower diameter Di=240mm, pipe uses 316 stainless steel materials, catheter outer diameter d0=8mm, and pipe has
Imitate length L=3m, pipe radical n=15 piece, rounded projections arranged.
Catalyst uses the D006 resin catalyst of KaiRui Chemical Engineering Co., Ltd's production.Resin catalyst packing factor
Control reserves expansion space 70%.It is mixed after reaction mass preheating, with the molar ratio of setting, air speed passes sequentially through 3 series connection
Reactor, the cooling water used between pipe simultaneously exchanges heat to 3 reaction towers using concurrent, takes away extra heat of reaction
Control reaction temperature.Sec-Butyl Acetate is directly fixed bed catalyst process with the raw hydrolysis of water catalytic reaction, is made in tubulation
With heatproof cation exchange resin catalyst, raw material sec-Butyl Acetate is directly and water with liquid phase laminar condition passes through catalyst bed
Generation hydrolysis, 100 DEG C of reaction temperature, air speed 0.5/h, water ester molar ratio 2, reaction pressure 1MPa, under the action of catalyst
Reaction generates sec-butyl alcohol.
(2), the purification of sec-butyl alcohol
Sec-butyl alcohol and water static layering are separated.
Embodiment product number is KRB-1.
Embodiment 2
Feed space velocity is 8/h, the other the same as in Example 1.Products obtained therefrom number is KRB-2.
Embodiment 3
Feed space velocity is 4/h, the other the same as in Example 1.Products obtained therefrom number is KRB-3.
Embodiment 4
Water to ester ratio is 6 (mol/mol), the other the same as in Example 1.Products obtained therefrom number is KRB-4.
Embodiment 5
Water to ester ratio is 6 (mol/mol), the other the same as in Example 2.Products obtained therefrom number is KRB-5.
Embodiment 6
Water to ester ratio is 6 (mol/mol), the other the same as in Example 3.Products obtained therefrom number is KRB-6.
Embodiment 7
Water to ester ratio is 4 (mol/mol), the other the same as in Example 1.Products obtained therefrom number is KRB-7.
Embodiment 8
Water to ester ratio is 4 (mol/mol), the other the same as in Example 2.Products obtained therefrom number is KRB-8.
Embodiment 9
Water to ester ratio is 4 (mol/mol), the other the same as in Example 3.Products obtained therefrom number is KRB-9.
Embodiment 10
Reaction pressure is 3MPa, the other the same as in Example 1.Products obtained therefrom number is KRB-10.
Embodiment 11
Reaction pressure is 3MPa, the other the same as in Example 2.Products obtained therefrom number is KRB-11.
Embodiment 12
Reaction pressure is 3MPa, the other the same as in Example 3.Products obtained therefrom number is KRB-12.
Embodiment 13
Reaction pressure is 3MPa, the other the same as in Example 4.Products obtained therefrom number is KRB-13.
Embodiment 14
Reaction pressure is 3MPa, the other the same as in Example 5.Products obtained therefrom number is KRB-14.
Embodiment 15
Reaction pressure is 3MPa, other same embodiments 6.Products obtained therefrom number is KRB-15.
Embodiment 16
Reaction pressure is 2MPa, the other the same as in Example 1.Products obtained therefrom number is KRB-16.
Embodiment 17
Reaction pressure is 2MPa, the other the same as in Example 2.Products obtained therefrom number is KRB-17.
Embodiment 18
Reaction pressure is 2MPa, the other the same as in Example 3.Products obtained therefrom number is KRB-18.
Embodiment 19
Conversion zone temperature, 80 DEG C, the other the same as in Example 1.Products obtained therefrom number is KRB-19.
Embodiment 20
Conversion zone temperature, 80 DEG C, the other the same as in Example 2.Products obtained therefrom number is KRB-20.
Embodiment 21
Conversion zone temperature, 80 DEG C, the other the same as in Example 3.Products obtained therefrom number is KRB-21.
Embodiment 22
Conversion zone temperature, 80 DEG C, the other the same as in Example 4.Products obtained therefrom number is KRB-22.
Embodiment 23
Conversion zone temperature, 80 DEG C, the other the same as in Example 5.Products obtained therefrom number is KRB-23.
Embodiment 24
Conversion zone temperature, 80 DEG C, other same embodiments 6.Products obtained therefrom number is KRB-24.
Embodiment 25
Conversion zone temperature, 80 DEG C, other same embodiments 7.Products obtained therefrom number is KRB-25.
Embodiment 26
Conversion zone temperature, 80 DEG C, other same embodiments 8.Products obtained therefrom number is KRB-26.
Embodiment 27
Conversion zone temperature, 80 DEG C, other same embodiments 9.Products obtained therefrom number is KRB-27.
Embodiment 28
Conversion zone temperature, 80 DEG C, the other the same as in Example 10.Products obtained therefrom number is KRB-28.
Embodiment 29
Conversion zone temperature, 80 DEG C, the other the same as in Example 11.Products obtained therefrom number is KRB-29.
Embodiment 30
Conversion zone temperature, 80 DEG C, the other the same as in Example 12.Products obtained therefrom number is KRB-30.
Embodiment 31
Conversion zone temperature, 80 DEG C, the other the same as in Example 13.Products obtained therefrom number is KRB-31.
Embodiment 32
Conversion zone temperature, 80 DEG C, the other the same as in Example 14.Products obtained therefrom number is KRB-32.
Embodiment 33
Conversion zone temperature, 80 DEG C, the other the same as in Example 15.Products obtained therefrom number is KRB-33.
Embodiment 34
Conversion zone temperature, 80 DEG C, the other the same as in Example 16.Products obtained therefrom number is KRB-34.
Embodiment 35
Conversion zone temperature, 80 DEG C, the other the same as in Example 17.Products obtained therefrom number is KRB-35.
Embodiment 36
Conversion zone temperature, 80 DEG C, the other the same as in Example 18.Products obtained therefrom number is KRB-36.
Comparative example 1:
Sec-butyl alcohol is produced using the reaction of butylene direct hydration
Butylene direct hydration reaction evaluation experiment 10L reactor is divided into four sections, the resistance to D008 high-temperature strong acid cation of every section of filling
Exchange resin catalyst 1L, n-butene raw material pass through four sections of beds from below to up, and process water is from the bed lower part of every section of catalyst
Divide four sections of entrance, reaction generates sec-butyl alcohol under the effect of the catalyst.It reacts the SBA generated to flow out from reactor head, reaction
Process water afterwards is flowed out from each bed top overflow weir bottom, after water process, is recycled.150 DEG C of reaction temperature, butylene
Air speed 1.7/h, reaction pressure 6.0MPa, water alkene molar ratio 1.1, butene conversion comparison are shown in Table 1.
The ratio of table 1. different formulations sample butylene conversion per pass and conductivity
| Number | Butene conversion % |
| KRB-1 | 99.2 |
| KRB-2 | 99.8 |
| KRB-3 | 99.6 |
| KRB-4 | 97.5 |
| KRB-5 | 99.3 |
| KRB-6 | 98.9 |
| KRB-7 | 99.2 |
| KRB-8 | 98.2 |
| KRB-9 | 98.2 |
| KRB-10 | 99.6 |
| KRB-11 | 99.9 |
| KRB-12 | 99.6 |
| KRB-13 | 98.6 |
| KRB-14 | 99.8 |
| KRB-15 | 99.8 |
| KRB-16 | 96.9 |
| KRB-17 | 99.5 |
| KRB-18 | 99.7 |
| KRB-19 | 93.2 |
| KRB-20 | 91.7 |
| KRB-21 | 90.3 |
| KRB-22 | 90.6 |
| KRB-23 | 91.1 |
| KRB-24 | 90.8 |
| KRB-25 | 92.9 |
| KRB-26 | 91.5 |
| KRB-27 | 93.2 |
| KRB-28 | 91.5 |
| KRB-29 | 92.1 |
| KRB-30 | 91.6 |
| KRB-31 | 91.8 |
| KRB-32 | 90.5 |
| KRB-33 | 90.6 |
| KRB-34 | 92.9 |
| KRB-35 | 90.8 |
| KRB-36 | 90.2 |
| Comparative example 1 | 6.5 |
As seen from the above table, a kind of sec-Butyl Acetate of the present invention is connected the method for calandria type fixed bed catalyzing hydrolysis production sec-butyl alcohol,
The application range that sec-Butyl Acetate can be improved improves the added value of sec-Butyl Acetate, is a kind of hair with market popularization value
It is bright.
Claims (6)
1. a kind of method of sec-Butyl Acetate catalyzing hydrolysis production sec-butyl alcohol, comprising the following steps:
Using sec-Butyl Acetate as raw material, a continuous catalysis hydrolysis is fixed, catalyst is using commercially available polystyrene cation
Exchange resin catalyst is loaded into the calandria type fixed bed continuous pipe of series connection, and the series connection is calandria type fixed bed comprising more
A duplicate shell and tube reactor, raw material sec-Butyl Acetate and water enter shell and tube reactor, connect under the action of catalyst
Continuous catalytic hydrolysis reaction generates sec-butyl alcohol crude product, then high-purity sec-butyl alcohol is made through refining.
2. method described in claim 1, it is characterised in that: the styrene type cation exchange resin catalyst is selected from beauty
The A35 resin catalyst of state's ROHM AND HAAS production or the D006 resin catalyst of KaiRui Chemical Engineering Co., Ltd's production.
3. method described in claim 1, it is characterised in that: the calandria type fixed bed series connection is concatenated 3 complete one
The shell and tube reactor of sample.
4. method described in claim 1, it is characterised in that: the water ester molar ratio of the raw material sec-Butyl Acetate and water is 2
~6.
5. method described in claim 1, it is characterised in that: the continuous catalysis hydrolysis, reaction temperature 80~100
DEG C, air speed 0.5-8/h, 1~3MPa of reaction pressure.
6. method described in claim 1, which is characterized in that realized by following steps:
(1) sec-Butyl Acetate catalyzing hydrolysis
For hydrolysis using calandria type fixed bed continuous catalysis device of connecting, which includes 3 duplicate reaction towers, with
Series system connection；
Catalyst uses commercially available styrene type cation exchange resin catalyst, and resin catalyst loads reserved expansion space,
Mixed under sec-Butyl Acetate and water room temperature, with the molar ratio of water to ester ratio 2~6, the air speed of 0.5-8/h pass sequentially through 3 it is concatenated
Reactor, under the action of catalyst occur hydrolysis generate sec-butyl alcohol, 80~100 DEG C of reaction temperature, reaction pressure 1~
3MPa, cooling water in a co-current manner simultaneously exchange heat to 3 reaction towers, take away extra heat of reaction, control reaction temperature；
(2) purification of sec-butyl alcohol
The quiet stratification of mixture of sec-butyl alcohol and water that step (1) obtains is separated, the sec-butyl alcohol of high-purity is obtained.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115724715A (en) * | 2022-12-07 | 2023-03-03 | 湖南中创化工股份有限公司 | Sec-butyl alcohol refining method and device |
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- 2017-08-11 CN CN201710686006.2A patent/CN109384649A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115724715A (en) * | 2022-12-07 | 2023-03-03 | 湖南中创化工股份有限公司 | Sec-butyl alcohol refining method and device |
| CN115724715B (en) * | 2022-12-07 | 2024-03-08 | 湖南中创化工股份有限公司 | Refining method and device of sec-butyl alcohol |
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