CN105418397B - A kind of separation method of acetophenone and 1 benzyl carbinol - Google Patents
A kind of separation method of acetophenone and 1 benzyl carbinol Download PDFInfo
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- CN105418397B CN105418397B CN201510713615.3A CN201510713615A CN105418397B CN 105418397 B CN105418397 B CN 105418397B CN 201510713615 A CN201510713615 A CN 201510713615A CN 105418397 B CN105418397 B CN 105418397B
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- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 title claims abstract description 368
- 238000000926 separation method Methods 0.000 title claims abstract description 34
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 title abstract description 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 256
- 238000000605 extraction Methods 0.000 claims abstract description 134
- 235000011187 glycerol Nutrition 0.000 claims abstract description 123
- 230000008878 coupling Effects 0.000 claims abstract description 3
- 238000010168 coupling process Methods 0.000 claims abstract description 3
- 238000005859 coupling reaction Methods 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 128
- 238000004821 distillation Methods 0.000 claims description 59
- 238000009835 boiling Methods 0.000 claims description 43
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000000034 method Methods 0.000 abstract description 17
- 230000000694 effects Effects 0.000 abstract description 4
- 239000000047 product Substances 0.000 description 48
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- 238000011084 recovery Methods 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 238000004458 analytical method Methods 0.000 description 21
- 238000005070 sampling Methods 0.000 description 20
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000002156 mixing Methods 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 2
- 235000019504 cigarettes Nutrition 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 235000013599 spices Nutrition 0.000 description 2
- 235000009917 Crataegus X brevipes Nutrition 0.000 description 1
- 235000013204 Crataegus X haemacarpa Nutrition 0.000 description 1
- 235000009685 Crataegus X maligna Nutrition 0.000 description 1
- 235000009444 Crataegus X rubrocarnea Nutrition 0.000 description 1
- 235000009486 Crataegus bullatus Nutrition 0.000 description 1
- 235000017181 Crataegus chrysocarpa Nutrition 0.000 description 1
- 235000009682 Crataegus limnophila Nutrition 0.000 description 1
- 235000004423 Crataegus monogyna Nutrition 0.000 description 1
- 240000000171 Crataegus monogyna Species 0.000 description 1
- 235000002313 Crataegus paludosa Nutrition 0.000 description 1
- 235000009840 Crataegus x incaedua Nutrition 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000686 essence Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- 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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- 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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
-
- C—CHEMISTRY; METALLURGY
- 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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
- C07C29/84—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation by extractive distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
- C07C45/83—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation by extractive distillation
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
It is different with relative volatility according to the solubility of acetophenone and 1 benzyl carbinol in glycerine the invention discloses a kind of acetophenone and the separation method of 1 benzyl carbinol, both separation are realized using the coupling operation of extraction and rectifying.The present invention has the advantages that simple technique, good separating effect, energy-conserving and environment-protective, suitable industrial scale continuous operation.
Description
Technical field
The invention belongs to field of fine chemical, and in particular to a kind of separation method of acetophenone and 1- benzyl carbinol.
Background technology
Acetophenone is a kind of important Organic Chemicals, there is the smell of hawthorn, can be used as solvent, spices, plasticizer and
Chemical intermediate and be widely used in perfumed soap, cigarette, spices, medicine, resin etc., 19.6 DEG C of fusing point, 202 DEG C of boiling point is close
Degree 1.027.1- benzyl carbinols are also a kind of important Organic Chemicals, have soft, happy and lasting rose fragrance, are fragrant
More important and widely used a kind of flavorant in material aromatic compound, it is fragrant to be widely used in various flavoring essences and cigarette
In essence, 20 DEG C of fusing point, 203.6 DEG C of boiling point, density 1.013.
The method of industrial production acetophenone has cumene oxidation by-product method and ethylbenzene oxidation method.To cumene oxidation by-product
Method, substantial amounts of acetophenone and 1- benzyl carbinols are contained in its accessory substance.To ethylbenzene oxidation method, its oxidation product be mainly acetophenone and
1- benzyl carbinols.Therefore, the separation of acetophenone and 1- benzyl carbinols is that industrially acetophenone or 1- benzyl carbinol processed inevitably operates.
Because acetophenone and 1- benzyl carbinols have a closely similar physical property, the fusing point of the two differs 0.4 DEG C, boiling point difference under normal pressure
1.6 DEG C, density difference 0.014, it is difficult separation using the methods of common rectifying, crystallization, sedimentation.At present to acetophenone and 1- benzene
The separation of ethanol typically solves by distillation process, due to very similar boiling point, generally require substantial amounts the number of plates or
The separation of the two could be realized using special extract rectification method.CN102627544A propose it is a kind of using cyclodextrin to acetophenone and
The different inclusion ability of 1- benzyl carbinols and the method that both are realized to separation, although the method has, separation condition is gentle, separation effect
The advantages that fruit is good, and separating medium is reusable, but operation cycle length, (generally more than 12 hours), isolated product is pure
Degree is in most cases relatively low, and complex operation, is not suitable for industrial scale production.
The content of the invention
It is an object of the invention to overcome the deficiencies of the prior art and provide a kind of technique is simple, good separating effect, energy-saving ring
Protect, be adapted to the acetophenone of industrial scale continuous operation and the separation method of 1- benzyl carbinols.
The present invention solve the technical scheme that uses of above-mentioned technical problem for：A kind of separation side of acetophenone and 1- benzyl carbinol
Method, it is different with relative volatility according to solubility of the acetophenone with 1- benzyl carbinols in glycerine, utilize the coupling of extraction and rectifying
Closing operation realizes both separation, specifically using one of following three kinds of schemes：
Scheme one comprises the following steps：
(1) acetophenone of the mass percentage concentration of acetophenone not less than 40% is squeezed into extraction with 1- benzyl carbinol mixtures
Tower, counter current contacting is extracted in extraction tower with glycerine, and tower top obtains product acetophenone, and bottom of towe obtains acetophenone, 1- benzene
The mixture of ethanol and glycerine, the operation temperature of extraction tower is 20~90 DEG C, pressure is 0.05~1MPa, acetophenone and 1- benzene
The molar flow of alcohol mixture and glycerine ratio is 1：0.6~10；
(2) the bottom of towe mixture that step (1) obtains is squeezed into rectifying in first rectifying column, tower top obtains acetophenone quality hundred
Divide the mixture of acetophenone of the concentration not less than 40% and 1- benzyl carbinols, bottom of towe obtains the mixture of 1- benzyl carbinols and glycerine,
First rectifying column operating pressure is 0.001~0.1Mpa, and operation temperature is the boiling point of system；
(3) the bottom of towe mixture that step (2) obtains is squeezed into rectifying in Second distillation column, tower top obtains the production of 1- benzyl carbinols
Product, bottom of towe obtain glycerine, and Second distillation column operating pressure is 0.001~0.1MPa, and operation temperature is the boiling point of system；
Scheme two comprises the following steps：
(1) acetophenone that the mass percentage concentration of acetophenone is 3%~95% is squeezed into first with 1- benzyl carbinol mixtures
Rectifying in rectifying column, tower top obtain the mixture of acetophenone of the acetophenone mass percentage concentration not less than 40% and 1- benzyl carbinols,
Bottom of towe obtains 1- benzyl carbinol products, and first rectifying column operating pressure is 0.001~0.1MPa, and operation temperature is the boiling point of system；
(2) overhead mixture that step (1) obtains is squeezed into extraction tower bottom, with glycerine in extraction tower counter current contacting
Extracted, product acetophenone is obtained at the top of extraction tower, bottom of towe obtains the mixture of acetophenone, 1- benzyl carbinols and glycerine, extraction
To take tower operation temperature be 20~90 DEG C, pressure is 0.05~1MPa, into the mixture of extraction tower bottom and mole of glycerine
Flow-rate ratio is 1：0.6~10；
(3) mixture of the acetophenone, 1- benzyl carbinols and the glycerine that obtain step (2) is squeezed into smart in Second distillation column
Evaporate, tower top obtains the mixture of acetophenone of the acetophenone mass percentage concentration not less than 40% and 1- benzyl carbinols, and bottom of towe obtains 1-
The mixture of benzyl carbinol and glycerine, Second distillation column operating pressure are 0.001~0.1MPa, and operation temperature is the boiling of system
Point；
(4) the 1- benzyl carbinols and the mixture of glycerine obtained step (3) squeezes into rectifying in third distillation column, and tower top obtains
To 1- benzyl carbinol products, bottom of towe obtains glycerine, and third distillation column operating pressure is 0.001~0.1MPa, and operation temperature is body
The boiling point of system；
Scheme three comprises the following steps：
(1) acetophenone and 1- benzyl carbinols mixture and glycerine for being 3%~95% by the mass percentage concentration of acetophenone
In molar ratio 1：Rectifying in first rectifying column is squeezed into after 0.6~10 mixing, tower top obtains acetophenone mass percentage concentration and is not less than
40% acetophenone and the mixture of 1- benzyl carbinols, bottom of towe obtain 1- benzyl carbinols and glycerol mixture, first rectifying column operation
Pressure is 0.001~0.1MPa, and operation temperature is the boiling point of system；
(2) the 1- benzyl carbinols and glycerol mixture obtained step (1) squeezes into rectifying in Second distillation column, the second rectifying
Column overhead obtains product 1- benzyl carbinols, and Second distillation column bottom of towe obtains glycerine, and Second distillation column operating pressure is 0.001~
0.1MPa, operation temperature are the boiling point of system；Acetophenone that step (1) first rectifying column tower top is obtained and 1- benzyl carbinols it is mixed
Compound squeezes into extraction tower, and counter current contacting is extracted in extraction tower with glycerine, and acetophenone product is obtained at the top of extraction tower, extracts
Tower bottom of towe is taken to obtain the mixture of acetophenone, 1- benzyl carbinols and glycerine, extraction tower operation temperature is 20~90 DEG C, pressure is
0.05~1Mpa, acetophenone and the mixture of 1- benzyl carbinols and the molar flow ratio of glycerine into extraction tower are 1：0.6~
10。
As the preferred embodiment of this programme, the acetophenone mass percentage concentration that can obtain the step of scheme one (2) is not
The mixture of acetophenone and 1- benzyl carbinols less than 40% utilizes as the bottom of towe feeding cycle of extraction tower.
As the preferred embodiment of this programme, the glycerine that the step of scheme one (3) can be obtained its as extraction tower
Tower top feeding cycle utilizes.
As the preferred embodiment of this programme, the acetophenone that the step of scheme two (3) can be obtained and 1- benzyl carbinols it is mixed
Compound recycles as the bottom feed of extraction tower.
As the preferred embodiment of this programme, tower that can be using the glycerine that the step of scheme two (4) obtains as extraction tower
Feeding cycle is pushed up to utilize.
As the preferred embodiment of this programme, the glycerine that the step of scheme three (2) Second distillation column bottom of towe can be obtained
Utilized as extraction column overhead feed cycle.
As the preferred embodiment of this programme, acetophenone, the 1- benzene that the step of scheme three (2) extraction tower bottom of towe can be obtained
The mixture of ethanol and glycerine utilizes as the feeding cycle of first rectifying column.
The present invention basic ideas be：
(a) the specific physical property dissolved each other using glycerine and the mutual slightly soluble of acetophenone, glycerine and 1- benzyl carbinols, is taken
Extracting operation, you can most of acetophenone is realized with 1- benzyl carbinols and separated.
Although three acetophenone, 1- benzyl carbinols and glycerine components are mixed with mixture after (b) separating, due to the third three
The relative volatility difference of the presence of alcohol, acetophenone and 1- benzyl carbinols becomes big, only need to use simple rectifying, you can by acetophenone from
Separated in mixture, tower top obtains the mixture of acetophenone and 1- benzyl carbinols, and bottom of towe obtains 1- benzyl carbinols and glycerine
Mixture.The acetophenone and the mixture of 1- benzyl carbinols that tower top obtains can be recycled directly back in extraction tower further utilize extraction behaviour
Make separation and recovery acetophenone.
(c) the 1- benzyl carbinols and the boiling point difference of glycerine obtained is huge, is recyclable product 1- benzene through simple rectifying
Ethanol, the high boiling glycerine of bottom of towe can be recycled directly back to further reuse in extraction tower.
Compared with prior art, advantages of the present invention is：
1st, technique is simple, and separation condition is gentle, and technique is operated using continous way, simple and stable, and separation equipment is only conventional
Rectifying column and extraction tower, operating condition is gentle；
2nd, the three wastes are few, energy-conserving and environment-protective, and the third component glycerine chemical property that newly adds is stable, not with component benzene to be separated
Ethyl ketone or 1- benzyl carbinols chemically react, and are not easy to that the side reactions such as self-polymerization occur, reusable；
3rd, good separating effect, product recovery rate are high, the purity for the acetophenone product for being finally recovered to obtain more than 98.0%,
The rate of recovery is more than 99.9%；The rate of recovery of 1- benzyl carbinol products is more than 99.5%, and purity is more than 99.0%.
Brief description of the drawings
Fig. 1 is the process chart of embodiment 1~4；
Fig. 2 is the process chart of embodiment 5~8；
Fig. 3 is the process chart of embodiment 9~12.
1 is extraction tower, and 2 be first rectifying column, and 3 be Second distillation column, and 4 be third distillation column.
Embodiment
The present invention is described in further detail with accompanying drawing with reference to embodiments, but the present invention is not limited to described reality
Apply example.
Extraction tower in embodiment is that an internal diameter is 200mm, high 4000mm reciprocating sieve plate extraction column.Rectifying column is straight
Footpath 400mm, high 8000m enamel rectifying column.
Embodiment 1
A kind of separation method of acetophenone and 1- benzyl carbinol, as shown in figure 1, comprising the following steps：
(1) acetophenone that the mass percentage concentration of acetophenone is 87.2% is squeezed into extraction tower 1 with 1- benzyl carbinol mixtures
Bottom, counter current contacting is extracted in extraction tower 1 with the extractant glycerine from the addition of the top of extraction tower 1, the top of extraction tower 1
Product acetophenone (sampling analysis purity is 98.2%, the acetophenone rate of recovery 99.99%) is obtained, bottom of towe obtains acetophenone, 1- benzene
The mixture of ethanol and glycerine, the operation temperature of extraction tower are 90.0 DEG C, pressure 1MPa, glycerine and acetophenone and 1- benzene second
The molar flow ratio of alcohol mixture is 0.915:1；
(2) the bottom of towe mixture that step (1) obtains is squeezed into rectifying in first rectifying column 2, tower top obtains acetophenone quality
Percentage concentration is 61.2% acetophenone and the mixture of 1- benzyl carbinols, is utilized as the bottom of towe feeding cycle of extraction tower 1,
The bottom of towe of first rectifying column 2 obtains the mixture of 1- benzyl carbinols and glycerine, and the operating pressure of first rectifying column 2 is 0.1MPa, tower top
Temperature with bottom of towe is the boiling point of system；
(3) the bottom of towe mixture that step (2) obtains is squeezed into rectifying in Second distillation column 3, tower top obtains the production of 1- benzyl carbinols
Product (sampling analysis purity is 99.1%, the 1- benzyl carbinols rate of recovery 99.56%), bottom of towe obtains extractant glycerine, as
The tower top feeding cycle of extraction tower 1 utilizes, and the operating pressure of Second distillation column 2 is 0.1MPa, and the temperature of tower top and bottom of towe is body
The boiling point of system.
Embodiment 2
A kind of separation method of acetophenone and 1- benzyl carbinol, as shown in figure 1, comprising the following steps：
(1) acetophenone that the mass percentage concentration of acetophenone is 41.6% is squeezed into extraction tower 1 with 1- benzyl carbinol mixtures
Bottom, counter current contacting is extracted in extraction tower 1 with the extractant glycerine from the addition of the top of extraction tower 1, the top of extraction tower 1
Product acetophenone (sampling analysis purity is 98.1%, the acetophenone rate of recovery 99.92%) is obtained, bottom of towe obtains acetophenone, 1- benzene
The mixture of ethanol and glycerine, the operation temperature of extraction tower are 70.0 DEG C, pressure 0.1MPa, glycerine and acetophenone and 1- benzene
The molar flow ratio of alcohol mixture is 6:1；
(2) the bottom of towe mixture that step (1) obtains is squeezed into rectifying in first rectifying column 2, tower top obtains acetophenone quality
Percentage concentration is 46.2% acetophenone and the mixture of 1- benzyl carbinols, is utilized as the bottom of towe feeding cycle of extraction tower 1,
The bottom of towe of first rectifying column 2 obtains the mixture of 1- benzyl carbinols and glycerine, and the operating pressure of first rectifying column 2 is 0.01MPa, tower top
Temperature with bottom of towe is the boiling point of system；
(3) the bottom of towe mixture that step (2) obtains is squeezed into rectifying in Second distillation column 3, tower top obtains the production of 1- benzyl carbinols
Product (sampling analysis purity is 99.4%, the 1- benzyl carbinols rate of recovery 99.68%), bottom of towe obtains extractant glycerine, as
The tower top feeding cycle of extraction tower 1 utilizes, and the operating pressure of Second distillation column 2 is 0.008MPa, and the temperature of tower top and bottom of towe is
The boiling point of system.
Embodiment 3
A kind of separation method of acetophenone and 1- benzyl carbinol, as shown in figure 1, comprising the following steps：
(1) acetophenone that the mass percentage concentration of acetophenone is 56.4% is squeezed into extraction tower 1 with 1- benzyl carbinol mixtures
Bottom, counter current contacting is extracted in extraction tower 1 with the extractant glycerine from the addition of the top of extraction tower 1, the top of extraction tower 1
Product acetophenone (sampling analysis purity is 98.1%, the acetophenone rate of recovery 99.96%) is obtained, bottom of towe obtains acetophenone, 1- benzene
The mixture of ethanol and glycerine, the operation temperature of extraction tower is 20.0 DEG C, pressure 0.05MPa, glycerine and acetophenone and 1-
The molar flow ratio of benzyl carbinol mixture is 10:1；
(2) the bottom of towe mixture that step (1) obtains is squeezed into rectifying in first rectifying column 2, tower top obtains acetophenone quality
Percentage concentration is 89.6% acetophenone and the mixture of 1- benzyl carbinols, is utilized as the bottom of towe feeding cycle of extraction tower 1,
The bottom of towe of first rectifying column 2 obtains the mixture of 1- benzyl carbinols and glycerine, and the operating pressure of first rectifying column 2 is 0.001MPa, tower
The temperature of top and bottom of towe is the boiling point of system；
(3) the bottom of towe mixture that step (2) obtains is squeezed into rectifying in Second distillation column 3, tower top obtains the production of 1- benzyl carbinols
Product (sampling analysis purity is 99.6%, the 1- benzyl carbinols rate of recovery 99.79%), bottom of towe obtains extractant glycerine, as
The tower top feeding cycle of extraction tower 1 utilizes, and the operating pressure of Second distillation column 2 is 0.001MPa, and the temperature of tower top and bottom of towe is
The boiling point of system.
Embodiment 4
A kind of separation method of acetophenone and 1- benzyl carbinol, as shown in figure 1, comprising the following steps：
(1) acetophenone that the mass percentage concentration of acetophenone is 74.1% is squeezed into extraction tower 1 with 1- benzyl carbinol mixtures
Bottom, counter current contacting is extracted in extraction tower 1 with the extractant glycerine from the addition of the top of extraction tower 1, the top of extraction tower 1
Product acetophenone (sampling analysis purity is 98.3%, the acetophenone rate of recovery 99.88%) is obtained, bottom of towe obtains acetophenone, 1- benzene
The mixture of ethanol and glycerine, the operation temperature of extraction tower are 45.0 DEG C, pressure 0.3MPa, glycerine and acetophenone and 1- benzene
The molar flow ratio of alcohol mixture is 0.6:1；
(2) the bottom of towe mixture that step (1) obtains is squeezed into rectifying in first rectifying column 2, tower top obtains acetophenone quality
Percentage concentration is 66.5% acetophenone and the mixture of 1- benzyl carbinols, is utilized as the bottom of towe feeding cycle of extraction tower 1,
The bottom of towe of first rectifying column 2 obtains the mixture of 1- benzyl carbinols and glycerine, and the operating pressure of first rectifying column 2 is 0.004MPa, tower
The temperature of top and bottom of towe is the boiling point of system；
(3) the bottom of towe mixture that step (2) obtains is squeezed into rectifying in Second distillation column 3, tower top obtains the production of 1- benzyl carbinols
Product (sampling analysis purity is 99.5%, the 1- benzyl carbinols rate of recovery 99.82%), bottom of towe obtains extractant glycerine, as
The tower top feeding cycle of extraction tower 1 utilizes, and the operating pressure of Second distillation column 2 is 0.003MPa, and the temperature of tower top and bottom of towe is
The boiling point of system.
Embodiment 5
A kind of separation method of acetophenone and 1- benzyl carbinol, as shown in Fig. 2 comprising the following steps：
(1) acetophenone that the mass percentage concentration of acetophenone is 28% is squeezed into first rectifying column with 1- benzyl carbinol mixtures
Just rectifying in 2, tower top obtain the mixture of the acetophenone that acetophenone mass percentage concentration is 52% and 1- benzyl carbinols, and bottom of towe obtains
1- benzyl carbinols product (sampling analysis, purity 99.4%), the operating pressure of first rectifying column 2 are 0.1MPa, tower top and bottom of towe
Temperature is the boiling point of system；
(2) overhead mixture that step (1) obtains is squeezed into the bottom of extraction tower 1, with the extraction added from the top of extraction tower 1
Agent glycerine counter current contacting in extraction tower 1 is extracted, and the top of extraction tower 1 obtains product acetophenone, and (sampling analysis, purity are
98.2%), bottom of towe obtains the mixture of acetophenone, 1- benzyl carbinols and glycerine, and the operation temperature of extraction tower 1 is 44 DEG C, pressure
For 0.4MPa, the molar flow ratio into the glycerine at the top of extraction tower and the mixture for entering extraction tower bottom is 1：1；
(3) mixture of the acetophenone, 1- benzyl carbinols and the glycerine that obtain step (2) is squeezed into smart in Second distillation column 3
Evaporate, tower top obtains the mixture of acetophenone and 1- benzyl carbinols, and the mass percentage concentration of acetophenone is 62%, as extraction tower
1 bottom feed recycles, and the bottom of towe of Second distillation column 3 obtains the mixture of benzyl carbinol and glycerine, and Second distillation column 3 operates
Pressure is 0.05MPa, and the temperature of tower top and bottom of towe is the boiling point of system；
(4) mixture that step (3) is obtained to benzyl carbinol and glycerine squeezes into rectifying in third distillation column 4, and tower top obtains
1- benzyl carbinols product (sampling analysis, purity 99.4%), bottom of towe obtains extractant glycerine, using extractant glycerine as extraction
The tower top feeding cycle of tower is taken to utilize, the operating pressure of third distillation column 4 is 0.02MPa, and the temperature of tower top and bottom of towe is system
Boiling point.
Implementation result：The 1- benzyl carbinols rate of recovery 99.65%, the acetophenone rate of recovery 99.95%.
Embodiment 6
A kind of separation method of acetophenone and 1- benzyl carbinol, as shown in Fig. 2 comprising the following steps：
(1) acetophenone that the mass percentage concentration of acetophenone is 3% is squeezed into first rectifying column 2 with 1- benzyl carbinol mixtures
In just rectifying, tower top obtains the mixture of the acetophenone that acetophenone mass percentage concentration is 41% and 1- benzyl carbinols, and bottom of towe obtains
1- benzyl carbinols product (sampling analysis, purity 99.2%), the operating pressure of first rectifying column 2 are 0.02MPa, tower top and bottom of towe
Temperature is the boiling point of system；
(2) overhead mixture that step (1) obtains is squeezed into the bottom of extraction tower 1, with the extraction added from the top of extraction tower 1
Agent glycerine counter current contacting in extraction tower 1 is extracted, and the top of extraction tower 1 obtains product acetophenone, and (sampling analysis, purity are
98.1%), bottom of towe obtains the mixture of acetophenone, 1- benzyl carbinols and glycerine, and the operation temperature of extraction tower 1 is 20 DEG C, pressure
For 1.0MPa, the molar flow ratio into the glycerine at the top of extraction tower and the mixture for entering extraction tower bottom is 0.6：1；
(3) mixture of the acetophenone, 1- benzyl carbinols and the glycerine that obtain step (2) is squeezed into smart in Second distillation column 3
Evaporate, tower top obtains the mixture of acetophenone and 1- benzyl carbinols, and the mass percentage concentration of acetophenone is 48%, as extraction tower
1 bottom feed recycles, and the bottom of towe of Second distillation column 3 obtains the mixture of benzyl carbinol and glycerine, and Second distillation column 3 operates
Pressure is 0.1MPa, and the temperature of tower top and bottom of towe is the boiling point of system；
(4) mixture that step (3) is obtained to benzyl carbinol and glycerine squeezes into rectifying in third distillation column 4, and tower top obtains
1- benzyl carbinols product (sampling analysis, purity 99.2%), bottom of towe obtains extractant glycerine, using extractant glycerine as extraction
The tower top feeding cycle of tower is taken to utilize, the operating pressure of third distillation column 4 is 0.1MPa, and the temperature of tower top and bottom of towe is system
Boiling point.
Implementation result：The 1- benzyl carbinols rate of recovery 99.91%, the acetophenone rate of recovery 99.92%.
Embodiment 7
A kind of separation method of acetophenone and 1- benzyl carbinol, as shown in Fig. 2 comprising the following steps：
(1) acetophenone that the mass percentage concentration of acetophenone is 95% is squeezed into first rectifying column with 1- benzyl carbinol mixtures
Just rectifying in 2, tower top obtain the mixture of the acetophenone that acetophenone mass percentage concentration is 96.2% and 1- benzyl carbinols, and bottom of towe obtains
To 1- benzyl carbinols product (sampling analysis, purity 99.7%), the operating pressure of first rectifying column 2 is 0.001MPa, tower top and tower
The temperature at bottom is the boiling point of system；
(2) overhead mixture that step (1) obtains is squeezed into the bottom of extraction tower 1, with the extraction added from the top of extraction tower 1
Agent glycerine counter current contacting in extraction tower 1 is extracted, and the top of extraction tower 1 obtains product acetophenone, and (sampling analysis, purity are
98.6%), bottom of towe obtains the mixture of acetophenone, 1- benzyl carbinols and glycerine, and the operation temperature of extraction tower 1 is 90 DEG C, pressure
For 0.1MPa, the molar flow ratio into the glycerine at the top of extraction tower and the mixture for entering extraction tower bottom is 10：1；
(3) mixture of the acetophenone, 1- benzyl carbinols and the glycerine that obtain step (2) is squeezed into smart in Second distillation column 3
Evaporate, tower top obtains the mixture of acetophenone and 1- benzyl carbinols, and the mass percentage concentration of acetophenone is 97.8%, as extraction
The bottom feed of tower 1 is recycled, and the bottom of towe of Second distillation column 3 obtains the mixture of benzyl carbinol and glycerine, and Second distillation column 3 is grasped
It is 0.001MPa to make pressure, and the temperature of tower top and bottom of towe is the boiling point of system；
(4) mixture that step (3) is obtained to benzyl carbinol and glycerine squeezes into rectifying in third distillation column 4, and tower top obtains
1- benzyl carbinols product (sampling analysis, purity 99.1%), bottom of towe obtains extractant glycerine, using extractant glycerine as extraction
The tower top feeding cycle of tower is taken to utilize, the operating pressure of third distillation column 4 is 0.001MPa, and the temperature of tower top and bottom of towe is system
Boiling point.
Implementation result：The 1- benzyl carbinols rate of recovery 99.52%, the acetophenone rate of recovery 99.99%.
Embodiment 8
A kind of separation method of acetophenone and 1- benzyl carbinol, as shown in Fig. 2 comprising the following steps：
(1) acetophenone that the mass percentage concentration of acetophenone is 56% is squeezed into first rectifying column with 1- benzyl carbinol mixtures
Just rectifying in 2, tower top obtain the mixture of the acetophenone that acetophenone mass percentage concentration is 67% and 1- benzyl carbinols, and bottom of towe obtains
1- benzyl carbinols product (sampling analysis, purity 99.6%), the operating pressure of first rectifying column 2 are 0.005MPa, tower top and bottom of towe
Temperature be system boiling point；
(2) overhead mixture that step (1) obtains is squeezed into the bottom of extraction tower 1, with the extraction added from the top of extraction tower 1
Agent glycerine counter current contacting in extraction tower 1 is extracted, and the top of extraction tower 1 obtains product acetophenone, and (sampling analysis, purity are
98.8%), bottom of towe obtains the mixture of acetophenone, 1- benzyl carbinols and glycerine, and the operation temperature of extraction tower 1 is 65 DEG C, pressure
For 0.05MPa, the molar flow ratio into the glycerine at the top of extraction tower and the mixture for entering extraction tower bottom is 3：1；
(3) mixture of the acetophenone, 1- benzyl carbinols and the glycerine that obtain step (2) is squeezed into smart in Second distillation column 3
Evaporate, tower top obtains the mixture of acetophenone and 1- benzyl carbinols, and the mass percentage concentration of acetophenone is 78%, as extraction tower
1 bottom feed recycles, and the bottom of towe of Second distillation column 3 obtains the mixture of benzyl carbinol and glycerine, and Second distillation column 3 operates
Pressure is 0.004MPa, and the temperature of tower top and bottom of towe is the boiling point of system；
(4) mixture that step (3) is obtained to benzyl carbinol and glycerine squeezes into rectifying in third distillation column 4, and tower top obtains
1- benzyl carbinols product (sampling analysis, purity 99.5%), bottom of towe obtains extractant glycerine, using extractant glycerine as extraction
The tower top feeding cycle of tower is taken to utilize, the operating pressure of third distillation column 4 is 0.003MPa, and the temperature of tower top and bottom of towe is system
Boiling point.
Implementation result：The 1- benzyl carbinols rate of recovery 99.55%, the acetophenone rate of recovery 99.92%.
Embodiment 9
A kind of separation method of acetophenone and 1- benzyl carbinol, as shown in figure 3, comprising the following steps：
(1) acetophenone and 1- benzyl carbinol mixtures for being 34% by the mass percentage concentration of extractant glycerine and acetophenone
In molar ratio 1:Rectifying in first rectifying column 2 is squeezed into after 1 mixing, tower top obtains the benzene second that acetophenone mass percentage concentration is 56%
The mixture of ketone and 1- benzyl carbinols, bottom of towe obtain 1- benzyl carbinols and glycerol mixture, and the operating pressure of first rectifying column 2 is
The temperature of 0.1MPa, tower top and bottom of towe is the boiling point of system；
(2) acetophenone and the mixture of 1- benzyl carbinols obtained the tower top of step (1) first rectifying column 2 squeezes into extraction tower 1
Bottom, counter current contacting is extracted in extraction tower 1 with the fresh extractant glycerine from the addition of the top of extraction tower 1, extraction tower 1
Top obtains acetophenone product, and the bottom of towe of extraction tower 1 obtains the mixture of acetophenone, 1- benzyl carbinols and glycerine, as
The feeding cycle of one rectifying column 2 utilizes；The 1- benzyl carbinols and glycerol mixture that step (1) is obtained squeeze into Second distillation column 3
Middle rectifying, the tower top of Second distillation column 3 obtain product 1- benzyl carbinols, and the bottom of towe of Second distillation column 3 obtains glycerine, using glycerine as
The tower top feed cycle of extraction tower 1 utilizes, and the operating pressure of Second distillation column 3 is 0.1MPa, and the temperature of tower top and bottom of towe is system
Boiling point.The operation temperature of extraction tower 1 is 40 DEG C, pressure 1MPa, is extracted into the fresh glycerine at the top of extraction tower with entering
The molar flow ratio of the acetophenone of tower bottom and the mixture of 1- benzyl carbinols is 1:1；
Sampled analysis, 1- benzyl carbinols product purity are 99.8%, the rate of recovery 99.56%；Acetophenone product purity is
98.4%, the rate of recovery 99.91%.
Embodiment 10
A kind of separation method of acetophenone and 1- benzyl carbinol, as shown in figure 3, comprising the following steps：
(1) acetophenone and 1- benzyl carbinol mixtures for being 3% by the mass percentage concentration of extractant glycerine and acetophenone
In molar ratio 0.6:Rectifying in first rectifying column 2 is squeezed into after 1 mixing, tower top obtains the benzene that acetophenone mass percentage concentration is 43%
The mixture of ethyl ketone and 1- benzyl carbinols, bottom of towe obtain 1- benzyl carbinols and glycerol mixture, and the operating pressure of first rectifying column 2 is
The temperature of 0.001MPa, tower top and bottom of towe is the boiling point of system；
(2) acetophenone and the mixture of 1- benzyl carbinols obtained the tower top of step (1) first rectifying column 2 squeezes into extraction tower 1
Bottom, counter current contacting is extracted in extraction tower 1 with the fresh extractant glycerine from the addition of the top of extraction tower 1, extraction tower 1
Top obtains acetophenone product, and the bottom of towe of extraction tower 1 obtains the mixture of acetophenone, 1- benzyl carbinols and glycerine, as
The feeding cycle of one rectifying column 2 utilizes；The 1- benzyl carbinols and glycerol mixture that step (1) is obtained squeeze into Second distillation column 3
Middle rectifying, the tower top of Second distillation column 3 obtain product 1- benzyl carbinols, and the bottom of towe of Second distillation column 3 obtains glycerine, using glycerine as
The tower top feed cycle of extraction tower 1 utilizes, and the operating pressure of Second distillation column 3 is 0.001MPa, and the temperature of tower top and bottom of towe is body
The boiling point of system.The operation temperature of extraction tower 1 is 20 DEG C, pressure 0.05MPa, into the fresh glycerine at the top of extraction tower with entering
The molar flow ratio for extracting the acetophenone of tower bottom and the mixture of 1- benzyl carbinols is 0.6:1.
Implementation result：1- benzyl carbinols product purity is 99.1%, the rate of recovery 99.91%；Acetophenone product purity is
98.1%, the rate of recovery 99.91%.
Embodiment 11
A kind of separation method of acetophenone and 1- benzyl carbinol, as shown in figure 3, comprising the following steps：
(1) acetophenone and 1- benzyl carbinol mixtures for being 95% by the mass percentage concentration of extractant glycerine and acetophenone
In molar ratio 10:Rectifying in first rectifying column 2 is squeezed into after 1 mixing, it is 96.8% that tower top, which obtains acetophenone mass percentage concentration,
The mixture of acetophenone and 1- benzyl carbinols, bottom of towe obtain 1- benzyl carbinols and glycerol mixture, and the operating pressure of first rectifying column 2 is
The temperature of 0.01MPa, tower top and bottom of towe is the boiling point of system；
(2) acetophenone and the mixture of 1- benzyl carbinols obtained the tower top of step (1) first rectifying column 2 squeezes into extraction tower 1
Bottom, counter current contacting is extracted in extraction tower 1 with the fresh extractant glycerine from the addition of the top of extraction tower 1, extraction tower 1
Top obtains acetophenone product, and the bottom of towe of extraction tower 1 obtains the mixture of acetophenone, 1- benzyl carbinols and glycerine, as
The feeding cycle of one rectifying column 2 utilizes；The 1- benzyl carbinols and glycerol mixture that step (1) is obtained squeeze into Second distillation column 3
Middle rectifying, the tower top of Second distillation column 3 obtain product 1- benzyl carbinols, and the bottom of towe of Second distillation column 3 obtains glycerine, using glycerine as
The tower top feed cycle of extraction tower 1 utilizes, and the operating pressure of Second distillation column 3 is 0.01MPa, and the temperature of tower top and bottom of towe is system
Boiling point.The operation temperature of extraction tower 1 is 90 DEG C, pressure 0.1MPa, is extracted into the fresh glycerine at the top of extraction tower with entering
It is 10 to take the molar flow ratio of the acetophenone of tower bottom and the mixture of 1- benzyl carbinols:1.
Implementation result：1- benzyl carbinols product purity is 99.1%, the rate of recovery 99.51%；Acetophenone product purity is
99.1%, the rate of recovery 99.99%.
Embodiment 12
A kind of separation method of acetophenone and 1- benzyl carbinol, as shown in figure 3, comprising the following steps：
(1) acetophenone and 1- benzyl carbinol mixtures for being 46% by the mass percentage concentration of extractant glycerine and acetophenone
In molar ratio 5:Rectifying in first rectifying column 2 is squeezed into after 1 mixing, tower top obtains the benzene second that acetophenone mass percentage concentration is 82%
The mixture of ketone and 1- benzyl carbinols, bottom of towe obtain 1- benzyl carbinols and glycerol mixture, and the operating pressure of first rectifying column 2 is
The temperature of 0.05MPa, tower top and bottom of towe is the boiling point of system；
(2) acetophenone and the mixture of 1- benzyl carbinols obtained the tower top of step (1) first rectifying column 2 squeezes into extraction tower 1
Bottom, counter current contacting is extracted in extraction tower 1 with the fresh extractant glycerine from the addition of the top of extraction tower 1, extraction tower 1
Top obtains acetophenone product, and the bottom of towe of extraction tower 1 obtains the mixture of acetophenone, 1- benzyl carbinols and glycerine, as
The feeding cycle of one rectifying column 2 utilizes；The 1- benzyl carbinols and glycerol mixture that step (1) is obtained squeeze into Second distillation column 3
Middle rectifying, the tower top of Second distillation column 3 obtain product 1- benzyl carbinols, and the bottom of towe of Second distillation column 3 obtains glycerine, using glycerine as
The tower top feed cycle of extraction tower 1 utilizes, and the operating pressure of Second distillation column 3 is 0.05MPa, and the temperature of tower top and bottom of towe is system
Boiling point.The operation temperature of extraction tower 1 is 70 DEG C, pressure 0.3MPa, is extracted into the fresh glycerine at the top of extraction tower with entering
It is 5 to take the molar flow ratio of the acetophenone of tower bottom and the mixture of 1- benzyl carbinols:1.
Implementation result：1- benzyl carbinols product purity is 99.4%, the rate of recovery 99.76%；Acetophenone product purity is
98.2%, the rate of recovery 99.95%.
Claims (3)
1. the separation method of a kind of acetophenone and 1- benzyl carbinols, it is characterised in that according to acetophenone and 1- benzyl carbinols in glycerine
Solubility and relative volatility it is different, both separation are realized using the coupling operation of extraction and rectifying, are specifically included following
Step：
(1) acetophenone of the mass percentage concentration of acetophenone not less than 40% is squeezed into extraction tower with 1- benzyl carbinol mixtures, with
Glycerine counter current contacting in extraction tower is extracted, and tower top obtains product acetophenone, bottom of towe obtain acetophenone, 1- benzyl carbinols and
The mixture of glycerine, the operation temperature of extraction tower is 20~90 DEG C, pressure is 0.05~1MPa, and acetophenone mixes with 1- benzyl carbinols
The molar flow of compound and glycerine ratio is 1：0.6~10；
(2) the bottom of towe mixture that step (1) obtains is squeezed into rectifying in first rectifying column, it is dense that tower top obtains acetophenone quality percentage
The mixture of acetophenone of the degree not less than 40% and 1- benzyl carbinols, bottom of towe obtain the mixture of 1- benzyl carbinols and glycerine, and first
Rectifying column operating pressure is 0.001~0.1Mpa, and operation temperature is the boiling point of system；
(3) the bottom of towe mixture that step (2) obtains is squeezed into rectifying in Second distillation column, tower top obtains 1- benzyl carbinol products, tower
Bottom obtains glycerine, and Second distillation column operating pressure is 0.001~0.1MPa, and operation temperature is the boiling point of system.
2. the separation method of acetophenone according to claim 1 and 1- benzyl carbinols, it is characterised in that obtain step (2)
The mixture of acetophenone of the acetophenone mass percentage concentration not less than 40% and 1- benzyl carbinols follows as the bottom of towe charging of extraction tower
Ring utilizes.
3. the separation method of acetophenone according to claim 1 and 1- benzyl carbinols, it is characterised in that obtain step (3)
Its tower top feeding cycle utilization as extraction tower of glycerine.
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| CN201710140968.8A CN106866396B (en) | 2015-10-28 | 2015-10-28 | Method for separating acetophenone and 1-phenethyl alcohol |
| CN201710140967.3A CN106866395B (en) | 2015-10-28 | 2015-10-28 | Method for separating acetophenone and 1-phenethyl alcohol |
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