CN109134197A - A method of using alkanes entrainer from dichlorohydrin hydrochloric acid solution separating dichloropropanol - Google Patents
A method of using alkanes entrainer from dichlorohydrin hydrochloric acid solution separating dichloropropanol Download PDFInfo
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- CN109134197A CN109134197A CN201811218643.8A CN201811218643A CN109134197A CN 109134197 A CN109134197 A CN 109134197A CN 201811218643 A CN201811218643 A CN 201811218643A CN 109134197 A CN109134197 A CN 109134197A
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- dichlorohydrin
- hydrochloric acid
- acid solution
- alkanes
- entrainer
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- 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
- C07C29/82—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation by azeotropic distillation
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- 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
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- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
Abstract
The invention discloses a kind of methods using alkanes entrainer separating dichloropropanol from dichlorohydrin hydrochloric acid solution, specific steps are as follows: the alkanes entrainer of azeotrope with water is added into dichlorohydrin aqueous hydrochloric acid solution, heating makes system reach azeotropic, through rectifying cooling procedure, realize the separation of hydrochloric acid solution and alkanes entrainer in rectifying component, the component that non-rectifying goes out obtains high-purity dichlorohydrin, the recycling of alkanes entrainer through air-distillation.This method is easy to operate, avoids many and diverse operation repeatedly extracted, separative efficiency is high, and cost is relatively low；The equal recoverable of all materials, raw material availability is high, reduces environmental pollution.
Description
Technical field
The invention belongs to fine chemical product fields, and in particular to a kind of molten from dichlorohydrin hydrochloric acid using alkanes entrainer
The method of separating dichloropropanol in liquid.
Background technique
Chloro- 1, the 2- propylene oxide of epoxychloropropane, that is, 3- is a kind of important Organic Chemicals and synthetic intermediate, can
Solvent as cellulose esters, resin and cellulose ether, and production surfactant, medicine, pesticide, coating, adhesive, from
Sub-exchange resin, plasticizer, glycerol derivatives and glycidyl derivatives raw material, be widely used in chemical industry, light industry, doctor
The industries such as medicine, electronics.
Epoxy chloropropane production method mainly has 3 kinds at present: using propylene as the propylene high-temperature chloridising of raw material, acetic acid third
Enester method and using glycerol as the glycerin chlorination method of raw material.The intermediate product of three kinds of methods can all form dichlorohydrin-water-hydrogen chloride
Azeotropic mixture.Using dichlorohydrin hydrogen chloride mixed aqueous solution and calcium hydroxide, sodium hydroxide occurs saponification and prepares epoxy
When chloropropane process, with lye neutralization reaction can occur for the hydrogen chloride in azeotropic mixture, cause saponification process alkali consumption higher, generate
A large amount of chlorate, while sewage pollution is serious.If the dichloro in dichlorohydrin-water-hydrogen chloride azeotropic mixture can be isolated
Propyl alcohol will be solved the problem above-mentioned effectively.Separating dichloropropanol-water-hydrogen chloride azeotropic mixture method mainly uses alkane at present
Hydrocarbon organic solvent carries out extraction and separation.Jiangsu Yangnong Chemical Group Co., Ltd discloses one in CN200610161842.0
The method of kind extraction and separation dichlorohydrin from dichlorohydrin hydrochloric acid solution uses halogenated hydrocarbon, fragrant ethers, phosphoric acid ester alkane
Hydrocarbon organic solvent is as extractant separating-purifying dichlorohydrin.ShanghaiChlorine and Alkali Chemical Co Ltd
The method of preparing epoxy chloropropane by using hydrochloric acid water solution of dichlorohydrin is disclosed in CN200910046282.8, using alcohols, aromatic hydrocarbons
The alkanes organic solvent such as class or ethers, purification by liquid extraction dichlorohydrin.It is generally required using alkanes organic solvent extraction and separation
Multitple extraction needs to increase multitple extraction equipment, and operational sequence is relatively cumbersome, causes the wasting of resources and environmental pollution, significantly
Increase production cost.
One kind is disclosed in my 107935818 A of house journal CN to separate from dichlorohydrin-water-hydrogen chloride azeotropic mixture
The method of dichlorohydrin adjusts pH value using ammonium hydroxide, and stratification, to obtain dichlorohydrin pure through vacuum distillation for lower layer's organic phase
Product；Upper strata aqueous phase decrease temperature crystalline obtains ammonia chloride crystal and its mother liquor, and the two can be used as organic phosphorus products material and use, still
This method needs to continually add a large amount of ammonium hydroxide during neutralisation treatment, repetitive operation, and technique overall cost is higher.
Summary of the invention
To solve the problems, such as that operational sequence is relatively cumbersome during the prior art exists, the wasting of resources and environmental pollution, this hair
It is bright to provide a kind of method using alkanes entrainer separating dichloropropanol from dichlorohydrin hydrochloric acid solution.
A method of using alkanes entrainer from dichlorohydrin hydrochloric acid solution separating dichloropropanol, using following behaviour
Make step:
(1) the alkanes entrainer of dichlorohydrin hydrochloric acid solution and azeotrope with water is placed in reaction kettle, reaction kettle is sequentially connected
Rectifier unit, condensation dress and division box；
(2) heating reaction kettle makes the solution azeotropy rectifying in reaction kettle, and rectifying component is transferred to division box by condensing unit
In, stratification, hydrochloric acid solution and alkanes entrainer separate；
(3) component that non-rectifying goes out in reaction kettle obtains dichlorohydrin through air-distillation.
Preferably, the alkanes organic solvent of azeotrope with water as described in step (1) can be hexamethylene, n-hexane and just
Any one in heptane.
Preferably, dichlorohydrin hydrochloric acid solution as described in step (1) is that glycerin chlorination method prepares epoxychloropropane process
Middle generation, the mass ratio of dichlorohydrin and hydrochloric acid solution is 25 ~ 35:62 ~ 78.
Preferably, the quality of the alkanes entrainer Yu dichlorohydrin hydrochloric acid solution of azeotrope with water as described in step (1)
Than for 0.5 ~ 4:1.
Preferably, the quality of the alkanes entrainer Yu dichlorohydrin hydrochloric acid solution of azeotrope with water as described in step (1)
Than for 1 ~ 4:1.
Preferably, the filler material of rectifier unit described in step (1) is Raschig ring, helical ring, ceramic ring, saddle type expectation, coke
Fastly, one or more of quartz, glass spring and insulation magnetic bead, filler accumulation mode is to dissipate heap.
Preferably, azeotropic distillation temperature described in step (2) is 62 ~ 70 DEG C, and the azeotropic distillation time is 4 ~ 12h.
Preferably, air-distillation temperature described in step (3) is 70 ~ 100 DEG C.
Dichlorohydrin hydrochloric acid solution is a kind of triplex mixture system containing dichlorohydrin, hydrogen chloride and water in the present invention,
And dichloropropanol content is higher, by extracting, distilling etc., direct methods separation and Extraction high-purity dichlorohydrin difficulty is big, the rate of recovery
It is low, at high cost, it selects hexamethylene, n-hexane, normal heptane etc. that can act on water and generates the low of azeotropic and solubility very little in water
Boiling point alkanes water entrainer is added in dichlorohydrin hydrochloric acid solution and forms the new azeotropic system of alkanes-hydrochloric acid, passes through azeotropic
Hydrochloric acid is separated the organic solvent isolated without introducing other organic impurities and can recycled by rectifying, condensation, division box
As system water entrainer.
The utility model has the advantages that
(1) it chooses the low boiling point alkanes organic solvent of azeotrope with water and dichlorohydrin hydrochloric acid solution forms new azeotropic system,
The dichlorohydrin purity is high isolated, the rate of recovery is high, and the hydrochloric acid solution Determination of Residual Organic Solvents isolated is small, does not influence product
Using and security performance, effectively prevent organic solvent existing for conventional method and repeatedly extract that consumption is big, organic solvent residual
The problem of amount is high and energy consumption is high.
(2) this method is easy to operate, and alkanes organic solvent is recyclable, and cost is relatively low, non-environmental-pollution.
Specific embodiment
It elaborates below to the embodiment of the present invention, the present embodiment carries out under the premise of the technical scheme of the present invention
Implement, the detailed implementation method and specific operation process are given, but protection scope of the present invention is not limited to following implementation
Example.
In the embodiment of the present invention, dichlorohydrin hydrochloric acid solution is to generate during glycerin chlorination method produces epoxychloropropane
, the mass fraction of dichlorohydrin and hydrochloric acid solution is other are as follows: dichlorohydrin 35%, hydrochloric acid solution 65%.
Embodiment 1
(1) 200 g hexamethylenes and 200 g dichlorohydrin hydrochloric acid solutions are added in three-necked flask, three-necked flask top successively connects
Rectifying column, condenser, water segregator and device for absorbing tail gas are connect, the filler of rectifying column is glass spring, and filler accumulation mode is scattered
Heap；Carrying out heating to three-necked flask by oil bath makes azeotropic system flow back, and temperature is about 70 DEG C, and the system azeotropic distillation time is 7
H, rectifying group lease making water segregator separate mass fraction be 23% 125 g of hydrochloric acid solution, the rate of recovery 96.15%, organic solvent is residual
Stay 10 ppm；
(2) dichlorohydrin and cyclohexane mixtures separate to obtain 67.48 g of dichlorohydrin, the rate of recovery through 82 ± 1 DEG C of normal pressure distillations
96.4%, purity 99.2%；
(3) merge hexamethylene totally 198 g of step (1) and (2) separation and recovery, the rate of recovery 99%, the hexamethylene of recycling, which is recycled, to be made
With.
Embodiment 2
(1) 200 g n-hexanes and 200 g dichlorohydrin hydrochloric acid solutions are placed in three-necked flask, three-necked flask top successively connects
Rectifying column, condenser, water segregator and device for absorbing tail gas are connect, the filler of rectifying column is Raschig ring, helical ring；By oil bath to three
Mouth flask, which carries out heating, makes azeotropic system flow back, and temperature is about 62 DEG C, and the system azeotropic distillation time is 8 h, rectifying group lease making point
Hydrophone separate mass fraction be 24% 122 g of hydrochloric acid solution, the rate of recovery 93.85%, 25 ppm of organic solvent residual；
(2) dichlorohydrin and hexane mixture separate to obtain 67.27 g of dichlorohydrin, the rate of recovery through 70 ± 1 DEG C of normal pressure distillations
96.1%, purity 99.1%；
(3) merge step (1) and (2) separation and recovery n-hexane totally 196 g, 98 % of the rate of recovery, the n-hexane of recycling is recyclable to be made
With.
Embodiment 3
(1) 400 g hexamethylenes and 200 g dichlorohydrin hydrochloric acid solutions are added in three-necked flask, three-necked flask is placed in oil bath
In pot, three-necked flask top is sequentially connected rectifying column, condenser, water segregator and device for absorbing tail gas, and the filler of rectifying column is saddle
Shape is expected, and filler accumulation mode is to dissipate heap；Carrying out heating to three-necked flask by oil bath makes azeotropic system flow back, and temperature is about 70
DEG C, the system azeotropic distillation time be 5 h, rectifying group lease making water segregator separate mass fraction be 24.1% hydrochloric acid solution 120
G, the rate of recovery 92.3%, 20 ppm of organic solvent residual；
(2) dichlorohydrin and cyclohexane mixtures separate to obtain 67.9 g of dichlorohydrin, the rate of recovery through 82 ± 1 DEG C of normal pressure distillations
97.0%, purity 99.3%；
(3) merge step (1) and (2) separation and recovery hexamethylene totally 392 g, the rate of recovery 98%, the hexamethylene of recycling is recyclable to be made
With.
Embodiment 4
(1) 800 g normal heptanes and 200 g dichlorohydrin hydrochloric acid solutions are added in three-necked flask, three-necked flask top successively connects
Rectifying column, condenser, water segregator and device for absorbing tail gas are connect, the filler of rectifying column is insulation magnetic bead, and filler accumulation mode is scattered
Heap；Carrying out heating to three-necked flask by oil bath makes azeotropic system flow back, and temperature is about 62 DEG C, and the system azeotropic distillation time is 8
H, rectifying group lease making water segregator separate mass fraction be 24.2% hydrochloric acid solution 116g, the rate of recovery 89.23%, organic solvent is residual
Stay 40 ppm；
(2) dichlorohydrin and normal heptane mixture separate to obtain dichlorohydrin 68.25g, the rate of recovery through 99 ± 1 DEG C of normal pressure distillations
97.5%, purity 99.5%；
(3) merge normal heptane totally 776 g of step (1) and (2) separation and recovery, the rate of recovery 97%, the n-hexane of recycling, which is recycled, to be made
With.
Embodiment 5
(1) 100 g hexamethylenes and 200 g dichlorohydrin hydrochloric acid solutions are added in three-necked flask, three-necked flask top successively connects
Rectifying column, condenser, water segregator and device for absorbing tail gas are connect, the filler of rectifying column is glass spring, and filler accumulation mode is scattered
Heap；Carrying out heating to three-necked flask by oil bath makes azeotropic system flow back, and temperature is about 70 DEG C, and the system azeotropic distillation time is
12 h, rectifying group lease making water segregator separate mass fraction be 23.26% 122 g of hydrochloric acid solution, the rate of recovery 93.85% is organic
10 ppm of dissolvent residual；
(2) dichlorohydrin and cyclohexane mixtures separate to obtain 57.89 g of dichlorohydrin, the rate of recovery through 82 ± 1 DEG C of normal pressure distillations
82.7%, purity 89.7%；
(3) merge hexamethylene totally 96 g of step (1) and (2) separation and recovery, the rate of recovery 96%, the hexamethylene of recycling, which is recycled, to be made
With.
The each component in above-described embodiment is analyzed using gas-chromatography (GC) method, test condition are as follows: OV-17 30m
× 0.32mm × 0.25 μm capillary chromatographic column；Post case temperature:, keeping 2 min, 25 DEG C/min of heating rate by 90 DEG C,
220 DEG C of final temperature, keep 5 min；Gasification temperature: 250 DEG C；Detector temperature: 250 DEG C；Carrier gas: 1.0 ml/min；It shunts:
60:1；Hydrogen: 30 ml/min；Air: 400 ml/min, 1 μ L of sample volume.
Claims (8)
1. a kind of method using alkanes entrainer separating dichloropropanol from dichlorohydrin hydrochloric acid solution, which is characterized in that
Using following steps:
(1) the alkanes entrainer of dichlorohydrin hydrochloric acid solution and azeotrope with water is placed in reaction kettle, reaction kettle is sequentially connected
Rectifier unit, condensing unit and division box；
(2) heating reaction kettle makes the solution azeotropy rectifying in reaction kettle, and rectifying component is transferred to division box by condensing unit
In, stratification, hydrochloric acid solution and alkanes entrainer separate；
(3) component that non-rectifying goes out in reaction kettle obtains dichlorohydrin through air-distillation.
2. the method according to claim 1, wherein the alkanes organic solvent of the azeotrope with water is hexamethylene
One of alkane, n-hexane and normal heptane.
3. the method according to claim 1, wherein dichlorohydrin hydrochloric acid solution as described in step (1) is sweet
Prepared by oily chloridising generates during epoxychloropropane, the mass ratio of dichlorohydrin and hydrochloric acid solution be 25 ~ 35:62 ~
78。
4. the method according to claim 1, wherein the alkane of azeotrope with water as described in step (1) is azeotrope-like
The mass ratio of agent and dichlorohydrin hydrochloric acid solution is 0.5 ~ 4:1.
5. according to the method described in claim 3, it is characterized in that, the alkane of azeotrope with water as described in step (1) is azeotrope-like
The mass ratio of agent and dichlorohydrin hydrochloric acid solution is 1 ~ 4:1.
6. the method according to claim 1, wherein the filler material in rectifier unit as described in step (1) is
One or more of Raschig ring, helical ring, ceramic ring, saddle type expectation, burnt fast, quartz, glass spring and insulation magnetic bead, filler is accumulated
Mode is to dissipate heap.
7. the method according to claim 1, wherein azeotropic distillation temperature described in step (2) is 62 ~ 70
DEG C, the azeotropic distillation time is 4 ~ 12 h.
8. the method according to claim 1, wherein air-distillation temperature described in step (3) is 70 ~ 100
℃。
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| CN201811218643.8A CN109134197B (en) | 2018-10-19 | 2018-10-19 | Method for separating dichloropropanol from dichloropropanol hydrochloric acid solution by using alkane entrainer |
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| CN201811218643.8A CN109134197B (en) | 2018-10-19 | 2018-10-19 | Method for separating dichloropropanol from dichloropropanol hydrochloric acid solution by using alkane entrainer |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111362778A (en) * | 2020-03-16 | 2020-07-03 | 山东凯泰科技股份有限公司 | Gas-phase desorption separation process of glycerol distillate |
| CN112645798A (en) * | 2020-12-10 | 2021-04-13 | 山东泰和水处理科技股份有限公司 | Method for separating dichloropropanol hydrochloric acid azeotropic liquid |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111362778A (en) * | 2020-03-16 | 2020-07-03 | 山东凯泰科技股份有限公司 | Gas-phase desorption separation process of glycerol distillate |
| CN111362778B (en) * | 2020-03-16 | 2022-04-15 | 山东凯泰科技股份有限公司 | Gas-phase desorption separation process of glycerol distillate |
| CN112645798A (en) * | 2020-12-10 | 2021-04-13 | 山东泰和水处理科技股份有限公司 | Method for separating dichloropropanol hydrochloric acid azeotropic liquid |
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