CN108031144A - The method that extract and separate is carried out to the blend of organic matter and water using N-methylcyclohexylamine - Google Patents
The method that extract and separate is carried out to the blend of organic matter and water using N-methylcyclohexylamine Download PDFInfo
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- CN108031144A CN108031144A CN201711420108.6A CN201711420108A CN108031144A CN 108031144 A CN108031144 A CN 108031144A CN 201711420108 A CN201711420108 A CN 201711420108A CN 108031144 A CN108031144 A CN 108031144A
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- water
- organic matter
- methyl cyclohexylamine
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/04—Solvent extraction of solutions which are liquid
- B01D11/0492—Applications, solvents used
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/06—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/06—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
- C07D307/08—Preparation of tetrahydrofuran
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/12—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/12—1,4-Dioxanes; Hydrogenated 1,4-dioxanes not condensed with other rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses one kind to utilizeNThe method that methyl cyclohexylamine carries out extract and separate to the blend of organic matter and water, withNMethyl cyclohexylamine is extractant, willNMethyl cyclohexylamine is mixed with the blend of organic matter and water, is passed through CO2Reacted, after reaction, upper strata is the organic phase containing organic matter, lower floor for water andNThe water phase of methyl cyclohexylamine mixing composition, then by water andNMethyl cyclohexylamine mixing composition water phase rectifying, respectively obtain water andNMethyl cyclohexylamine.The present invention usesNMethyl cyclohexylamine is extractant, passes through CO2WithNMethyl cyclohexylamine reaction generationNSeparated after methyl cyclohexylamine bicarbonate with organic matter, to achieve the purpose that to separate organic matter, the upper strata after reaction is the organic phase containing organic matter, and the mass fraction of the organic matter in organic phase is up to 70~90%, after lower water phase rectifyingNMethyl cyclohexylamine reusable edible.
Description
Technical field
The present invention relates to organic matter and water separation technology field.
Background technology
It is that the common method of organic substance is recycled from product and aqueous solution to saltout with rectifying.But saltouing can produce largely
Salt-containing organic wastewater, and rectifying need to consume substantial amounts of energy and cause partial solvent volatilization loss and pollution environment.
The target of Green Chemistry is more more efficient than traditional chemical process, the few waste of development, the process and skill of few environmental pollution
Art, in 12 basic principles of Green Chemistry, one of which requires chemical process not have to solvent as far as possible, if can not keep away
Exempt from, also will be as far as possible with harmless solvent.If adding a kind of additive into water, make the ionic strength of the system in a big way
Interior to switch and control, this water containing additive can be recycled relatively easily.Such additive can substitute
Volatile solvent extracts organic matter from solution, and substitutes the inorganic salts in technique of saltouing at present, and solvent can at any time be recycled and followed
Ring utilizes, and greatly reduces energy consumption and the material consumption of production process, meets the direction of current green chemical industry development.And ion is strong
The discovery of degree intelligent switch solvent can solve the problems, such as this.
The content of the invention
It is an object of the invention to provide a kind of extracting process, is capable of green, efficiently extract and separate organic matter and water
Blend, and the method that can easily recycle extractant.
The technical scheme is that：
The method that blend of the present invention to organic matter and water carries out extract and separate, including：
WillN- methyl cyclohexylamine is mixed with the blend of organic matter and water, is passed through CO2Reacted, after reaction, upper strata is
Organic phase containing organic matter, lower floor for water andNThe water phase of-methyl cyclohexylamine mixing composition, then by water andN- methyl cyclohexylamine
Mix composition water phase rectifying, respectively obtain water andN- methyl cyclohexylamine.
Further, in the blend of organic matter and water, the volume ratio of water and organic matter is 0.1 ~ 4:1.
Further,NThe volume ratio of-methyl cyclohexylamine and the organic matter in the blend of organic matter and water is 1 ~ 2:1.
Further, organic matter can be 1,3- dioxolanes, Isosorbide-5-Nitrae-dioxane, tetrahydrofuran etc..
It is highly preferred that reaction of the present invention carries out under the temperature conditionss of the K of 283.15 K~303.15.Due to low temperature
Be conducive to extract, when the temperature is too low, consuming cost is excessive, and when temperature is excessive, extraction yield is low.
Compared with prior art, have the following advantages that：
（1）The present invention usesN- methyl cyclohexylamine is extractant, passes through CO2WithNThe reaction generation of-methyl cyclohexylamineN- methyl cyclohexane
Separated after amine-bicarbonate with organic matter, to achieve the purpose that to separate organic matter, the upper strata after reaction is having containing organic matter
Machine phase, the mass fraction of the organic matter in organic phase is up to 70~90%, after lower water phase rectifyingN- methyl cyclohexylamine is recycled
Utilize.
（2）The present invention can replace volatile organic solvent and current inorganic salts saltout the inorganic salts used in technique, behaviour
Make simply, it is less toxic, efficient, while extractant can be recycled by distillation operation, be the direction of green chemistry chemical technology development.
Embodiment
Embodiment 1：
（1）20mL water, 40mL are taken with graduated cylinder correct amountN- methyl cyclohexylamine, 20mL tetrahydrofurans.
（2）The solution measured is poured into the beaker of cleaning, and sealed with preservative film, be put into the thermostatted water of 283.1K
It is stand-by in bath.
（3）By high-purity CO2It is passed into beaker, takes upper solution and lower floor's solution to carry out gas-chromatography respectively every 0.5h
Analysis, until the composition no longer reacting condition of solution obtains upper solution and lower floor's solution respectively i.e. up to balance.
（4）Upper solution and each 1mL of lower floor's solution is taken to be placed in the volumetric flask of 25mL,N,NIn-dimethylacetylamide is used as
Thing is marked, is settled to 25mL, promoting the circulation of qi analysis of hplc of going forward side by side.
Analysis condition is as follows：Detector：Hydrogen flame ionization detector (fid detector)；Heater：493.15K；Sensing chamber
Temperature：523.15K；Post case initial temperature is 343.15K, with 20Kmin-1Speed be warming up to 493.15K；Carrier gas：Nitrogen；
H2Flow：60ml·min-1；Air mass flow：400ml·min-1；Tail wind drift amount：10ml·min-1；Dottle pin purge flow rate：
3ml·min-1；Split ratio：50:1.
（5）Learn that the mass fraction of tetrahydrofuran in upper organic phase is 84~90% by analysis.
Embodiment 2：
（1）20mL water, 40mL are taken with graduated cylinder correct amountN- methyl cyclohexylamine, 20mL 1,3- dioxolanes.
（2）The solution measured is poured into the beaker of cleaning, and sealed with preservative film, be put into the thermostatted water of 283.1K
It is stand-by in bath.
（3）By high-purity CO2It is passed into beaker, takes upper solution and lower floor's solution to carry out gas-chromatography respectively every 0.5h
Analysis, until the composition no longer reacting condition of solution obtains upper solution and lower floor's solution respectively i.e. up to balance.
（4）Upper solution and each 1ml of lower floor's solution is taken to be placed in the volumetric flask of 25ml,N,NIn-dimethylacetylamide is used as
Thing is marked, is settled to 25ml, promoting the circulation of qi analysis of hplc of going forward side by side.
Analysis condition is as follows：Detector：Hydrogen flame ionization detector (fid detector)；Heater：493.15K；Sensing chamber
Temperature：523.15K；Post case initial temperature is 343.15K, with 20Kmin-1Speed be warming up to 493.15K；Carrier gas：Nitrogen；
H2Flow:60ml· min-1；Air mass flow：400ml·min-1；Tail wind drift amount：10ml·min-1；Dottle pin purge flow rate：
3ml·min-1；Split ratio：50:1.
（5）Learn that the mass fraction of 1,3- dioxolanes in upper organic phase is 80~88% by analysis.
Embodiment 3：
（1）20mL water, 40mL are taken with graduated cylinder correct amountN- methyl cyclohexylamine, 20mL 1,4- dioxane.
（2）The solution measured is poured into the beaker of cleaning, and sealed with preservative film, be put into the thermostatted water of 283.1K
It is stand-by in bath.
（3）By high-purity CO2It is passed into beaker, takes upper solution and lower floor's solution to carry out gas-chromatography respectively every 0.5h
Analysis, until the composition no longer reacting condition of solution reaches balance, upper solution and lower floor's solution are obtained respectively.
（4）Upper solution and each 1ml of lower floor's solution is taken to be placed in the volumetric flask of 25ml,N,NIn-dimethylacetylamide is used as
Thing is marked, is settled to 25ml, promoting the circulation of qi analysis of hplc of going forward side by side.
Analysis condition is as follows：Detector：Hydrogen flame ionization detector (fid detector)；Heater：493.15K；Sensing chamber
Temperature：523.15K；Post case initial temperature is 343.15K, with 20Kmin-1Speed be warming up to 493.15K；Carrier gas：Nitrogen；
H2Flow:60ml·min-1；Air mass flow：400ml·min-1；Tail wind drift amount：10ml·min-1；Dottle pin purge flow rate：
3ml·min-1；Split ratio：50:1；
（5）Learn that the mass fraction of 1,4- dioxane in upper organic phase is 78~85% by analysis.
Embodiment 4：
（1）20mL water, 20mL are taken with graduated cylinder correct amountN- methyl cyclohexylamine, 20mL 1,4- dioxane.
（2）The solution measured is poured into the beaker of cleaning, and sealed with preservative film, be put into the thermostatted water of 283.1K
It is stand-by in bath.
（3）By high-purity CO2It is passed into beaker, takes upper solution and lower floor's solution to carry out gas-chromatography respectively every 0.5h
Analysis, until the composition no longer reacting condition of solution reaches balance, upper solution and lower floor's solution are obtained respectively.
（4）Upper solution and each 1ml of lower floor's solution is taken to be placed in the volumetric flask of 25ml,N,NIn-dimethylacetylamide is used as
Thing is marked, is settled to 25ml, promoting the circulation of qi analysis of hplc of going forward side by side.
Analysis condition is as follows：Detector：Hydrogen flame ionization detector (fid detector)；Heater：493.15K；Sensing chamber
Temperature：523.15K；Post case initial temperature is 343.15K, with 20Kmin-1Speed be warming up to 493.15K；Carrier gas：Nitrogen；
H2Flow:60ml·min-1；Air mass flow：400ml·min-1；Tail wind drift amount：10ml·min-1；Dottle pin purge flow rate：
3ml·min-1；Split ratio：50:1；
（5）Learn that the mass fraction of 1,4- dioxane in upper organic phase is 75~81% by analysis.
Embodiment 5：
（1）20mL water, 40mL are taken with graduated cylinder correct amountN- methyl cyclohexylamine, 10mL 1,4- dioxane.
（2）The solution measured is poured into the beaker of cleaning, and sealed with preservative film, be put into the thermostatted water of 283.1K
It is stand-by in bath.
（3）By high-purity CO2It is passed into beaker, takes upper solution and lower floor's solution to carry out gas-chromatography respectively every 0.5h
Analysis, until the composition no longer reacting condition of solution reaches balance, upper solution and lower floor's solution are obtained respectively.
（4）Upper solution and each 1ml of lower floor's solution is taken to be placed in the volumetric flask of 25ml,N,NIn-dimethylacetylamide is used as
Thing is marked, is settled to 25ml, promoting the circulation of qi analysis of hplc of going forward side by side.
Analysis condition is as follows：Detector：Hydrogen flame ionization detector (fid detector)；Heater：493.15K；Sensing chamber
Temperature：523.15K；Post case initial temperature is 343.15K, with 20Kmin-1Speed be warming up to 493.15K；Carrier gas：Nitrogen；
H2Flow:60ml·min-1；Air mass flow：400ml·min-1；Tail wind drift amount：10ml·min-1；Dottle pin purge flow rate：
3ml·min-1；Split ratio：50:1；
（5）Learn that the mass fraction of 1,4- dioxane in upper organic phase is 83~89% by analysis.
Embodiment 6：
（1）40mL water, 40mL are taken with graduated cylinder correct amountN- methyl cyclohexylamine, 10mL 1,4- dioxane.
（2）The solution measured is poured into the beaker of cleaning, and sealed with preservative film, be put into the thermostatted water of 283.1K
It is stand-by in bath.
（3）By high-purity CO2It is passed into beaker, takes upper solution and lower floor's solution to carry out gas-chromatography respectively every 0.5h
Analysis, until the composition no longer reacting condition of solution reaches balance, upper solution and lower floor's solution are obtained respectively.
（4）Upper solution and each 1ml of lower floor's solution is taken to be placed in the volumetric flask of 25ml,N,NIn-dimethylacetylamide is used as
Thing is marked, is settled to 25ml, promoting the circulation of qi analysis of hplc of going forward side by side.
Analysis condition is as follows：Detector：Hydrogen flame ionization detector (fid detector)；Heater：493.15K；Sensing chamber
Temperature：523.15K；Post case initial temperature is 343.15K, with 20Kmin-1Speed be warming up to 493.15K；Carrier gas：Nitrogen；
H2Flow:60ml·min-1；Air mass flow：400ml·min-1；Tail wind drift amount：10ml·min-1；Dottle pin purge flow rate：
3ml·min-1；Split ratio：50:1；
（5）Learn that the mass fraction of 1,4- dioxane in upper organic phase is 78~83% by analysis.
Embodiment 7：
（1）10mL water, 20mL are taken with graduated cylinder correct amountN- methyl cyclohexylamine, 90mL 1,4- dioxane.
（2）The solution measured is poured into the beaker of cleaning, and sealed with preservative film, be put into the thermostatted water of 283.1K
It is stand-by in bath.
（3）By high-purity CO2It is passed into beaker, takes upper solution and lower floor's solution to carry out gas-chromatography respectively every 0.5h
Analysis, until the composition no longer reacting condition of solution reaches balance, upper solution and lower floor's solution are obtained respectively.
（4）Upper solution and each 1ml of lower floor's solution is taken to be placed in the volumetric flask of 25ml,N,NIn-dimethylacetylamide is used as
Thing is marked, is settled to 25ml, promoting the circulation of qi analysis of hplc of going forward side by side.
Analysis condition is as follows：Detector：Hydrogen flame ionization detector (fid detector)；Heater：493.15K；Sensing chamber
Temperature：523.15K；Post case initial temperature is 343.15K, with 20Kmin-1Speed be warming up to 493.15K；Carrier gas：Nitrogen；
H2Flow:60ml·min-1；Air mass flow：400ml·min-1；Tail wind drift amount：10ml·min-1；Dottle pin purge flow rate：
3ml·min-1；Split ratio：50:1；
（5）Learn that the mass fraction of 1,4- dioxane in upper organic phase is 70~76% by analysis.
Rectifying will be carried out by each example gained lower floor solution above, specific method is as follows：
Solution is added in tower reactor, tower reactor heating, 95-110 DEG C of tower top temperature during distillation, 144-150 DEG C of bottom temperature,N- methyl
The yield of cyclohexylamine is more than 97%.
The present invention is passed through CO2Generate afterwardsN- methyl cyclohexylamine-bicarbonate solution can extract the organic matter in water outlet,
And withN- methyl cyclohexylamine-the increase of bicarbonate solution mass fraction and the increase of concentration, organic matter in organic phase
Mass fraction constantly increases.From application example, work as extractantNThe volume ratio of-methyl cyclohexylamine and water is 2:When 1, you can
Extract and separate is carried out well, obtains the organic matter more than 82%.Amine salting liquid extractant used by the process, has molten
The advantages that solution property is good, operating condition is gentle, steam forces down, structure can design.And environment is not polluted, be it is a kind of efficiently,
The extracting process of green, while extractant can recycle so that extraction cost is greatly lowered.
Claims (6)
1. the method that the blend of pair organic matter and water carries out extract and separate, it is characterised in that withN- methyl cyclohexylamine is extraction
Agent, willN- methyl cyclohexylamine is mixed with the blend of organic matter and water, is passed through CO2Reacted, after reaction, upper strata be containing
Have an organic phase of organic matter, lower floor for water andNThe water phase of-methyl cyclohexylamine mixing composition, then by water andN- methyl cyclohexylamine mixes
The water phase rectifying being combined into, respectively obtain water andN- methyl cyclohexylamine.
2. according to the method described in claim 1, it is characterized in that, in the blend of organic matter and water, the body of water and organic matter
Product is than being 0.1 ~ 4:1.
3. according to the method described in claim 1, it is characterized in that, it is characterised in that：N- methyl cyclohexylamine and organic matter and water
Blend in organic matter volume ratio be 1 ~ 2:1.
4. according to the method described in claim 1, it is characterized in that,NThe volume ratio of-methyl cyclohexylamine and water is 2:1.
5. according to the method described in claim 1, it is characterized in that, organic matter for 1,3- dioxolanes, Isosorbide-5-Nitrae-dioxane or
Tetrahydrofuran.
6. according to the method described in claim 1, it is characterized in that, the reaction the K of 283.15 K~303.15 temperature
Under the conditions of carry out.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711420108.6A CN108031144A (en) | 2017-12-25 | 2017-12-25 | The method that extract and separate is carried out to the blend of organic matter and water using N-methylcyclohexylamine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711420108.6A CN108031144A (en) | 2017-12-25 | 2017-12-25 | The method that extract and separate is carried out to the blend of organic matter and water using N-methylcyclohexylamine |
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| Publication Number | Publication Date |
|---|---|
| CN108031144A true CN108031144A (en) | 2018-05-15 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201711420108.6A Pending CN108031144A (en) | 2017-12-25 | 2017-12-25 | The method that extract and separate is carried out to the blend of organic matter and water using N-methylcyclohexylamine |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102892713A (en) * | 2010-02-10 | 2013-01-23 | 金斯顿女王大学 | Water with switchable ionic strength |
| CN106318619A (en) * | 2015-06-30 | 2017-01-11 | 财团法人工业技术研究院 | Method for extracting grease in algae |
-
2017
- 2017-12-25 CN CN201711420108.6A patent/CN108031144A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102892713A (en) * | 2010-02-10 | 2013-01-23 | 金斯顿女王大学 | Water with switchable ionic strength |
| CN106318619A (en) * | 2015-06-30 | 2017-01-11 | 财团法人工业技术研究院 | Method for extracting grease in algae |
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Application publication date: 20180515 |
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