CN107473957A - The method of chromium compound is enriched with from homogeneous organic liquid composition - Google Patents
The method of chromium compound is enriched with from homogeneous organic liquid composition Download PDFInfo
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- CN107473957A CN107473957A CN201710424827.9A CN201710424827A CN107473957A CN 107473957 A CN107473957 A CN 107473957A CN 201710424827 A CN201710424827 A CN 201710424827A CN 107473957 A CN107473957 A CN 107473957A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/02—Reverse osmosis; Hyperfiltration ; Nanofiltration
- B01D61/027—Nanofiltration
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Abstract
The present invention relates to a kind of method for being enriched with chromium compound from homogeneous organic liquid composition using NF membrane, methods described includes：(i) a kind of NF membrane selectively passed through is provided, (ii) by the way that the material liquid of the fluid composition is contacted with the NF membrane, to form penetrating fluid and trapped fluid.This method is carried out under stress, and the NF membrane is for the rejection of the chromium compound, the rejection higher than it for the organic compound.The method of the present invention can be realized, chromium compound is enriched in trapped fluid, and the chromium compound in penetrating fluid is controlled in relatively low concentration level.The method of the present invention can be used for, such as the recovery of chromium class homogeneous catalyst, and the processing of the organic liquid waste containing chromium.
Description
Technical field
The present invention relates to a kind of from homogeneous organic liquid composition chromium compound is enriched with using organic solvent nanofiltration film
Method.
Background technology
Membrane technology is a kind of relatively new technology for separate substance mixture.Its general principle is will be to be separated
Mixture of substances be added to film, the film has different permeabilities for single component present in mixture.This to treat
Each component present in the mixture of substances of separation passes through (penetrating) film with different speed, and therefore in film lateral condensation extremely
In various degree.Therefore separation standard is exactly permeability of the film for material to be separated.Driving force is mainly the pressure between film both sides
Power gradient, i.e., so-called transmembrane pressure Δ p.Alternatively, it is also possible to use other driving forces.
Here with membrane technology be not only according to different grain size select component mechanical grading act on, and including dissolve
And diffusion., therefore can also be by liquid because this film is worked in a manner of significantly more complicated than simple mechanical filter
Or gas separates each other.
In specific technical construction, mixture to be separated is delivered to the film with fed version.There, it is in film
Side be separated into trapped substance, be separated into penetrant in the opposite side of film.Penetrant and trapped substance are continuously discharged by film.Because point
From effect, the component for becoming enrichment in penetrant is those components that film has high permeability to it, and is received in trapped substance
The material of collection is film those components poor to its permeability.Because to the institute of mixture of substances in many membrane process using priciples
There is all permeable film of component-only there is different through-rates for each component, so in both trapped substance and penetrant
The all components of mixture of substances be present, simply concentration (mass fraction) is different.
Therefore, it is the permeability of characterization of membrane in membrane technology, film is determined the rejection R of the specific components of mixture of substances
Justice is as follows：
R=1-wP/wR
Wherein wPFor the mass fraction of the component in the penetrant of investigation, wRFor in the component in the film trapped substance of investigation
Mass fraction.Therefore rejection R can be 0 to 1 value, and therefore preferably provided with %.From the point of view of simple bicomponent system,
Such as 0% rejection then represents that the component of investigation is permeated as solvent just, it means that the matter of the component in trapped substance
It is identical with penetrant to measure fraction.On the other hand, the component that 100% rejection then represents to investigate is trapped completely.
On component to be separated, in addition to rejection, so-called membranous permeation rate is also to determine for characterizing its permeability
Property：
P=m'/(A* Δs p)
Wherein m' is the quality stream (mass stream) of penetrant, and A is membrane area, and Δ p is the transmembrane pressure applied.Ooze
Saturating rate is generally with units/kg/(h*m2* bar) represent.
Permeability P and rejection R is previously given by separation-active material of film, also by mixture of substances to be separated
Form previously given.When designing membrane separation process, these parameters are always related.Because the substance dependence of these parameters,
They are ensured by the selection of membrane material.Therefore, for specific separation task, the selectivity of separation-active membrane material
It is conclusive for whole technological design.
Principle so far with membrane technology reproduced below can be in Melin/Rautenbach：
Membranverfahren.Grundlagen der Modul-und Anlagenauslegung.[Membrane
Processes.Fundamentals of Module and System Design] Springer, Berlin Heidelberg
Consulted in 2004.
According to the parameter of material to be separated, the centrifugation used and driving force, different classes of film and/or UF membrane
Difference is generated between technique.Ultrafiltration, nanofiltration, gas infiltration and counter-infiltration are common classifications.These concepts are not equably
Use, but it is not also distinguish between clearly each other.When being discussed herein nanofiltration, it is contemplated that by means of film from least portion
The molecule that molal weight is more than 200g/mol is separated in the liquid substance mixture divided.Because this quasi-molecule has the 1nm orders of magnitude
Diameter, so using term nanofiltration or NF membrane.
According to primarily discrete aqueous substance mixture or primarily discrete organic substance mixture, the term used point
Wei not water-based nanofiltration or organophilic nanofiltration.Because the tolerance of membrane material and particularly they in aqueous medium or organic media
In swelling behavior channel syndrome make a clear distinction between right and wrong Chang Butong, so this difference is significant for membrane technology personnel.
The field that organophilic nanofiltration can be used is from the reactant mixture to be chemically reacted from homogeneous catalysis
Middle separating catalyst and/or its composition or catabolite.
Have that prior art discloses enriched in metals complex is urged from homogeneous liquid system using NF membrane
Agent, such as CN101360549A and CN105938518A, are hereby incorporated by reference herein.
Inventors investigated be enriched with chromium therein from homogeneous organic liquid composition using organic solvent nanofiltration film
The possibility of compound, so as to complete the present invention.
Being enriched with or remove chromium compound method therein in the current existing composition from organic liquid includes the precipitation method, inhales
Attached method and ion-exchange etc., the wherein precipitation method can introduce extra chemical substance, and absorption method and ion-exchange are less efficient,
Its processing for the chromium compound solution of low concentration is also undesirable, and adsorbent and regeneration of ion-exchange resin may also
Composition problem.
The content of the invention
Summary of the invention
The present invention provides a kind of method that chromium compound is enriched with from homogeneous fluid composition, and the fluid composition contains
Have, at least 50 weight % a kind of molecular weight based on its gross weight is no more than 1000g/mol organic compound, and the chromium
Compound, methods described comprise the following steps：
(i) a kind of NF membrane selectively passed through is provided, it has first surface and second surface,
(ii) by the way that the material liquid of the fluid composition is contacted with the first surface of the NF membrane, by the liquid
A part for body composition material liquid, from first surface transmembrane process to second surface, to form penetrating fluid and trapped fluid,
Wherein,
Pressure at first surface is more than the pressure at second surface, also,
The NF membrane is for the rejection of the chromium compound, the rejection higher than it for the organic compound.
Compared to existing method in the prior art, the present invention is a kind of alternative new method, and it has following excellent
Point：
(1) extra chemical substance need not be added；
(2) without carrying out regeneration treatment to used membrane material；
(3) energy consumption is low.
Meanwhile in the present invention, inventor it was unexpectedly observed that NF membrane for the rejection of chromium compound, can't be with
The increase of chromium compound concentration in material liquid and decline, but kept stable.In general, with being treated in material liquid point
From material concentration increase, film the rejection of the material can be declined (refer to yellow dimension chrysanthemum etc.,《Membrane separation technique outline》,
National Defense Industry Press, the 17th row of page 66).
The method of the present invention can be realized, chromium compound is enriched in trapped fluid, and the chromaking in penetrating fluid is closed
Thing is controlled in relatively low concentration level.The method of the present invention can be used for, such as the recovery of chromium class homogeneous catalyst, and containing chromium
The processing of organic liquid waste.
Detailed description of the invention
The organic compound can be selected from arene, fat hydrocarbon, ketone, glycols, esters, ethers, amine, nitrile
Class, aldehydes, phenols, amide-type, carboxylic acids, alcohols, furans, lactone and its mixture, preferably (methyl) esters of acrylic acid,
The monoesters or dibasic acid esters and its mixture of (methyl) acrylic acid of more preferably substituted or unsubstituted glycols.
Herein, term " (methyl) acrylate " refers to the mixing of acrylate or methacrylate or both
Thing.
In an embodiment of the invention, the organic compound is selected from (methyl) hydroxy-ethyl acrylate, (methyl)
Hydroxypropyl acrylate, ethylene glycol two (methyl) acrylate, (methyl) acrylate of propane diols two and its mixture.
The chromium compound can be selected from chromium (II) or chromium (III) salt and compound species, preferably Organic Chromium (II) or chromium
(III) the aliphatic carboxylic acid salt of salt, more preferably chromium (II) or chromium (III).
In an embodiment of the invention, the chromium compound is selected from the C of chromium (II) or chromium (III)1-C20Carboxylic acid
Salt, preferably 2 ethyl hexanoic acid chromium (III), sad chromium (III), 2,2,6,6- tetramethyl pimelic acid chromium (III), chromium naphthenate
(III), chromium acetate (III), chromium propionate (III), chromium butyrate (III), neopentanoic acid chromium (III), laurate chromium (III), stearic acid
It is chromium (III), chromium+oxalic acid (III), double (2 ethyl hexanoic acid) chromium (II), chromium acetate (II), chromium propionate (II), chromium butyrate (II), new
Valeric acid chromium (II), laurate chromium (II), chromium stearate (II), chromium+oxalic acid (II) and its mixture.
The NF membrane can have a 150-1,500g/mol molecular cut off, preferably 200-800g/mol, more preferably
200-600g/mol molecular cut off.
The NF membrane can include and be selected from following material：It is polyethylene, polypropylene, polytetrafluoroethylene (PTFE) (PTFE), poly- inclined
Difluoroethylene (PVDF), polysulfones, polyether sulfone, polyacrylonitrile, polyamide, polyimides, polyamidoimide, PEI,
Cellulose acetate, polyaniline, polypyrrole, polyether-ether-ketone (PEEK), polybenzimidazoles and its mixture, above-mentioned material can be handed over
It is connection or uncrosslinked.
The NF membrane can also be composite, and it includes carrier and the layer of thin alternative infiltration, preferably containing choosing
From the layer of the thin alternative infiltration of following material：Modified polyorganosiloxane based elastomeric, including dimethyl silicone polymer
(PDMS) based elastomeric, Ethylene-Propylene-Diene (EPDM) based elastomeric, polynorbornene based elastomeric, polycyclic octenyl elasticity
Body, polyurethane based elastomers, butadiene and nitrile rubber based elastomeric, natural rubber, butyl rubber based elastomers, polychlorostyrene fourth two
Alkene (Neoprene) based elastomeric, epichlorohydrin elastomer, polyacrylate elastomer, polyethylene, polypropylene, polytetrafluoroethyl-ne
Alkene (PTFE), polyvinylidene fluoride (PVDF) based elastomeric, polyether block amide (PEBAX), polyurethane elastomer, crosslinking are poly-
Ether, polyamide, polyaniline, polypyrrole and its mixture, particularly preferably include the thin alternative of polysiloxane based elastomers
The layer of infiltration.
The NF membrane can also include polymer film, and the polymer film has in powdery solid form by accounting for the polymerization
The organic or inorganic matrix disperseed existing for the amount for being up to about 20 weight % of thing film.
The NF membrane can also include the organic solvent nanofiltration film of organosilicon coating, be preferably based on polyimides or poly- third
The NF membrane of alkene nitrile.
In an embodiment of the invention,
(1) fluid composition contains at least 80 weight %, preferably 90 weight %, and the described of more preferably 95 weight % has
Machine compound, and/or
(2) molecular weight of the organic compound is no more than 800g/mol, preferably more than 500g/mol, does not surpass more preferably
Cross 200g/mol.
The method of the present invention can be carried out in following condition：
(1) temperature：- 30 DEG C to 100 DEG C, preferably -10 DEG C to 70 DEG C, more preferably 10 DEG C to 50 DEG C；
(2) transmembrane pressure：5bar to 70bar, preferably 20bar are to 60bar, more preferably 30bar to 50bar；And/or
(3) the chromium compound weight concentration in material liquid：No more than 100,000ppm, preferably more than 50,000ppm, more
Preferably more than 20,000ppm.
In an embodiment of the invention, at least a portion of the trapped fluid is recycled to the first table of the film
Face, preferably it is merged with material liquid, as long as the trapped fluid still keeps homogeneous.
In yet another embodiment of the present invention, when the chromium compound in the trapped fluid is enriched to certain concentration,
It is further handled to reduce the concentration of chromium compound therein, such as in the following manner：Absorption, precipitation, crystallization and/or
Ion exchange, the trapped fluid after the further processing is preferably recycled to the film first surface of film, more preferably by its with
Material liquid merges.
Brief description of the drawings
Fig. 1 is the schematic diagram of the diafiltration system of the embodiment of the present invention.
Embodiment
Embodiment
NF membrane
* styrene oligomer is as reference material
Fluid composition
Organic reaction waste liquid, it is mainly contained：
About 20-30% hydroxyethyl methacrylate,
About 20-30% hydroxy propyl methacrylate,
About 20-30% ethylene glycol dimethacrylate,
About 20-30% dimethacrylate, and
About 7000-8000ppm chromium acetate (III),
Gross weight based on the fluid composition.
Diafiltration system
Diafiltration system is as shown in Figure 1.First, a collection of pending organic reaction waste liquid is fed into tank 13.Pump 15 is used for allowing
Organic reaction waste liquid 14 and 16 is recycled to membrane module shell 17, and which provided the membrane module for separation.Pass through counterbalance valve 18
The driving force for separation is produced, the driving force provides the filter pressure for maintaining transmembrane pressure difference, and it allows the one of feed stream
Part is carried through the film and produces infiltration material flow 19 and retention material flow 20.Retention material flow 20 is returned into head tank
13, and it is recycled to membrane module shell 17.By this method, enrichment of the chromium acetate (III) in trapped substance is realized.
The detection method of chromium acetate (III) concentration
The type inductively coupled plasma matter of Optima 8000 that chromium acetate (III) concentration is produced using Perkin Elmer
Spectrometer is detected.First using dimethyl sulfoxide (DMSO) as solvent, the standard items that chromium acetate (III) concentration is 0.1-10ppm are prepared.
Then detected sample is diluted to 1-10ppm concentration with dimethyl sulfoxide (DMSO).Then standard items and the sample after dilution are sent into
In instrument, detect and calculate chromium acetate (III) concentration of sample.
Embodiment 1
At room temperature, the above-mentioned organic reaction waste liquids of 3L are added in head tank 13, the initial concentration of its chromium acetate (III) is
7869ppm.One is inserted in putamina 17Flux wound membranes (1.8 inches of diameter, 12 inches of length, effective film surface
0.1 square metre of product).Pressure is risen into 40bar by the flow speed stability of pump 15 in 150L/h, the slow counterbalance valve 18 that adjusts.Treat system
After stable, the concentration of chromium acetate (III) becomes in liquid, penetrating fluid 19 and trapped fluid 20 in not timing sampling and observation head tank 13
Change, and calculate rejection of the film to chromium acetate (III), now flux stabilized is in about 5LMH (L*m-2*h-1).It the results are shown in Table 1.
Table 1：The result of Flux films
Embodiment 2
At room temperature, the above-mentioned organic reaction waste liquids of 3L are added in head tank 13, the initial concentration of its chromium acetate (III) is
7961ppm.One is inserted in putamina 17280 wound membranes (1.8 inches of diameter, 12 inches of length, effective film surface
0.1 square metre of product).By the flow speed stability of pump 15 in 150L/h, counterbalance valve 18 is slowly adjusted by pressure to rising 40bar.Treat system
After stable, the concentration of chromium acetate (III) becomes in liquid, penetrating fluid 19 and trapped fluid 20 in not timing sampling and observation head tank 13
Change, and calculate rejection of the film to chromium acetate (III), now flux stabilized is in about 3LMH (L*m-2*h-1).It the results are shown in Table 2.
Table 2：The result of 280 films
From Examples 1 and 2 it is observed that enrichment of the chromium acetate (III) in trapped fluid 20.Meanwhile in embodiment
In system, trapped fluid 20 is recycled in head tank 13, so as to chromium acetate (III) in the liquid in head tank 13 concentration also therewith
Raise, reach about 3 times of initial concentration.When it flows through NF membrane, film is not observed to chromium acetate (III) rejection
Decline, rejection kept stable, also slightly improve in example 2.
Claims (13)
1. a kind of method that chromium compound is enriched with from homogeneous fluid composition, the fluid composition contains, total based on its
A kind of at least 50 weight % molecular weight of weight is no more than 1000g/mol organic compound, and the chromium compound, described
Method comprises the following steps：
(i) a kind of NF membrane selectively passed through is provided, it has first surface and second surface,
(ii) by the way that the material liquid of the fluid composition is contacted with the first surface of the NF membrane, by the liquid group
A part for compound material liquid, from first surface transmembrane process to second surface, to form penetrating fluid and trapped fluid,
Wherein,
Pressure at first surface is more than the pressure at second surface, also,
The NF membrane is for the rejection of the chromium compound, the rejection higher than it for the organic compound.
2. the method as described in claim 1, wherein the organic compound is selected from arene, fat hydrocarbon, ketone, glycol
Class, esters, ethers, amine, nitrile, aldehydes, phenols, amide-type, carboxylic acids, alcohols, furans, lactone and its mixture,
It is preferred that (methyl) esters of acrylic acid, the monoesters or dibasic acid esters of (methyl) acrylic acid of more preferably substituted or unsubstituted glycols and its
Mixture, particularly preferred (methyl) hydroxy-ethyl acrylate, (methyl) hydroxypropyl acrylate, ethylene glycol two (methyl) acrylate,
(methyl) acrylate of propane diols two and its mixture.
3. method as claimed in claim 1 or 2, wherein the chromium compound is selected from chromium (II) or chromium (III) salt and compound
Species, preferably Organic Chromium (II) or chromium (III) salt, more preferably the aliphatic carboxylic acid salt of chromium (II) or chromium (III).
4. the method as claimed in any one of the preceding claims, wherein the chromium compound is selected from the C of chromium (II) or chromium (III)1-
C20Carboxylate, preferably 2 ethyl hexanoic acid chromium (III), sad chromium (III), 2,2,6,6- tetramethyl pimelic acid chromium (III), aphthenic acids
Chromium (III), chromium acetate (III), chromium propionate (III), chromium butyrate (III), neopentanoic acid chromium (III), laurate chromium (III), tristearin
Sour chromium (III), chromium+oxalic acid (III), double (2 ethyl hexanoic acid) chromium (II), chromium acetate (II), chromium propionate (II), chromium butyrate (II),
Neopentanoic acid chromium (II), laurate chromium (II), chromium stearate (II), chromium+oxalic acid (II) and its mixture.
5. the method as claimed in any one of the preceding claims, wherein the NF membrane has 150-1,500g/mol, preferably
200-800g/mol, more preferably 200-600g/mol molecular cut off.
6. the method as claimed in any one of the preceding claims, wherein the NF membrane includes and is selected from following material：Polyethylene,
Polypropylene, polytetrafluoroethylene (PTFE) (PTFE), polyvinylidene fluoride (PVDF), polysulfones, polyether sulfone, polyacrylonitrile, polyamide, polyamides are sub-
Amine, polyamidoimide, PEI, cellulose acetate, polyaniline, polypyrrole, polyether-ether-ketone (PEEK), polybenzimidazoles
And its mixture.
7. the method as claimed in any one of the preceding claims, wherein the NF membrane is composite, it includes carrier and thin
Alternative infiltration layer, preferably contain the layer of the thin alternative infiltration selected from following material：Modified polyorganosiloxane base
Elastomer, including dimethyl silicone polymer (PDMS) based elastomeric, Ethylene-Propylene-Diene (EPDM) based elastomeric, poly- norborneol
Alkenyl elastomer, polycyclic octene based elastomeric, polyurethane based elastomers, butadiene and nitrile rubber based elastomeric, natural rubber,
Butyl rubber based elastomers, polychlorobutadiene (Neoprene) based elastomeric, epichlorohydrin elastomer, polyacrylate elastomer
Body, polyethylene, polypropylene, polytetrafluoroethylene (PTFE) (PTFE), polyvinylidene fluoride (PVDF) based elastomeric, polyether block amide
(PEBAX), polyurethane elastomer, crosslinked polyethers, polyamide, polyaniline, polypyrrole and its mixture, particularly preferably comprising poly- silicon
The layer of the thin alternative infiltration of oxyalkyl elastomer.
8. the method as claimed in any one of the preceding claims, wherein the NF membrane includes polymer film, polymer film tool
There is the organic or nothing disperseed in powdery solid form as existing for the amount for being up to about 20 weight % for accounting for the polymer film
Machine matrix.
9. the organic solvent that the method as claimed in any one of the preceding claims, wherein NF membrane includes organosilicon coating is received
Filter membrane, it is preferably based on the NF membrane of polyimides or polyacrylonitrile.
10. the method as claimed in any one of the preceding claims, wherein
(1) fluid composition contains at least 80 weight %, preferably 90 weight %, and the described of more preferably 95 weight % organises
Compound, and/or
(2) molecular weight of the organic compound is no more than 800g/mol, preferably more than 500g/mol, more preferably no more than
200g/mol。
11. the method as claimed in any one of the preceding claims, wherein methods described is carried out in following condition：
(1) temperature：- 30 DEG C to 100 DEG C, preferably -10 DEG C to 70 DEG C, more preferably 10 DEG C to 50 DEG C；
(2) transmembrane pressure：5bar to 70bar, preferably 20bar are to 60bar, more preferably 30bar to 50bar；And/or
(3) the chromium compound concentration in material liquid：No more than 100,000ppm weight, preferably more than 50,000ppm weight, more
Preferably more than 20,000ppm weight.
12. the method as claimed in any one of the preceding claims, wherein at least a portion of the trapped fluid is recycled to described
The first surface of film, preferably it is merged with material liquid, as long as the trapped fluid still keeps homogeneous.
13. method as claimed in claim 12, wherein when the chromium compound in the trapped fluid is enriched to certain concentration,
It is further handled to reduce the concentration of chromium compound therein, such as in the following manner：Absorption, precipitation, crystallization and/or
Ion exchange, the trapped fluid after the further processing is preferably recycled to the film first surface of film, more preferably by its with
Material liquid merges.
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| CN110449031A (en) * | 2019-07-15 | 2019-11-15 | 同济大学 | A kind of device and method separating organic liquid impurities |
| CN111450717A (en) * | 2020-04-24 | 2020-07-28 | 北京工业大学 | High-performance polymer organic solvent nanofiltration membrane and preparation method thereof |
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Application publication date: 20171215 |