CN101462919A - Alkene separation method - Google Patents
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- CN101462919A CN101462919A CNA2007103001167A CN200710300116A CN101462919A CN 101462919 A CN101462919 A CN 101462919A CN A2007103001167 A CNA2007103001167 A CN A2007103001167A CN 200710300116 A CN200710300116 A CN 200710300116A CN 101462919 A CN101462919 A CN 101462919A
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Abstract
The invention relates to a method for separating olefinic hydrocarbon, in particular to a method for recycling olefinic hydrocarbon within the scope of detersive from feeding flow by adsorption. Sorbent and desorption agent which can recycle the olefinic hydrocarbon within a certain range of carbon number simultaneously according to different absorption and retention characteristics are selected.
Description
Technical field
The present invention relates to the separation of hydrocarbon materials.More specifically, the present invention relates to use the hydrocarbon of particular type as the method for desorbing agent with alkene and paraffinic hydrocarbons fractionation by adsorption.
Background technology
Alkene is the petrochemical industry intermediate of widespread use.Important chemical products is by forming with the olefinic polymerization of other chemical substance, oligomeric and alkylation.Often necessary is to want high relatively for effective technological reaction alkene purity, perhaps makes the formation of by product minimum.The most common ground must or be desirably the non-olefinic of alkene with for example paraffinic hydrocarbons to be separated at least.What often make us wishing is from comprising other type alkene, for example with the alkene that separates a kind of particular type in the mixture of branched-chain alkene, and for example positive alkene or alhpa olefin.
In the mixture of required alkene and chemical substance, can from this mixture, reclaim alkene by straight-forward fractional distillation with different relative volatilities.But,, separate and may difficulty maybe can not realize by distillation if alkene is present in the mixture that comprises one or more close different hydrocarbon of volatility.A general example like this appears at when paraffinic hydrocarbons or alkane mixture dehydrogenation are prepared alkene.Because this dehydrogenation reaction can not carried out fully because of equilibrium-limited, so dehydrogenation product is the homology mixture of very close paraffinic hydrocarbons of boiling point and alkene.Fractionation is infeasible usually under this situation, and utilizes the often effective separation method of the fractionation by adsorption that alkene is had a sorbent material optionally.
Fractionation by adsorption known in the art is from comprising linear alpha-olefin and another kind of hydrocarbon with close volatility, for example isolating the effective ways of linear alpha-olefin in the incoming mixture of paraffinic hydrocarbons that total molecular weight is identical or non-linear alkene.This method is described in J.A.Johnson, and S.Raghuram and P.R.Pujado are in the paper that is entitled as Olex:A Process for Producing High Purity Olefins that in August, 1987, american chemical IEEE provided in the meeting of Minnesota State Minneapolis country in summer.This paper has been described simulation moving-bed (SMB) adverse current adsorption separating method that is used to separate light normal olefine and similar paraffinic hydrocarbons.Be used to separate SMB similar of linear alpha-olefin but more detailed description is provided at the US3 that authorizes R.W.Neuzil etc., in 510,423.
Authorize the US5 of Beth McCulloch etc., 276,246 have described and have used low acidity silicon oxide molecular sieve, and the desorbing agent formed of silicite (silicalite) or ZSM molecular sieve and the naphthenic hydrocarbon that is replaced by alkyl substantially for example is from positive alkene be with fractionation by adsorption C the mixture of branched-chain alkene
5-C
8The method of positive alkene.
Authorize the US5 of B.V.Vora, 300,715 to have described paraffin conversion be the holistic approach of alkene.This method comprises fractionation by adsorption in paraffin dehydrogenation and the paraffin/olefin mixture that reclaims from the dehydrogenation zone ejecta is gone out alkene.This patent has been described and has been used for from paraffin/olefin mixture selectively removing aromatic hydrocarbons, makes molecular sieve inactivation used in the fractionation by adsorption of paraffin/olefin mixture and helps the zone of dehydrogenation to prevent aromatic hydrocarbons.
US6,106,702 disclose the adsorption separating method that is used to separate alkene and paraffinic hydrocarbons, wherein use the protection bed to remove the aromatic hydrocarbons pollutent in the incoming flow.Existing inside desorption agent flow is protected bed as flushing, and regenerates in the raffinate tower of this method.
Summary of the invention
Wide embodiment of the present invention is to be used for separating the adsorption separating method of purification agent with alkene from the incoming flow that comprises one or more alkene and other hydrocarbon materials, comprise incoming flow and adsorbent bed are contacted causing purification agent to be retained in olefine selective under the condition on the sorbent material, and reclaim the purification agent alkene that is kept from this sorbent material by this sorbent material is contacted with the desorbing agent that comprises one or more naphthenic hydrocarbon.
More particular embodiment is to be used for separating the adsorption separating method of purification agent with linear alpha-olefin from the incoming flow that comprises one or more alkene and other hydrocarbon materials, comprise making incoming flow cause purification agent under the condition on the sorbent material, to contact, and reclaim the purification agent linear alpha-olefin that is kept from this sorbent material by this sorbent material is contacted with the desorbing agent that comprises one or more naphthenic hydrocarbon with the linear alpha-olefin selective retention with adsorbent bed.
Another more particular embodiment is to be used for separating the simulated moving bed adsorption separation method of purification agent with alkene from the incoming flow that comprises one or more alkene and other hydrocarbon materials, comprise incoming flow and the adsorbent bed that comprises X type zeolite are contacted causing purification agent to be retained in olefine selective under the condition on the sorbent material, and reclaim the purification agent alkene that is kept from this sorbent material by this sorbent material is contacted with the desorbing agent that comprises one or more naphthenic hydrocarbon.
Description of drawings
Fig. 1 illustrates the meaning of measurement clean retention value (NRV) in comparing desorbing agent.
Fig. 2 comparison desorbing agent B and hexanaphthene desorbing agent are for comprising nC
14=with nC
14The pulse test result of charging.
Fig. 3 comparison desorbing agent B and hexanaphthene desorbing agent are for comprising nC
16=with nC
16The pulse test result of charging.
Embodiment
The containing olefin feed stream and can be derived from various in the source with the linear of suitable detergent range carbon chain lengths or band branched-chain alkene any of comprising of present method.Typical incoming flow is by being generated by the n-paraffin dehydrogenation that extraction obtains by the petroleum fractions of kerosene boiling range.Another may be originated is from the synthetic olefin stream that obtains of fischer-tropsch.The charging source is unrestricted in the present invention.
" the purification agent alkene " that comprises product of the present invention comprises C
9-C
20One or more alkene in the scope, promptly the alkene that has 9-20 carbon by each molecule is substantially formed.More typically, this carbon number is 9-16, often preferred 10-14, and the scope of 11-13 is fit to specific peace and quiet character.When product has at least 3 carbon, when preferred 4 or more more carbon number, when carbon number during at least 5, the present invention is with respect to the known technology particularly advantageous especially.C
8Lighter olefin(e) centent is generally less than 1.0wt%, typically less than 0.5wt%, preferably less than 0.1wt%.
The preferable use of this alkene is in the preparation of purification agent composition or precursor compound such as alkylbenzene (it can be converted into linear alkyl sulfonate LAS by neutralization subsequently then by sulfonated with sulphur trioxide or sulfuric acid).This product alkene can also be used in by known response and prepare other purification agent precursor or composition comprises in ethoxylate and the linear alcohol vitriol.If produce branched alkene, can pass through with toluene or alkylation of phenol, alkoxylate or sulfonated subsequently, perhaps by hydrogenation preparation (hydroformulation), carry out second step subsequently, for example the combination of alkoxylate, sulfation, phosphorylation, oxidation or these steps and they are converted into the cleaning product composition.
The hydrocarbon that is not recovered in the incoming flow can be the dissimilar alkene or the mixture of paraffinic hydrocarbons or alkene and paraffinic hydrocarbons; Other hydrocarbon materials, for example naphthenic hydrocarbon and aromatic substance also can exist.Therefore, present method can specifically be used for reclaiming positive alkene from the mixture that comprises isoolefine and/or paraffinic hydrocarbons.
Adsorptive separation technology consists essentially of and wherein makes sorbent material and the charging that contains alkene at the adsorption step that contacts under the adsorption conditions with wherein remove the desorption of the alkene that is adsorbed by selectivity on the sorbent material under desorption conditions.Fractionation by adsorption can utilize various technology to carry out, and for example uses two or more fixed beds and the shaking table operation of circulation adsorption step and regeneration step between them, the wherein sorbent material moving-bed operation of transporting between adsorption zone and desorption district, and as US2,985,589,3,510,423,3,720,604,3,723,302 and 3,755, simulation moving-bed (SMB) operation described in 153.For this separation preferred systems is adverse current simulation moving-bed (SMB) system.(SMB) circulation of inlet flow and output stream is advanced and can be finished by manifold system or by rotary disc valve (they are also known, and US3 for example is 040,777 and 3,422, shown in 848) in the operation.About the background instruction of SMB isolation technique, term and the description that wherein is applicable to the sorbent material of fractionation by adsorption, these patents are incorporated into this because of wherein.Although relevant for the description of this vote, wherein the way of contact of sorbent material and incoming flow is not the factor that the present invention will limit.
The simulated moving bed adsorption separating unit is simulated the countercurrent movement of sorbent material and incoming flow usually, but the simulation of sorbent material and incoming flow and stream motion are also known.The Adsorption of The Kirk-Othmer Encyclopediaof Chemical Technology, Liquid Separation has partly provided the detailed explanation about SMB technology.
Simulated moving bed technology generally includes at least 3 or 4 independent processes in sequence in isolated area, in a pile sorbent material of these isolated areas in remaining in one or more vertical cylinder adsorption chambers.In these districts each is sometimes referred to as son bed and constitutes usually by a plurality of adsorbent beds, and the bed number in each district is 2 or 3 to 8-10.The most commercial process unit of extensive practicality generally includes 24 beds.All these all are included in one or more this paper and are referred to as in the vertical container of adsorbent chamber.These beds separate each other on the structure by horizontal liquid collection/distribution network.Each net all is connected to the transfer line that defines transition point, this process flow for example incoming flow and raffinate stream enter or leave vertical adsorption chamber with extract stream.
Each term definition used herein is as follows." extract " is to be adsorbed a compound or the compounds that agent has more selective adsorption, the expression olefin product, and " extract remainder " is a compound or a compounds that is not quite adsorbed by selectivity.Term " desorbing agent " refers generally to can and be applicable to the material of desorption extract component from sorbent material.Term " extract stream " refer to wherein from adsorbent bed shift out by the materials flow of the extract of desorption material desorption.Term " raffinate stream " refers to wherein after the absorption of extract compound the materials flow of the raffinate component that shifts out from adsorbent bed.
The position that each included materials flow entered and left the chamber in this technology slowly transforms to another son bed along the length direction of adsorbent chamber from a son bed, enters or leave different son beds so that these materials flows are carried out along with operation cycle.Usually use at least 4 bursts of materials flows (incoming flow, desorption agent flow, extract stream and raffinate stream) in this process, and the position of incoming flow and desorbing agent inlet chamber and extract stream and raffinate stream leave the position of chamber in the same direction with predetermined space conversion simultaneously.Each increment transformation regularly of these transition point positions all can transmit or shift out liquid from indoor different absorption jizi for making dumplings bed.This conversion utilizes the dedicated pipeline of the per share materials flow of each son bed ingress to carry out.But this can obviously increase the cost of this technology, so these pipelines are reused usually.Usually only use a pipeline for each son bed, and the pipeline of each certain point in circulation carries a kind of in these 4 kinds of process flow.This simulation process also comprises usually uses the variable flow rate pump, and its liquid that will leave absorbent container one end is pushed the other end in the single continuous loop to.
Extract stream and raffinate stream generally are sent to tripping device, and normally separation column obtains reclaiming to the small part desorbing agent at this, and obtains extract product and extract remainder product.
Sorbent material used in present method is preferably by inorganic oxide, for example the molecular sieve that forms of silicon oxide and aluminum oxide; It is silico-aluminate.This material comprises known commercially available zeolite, for example zeolite Y and X zeolite.The crystallite sieve structure that many zeolites provide at this sorbent material to important aspect the selectivity of alkene.What term " molecular sieve " was intended to comprise wide region is fit to go bail for apron sorbent material and/or as the inorganic oxide of the sorbent material that is used to separate alkene, comprises the silicite material described in the above institute citing document.Silicite are very high molecular sieves of ratio of silicon oxide and aluminum oxide, because of it lacks ion-exchange capacity rather than zeolite.Silicite are described in more detail in US4, in 061,724,4,073,865 and 4,104,294.The inorganic oxide molecular sieve that can be used on another type in the sorbent material is a ZSM type zeolite, US3 for example, and 702,886 (ZSM-5), US3,832,449 (ZSM-12), US4,016,245 (ZSM-35) and US4, disclosed among 046,859 (ZSM-38).
The mixture that is used in preferred adsorbent in the disengaging zone and is tackiness agent by for example clay or aluminum oxide and X type or y-type zeolite extrudes or spraying drying forms the abrasion-proof particle that is of a size of 20-40 order (U.S.).This X type zeolite is described in US2, and in 822,244, this y-type zeolite is described in US3, in 130,007.These zeolites can ion-exchange, and self sodium is replaced with other positively charged ion that one or more are selected from basic metal and/or alkaline-earth metal.Preferred metals is drawn together lithium, potassium, calcium, strontium and barium.Can use two or more the combination in these metals.If it is there is the ion-exchange level in these materials, also preferably quite low.A kind of highly preferred sorbent material is a sodium type 13X zeolite.
An operational issue relevant with the fractionation by adsorption of alkene may be that some compound that exists in the incoming flow is deposited on the active sites of sorbent material.It happens frequently is attached to tightly on these positions for these compounds, so that the desorption process that is used for olefin recovery can't be removed them.Cause that along with piling up toxic action increases because of more objectionable impurities in the incoming flow, the ability drop of sorbent material, thereby the throughput of whole technology descends.The most common a kind of diolefine and the aromatic hydrocarbons of comprising that is run in present method.This area is recognized, prevents that objectionable impurities is used in the molecular sieve inactivation that separates alkene and makes us expecting, as US5, and 276,246,5,300,715 and 6,106, described in 702 shown in the method, and these patents are incorporated herein by reference.
Being used in desorption material in the liquid phase adsorption technology must be chosen as advisably and satisfy some standards.At first, desorption material should consequently not stop extracted component displacement desorption material and self can not be adsorbed so doughtily irrelevantly with the extracted component on the rational mass flow rate displacement sorbent material in sorption cycle subsequently.With regard to selectivity, it has more selectivity to desorption material with respect to the raffinate component to preferred adsorbent with respect to the raffinate ratio of component to all extracted components.Secondly, desorption material must be compatible with specific incoming mixture with particular adsorbent.More specifically, they must not can reduce or damage the ability of sorbent material or sorbent material to extracted component with respect to the raffinate components selection.In addition, desorption material should be unable to or cause that chemical reaction takes place for they with reaction on extracted component or the raffinate component chemical.The normal mixing from the void volume of sorbent material with desorption material of extract stream and raffinate circulation shifts out, and any the two chemical reaction of desorption material and extracted component or raffinate component or they that relates to all can make the product recovery complicated or stoped recovery.Desorbing agent also should separate with the raffinate component with extracted component easily, for example by fractionation.At last, desorption material should obtain easily, and cost is reasonable.
Reclaim the purification agent olefin product for being used in according to present method, desorbing agent comprises naphthenic hydrocarbon.Observed when reclaiming a series of alkene, these are particularly suitable for, and wherein selection rate is the function of olefin carbon number and hydrocarbon types, because close for the carbon number net retention volume of certain limit.Suitable naphthenic hydrocarbon comprise one or more can by fractionation easily with purification agent with olefin product isolating C
6-C
8The alkyl cyclopentane of scope and hexanaphthene.This desorbing agent should have the naphthene content of 90wt% at least.Preferred naphthenic hydrocarbon desorbing agent is made up of a kind of of alkyl cyclopentane and hexanaphthene or the two substantially, wherein preferred especially hexanaphthene.
Adsorption conditions generally comprises 20-250 ℃, and highly preferred 40-150 ℃, preferred 50-100 ℃ temperature range especially.Adsorption conditions also preferably includes is enough to make process fluid to keep the pressure of liquid phase, and it can arrive 4.5MPa for normal atmosphere.Desorption conditions generally comprises the temperature and pressure identical with the condition that is used to adsorb.In these scopes and near variation depend on the composition of sorbent material and charging.Embodiment:
" pulse test " process is used for the interchangeable desorbing agent of test under specific incoming mixture and Na type X zeolite adsorbents.Basic pulse test device is approximately 70cc by volume, and the tubular type adsorbent chamber that has entrance and exit at the two ends of chamber is formed.This chamber is included in the temperature-control device, and pressure control equipment is used for this chamber is remained under the constant predetermined pressure.Analytical equipment quantitatively and qualitatively, for example refractometer, polarimeter and chromatographic instrument can be connected to the outlet line of this chamber, and are used for one or more components that the discharging current of this adsorbent chamber is left in detection by quantitative and/or qualitative test.In the pulse test process, at first, desorption material balances each other by being loaded into sorbent material with specific desorption material by adsorbent chamber.Then inject the incoming mixture (being diluted in desorbing agent sometimes) of pulsatile once, and continue 1 or some minutes.Desorbing agent flows again again, and feed component as in the liquid-solid chromatography operation by wash-out.
Come these desorbing agents of comparison by measuring clean retention value (NRV), and can understand the meaning of NRV with reference to Fig. 1 of expression hypothesis pulse test.The charging of this hypothesis test comprises component A and B and the selected tracer agent that can not absorbed by positive research system.The peak of this tracer agent is set at 0 initial point on the volume scale, component A and B peak separately is labeled as each peak midpoint NRV on the volume scale.Because NRV is proportional at the partition ratio that adsorbs and be not adsorbed between the phase with component in theory, so can be by NRV than these 2 kinds of components selection rates of calculating.
Test result comprises 10% positive alkene, 85wt% n-paraffin and the positive C of 5wt% based on one group
18Raw material as tracer agent.Every pair of olefin/paraff iotan comprises identical carbon number, and for example positive nonene is right with positive nonane.Measure every pair net retention volume (NRV), and be expressed as the NRV olefin/paraff iotan.The various desorbing agents of being tested are:
A 80/20 normal heptane/1-octene
The MCP methylcyclopentane
The MCH methylcyclohexane
The CH hexanaphthene
Every couple NRV result is as follows under 125 ℃:
Desorbing agent:
A
B
MCP
MCH
CH
nC
9＝/nC
9 26.09/2.67 15.94/1.98 23.21/2.7 31.51/3.14 17.68/2.46
nC
10＝/nC
10 17.35/1.62 12.0/1.58 13.62/1.90
nC
12＝/nC
12 11.1/0.97 6.82/1.18 7.50/1.0
nC
14＝/nC
14 7.16/0.23 4.03/0.19 6.22/0.50
nC
16＝/nC
16 5.6/0.03 3.59/0.8 5.38/0.31 10.12/0.58 6.63/0.43
About being used to reclaim the suitable desorbing agent of this scope alkene, the conclusion below these results obtain:
Although desorbing agent A applicable to relate to single plant or among a small circle the charging of carbon number separate, impracticable for for example charging with wide region carbon number described herein because the NRV of different carbon number alkene variation too greatly.Desorbing agent A comprises suitable concentration C for processing
9The charging of alkene is not accepted especially, because its boiling point is near the boiling point of product, this makes and product can't be separated with desorbing agent.
Desorbing agent B is impracticable for the charging that comprises some higher carbon number, even NRV may represent that it is useful.For example, Fig. 2 shows nC
14=with nC
14The desorption peaks major part overlapping (with nC
14Concentration is divided by 10, so that it is on identical scale).Fig. 3 shows nC
16=with nC
16Even it is overlapping to a greater degree (with nC
16Concentration is divided by 10, so that it is on identical scale), this shows that it can not separate with this desorbing agent.Fig. 2 and 3 shows the comparison desorption peaks, shows that the hexanaphthene desorbing agent realized separating of each alkene and paraffinic hydrocarbons.
Thereby naphthenic hydrocarbon, particularly methylcyclopentane, methylcyclohexane and hexanaphthene are the suitable desorbing agents that separates detergent range alkene.When with the alkene of certain limit carbon number when incoming flow separates together, naphthenic hydrocarbon provides extra advantage.
Claims (9)
1. one kind is used for separating the adsorption separating method of purification agent with alkene from the incoming flow that comprises one or more alkene and other hydrocarbon materials, comprise described incoming flow and adsorbent bed are contacted causing purification agent to be retained in olefine selective under the condition on the described sorbent material, and reclaim the purification agent alkene that is kept from described sorbent material by described sorbent material is contacted with the desorbing agent that comprises one or more naphthenic hydrocarbon.
2. the method for claim 1, wherein said purification agent comprises C with alkene
9-C
20Alkene in the scope.
3. method as claimed in claim 1 or 2, wherein said purification agent with alkene substantially by C
9-C
20Linear alpha-olefin in the scope is formed.
4. method as claimed in claim 3, wherein said alkene have and are at least 3 carbon number range.
5. method as claimed in claim 1 or 2, wherein said sorbent material comprises molecular sieve.
6. method as claimed in claim 5, wherein said molecular sieve comprise X type zeolite.
7. method as claimed in claim 1 or 2, wherein said naphthenic hydrocarbon is made up of a kind of of hexanaphthene and methylcyclopentane or the two substantially.
8. method as claimed in claim 7, wherein said naphthenic hydrocarbon is made up of hexanaphthene substantially.
9. method as claimed in claim 1 or 2, wherein said adsorption separating method are the simulated moving bed adsorption separation methods.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105503498A (en) * | 2015-11-30 | 2016-04-20 | 中国海洋石油总公司 | Apparatus and process for acquiring high-purity durene from MTG heavy gasoline |
| CN111647423A (en) * | 2019-03-04 | 2020-09-11 | 内蒙古伊泰煤基新材料研究院有限公司 | Method for separating alpha-olefin by simulated moving bed |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1246271C (en) * | 2000-08-18 | 2006-03-22 | 环球油品公司 | Olefine separation method |
| US6670519B1 (en) * | 2001-10-15 | 2003-12-30 | Uop Llc | Monomethyl paraffin adsorptive separation process |
| AU2002232649A1 (en) * | 2001-12-18 | 2003-06-30 | Uop Llc | Adsorptive separation product recovery by fractional distillation |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105503498A (en) * | 2015-11-30 | 2016-04-20 | 中国海洋石油总公司 | Apparatus and process for acquiring high-purity durene from MTG heavy gasoline |
| CN111647423A (en) * | 2019-03-04 | 2020-09-11 | 内蒙古伊泰煤基新材料研究院有限公司 | Method for separating alpha-olefin by simulated moving bed |
| US11370732B2 (en) | 2019-03-04 | 2022-06-28 | Inner Mongolia Yitai Coal-Based New Materials Research Institute Co., Ltd. | Method of separating α-olefin by a simulated moving bed |
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Granted publication date: 20140528 Termination date: 20191217 |