CN114805005A - Method and device for separating 1-octene from Fischer-Tropsch synthesis oil-washed naphtha - Google Patents
Method and device for separating 1-octene from Fischer-Tropsch synthesis oil-washed naphtha Download PDFInfo
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- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 title claims abstract description 136
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 title claims abstract description 72
- 238000000034 method Methods 0.000 title claims abstract description 36
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 28
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 129
- 238000000605 extraction Methods 0.000 claims abstract description 50
- 238000006266 etherification reaction Methods 0.000 claims abstract description 23
- 238000006392 deoxygenation reaction Methods 0.000 claims description 20
- 238000000622 liquid--liquid extraction Methods 0.000 claims description 18
- 238000000638 solvent extraction Methods 0.000 claims description 18
- 239000003960 organic solvent Substances 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 238000010992 reflux Methods 0.000 claims description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Substances OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 15
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 12
- 150000001336 alkenes Chemical class 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 10
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- 230000003197 catalytic effect Effects 0.000 claims description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 8
- 229960004063 propylene glycol Drugs 0.000 claims description 6
- 235000013772 propylene glycol Nutrition 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 5
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 5
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 5
- 229940102253 isopropanolamine Drugs 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 239000011347 resin Substances 0.000 claims description 4
- 229920005989 resin Polymers 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 239000004711 α-olefin Substances 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 239000002245 particle Substances 0.000 claims description 2
- 238000000926 separation method Methods 0.000 abstract description 13
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract description 5
- 239000005977 Ethylene Substances 0.000 abstract description 5
- 238000007334 copolymerization reaction Methods 0.000 abstract description 4
- 238000000746 purification Methods 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 23
- 239000003921 oil Substances 0.000 description 9
- 239000011259 mixed solution Substances 0.000 description 8
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 description 4
- 238000004064 recycling Methods 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000003245 coal Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- -1 polyethylene Polymers 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000007670 refining Methods 0.000 description 3
- 230000001172 regenerating effect Effects 0.000 description 3
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- RCBGGJURENJHKV-UHFFFAOYSA-N 2-methylhept-1-ene Chemical compound CCCCCC(C)=C RCBGGJURENJHKV-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000010907 mechanical stirring Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- JVSWJIKNEAIKJW-UHFFFAOYSA-N 2-Methylheptane Chemical compound CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000010689 synthetic lubricating oil Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/04—Purification; Separation; Use of additives by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/10—Purification; Separation; Use of additives by extraction, i.e. purification or separation of liquid hydrocarbons with the aid of liquids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/14875—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with organic compounds
- C07C7/14891—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with organic compounds alcohols
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method and a device for separating 1-octene from Fischer-Tropsch synthesis oil-washed naphtha. The method comprises the following steps: (1) rectifying Fischer-Tropsch synthesis oil-washed naphtha to obtain C8 narrow fraction; (2) performing first-stage extraction deoxidation on the C8 narrow fraction to obtain a deoxidation product with the oxide content of 0.7-0.9 wt%; then, performing secondary extraction deoxidation on the deoxidation product to obtain deoxidation C8 narrow fraction with the oxide content of not more than 0.01 wt%; (3) carrying out methanol etherification reaction on the deoxidized C8 narrow fraction to obtain an etherified C8 narrow fraction; (4) and (3) carrying out light component removal rectification on the etherified C8 narrow fraction, and then carrying out precise rectification on heavy components in a tower bottom obtained by the light component removal rectification to obtain the 1-octene. The method has the advantages of simple operation, high separation efficiency, low cost and the like, and the 1-octene product obtained by separation and purification has high purity and can meet the requirement of ethylene copolymerization.
Description
Technical Field
The invention relates to the technical field of producing high-purity olefin from coal-based raw materials, in particular to a method and a device for separating 1-octene from Fischer-Tropsch synthesis oil-washed naphtha.
Background
The Fischer-Tropsch synthesis oil-washed naphtha is a coal chemical product rich in alpha-olefin, particularly the product rich in 1-octene can be widely used in the production of ethylene comonomer, brominated alkane, high-carbon alcohol, synthetic lubricating oil and the like, and has higher economic value. However, when fischer-tropsch olefins are developed from fischer-tropsch synthesis naphtha, the oils contain oxygen-containing compounds such as alcohols, aldehydes, acids, esters, etc. besides alkanes and olefins, which seriously affect the downstream production, especially the processing production in the high-end polyethylene industry.
The currently reported combined process route of 'alkaline washing-etherification-rectification-extractive distillation' developed by SASOL corporation in south Africa realizes the preparation of polymerization-grade 1-hexene and 1-octene, but the process has the defects of high complexity, high energy consumption and high operation cost.
The 1-octene separation technology provided by CN103360195A adopts a method of pre-separation, azeotropic rectification deoxidation, fine separation and de-heavy-refining treatment, and the process has the defects of large solvent consumption, complex operation, high energy consumption and the like in an azeotropic deoxidation link, and partial impurities of a de-heavy 1-octene crude product are difficult to remove.
Disclosure of Invention
The invention aims to solve the problems of complex removal process of oxygen-containing compounds, high cost, low product purity and the like in the prior art, and provides a method and a device for separating 1-octene from Fischer-Tropsch synthesis oil-washed naphtha.
In order to achieve the above objects, the present invention provides, in one aspect, a method for separating 1-octene from Fischer-Tropsch synthetic naphtha, the method comprising the steps of:
(1) rectifying Fischer-Tropsch synthesis oil-washed naphtha to obtain C8 narrow fraction;
(2) performing first-stage extraction deoxidation on the C8 narrow fraction to obtain a deoxidation product with the oxide content of 0.7-0.9 wt%; then, performing secondary extraction deoxidation on the deoxidation product to obtain deoxidation C8 narrow fraction with the oxide content of not more than 0.01 wt%;
(3) carrying out methanol etherification reaction on the deoxidized C8 narrow fraction to obtain an etherified C8 narrow fraction;
(4) and (3) carrying out light component removal rectification on the etherified C8 narrow fraction, and then carrying out precise rectification on heavy components in a tower bottom obtained by the light component removal rectification to obtain the 1-octene.
The invention provides a device for separating 1-octene from Fischer-Tropsch synthetic oil washed naphtha, which comprises a first rectifying tower, a second rectifying tower, a first counter-current liquid-liquid extraction deoxygenation tower, a second counter-current liquid-liquid extraction deoxygenation tower, methanol etherification reaction equipment, a light component removal rectifying tower and a precision rectifying tower which are sequentially communicated.
Through the technical scheme, the beneficial technical effects obtained by the invention are as follows:
the method comprises the steps of pretreating Fischer-Tropsch synthesis oil-washed naphtha before separating and purifying 1-octene, removing oxygen-containing compounds through extraction, rectification, chemical reaction and other operations, pre-cutting a single carbon component, precisely rectifying and separating a 1-octene crude product, and refining the crude product to obtain a high-quality 1-octene product. The method has the advantages of simple operation, high separation efficiency, low cost and the like, and the 1-octene product obtained by separation and purification has high purity and can meet the requirement of ethylene copolymerization.
The invention adopts the liquid-liquid extraction deoxidation technology, can effectively remove oxides in the raw materials, and can synchronously deacidify and deoxidize, so that the olefin loss rate is lower; the method is characterized in that part of isomeric olefin of 1-octene is removed by methanol etherification, and the separation of 1-octene, n-octane and octene isomers can be completed by precision rectification without adding any solvent. The method can separate the 1-octene product with high added value from the Fischer-Tropsch synthesis naphtha washing oil in a simple and efficient way, and is beneficial to the development of the 1-octene production process.
Drawings
FIG. 1 is a schematic process flow diagram of the separation of 1-octene from Fischer-Tropsch synthesis oil washed naphtha according to one embodiment of the present invention.
Detailed Description
The following detailed description of embodiments of the invention refers to the accompanying drawings. It should be understood that the detailed description and specific examples, while indicating the present invention, are given by way of illustration and explanation only, not limitation.
In a first aspect, the invention provides a process for separating 1-octene from Fischer-Tropsch synthesis oil washed naphtha, the process comprising the steps of:
(1) rectifying Fischer-Tropsch synthesis oil-washed naphtha to obtain C8 narrow fraction;
(2) performing first-stage extraction deoxidation on the C8 narrow fraction obtained in the step (1) to obtain a deoxidation product with the oxide content of 0.7-0.9 wt%; then, performing secondary extraction deoxidation on the deoxidation product to obtain deoxidation C8 narrow fraction with the oxide content of not more than 0.01 wt%;
(3) carrying out methanol etherification reaction on the deoxidized C8 narrow fraction obtained in the step (2) to obtain an etherified C8 narrow fraction;
(4) and (4) performing light component removal rectification on the etherified C8 narrow fraction obtained in the step (3), and then performing precise rectification on the heavy component in the tower bottom obtained by the light component removal rectification to obtain the 1-octene.
The method comprises the steps of pretreating Fischer-Tropsch synthesis oil-washed naphtha before separating and purifying 1-octene, removing oxygen-containing compounds through extraction, rectification, chemical reaction and other operations, pre-cutting a single carbon component, precisely rectifying and separating a 1-octene crude product, and refining the crude product to obtain a high-quality 1-octene product. The method has the advantages of simple operation, high separation efficiency, low cost and the like, and the 1-octene product obtained by separation and purification has high purity and can meet the requirement of ethylene copolymerization.
In some embodiments, the Fischer-Tropsch naphtha comprises C5 to C12 paraffins and C5 to C12 olefins, wherein alpha olefins comprise 55 to 60 wt%, normal paraffins comprise 25 to 30 wt%, beta olefins comprise 5 to 10 wt%, oxygenates comprise 2 to 3 wt%, and small amounts of isoolefins.
In some embodiments, in step (1), the rectifying comprises a first rectifying and a second rectifying, and the light components of C7 and below in the fischer-tropsch synthesis oil washed naphtha are removed by the first rectifying to obtain heavy components of C8 and above; removing heavy components of C9 and above in the C8 and above recombination through the second rectification to obtain a C8 narrow fraction.
Specifically, the first rectification is carried out in a first rectification tower, the theoretical plate number of the first rectification tower is 40, the plate number of a rectification section is 18, the plate number of a stripping section is 22, the reflux ratio is 5, and the operating pressure is normal pressure; the Fischer-Tropsch synthesis oil-washed naphtha enters the first rectifying tower from the 19 th tray, light components C7 and the following components are obtained from the top of the tower, the extraction rate is 0.38-0.44, the content of C8 in the light components is less than 1 wt%, heavy components C8 and the above components are obtained from the bottom of the tower, and the content of C7 and the following components in the heavy components is less than 1 wt%.
The second rectification is carried out in a second rectification tower, the theoretical plate number of the second rectification tower is 40, the plate number of a rectification section is 23, the plate number of a stripping section is 17, the reflux ratio is 5, and the operating pressure is normal pressure; adding heavy components in the tower bottom obtained from the first rectifying tower into the second rectifying tower from a 24 th tower plate, and obtaining a C8 narrow fraction from the tower top, wherein the extraction rate is 0.5-0.57, and the content of C7 and the following components is less than 3 wt%; obtaining components with the weight of more than C8 from the bottom of the tower, wherein the content of the C8 component is less than 2 wt%.
In some preferred embodiments, the C8 narrow fraction has a C8 component content of greater than 97 wt% and an oxide content of 2.2 to 2.8 wt%.
In some embodiments, in step (2), the first-stage extractive deoxygenation is countercurrent liquid-liquid extractive deoxygenation, and the temperature of the first-stage extractive deoxygenation is 15-40 ℃ for 10-15 min.
In some preferred embodiments, the first-stage extraction deoxidation adopts a first extracting agent, and the first extracting agent is a compound solvent of an alcohol organic solvent and an amine organic solvent in a volume ratio of 1:1-2: 1.
In some preferred embodiments, the alcoholic organic solvent is at least one of 1, 4-butanediol, 1, 2-propanediol, ethylene glycol, and methanol.
In some preferred embodiments, preferably, the amine-based organic solvent is at least one of N, N-dimethylformamide, ethanolamine, diethanolamine, and isopropanolamine.
In some preferred embodiments, the volumetric flow ratio of the first extractant to the C8 narrow fraction is from 2:1 to 4: 1.
The density of the C8 narrow fraction was 0.72g/cm 3 In order to ensure the extraction, the density of the first extractant is higher than that of the C8 narrow fraction, and in order to improve the extraction efficiency, the density of the first extractant is higher than 1g/cm 3 。
In some preferred embodiments, the first extractant has a density of 1.07 to 1.13g/cm 3 ；
In step (2) of the present invention, after the first-stage extraction deoxidation, the oxide content in the narrow fraction of C8 is 0.7-0.9 wt%.
In some embodiments, in step (2), the secondary extractive deoxygenation is countercurrent liquid-liquid extractive deoxygenation, and the temperature of the secondary extractive deoxygenation is 15-40 ℃ for 10-15 min.
In some preferred embodiments, the second-stage extraction deoxidation adopts a second extracting agent, and the second extracting agent is a compound solvent of an alcohol organic solvent and an amine organic solvent in a volume ratio of 1:1-2: 1.
In some preferred embodiments, the alcoholic organic solvent is at least one of 1, 4-butanediol, 1, 2-propanediol, ethylene glycol, and methanol.
In some preferred embodiments, preferably, the amine-based organic solvent is at least one of N, N-dimethylformamide, ethanolamine, diethanolamine, and isopropanolamine.
In some preferred embodiments, the volumetric flow ratio of the second extractant to the C8 narrow fraction is from 2:1 to 4: 1.
The density of the C8 narrow fraction was 0.72g/cm 3 The density of the second extractant is higher than that of the narrow C8 fraction to ensure the extraction, and the density of the second extractant is higher than 1g/cm to raise the extraction efficiency 3 。
In some preferred embodiments, the second extractant has a density of 1.07 to 1.13g/cm 3 。
In the invention, the first-stage extraction deoxidation and the second-stage extraction have no necessary connection, and the same extractant or different extractants can be used. In order to simplify the preparation process of the extractant, the same extractant is preferably used for the first-stage extraction deoxidation and the second-stage extraction deoxidation, and in order to save the use amount of the extractant, the extractant after the second-stage extraction deoxidation can be used for the first-stage extraction deoxidation.
In some preferred embodiments, the second extractant is used as the extractant for the primary extraction deoxidation when the oxide content is below 0.01% after the second extractant is used for the secondary extraction deoxidation.
In the step (2) of the invention, after the two-stage extraction deoxidation, the oxide content in the C8 narrow fraction is below 0.01 wt%.
In some embodiments, in step (3), the methanol is etherified at a temperature of 80 to 90 ℃ for 1.5 to 2.0 h.
In some preferred embodiments, the methanol etherification reaction has a mass ratio of methanol to the deoxygenated C8 narrow fraction of 0.2:1 to 0.3: 1.
In some preferred embodiments, the catalyst for the methanol etherification reaction is a large-particle acidic resin catalyst, and any acidic resin that can provide protonic acid may be used as the catalyst of the present invention. For example, macroporous strongly acidic cationic resins.
In the process of the methanol etherification, in order to ensure that the solution in the reactor flows and can fully contact with the catalyst, a stirring paddle is additionally arranged at the bottom of the reactor to continuously stir at the rotating speed of 50-100 r/min. And because the methanol and the C8 narrow fraction have poor solvent property, a condensation reflux device is required to be additionally arranged at the top of the reactor to recover the methanol, and corresponding methanol is supplemented from the bottom of the reactor to maintain the reaction.
In the step (3) of the invention, the methanol etherification reaction mainly removes part of methyl heptene, especially 2-methyl-1-heptene, which affects the purity of the 1-octene product in the narrow fraction C8, and generates corresponding methyl ether substances, and the boiling point is correspondingly improved by 20-30 ℃.
In some embodiments, in step (4), the light ends removal rectification is performed in a light ends removal rectification column having a theoretical plate number of 135, a rectification section plate number of 55, a stripping section plate number of 80, a reflux ratio of 40, and an operating pressure of normal pressure; and (3) adding the etherified C8 narrow fraction obtained in the step (3) into the light component removal rectifying tower from a 56 th tower plate, wherein light components obtained from the tower top are substances with the boiling point of 1-octene below, such as methyl heptene, methyl heptane, methanol and the like, the tower top yield is 0.08-0.1, the content of 1-octene in the light components is less than 65 wt%, and the content of 1-octene in the heavy components obtained from the tower bottom is more than 58 wt%.
In some embodiments, in step (4), the precision rectification is performed in a precision rectification column having a theoretical plate number of 140, a rectification section plate number of 76, a stripping section plate number of 64, a reflux ratio of 40, and an operating pressure of normal pressure; and the heavy component in the tower bottom of the light component removal rectifying tower is added into the precise rectifying tower from the 77 th tower plate, the purity of 1-octene in the light component obtained from the tower top is more than 97 wt%, the distillation rate at the tower top is 0.57-0.60, and the content of 1-octene in the heavy component obtained from the tower bottom is less than 1 wt%.
In the invention, the purity of the 1-octene product is more than 97 wt%, and the yield of the 1-octene product is more than 87 wt%.
The invention adopts the liquid-liquid extraction deoxidation technology, can effectively remove oxides in the raw materials, and can synchronously deacidify and deoxidize, so that the olefin loss rate is lower; the method is characterized in that part of isomeric olefin of 1-octene is removed by methanol etherification, and the separation of 1-octene, n-octane and octene isomers can be completed by precision rectification without adding any solvent. The method can separate the 1-octene product with high added value from the Fischer-Tropsch synthesis naphtha washing oil in a simple and efficient way, and is beneficial to the development of the 1-octene production process.
The second aspect of the invention provides a device for separating 1-octene from Fischer-Tropsch synthetic oil washed naphtha, which comprises a first rectifying tower A, a second rectifying tower B, a first countercurrent liquid-liquid extraction deoxygenation tower C, a second countercurrent liquid-liquid extraction deoxygenation tower D, methanol etherification reaction equipment E, a light component removal rectifying tower F and a precise rectifying tower G which are sequentially communicated, as shown in figure 1.
In some embodiments, the first rectification column a has a theoretical plate number of 40, a rectification section plate number of 18, a stripping section plate number of 22, and a feed plate number of 19.
In some embodiments, the theoretical plate number of the second rectification column B is 40, the rectification section plate number is 23, the stripping section plate number is 17, and the feed plate number is 24.
In some embodiments, the first countercurrent liquid-liquid extraction deoxygenator column C and the second countercurrent liquid-liquid extraction deoxygenator column D employ a sieve tray column or a packed column to achieve sufficient contact between the two phases.
In some embodiments, the methanol etherification reaction equipment E is a fixed bed catalytic reactor, and the inside of the fixed bed catalytic reactor is provided with a catalyst bed layer, the bottom of the fixed bed catalytic reactor is provided with a stirring paddle, and the top of the fixed bed catalytic reactor is provided with a condensation reflux part.
In some embodiments, the light ends removal rectification column F has a theoretical plate number of 135, a rectification section plate number of 55, a stripping section plate number of 80, and a feed plate number of 56.
In some embodiments, the precision rectification column G has a theoretical plate number of 140, a rectification section plate number of 76, a stripping section plate number of 64, and a feed plate number of 77.
The method of the first aspect and the device of the second aspect are adopted to separate 1-octene from Fischer-Tropsch synthesis oil naphtha, which is described in conjunction with FIG. 1, and specifically comprise the following steps:
(1) pretreatment: sending Fischer-Tropsch synthesis oil-washed naphtha (stream 1) into a first rectifying tower A with the theoretical plate number of 40, carrying out first rectification, obtaining C7 and the following components (stream 2) from the top of the tower, and obtaining C8 and the above components (stream 3) from the bottom of the tower; then, feeding the C8 and the above components (stream 3) into a second rectifying tower B with the theoretical plate number of 40, performing second rectification, obtaining 98 wt% of the C8 component (stream 5) at the tower top, and obtaining C9 and the above components (stream 4) from residual liquid at the tower bottom;
(2) countercurrent extraction: sending the C8 component (stream 5) obtained in the step (1) into a first countercurrent liquid-liquid extraction deoxygenation tower C for primary extraction deoxygenation, then sending the stream (stream 7) subjected to the primary extraction deoxygenation into a second countercurrent liquid-liquid extraction deoxygenation tower D for secondary extraction deoxygenation; the extraction agent is a compound solvent (stream 6) of alcohols and amine organic solvents according to a ratio of 1:1, wherein the alcohol reagent is composed of at least one solvent of 1, 4-butanediol, 1, 2-propanediol, ethylene glycol and methanol, and the amine reagent is composed of at least one solvent of N, N-dimethylformamide, ethanolamine, diethanolamine and isopropanolamine; the ratio of extractant flow to C8 component (stream 5) flow was 1: 1; collecting and regenerating the extract (stream 8) for recycling;
(3) methanol etherification: after two-stage countercurrent contact, feeding the deacidified and deoxidized C8 component (stream 9) and methanol (stream 10) into methanol etherification equipment E according to the mass ratio of 1:2, and performing methanol etherification reaction under the conditions that the solution temperature is 90 ℃ and the mechanical stirring is carried out for 30r/min to remove partial impurities;
(4) light component removal: after the methanol etherification reaction is carried out for 30min, the mixed solution (stream 11) of methanol and deacidification and deoxidation C8 is sent into a light component removal tower F with the theoretical plate number of 135, the mixed solution (stream 11) is subjected to light component removal treatment, a heavy component C8 mixed solution (stream 13) is obtained at the tower bottom, and the unreacted methanol solution (stream 12) obtained at the tower top is recycled;
(5) precision rectification: and (3) sending the heavy component C8 mixed solution (stream 13) obtained from the bottom of the tower into a precise rectifying tower G with the theoretical plate number of 140, precisely rectifying the C8 mixed solution (stream 13), wherein the reflux ratio is 5, feeding is carried out from a 40 th plate, the purity of a 1-octene product (stream 14) obtained from the top of the tower is 98.3 wt%, and the residual liquid at the bottom of the tower is a small amount of mixed solution (stream 15) of 1-octene, n-octane, isomeric octene, internal olefin, C8 etherate and the like.
In order to further understand the present invention, the technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Unless otherwise specified, the reagents involved in the examples of the present invention are all commercially available products, and all of them are commercially available. The present invention will be described in detail below by way of examples.
In the following examples, fischer-tropsch synthesis oil-washed naphtha was produced from 400-million ton/year coal-to-liquids projects from Ningxia coal industries, consisting of: C5-C12 alkane and olefin components, wherein alpha-olefin accounts for 55-60%, normal alkane accounts for 25-30%, beta-olefin accounts for 5-10%, oxygen-containing compound accounts for 2-3%, and a small amount of isoolefin.
Examples
A method for separating 1-octene from Fischer-Tropsch synthesis naphtha is described with reference to FIG. 1, and specifically comprises the following steps:
(1) sending Fischer-Tropsch synthesis oil-washed naphtha (stream 1) into a first rectifying tower A from a 19 th tray, wherein the number of theoretical plates is 40, the number of plates in a rectifying section is 18, the number of plates in a stripping section is 22, the reflux ratio is 5, the operating pressure is normal pressure, performing first rectification, obtaining light components (stream 2) of C7 and below from the top of the tower, the extraction rate is 0.44, and the content of C8 in the light components at the top of the tower is less than 1 wt%; obtaining heavy components (stream 3) of C8 and above from the bottom of the tower, wherein the content of C7 and the following components in the heavy components at the bottom of the tower is less than 1 wt%;
(2) feeding the C8 and the heavy components (stream 3) obtained in the step (1) into a second rectifying tower B from a 24 th tower plate, wherein the number of theoretical plates is 40, the number of rectifying section tower plates is 23, the number of stripping section tower plates is 17, the reflux ratio is 5, the operating pressure is normal pressure, performing second rectification, obtaining a C8 narrow fraction (stream 5) from the top of the tower, the recovery rate is 0.57, and the content of the C8 component is more than 97 wt%; obtaining heavy components (stream 4) of C9 and above from the bottom of the tower, wherein the content of the C8 component is less than 2 wt%;
(3) sending the C8 narrow fraction (stream 5) obtained in the step (2) into a first countercurrent liquid-liquid extraction deoxygenator C, wherein the content of oxides in the C8 narrow fraction is about 2.5 wt%, taking a mixture of propylene glycol and ethanolamine in a volume ratio of 1:1 as an extractant (stream 6), taking the volume flow ratio of the extractant (stream 6) to the C8 narrow fraction (stream 5) as 2:1, slowly adding the extractant from a distributor at the top of the tower, performing primary extraction deoxygenation, wherein the extraction temperature is 30 ℃, and about 3min after the extractant passes through the C8 narrow fraction, the two phases can be layered, so that the balance time for complete separation of the two phases is prolonged to 15 min; collecting and regenerating the extract (stream 8) for recycling;
(4) transferring the C8 narrow fraction (stream 7) obtained after the primary extraction deoxidation in the step (3) into a second countercurrent liquid-liquid extraction deoxidation tower D, wherein the oxide content in the C8 narrow fraction (stream 7) after the primary deoxidation is about 0.8 wt%, and performing secondary extraction deoxidation according to the flow of the step (3); collecting and regenerating the extract (stream 8) for recycling; the grade-I deoxidation adopts a fresh extracting agent, and the oxide content after deoxidation is less than 0.01 wt%, and the extracting agent can be used as an extracting agent for the grade-I extraction deoxidation;
(5) feeding the deoxidized C8 narrow fraction (stream 9) obtained in the step (4) into a methanol etherification reaction device E, adding a methanol solvent from the bottom of the reaction device, wherein the mass ratio of methanol to the C8 narrow fraction is 0.2:1, carrying out methanol etherification reaction under the mechanical stirring condition of the reaction temperature of 80 ℃ and 80r/min, wherein the reaction time is 2.0h, the reaction mainly removes part of methyl heptene, particularly 2-methyl-1-heptene, which affects the purity of a 1-octene product in the C8 narrow fraction, and generates corresponding methyl ether substances, and the boiling point is correspondingly increased by 20-30 ℃;
(6) sending the etherified C8 narrow fraction (stream 11) obtained in the step (5) into a lightness-removing column F from a 56 th tray, wherein the number of theoretical trays is 135, the number of plates in a rectifying section is 55, the number of plates in a stripping section is 80, the reflux ratio is 40, the operating pressure is normal pressure, lightness-removing treatment is carried out on the etherified C8 narrow fraction (stream 11), a heavy component C8 mixed solution (stream 13) is obtained at the bottom of the column, and the content of a 1-octene component in the heavy component at the bottom of the column is more than 58 wt%; recycling unreacted methanol solution (stream 12) obtained at the top of the tower, wherein the distillation rate at the top of the tower is 0.1, light components at the top of the tower are methyl heptene, methanol and other substances with the boiling point of 1-octene below, and the content of 1-octene in the light components is less than 65 wt%;
(7) feeding the tower bottom heavy component (stream 13) obtained in the step (6) into a precise rectifying tower G from a 77 th tower plate, wherein the number of theoretical plates is 140, the number of tower plates in a rectifying section is 76, the number of tower plates in a stripping section is 64, the reflux ratio is 40, the operating pressure is normal pressure, precise rectification is carried out on the tower bottom heavy component (stream 13), a 1-octene product (stream 14) is obtained at the tower top, and the distillation rate at the tower top is 0.60; the residual liquid at the bottom of the tower is a small amount of mixed solution (stream 15) of 1-octene, n-octane, isomeric octene, internal olefin, C8 etherate and the like, and the content of the 1-octene component in the heavy component at the bottom of the tower is less than 1 wt%.
Through detection, the purity of the 1-octene product finally obtained in the embodiment is 97.66 wt%, the yield is 87.5 wt%, and the obtained 1-octene product meets the ethylene copolymerization requirement and reaches the specifications of foreign 1-octene superior products.
The preferred embodiments of the present invention have been described in detail above with reference to the accompanying drawings, but the present invention is not limited thereto. Within the scope of the technical idea of the invention, many simple modifications can be made to the technical solution of the invention, including combinations of various technical features in any other suitable way, and these simple modifications and combinations should also be regarded as the disclosure of the invention, and all fall within the scope of the invention.
Claims (10)
1. A method for separating 1-octene from Fischer-Tropsch synthesis naphtha, which is characterized by comprising the following steps:
(1) rectifying Fischer-Tropsch synthesis oil-washed naphtha to obtain C8 narrow fraction;
(2) performing first-stage extraction deoxidation on the C8 narrow fraction to obtain a deoxidation product with the oxide content of 0.7-0.9 wt%; then, performing secondary extraction deoxidation on the deoxidation product to obtain deoxidation C8 narrow fraction with the oxide content of not more than 0.01 wt%;
(3) carrying out methanol etherification reaction on the deoxidized C8 narrow fraction to obtain an etherified C8 narrow fraction;
(4) and (3) carrying out light component removal rectification on the etherified C8 narrow fraction, and then carrying out precise rectification on heavy components in a tower bottom obtained by the light component removal rectification to obtain the 1-octene.
2. The process of claim 1 wherein the fischer-tropsch synthesis naphtha comprises C5-C12 paraffins and C5-C12 olefins, wherein alpha olefins constitute from 55 to 60 wt%, normal paraffins constitute from 25 to 30 wt%, beta olefins constitute from 5 to 10 wt%, and oxygenates constitute from 2 to 3 wt%.
3. The process of claim 1 or 2, wherein, in step (1), the rectification comprises a first rectification and a second rectification, and C7 and less light components in the Fischer-Tropsch synthesis oil-washed naphtha are removed through the first rectification to obtain C8 and more heavy components; removing heavy components of C9 and above in the C8 and above heavy components through the second rectification to obtain a C8 narrow fraction;
preferably, the first rectification is carried out in a first rectification tower, the theoretical plate number of the first rectification tower is 40, the plate number of a rectification section is 18, the plate number of a stripping section is 22, the reflux ratio is 5, and the operation pressure is normal pressure; the Fischer-Tropsch synthesis oil-washed naphtha enters the first rectifying tower from the 19 th tray, light components C7 and the following components are obtained from the top of the tower, the extraction rate is 0.38-0.44, the content of C8 in the light components is less than 1 wt%, heavy components C8 and the above components are obtained from the bottom of the tower, and the content of C7 and the following components in the heavy components is less than 1 wt%;
preferably, the second rectification is carried out in a second rectification tower, the theoretical plate number of the second rectification tower is 40, the plate number of the rectification section is 23, the plate number of the stripping section is 17, the reflux ratio is 5, and the operation pressure is normal pressure; the heavy components in the tower bottom obtained by the first rectifying tower are added into the second rectifying tower from a 24 th tower plate, a C8 narrow fraction is obtained from the tower top, the extraction rate is 0.5-0.57, and the content of C7 and the following components is less than 3 wt%; obtaining components with the weight of more than C8 from the tower bottom, wherein the content of the C8 component is less than 2 wt%;
preferably, the content of the C8 components in the C8 narrow fraction is more than 97 wt%, and the content of the oxides is 2.2-2.8 wt%.
4. The method according to any one of claims 1 to 3, wherein in the step (2), the primary extraction deoxidation is countercurrent liquid-liquid extraction deoxidation, the temperature of the primary extraction deoxidation is 15-40 ℃, and the time is 10-15 min;
preferably, the first-stage extraction deoxidation adopts a first extracting agent, and the first extracting agent is a compound solvent of an alcohol organic solvent and an amine organic solvent in a volume ratio of 1:1-2: 1;
preferably, the alcohol organic solvent is at least one of 1, 4-butanediol, 1, 2-propanediol, ethylene glycol and methanol;
preferably, the amine organic solvent is at least one of N, N-dimethylformamide, ethanolamine, diethanolamine and isopropanolamine;
preferably, the volume flow ratio of the first extracting agent to the C8 narrow fraction is 2:1-4: 1;
preferably, the density of the first extractant is 1.07 to 1.13g/cm 3 。
5. The method according to any one of claims 1 to 4, wherein in the step (2), the secondary extraction deoxidation is countercurrent liquid-liquid extraction deoxidation, the temperature of the secondary extraction deoxidation is 15-40 ℃, and the time is 10-15 min;
preferably, a second extracting agent is adopted for secondary extraction deoxidation, and the second extracting agent is a compound solvent of an alcohol organic solvent and an amine organic solvent in a volume ratio of 1:1-2: 1;
preferably, the alcohol organic solvent is at least one of 1, 4-butanediol, 1, 2-propanediol, ethylene glycol and methanol;
preferably, the amine organic solvent is at least one of N, N-dimethylformamide, ethanolamine, diethanolamine and isopropanolamine;
preferably, the volume flow ratio of the second extracting agent to the C8 narrow fraction is 2:1-4: 1;
preferably, the density of the second extractant is 1.07 to 1.13g/cm 3 ；
Preferably, the second extracting agent is used as the extracting agent for the primary extraction deoxidation when the oxide content is below 0.01 percent after the second extraction deoxidation is used for the secondary extraction deoxidation.
6. The process according to any one of claims 1 to 5, wherein, in the step (3), the methanol is etherified at 80 to 90 ℃ for 1.5 to 2.0 h;
preferably, in the methanol etherification reaction, the mass ratio of methanol to the deoxidized C8 narrow fraction is 0.2:1-0.3: 1;
preferably, the catalyst for the methanol etherification reaction is a large-particle acidic resin catalyst.
7. The process as claimed in any one of claims 1 to 6, wherein, in the step (4), the lightness-removing rectification is carried out in a lightness-removing rectification column having a theoretical plate number of 135, a rectification stage plate number of 55, a stripping stage plate number of 80, a reflux ratio of 40, and an operating pressure of normal pressure; and (4) adding the reacted C8 narrow fraction obtained in the step (3) into the light component removal rectifying tower from a 56 th tower plate, wherein the light component obtained from the tower top is a substance below the boiling point of 1-octene, the distillation rate extracted from the tower top is 0.08-0.1, the content of 1-octene in the light component is less than 65 wt%, and the content of 1-octene in the heavy component obtained from the tower bottom is more than 58 wt%.
8. The process as claimed in any one of claims 1 to 7, wherein, in step (4), the precision rectification is carried out in a precision rectification column having a theoretical plate number of 140, a rectifying section plate number of 76, a stripping section plate number of 64, a reflux ratio of 40, and an operating pressure of normal pressure; and the heavy component in the tower bottom of the light component removal rectifying tower is added into the precise rectifying tower from the 77 th tower plate, the purity of 1-octene in the light component obtained from the tower top is more than 97 wt%, the distillation rate at the tower top is 0.57-0.60, and the content of 1-octene in the heavy component obtained from the tower bottom is less than 1 wt%.
9. The device for separating 1-octene from Fischer-Tropsch synthetic oil washed naphtha is characterized by comprising a first rectifying tower, a second rectifying tower, a first counter-current liquid-liquid extraction deoxygenation tower, a second counter-current liquid-liquid extraction deoxygenation tower, methanol etherification reaction equipment, a light component removal rectifying tower and a precise rectifying tower which are sequentially communicated.
10. The apparatus of claim 9, wherein the first rectification column has a theoretical plate number of 40, a rectification section plate number of 18, a stripping section plate number of 22, and a feed plate number of 19; and/or the presence of a gas in the gas,
the theoretical plate number of the second rectifying tower is 40, the rectifying section plate number is 23, the stripping section plate number is 17, and the feeding plate number is 24; and/or the presence of a gas in the gas,
the first countercurrent liquid-liquid extraction deoxygenation tower and the second countercurrent liquid-liquid extraction deoxygenation tower are sieve plate towers or packed towers; and/or the presence of a gas in the gas,
the methanol etherification reaction equipment is a fixed bed catalytic reactor, a catalyst bed layer is arranged in the fixed bed catalytic reactor, a stirring paddle is arranged at the bottom of the fixed bed catalytic reactor, and a condensation reflux part is arranged at the top of the fixed bed catalytic reactor; and/or the presence of a gas in the gas,
the number of theoretical plates of the light component removal rectifying tower is 135, the number of plates of a rectifying section is 55, the number of plates of a stripping section is 80, and the number of plates of a feeding tower is 56; and/or the presence of a gas in the gas,
the precise rectifying tower has theoretical plate number of 140, rectifying section plate number of 76, stripping section plate number of 64 and feeding plate number of 77.
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