CN115108880A - Method for separating methylcyclopentane and methylene cyclopentane - Google Patents
Method for separating methylcyclopentane and methylene cyclopentane Download PDFInfo
- Publication number
- CN115108880A CN115108880A CN202210941604.0A CN202210941604A CN115108880A CN 115108880 A CN115108880 A CN 115108880A CN 202210941604 A CN202210941604 A CN 202210941604A CN 115108880 A CN115108880 A CN 115108880A
- Authority
- CN
- China
- Prior art keywords
- methylcyclopentane
- rectifying
- organic oxygen
- cyclopentane
- mixed solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- NFJPEKRRHIYYES-UHFFFAOYSA-N methylidenecyclopentane Chemical compound C=C1CCCC1 NFJPEKRRHIYYES-UHFFFAOYSA-N 0.000 title claims abstract description 162
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 title claims abstract description 142
- 238000000034 method Methods 0.000 title claims abstract description 21
- 239000007788 liquid Substances 0.000 claims abstract description 45
- 238000000926 separation method Methods 0.000 claims abstract description 37
- 239000011259 mixed solution Substances 0.000 claims abstract description 30
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 28
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 28
- 239000001301 oxygen Substances 0.000 claims abstract description 28
- 238000012856 packing Methods 0.000 claims description 33
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 8
- 239000005977 Ethylene Substances 0.000 claims description 8
- 238000006384 oligomerization reaction Methods 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 8
- BVUXDWXKPROUDO-UHFFFAOYSA-N 2,6-di-tert-butyl-4-ethylphenol Chemical compound CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BVUXDWXKPROUDO-UHFFFAOYSA-N 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 239000011148 porous material Substances 0.000 claims description 7
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 claims description 6
- 239000004711 α-olefin Substances 0.000 claims description 6
- PFEFOYRSMXVNEL-UHFFFAOYSA-N 2,4,6-tritert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 PFEFOYRSMXVNEL-UHFFFAOYSA-N 0.000 claims description 4
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 4
- HNURKXXMYARGAY-UHFFFAOYSA-N 2,6-Di-tert-butyl-4-hydroxymethylphenol Chemical compound CC(C)(C)C1=CC(CO)=CC(C(C)(C)C)=C1O HNURKXXMYARGAY-UHFFFAOYSA-N 0.000 claims description 3
- 235000010354 butylated hydroxytoluene Nutrition 0.000 claims description 3
- 239000000919 ceramic Substances 0.000 claims description 3
- 239000004033 plastic Substances 0.000 claims description 3
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 claims description 3
- 229910010271 silicon carbide Inorganic materials 0.000 claims description 3
- KDBZVULQVCUNNA-UHFFFAOYSA-N 2,5-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(C(C)(C)C)C(O)=C1 KDBZVULQVCUNNA-UHFFFAOYSA-N 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 238000000605 extraction Methods 0.000 description 33
- 238000005086 pumping Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- 150000001717 carbocyclic compounds Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
-
- 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
- C07C7/04—Purification; Separation; Use of additives by distillation
- C07C7/05—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for separating methylcyclopentane and methylenecyclopentane, which comprises the following steps: (1) adding an organic oxygen-containing compound into a mixed solution I of methylcyclopentane and methylenecyclopentane to obtain a mixed solution II; (2) separating the mixed solution II through a first separation unit to obtain methylcyclopentane and a mixed solution III containing the methylenecyclopentane and an organic oxygen-containing compound; (3) the mixed liquid III is separated into methylene cyclopentane and organic oxygen-containing compounds in a second separation unit. The method can realize the high-efficiency separation of methylcyclopentane and methylene cyclopentane, and the purity of the separated methylcyclopentane reaches more than 99.8%.
Description
Technical Field
The invention belongs to the field of chemical separation, and particularly relates to a method for separating a mixed solution of methylcyclopentane and methylene cyclopentane.
Background
Methyl cyclopentane is an important chemical intermediate for organic synthesis, and can also be used in the fields of chemical solvents, azeotropic distillation agents, extraction agents and the like. Methylene cyclopentane is an important raw material for organic synthesis, five-membered carbocyclic compounds with various functional groups can be obtained from methylene cyclopentane, and the five-membered carbocyclic compounds are used for synthesizing fine chemicals and medical intermediates, and the market price of the five-membered carbocyclic compounds is high.
In the process for preparing alpha-olefin by ethylene selective oligomerization, the yield of the byproduct methylcyclopentane and methylene cyclopentane is 3-6% of the total product, and the mass ratio of the two products is about 1: 1. However, the boiling points of methylcyclopentane and methylenecyclopentane are very close (72 ℃ for methylcyclopentane and 75 ℃ for methylenecyclopentane), so that the separation and purification of the two are very difficult. If the separation of the methyl cyclopentane and the methylene cyclopentane can be realized to obtain purified methyl cyclopentane and methylene cyclopentane, the reuse of byproducts is realized, the additional value of the byproducts in the ethylene oligomerization process can be improved, and the economic benefit and the environmental benefit of enterprises can be effectively improved.
At present, some processes for separating methylcyclopentane from methylenecyclopentane are reported, but the separation process has high energy consumption and poor separation effect, high-purity products cannot be obtained, and the products are difficult to sell outside, thereby causing resource waste. Therefore, how to create a simple and easy method for separating and purifying methylcyclopentane and methylene cyclopentane with high product purity belongs to the problem which needs to be solved urgently in the industry.
Disclosure of Invention
In order to overcome the deficiencies of the prior art, the present invention provides a method for separating methylcyclopentane from methylenecyclopentane. The boiling points of the methylcyclopentane and the methylene cyclopentane are very close, the conventional rectification cannot realize effective separation of the methylcyclopentane and the methylene cyclopentane, high-purity methylcyclopentane and methylene cyclopentane are difficult to obtain, the relative volatility of the methylcyclopentane and the methylene cyclopentane is changed after the organic oxygen-containing compound is added, and the enhanced mass transfer effect of the hypergravity rectification enables the methylcyclopentane and the methylene cyclopentane to be efficiently separated.
In order to achieve the purpose of the invention, the technical scheme adopted by the invention is as follows:
a process for separating methylcyclopentane from methylenecyclopentane, comprising the steps of:
(1) adding an organic oxygen-containing compound into a mixed solution I of methylcyclopentane and methylene cyclopentane to obtain a mixed solution II;
(2) separating the mixed solution II through a first separation unit to obtain methylcyclopentane and a mixed solution III containing methylenecyclopentane and an organic oxygen-containing compound;
(3) the mixed liquid III is separated into methylene cyclopentane and organic oxygen-containing compounds in a second separation unit.
Further, the mass ratio of the methylcyclopentane to the methylenecyclopentane in the mixed solution I in the step (1) is 1:10-10: 1.
In the invention, the mixed liquid I can be a mixed liquid containing methylcyclopentane and methylene cyclopentane, which is obtained in the rectification and purification process of preparing alpha-olefin by selective oligomerization of ethylene.
Further, the organic oxygen-containing compound in the step (1) is an alkylphenol containing a tertiary butyl group, and is selected from one or more of 2, 6-di-tertiary-butylphenol, 2, 6-di-tertiary-butyl-4-methylphenol, 2, 6-di-tertiary-butyl-4-ethylphenol, 2,4, 6-tri-tertiary-butylphenol, 2, 5-di-tertiary-butylphenol and 4-hydroxymethyl-2, 6-di-tertiary-butylphenol. The amount of the organic oxygen-containing compound added is 1 to 40% by mass, preferably 5 to 20% by mass of the mixed solution I.
Further, in the step (2), the first separation unit may adopt reduced pressure hypergravity rectification, and the internal rotor packing of the hypergravity rectification machine adopted in the hypergravity rectification is corrugated structured packing, and the corrugated structured packing is selected from one or more of the following packing combinations: silicon carbide corrugated structured packing, plastic pore plate corrugated structured packing, ceramic corrugated structured packing, metal pore plate corrugated structured packing and metal wire mesh corrugated structured packing; preferably a metal orifice plate corrugated structured packing.
Further, the internal diameter range of the structured packing of the hypergravity rectifying machine in the step (2) is as follows: 50-300 mm, 100-1000 mm in outer diameter and 50-600 mm in height.
Further, in the step (2), the range of the vacuum degree (absolute pressure) of the supergravity rectifying machine in working is 0.1-50 KPa, and the range of the rotating speed is 300-2000 rpm.
And further pumping the mixed liquid II containing the methylcyclopentane, the methylene cyclopentane and the organic oxygen-containing compound into a hypergravity rectifying machine through a feed pump, condensing the methylcyclopentane vapor from the top of the rectifying machine through a condenser, and then feeding the condensed vapor into a condensing tank to obtain the high-purity methylcyclopentane. And collecting a mixed liquid III containing methylene cyclopentane and the organic oxygen-containing compound from a reboiler at the bottom of the rectifying tower, and separating the methylene cyclopentane and the organic oxygen-containing compound through a second separation unit.
The second separation unit can adopt common separation modes such as rectification or crystallization, preferably rectification separation, more preferably a plate-type rectification tower, high-purity methylene cyclopentane is extracted from the top of the plate-type rectification tower, and organic oxygen-containing compounds are extracted from the bottom of the plate-type rectification tower.
Further, in the step (3), the number of the plate-type rectifying tower is 20-100, the rectifying vacuum degree (absolute pressure) is 0.5-20 KPa, the reflux ratio is 1:10-10:1, and the tower kettle temperature is 100-.
The invention has the beneficial effects that: according to the invention, the organic oxygen-containing compound is added into the mixed liquid of the methylcyclopentane and the methylene cyclopentane, so that the relative volatility of the methylcyclopentane and the methylene cyclopentane is changed, the two are relatively easier to separate, and the mass transfer effect is enhanced through the supergravity rectification, so that the separation of the methylcyclopentane and the methylene cyclopentane with extremely close boiling points is realized, and the high separation precision (the purity of the two after separation can reach more than 99.8%) can be obtained, the bottleneck that the conventional separation method cannot obtain the high-purity methylcyclopentane and the methylene cyclopentane is broken through, the high added value of the ethylene selective oligomerization by-product is realized, and the waste of resources is avoided.
Detailed Description
The technical solutions of the present invention are further described below, but not limited thereto, and modifications or equivalent substitutions may be made to the technical solutions of the present invention without departing from the scope of the technical solutions of the present invention.
Example 1:
the hypergravity rectifying machine uses a metal pore plate corrugated structured packing with the structured packing specification of 120mm in inner diameter, 500mm in outer diameter and 50mm in height, the mass ratio of methylcyclopentane to methylene cyclopentane in the mixed liquid I to be separated is 1:1, and 2, 6-di-tert-butylphenol with the mass of 10% of the mixed liquid is added into the mixed liquid I to obtain a mixed liquid II.
In this embodiment, the first separation unit is a supergravity rectifying machine, the second separation unit is a plate-type rectifying tower, the supergravity rectifying machine is set to have a vacuum degree (absolute pressure) of 10KPa, and the rotation speed is set to be 800 rpm. The plate number of the plate type rectifying tower is 30, the rectifying vacuum degree (absolute pressure) is 10KPa, the reflux ratio is 1:5, and the temperature of the tower kettle is 160 ℃.
And (3) pumping the mixed liquid II to be purified into the hypergravity rectifying machine by using a feed pump, and after the device operates stably, starting a condenser extraction valve at the top of the rectifying machine, a plate-type rectifying tower top extraction valve and a tower kettle extraction valve to perform continuous vacuum rectification operation. And (3) extracting high-purity methyl cyclopentane from an extraction valve of a condenser of the rectifying machine: 99.83% of methyl cyclopentane and 0.17% of methylene cyclopentane. And (3) extracting a mixed solution III containing methylene cyclopentane and an organic oxygen-containing compound from a reboiler at the bottom of the rectifying tower, separating the mixed solution III through a plate rectifying tower, and extracting high-purity methylene cyclopentane from a extraction valve at the top of the plate rectifying tower: 0.12 percent of methyl cyclopentane, 99.88 percent of methylene cyclopentane and 2, 6-di-tert-butylphenol extracted from a tower bottom extraction valve of the plate rectifying tower.
Example 2:
the hypergravity rectifying machine uses silicon carbide corrugated structured packing with the structured packing specification of 50mm in inner diameter, 100mm in outer diameter and 300mm in height, the mass ratio of methylcyclopentane to methylene cyclopentane in the mixed liquid I to be separated is 1:5, and 2, 6-di-tert-butyl-4-methylphenol accounting for 30% of the mixed liquid mass is added into the mixed liquid I to obtain the mixed liquid II.
In this embodiment, the first separation unit is a supergravity rectifying machine, the second separation unit is a plate-type rectifying tower, the supergravity rectifying machine is set to have a vacuum degree (absolute pressure) of 30KPa, and the rotation speed is set to be 1500 rpm. The plate number of the plate type rectifying tower is 100, the rectifying vacuum degree (absolute pressure) is 15KPa, the reflux ratio is 1:10, and the temperature of a tower kettle is 120 ℃.
And (3) pumping the mixed liquid II to be purified into the hypergravity rectifying machine by using a feed pump, and after the device operates stably, starting a condenser extraction valve at the top of the rectifying machine, a plate-type rectifying tower top extraction valve and a tower kettle extraction valve to perform continuous vacuum rectification operation. And (3) extracting high-purity methyl cyclopentane from an extraction valve of a condenser of the rectifying machine: 99.85% of methyl cyclopentane and 0.15% of methylene cyclopentane. And (3) extracting a mixed solution III containing methylene cyclopentane and an organic oxygen-containing compound from a reboiler at the bottom of the rectifying tower, separating the mixed solution III through a plate rectifying tower, and extracting high-purity methylene cyclopentane from a extraction valve at the top of the plate rectifying tower: 0.16 percent of methyl cyclopentane, 99.84 percent of methylene cyclopentane and 2, 6-di-tert-butyl-4-methylphenol extracted from a tower bottom extraction valve of a plate rectifying tower.
Example 3:
the hypergravity rectifying machine uses a plastic pore plate corrugated structured packing with the structured packing specification of 200mm in inner diameter, 800mm in outer diameter and 150mm in height, the mass ratio of methylcyclopentane to methylene cyclopentane in the mixed liquid I to be separated is 1:10, and 2, 6-di-tert-butyl-4-ethylphenol with the mass of 1% of the mixed liquid is added into the mixed liquid I to obtain a mixed liquid II.
In this embodiment, the first separation unit is a supergravity rectifying machine, the second separation unit is a plate-type rectifying tower, the supergravity rectifying machine is set to have a vacuum degree (absolute pressure) of 50KPa, and the rotation speed is set to 2000 rpm. The plate number of the plate-type rectifying tower is 80, the rectifying vacuum degree (absolute pressure) is 20KPa, the reflux ratio is 1:1, and the temperature of a tower kettle is 140 ℃.
And (3) pumping the mixed liquid II to be purified into the hypergravity rectifying machine by using a feed pump, and after the device operates stably, starting a condenser extraction valve at the top of the rectifying machine, a plate-type rectifying tower top extraction valve and a tower kettle extraction valve to perform continuous vacuum rectification operation. Extracting high-purity methyl cyclopentane from an extraction valve of a condenser of the rectifying machine: 99.81% of methylcyclopentane and 0.19% of methylene cyclopentane. And (3) extracting a mixed solution III containing methylene cyclopentane and an organic oxygen-containing compound from a reboiler at the bottom of the rectifying tower, separating the mixed solution III through a plate rectifying tower, and extracting high-purity methylene cyclopentane from a extraction valve at the top of the plate rectifying tower: 0.17 percent of methyl cyclopentane, 99.83 percent of methylene cyclopentane and 2, 6-di-tert-butyl-4-ethylphenol extracted from a tower bottom extraction valve of a plate rectifying tower.
Example 4:
the hypergravity rectifying machine uses ceramic corrugated structured packing with the standard of the inner diameter of 300mm, the outer diameter of 1000mm and the height of 600mm, the mass ratio of methylcyclopentane to methylenecyclopentane in the mixed liquid I to be separated is 10:1, and 2,4, 6-tri-tert-butylphenol accounting for 40% of the mixed liquid mass is added into the mixed liquid I to obtain the mixed liquid II.
In this embodiment, the first separation unit is a supergravity rectifying machine, the second separation unit is a plate-type rectifying tower, the supergravity rectifying machine is set to have a vacuum degree (absolute pressure) of 2KPa, and the rotation speed is set to be 1100 rpm. The plate number of the plate type rectifying tower is 20, the rectifying vacuum degree (absolute pressure) is 3KPa, the reflux ratio is 5:1, and the temperature of a tower kettle is 180 ℃.
And (3) pumping the mixed liquid II to be purified into the hypergravity rectifying machine by using a feed pump, and after the device operates stably, starting a condenser extraction valve at the top of the rectifying machine, a plate-type rectifying tower top extraction valve and a tower kettle extraction valve to perform continuous vacuum rectification operation. And (3) extracting high-purity methyl cyclopentane from an extraction valve of a condenser of the rectifying machine: 99.87% of methyl cyclopentane and 0.13% of methylene cyclopentane. And (3) extracting a mixed solution III containing methylene cyclopentane and an organic oxygen-containing compound from a reboiler at the bottom of the rectifying tower, separating the mixed solution III through a plate rectifying tower, and extracting high-purity methylene cyclopentane from a extraction valve at the top of the plate rectifying tower: 0.10 percent of methyl cyclopentane, 99.90 percent of methylene cyclopentane and 2,4, 6-tri-tert-butylphenol extracted from a tower bottom extraction valve of a plate type rectifying tower.
Example 5:
the hypergravity rectifying machine uses a wire mesh corrugated structured packing with the structured packing specification of 90mm inner diameter, 300mm outer diameter and 450mm height, mixed liquid of methyl cyclopentane and methylene cyclopentane obtained in the process of rectifying and purifying alpha-olefin by selective oligomerization of ethylene is taken as mixed liquid I, wherein the mass ratio of the methyl cyclopentane to the methylene cyclopentane in the mixed liquid I is 5:1, and 2, 6-di-tert-butylphenol accounting for 20% of the mass of the mixed liquid is added into the mixed liquid I to obtain mixed liquid II.
In this embodiment, the first separation unit is a supergravity rectifying machine, the second separation unit is a plate-type rectifying tower, the supergravity rectifying machine is set to have a vacuum degree (absolute pressure) of 0.1KPa, and the rotation speed is set to be 300 rpm. The plate number of the plate type rectifying tower is 50, the rectifying vacuum degree (absolute pressure) is 0.5KPa, the reflux ratio is 3:1, and the temperature of a tower kettle is 100 ℃.
And (3) pumping the mixed liquid II to be purified into the hypergravity rectifying machine by using a feed pump, and after the device operates stably, starting a condenser extraction valve at the top of the rectifying machine, a plate-type rectifying tower top extraction valve and a tower kettle extraction valve to perform continuous vacuum rectification operation. And (3) extracting high-purity methyl cyclopentane from an extraction valve of a condenser of the rectifying machine: 99.85% of methyl cyclopentane and 0.15% of methylene cyclopentane. And (2) extracting a mixed solution III containing methylene cyclopentane and an organic oxygen-containing compound from a reboiler at the bottom of the rectifying tower, separating the mixed solution III through a plate rectifying tower, and extracting high-purity methylene cyclopentane from a top extraction valve of the plate rectifying tower: 0.16 percent of methyl cyclopentane, 99.84 percent of methylene cyclopentane and 2, 6-di-tert-butylphenol extracted from a tower bottom extraction valve of a plate type rectifying tower.
Comparative example 1:
the hypergravity rectifying machine uses a wire mesh corrugated structured packing with the structured packing specification of 90mm in inner diameter, 300mm in outer diameter and 450mm in height, mixed liquid of methyl cyclopentane and methylene cyclopentane obtained in the process of rectifying and purifying alpha-olefin by selective oligomerization of ethylene is taken as mixed liquid I, wherein the mass ratio of the methyl cyclopentane to the methylene cyclopentane in the mixed liquid I is 5: 1.
The vacuum degree (absolute pressure) of the hypergravity rectifying machine is set to be 0.1KPa, and the rotating speed is set to be 300 rpm. And (3) pumping the mixed liquid I to be purified into the hypergravity rectifying machine by using a feed pump, starting a condenser extraction valve at the top of the rectifying machine and a tower kettle extraction valve after the device is stably operated, and carrying out continuous vacuum rectification operation. The produced liquid of the tower top condenser of the rectifying machine comprises the following components: 92.32% of methylcyclopentane and 7.68% of methylene cyclopentane. The composition of the produced liquid at the tower bottom of the rectifying machine is as follows: 5.63% of methylcyclopentane and 94.37% of methylene cyclopentane.
Comparative example 2:
separating by using a plate type rectifying tower, wherein the number of plates of the rectifying tower is 50, the rectifying vacuum degree (absolute pressure) is 0.5KPa, the reflux ratio is 3:1, and the temperature of a tower kettle is 100 ℃. Taking a mixed solution of methylcyclopentane and methylenecyclopentane obtained in the rectification and purification process of preparing alpha-olefin through selective oligomerization of ethylene as a mixed solution I, wherein the mass ratio of the methylcyclopentane to the methylenecyclopentane in the mixed solution I is 5: 1. The produced liquid of the overhead condenser of the plate-type rectifying tower comprises the following components: 88.39% of methylcyclopentane and 11.61% of methylene cyclopentane. The produced liquid at the tower bottom of the plate rectifying tower comprises the following components: 10.62 percent of methylcyclopentane and 89.38 percent of methylene cyclopentane.
Claims (9)
1. A process for separating methylcyclopentane from methylenecyclopentane, comprising the steps of:
(1) adding an organic oxygen-containing compound into a mixed solution I of methylcyclopentane and methylene cyclopentane to obtain a mixed solution II;
(2) separating the mixed solution II through a first separation unit to obtain methylcyclopentane and a mixed solution III containing the methylenecyclopentane and an organic oxygen-containing compound;
(3) the mixed liquid III is separated into methylene cyclopentane and organic oxygen-containing compounds in a second separation unit.
2. The method according to claim 1, wherein the mass ratio of methylcyclopentane to methylenecyclopentane in the mixed solution I in step (1) is 1:10-10: 1.
3. The method as claimed in claim 1, wherein the mixed liquor I can be a mixed liquor containing methylcyclopentane and methylenecyclopentane obtained in the rectification and purification process of preparing alpha-olefin by selective oligomerization of ethylene.
4. The method according to claim 1, wherein the organic oxygen-containing compound in step (1) is a tert-butyl group-containing alkylphenol selected from one or more of 2, 6-di-tert-butylphenol, 2, 6-di-tert-butyl-4-methylphenol, 2, 6-di-tert-butyl-4-ethylphenol, 2,4, 6-tri-tert-butylphenol, 2, 5-di-tert-butylphenol, and 4-hydroxymethyl-2, 6-di-tert-butylphenol.
5. The method according to claim 1, wherein the amount of the organic oxygen-containing compound added is 1 to 40%, preferably 5 to 20% by mass of the mixed solution I.
6. The method of claim 1, wherein in step (2), the first separation unit is obtained by vacuum super-gravity distillation,
preferably, the internal rotor packing of the hypergravity rectifying machine adopted by the hypergravity rectification is corrugated regular packing, and the corrugated regular packing is selected from one or more of the following packing combinations: silicon carbide corrugated structured packing, plastic pore plate corrugated structured packing, ceramic corrugated structured packing, metal pore plate corrugated structured packing and metal wire mesh corrugated structured packing; preferably, the corrugated structured packing of the metal pore plate;
preferably, in the step (2), the internal diameter range of the structured packing of the hypergravity rectifying machine is as follows: 50-300 mm, 100-1000 mm in outer diameter and 50-600 mm in height.
Preferably, in the step (2), the range of the vacuum degree (absolute pressure) of the supergravity rectifying machine in work is 0.1-50 KPa, and the range of the rotating speed is 300-2000 rpm.
7. The method according to any one of claims 1 to 6, characterized in that the mixed liquid II containing methylcyclopentane, methylenecyclopentane and organic oxygen-containing compounds is pumped into a hypergravity rectifying machine by a feed pump, and the methylcyclopentane vapor enters a condensing tank after being condensed by a condenser from the top of the rectifying machine to obtain high-purity methylcyclopentane; and collecting a mixed liquid III containing methylene cyclopentane and the organic oxygen-containing compound from a reboiler at the bottom of the rectifying tower, and separating the methylene cyclopentane and the organic oxygen-containing compound through a second separation unit.
8. The method according to any one of claims 1 to 7, wherein the second separation unit is a rectification or crystallization separation method, preferably a rectification separation method, more preferably a plate-type rectification tower;
preferably, high-purity methylene cyclopentane is extracted from the top of the plate-type rectifying tower, and organic oxygen-containing compounds are extracted from the bottom of the tower.
9. The method as claimed in any one of claims 1 to 8, wherein the number of plates in the plate-type rectification column in the step (3) is 20 to 100, the rectification vacuum degree (absolute pressure) is 0.5 to 20KPa, the reflux ratio is 1:10 to 10:1, and the temperature in the column bottom is 100 ℃ to 200 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210941604.0A CN115108880B (en) | 2022-08-08 | 2022-08-08 | Method for separating methylcyclopentane and methylenecyclopentane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210941604.0A CN115108880B (en) | 2022-08-08 | 2022-08-08 | Method for separating methylcyclopentane and methylenecyclopentane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN115108880A true CN115108880A (en) | 2022-09-27 |
| CN115108880B CN115108880B (en) | 2023-12-19 |
Family
ID=83334227
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210941604.0A Active CN115108880B (en) | 2022-08-08 | 2022-08-08 | Method for separating methylcyclopentane and methylenecyclopentane |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN115108880B (en) |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1418654A1 (en) * | 1960-02-15 | 1968-12-12 | British Petroleum Co | Process for the isomerization of hydrocarbons |
| GB1221886A (en) * | 1968-07-29 | 1971-02-10 | Monsanto Co | Separation of hydrocarbons |
| WO1998044076A1 (en) * | 1996-02-05 | 1998-10-08 | Japan Energy Corporation | Process for preparing methylcyclopentane-containing hydrocarbon |
| CN101448765A (en) * | 2006-05-19 | 2009-06-03 | 国际壳牌研究有限公司 | Process for the alkylation of a cycloalkene |
| CN102264673A (en) * | 2008-12-24 | 2011-11-30 | 住友精化株式会社 | Method and apparatus for purifying paraffin |
| CN102485708A (en) * | 2010-12-03 | 2012-06-06 | 中国石油化工股份有限公司 | C5 fraction separation method employing hypergravity extractive distillation apparatus |
-
2022
- 2022-08-08 CN CN202210941604.0A patent/CN115108880B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1418654A1 (en) * | 1960-02-15 | 1968-12-12 | British Petroleum Co | Process for the isomerization of hydrocarbons |
| GB1221886A (en) * | 1968-07-29 | 1971-02-10 | Monsanto Co | Separation of hydrocarbons |
| WO1998044076A1 (en) * | 1996-02-05 | 1998-10-08 | Japan Energy Corporation | Process for preparing methylcyclopentane-containing hydrocarbon |
| CN101448765A (en) * | 2006-05-19 | 2009-06-03 | 国际壳牌研究有限公司 | Process for the alkylation of a cycloalkene |
| CN102264673A (en) * | 2008-12-24 | 2011-11-30 | 住友精化株式会社 | Method and apparatus for purifying paraffin |
| CN102485708A (en) * | 2010-12-03 | 2012-06-06 | 中国石油化工股份有限公司 | C5 fraction separation method employing hypergravity extractive distillation apparatus |
Non-Patent Citations (1)
| Title |
|---|
| 洪岭;林如海;孙维;徐婷婷;霍宏亮;王紫东;: "甲基环戊烷和亚甲基环戊烷的应用研究进展", 精细石油化工 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN115108880B (en) | 2023-12-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1202072C (en) | Prodn. process of high pureness xylylene amine | |
| CN107501152B (en) | A kind of separation method of tert-butyl hydroperoxide | |
| WO2017133357A1 (en) | Method, process, and apparatus for separating ethylene glycol and 1,2-butylene glycol | |
| CN109180442A (en) | A kind of method that the adsorbing coupled technique of extracting rectifying-recycles methyl tertiary butyl ether(MTBE) in pharmacy procedure waste liquid | |
| KR20190008895A (en) | An integrated process for preparing propene and propene oxide from propane | |
| CN104926690B (en) | The recovery process for purification and device of acetonitrile in a kind of synthesis for Ceftriaxone Sodium | |
| EP1301471A2 (en) | Process for the purification and recovery of acetonitrile | |
| CN111170823B (en) | Method for simultaneously extracting phenol and naphthalene from tar | |
| KR100888065B1 (en) | Improvedprocess for methyl acetate hydrolysis | |
| CN102531834A (en) | System and process for recovering waste liquid in 1, 4-butanediol production process | |
| CN115108880A (en) | Method for separating methylcyclopentane and methylene cyclopentane | |
| CN101014582A (en) | Process | |
| CN1807381A (en) | Crotonaldehyde production process | |
| CN112457230B (en) | Separation and purification method of ethylene imine | |
| CN1034540A (en) | The method of separating aldehyde impurity and oxyethane | |
| CN109336847A (en) | A kind of distillation system and its workflow recycling propylene oxide raffinate | |
| KR100339973B1 (en) | Method and apparatus of methyl acetate hydrolysis | |
| CN204727810U (en) | A kind of purification and recover device for acetonitrile in ceftriaxone sodium synthesis | |
| JP2008184409A (en) | Distillation method of alkylamine-containing mixture and method for producing alkylamines | |
| CN111202999B (en) | Rectification device and method for extracting high-purity mesitylene product from oil generated by isomerization reaction of trimethylbenzene | |
| CN114163332B (en) | Process for preparing dimethyl carbonate by removing methanol from near-azeotropic-concentration dimethyl carbonate-methanol mixture | |
| CN216934753U (en) | Rectifying device for recovering toluene and dimethyl tetrahydrofuran | |
| CN110724041B (en) | Separation method of glycerol monomethyl ether reaction mixed liquid | |
| CN113968768B (en) | Propylene recovery method and apparatus, epoxidation reaction product separation method and apparatus, and epoxidation method and epoxidation system | |
| CN108623474A (en) | It is a kind of to purify N, N, N, the method for N- tetramethyl-1,3-propane diamines using azeotropic distillation |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |