CA2136496A1 - Method for the separation of propylene/propane mixtures - Google Patents
Method for the separation of propylene/propane mixturesInfo
- Publication number
- CA2136496A1 CA2136496A1 CA002136496A CA2136496A CA2136496A1 CA 2136496 A1 CA2136496 A1 CA 2136496A1 CA 002136496 A CA002136496 A CA 002136496A CA 2136496 A CA2136496 A CA 2136496A CA 2136496 A1 CA2136496 A1 CA 2136496A1
- Authority
- CA
- Canada
- Prior art keywords
- propylene
- propane
- absorption
- water
- separation
- 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.)
- Abandoned
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/11—Purification; Separation; Use of additives by absorption, i.e. purification or separation of gaseous hydrocarbons with the aid of liquids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
- C07C11/06—Propene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C9/00—Aliphatic saturated hydrocarbons
- C07C9/02—Aliphatic saturated hydrocarbons with one to four carbon atoms
- C07C9/08—Propane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Analytical Chemistry (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Gas Separation By Absorption (AREA)
Abstract
To separate propylene/propane mixtures, the unsaturated hydrocarbon is absorbed by water. The absorption can be reinforced by addition of phase transfer reagents to the water.
Description
- 2136~96 Method for the seParation of propylene/propane mixtures The invention relates to a method for the separation of propylene/propane mixtures by selective absorption. Water serves as absorption medium to which phase transfer reagents (solubilizers) can be added.
The separation of propylene/propane mixture i8 an object which is frequently required in refinery technology as in the chemical industry. Its aim is either the isolation of the pure hydrocarbons or else the recovery of one of the two components, in particular the propylene, eg. from off-gases.
Depending on the required purity at which the constitu-ents must be obtained from their mixtures, different methods are used. Thus, by the method of DE-A-3 412 336, the off-gas of propylene hydroformylation is partially condensed, it conventionally contains 25 to 40% by volume of propylene, 6 to 20% by volume of propane and, in addition, hydrogen and carbon monoxide, the condensate is rectified and the propylene fraction is returned to the reaction stage.
The extractive distillation of propylene/propane mixtures is described in Advan. Chem. Ser. 1972, pages 16 to 34 as an alternative to simple distillation. Extraction media are, inter alia, acetone, furfural and nitriles such as acetonitrile, propionitrile, butyronitrile and benzo-nitrile. A feature of the extractive distillation is the influencing of the liquid/vapor equilibrium of the propylene/propane mixture by a suitable solvent in a similar manner to steam distillation. For industrial realization, a rectification column with evaporation at the bottom and reflux at the top is typical. In the method described, propane is taken off overhead. Propyl-ene is dissolved in the solvent and is isolated either in a second rectification stage or, if a miscibility gap is present, by phase separation. The authors conclude that - 21~649~
extractive distillation only has advantages over conven-tional distillation in special cases.
A further method uses molecular sieves to separate off propylene from propylene/propane mixtures of any composi-tion (DD-A-150,885). It is based on the fact that propyl-ene can penetrate into the zeolite pore structure and is adsorbed there, whereas propane is excluded from the diffusion, passes through the molecular sieve and arises at high purity. The propylene is thermally desorbed and is likewise obtained at high purity. The method iæ
suitable, in particular, for the separation of propylene/propane mixtures having a low propylene propor-tion. Yield-reducing attendant phenomena such as oligo-merization or coke formation are substantially excluded.
The known processes are only of limited applicability or they require complex measures which are not always economically justifiable. The object was therefore to develop a method which is technically simple and permits, in particular, in the case of industrial-scale produc-tion, the separation of propylene/propane mixtures withacceptable means. The method to be developed must be able to be carried out independently of the composition of the propylene/propane mixtures and also must be able to be carried out in the presence of accompanying substances due to the reaction. Moreover, it must be economical and, if required, fit into the sequence of a plurality of reaction stages without problem.
The invention achieves this object by a method for the separation of propylene/propane mixtures by selective absorption. It features the absorption medium used being water.
Surprisingly, propylene/propane mixtures can be separated into their components by the novel method in a simple manner and with the use of industrially conventional apparatuses. The absorption medium water is 213~96 environmentally tolerated and inexpensive and is also generally available in the required quality. Owing to the solubility ratios, it is discharged only in very small quantities together with the propane. The hydrocarbons are isolated at a purity which satisfies the requirements for most applications. hosses due to chemical conversions of the hydrocarbons do not occur.
According to the invention, the separation of propylene/-propane mixtures by the novel process is carried out by extraction with the aid of water in the quality conven-tionally available industrially. Drinking water, conden-sate or deionized or softened water or else process water of upstream or downstream process stages can be used.
Deionized water is preferably used.
According to a preferred embodiment of the method of the invention, phase transfer reagents (also termed solubili-zers or surfactants) are added to the aqueous phase. They modify the solution power for the two hydrocarbon com-ponents and as a result increase the separation effect.
The solubilizers which are known are compounds whose hydrophilic groups are ionic (anionic or cati~nic) or nonionic. The anionic compounds include sodium æalts, potassium salts or ~mmo~;um salts of carboxylic acids having 8 to 20 carbon atoms, in particular of saturated fatty acids having 12 to 18 carbon atoms, in addition alkylsulfates, alkylbenzenesulfonates and alkylbenzene-phosphates. Examples of cationic solubilizers are tetra-alkyl~mmo~;um salts and n-alkylpyridinium salts. The nonionic phase transfer reagents cannot dissociate into ions in aqueous solution. These include alkylpolyethylene glycols, alkylphenyl polyethylene glycols, fatty alkanol-amides and trialkylamine oxides. Finally, ampholytes such as aminocarboxylic acids, betaines and sulfobetaines are also used as solubilizers. In the context of the inven-tion ionic surfactants have proved to be particularlyuseful, including as cationic surfactants 213~496 trimethyltetradecyl~ ;um salts and anionic surfac-tants, including dodecylsulfonate.
Generally, the propylene/propane mixtures to be separated can be used in the form in which they arise in refineries or in processes performed in the chemical industry. In exceptional cases it can be necessary, prior to the separation of the hydrocarbon mixture, to remove consti-tuents interfering with or loading the absorption process such as products and by-products of preceding process stages which have not been separated off or only incom-pletely separated off.
To carry out the absorption, the gas mixture is intro-duced finely divided into the absorption medium and conducted in counter-current or else in co-current to the absorption medium spread out on a large surface area or sprayed. In the course of this, propylene preferentially enters through the phase boundary into the liquid and forms a mixed phase, whereas the carrier gas, that is to say the remaining components of the gas mixture, behave neutrally and as a result of their considerably lower solubility - compared with propylene - exit from the absorption medium virtually completely. The absorption is carried out in a single stage or multiple stages, discon-tinuously or continuously in the known absorption appara-tuses. Absorbers which are suitable are wash and spraytowers, plate columns, packed columns, wetted-wall absorbers, rotary washers and rotary columns. The absorp-tion is performed within broad temperature and pressure ranges. Temperatures between -5 and 90C are preferred, preferably 10 to 50C. The method can be carried out without applied pressure; elevated pressures up to about 5.0 MPa, in particular 4.0 to 5.0 MPa increase the absorption efficiency. In accordance with its solubility, in particular propylene is absorbed by the aqueous phase, whereas propane, together with any other inert gaseous components, exits undissolved from the absorption medium.
- ` 2136~g6 The number of the absorption stages used and thus the completeness of propylene absorption is dependent on the concentration of the propylene in the propylene/propane mixture. The absorption proceeds according to Henry's law and is dependent on the concentration of the hydrocarbons in the mixture. Therefore, the separation process must be terminated when more propane than propylene is absorbed by the water because of insufficient propylene concen-tration and high propane concentration.
The propylene dissolved in the absorption medium is desorbed in a known manner, eg. by heating, by pressure reduction or by expulsion with inert gas. The known measures can be employed individually, together or as a combination of two unit operations.
According to a particular embodiment of the method according to the invention, the propylene/propane mixture is conducted in counter-current to the water in a con-tinuous absorption column. The solution of propylene in water is then heated, it is depressurized in a desorption apparatus, the unsaturated hydrocarbon escaping is taken off and passed for further use. The low-propylene water arising in the bottom of tr~e desorption apparatus is likewise taken off, cooled, if required with utilization of the heat content, and returned to the absorption column. In accordance with the dependence of the amount of propylene absorbed on the propylene concentration in the gas mixture, the propane concentration in the propyl-ene separated off and the propylene concentration in the propane separated off can be adjusted to desired values by appropriate specification of the amount of water.
The novel method can be applied in all cases in which propylene and propane must be separated from each other.
This object is posed, e.g., in the hydroformylation of propylene, in which, inter alia, a propylene/propane mixture arises as off-gas. The specified procedure has proved to be useful, in particular, when heterogene~us catalysts, e.g. rhodium-phosphine complex compounds, dispersed in water are used, since the absorption medium water is also the reaction medium in the reaction of olefin with synthesis gas.
The example below describes the specified procedure in more detail, but does not restrict it to the embodiment given.
Example To the lower part of a counter-current absorption column cont~;n;ng 10 theoretical plates are fed per hour 1853 kg of a gas mixture which, in addition to other constitu-ents, contains 60% by mass of propylene and 22% by mass of propane and whose temperature is 51C. From the top of the absorption column which is operated at 4.0 MPa flow in counter-current to the gas mixture 130 m3 per hour of water at 10C as absorption medium. At the top of the absorption colnmn are taken off 586 kg per hour of a gas mixture which contains 53% by mass of propane and 1.3% by mass of propylene. At the bottom of the column the propylene-laden absorption medium is taken off, heated to 70C, fed to the to~ of a desorption column which is operated at 1.0 MPa and contains three theoretical stages and the mixture is depressurized. 30 kg per hour of synthesis gas at 15C are fed in at the bottom of the desorption column and, at the top, 1312 kg per hour of a gas mixture are taken off which contains 83% by mass of propylene and 8% by mass of propane. The water freed of propylene is cooled and returned to the absorption column. The propylene-rich gas can be utilized directly.
The separation of propylene/propane mixture i8 an object which is frequently required in refinery technology as in the chemical industry. Its aim is either the isolation of the pure hydrocarbons or else the recovery of one of the two components, in particular the propylene, eg. from off-gases.
Depending on the required purity at which the constitu-ents must be obtained from their mixtures, different methods are used. Thus, by the method of DE-A-3 412 336, the off-gas of propylene hydroformylation is partially condensed, it conventionally contains 25 to 40% by volume of propylene, 6 to 20% by volume of propane and, in addition, hydrogen and carbon monoxide, the condensate is rectified and the propylene fraction is returned to the reaction stage.
The extractive distillation of propylene/propane mixtures is described in Advan. Chem. Ser. 1972, pages 16 to 34 as an alternative to simple distillation. Extraction media are, inter alia, acetone, furfural and nitriles such as acetonitrile, propionitrile, butyronitrile and benzo-nitrile. A feature of the extractive distillation is the influencing of the liquid/vapor equilibrium of the propylene/propane mixture by a suitable solvent in a similar manner to steam distillation. For industrial realization, a rectification column with evaporation at the bottom and reflux at the top is typical. In the method described, propane is taken off overhead. Propyl-ene is dissolved in the solvent and is isolated either in a second rectification stage or, if a miscibility gap is present, by phase separation. The authors conclude that - 21~649~
extractive distillation only has advantages over conven-tional distillation in special cases.
A further method uses molecular sieves to separate off propylene from propylene/propane mixtures of any composi-tion (DD-A-150,885). It is based on the fact that propyl-ene can penetrate into the zeolite pore structure and is adsorbed there, whereas propane is excluded from the diffusion, passes through the molecular sieve and arises at high purity. The propylene is thermally desorbed and is likewise obtained at high purity. The method iæ
suitable, in particular, for the separation of propylene/propane mixtures having a low propylene propor-tion. Yield-reducing attendant phenomena such as oligo-merization or coke formation are substantially excluded.
The known processes are only of limited applicability or they require complex measures which are not always economically justifiable. The object was therefore to develop a method which is technically simple and permits, in particular, in the case of industrial-scale produc-tion, the separation of propylene/propane mixtures withacceptable means. The method to be developed must be able to be carried out independently of the composition of the propylene/propane mixtures and also must be able to be carried out in the presence of accompanying substances due to the reaction. Moreover, it must be economical and, if required, fit into the sequence of a plurality of reaction stages without problem.
The invention achieves this object by a method for the separation of propylene/propane mixtures by selective absorption. It features the absorption medium used being water.
Surprisingly, propylene/propane mixtures can be separated into their components by the novel method in a simple manner and with the use of industrially conventional apparatuses. The absorption medium water is 213~96 environmentally tolerated and inexpensive and is also generally available in the required quality. Owing to the solubility ratios, it is discharged only in very small quantities together with the propane. The hydrocarbons are isolated at a purity which satisfies the requirements for most applications. hosses due to chemical conversions of the hydrocarbons do not occur.
According to the invention, the separation of propylene/-propane mixtures by the novel process is carried out by extraction with the aid of water in the quality conven-tionally available industrially. Drinking water, conden-sate or deionized or softened water or else process water of upstream or downstream process stages can be used.
Deionized water is preferably used.
According to a preferred embodiment of the method of the invention, phase transfer reagents (also termed solubili-zers or surfactants) are added to the aqueous phase. They modify the solution power for the two hydrocarbon com-ponents and as a result increase the separation effect.
The solubilizers which are known are compounds whose hydrophilic groups are ionic (anionic or cati~nic) or nonionic. The anionic compounds include sodium æalts, potassium salts or ~mmo~;um salts of carboxylic acids having 8 to 20 carbon atoms, in particular of saturated fatty acids having 12 to 18 carbon atoms, in addition alkylsulfates, alkylbenzenesulfonates and alkylbenzene-phosphates. Examples of cationic solubilizers are tetra-alkyl~mmo~;um salts and n-alkylpyridinium salts. The nonionic phase transfer reagents cannot dissociate into ions in aqueous solution. These include alkylpolyethylene glycols, alkylphenyl polyethylene glycols, fatty alkanol-amides and trialkylamine oxides. Finally, ampholytes such as aminocarboxylic acids, betaines and sulfobetaines are also used as solubilizers. In the context of the inven-tion ionic surfactants have proved to be particularlyuseful, including as cationic surfactants 213~496 trimethyltetradecyl~ ;um salts and anionic surfac-tants, including dodecylsulfonate.
Generally, the propylene/propane mixtures to be separated can be used in the form in which they arise in refineries or in processes performed in the chemical industry. In exceptional cases it can be necessary, prior to the separation of the hydrocarbon mixture, to remove consti-tuents interfering with or loading the absorption process such as products and by-products of preceding process stages which have not been separated off or only incom-pletely separated off.
To carry out the absorption, the gas mixture is intro-duced finely divided into the absorption medium and conducted in counter-current or else in co-current to the absorption medium spread out on a large surface area or sprayed. In the course of this, propylene preferentially enters through the phase boundary into the liquid and forms a mixed phase, whereas the carrier gas, that is to say the remaining components of the gas mixture, behave neutrally and as a result of their considerably lower solubility - compared with propylene - exit from the absorption medium virtually completely. The absorption is carried out in a single stage or multiple stages, discon-tinuously or continuously in the known absorption appara-tuses. Absorbers which are suitable are wash and spraytowers, plate columns, packed columns, wetted-wall absorbers, rotary washers and rotary columns. The absorp-tion is performed within broad temperature and pressure ranges. Temperatures between -5 and 90C are preferred, preferably 10 to 50C. The method can be carried out without applied pressure; elevated pressures up to about 5.0 MPa, in particular 4.0 to 5.0 MPa increase the absorption efficiency. In accordance with its solubility, in particular propylene is absorbed by the aqueous phase, whereas propane, together with any other inert gaseous components, exits undissolved from the absorption medium.
- ` 2136~g6 The number of the absorption stages used and thus the completeness of propylene absorption is dependent on the concentration of the propylene in the propylene/propane mixture. The absorption proceeds according to Henry's law and is dependent on the concentration of the hydrocarbons in the mixture. Therefore, the separation process must be terminated when more propane than propylene is absorbed by the water because of insufficient propylene concen-tration and high propane concentration.
The propylene dissolved in the absorption medium is desorbed in a known manner, eg. by heating, by pressure reduction or by expulsion with inert gas. The known measures can be employed individually, together or as a combination of two unit operations.
According to a particular embodiment of the method according to the invention, the propylene/propane mixture is conducted in counter-current to the water in a con-tinuous absorption column. The solution of propylene in water is then heated, it is depressurized in a desorption apparatus, the unsaturated hydrocarbon escaping is taken off and passed for further use. The low-propylene water arising in the bottom of tr~e desorption apparatus is likewise taken off, cooled, if required with utilization of the heat content, and returned to the absorption column. In accordance with the dependence of the amount of propylene absorbed on the propylene concentration in the gas mixture, the propane concentration in the propyl-ene separated off and the propylene concentration in the propane separated off can be adjusted to desired values by appropriate specification of the amount of water.
The novel method can be applied in all cases in which propylene and propane must be separated from each other.
This object is posed, e.g., in the hydroformylation of propylene, in which, inter alia, a propylene/propane mixture arises as off-gas. The specified procedure has proved to be useful, in particular, when heterogene~us catalysts, e.g. rhodium-phosphine complex compounds, dispersed in water are used, since the absorption medium water is also the reaction medium in the reaction of olefin with synthesis gas.
The example below describes the specified procedure in more detail, but does not restrict it to the embodiment given.
Example To the lower part of a counter-current absorption column cont~;n;ng 10 theoretical plates are fed per hour 1853 kg of a gas mixture which, in addition to other constitu-ents, contains 60% by mass of propylene and 22% by mass of propane and whose temperature is 51C. From the top of the absorption column which is operated at 4.0 MPa flow in counter-current to the gas mixture 130 m3 per hour of water at 10C as absorption medium. At the top of the absorption colnmn are taken off 586 kg per hour of a gas mixture which contains 53% by mass of propane and 1.3% by mass of propylene. At the bottom of the column the propylene-laden absorption medium is taken off, heated to 70C, fed to the to~ of a desorption column which is operated at 1.0 MPa and contains three theoretical stages and the mixture is depressurized. 30 kg per hour of synthesis gas at 15C are fed in at the bottom of the desorption column and, at the top, 1312 kg per hour of a gas mixture are taken off which contains 83% by mass of propylene and 8% by mass of propane. The water freed of propylene is cooled and returned to the absorption column. The propylene-rich gas can be utilized directly.
Claims (6)
1. A method for the separation of propylene/propane mixtures by selective absorption, which comprises the absorption medium used being water.
2. The method as claimed in claim 1, wherein the absorption medium used is deionized water.
3. The method as claimed in claim 1 or 2, wherein a phase transfer compound is added to the water.
4. The method as claimed in claim 3, wherein the phase transfer compound is a trimethyltetradecylammonium salt or dodecylsulfonate.
5. The method as claimed in one or more of claims 1 to 4, wherein the absorption is carried out at tempera-tures between -5 and 90°C, preferably 10 to 50°C.
6. The method as claimed in one or more of claims 1 to 5, wherein the absorption is carried out at pressures up to about 5.0 MPa, in particular 4.0 to 5.0 MPa.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4340881.8 | 1993-12-01 | ||
| DE4340881A DE4340881A1 (en) | 1993-12-01 | 1993-12-01 | Process for the separation of propylene-propane mixtures |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2136496A1 true CA2136496A1 (en) | 1995-06-02 |
Family
ID=6503872
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002136496A Abandoned CA2136496A1 (en) | 1993-12-01 | 1994-11-23 | Method for the separation of propylene/propane mixtures |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0657406A1 (en) |
| JP (1) | JPH07206719A (en) |
| KR (1) | KR950017876A (en) |
| CA (1) | CA2136496A1 (en) |
| DE (1) | DE4340881A1 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10031517A1 (en) * | 2000-06-28 | 2002-01-10 | Basf Ag | Hydroformylation of olefins to produce aldehydes is integrated with thermal and/or catalytic cracking and/or dehydrogenation of hydrocarbon charge, and uses olefin-enriched stream from separator and recycling |
| DE10031519A1 (en) * | 2000-06-28 | 2002-01-10 | Basf Ag | Process for the hydroformylation of olefins having 2 to 8 carbon atoms, I |
| US6730142B2 (en) * | 2002-03-19 | 2004-05-04 | Exxonmobil Research And Engineering Company | Separation of propylene from hydrocarbon mixtures |
| JP5807945B2 (en) * | 2010-06-21 | 2015-11-10 | 住友精化株式会社 | Propane purification method and purification apparatus |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR833655A (en) * | 1937-06-30 | 1938-10-27 | Melle Usines Sa | Process for separating olefins from gas mixtures |
-
1993
- 1993-12-01 DE DE4340881A patent/DE4340881A1/en not_active Withdrawn
-
1994
- 1994-11-23 CA CA002136496A patent/CA2136496A1/en not_active Abandoned
- 1994-11-23 EP EP94118397A patent/EP0657406A1/en not_active Withdrawn
- 1994-11-24 KR KR1019940030994A patent/KR950017876A/en not_active Application Discontinuation
- 1994-11-25 JP JP6291803A patent/JPH07206719A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE4340881A1 (en) | 1995-06-08 |
| KR950017876A (en) | 1995-07-20 |
| JPH07206719A (en) | 1995-08-08 |
| EP0657406A1 (en) | 1995-06-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Dead |