CA1091615A - Use of n-methyl-morpholine-3-one in the extractive distillation of hydrocarbons - Google Patents
Use of n-methyl-morpholine-3-one in the extractive distillation of hydrocarbonsInfo
- Publication number
- CA1091615A CA1091615A CA269,662A CA269662A CA1091615A CA 1091615 A CA1091615 A CA 1091615A CA 269662 A CA269662 A CA 269662A CA 1091615 A CA1091615 A CA 1091615A
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- Prior art keywords
- extractive distillation
- column
- distillation column
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- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G21/00—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents
- C10G21/06—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents characterised by the solvent used
- C10G21/12—Organic compounds only
- C10G21/20—Nitrogen-containing compounds
-
- 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
- C07C7/08—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds by extractive 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
- C07C7/11—Purification; Separation; Use of additives by absorption, i.e. purification or separation of gaseous hydrocarbons with the aid of liquids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G21/00—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents
- C10G21/06—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents characterised by the solvent used
- C10G21/12—Organic compounds only
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P30/00—Technologies relating to oil refining and petrochemical industry
- Y02P30/40—Ethylene production
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Water Supply & Treatment (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Extraction Or Liquid Replacement (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE:
The invention is concerned with a method of separating a diolefin from a mixture thereof with other hydrocarbons by an extractive distillation. The method of the invention comprises feeding a stream of the mixture of hydrocarbons to a first extractive distillation column, feeding a stream of solvent comprised of N-methyl-morpholine-3-one to the first extractive distillation column, withdrawing the other hydrocarbons and a minor quantity of the diolefin from the head of the first extractive distillation column, recovering the solvent and the balance of the diolefin from the first extractive distillation column as bottom product, feeding the bottom product from the first extractive distillation column to a second extractive dis-tillation column, recovering the diolefin in the bottom product of the first extractive distillation column from the second extractive distillation column as head product, withdrawing the solvent in the bottom product of the first extractive distilla-tion column from the second extractive distillation column as bottom product, and recycling the bottom product from the second extractive distillation column to the first extractive distilla-tion column. The method of the invention is particularly use-ful for the separation of butadiene from a mixture of C4 hydro-carbons, or of isoprene from a mixture of C5 hydrocarbons.
The invention is concerned with a method of separating a diolefin from a mixture thereof with other hydrocarbons by an extractive distillation. The method of the invention comprises feeding a stream of the mixture of hydrocarbons to a first extractive distillation column, feeding a stream of solvent comprised of N-methyl-morpholine-3-one to the first extractive distillation column, withdrawing the other hydrocarbons and a minor quantity of the diolefin from the head of the first extractive distillation column, recovering the solvent and the balance of the diolefin from the first extractive distillation column as bottom product, feeding the bottom product from the first extractive distillation column to a second extractive dis-tillation column, recovering the diolefin in the bottom product of the first extractive distillation column from the second extractive distillation column as head product, withdrawing the solvent in the bottom product of the first extractive distilla-tion column from the second extractive distillation column as bottom product, and recycling the bottom product from the second extractive distillation column to the first extractive distilla-tion column. The method of the invention is particularly use-ful for the separation of butadiene from a mixture of C4 hydro-carbons, or of isoprene from a mixture of C5 hydrocarbons.
Description
l~g~lS
l~he presellt invention relates to a method o$ separating a diolefin from a mixture of hydroearbons eontaining the diolefin and other hydrocarbons by an extraetive distillation.
More particularly, the invention is directed to the separation of a diolefin, such as butadiene or isoprene, from a mixture thereof with other hydroearbons by an extractive distil-lation wherein the solvent employed comprises N-methyl-morpho-line-3-one.
It is known to utilize heterocyclic compounds as extractive solvents in the separation of hydrocarbons from hydrocarbon-aeeous mixtures by operations oE extraetive distillation, gas-liquid scrubbing or liquid-liquid scrubbing.
When evaluating such compounds to the end of an industrial exploitation of same, numerous aspects must be considered, among which selectivity, conveyance power, stability, ease of synthe-sis, toxicity, vapor pressure, specific gravity, boiling point temperature, melting point temperature and others.
It has been found that N-methyl-morpholine-3-one is a com-pound whieh satisEactorily fulfils, in general, all o these requirements and thus it can be used with advantage as an extraetiv~ solvent.
~ he present invention thereEore provicles a me~hod oE
separating a diolefin from a mixture thereoE with other hydro-earbons by an extractive distillation, which eomprises Eeecling a stream of the mixture of hydrocarbons to a Eirst extractive distillation column, feeding a stream of solvent comprised of N-methyl-morpholine-3-one to the Lirs~ extractive distillation column, withdrawing the other hytirocarbons and a minor quantity of the diolefin from the head of the first extractive distilla-tion column, recovering the solvent and the balance of theclioleEin Erom the first extractive distillation column as bot-
l~he presellt invention relates to a method o$ separating a diolefin from a mixture of hydroearbons eontaining the diolefin and other hydrocarbons by an extraetive distillation.
More particularly, the invention is directed to the separation of a diolefin, such as butadiene or isoprene, from a mixture thereof with other hydroearbons by an extractive distil-lation wherein the solvent employed comprises N-methyl-morpho-line-3-one.
It is known to utilize heterocyclic compounds as extractive solvents in the separation of hydrocarbons from hydrocarbon-aeeous mixtures by operations oE extraetive distillation, gas-liquid scrubbing or liquid-liquid scrubbing.
When evaluating such compounds to the end of an industrial exploitation of same, numerous aspects must be considered, among which selectivity, conveyance power, stability, ease of synthe-sis, toxicity, vapor pressure, specific gravity, boiling point temperature, melting point temperature and others.
It has been found that N-methyl-morpholine-3-one is a com-pound whieh satisEactorily fulfils, in general, all o these requirements and thus it can be used with advantage as an extraetiv~ solvent.
~ he present invention thereEore provicles a me~hod oE
separating a diolefin from a mixture thereoE with other hydro-earbons by an extractive distillation, which eomprises Eeecling a stream of the mixture of hydrocarbons to a Eirst extractive distillation column, feeding a stream of solvent comprised of N-methyl-morpholine-3-one to the Lirs~ extractive distillation column, withdrawing the other hytirocarbons and a minor quantity of the diolefin from the head of the first extractive distilla-tion column, recovering the solvent and the balance of theclioleEin Erom the first extractive distillation column as bot-
2 - ~.
1()91~l5 tom product, feeding the bottom product Erom the irst extractive distillation column to a second extractive distilla-tion column, recovering the dioleEin in the bottom product of the first extractive distillation column from the second extractive distillation column as head product, withdrawing the solvent in the bottom product of the first extractive distillation column from the second extractive distillation column as bottom product, and recycling the bottom product from the second extractive distillation column to the first extractive distillation column.
The N-methyl-morpholine-3-one can be used either alone or in a mixture with up to 20 ~ by weight of water or other organic solvents, such as ethylene glycol.
The method of the invention is particularly useful for the separation oE butadiene from a mixture of C4 hydrocarbons, or of isoprene Erom a mixture of C5 hydrocarbons.
The following non-restrictive examples illustrate the invention.
~XAMl~L~ 1 .
2Q With reference to the diagram of FIGURE 1, the extractive distillation column 9 is Eed with a stream which is composed by (line 1):
Isoprene282.0 mols/hour Isopentane 13.2 l-pentene 39.7 2-methyl-1-butene 67.3 nor. pentane 120.]
2-uentene-trans 29.4 " "
2-pentene-iso 18.1 " "
2-methyl-2-butene 11.3 " "
1,3-cyclopentadiene1.7 " "
,!lt-.~';
Isopropenylacetylene 0.1 " "
The workin~ conditions are as follows:
Head pressure 1.1 absolute atmospheres L/D O.g No. of plates 65 .-~ - 3~ -~as~6l~
The same column is fed through the line 2 with 500 kgs/hr of a mixture composed by N-methyl-morpholine-3-one/water in the proportion of 94 to 6 by weight.
From the head (line 3) a stream is dumped which is com-posed by :
Isoprene 5.6 mols/hr Isopentane 13.2 " "
l-pentene 39.7 2-methyl-1-butene 67-3 nor.pentane 12001 2-pentene-trans 29.4 " "
2-pentene-cis 11.1 " ~' 2-methyl-2-bu-tene 11.0 The stream coming from the bottom of column 9 (line 4) is sent to the second extractive distillation column 10~ along with a stream of 60 kgs/hr (line 5) o-f the above indicated solvent.
The col-~n 10 is operated under the following conditions:
Head pressure 1~1 abs~ atmospheres L/D 0.9 No. o~ plates 75 From the head (line 6) is discharged a stream oE high-purity ~soprene~ which is particularly composed by .
lsoprene 270.8 mols/hr 2-methyl-2-butene 0.3 While from a lateral draw in vapor phase (line 7) the more polar hydrocarbons (1~3-cyclopentadien~ and isopropenyl acetylene) are discharged, from the bottom (line 8) the solvent is dumped, which is exempt from hydrocarbons and is thus adapted to be re-cycled in the abovementioned extractive distillation columns 9 and 10.
With reference to the diagram according to FIGURE 1~ the 4.
109~
extractive distillation column 9 is fed with a 1 kg/hr stream composed by (line 1) :
C~ saturated hydrocarbons 20% by weight C4 olefinic hydrocarbons 45% " "
1~3-butadiene 35% " "
Acetylene compound (such as vinylacetylene)1~000 ppm " "
The working conditions are as follows :
Head pressure 4 abs. atmospheres L/D o.9 No. of plates 70 To the same column, through the line 2~ are sent 10 kg/hr oE a mixture composed by N-methyl-l-morpholine-3-one and water in the propor-tion of 93/7 by weight.
From the head (line 3) a stream is discharged, oE o.65 kg/hr which substantially contains saturated and oleEinic hydrocarbons.
The stream coming from the bottom of the column 9 (line 4) is sent to the second extraction column 10~ together with a stream of 2 kg/hr (line 5) of the abovementioned solvent .
The separa-tion in the column 10 is carried out under the Eollowing conditions :
Head pressure 1.2 abs. atmospheres L/D 0.9 No. oE plates 80 From the head is discharged (line 6) a stream oE about 0.34 kg/hr oE 1~3-butadiene with a high degree of purity and which con-tains~ more particularly~ about 20 ppm (parts per million) of acetylene compounds.
From a lateral draw in vapor phase (line 7) are discharged the acetylene hydrocarbons together with a negligible quantity of butadiene, whereas from the bottom is discharged (line 8) the solvent~ which is hydrocarbon-free, and which is adapted to be 5.
l61~5 reused in the extraction columns 9 and 10 aforementioned.
EXAMPLE
With reference to the diagram according to FIGURE 2~ the extractive distillation column 8 is Eed with a reformed ~asoline stream composed by (line 1) :
Benzene 1050 kg/hr Toluene 2.00 Xylenes 3.50 1l "
Nonaromatics 3.oo The operative conditions are as follows :
Head pressure 1.1 abs. atmospheres L/D 0.7 No. o plates 55 The same column is Eed through the line 2 with 30 ~g/hr of a mixture of N-methyl-morpholine-3-one and monoethylene glycol in the proportion of 95/5 parts by weight.
From the head (line 3) is discharged a stream of 3.05 kg/hr which substantially contains all the nonaromatic hydroçarbons Eed to the same column 8.
The bottom product is sent (line 4) to a stripping column (9) which is operated under the following conditions :
Head pressure 0.2 abs. atmosphere L/D 0.2 No. oE plates 25 From the head (line 5) there is obtained a stream of aromatic hydrocarbons having a preselected quantity of saturated compounds whereas from the bottom the solvent is recovered~ which is required for the operation oE the column (8) .
The stripping of the stream discharged from the bottom of the column 8 can also carried out in two stages, as indicated by the diagram according to FIGURE 3 6.
s In such a case~ the same bottom product (line 4) is sent to a first stripping column (9) which is operated under the following conditions :
Head pressure 1.1 atmospheres L/D 0.2 No. of plates 25 From the head (line 5) is obtained a stream having a speci-fied contents of saturated compounds and which is composed by :
Benzene 1.49 kg/hr Toluene 1.99 " "
Xylenes 0.47 " "
From the bottom (line 6) is discharged a stream which is sent to a second stripping column (10) which is operated under the following conditions :
Pressure 0.2 abs. atmosphere L/D 0.1 No. of plates 15 While from the head (line 7) is discharged a stream of xy~enes according to a preselected specification (3.03 kg/hr)~
Erom the bottom is recovered the solvent which is required for the operation oE the column (8).
EXAMPLE~
~ ith reference to the diagram according to FIGURE 4~ the c~tractive clistillation column (9) is fecl with a stream (line l) of 100 kg/hr oE a C8 cut having the Eollowing composition :
C8 saturated and oleEinic hydrocarbons 3.5%
o-xylene 17.0%
m-xylene and p-xylene43.1%
ethylbenzene 8.6%
styrene 27.8%
7.
109~
The operative conditions are as follows :
Head pressure 140 mmHg (absolute) No. o~ plates 80 The same column is fed through the line 2 with 1,300 kg/hr of a mixture composed by N-methyl-morpholine-3-one and water in the ratio of 96/4 by weight.
From the head (line 3) is discharged water and a stream of organic refined mixture composed by :
C8 saturated and ole~inic hydrocarbons 3.5 kg/hr o-xylene 16.9 m-xylene and p-xylene 43.1 1~ "
ethylbenzene 8.6 " "
styrene o.3 ll ll This stream is sent to a demixer (11) to separated water (17) from the refined mixture (16).
From the tail is discharged a stream (line 4) which is sent to the e~traction column (lO) together with a stream of 150 kg/hr of the solvent aforesaid. The separation in the latter column is carried out under the following conditions :
Head pressure 160 mmHg (abs) L/0 2~5 No. o-~ plates 60 From the head (line 6~ a stream is removed which comprises o-~ylene and styrene which is recyc.led to the column (9)~ whereas ~roln the bottom is discharged a stream (7) which is fed to the stripping column (12).
Such stripping column is operated under the f:ollowing con-0 ditiolls :Head pressure 190 mmHg (abs) No. of plates 30 ~g~61~
From the head is discharged a stream which is sent to the demixer 13: from the line ~ is obtained styrene having a purity of more than 99.8%.
From the tail of the same column the solvent is discharged, which, upon having been admixed at 15 with tempered water from 17 and 18, is recycled.
With reference to -the diagram according to FIGURE 5, the gas-liquid scrubbing column (9) is fed with a s-tream o l kg/hr composed by :
C4 saturated hydrocarbons about 20~ by wt.
C4 olefinic hydrocarbons about 45% by wt.
The operative conditions are as follows :
Head pressure 5 abs atmospheres No. of plates 40 The same column is fed through the line 2 with about 8.5 kg/hr of a mixture composed by N-methyl-morphol.ine-3-one and water in the proportion of 94/6 by weight.
From the head (line 3) is discharged a gas stream of o.65 kg/hr which substantially contain saturated and olefinic hydro-carbons~ whereas the bot-tom stream (line 4) is sent to the strip-ping column (10).
The operation o~ the latter column is characterized b~ :
Head pressure 5.5 abs. atmospheres No. o~ plates 45 From the head (line 5) is discharged a gas stream of C4 ole-~l~s and 1~3-butadiene which is recycled to the column (9)~ where-as ~rom the bottom is discharged a stream (6) which is fed to the second stripping column (ll)o The la-tter column is operated under 30the following conditions :
Head pressure 1~1 abs. atmospheres No. of plates 30 10~6~LS
The gaseous stream discharged from the head is sent to the compressor (12~. From the line (8), upon condensation~ are drawn about 0.35 kg/hr o~ 1~3-butadiene according to specification containing saturated and olefinic compounds ( purity more than 99.5% by wt.), whereas through the line (7) fractions of the afore-mentioned stream are recycled to the column (10).
From the tail of (ll) the solvent is recovered, which is re-used in the column (9).
With reference to the diagram according to FIGURE 6~ the charge which is used (line l) is a gasoline having the following composition :
benzene 15% by wt.
toluene 25% " ~' xylenes 25% " "
saturated 35~ " ll This charge is fed to the liquid-liquid extraction column (14) having 60 plates~ at the rate of flow of 5 kg/hr. Through the line t13) are sent 13 kg/hr of a mixture of N-methyl-morpholine-
1()91~l5 tom product, feeding the bottom product Erom the irst extractive distillation column to a second extractive distilla-tion column, recovering the dioleEin in the bottom product of the first extractive distillation column from the second extractive distillation column as head product, withdrawing the solvent in the bottom product of the first extractive distillation column from the second extractive distillation column as bottom product, and recycling the bottom product from the second extractive distillation column to the first extractive distillation column.
The N-methyl-morpholine-3-one can be used either alone or in a mixture with up to 20 ~ by weight of water or other organic solvents, such as ethylene glycol.
The method of the invention is particularly useful for the separation oE butadiene from a mixture of C4 hydrocarbons, or of isoprene Erom a mixture of C5 hydrocarbons.
The following non-restrictive examples illustrate the invention.
~XAMl~L~ 1 .
2Q With reference to the diagram of FIGURE 1, the extractive distillation column 9 is Eed with a stream which is composed by (line 1):
Isoprene282.0 mols/hour Isopentane 13.2 l-pentene 39.7 2-methyl-1-butene 67.3 nor. pentane 120.]
2-uentene-trans 29.4 " "
2-pentene-iso 18.1 " "
2-methyl-2-butene 11.3 " "
1,3-cyclopentadiene1.7 " "
,!lt-.~';
Isopropenylacetylene 0.1 " "
The workin~ conditions are as follows:
Head pressure 1.1 absolute atmospheres L/D O.g No. of plates 65 .-~ - 3~ -~as~6l~
The same column is fed through the line 2 with 500 kgs/hr of a mixture composed by N-methyl-morpholine-3-one/water in the proportion of 94 to 6 by weight.
From the head (line 3) a stream is dumped which is com-posed by :
Isoprene 5.6 mols/hr Isopentane 13.2 " "
l-pentene 39.7 2-methyl-1-butene 67-3 nor.pentane 12001 2-pentene-trans 29.4 " "
2-pentene-cis 11.1 " ~' 2-methyl-2-bu-tene 11.0 The stream coming from the bottom of column 9 (line 4) is sent to the second extractive distillation column 10~ along with a stream of 60 kgs/hr (line 5) o-f the above indicated solvent.
The col-~n 10 is operated under the following conditions:
Head pressure 1~1 abs~ atmospheres L/D 0.9 No. o~ plates 75 From the head (line 6) is discharged a stream oE high-purity ~soprene~ which is particularly composed by .
lsoprene 270.8 mols/hr 2-methyl-2-butene 0.3 While from a lateral draw in vapor phase (line 7) the more polar hydrocarbons (1~3-cyclopentadien~ and isopropenyl acetylene) are discharged, from the bottom (line 8) the solvent is dumped, which is exempt from hydrocarbons and is thus adapted to be re-cycled in the abovementioned extractive distillation columns 9 and 10.
With reference to the diagram according to FIGURE 1~ the 4.
109~
extractive distillation column 9 is fed with a 1 kg/hr stream composed by (line 1) :
C~ saturated hydrocarbons 20% by weight C4 olefinic hydrocarbons 45% " "
1~3-butadiene 35% " "
Acetylene compound (such as vinylacetylene)1~000 ppm " "
The working conditions are as follows :
Head pressure 4 abs. atmospheres L/D o.9 No. of plates 70 To the same column, through the line 2~ are sent 10 kg/hr oE a mixture composed by N-methyl-l-morpholine-3-one and water in the propor-tion of 93/7 by weight.
From the head (line 3) a stream is discharged, oE o.65 kg/hr which substantially contains saturated and oleEinic hydrocarbons.
The stream coming from the bottom of the column 9 (line 4) is sent to the second extraction column 10~ together with a stream of 2 kg/hr (line 5) of the abovementioned solvent .
The separa-tion in the column 10 is carried out under the Eollowing conditions :
Head pressure 1.2 abs. atmospheres L/D 0.9 No. oE plates 80 From the head is discharged (line 6) a stream oE about 0.34 kg/hr oE 1~3-butadiene with a high degree of purity and which con-tains~ more particularly~ about 20 ppm (parts per million) of acetylene compounds.
From a lateral draw in vapor phase (line 7) are discharged the acetylene hydrocarbons together with a negligible quantity of butadiene, whereas from the bottom is discharged (line 8) the solvent~ which is hydrocarbon-free, and which is adapted to be 5.
l61~5 reused in the extraction columns 9 and 10 aforementioned.
EXAMPLE
With reference to the diagram according to FIGURE 2~ the extractive distillation column 8 is Eed with a reformed ~asoline stream composed by (line 1) :
Benzene 1050 kg/hr Toluene 2.00 Xylenes 3.50 1l "
Nonaromatics 3.oo The operative conditions are as follows :
Head pressure 1.1 abs. atmospheres L/D 0.7 No. o plates 55 The same column is Eed through the line 2 with 30 ~g/hr of a mixture of N-methyl-morpholine-3-one and monoethylene glycol in the proportion of 95/5 parts by weight.
From the head (line 3) is discharged a stream of 3.05 kg/hr which substantially contains all the nonaromatic hydroçarbons Eed to the same column 8.
The bottom product is sent (line 4) to a stripping column (9) which is operated under the following conditions :
Head pressure 0.2 abs. atmosphere L/D 0.2 No. oE plates 25 From the head (line 5) there is obtained a stream of aromatic hydrocarbons having a preselected quantity of saturated compounds whereas from the bottom the solvent is recovered~ which is required for the operation oE the column (8) .
The stripping of the stream discharged from the bottom of the column 8 can also carried out in two stages, as indicated by the diagram according to FIGURE 3 6.
s In such a case~ the same bottom product (line 4) is sent to a first stripping column (9) which is operated under the following conditions :
Head pressure 1.1 atmospheres L/D 0.2 No. of plates 25 From the head (line 5) is obtained a stream having a speci-fied contents of saturated compounds and which is composed by :
Benzene 1.49 kg/hr Toluene 1.99 " "
Xylenes 0.47 " "
From the bottom (line 6) is discharged a stream which is sent to a second stripping column (10) which is operated under the following conditions :
Pressure 0.2 abs. atmosphere L/D 0.1 No. of plates 15 While from the head (line 7) is discharged a stream of xy~enes according to a preselected specification (3.03 kg/hr)~
Erom the bottom is recovered the solvent which is required for the operation oE the column (8).
EXAMPLE~
~ ith reference to the diagram according to FIGURE 4~ the c~tractive clistillation column (9) is fecl with a stream (line l) of 100 kg/hr oE a C8 cut having the Eollowing composition :
C8 saturated and oleEinic hydrocarbons 3.5%
o-xylene 17.0%
m-xylene and p-xylene43.1%
ethylbenzene 8.6%
styrene 27.8%
7.
109~
The operative conditions are as follows :
Head pressure 140 mmHg (absolute) No. o~ plates 80 The same column is fed through the line 2 with 1,300 kg/hr of a mixture composed by N-methyl-morpholine-3-one and water in the ratio of 96/4 by weight.
From the head (line 3) is discharged water and a stream of organic refined mixture composed by :
C8 saturated and ole~inic hydrocarbons 3.5 kg/hr o-xylene 16.9 m-xylene and p-xylene 43.1 1~ "
ethylbenzene 8.6 " "
styrene o.3 ll ll This stream is sent to a demixer (11) to separated water (17) from the refined mixture (16).
From the tail is discharged a stream (line 4) which is sent to the e~traction column (lO) together with a stream of 150 kg/hr of the solvent aforesaid. The separation in the latter column is carried out under the following conditions :
Head pressure 160 mmHg (abs) L/0 2~5 No. o-~ plates 60 From the head (line 6~ a stream is removed which comprises o-~ylene and styrene which is recyc.led to the column (9)~ whereas ~roln the bottom is discharged a stream (7) which is fed to the stripping column (12).
Such stripping column is operated under the f:ollowing con-0 ditiolls :Head pressure 190 mmHg (abs) No. of plates 30 ~g~61~
From the head is discharged a stream which is sent to the demixer 13: from the line ~ is obtained styrene having a purity of more than 99.8%.
From the tail of the same column the solvent is discharged, which, upon having been admixed at 15 with tempered water from 17 and 18, is recycled.
With reference to -the diagram according to FIGURE 5, the gas-liquid scrubbing column (9) is fed with a s-tream o l kg/hr composed by :
C4 saturated hydrocarbons about 20~ by wt.
C4 olefinic hydrocarbons about 45% by wt.
The operative conditions are as follows :
Head pressure 5 abs atmospheres No. of plates 40 The same column is fed through the line 2 with about 8.5 kg/hr of a mixture composed by N-methyl-morphol.ine-3-one and water in the proportion of 94/6 by weight.
From the head (line 3) is discharged a gas stream of o.65 kg/hr which substantially contain saturated and olefinic hydro-carbons~ whereas the bot-tom stream (line 4) is sent to the strip-ping column (10).
The operation o~ the latter column is characterized b~ :
Head pressure 5.5 abs. atmospheres No. o~ plates 45 From the head (line 5) is discharged a gas stream of C4 ole-~l~s and 1~3-butadiene which is recycled to the column (9)~ where-as ~rom the bottom is discharged a stream (6) which is fed to the second stripping column (ll)o The la-tter column is operated under 30the following conditions :
Head pressure 1~1 abs. atmospheres No. of plates 30 10~6~LS
The gaseous stream discharged from the head is sent to the compressor (12~. From the line (8), upon condensation~ are drawn about 0.35 kg/hr o~ 1~3-butadiene according to specification containing saturated and olefinic compounds ( purity more than 99.5% by wt.), whereas through the line (7) fractions of the afore-mentioned stream are recycled to the column (10).
From the tail of (ll) the solvent is recovered, which is re-used in the column (9).
With reference to the diagram according to FIGURE 6~ the charge which is used (line l) is a gasoline having the following composition :
benzene 15% by wt.
toluene 25% " ~' xylenes 25% " "
saturated 35~ " ll This charge is fed to the liquid-liquid extraction column (14) having 60 plates~ at the rate of flow of 5 kg/hr. Through the line t13) are sent 13 kg/hr of a mixture of N-methyl-morpholine-
-3-one and water in the ratio of 95/5 by weight~ the entire column being maintained at 40C-45C (head pressure about 2 atmospheres absolute).
From khe head of the column (line 3) i~ discharged a stream which ls ess~ntially composed by the saturated compounds which were present in the original charge.
The extract emerging Erom the bottom is Eed to the head of the column 15 (head pressure about 1.2 atmosphere absolute)0 No.
o~ plates = 30).
The head pressure of the column 15 (line 5) is condensed in two consecutive stages at (17) and (18). The stream (6) condensed above 120C is remixed to the charge whereas the stream (7) is re-10.
lS
cycled to the base of the liquid-liquid extractor.
The stream as discharged from the bot-tom of the column (15) (line 8) is sent to the column (16)~ (head pressure = 1.2 abs. atm., 30 plates)~
From the head is discharged a stream which is demixed at (9): from the line 10 is drawn a stream of about 3.05 kg/hr of aromatics having a specified contents of saturated compounds, whereas from the bottom of the demixer is drawn an aqueous stream which is par~.ly re-fluxed to the same column (16, 1.5 kg/hr) and partly is recycled to the column 14 ( 0.7 kg/hr)~ The solvent discharged from the bottom of (10) is re-used in the same liquid-liquid extractor.
EX~MPLE 7 With reference to the symbolic diagram of FIGURE 7~ the charge which is used (line l) is a reforming gasoline having the following composition :
benzene 4% by weight toluene 15% " "
xylenes 20% " "
saturated 61% " "
This charge is sent -to a first liquid-liquid extraction column (12) which has 40 plates~ at a rate of Plow of 100 kg/hr.
Through thè line (S) are sent about 250 kg/hr of N-methyl-morpho-line-3-one~ whereas through the line (10) are sent to the same column 40 kg/hr oP pen-tane~ the extractor being maintained at 25C
(head pressure = 3 atmospheres abso:lute).
The stream discharged from the head (line 2) is sent to the distillation column (13) whereas from the hea~ thereof (line 8) the pentane is recovered which is required for the operation of the extractor~ from the bottom (line 9) is discharged a stream of about 61~3 kg/hr composed essen-tially by the saturated hydrocarbons which were contained in the original charge (l).
lOg~61S
The bottom stream o the extractor (12) is sent to the second liquid-liquid extractor (14) together with about 220 kg/hr of pentane (line 11): this column is consti~uted by 20 plates and operates constantly at 25C and 2.0 atmospheres absclute.
The stream discharged from the head (line 4) is sent to the distillation column (15- whereas from the head thereof (line 6) is recovered the pentane which is necessary for operating the extractor~ from the bottom (line 7) is discharged a stream of about 38,7 kg/hr of a mixture of benzene~ toluene and xylene having a specified percentage o~ saturated compounds.
From the bottom of the second extractor is recovered the solvent which is used at 12.
With reference to the diagram according -to FIGURE 8, the liquid-liquid extraction column (12) is fed with a stream equal to that already disclosed in Example 1.
The same column (formed by 50 plates and working at a pressure of 1.2 atmosphere absolute) is fed~ through the line 7~ also with 150 kg/hr of a mixture composed by N-methyl-morpholine-3-one and water in the proportion of 95/5 by weightO
From the head (line 2) a stream is discharged which~ upon stripping of the solvent contained therein (an operation which i9 not shown in the drawing)~ is composed by :
isoprene 8,4 isopentan~ 13,2 l-pentene 39.7 2-methyl-1-butene 67-3 nor.pentane 120.1 2-pentene-trans 29~4 . 2-pentene-cis 18.1 2-methyl-2-bu-tene 10.8 The stream discharged from the bottom (line 3) is fed -to the lQ~ S
stripping column (13) (head pressure about 1.5 atm.abs.~ 30 plates).
From the he~d (line 4) is discharged a stream of olefins and isoprene, which is recycled to the extrac~or~ whereas from the bottom is discharged a stream (5) which is -fed to the second stripping column (14) (head pressure about 1.2 atm.abs.~ 20 plates~
L/D = 0.2).
From the line (6) is recovered isoprene having a speci~ied contents o~ olefins and sa-turated compounds, which is sent to the extractive distillation column (ll) for removing the polar hy~ro-carbons~ whereas from the line (7) is recovered the solvent which is necessary to operate the column (12)~
The column (12) is operated under the following conditions :
Head pressure 1.1 abs. atm~
L/D 0.9 No. of plates 75 From the head (line 8) is discharged a stream of highly pure lsoprene~ which~ more particularly~ is composed by :
isoprene 268.o mols/hr 2-methyl-2-butene o 5 l~ ~t While Erom the lateral draw in vapor phase (line 9) are dischargecI-the most polar hydrocarbons ( 1~3-cyclopentadiene and iso-propyl-acetylene), from the bottom is discharged (line 10) the 001vont~ which is exempt from hydrocarbons and thus adapted to be r~-used in -the same column 11, ~X~IPLE 9 With reference to the diagram according to FIGURE 5 a the gas-liquid scrubbing column (9) is fed with a stream constituted by :
nor.butane 89.5 mols/hr isobutane 2204 " "
13.
L6i5 l-butene 285 o2 mols/hr 2-butene-trans 117.6 " "
2~butene-cis 91.0 " "
1~3-butadiene 6.8 " "
The working conditions are as ~ollows :
head pressure 5 atm.abs.
No. of plates 40 The same column is fed~ through the line 2, with 1,200 kg/hr of a mixture constituted by N-methyl-morpholine-3-one and water in the proportion oE 93/7 by weight.
The bottom stream (line 4) is sent to the first stripping column (10)~ whereas from the head is discharged a gas stream composed by :
nor.butane 87.7 mols/hr isobutane 22.4 " ~
l-butene 5.7 " "
The operation of the column (10) is characterized by :
head pressure S.S atm.abs.
No. of plates ~0 From the head is discharged a gaseous s-tream of olefin~s and saturated C4 which is recycled to the column (9)~ whereas frcm the bottom is discharged a stream (6) which is ~ed to -the second stripping column (11).
The latter column is operatecl under the ~`ollowing conditions:
head pressure 1.1 abs~atm.
No. o~ plates 30 The gaseous stream is sent to the compressor (12); from the line (8), upon condensation, a stream is drawn which is composed by :
nor.butene 1.8 mols/hr l-butene 279-5 "
2-butene-trans 117.6 " "
14.
~1615 2-butene-cis 91~0 mols/hr 1~3-butadiene 6.8 A portion of the abovementioned stream sent to the com-pressor is recycled through the line (7) to the column (10).
From the tail (11) the solvent is recovered which is re-used in the column (9).
From khe head of the column (line 3) i~ discharged a stream which ls ess~ntially composed by the saturated compounds which were present in the original charge.
The extract emerging Erom the bottom is Eed to the head of the column 15 (head pressure about 1.2 atmosphere absolute)0 No.
o~ plates = 30).
The head pressure of the column 15 (line 5) is condensed in two consecutive stages at (17) and (18). The stream (6) condensed above 120C is remixed to the charge whereas the stream (7) is re-10.
lS
cycled to the base of the liquid-liquid extractor.
The stream as discharged from the bot-tom of the column (15) (line 8) is sent to the column (16)~ (head pressure = 1.2 abs. atm., 30 plates)~
From the head is discharged a stream which is demixed at (9): from the line 10 is drawn a stream of about 3.05 kg/hr of aromatics having a specified contents of saturated compounds, whereas from the bottom of the demixer is drawn an aqueous stream which is par~.ly re-fluxed to the same column (16, 1.5 kg/hr) and partly is recycled to the column 14 ( 0.7 kg/hr)~ The solvent discharged from the bottom of (10) is re-used in the same liquid-liquid extractor.
EX~MPLE 7 With reference to the symbolic diagram of FIGURE 7~ the charge which is used (line l) is a reforming gasoline having the following composition :
benzene 4% by weight toluene 15% " "
xylenes 20% " "
saturated 61% " "
This charge is sent -to a first liquid-liquid extraction column (12) which has 40 plates~ at a rate of Plow of 100 kg/hr.
Through thè line (S) are sent about 250 kg/hr of N-methyl-morpho-line-3-one~ whereas through the line (10) are sent to the same column 40 kg/hr oP pen-tane~ the extractor being maintained at 25C
(head pressure = 3 atmospheres abso:lute).
The stream discharged from the head (line 2) is sent to the distillation column (13) whereas from the hea~ thereof (line 8) the pentane is recovered which is required for the operation of the extractor~ from the bottom (line 9) is discharged a stream of about 61~3 kg/hr composed essen-tially by the saturated hydrocarbons which were contained in the original charge (l).
lOg~61S
The bottom stream o the extractor (12) is sent to the second liquid-liquid extractor (14) together with about 220 kg/hr of pentane (line 11): this column is consti~uted by 20 plates and operates constantly at 25C and 2.0 atmospheres absclute.
The stream discharged from the head (line 4) is sent to the distillation column (15- whereas from the head thereof (line 6) is recovered the pentane which is necessary for operating the extractor~ from the bottom (line 7) is discharged a stream of about 38,7 kg/hr of a mixture of benzene~ toluene and xylene having a specified percentage o~ saturated compounds.
From the bottom of the second extractor is recovered the solvent which is used at 12.
With reference to the diagram according -to FIGURE 8, the liquid-liquid extraction column (12) is fed with a stream equal to that already disclosed in Example 1.
The same column (formed by 50 plates and working at a pressure of 1.2 atmosphere absolute) is fed~ through the line 7~ also with 150 kg/hr of a mixture composed by N-methyl-morpholine-3-one and water in the proportion of 95/5 by weightO
From the head (line 2) a stream is discharged which~ upon stripping of the solvent contained therein (an operation which i9 not shown in the drawing)~ is composed by :
isoprene 8,4 isopentan~ 13,2 l-pentene 39.7 2-methyl-1-butene 67-3 nor.pentane 120.1 2-pentene-trans 29~4 . 2-pentene-cis 18.1 2-methyl-2-bu-tene 10.8 The stream discharged from the bottom (line 3) is fed -to the lQ~ S
stripping column (13) (head pressure about 1.5 atm.abs.~ 30 plates).
From the he~d (line 4) is discharged a stream of olefins and isoprene, which is recycled to the extrac~or~ whereas from the bottom is discharged a stream (5) which is -fed to the second stripping column (14) (head pressure about 1.2 atm.abs.~ 20 plates~
L/D = 0.2).
From the line (6) is recovered isoprene having a speci~ied contents o~ olefins and sa-turated compounds, which is sent to the extractive distillation column (ll) for removing the polar hy~ro-carbons~ whereas from the line (7) is recovered the solvent which is necessary to operate the column (12)~
The column (12) is operated under the following conditions :
Head pressure 1.1 abs. atm~
L/D 0.9 No. of plates 75 From the head (line 8) is discharged a stream of highly pure lsoprene~ which~ more particularly~ is composed by :
isoprene 268.o mols/hr 2-methyl-2-butene o 5 l~ ~t While Erom the lateral draw in vapor phase (line 9) are dischargecI-the most polar hydrocarbons ( 1~3-cyclopentadiene and iso-propyl-acetylene), from the bottom is discharged (line 10) the 001vont~ which is exempt from hydrocarbons and thus adapted to be r~-used in -the same column 11, ~X~IPLE 9 With reference to the diagram according to FIGURE 5 a the gas-liquid scrubbing column (9) is fed with a stream constituted by :
nor.butane 89.5 mols/hr isobutane 2204 " "
13.
L6i5 l-butene 285 o2 mols/hr 2-butene-trans 117.6 " "
2~butene-cis 91.0 " "
1~3-butadiene 6.8 " "
The working conditions are as ~ollows :
head pressure 5 atm.abs.
No. of plates 40 The same column is fed~ through the line 2, with 1,200 kg/hr of a mixture constituted by N-methyl-morpholine-3-one and water in the proportion oE 93/7 by weight.
The bottom stream (line 4) is sent to the first stripping column (10)~ whereas from the head is discharged a gas stream composed by :
nor.butane 87.7 mols/hr isobutane 22.4 " ~
l-butene 5.7 " "
The operation of the column (10) is characterized by :
head pressure S.S atm.abs.
No. of plates ~0 From the head is discharged a gaseous s-tream of olefin~s and saturated C4 which is recycled to the column (9)~ whereas frcm the bottom is discharged a stream (6) which is ~ed to -the second stripping column (11).
The latter column is operatecl under the ~`ollowing conditions:
head pressure 1.1 abs~atm.
No. o~ plates 30 The gaseous stream is sent to the compressor (12); from the line (8), upon condensation, a stream is drawn which is composed by :
nor.butene 1.8 mols/hr l-butene 279-5 "
2-butene-trans 117.6 " "
14.
~1615 2-butene-cis 91~0 mols/hr 1~3-butadiene 6.8 A portion of the abovementioned stream sent to the com-pressor is recycled through the line (7) to the column (10).
From the tail (11) the solvent is recovered which is re-used in the column (9).
Claims (5)
1. A method of separating a diolefin from a mixture there-of with other hydrocarbons by an extractive distillation, which comprises feeding a stream of said mixture of hydrocarbons to a first extractive distillation column, feeding a stream of solvent comprised of N-methyl-morpholille-3-one to said first extractive distillation column, withdrawing said other hydro-carbons and a minor quantity of said diolefin from the head of said first extractive distillation column, recovering said sol-vent and the balance of said diolefin from said first extractive distillation column as bottom product, feeding said bottom product from said first extractive distillation column to a second extractive distillation column, recovering said diolefin in the bottom pro-duct of the first extractive distillation column from said second extractive distillation column as head product, withdrawing said solvent in the bottom product of the first extractive distilla-tion column from the second extractive distillation column as bottom product, and recycling said bottom product from the second extractive distillation column to the first extractive distillation column.
2. A method as claimed in claim 1, wherein said stream of solvent includes up to 20 % be weight of a member of the group consisting of water and other organic solvents.
3. A method as claimed in claim 2, wherein said other organic solvent is ethylene glycol.
4. The method as claimed in claim 1, wherein said mixture is a mixture of C4 hydrocarbons and said diolefin is butadiene.
5. The method as claimed in claim 1, wherein said mixture is a mixture of C5 hydrocarbons and said diolefin is isoprene.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT19241/76A IT1063231B (en) | 1976-01-14 | 1976-01-14 | USE OF N-METHYL-MORFOLIN-3-ONE AS SOLVENT FOR THE SEPARATION OF HYDROCARBONS |
| IT19241A/76 | 1976-01-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1091615A true CA1091615A (en) | 1980-12-16 |
Family
ID=11156044
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA269,662A Expired CA1091615A (en) | 1976-01-14 | 1977-01-13 | Use of n-methyl-morpholine-3-one in the extractive distillation of hydrocarbons |
Country Status (35)
| Country | Link |
|---|---|
| JP (1) | JPS5288278A (en) |
| AR (1) | AR214059A1 (en) |
| AT (1) | AT356790B (en) |
| AU (1) | AU508405B2 (en) |
| BE (1) | BE850400A (en) |
| BR (1) | BR7700296A (en) |
| CA (1) | CA1091615A (en) |
| CH (1) | CH631203A5 (en) |
| CS (1) | CS200504B2 (en) |
| DD (1) | DD128592A5 (en) |
| DE (1) | DE2701466C3 (en) |
| DK (1) | DK12577A (en) |
| EG (1) | EG12337A (en) |
| ES (1) | ES455306A1 (en) |
| FR (1) | FR2338235A1 (en) |
| GB (1) | GB1523412A (en) |
| GR (1) | GR59765B (en) |
| HU (1) | HU178726B (en) |
| IE (1) | IE45113B1 (en) |
| IN (1) | IN145336B (en) |
| IT (1) | IT1063231B (en) |
| LU (1) | LU76552A1 (en) |
| MW (1) | MW177A1 (en) |
| MX (1) | MX144633A (en) |
| NL (1) | NL7700405A (en) |
| NO (1) | NO148370C (en) |
| PH (1) | PH13737A (en) |
| PL (1) | PL112578B1 (en) |
| PT (1) | PT66065B (en) |
| RO (1) | RO70373A (en) |
| SE (1) | SE423535B (en) |
| TR (1) | TR19071A (en) |
| YU (1) | YU39984B (en) |
| ZA (1) | ZA7796B (en) |
| ZM (1) | ZM677A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL3189022T3 (en) * | 2014-09-05 | 2021-11-08 | Scg Chemicals Company Limited | Separation process for c8 aromatics mixture |
| CN107074687B (en) * | 2014-09-05 | 2020-07-31 | Scg化学有限公司 | Process for enhanced separation of ethylbenzene |
-
1976
- 1976-01-14 IT IT19241/76A patent/IT1063231B/en active
-
1977
- 1977-01-07 GR GR52529A patent/GR59765B/en unknown
- 1977-01-07 ZA ZA770096A patent/ZA7796B/en unknown
- 1977-01-07 AU AU21127/77A patent/AU508405B2/en not_active Expired
- 1977-01-11 CH CH30377A patent/CH631203A5/en not_active IP Right Cessation
- 1977-01-11 TR TR19071A patent/TR19071A/en unknown
- 1977-01-12 AR AR266162A patent/AR214059A1/en active
- 1977-01-12 LU LU76552A patent/LU76552A1/xx unknown
- 1977-01-12 NO NO770098A patent/NO148370C/en unknown
- 1977-01-12 SE SE7700250A patent/SE423535B/en unknown
- 1977-01-12 EG EG21/77A patent/EG12337A/en active
- 1977-01-13 PT PT66065A patent/PT66065B/en unknown
- 1977-01-13 CA CA269,662A patent/CA1091615A/en not_active Expired
- 1977-01-13 AT AT16277A patent/AT356790B/en not_active IP Right Cessation
- 1977-01-13 YU YU83/77A patent/YU39984B/en unknown
- 1977-01-13 FR FR7700935A patent/FR2338235A1/en active Granted
- 1977-01-13 GB GB1402/77A patent/GB1523412A/en not_active Expired
- 1977-01-13 RO RO7789042A patent/RO70373A/en unknown
- 1977-01-13 IN IN43/CAL/77A patent/IN145336B/en unknown
- 1977-01-13 IE IE63/77A patent/IE45113B1/en unknown
- 1977-01-13 HU HU77SA3004A patent/HU178726B/en unknown
- 1977-01-13 DK DK12577A patent/DK12577A/en not_active Application Discontinuation
- 1977-01-14 DD DD7700196937A patent/DD128592A5/en unknown
- 1977-01-14 CS CS77242A patent/CS200504B2/en unknown
- 1977-01-14 ZM ZM6/77A patent/ZM677A1/en unknown
- 1977-01-14 MX MX167704A patent/MX144633A/en unknown
- 1977-01-14 BE BE174097A patent/BE850400A/en not_active IP Right Cessation
- 1977-01-14 MW MW1/77A patent/MW177A1/en unknown
- 1977-01-14 DE DE2701466A patent/DE2701466C3/en not_active Expired
- 1977-01-14 PH PH19358A patent/PH13737A/en unknown
- 1977-01-14 JP JP253277A patent/JPS5288278A/en active Pending
- 1977-01-14 PL PL1977195313A patent/PL112578B1/en unknown
- 1977-01-14 BR BR7700296A patent/BR7700296A/en unknown
- 1977-01-14 NL NL7700405A patent/NL7700405A/en not_active Application Discontinuation
- 1977-01-14 ES ES455306A patent/ES455306A1/en not_active Expired
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