US3583906A - Aromatic extraction process with diglycolamine solvent - Google Patents

Aromatic extraction process with diglycolamine solvent Download PDF

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Publication number
US3583906A
US3583906A US752740A US3583906DA US3583906A US 3583906 A US3583906 A US 3583906A US 752740 A US752740 A US 752740A US 3583906D A US3583906D A US 3583906DA US 3583906 A US3583906 A US 3583906A
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US
United States
Prior art keywords
diglycolamine
extraction
aromatic
solvent
aromatics
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.)
Expired - Lifetime
Application number
US752740A
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English (en)
Inventor
Michael R Basila
Alfred R Pate Jr
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Howe Baker Engineers LLC
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Howe Baker Engineers LLC
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Publication date
Application filed by Howe Baker Engineers LLC filed Critical Howe Baker Engineers LLC
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Publication of US3583906A publication Critical patent/US3583906A/en
Anticipated expiration legal-status Critical
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Classifications

    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10GCRACKING 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
    • C10G21/00Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents
    • C10G21/06Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents characterised by the solvent used
    • C10G21/12Organic compounds only
    • C10G21/20Nitrogen-containing compounds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L21/00Compositions of unspecified rubbers
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/16Nitrogen-containing compounds
    • C08K5/17Amines; Quaternary ammonium compounds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2555/00Characteristics of bituminous mixtures
    • C08L2555/40Mixtures based upon bitumen or asphalt containing functional additives
    • C08L2555/60Organic non-macromolecular ingredients, e.g. oil, fat, wax or natural dye
    • C08L2555/70Organic non-macromolecular ingredients, e.g. oil, fat, wax or natural dye from natural non-renewable resources
    • C08L2555/74Petrochemicals other than waxes, e.g. synthetic oils, diesel or other fuels, hydrocarbons, halogenated or otherwise functionalized hydrocarbons

Definitions

  • Extraction of aromatics from reformed naphtha and subsequent purification into benzene, toluene, and xylene Extraction of aromatics from jet fuel and kerosene to improve the burning quality. Improves smoke point, heat of combustion, aniline point, and other physical properties.
  • Extraction of aromatics from diesel to improve octane number, diesel index, and general burning quality.
  • Extraction of aromatics from light catalytic cycle oil to upgrade it to diesel fuel.
  • the amount of diglycolamine used in relation to the aromatic compound containing hydrocarbon liquid to be such that the ratio of diglycolamine to hydrocarbon liquid is at least 1:1. Good results are obtained when the ratio of diglycolamine to hydrocarbon liquid is within the range of 3:1 to 10:1. Excellent results are achieved in the case of petroleum hydrocarbon liquids containing aromatics when the ratio is at about 5:1.
  • the process is conducted by contacting the aromatic compound containing hydrocarbon liquid with the diglycolamine under conditions to produce intimate admixture of the two components. Mixing and agitation should be mild. Countercurrent extraction techniques may be em ployed to good advantage.
  • the aromatic compound in a specific embodiment of the subject invention, can be contacted with the diglycolamine in an extractive distillation process.
  • the extraction may be conducted over a wide variety of temperatures with good results being obtained in all cases.
  • the temperatures may be within the range of -400" F. and, more preferably, 75-200 F. with good extraction of aromatics being accomplished. It is understood that the temperature range should not exceed the boiling point of the liquids treated or of the diglycolamine.
  • the diglycolamine is an effective material for extracting aromatics when the diglycolamine contains as much as 10% by volume of water. This means that the material can be used in repeated multistage extraction processes without continuous water removal being necessary. When the water content of the diglycolamine exceeds about 10% by volume, then it is desirable that the diglycolamine be separated from the water since aromatic extraction efficiency tends to be diminished.
  • Molar aromatic concentration in heavy phase 2 D Molar aromatic concentration in light phase 3 Product from this run used as feed in the second stage extraction.
  • the diglycolamine concentration ranges between 0.02 and 0.06 mole/liter. Increasing the temperature from 75 to 200 F. does not product a substantial change. Most of the experiments were done at a diglycolaminezhydrocarbon ratio of 5:1; hence, the carryover amounts to less than 0.04 to 0.12 percent of the total diglycolamine. This can be further reduced by water washing the raffinate. For example, a raffinate from a platformate extraction containing 0.0390 mole/liter of diglycolamine was washed with an equal volume of water. The wash water contained 0.0376 mole/liter and the treated raffinate 0.0015 mole/liter of diglycolamine. Similar results have been obtained with other ralfinate samples.
  • Table VII summarizes the elfects of up to 10% (by volume) of water in the diglycolamine in the extraction of the Table II platformate. It can be seen that 15% water does not exert pernicious effects on the extraction efficiency of diglycolamine. In fact, the results suggest a beneficial effect of a small amount (1%) of Water. The presence of 10% water in the diglycolamine reduces the extraction efilciency. The diglycolamine concentration in the raifinate is not strongly influenced by the introduction of water into the system.
  • diglycolamine is an excellent solvent for aromatics from hydrocarbons and provides the art with a new improved solvent extraction material.
  • the diglycolamine is very effective when used to extract low molecular weight single ring aromatics such as benzene, toluene, and xylene.
  • the diglycolamine is also efiective when used to extract aromatics boiling in higher temperature regions, such as naphtha, kerosene and diesel oil.
  • diglycolamine was compared with the wellknown solvents sulfolane and diethyleneglycol.
  • the solvent system was a benzene-heptane mixture and the comparisons were made based on the data supplied in E. Mueller and G. Hoehfeld, 7th World Petroleum Congress Proceedings, 4, 13 (1967). The results are formulated below in Table VIII.
  • a process for extracting aromatic compounds from a hydrocarbon liquid containing aromatic compounds comprising contacting said hydrocarbon liquid with an aqueous mixture of diglycolamine containing from about 1% to about 5% water, by volume, for a time sufiicient to extract substantial quantities of aromatic compounds from said hydrocarbon liquid.
  • hydrocarbon liquid is naphtha, kerosene or diesel oil.
  • aromatic compounds are substantially benzene, toluene, xylene or mixtures thereof.
  • hydrocarbon liquid is naphtha, kerosene or diesel oil; the aromatic compounds are substantially benzene, toluene, xylene or mixtures thereof; the ratio of the aqueous mixture of diglycolamine to hydrocarbon liquid is between about 3:1 and 10:1, by volume; and the resulting hydrocarbon liquid from which substantial quantities of aromatic compounds have been extracted and the aqueous mixture of diglycolamine are thereafter separated.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
US752740A 1968-08-15 1968-08-15 Aromatic extraction process with diglycolamine solvent Expired - Lifetime US3583906A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US75274068A 1968-08-15 1968-08-15

Publications (1)

Publication Number Publication Date
US3583906A true US3583906A (en) 1971-06-08

Family

ID=25027617

Family Applications (1)

Application Number Title Priority Date Filing Date
US752740A Expired - Lifetime US3583906A (en) 1968-08-15 1968-08-15 Aromatic extraction process with diglycolamine solvent

Country Status (9)

Country Link
US (1) US3583906A (nl)
BE (1) BE737477A (nl)
BR (1) BR6911600D0 (nl)
DE (1) DE1942367C3 (nl)
ES (1) ES370531A1 (nl)
FI (1) FI51947C (nl)
FR (1) FR2015726A1 (nl)
GB (1) GB1248827A (nl)
NL (1) NL153268B (nl)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3981798A (en) * 1974-08-29 1976-09-21 Nalco Chemical Company Liquid/liquid extraction using certain ethers and esters
US4291189A (en) * 1980-04-28 1981-09-22 Monsanto Company Alkylation process improvement
CN104073291A (zh) * 2013-03-26 2014-10-01 中国石油化工股份有限公司 一种液液抽提分离柴油中芳烃的装置和方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2956946A (en) * 1958-07-10 1960-10-18 Exxon Research Engineering Co Process for removing acids with an ethylene glycol monoalkylamine ether
FR1457744A (fr) * 1964-09-29 1966-01-24 Metallgesellschaft Ag Procédé de séparation des hydrocarbures aromatiques par extraction ou distillation extractive au moyen de mélanges de solvants

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3981798A (en) * 1974-08-29 1976-09-21 Nalco Chemical Company Liquid/liquid extraction using certain ethers and esters
US4291189A (en) * 1980-04-28 1981-09-22 Monsanto Company Alkylation process improvement
CN104073291A (zh) * 2013-03-26 2014-10-01 中国石油化工股份有限公司 一种液液抽提分离柴油中芳烃的装置和方法
CN104073291B (zh) * 2013-03-26 2016-01-20 中国石油化工股份有限公司 一种液液抽提分离柴油中芳烃的装置和方法

Also Published As

Publication number Publication date
DE1942367B2 (de) 1974-07-11
ES370531A1 (es) 1971-04-16
FI51947B (nl) 1977-01-31
FI51947C (fi) 1977-05-10
DE1942367C3 (de) 1975-03-20
FR2015726A1 (nl) 1970-04-30
DE1942367A1 (de) 1970-11-19
BE737477A (nl) 1970-02-16
NL153268B (nl) 1977-05-16
BR6911600D0 (pt) 1973-03-13
GB1248827A (en) 1971-10-06
NL6912422A (nl) 1970-02-17

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