US2437649A - Separation of phenols from hydrocarbon distillates by steam distillation - Google Patents

Separation of phenols from hydrocarbon distillates by steam distillation Download PDF

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US2437649A
US2437649A US581557A US58155745A US2437649A US 2437649 A US2437649 A US 2437649A US 581557 A US581557 A US 581557A US 58155745 A US58155745 A US 58155745A US 2437649 A US2437649 A US 2437649A
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phenols
hydrocarbons
steam
water
hydrocarbon
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US581557A
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Milner David William
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YORKSHIRE TAR DISTILLERS Ltd
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YORKSHIRE TAR DISTILLERS Ltd
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    • 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
    • C10G31/00—Refining of hydrocarbon oils, in the absence of hydrogen, by methods not otherwise provided for
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/005—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by obtaining phenols from products, waste products or side-products of processes, not directed to the production of phenols, by conversion or working-up
    • C07C37/007—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by obtaining phenols from products, waste products or side-products of processes, not directed to the production of phenols, by conversion or working-up from the tar industry
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
    • C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
    • C07C37/74—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by distillation
    • C07C37/76—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by distillation by steam distillation

Definitions

  • the usual method-of separating phenols from hydrocarbon distillates involves washing the distillates with a solution of caustic alkali and then acidifying the aqueous liquor in order to set free the phenols which are caused to separate as an oily layer.
  • the object of the present invention is to provide an improved process for the separation, without the employment of caustic soda or acids, of phenols from hydrocarbon distillates which contain hydrocarbon and phenols of closely related boiling points including such distillates obtained from a continuous tar still or petroleum still.
  • the invention consists, broadly, in subjecting such hydrocarbon distillates containing phenols which distill along with the hydrocarbons when such distillates are vaporized in the absence of steam to distillation in the presence of steam, whereby the major portion of the hydrocarbon components are distilled oif with water in the form of an azeotropic mixture leaving a residue or giving rise in a later stage of distillation to a product having a relatively high phenols content.
  • the invention is particularly applicable to hydrocarbon fractions from continuous stills in which the boiling points of the hydrocarbons and phenols are closely related.
  • the invention is, however, also applicable to the treatment of mixtures of hydrocarbons and phenols in which there is a substantial difference in boiling points between the constituent hydrocarbons and phenols and is furthermore applicable to mixtures containing in addition to hydrocarbons and phenols other bodies such as tar bases.
  • Distillation in the presence of steam may be carried out in a continuous manner by running the mixture of hydrocarbons and phenols down a column up which steam is blown, the hydrocarbons being taken off at the top and the phenols at the bottom.
  • the process may be carried out by blowing steam into a body of a mixture of hydrocarbons and phenols in a still, in conditions in which the hydrocarbons will pass 01f and .be condensed in the form of an azeotropic mixture, the phenols remaining behind.
  • the steam distillation may with advantage be carried out with the employment of a good fractionating column, products of a greatly improved and saleable quality containing phenols or tar acids can be produced directly.
  • the separation may be efiected by carrying out the distillation in a still in which is contained a relatively large proportion of water, so that there is always anexcess of water in the still during the operation.
  • the stil1 should preferably be fitted with a fractionating or dephlegmating column or a reflux or some other form of apparatus which will cause a portion of the distillate to reflux and thereby cause the separation of a distillate consisting mainly of hydrocarbons and water.
  • the mixture of hydrocarbons and water distilling over and comparatively free from phenols is run into a separator and the separated water returned to the column or other reflux device, or alternatively the distillate can be taken of! and separated at a later stage in which case the addition of steam or water in a stepwise or continuous manner to the contents of the still must be made in order to keep an excess of water in the still.
  • the material to be treated contains parafiinic as well as aromatic hydrocarbons
  • prelerably fractions boiling within a temperature range of not exceeding 20 C. and, for instance, a range of 5 C. are treated in which case the paramnic hydrocarbons will be'concentrated in the fraction arising towards the final stages in the distillation treatment in the presence of water.
  • the distilling operation is carried out until the residual liquid in the still is sufliciently free from hydrocarbons for the purpose for which it is intended.
  • the tar bases may be removed by well-known methods from such fractions and the mixture of hydrocarbons and phenols returned to the still for further treatment or added to a further charge, which is subjected to distillation in the presence of water.
  • saleable phenol fractions can be produced direct from certain mixtures of hydrocarbon oils containing phenols, tar bases, and other impurities.
  • the phenols constitute the distillation residue in this column and they are withdrawn by way of the pipe I l.
  • vapours from the column pass out by way of the pipe l5 and are led to an analyser l8 and thence into a separator H the lower layer of liquid formed thereon being returned by way of the pipe iii to the column ll.
  • a portion of the material separating in the separator I! may be withdrawn by way of the pipe IQ for re-treatment in the column 2, being returned to that column by way of the feed pipe I.
  • distillation in the presence of steam is carried out in a continuous manner by running the hydrocarbon. distillates containing phenols down a column up which steam is blown, the hydrocarbons being taken oil at the top and the phenols at the bottom of the column.
  • Process of treating hydrocarbon distillates containing paraflinic as well as aromatic hydrocarbons and in addition phenols which distill along with the hydrocarbons when such distillates are vaporized in the absence of steam which comprises subjecting the hydrocarbon distillates containing both hydrocarbons and phenols in the form of fractions boiling within a temperature range to distillation in the presence of steam, collecting the paraffinic hydrocarbons in concentrated form as fractions arising towards the final stages in the distillation treatment and the phenols are preponderatingly contained in the residue.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

. w. MILNER 2,437,649
SEPARATION OF PHENOLS FROM HYDROCARBON DISTILLATES BY STEAM DISTILLATION Filed March 7, 1945 Hydrocarbon Ou/et I I Ana I-yzer" fiandense 9 T l6 ,9
Sen-Mar Separator l hvfer' & Ii C back /nfermediafe Out/8i- Szeam l2 fi-Febof/er j MReboI/er IN V EN TOR.
I avid \Af. Milne? Patented Mar. 9, 1948 SEPARATION OF CARBON 'rmLs'rlo David William Milner,
to Yorkshire Tar Dis England Application March "1, 1945, Serial no.
In Great Britain November 20,
PHENOLS FROM HYDRO- IIQIISTILLATES BY STEAM DIS- Leeds, England, assignmtillers Limited, Barnsley,
8 Claims. (Cl. 202-42) This invention relates to the separation of phenols from hydrocarbon distillates.
The usual method-of separating phenols from hydrocarbon distillates involves washing the distillates with a solution of caustic alkali and then acidifying the aqueous liquor in order to set free the phenols which are caused to separate as an oily layer.
The object of the present invention is to provide an improved process for the separation, without the employment of caustic soda or acids, of phenols from hydrocarbon distillates which contain hydrocarbon and phenols of closely related boiling points including such distillates obtained from a continuous tar still or petroleum still.
The invention consists, broadly, in subjecting such hydrocarbon distillates containing phenols which distill along with the hydrocarbons when such distillates are vaporized in the absence of steam to distillation in the presence of steam, whereby the major portion of the hydrocarbon components are distilled oif with water in the form of an azeotropic mixture leaving a residue or giving rise in a later stage of distillation to a product having a relatively high phenols content.
The invention is particularly applicable to hydrocarbon fractions from continuous stills in which the boiling points of the hydrocarbons and phenols are closely related.
The invention is, however, also applicable to the treatment of mixtures of hydrocarbons and phenols in which there is a substantial difference in boiling points between the constituent hydrocarbons and phenols and is furthermore applicable to mixtures containing in addition to hydrocarbons and phenols other bodies such as tar bases.
Distillation in the presence of steam may be carried out in a continuous manner by running the mixture of hydrocarbons and phenols down a column up which steam is blown, the hydrocarbons being taken off at the top and the phenols at the bottom.
Alternatively, the process may be carried out by blowing steam into a body of a mixture of hydrocarbons and phenols in a still, in conditions in which the hydrocarbons will pass 01f and .be condensed in the form of an azeotropic mixture, the phenols remaining behind. v
.The steam distillation may with advantage be carried out with the employment of a good fractionating column, products of a greatly improved and saleable quality containing phenols or tar acids can be produced directly.
In accordance with the invention, the separation may be efiected by carrying out the distillation in a still in which is contained a relatively large proportion of water, so that there is always anexcess of water in the still during the operation.
The stil1 should preferably be fitted with a fractionating or dephlegmating column or a reflux or some other form of apparatus which will cause a portion of the distillate to reflux and thereby cause the separation of a distillate consisting mainly of hydrocarbons and water.
Conveniently, in accordance with the invention, the mixture of hydrocarbons and water distilling over and comparatively free from phenols, is run into a separator and the separated water returned to the column or other reflux device, or alternatively the distillate can be taken of! and separated at a later stage in which case the addition of steam or water in a stepwise or continuous manner to the contents of the still must be made in order to keep an excess of water in the still.
Where the material to be treated contains parafiinic as well as aromatic hydrocarbons, prelerably fractions boiling within a temperature range of not exceeding 20 C. and, for instance, a range of 5 C. are treated in which case the paramnic hydrocarbons will be'concentrated in the fraction arising towards the final stages in the distillation treatment in the presence of water.
The distilling operation is carried out until the residual liquid in the still is sufliciently free from hydrocarbons for the purpose for which it is intended.
In the later stages of the distillation, some intermediate fractions may be obtained containing the varying amounts of phenols and other impurities such as tar bases.
The tar bases may be removed by well-known methods from such fractions and the mixture of hydrocarbons and phenols returned to the still for further treatment or added to a further charge, which is subjected to distillation in the presence of water.
By the process, in accordance with the invention, saleable phenol fractions can be produced direct from certain mixtures of hydrocarbon oils containing phenols, tar bases, and other impurities.
The following particulars are given by way of examples to illustrate the result which may be invention.
EXAMPLE I A sample of coal tar naphtha distilling between 175 C. and 195 C. was placed in a still with a fractionating column and twice its volume of water added. The mixture was fractionated using a dephlegmator on the top of the column. The distillate was run into a separator and the water returned to the column as reflux until the separation no longer took place easily owing to the rising specific gravity of the oil in the distillate. At this point the whole of the distillate was taken off and the water separated later. The water thus separated can be used in. the next charge.
Results Sp. 'Ier Hydro- Or. Acids Bases carbons Per cent Per cent Per cent Charge 50 gallons .968 33 62 1 20% allons..- .970 l 4 95 2 8 gallons..-.. .950 8 8 84 3 5 gallons .91l 26 8 66 4 Bgnllons 1.022 58 16 28 5 3gallons... 86 9 5 6 9% gallons residues... 1.067 99.7 0.15 0.15
The residue was taken out of the still, the water separated and the oil distilled. Of the original charge 1% was left as a pitchy residue.
Thus about two-thirds of the hydrocarbons were recovered substantially free from phenols and about two-thirds of the phenols present were recovered as a marketable product. The intermediaries can be re-worked after removing the bases or they can be used for other purposes.
EXAMPLE II A crude coal tar naphtha fraction distilling 170 to 175 C. was fractionated in the Presence of water using a separator on the still head so that the water separated could be run back down the column as reflux.
The original naphtha tested as follows:
Flask distillation drop 169.5 0., dry 1'75.5 0.
Sp. gr. .954 Parafllns ercent. 14 Tar acids do 34 Bases (10.... 1.2
On fractionation of 45 gallons of the above material under the conditions stated the following fractions were obtained.
Sip. Tar an Acids Bases Parafiins Percent Per cent Per cent 1 Bgnllons .932 1 ii 1.5 2 -.do .942 Nil 1 8 3 d0.. .943 Nil 1.5 4.75 4 .do.. .939 Ni] 1.5 6.3 5 ...do.- .880 1.5 2.0 35 6 ...do.. .834 3.5 1.0 62 7 2gallons .816 4.5 0.5 69 8 13 gallons resi 99.56 0.14 0.3
points supplying them to column 2, to which steam is admitted by way of the pipe 3.
In the lower part of this column there is located a re-boiier The azeotropic mixture passes away from the column in the form of vapour by way of the pipe 5 to a condenser 5 and a separator 1 from which the lower layer, that is water and hydrocarbon, is returned by way of the pipe 8 to the column and the separated hydrocarbon led away through the pipe 9. The distillation residue consisting largely of phenols in the column 2 passes out by way of the pipe in and is delivered to the distillation column l I to which steam is admitted by way of the pipe H. In this column there is a reboiler i3.
The phenols constitute the distillation residue in this column and they are withdrawn by way of the pipe I l.
The vapours from the column pass out by way of the pipe l5 and are led to an analyser l8 and thence into a separator H the lower layer of liquid formed thereon being returned by way of the pipe iii to the column ll.
A portion of the material separating in the separator I! may be withdrawn by way of the pipe IQ for re-treatment in the column 2, being returned to that column by way of the feed pipe I.
I claim:
1. The process of treating hydrocarbon distillates containing phenols which distill along with the hydrocarbons when such distillates are vaporized in the absence of steam which comprises subjecting such hydrocarbon distillates to distillation in the presence of steam, driving all as vapour the major portion of the hydrocarbon components with water in the form of an azeotropic mixture and recovering the phenols in the residual or higher boiling fractions.
2. A process as claimed in claim 1, in which distillation in the presence of steam is carried out in a continuous manner by running the hydrocarbon. distillates containing phenols down a column up which steam is blown, the hydrocarbons being taken oil at the top and the phenols at the bottom of the column.
3. A process as claimed in claim 1, in which. steam is blown into a body of a mixture of hydrocarbons and phenols in a still whereby the hydro carbons are driven off in the form of an areatropic mixture and are condensed, the phenols remaining mainly behind as a residue.
4. The process of treating hydrocarbon. tillates containing phenols which distill along with the hydrocarbons when such distillates are vaporized in the absence of steam which comprises subjecting such hydrocarbon distillates to distillation in the presence of steam. condensing the mixture of hydrocarbons and water distilling over and which is comparatively free from phenols, running the mixture into a separator whereby the hydrocarbons and water are separated and returning the separated water to the body of material undergoing treatment.
5. Process of treating hydrocarbon distillates containing paraflinic as well as aromatic hydrocarbons and in addition phenols which distill along with the hydrocarbons when such distillates are vaporized in the absence of steam which comprises subjecting the hydrocarbon distillates containing both hydrocarbons and phenols in the form of fractions boiling within a temperature range to distillation in the presence of steam, collecting the paraffinic hydrocarbons in concentrated form as fractions arising towards the final stages in the distillation treatment and the phenols are preponderatingly contained in the residue.
6. The process of treating hydrocarbon distillates containing phenols which distill along with the hydrocarbons when such distillates are vaporized in the absence of steam which comprises subjecting such hydrocarbon distillates to distillatiom in the presence of steam, driving off the major portion of the hydrocarbon components "with water in the form of an azeotropic mixture, and thereafter subjecting the residual phenolic residue to distillation in the presence of water.
"7. The process of treating hydrocarbon distillates containing phenols which distill along with the hydrocarbons when such distillates are vaporized in the absence of steam which comprises subjecting such hydrocarbon distillates t0 distillation in the presence of steam, whereby the major portion of the hydrocarbon components are distilled off with water in the form of an azeotropic mixture, thereafter interrupting the supply of steam and distilling of! the phenols in the substantial absence of water.
10 phenolic material remaining.
DAVID WIILIAM MILNER.
REFERENCES CITED The following references are of record in the file or this patent:
UNITED STATES PATENTS 20 Number Name Date 2,040,096 Miller May 12, 1936 2,168,570 Kraft Aug. 8, 1939 2,186,298 Kiersted Jan. 9, 1940 2,370,530 G886 Feb. 27, 1945
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Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2523248A (en) * 1948-02-19 1950-09-19 Cities Service Oil Co Separation of alcohols and acids from fischer-tropsch synthesis product
US2600182A (en) * 1948-05-12 1952-06-10 Texas Co Refining kerosenes and gas oil by ternary azeotropic distillation with furfural and water
US2600184A (en) * 1951-11-27 1952-06-10 Texas Co Refining kerosenes and gas oil by ternary azeotropic distillation
US2702784A (en) * 1952-06-26 1955-02-22 California Research Corp Azeotropic removal of hydrocarbon contaminants from phenol
US2762760A (en) * 1952-07-23 1956-09-11 Monsanto Chemicals Extractive distillation of phenol-containing mixtures
US2785114A (en) * 1957-03-12 Schmalenbach
US2849358A (en) * 1954-10-11 1958-08-26 Phillips Petroleum Co Method of recovering heterocyclic nitrogen bases from aqueous solutions
US2862855A (en) * 1951-11-24 1958-12-02 Ruetgerswerke Ag Azeotrope distillation of aromatic isopropyl compounds from phenol
US2874096A (en) * 1954-01-26 1959-02-17 Exxon Research Engineering Co Purification of amyl alcohol
US3151047A (en) * 1960-09-12 1964-09-29 Phillips Petroleum Co Separation of organic compounds by fractional distillation and phase separation
US3184398A (en) * 1960-09-28 1965-05-18 Ruetgerswerke Ag Method of processing crude phenols
US3298933A (en) * 1961-11-29 1967-01-17 Hooker Chemical Corp Production of ultra-pure phenol by removal from a phenol of high purity of small amounts of chlorine-containing organic impurities
US3309289A (en) * 1961-10-11 1967-03-14 Snia Viscosa Recovery of benzoic acid by distillation in presence of excess water
US3326781A (en) * 1963-07-15 1967-06-20 Phillips Petroleum Co Recovery of organic polar compounds from polymerization processes
US3421567A (en) * 1965-07-28 1969-01-14 Edeleanu Gmbh Method and apparatus for extracting a vaporizable component from a liquid
US4138310A (en) * 1975-05-14 1979-02-06 Chemische Werke Huels Aktiengesellschaft Continuous process for the removal of residual monomer from aqueous dispersions of homo- and copolymers of vinyl chloride
US4149940A (en) * 1976-12-22 1979-04-17 Imperial Chemical Industries Limited Methanol

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2040096A (en) * 1929-08-06 1936-05-12 Barrett Co Recovery of tar acids from tar
US2168570A (en) * 1935-05-31 1939-08-08 Lummus Co Solvent recovery
US2186298A (en) * 1938-05-25 1940-01-09 Texas Co Solvent refining of hydrocarbon oil and recovery of the solvent
US2370530A (en) * 1942-09-29 1945-02-27 Shell Dev Method of solvent recovery in vapor phase extraction processes

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2040096A (en) * 1929-08-06 1936-05-12 Barrett Co Recovery of tar acids from tar
US2168570A (en) * 1935-05-31 1939-08-08 Lummus Co Solvent recovery
US2186298A (en) * 1938-05-25 1940-01-09 Texas Co Solvent refining of hydrocarbon oil and recovery of the solvent
US2370530A (en) * 1942-09-29 1945-02-27 Shell Dev Method of solvent recovery in vapor phase extraction processes

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2785114A (en) * 1957-03-12 Schmalenbach
US2523248A (en) * 1948-02-19 1950-09-19 Cities Service Oil Co Separation of alcohols and acids from fischer-tropsch synthesis product
US2600182A (en) * 1948-05-12 1952-06-10 Texas Co Refining kerosenes and gas oil by ternary azeotropic distillation with furfural and water
US2862855A (en) * 1951-11-24 1958-12-02 Ruetgerswerke Ag Azeotrope distillation of aromatic isopropyl compounds from phenol
US2600184A (en) * 1951-11-27 1952-06-10 Texas Co Refining kerosenes and gas oil by ternary azeotropic distillation
US2702784A (en) * 1952-06-26 1955-02-22 California Research Corp Azeotropic removal of hydrocarbon contaminants from phenol
US2762760A (en) * 1952-07-23 1956-09-11 Monsanto Chemicals Extractive distillation of phenol-containing mixtures
US2874096A (en) * 1954-01-26 1959-02-17 Exxon Research Engineering Co Purification of amyl alcohol
US2849358A (en) * 1954-10-11 1958-08-26 Phillips Petroleum Co Method of recovering heterocyclic nitrogen bases from aqueous solutions
US3151047A (en) * 1960-09-12 1964-09-29 Phillips Petroleum Co Separation of organic compounds by fractional distillation and phase separation
US3184398A (en) * 1960-09-28 1965-05-18 Ruetgerswerke Ag Method of processing crude phenols
US3309289A (en) * 1961-10-11 1967-03-14 Snia Viscosa Recovery of benzoic acid by distillation in presence of excess water
US3298933A (en) * 1961-11-29 1967-01-17 Hooker Chemical Corp Production of ultra-pure phenol by removal from a phenol of high purity of small amounts of chlorine-containing organic impurities
US3326781A (en) * 1963-07-15 1967-06-20 Phillips Petroleum Co Recovery of organic polar compounds from polymerization processes
US3421567A (en) * 1965-07-28 1969-01-14 Edeleanu Gmbh Method and apparatus for extracting a vaporizable component from a liquid
US4138310A (en) * 1975-05-14 1979-02-06 Chemische Werke Huels Aktiengesellschaft Continuous process for the removal of residual monomer from aqueous dispersions of homo- and copolymers of vinyl chloride
US4149940A (en) * 1976-12-22 1979-04-17 Imperial Chemical Industries Limited Methanol

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