GB2053711A - Catalyst for method of preparing naphthenic acids - Google Patents
Catalyst for method of preparing naphthenic acids Download PDFInfo
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- GB2053711A GB2053711A GB7923937A GB7923937A GB2053711A GB 2053711 A GB2053711 A GB 2053711A GB 7923937 A GB7923937 A GB 7923937A GB 7923937 A GB7923937 A GB 7923937A GB 2053711 A GB2053711 A GB 2053711A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/215—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of saturated hydrocarbyl groups
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
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Abstract
Catalysts for use in a method of preparing naphthenic acids, which comprises oxidising a petroleum fraction boiling in the temperature range 250-350 DEG C with oxygen in a quantity of 0.06-0.065 kg/kg per hour at a temperature of 135-140 DEG C comprise a mixture of 30-40 per cent by weight of manganese naphthenate and 60-70 per cent by weight of potassium naphthenate and are used in a quantity of 1.5-2.5 per cent of the weight of the fraction. The hydroxynaphthenic acids formed are separated off and the naphthenic acids are purified. Naphthenic acids obtained by the method are of high purity and are useful for the manufacture of naphthenic siccatives (salts of metals of variable valency) which are used as additives to lacquers and paints, and for the manufacture of alkyd resins which are the starting material for the manufacture of nitro paints and enamels.
Description
SPECIFICATION
Method of preparing naphthenic acids
This invention relates to petrochemical synthesis, and more particularly it relates to methods of preparing naphthenic acids. These acids are widely used in the manufacture of lacquers and varnishes being the starting material for obtaining naphthenate siccatives which are actually salts of metals having variable valency and are used as additives to paints and varnishes. Naphthenic acids are also used for preparing alkyd resins which are the starting material for the manufacture of nitro enamels and paints. Lead napthenates are effectively used for preparing paints. Naphthenates of cobalt, manganese, nickel, copper and of iron are used as catalysts in the synthesis and oxidation processes.
The invention consists in that proposed is a method of preparing naphthenic acids consisting in oxidation of a petroleum fraction boiling out in the temperature range of 250-350 C with oxygen in the presence of a catalyst at an elevated temperature, in which according to the invention oxygen required for the oxidation process is taken in the quantity of 0.06-0.065 kg/kg per hour and the process is carried out at a temperature of 135-140"C; the catalyst used in the process is a mixture of naphthenates consisting of 30-40 per cent by weight of manganese naphthenate and 60-70 per cent by weight of potassium naphthenate, the catalyst being taken in the quantity of 1.5-2.5 per cent of the weight of the starting petroleum fraction; the resultant mixture of organic oxygen-containing compounds containing hydroxynaphthenic and naphthenic acids is diluted with an organic solvent inactive toward said mixture, the solvent being taken in the weight ratio of 1.1-1.5; the dilution precipitates hydroxynaphthenic acids and they are separated; the remaining mixture of organic oxygen-containing compounds in the solvent is treated with an aqueous solution of sodium hydroxide at a temperature at which the organic solvent boils; a solution of unsaponifiable organic oxygen-containing compounds in the organic solvent is separated from the obtained aqueous solution of sodium naphthenates.The aqueous solution of sodium naphthenates is treated with diethyl sulphate at a temperature of 90-95"C to obtain ethyl naphthenates from which the fraction ethyl naphthenates boiling out at a temperature of 75-170"C is isolted by rectification in vacuum of 3 mm Hg; the isolated fraction is treated with an aqueous solution of sodium hydroxide and the end product is finally isolated from the obtained aqueous solution of sodium naphthenates by the action of minerals acids.
The proposed method may be realized as follows.
A petroleum fraction boiling out in a temperature range of 250-350"C is used as the starting material. The properties of the fraction are as follows; molecular mass, 220-240; specific gravity, 0.8520-0.8560; refractive index, 1.46-1.47; congealing point, minus 50"C-55"C; flash point, 110-120"C. The fraction comprises also the following main hydrocarbons, in per cent by weight:
aromatic 0.1-2
naphthenes 70-75
paraffins 23-29.2
Each petroleum fraction is oxidized with oxygen at a temperature of 135-140"C. The amount of oxygen used in the reaction is 0.06-0.065 kg/kg per hour.Oxidations is carried out in the presence of a catalyst, a mixture of naphthenates consisting of 30-40 per cent by weight of manganese naphthenate and 60-70 per cent by weight of potassium naphthenate. Said mixture is taken in the quantity of 1.5-2.5 per cent of the weight of the starting petroleum fraction. The oxidation process is continued for 4-4.5 hours. The resultant product is a mixture of organic oxygen-containing compounds consisting of naphthenic, aromatic and fatty acids, products of their peroxidation, oxy acids, ether acids, keto acids, lactones and lactides. The acid value of said organic oxygen-containing mixtures is 25-30 mg KOH per gram.Said mixture of organic oxygen-containing compounds comprises the following main compounds, in per cent by weight:
naphthenic acids 15-16
hydroxynaphthenic acids 0.1-1
unsaponifiable oxygen-containing
organic compounds 78-92
Said mixture of organic oxygen-containing compounds is diluted with an organic solvent, inactive toward the mixture, taken in the weight ratio of 1:1-1.5 with respect to the mixture. Said inert solvent may be, e.g.
benzine, boiling out in the temperature range of 80-170 C, or petroleum ether. On dilution with the organic solvent, hydroxynaphthenic acids are precipitated and separated by the known methods, e.g. by filtration.
The remaining solution of the mixture of oxygen-containing organic compounds freed from hydroxynaphthenic acid is treated with an aqueous, preferably 10 per cent solution of sodium hydroxide, at a temperature of at which the solvent boils with stirring, for an hour. At the end of the alkali treatment the reaction mixture is settled to separate the solution of unsaponifiable organic oxygen-containing compounds in the organic solvent from the obtained aqueous solution of sodium naphthenates. The solvent is then separated from the unsaponifiable organic oxygen-containing compounds by distillation and returned to the stage of dilution of the mixture of organic oxygen-containing compounds. The aqueous solution of sodium naphthenates is treated with diethyl sulphate at a temperature of 90-95"C for 90-120 minutes with continuously stirring the mixture.The mixture is then allowed to stand and the precipitated sodium sulphate is separated from ethyl naphthenates by the known methods.
Ethyl naphthenates are distilled in vacuum of 3 mm Hg, and the fraction boiling out in the temperature range of 95-170"C is collected. Said fraction is treated with an aqueous, preferably 10 per cent solution of sodium hydroxide with simultaneous distillation of the formed ethyl alcohol. Naphthenic acids, in the form of their mixture, are isolated by the action of mineral acids from the aqueous solution of sodium naphthenates. Sodium naphthenates are treated with a mineral acid to isolate free naphthenic acids.Thus obtained naphthenic acids having the following characteristics: purity (assay), 96.5-97 per cent; unsaponifiable organic oxygen-containing compounds, 1.0-1.6 per cent by weight; acid value, in mg KOH per gram of naphthenic acids, 230-260; colour, by the iodimetric scale (amount of iodine in 100 ml of a 10 per cent aqueous solution of potassium iodide), 20-22; specific gravity, 0.9521-0.9698; refractivity index, 1.4530- 1.4649. The yield of napthenic acids, calculated with reference to the starting petroleum fraction, is 2.73-3.98 per cent by weight. The catalyst used in the process, (the mixture of manganese naphthenate and potassium naphthenate), is a mixture of solid salts, readily soluble in petroleum hydrocarbons.The catalyst is prepared by the known method, described in the book G.S. Petrov, A.l. Danilevich, and A.Y. Rabinovich "Development of Methods for Oxidation of Petroleum and Mineral Oils and Technical Uses of the Obtained Products",
Goskhimizdat, Leningrad, 1933. The process of preparing the catalyst is illustrated by the following reactions
wherein RCOOH are naphthenic acids.
According to said reactions, naphthenic acid is neutralized with a 20 per cent aqueous solution of alkali at a temperature of 80-90"C for an hour. A pre-calculated quantity of manganese sulphate is then added to the obtained mixture containing potassium naphthenate, and the exchange reaction is carried out at the same temperature for 90 minutes. The resultant product is manganese naphthenate.
The proposed invention hasthefollowing advantages.
Naphthenic acids obtained by the described method are highly pure (96.5-97 per cent). The content is unsaponifiable organic oxygen-containing substances is low (1.0-1.6 per cent by weight). The obtained napthenic acids are clear homogeneous liquids suitable for use in the paint-and-lacquer industry. The catalyst used in the process is selective toward the process and ensures the production of naphthenic acids having from 12 to 15 carbon atoms.
For a better understanding of the invention, the following examples of its practical embodiment are given by way of illustration.
Example 1
The properties of a petroleum fraction boiling in the temperature range from 250 to 350"C are as follows:
molecular mass 224
specific gravity 0.8550
refractive index 1.468
congealing point -50 C flash point 115"C group hydrocarbon composition, in per cent by weight:
aromatic hydrocarbons 1.6
naphthenes 73.2
paraffins 25.2 Thefraction taken in the quantity of 200 kg is oxidized with oxygen at a temperature of 135-140 Cthe oxygen consumption being 0.06 kg/kg per hour for the starting stock. The oxidation is affected in the presence of a catalyst, a mixture of magnagene naphthenate and potassium naphthenate (35 per cent and 65 per cent respectively} taken in the quantity of 1.5 per cent of the weight of the starting stock. The oxidation is continued for four hours. The resultant product of oxidation is 187.7 kg of a mixture of oxygen-containing organic compounds consisting of naphthenic, aromatic, and fatty acids, products of their peroxidation, oxy acids, ether acids, keto acids, lactones and lactides. The acid value of the oxygen-containing mixture is 28 mg
KOH per gram. The obtained mixture of oxygen-containing organic compounds has the following composition, in per cent by weight:
naphthenic acids 15
hydroxynaphthenic acids 0.9
unsaponifiable organic oxygen
containing compounds 79
The mixture of organic oxygen-containing compounds is diluted with 187.7 kg of benzine fraction boiling in the temperature range from 80 to 170 C. Hydroxynaphthenic acids are precipitated and separated from the remaining solution of the mixture of oxygen-containing organic compounds.The hydroxynaphthenic acids can be separated by any known method, for example, by filtration. The quantity of the isolated hydroxynaphthenic acids is 1.7 kg.
The remaining benzine solution of the mixture of organic oxygen-containing compounds (375.4 kg) is treated with a 10 per cent aqueous solution of sodium hydroxide taken in the quantity of 8.04 kg. The alkali treatment is carried out at a temperature of 80-90 C for an hour. The reaction mixture is allowed to stand. The benzine solution of unsaponifiable organic oxygen-containing compounds is separated from the aqueous solution of sodium naphthenates.The benzine solution is distilled to recover 185.5 kg of benzine which is resued at the stage of dilution of the mixture of organic oxygen-containing compounds; another product of distillation is 148.3 kg of unsaponifiable organic oxygen-containing compounds, whose yield with respect to the total weight of the mixture of organic oxygen-containing compounds obtained at the stage of oxidation of the starting stock is 79 per cent by weight.
The aqueous solution of sodium naphthenates is treated with 15.7 kg of diethyl sulphate and the reaction is carried out at a temperature of 90-95"C for 90 minutes. The reaction product is separated from sodium sulphate precipitate by settling. Said reaction product are ethyl naphthenates, the amount of which is 29.4 kg. The ethyl naphthenates are rectified in vacuum of 3 mm Hg to separate the fraction boiling out in the temperature range of 75-170"C. The amount of the distilled product is 8.82 kg. Said fraction is treated with a 10 per cent aqueous solution of sodium hydroxide taken in the quantity of 1.43 kg, and the formed ethyl alcohol is distilled simultaneously (2.9 kg).Next 1.74 kg of sulphuric acid are added to the remaining aqueous solution of sodium naphthenates to isolate 5.47 kg of naphthenic acids which are characterized by the following properties:
purity (assay) 96.5 per cent
unsaponifiable organic oxygen
containing compounds 1.3
acid value, mg KOH per g 245
colour (iodimetric scale) 20
specific gravity 0.9679
refractive index 1.4638
The yield of naphthenic acids, calculated with reference to the starting petroleum fraction, is 2.73 per cent.
Example 2
The petroleum fraction boiling out in a temperature range from 250 to 350"C has the following properties:
molecular mass 240
specific gravity 0.856
refractive index 1.47
congealing point -53 C flash point 120 C group hydrocarbon composition, in per cent by weight:
aromatic hydrocarbons 2.0
naphthenes 75
paraffins 23
The oxidation of the petroleum fraction, taken in the quantity of 200 kg is carried out at a temperature of 136"C, the oxygen consumption rate is 0.061 kg/kg per hour. The process is effected in the presence of a catalyst, a mixture of naphthenates consisting of 70 per cent by weight of potassium naphthenate and 30 per cent by weight of manganese naphthenate.The catalyst is taken in the quantity of 1.82 per cent of the weight of the starting petroleum fraction. The oxidation is continued for 4.5 hour. The oxidation product is 190 kg of a mixture of organic oxygen-containing compounds whose acid value is 25 mg KOH per gram. The obtained mixture is oxygen-containing organic compounds has the following composition, in per cent by weight:
naphthenic acid 16
hydroxynaphthenic acids 1
unsaponifiable organic oxygen
containing compounds 78
The obtained mixture is diluted with 190 kg of benzine to precipitate hydroxynapthenic acids which are separated in the quality of 1.9 kg. The benzine solution of oxygen-containing organic compounds (378.1 kg) is treated with a 10 per cent aqueous solution of sodium hydroxide taken in the quantity of 8.12 kg.The sodium hydroxide treatment is carried out at a temperature of 80-90"C for an hour. The obtained reaction mixture is settled, and the benzine solution of unsaponifiable organic oxygen-containing compounds is separated from the aqueous solution of sodium napthenates. The benzine solution is distilled to recover
185.7 kg of benzine, which is reused, and to separate 156 of unsaponifiable organic oxygen-containing compounds.
The aqueous solution of sodium naphthenates is treated with 15.82 kg of diethyl sulphate at a temperature of 90-95" for two hours to obtain 29.7 kg of ethyl naphthenates, which are then rectified in vacuum of 3 mm
Hg to isolate the fraction boiling in the temperature range of 75-170"C. The fraction (10.4 kg) is treated with a 10 per cent solution of sodium hydroxide taken in the quantity of 1.7 kg. Ethyl alcohol (3.4 kg) is separated from the reaction products. Then 2.1 kg of phosphoric acid are added to the aqueous solution of sodium naphthenates to isolate 6.76 kg of naphthenic acids.
The obtained naphthenic acids have the following characteristics:
purity (assay) 97 per cent
unsaponifiable organic oxygen
containing compounds 1.58 per cent by weight
acid value 230 mg KOH per gram
colority (iodimetric scale) 22
specific gravity 0.9698
refractive index 1.4649
The yield of naphthenic acids, calculated with reference to the starting stock, is 3.38 per cent by weight.
Example 3
The petroleum fraction boiling in the temperature range of 250-350"C has the following characteristics:
molecular mass 220
specific gravity 0.852
refractive index 1.461
congealing point -55 C flash point 110"C group composition, in per cent by weight:
aromatic hydrocarbons 0.4
naphthenes 70.4
paraffins 29.2
The given petroleum fraction, taken in the quantity of 200 kg, is oxidized at a temperature of 138"C at an oxygen consumption of 0.065 kg/kg per hour, in the presence of a catalyst consisting of 40 per cent by weight of manganese naphthenate and 60 per cent by weight of potassium napthenate. The catalyst is taken in the quality of 1.96 per cent of the weight of the starting stock.The oxidation process is continued for 4.5 hours to given 189 kg of a mixture of organic oxygen-containing compounds whose acid value is 30 mg KOH per gram. The obtained mixture of organic oxygen-containing compounds has the following composition, in per cent by weight:
naphthenic acids 15
hydroxynaphthenic acids 0.8
unsaponifiable organic oxygen.
containing compounds 80
The obtained mixture is diluted with 189 kg of benzine to precipitate 1.5 kg of hydroxynaphthenic acids, which are then separated. The benzine solution of oxygen-containing organic compounds (376.5 kg) are treated with a 10 per cent aqueous solution of sodium hydroxide taken in the quantity of 8.02 kg at a temperature of 80-90"C for an hour. The obtained reaction mixture is allowed to stand, and the benzine solution of the unsaponifiable organic oxygen-containing compounds is separated from the aqueous solution of sodium napthenates. The benzine solution is distilled to recover 185.2 kg of benzine, which is then reused, and to obtain 151.2 kg of the unsaponiable organic oxygen-containing compounds.The aqueous solution of sodium naphthenates is treated with 15.62 kg of diethyl sulphate at a temperature of 90-95"C for 90 minutes. The result of the reaction are 29.2 kg of ethyl naphthenates which are then reactified in vacuum of 3 mm Hg to separate the fraction boiling in the temperature range of 75-170"C (9.34 kg) which is then treated with 1.46 kg of a 10 per cent aqueous solution of sodium hydroxide. Ethyl alcohol is recovered from the reaction products in the quantity of 2.9 kg. The aqueous solution of sodium napthenates is mixed with 1.64 kg of hydrochloric acid to isolate 5.5 kg of naphthenic acids.
The characteristics of thus obtained naphthenic acids are as follows:
purity (assay) 97 per cent
unsaponifiable organic oxygen
containing substances 1.1 per cent by weight
acid value 260 mg KOH per gram
colority (iodimetric scale) 22
specific gravity 0.9528
refractive index 1.4532
The yield of naphthenic acids, calculated with reference to the starting petroleum fraction, is 2.75 per cent by weight.
Example 4
A petroleum fraction boiling in the temperature range of 250-350"C has the following characteristics:
molecular mass 228
specific gravity 0.856
refractive index 1.4708
congealing point -55 C flash point 115"C hydrocarbon composition, in per cent by weight:
aromatic hydrocarbons 1.4
naphthenes 74.6
paraffins 24.0
Said petroleum fraction, taken in the quantity of 200 kg is oxidized at a temperature of 135-140"C, at the oxygen consumption of 0.06/kg/kg per hour in the presence of a catalyst consisting of 35 per cent by weight of magnanese naphthenate and 65 per cent by weight of potassium naphthenate. The catalyst is taken in the quantity of 2.5 per cent of the starting stock.The product of the oxidation reaction are 139.7 kg of a mixture of organic oxygen-containing compounds characterized by the said number of 25 mg KOH per gram.
The obtained mixture of organic oxygen-containing compounds has the following composition, in per cent by weight:
naphthenic acids 15
hydroxynapthenic acids 0.1
unsaponifiable organic oxygen
containing compounds 82
The obtained mixture is diluted with 209.5 kg of petroleum ether to precipitate 0.2 kg of hydroxynaphthenic acids, which are separated by the known methods. The solution of organic oxygen-containing compounds in petroleum ether (349.2 kg) is treated with 3.98 kg of a 10 per cent aqueous solution of sodium hydroxide at a temperature at which petroleum ether boils. The treatment is continued for an hour. The obtained reaction mixture is settled to separate the solution of unsaponifiable organic oxygen-containing compounds for the aqueous solution of sodium naphthenates.The separate solution of organic unsaponifiables in petroleum ether is distilled to recover 185 kg of the solvent, which is then reused, and to isolate 174.5 kg of the unsaponifiable organic oxygen-containing compounds. The aqueous solution of sodium naphthenates is treated with 15.6 kg of diethyl sulphate for 90 minutes at a temperature of 90-95"C to isolate 29.2 kg of ethyl naphthenates. Said ethyl naphthenates are rectified in vacuum of 3 mm Hg to isolate the fraction boiling in the temperature range of 75-170"C (9.4 kg) which is treated with 1.5 kg of a 10 per cent aqueous solution of sodium hydroxide. The result of the treatment with the alkali is the separation of 3 kg of ethyl alcohol. The aqueous solution of sodium naphthenates is mixed with 1.7 kg of sulphuric acid to isolate 7.97 kg of naphthenic acids.
The characteristics of thus prepared naphthenic acids is as follows:
purity (assay) 96.8 per cent
unsaponifiable organic oxygen
containing compounds 1.6 per cent by weight
acid value 230 mg KOH per gram
colority (iodimetric scale) 22
specific gravity 0.9521
refractive index 1.4530
The yield of naphthenic acids, calculated with reference to the starting petroleum fraction, is 3.98 per cent by weight.
Claims (5)
1. A method of preparing naphthenic acids, which comprises oxidizing a petroleum fraction boiling in the temperature range 250-350"C with oxygen in a quantity of 0.06 - 0.065 kg/kg per hour at a temperature of 135-140"C in the presence of a catalyst which is a mixture consisting essentially of 30-40 per cent by weight of manganese naphenate and 60-70 per cent by weight of potassium naphenate in a quantity of 1.5-2.5 per cent of the weight of the fraction; separating off hydroxynaphenic acids formed; and purifying the naphenic acids formed.
2. A method for preparing naphthenic acids which comprises oxidising a petroleum fraction boiling in the temperature range 250-350"C with oxy oxygen in a quantity of 0.06-0.065 kg/kg per hour at a temperature of 135 - 140"C in the presence of a catalyst which is a mixture consisting essentially of 30-40 percent by weight of manganese naphthenate and 60-70 per cent by weight of potassium in a quantity of 1.5-2.5 per cent of the weight of the fraction; diluting the obtained mixture of organic oxygen-containing compounds containing hydroxynaphthenic acids and naphthenic acids with an organic solvent inactive towards said mixture, said solvent being taken in a weight ratio of 1:1-1.5 to the starting petroleum mixture fraction so as to precipitate hydroxynaphthenic acids, which are then separated; treating the solution of the organic oxygen-containing compounds freed from hydroxynaphthenic acids with an aqueous solution of sodium hydroxide at the boiling temperature of said organic solvent so as to separate an aqueous solution of sodium naphthenates from a solution of unsaponifiable organic oxygen-containing compounds in the organic solvent; treating said aqueous solution of sodium naphthenates with diethyl sulphate at a temperature of 90-95"C to separate ethyl naphthenates, from which a fraction of ethyl naphthenates boiling in a temperature
range of 75-170 C is separates by rectification in a vacuum of 3 mm Hg; treating the isolated fraction with an
aqueous solution of sodium hydroxide and isolating the naphthenic acids from the obtained aqueous solution of sodium naphthenates by the action of mineral acids.
3. A method as claimed in Claim 1, substantially as disclosed in any Example.
4. Naphthenic acid produced by the method of any preceding claim.
5. A catalyst for the oxidation of a petroleum fraction with oxygen in the preparation of naphthenic acids,
which consists essentially of 30-40 per cent by weight of mangenese naphthenate and 60-70 per cent by
weight of potassium naphthenate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7923937A GB2053711B (en) | 1979-07-10 | 1979-07-10 | Catalyst for method of preparing naphthenic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7923937A GB2053711B (en) | 1979-07-10 | 1979-07-10 | Catalyst for method of preparing naphthenic acids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2053711A true GB2053711A (en) | 1981-02-11 |
| GB2053711B GB2053711B (en) | 1983-06-02 |
Family
ID=10506401
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7923937A Expired GB2053711B (en) | 1979-07-10 | 1979-07-10 | Catalyst for method of preparing naphthenic acids |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2053711B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113730954A (en) * | 2021-09-09 | 2021-12-03 | 福建省长汀金龙稀土有限公司 | Method for recovering isooctanol and sulfonated kerosene from waste organic of naphthenic acid system for extracting and separating yttrium |
-
1979
- 1979-07-10 GB GB7923937A patent/GB2053711B/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113730954A (en) * | 2021-09-09 | 2021-12-03 | 福建省长汀金龙稀土有限公司 | Method for recovering isooctanol and sulfonated kerosene from waste organic of naphthenic acid system for extracting and separating yttrium |
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| Publication number | Publication date |
|---|---|
| GB2053711B (en) | 1983-06-02 |
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