GB366025A - Improvements in the separation of products containing oxygen from hydrocarbons - Google Patents
Improvements in the separation of products containing oxygen from hydrocarbonsInfo
- Publication number
- GB366025A GB366025A GB3223130A GB3223130A GB366025A GB 366025 A GB366025 A GB 366025A GB 3223130 A GB3223130 A GB 3223130A GB 3223130 A GB3223130 A GB 3223130A GB 366025 A GB366025 A GB 366025A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrocarbons
- sulphur dioxide
- separated
- alcohols
- liquid
- 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
Links
- 229930195733 hydrocarbon Natural products 0.000 title abstract 26
- 150000002430 hydrocarbons Chemical class 0.000 title abstract 26
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 title abstract 5
- 239000001301 oxygen Substances 0.000 title abstract 5
- 229910052760 oxygen Inorganic materials 0.000 title abstract 5
- 238000000926 separation method Methods 0.000 title abstract 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 48
- 239000000203 mixture Substances 0.000 abstract 25
- 239000004291 sulphur dioxide Substances 0.000 abstract 24
- 235000010269 sulphur dioxide Nutrition 0.000 abstract 24
- 235000019441 ethanol Nutrition 0.000 abstract 18
- 239000007788 liquid Substances 0.000 abstract 18
- 239000000047 product Substances 0.000 abstract 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 12
- 239000003921 oil Substances 0.000 abstract 11
- 235000019198 oils Nutrition 0.000 abstract 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 10
- 150000001298 alcohols Chemical class 0.000 abstract 10
- 238000000034 method Methods 0.000 abstract 10
- 230000003647 oxidation Effects 0.000 abstract 10
- 238000007254 oxidation reaction Methods 0.000 abstract 10
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 abstract 8
- 150000002148 esters Chemical class 0.000 abstract 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 8
- 150000002927 oxygen compounds Chemical class 0.000 abstract 8
- 239000003054 catalyst Substances 0.000 abstract 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 6
- -1 aliphatic alcohols Chemical class 0.000 abstract 6
- 125000001931 aliphatic group Chemical group 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 6
- 239000000470 constituent Substances 0.000 abstract 6
- 230000001066 destructive effect Effects 0.000 abstract 6
- 238000005984 hydrogenation reaction Methods 0.000 abstract 6
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 abstract 6
- 235000019271 petrolatum Nutrition 0.000 abstract 6
- 239000012188 paraffin wax Substances 0.000 abstract 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 abstract 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 4
- 150000007513 acids Chemical class 0.000 abstract 4
- 125000002947 alkylene group Chemical group 0.000 abstract 4
- 150000001735 carboxylic acids Chemical class 0.000 abstract 4
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 4
- 239000003995 emulsifying agent Substances 0.000 abstract 4
- 229930195729 fatty acid Natural products 0.000 abstract 4
- 239000000194 fatty acid Substances 0.000 abstract 4
- 235000019253 formic acid Nutrition 0.000 abstract 4
- 239000007789 gas Substances 0.000 abstract 4
- 238000010438 heat treatment Methods 0.000 abstract 4
- 239000000463 material Substances 0.000 abstract 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 4
- 239000000126 substance Substances 0.000 abstract 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 4
- 239000001993 wax Substances 0.000 abstract 4
- 229940116318 copper carbonate Drugs 0.000 abstract 3
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 abstract 3
- MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 2
- 239000005662 Paraffin oil Substances 0.000 abstract 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 abstract 2
- 229910000831 Steel Inorganic materials 0.000 abstract 2
- 150000001299 aldehydes Chemical class 0.000 abstract 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N anhydrous methyl formate Natural products COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 abstract 2
- 239000010775 animal oil Substances 0.000 abstract 2
- 238000009835 boiling Methods 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 230000003197 catalytic effect Effects 0.000 abstract 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- VNNRSPGTAMTISX-UHFFFAOYSA-N chromium nickel Chemical compound [Cr].[Ni] VNNRSPGTAMTISX-UHFFFAOYSA-N 0.000 abstract 2
- 238000006356 dehydrogenation reaction Methods 0.000 abstract 2
- 239000003599 detergent Substances 0.000 abstract 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 abstract 2
- 229960005215 dichloroacetic acid Drugs 0.000 abstract 2
- 238000004821 distillation Methods 0.000 abstract 2
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 abstract 2
- 230000001804 emulsifying effect Effects 0.000 abstract 2
- 238000001704 evaporation Methods 0.000 abstract 2
- 239000003925 fat Substances 0.000 abstract 2
- 150000004665 fatty acids Chemical class 0.000 abstract 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 abstract 2
- 238000007710 freezing Methods 0.000 abstract 2
- 230000008014 freezing Effects 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 150000002576 ketones Chemical class 0.000 abstract 2
- 150000002596 lactones Chemical class 0.000 abstract 2
- 239000003077 lignite Substances 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 239000002480 mineral oil Substances 0.000 abstract 2
- 235000010446 mineral oil Nutrition 0.000 abstract 2
- VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 abstract 2
- 238000006386 neutralization reaction Methods 0.000 abstract 2
- 229910017604 nitric acid Inorganic materials 0.000 abstract 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 2
- 150000004831 organic oxygen compounds Chemical class 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- 238000007127 saponification reaction Methods 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 229940084106 spermaceti Drugs 0.000 abstract 2
- 239000012177 spermaceti Substances 0.000 abstract 2
- 239000010959 steel Substances 0.000 abstract 2
- 238000003756 stirring Methods 0.000 abstract 2
- 150000005846 sugar alcohols Polymers 0.000 abstract 2
- 239000011269 tar Substances 0.000 abstract 2
- 239000002641 tar oil Substances 0.000 abstract 2
- 235000015112 vegetable and seed oil Nutrition 0.000 abstract 2
- 235000019871 vegetable fat Nutrition 0.000 abstract 2
- 239000008158 vegetable oil Substances 0.000 abstract 2
- 238000009736 wetting Methods 0.000 abstract 2
- 239000000080 wetting agent Substances 0.000 abstract 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000010779 crude oil Substances 0.000 abstract 1
- 229910052748 manganese Inorganic materials 0.000 abstract 1
- 239000011572 manganese Substances 0.000 abstract 1
- SGGOJYZMTYGPCH-UHFFFAOYSA-L manganese(2+);naphthalene-2-carboxylate Chemical compound [Mn+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 SGGOJYZMTYGPCH-UHFFFAOYSA-L 0.000 abstract 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Abstract
Organic oxygen compounds mainly consisting of aliphatic alcohols, fatty acids, fatty acid esters, and aliphatic ketones and aldehydes are separated from mixtures thereof with nonaromatic hydrocarbons containing at least 8 carbon atoms, by treating the liquid mixtures with liquid sulphur dioxide at temperatures below 75 DEG C., preferably at which the single components are liquid, and preferably in the absence of substantial quantities of water. The treatment may be carried out in a stirring autoclave with about \ba1/4\be to 5 parts by volume of sulphur dioxide for each part of initial material. On standing, two layers are formed, the upper layer mainly consisting of hydrocarbons, and the lower of a solution of the oxygen compounds in sulphur dioxide, from which the oxygen compounds may be separated by evaporating the sulphur dioxide or by freezing. The process may be carried out in a continuous manner. If the hydrocarbon content of the initial mixture be high, a single or repeated treatment with liquid sulphur dioxide is sufficient. If the oxygen containing compounds predominate, the solvent power of sulphur dioxide for the hydrocarbons may be reduced by the addition of from 1 to 10 per cent of aliphatic oxygen containing compounds, for example, methanol, ethanol, n-propanol, isopropanol, formic or acetic acid, methyl or ethyl formate, formamide, acetamide, or ethly urethane. Initial materials to which the process may be applied include mixtures obtained by the destructive oxidation by means of air, nitrogen oxides, nitric acid, or several such agents conjointly, of aliphatic or naphthenic hydrocarbons such as mineral oil fractions boiling over 180 DEG C., for example, paraffin wax, ceresine, Russian gas oil, paraffin oil, synthetic oils such as brown coal tar oils, or mixtures obtained by the destructive hydrogenation of tars, oils and the like. By separating the unoxidized hydrocarbons from such oxidation products, carboxylic acids, esters, alcohols of high molecular weight, ketones, lactones, and the like are obtained; if desired, a mixture mainly consisting of high molecular alcohols may be obtained by separating the saponifiable constituents of the mixture before the treatment with sulphur dioxide. Oxidation products which have been subjected to a further treatment, for example, by heating, distillation, or catalytic hydrogenation may be treated. Alcohol mixtures obtained by the catalytic dehydrogenation of esters such as animal or vegetable oils, fats and waxes, and of polyhydric alcohols may be separated by means of the process from the hydrocarbons formed by the hydrogenation. Alcohol mixtures obtained by condensing aliphatic or naphthenic hydrocarbons with oxygen compounds such as alkylene oxides or substances forming alkylene oxides may also be separated thereby from the accompanying hydrocarbons. The oxygen compounds obtained by the above methods may be sulphonated or treated with alkalis, if acids be present, to prepare emulsifying agents. The mixtures of alcohols of high molecular weight free from hydrocarbons so obtained may be used for the preparation of esters, or for the manufacture of wetting, emulsifying and cleansing agents by sulphonation, sulphuric esters or sulphonic acids being obtained according to the method of sulphonation employed, and neutralization with alkaline substances. According to examples (1) a Pennsylvanian middle oil is oxidized with air in presence of manganese naphthanate, the acid constituents removed by saponification, and the remainder hydrogenated with hydrogen in presence of a nickel-Kieselguhr catalyst; by treating with liquid sulphur dioxide at 25 DEG C. a mixture consisting chiefly of alcohols is separated from the product, (2) oxidation products of Russian gas oil are separated from accompanying hydrocarbons with liquid sulphur dioxide, (3) unsaponifiable constituents obtained from a product of destructive oxidation of soft paraffin wax after separation of carboxylic acids and hydrogenation in presence of a catalyst obtained by reducing basic copper carbonate containing 2 per cent of molybdic acid, are separated from the unchanged wax by treatment with a mixture of liquid sulphur dioxide and formamide, acetic acid or formic acid, (4) oxygenated compounds obtained by treating paraffin wax with nitrogen dioxide and heating the product to 230 DEG C. for two hours in a vessel made of or lined with chromium-nickel steel are separated by means of liquid sulphur dioxide from the accompanying hydrocarbons, (5) Spermaceti is hydrogenated in presence of a catalyst obtained by reducing basic copper carbonate containing 2 per cent of vanadium pentoxide, and a mixture consisting mainly of alcohols separated from the product by means of liquid sulphur dioxide, and (6) a paraffin fraction of Pennsylvanian crude oil is treated with ethylene oxide in presence of a Freedel-Crafts catalyst, ice and water is added thereto, and the water-insoluble reaction product after separation from the aqueous layer is treated with liquid sulphur dioxide, a product consisting mainly of alcohols being separated thereby from the accompanying hydrocarbons. Specification 7309/14, [Class 91, Oils &c.], is referred to.ALSO:Organic oxygen compounds mainly consisting of aliphatic alcohols, fatty acids, fatty acid esters, and aliphatic ketones and aldehydes, are separated from mixtures thereof with non-aromatic hydrocarbons containing at least 8 carbon atoms, by treating the liquid mixtures with liquid sulphur dioxide at temperatures below 75 DEG C., preferably at which the single components are liquid, and preferably in the absence of substantial quantities of water. The treatment may be carried out in a stirring autoclave with about \ba1/4\be-5 parts by volume of sulphur dioxide for each part of initial material. On standing, two layers are formed, the upper layer mainly consisting of hydrocarbons, and the lower of a solution of the oxygen compounds in sulphur dioxide, from which the oxygen compounds may be separated by evaporating the sulphur dioxide or by freezing. The process may be carried out in a continuous manner. If the hydrocarbon content of the initial mixture be high, a single or repeated treatment with liquid sulphur dioxide is sufficient. If the oxygen-containing compounds predominate, or if it is desired to isolate a pure product free from hydrocarbons, the solvent power of sulphur dioxide for the hydrocarbons may be reduced by the addition of from 1 to 10 per cent of aliphatic oxygen containing compounds, for example, methanol, ethanol, n-propanol, isopropanol, formi or acetic acid, methyl or ethyl formate, formamide, acetamide, or ethyl urethane. Initial materials to which the process may be applied include mixtures obtained by the destructive oxidation by means of air, nitrogen oxides, nitric acid, or several such agents conjointly, of aliphatic or naphthenic hydrocarbons such as mineral oil fractions boiling over 180 DEG C., for example, paraffin wax, ceresine, Russian gas oil, paraffin oil, synthetic oils such as brown coal tar oils, or mixtures obtained by the destructive hydrogenation of tars, oils, and the like. By separating the unoxidized hydrocarbons from such oxidation products, carboxylic acids, esters, alcohols of high molecular weight, ketones, lactones, and the like are obtained; if desired, a mixture mainly consisting of high molecular alcohols may be obtained by separating the saponifiable constituents of the mixture before the treatment with sulphur dioxide. Oxidation products which have been subjected to a further treatment, for example, by heating, distillation, or catalytic hydrogenation may be treated. Alcohol mixtures obtained by the catalytic dehydrogenation of esters such as animal or vegetable oils, fats, and waxes, and of polyhydric alcohols may be separated by means of the process from the hydrocarbons formed by the hydrogenation. Alcohol mixtures obtained by condensing aliphatic or naphthenic hydrocarbons with oxygen compounds such as alkylene oxides or substances forming alkylene oxides may also be separated thereby from the accompanying hydrocarbons. The oxygen compounds obtained by the above methods may be sulphonated or treated with alkalies, if acids be present, to prepare emulsifying agents. The mixtures of alcohols of high molecular weight free from hydrocarbons so obtained may be used for the preparation of esters, or for the manufacture of wetting, emulsifying, and cleansing agents by sulphonation, sulphuric esters or sulphonic acids being obtained according to the method of sulphonation employed, and neutralization with alkaline substances. According to examples (1) a Pennsylvanian middle oil is oxidized with air in presence of manganese naphthenate, the acid constituents removed by saponification, and the remainder hydrogenated with hydrogen in presence of a nickel-kieselguhr catalyst; by treating with liquid sulphur dioxide at 25 DEG C. a mixture consisting chiefly of alcohols is separated from the product; (2) oxidation products of Russian gas oil are separated from accompanying hydrocarbons with liquid sulphur dioxide; (3) unsaponifiable constituents obtained from a product of destructive oxidation of soft paraffin wax after separation of carboxylic acids and hydrogenation in presence of a catalyst obtained by reducing basic copper carbonate containing 2 per cent of molybdic acid, are separated from the unchanged wax by treatment with a mixture of liquid sulphur dioxide and formamide, acetic acid, or formic acid; (4) oxygenated compounds obtained by treating paraffin wax with nitrogen dioxide and heating the product to 230 DEG C. for two hours in a vessel made of or lined with chromium-nickel steel are separated by means of liquid sulphur dioxide from the accompanying hydrocarbons; (5) spermaceti is hydrogenated in presence of a catalyst obtain
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3223130A GB366025A (en) | 1930-10-27 | 1930-10-27 | Improvements in the separation of products containing oxygen from hydrocarbons |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3223130A GB366025A (en) | 1930-10-27 | 1930-10-27 | Improvements in the separation of products containing oxygen from hydrocarbons |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB366025A true GB366025A (en) | 1932-01-27 |
Family
ID=10335345
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3223130A Expired GB366025A (en) | 1930-10-27 | 1930-10-27 | Improvements in the separation of products containing oxygen from hydrocarbons |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB366025A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3105099A (en) * | 1959-09-01 | 1963-09-24 | Abbott Lab | Method of rendering alcohols anhydrous |
| WO2008048495A3 (en) * | 2006-10-13 | 2008-07-24 | Archer Daniels Midland Co | Hydrogenation process and high monoene compositions obtained therefrom |
| US7491820B2 (en) | 2005-04-26 | 2009-02-17 | Archer-Daniels-Midland Company | Hydrogenation with copper compositions catalyst |
-
1930
- 1930-10-27 GB GB3223130A patent/GB366025A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3105099A (en) * | 1959-09-01 | 1963-09-24 | Abbott Lab | Method of rendering alcohols anhydrous |
| US7491820B2 (en) | 2005-04-26 | 2009-02-17 | Archer-Daniels-Midland Company | Hydrogenation with copper compositions catalyst |
| WO2008048495A3 (en) * | 2006-10-13 | 2008-07-24 | Archer Daniels Midland Co | Hydrogenation process and high monoene compositions obtained therefrom |
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