1.
US Patent 4,265,828 / Knifton / May 5, 1981
Manufacture of ethylene glycol from synthesis gas
Abstract
This invention concerns a process of making ethylene glycol which comprises the steps of contacting a mixture of CO and H.sub.2 with a catalyst system comprising a ruthenium-containing compound dispersed in a low melting quaternary phosphonium or ammonium base or salt, and heating said resultant reaction mixture under a pressure of 500 psi or greater at a temperature of at least 150.degree. C. for a sufficient time to provide said ethylene glycol.
2.
US Patent 6,417,411 / Kakimoto , et al. / July 9, 2002
Method for production of ethylene glycol
Abstract
In a composite process for subjecting ethylene to catalytic gas phase oxidation thereby obtaining ethylene oxide and causing this ethylene oxide to react with water thereby obtaining ethylene glycol, a method for producing the ethylene glycol is provided which permits effective utilization of the energy at the step for dehydrating and concentrating the resultant aqueous ethylene glycol solution. In the production of ethylene glycol by the supply of the aqueous ethylene glycol solution to a concentrating treatment at the multi-effect evaporator, the method contemplated by this invention for the production of ethylene glycol comprises utilizing as the source of heating at least one specific step the steam generated in the multi-effect evaporator.
3.
US Patent 6,380,419 / Kawabe / April 30, 2002
Abstract
Ethylene glycol and a carbonate ester are simultaneously produced by reacting ethylene oxide and carbon dioxide to form ethylene carbonate, hydrolyzing of the solution containing the ethylene carbonate to obtain ethylene glycol, purifying ethylene glycol, transesterifying ethylene carbonate and a hydroxyl group-containing compound to form the corresponding carbonate ester and ethylene glycol, separating the carbonate ester and separating ethylene carbonate.
4.
US Patent 4,661,609 / Knifton / April 28, 1987
Process for cosynthesis of ethylene glycol and dimethyl carbonate
Abstract
A process is disclosed for the cosynthesis of ethylene glycol and dimethyl carbonate by reacting methanol and ethylene carbonate in the presence of a catalyst selected from the group consisting of zirconium, titanium and tin.
5.
US Patent 4,734,518 / Knifton / March 29, 1988
Abstract
A process is disclosed for the cosynthesis of ethylene glycol and dimethyl carbonate by reacting methanol and ethylene carbonate in the presence of a homogeneous catalyst from the group consisting of soluble miscible tertiary phosphines arsines, and stibines and soluble, miscible bivalent sulphur and selenium compounds.
6.
US Patent 5,214,182 / Knifton / May 25, 1993
Process for cogeneration of ethylene glycol and dimethyl carbonate
Abstract
A process is disclosed for the cogeneration of ethylene glycol and dimethyl carbonate by reacting methanol and ethylene carbonate in the presence of a heterogeneous, phosphine-bound polymer catalyst. Dimethyl carbonate and ethylene glycol are generated in greater than 98% selectivity.
7.
US Patent 6,080,897 / Kawabe / June 27, 2000
Method for producing monoethylene glycol
Abstract
Disclosed is a method for producing monoethylene glycol, which is a method for producing ethylene glycol that comprises a carbonation step in which ethylene oxide is allowed to react with carbon dioxide in the presence of a carbonation catalyst thereby effecting formation of a reaction solution containing ethylene carbonate, a hydrolysis step in which the reaction solution is converted into an ethylene glycol aqueous solution by hydrolyzing ethylene carbonate in the reaction solution and a distillation step in which purified ethylene glycol and a catalyst solution containing the carbonation catalyst are obtained from the ethylene glycol aqueous solution by distillation, wherein the improvement resides in that the reaction is carried out in the presence of a carbonation catalyst using a bubble column reactor by supplying ethylene oxide, carbon dioxide and water into the reactor.
8.
US Patent 3,922,314 / Cocuzza , et al. / November 25, 1975
Abstract
A process for the production of ethylene glycol by hydrolysis of ethylene oxide with water which comprises enriching the aqueous solution originating from stripping the gases from the catalytic oxidation of ethylene with oxygen, with ethylene oxide and with carbon dioxide and hydrolyzing the ethylene oxide contained in this enriched solution.
9.
US Patent 4,160,116 / Mieno , et al. / July 3, 1979
Process for the production of alkylene glycols
Abstract
Process for the production of an alkylene glycol in which the hydration of an alkylene oxide is carried out in the presence of carbon dioxide using a quaternary phosphonium salt as a catalyst.
10.
US Patent 4,283,580 / Odanaka , et al. / August 11, 1981
Abstract
A process for the production of alkylene glycols, which comprises causing a corresponding alkylene carbonate to react with water in the presence of a catalyst of at least one member selected from the group consisting of molybdenum and tungsten.
11.
US Patent 4,400,559 / Bhise / August 23, 1983
Process for preparing ethylene glycol
Abstract
Ethylene glycol is prepared by a process in which ethylene oxide is extracted from an aqueous solution with near-critical or super-critical carbon dioxide. Thereafter an ethylene oxide--carbon dioxide--water mixture is contacted with a catalyst to form ethylene carbonate, which is then hydrolyzed to ethylene glycol in the presence of the same catalyst. The ethylene glycol is separated as product and the carbon dioxide and the catalyst are recycled.
12.
US Patent 4,117,250 / Foster , et al. / September 26, 1978
Continuous process for producing alkylene glycols from alkylene carbonates
Abstract
A continuous process for hydrolyzing alkylene carbonates according to specific procedure whereby the akylene glycol obtained is essentially free of polymeric glycols and contains minimum amounts of dimeric glycols.
13.
US Patent 4,237,324 / Raines , et al. / December 2, 1980
Production of monoglycols from alkylene carbonates
Abstract
Alkylene glycols are produced from alkylene carbonates by hydrolysis in the presence of water at temperatures of from about 80.degree. to about 200.degree. C. Catalysts, such as alumina, are employed at temperatures from 80.degree. to about 150.degree. C. and only slightly greater than the stoichiometric amount of water is employed to allow the most efficient use of the process.
14.
US Patent 4,556,748 / Tsang , et al. / December 3, 1985
Abstract
Prepare alkylene glycols by hydrolyzing alkylene carbonates under specific conditions, and a reactor specially designed therefor.
15.
US Patent 5,763,691 / Kawabe , et al. / June 9, 1998
Ethylene glycol process
Abstract
The present invention relates to a process for producing ethylene glycol from ethylene oxide wherein ethylene oxide in a gas resulting from oxidation of ethylene is absorbed in a specific absorbing solution, is allowed to react with carbon dioxide, converted into ethylene carbonate, and then subjected to hydrolysis to produce ethylene glycol. According to the present invention, a large energy consuming step such as stripping of ethylene oxide and separation of excess amounts of water during the ethylene glycol production becomes unnecessary and the process can be greatly simplified by combining the ethylene oxide absorption step and the carbonation step.
16.
US Patent 4,508,927 / Bhise , et al. / April 2, 1985
Abstract
A process for preparation of glycols in which the vapor remaining after the partial condensation of a conventional ethylene oxide stripper overhead vapor stream is contacted with an aqueous solution of ethylene carbonate to recover ethylene oxide. No water need be removed from the enriched ethylene carbonate stream. Carbon dioxide is added and ethylene carbonate is formed by reaction at about 50.degree. to 200.degree. C. and 5 to 150 kg/cm.sup.2 gauge in the presence of a suitable catalyst, preferably about 0.5-20 wt % of an organic phosphonium halide. After stripping off unreacted components, the ethylene carbonate is hydrolyzed to glycols in the presence of the same carbonation catalyst and at temperatures in the range of about 100.degree. to 200.degree. C. and pressures of about 5 to 150 kg/cm.sup.2 gauge. Optionally, ethylene oxide and ethylene carbonate may be co-produced.
17.
US Patent 6,187,972 / Kawabe , et al. / February 13, 2001
Abstract
A process for producing an alkylene glycol, which is a continuous process for producing an alkylene glycol comprising the following steps (1) to (4), wherein the hydrolysis step (2) is divided into a plurality of stages, and the hydrolysis is carried out so that the water concentration in a reaction stage wherein the conversion of the alkylene carbonate is at least 60%, is from 15 to 30 wt %: (1) a carbonating step of reacting an alkylene oxide with carbon dioxide gas in the presence of a carbonating catalyst to form a reaction solution containing an alkylene carbonate, (2) a hydrolysis step of hydrolyzing the reaction solution obtained in step (1) while releasing carbon dioxide gas, to form an aqueous alkylene glycol solution, (3) a distillation step of distilling the aqueous alkylene glycol solution to obtain at least a dehydrated alkylene glycol and a solution containing the carbonating catalyst, and (4) a recycling step of supplying the solution containing the carbonating catalyst to the carbonating step (1).
18.
US Patent 5,763,691 / Kawabe , et al. / June 9, 1998
Abstract
The present invention relates to a process for producing ethylene glycol from ethylene oxide wherein ethylene oxide in a gas resulting from oxidation of ethylene is absorbed in a specific absorbing solution, is allowed to react with carbon dioxide, converted into ethylene carbonate, and then subjected to hydrolysis to produce ethylene glycol. According to the present invention, a large energy consuming step such as stripping of ethylene oxide and separation of excess amounts of water during the ethylene glycol production becomes unnecessary and the process can be greatly simplified by combining the ethylene oxide absorption step and the carbonation step.
19.
US Patent 4,691,041 / Duranleau , et al. / September 1, 1987
Abstract
A process is disclosed for the preparation of ethylene glycol and dimethyl carbonate by reacting methanol and ethylene carbonate in the presence of a series of heterogenous catalyst systems including ion exchange resins with tertiary amine, quaternary ammonium, sulfonic acid and carboxylic acid functional groups, alkali and alkaline earth silicates impregnated into silica and ammonium exchanged zeolites.
20.
US Patent 4,677,234 / Bartley / June 30, 1987
Abstract
A process for the preparation of ethylene glycol by the vapor phase catalytic hydrogenation of at least one of di(lower alkyl) oxalate and lower alkyl glycolate in the presence of a hydrogenation catalyst comprising a carrier, which catalyst is suitable for the hydrogenation of alkyl oxalate and alkyl glycolate to ethylene glycol, wherein the improvement lies in preparing the catalyst by contacting the carrier with a cooper ammonium carbonate complex medium and reducing the catalytically-active copper moiety to its active copper form.
21.
US Patent 4,665,22 / Whyman / May 12, 1987
Abstract
A process for the production of ethylene glycol, methanol, ethanol and/or esters thereof from mixtures of carbon monoxide and hydrogen (synthesis gas) which comprises contacting a mixture of carbon monoxide and hydrogen with a catalyst at elevated pressure in a liquid medium, said catalyst comprising ruthenium and at least one other metal from Group VIII of the Periodic Table, and wherein the molar proportion of ruthenium is at least 50 percent relative to the other Group VIII metals. The process is particularly applicable to the selective production of ethylene glycol. The preferred catalysts, which comprise ruthenium/rhodium, may be present in elemental form, as coordination compounds or salts, e.g. carbonyls, acetyl acetonates or carboxylates. It is especially preferred to use a co-catalyst comprising a compound of one or more the metals of Groups IA, IIA or IIB or a nitrogen containing cation and/or base. Suitable liquid media include carboxylic acids (e.g. acetic acid) and ethers (e.g. tetraglyme).
22.
US Patent 4,600,726 / Bertleff , et al. / July 15, 1986
Abstract
Ethylene glycol is prepared from carbon monoxide and hydrogen under superatmospheric pressure and at an elevated temperature in the presence of a rhodium-containing catalyst together with a cobalt catalyst, the molar ratio of rhodium to cobalt being from about 20:1 to 60:1.
23.
US Patent 4,585,890 / Miyazaki , et al. / April 29, 1986
Abstract
A hydrogenation catalyst composition useful for the hydrogenation of an oxalate diester, said composition being composed of a reduction product of copper-containing silica gel formed by contacting an ammine complex of copper with colloidal silica sol; and a process for producing the aforesaid composition. Using a catalyst composed of the aforesaid composition, ethylene glycol and/or a glycolic acid ester can be produced from an oxalate diester efficiently with high conversions and selectivities and without causing pollution attributed to the use of a chromium-containing catalyst composition.
24.
US Patent 4,568,780 / Knifton / February 4, 1986
Abstract
This invention relates to the manufacture of ethylene glycol and more particularly to a low pressure process for making ethylene glycol comprising reacting synthesis gas, i.e. a mixture of carbon monoxide and hydrogen, plus 1,3-dioxolane in the presence of a homogenous liquid catalyst containing an effective amount of cobalt-containing compound and a silane or germane-containing promoter dispersed in a hydrocarbon solvent at a temperature of at least 50.degree. C. and a pressure of at least 500 psi, where the particular solvents used allow the desired product to be separated from the reaction mixture by phase separation.
25.
US Patent 4,565,896 / Knifton , et al. / January 21, 1986
Abstract
This invention relates to the manufacture of ethylene glcyol and more particularly to a low pressure process for making ethylene glycol comprising reacting synthesis gas, i.e. a mixture of carbon monoxide and hydrogen, plus formaldehyde in the presence of a homogeneous liquid catalyst containing an effective amount of cobalt-containing compound and a silicon or germanium-containing promoter and a solvent at a temperature of at least 50.degree. C. and a pressure of at least 500 psi wherein said ethylene glycol product separates as a separate liquid phase from the solvent.
26.
US Patent 4,558,072 / Grigsby, Jr. , et al. / December 10, 1985
Process for preparing ethylene glycol and lower monohydric alcohols from syngas using a novel catalyst system
Abstract
Ethylene glycol along with ethylene glycol derivatives and alcohols are prepared from syngas in improved yields by contacting a mixture of carbon monoxide and hydrogen with a catalyst system comprising a ruthenium-containing compound and a manganese-containing compound, both dispersed in a low melting quaternary phosphonium compound dissolved in a solvent and heating the resulting reaction mixture at a temperature of at least 150.degree. C. and a pressure of at least 30 atm. for sufficient time to produce the desired ethylene glycol and monohydric alcohols, and then recovering the same from the reaction mixture. A rhodium-containing compound may optionally be used with the ruthenium-containing compound.
27.
US Patent 4,315,994 / Knifton / February 16, 1982
Abstract
This invention concerns a process of making alkylene glycols and their ethers which comprises contacting a mixture of carbon monoxide and hydrogen with a bimetallic catalyst system comprising ruthenium(III) acetylacetonate and rhodium(III) acetylacetonate dispersed in a low melting quaternary phosphonium or ammonium base or salt at a pressure of 500 psi or greater and at a temperature of at least 150.degree. C. for a sufficient time to provide said glycols and ethers.
28.
US Patent 4,396,726 / Simons / August 2, 1983
Abstract
Ethylene glycol and lower monohydric alcohols are prepared from syn gas in improved yields by contacting a mixture of carbon monoxide and hydrogen with a catalyst system comprising a ruthenium-containing compound and a special manganese-containing compound, both dispersed in a low melting quaternary phosphonium compound, and heating the resulting reaction mixture at a temperature of at least 150.degree. C. and a pressure of at least 500 psi for sufficient time to produce the desired ethylene glycol and monohydric alcohols, and then recovering the same from the reaction mixture.
29.
US Patent 4,551,565 / Miyazaki , et al. / November 5, 1985
Abstract
In a process for producing ethylene glycol and/or a glycollic acid ester by the vapor phase catalytic hydrogenation of an oxalic acid diester in the presence of a catalyst and hydrogen gas, the improvement wherein the catalyst has the following composition formula wherein k, p and q represent gram-atoms of Mo, Ba and O, respectively, per gram-atom of Cu, k is a number of from 0 to 3, p is a number of from 0 to 6, and q is a number determined depending upon the atomic valence and gram-atoms of Cu, Mo and Ba, provided that k and p are not zero at the same time; and the aforesaid catalyst.
30.
US Patent 4,087,470 / Suzuki / May 2, 1978
Abstract
A cyclic process for producing ethylene glycol comprising the steps of: (1) contacting formaldehyde with a synthesis gas comprising carbon monoxide and hydrogen in the presence of a catalytic amount of hydrogen fluoride under conditions effective to deplete carbon monoxide from the synthesis gas and produce glycolic acid and diglycolic acid; (2) contacting the acid product of step (1) with ethylene glycol, diethylene glycol, or mixtures thereof under conditions effective to produce ethylene glycol glycolate and diglycolate, diethylene glycol glycolate and diglycolate, or mixtures thereof; (3) removing residual carbon monoxide from the carbon monoxide depleted synthesis gas of step (1) thereby producing a hydrogen rich gas; (4) contacting the glycolate and diglycolate product of step (2) with the hydrogen-rich gas mixture of step (3) under conditions effective to produce ethylene glycol, diethylene glycol, or mixtures thereof; and (5) recycling from step (4) to step (2) an amount of the glycol product effective to esterify substantially all the acid product present in the reaction zone of step (2).
31.
US Patent 4,112,245 / Zehner , et al. / September 5, 1978
Abstract
A process for the preparation of ethylene glycol by the vapor phase hydrogenation of oxalate esters, such as a dibutyl oxalate, at elevated temperatures and at relatively low hydrogen pressures in the presence of a suitable hydrogenation catalyst, such as a copper chromite catalyst, while minimizing the hydrogenolysis of the glycol and other side reactions and maximizing the hydrogenation catalyst activity.
32.
US Patent 4,533,774 / Griggs / August 6, 1985
Abstract
Ethylene glycol is produced by reacting at elevated temperature methanol, a polymeric source of formaldehyde and an organic peroxide having the formula R--O--O--R.sup.1 wherein R and R.sup.1 are independently either alkyl or aralkyl groups containing from 3 to 12 carbon atoms. The polymeric source of formaldehyde is preferably paraformaldehyde.
33.
US Patent 4,412,085 / Kollar / October 25, 1983
Abstract
Ethylene glycol is prepared by reacting methanol, formaldehyde and from greater than 6 to about 25 weight percent of an organic peroxide in the presence of about 0.5 to about 35 weight percent of water based on the feed composition, the amount of water within said range being correlated with the peroxide content. The organic peroxide has the formula R--O--O--R.sup.1 wherein R and R.sup.1 are each an alkyl or aralkyl group having 3 to 12 carbon atoms.
23.
US Patent 4,337,371 / Kollar / June 29, 1982
Abstract
Ethylene glycol is prepared by reacting methanol, formaldehyde and no more than 6 weight percent based on the feed composition of an organic peroxide in the presence of water. The organic peroxide has the formula R-O-O-R.sup.1 wherein R and R.sup.1 are each an alkyl or aralkyl group having 3 to 12 carbon atoms.
24.
US Patent 4,412,084 / Kollar / October 25, 1983
Abstract
In the preparation of ethylene glycol by reacting methanol, formaldehyde and an organic peroxide, improved yields of ethylene glycol are achieved by the reaction of portions of the total amounts of formaldehyde and peroxide to be reacted with methanol. Formaldehyde and peroxide are incrementally added to a liquid medium containing methanol in controlled amounts during the reaction to permit conversion of each portion of said formaldehyde and peroxide reactants prior to the next addition. The portions are added such that the concentration of glycol in the reaction medium to which a later portion is added is greater than that to which an earlier portion is added. The reaction is continued until all the formaldehyde and peroxide has been incrementally added to the reaction medium and subjected to reaction conditions for a suitable period of time.
25.
US Patent 4,393,252 / Kollar / July 12, 1983
Process for producing ethylene glycol
Abstract
Ethylene glycol is prepared by reacting methanol and an organic peroxide of the formula R--O--O--R.sub.1, wherein R and R.sub.1 are each an alkyl or aralkyl group having 3 to 12 carbon atoms, in the presence of a minor amount of a basic material. Preferably, formaldehyde is present as a reactant in the presence of water. The presence of the basic material reduces the hydrogen ions which are formed and thus reduces the amount of methylal produced.
26.
US Patent 4,356,332 / Knifton / October 26, 1982
Abstract
This invention pertains to the production of ethylene glycol by reaction of formaldehyde with carbon monoxide and hydrogen in the presence of a catalyst comprising a cobalt-containing compound and a tin-or germanium-containing promoter and in the presence of substantially inert, oxygenated hydrocarbon solvent.
27.
US Patent 4,518,715 / Knifton / May 21, 1985
Abstract
This invention concerns a process for preparing ethylene glycol and lower monohydric alcohols comprising contacting a mixture of carbon monoxide and hydrogen with a catalyst comprising a ruthenium-containing compound and a copper- or silver-containing compound, both dispersed in a low-melting quaternary phosphonium salt and heating the resulting mixture at an elevated temperature and moderate pressure for sufficient time to produce the desired ethylene glycol.
28.
US Patent 4,434,246 / Simons / February 28, 1984
Abstract
Ethylene glycol and lower monohydric alcohols are prepared from syngas in good yield by contacting a mixture of carbon monoxide and hydrogen with a catalyst system comprising a ruthenium-containing compound and a special substituted aromatic compound both dispersed in a low melting quaternary phosphonium salt and heating the resulting mixture at a temperature of at least 150.degree. C. and a pressure of at least 500 psi for sufficient time to produce the desired ethylene glycol and monohydric alcohols, and then removing the same from the reaction mixture.
29.
US Patent 4,315,993 / Knifton / February 16, 1982
Abstract
A process for preparing ethylene glycol wherein a mixture of carbon monoxide and hydrogen is contacted at an elevated temperature and pressure and in the presence of a solvent with a ruthenium compound and a promoter, such as pyrocatechol. In another aspect this invention relates to the preparation of ethylene glycol ethers from carbon monoxide and hydrogen.
30.
US Patent 4,434,247 / Dombek / February 28, 1984
Abstract
This invention relates to the manufacture of valuable alcohols containing 1 to 2 carbon atoms, especially glycol and ethanol from the reaction of hydrogen and carbon monoxide, by a homogeneous catalytic process using as a catalyst a solubilized ruthenium carbonyl complex. The invention also encompasses the catalyst formed during the process. A particular desirable embodiment of the invention is the continuous operation thereof in a manner which minimizes inhibition of glycol formation and represses formation of adverse or undesirable glycol byproducts.
31.
US Patent 4,412,085 / Kollar / October 25, 1983
Abstract
Ethylene glycol is prepared by reacting methanol, formaldehyde and from greater than 6 to about 25 weight percent of an organic peroxide in the presence of about 0.5 to about 35 weight percent of water based on the feed composition, the amount of water within said range being correlated with the peroxide content. The organic peroxide has the formula R--O--O--R.sup.1 wherein R and R.sup.1 are each an alkyl or aralkyl group having 3 to 12 carbon atoms.
32.
US Patent 4,412,084 / Kollar / October 25, 1983
Abstract
In the preparation of ethylene glycol by reacting methanol, formaldehyde and an organic peroxide, improved yields of ethylene glycol are achieved by the reaction of portions of the total amounts of formaldehyde and peroxide to be reacted with methanol. Formaldehyde and peroxide are incrementally added to a liquid medium containing methanol in controlled amounts during the reaction to permit conversion of each portion of said formaldehyde and peroxide reactants prior to the next addition. The portions are added such that the concentration of glycol in the reaction medium to which a later portion is added is greater than that to which an earlier portion is added. The reaction is continued until all the formaldehyde and peroxide has been incrementally added to the reaction medium and subjected to reaction conditions for a suitable period of time.
33.
US Patent 4,400,559 / Bhise / August 23, 1983
Process for preparing ethylene glycol
Abstract
Ethylene glycol is prepared by a process in which ethylene oxide is extracted from an aqueous solution with near-critical or super-critical carbon dioxide. Thereafter an ethylene oxide--carbon dioxide--water mixture is contacted with a catalyst to form ethylene carbonate, which is then hydrolyzed to ethylene glycol in the presence of the same catalyst. The ethylene glycol is separated as product and the carbon dioxide and the catalyst are recycled.
34.
US Patent 4,393,252 / Kollar / July 12, 1983
Abstract
Ethylene glycol is prepared by reacting methanol and an organic peroxide of the formula R--O--O--R.sub.1, wherein R and R.sub.1 are each an alkyl or aralkyl group having 3 to 12 carbon atoms, in the presence of a minor amount of a basic material. Preferably, formaldehyde is present as a reactant in the presence of water. The presence of the basic material reduces the hydrogen ions which are formed and thus reduces the amount of methylal produced.
35.
US Patent 4,387,255 / Wood / June 7, 1983
Abstract
Process for production of ethylene glycol comprising contacting a nonflammable feed comprising ethylene, molecular oxygen and water with a catalyst comprising iodine under reaction conditions in a reaction zone in which there is maintained a partial pressure of ethylene that is effective to yield ethylene glycol without substantial acetaldehyde generation. In a preferred embodiment, ethylene glycol is removed from the reaction zone at a rate effective to minimize formation of condensed glycol by-products.
36.
US Patent 4,345,104 / Cropley / August 17, 1982
Abstract
A process for preparing ethylene glycol by the oxidative coupling of methanol in the vapor state.
37.
US Patent 4,337,371 / Kollar / June 29, 1982
Abstract
Ethylene glycol is prepared by reacting methanol, formaldehyde and no more than 6 weight percent based on the feed composition of an organic peroxide in the presence of water. The organic peroxide has the formula R-O-O-R.sup.1 wherein R and R.sup.1 are each an alkyl or aralkyl group having 3 to 12 carbon atoms.
38.
US Patent 4,317,946 / Costa / March 2, 1982
Abstract
A process is provided for catalytic hydrogenation of glycolaldehyde to form ethylene glycol in liquid phase employing a homogeneous ruthenium carboxylate complex catalyst system. Ethylene glycol is produced in excellent yields and selectivities and the process permits use of mild temperature and pressure conditions. The formation of acetals is greatly minimized as compared to prior art ruthenium catalysts.
39.
US Patent 4,265,828 / Knifton / May 5, 1981
Abstract
This invention concerns a process of making ethylene glycol which comprises the steps of contacting a mixture of CO and H.sub.2 with a catalyst system comprising a ruthenium-containing compound dispersed in a low melting quaternary phosphonium or ammonium base or salt, and heating said resultant reaction mixture under a pressure of 500 psi or greater at a temperature of at least 150.degree. C. for a sufficient time to provide said ethylene glycol.
40.
US Patent 4,209,650 / Onsager , et al./ June 24, 1980
Abstract
Ethylene glycol is prepared by the reaction of ethylene, molecular oxygen and water in the presence of an iodine catalyst and in the presence of a copper co-catalyst or promoter.
41.
US Patent 4,061,868 / Fumagalli , et al. / December 6, 1977
Process for the manufacture of glycols and glycol nono-esters
Abstract
There is provided an improvement in the process for the preparation of organic monoesters of vicinal glycols and the corresponding free glycols by reacting an olefin with oxygen, water and a carboxylic acid, in the liquid phase, at an initial pH of lower than 7, the improvement comprising contacting the reaction mixture with a catalyst system consisting essentially of (i) iodine or an iodine compound selected from the group consisting essentially of copper iodide, manganese iodide, cerium iodide, an alkali metal iodide, an alkali earth metal iodide and the iodohydride of the olefin, (ii) a copper compound selected from the group consisting essentially of copper oxide, copper hydroxide, copper carbonate, copper iodide, and a copper salt of the carboxylic acid, and (iii) an activating ion selected from the group consisting of manganese cation, cerium cation, an alkali metal cation, an alkaline earth metal cation, nitric anion or a mixture of any of the foregoing, wherein the molar ratio of the carboxylic acid to water is lower than 1, the molar ratio of copper to water is equal to or lower than 2 moles of copper per 100 moles of water, and the molar ratio of iodine to copper is lower than 1.
42.
US Patent 4,087,470 / Suzuki / May 2, 1978
Abstract
A cyclic process for producing ethylene glycol comprising the steps of: (1) contacting formaldehyde with a synthesis gas comprising carbon monoxide and hydrogen in the presence of a catalytic amount of hydrogen fluoride under conditions effective to deplete carbon monoxide from the synthesis gas and produce glycolic acid and diglycolic acid; (2) contacting the acid product of step (1) with ethylene glycol, diethylene glycol, or mixtures thereof under conditions effective to produce ethylene glycol glycolate and diglycolate, diethylene glycol glycolate and diglycolate, or mixtures thereof; (3) removing residual carbon monoxide from the carbon monoxide depleted synthesis gas of step (1) thereby producing a hydrogen rich gas; (4) contacting the glycolate and diglycolate product of step (2) with the hydrogen-rich gas mixture of step (3) under conditions effective to produce ethylene glycol, diethylene glycol, or mixtures thereof; and (5) recycling from step (4) to step (2) an amount of the glycol product effective to esterify substantially all the acid product present in the reaction zone of step (2).
43.
US Patent 3,940,432 /
Abstract
This invention is concerned with improving the ethylene glycol production capabilities of the metal carbonyl catalyzed reaction between carbon monoxide and hydrogen by conducting the reaction such that the ethylene glycol concentration in the reaction mixture is less than 5 gram moles per liter, preferably between about 0.4 to 5 gram moles per liter of reaction mixture and the molar formation ratio between ethylene glycol and methanol in the reaction mixture exceeds about 0.3. In a preferred embodiment, a continuous process is operated in such a manner that the concentration of ethylene glycol in the product mixture removed from the reactor is greater than the average concentration of ethylene glycol in the reactor.
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