Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C67/00—Preparation of carboxylic acid esters
  • C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
  • C07C67/11—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond being mineral ester groups
• • C—CHEMISTRY; METALLURGY
  • C01—INORGANIC CHEMISTRY
  • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
  • C01B7/00—Halogens; Halogen acids
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C17/00—Preparation of halogenated hydrocarbons
  • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
  • C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
  • C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
  • C07C29/095—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of organic acids

Definitions

• the disclosure relates to a method of making alcohols, and more specifically alkanols, from alkanes, and more specifically from alkane halides.
• Alcohols are industrially produced from direct hydration of alkenes, such as ethylene, or from cracking of appropriate fractions of distilled (or fractionated) crude oil. While demands for alcohols, and especially for ethanol, continue to increase, crude oil reserves continue to be depleted. Moreover, the processes of alkene hydration and fractionation and cracking of crude oil are themselves energy intensive processes.
• the disclosure provides a method of making alcohols. More
• an illustrative disclosed method comprises reacting an alkane gas with a halogen gas in a halogenation reactor to form a halogenation reaction product mixture comprising alkane halide and hydrogen halide mixture;
• the disclosed method involves liquid phase forming of alcohol esters from liquid alkane halides and a solution of metal salts of organic acids whose alkanes esters are less soluble in water than that of the alkane halide and treating of the alcohol ester formed with magnesium or metal hydroxides to form the alcohol and the metal salt of the organic acids.
• FIG. 1 is a schematic diagram of one embodiment of the disclosed process.
• FIG. 2 is a schematic diagram of an alternative illustrative method of the disclosed process.
• FIG. 3 is a schematic diagram of another aspect of the method of the disclosed process.
• the disclosure is a method for making alcohols.
• the disclosure is a method for producing organic alcohols, including for example, methanol, ethanol, propanol, and combinations thereof.
• the instant disclosure provides a method comprising: reacting an alkane with a halogen gas in a halogenations reactor to form a halogenation reaction product mixture comprising alkane halide and hydrogen halide mixture; contacting the halogenation reaction product mixture with a metal organic salt thereby forming an extractor product mixture of a metal halide, organic salt, organic ester, and organic acid; separating the organic ester and organic acid mixture from the metal halide; oxygenating the metal halide to form a metal oxide and halide containing gasses; separating the metal oxide from the halide containing gasses; mixing the metal oxide with water to form a metal oxide slurry; mixing the metal oxide slurry with a countercurrent flow of the organic ester and organic acid mixture to form a raw product comprising alkanol and a metal organic salt.
• the instant disclosure provides a method comprising: reacting an alkane with a halogen gas in a halogenations reactor to form a halogenation reaction product mixture comprising alkane halide and hydrogen halide mixture; contacting the halogenation reaction product mixture with a metal organic salt under aqueous conditions thereby forming an aqueous extractor product mixture of a soluble metal halide, and an insoluble organic ester; separating the insoluble organic ester from the aqueous metal halide; oxygenating the metal halide to form a metal oxide and halide containing gasses; separating the metal oxide from the halide containing gasses; mixing the metal oxide with water to form a metal oxide slurry; mixing the metal oxide slurry with a countercurrent flow of the insoluble organic ester and insoluble organic salt mixture to form a raw product comprising alkanol.
• the instant disclosure provides a method for the production of alcohols comprising: contacting an alkane gas with an aqueous halide saturated solution to strip the halide from the solution to form a product mixture of an alkane and a halide; reacting a halogen gas with the alkane halide mixture to form an alkyl halide, an alkyl di halide, an alkyl tri halide, and a hydrogen halide gasses; neutralizing the alkyl di halide, the alkyl tri halide, and the hydrogen halide gasses with a suspension of magnesium hydroxide; cooling the gasses from the neutralizing step to a temperature to liquefy the gasses to form liquefied gasses; mixing the liquefied gasses with a magnesium benzoate or butyrate solution to form an aqueous solution of benzoate or butyrate ethyl esters;
• Alkanes useful in various embodiments of the disclosed methods may be selected from the group consisting of C1-C20 alkanes, including most preferably, methane, ethane, propane, butane and mixtures thereof. All combinations and subcombinations of such alkanes are included and disclosed herein.
• the alkanes may comprise a mixture of methane and ethane; or in the alternative, a mixture of methane and propane; or in the alternative, a mixture of ethane and butane.
• the alkane may comprise only a single alkane.
• the alkane may comprise methane with no other alkane component; or in the alternative, the alkane may comprise ethane with no other alkane component; or in the alternative the alkane may comprise propane with no other alkane component.
• Halogen gasses useful in various embodiments of the disclosed methods may be selected from the group consisting of chlorine gas, bromine gas, iodine gas, and combinations thereof. All combinations and subcombinations of such halogen gasses are included and disclosed herein.
• the halogen gasses may comprise a mixture of chlorine and bromine gasses; or in the alternative the halogen gasses may comprise a mixture of chlorine and iodine gasses.
• the halogen gas useful in the halogenations step of the disclosed method may comprise only a single halogen gas.
• the halogen gas may be bromine gas; or in the alternative, the halogen gas may be chlorine gas.
• the halogen gas or gasses used in the halogenation reactor may be supplied directly into the halogenations reactor, as for example, by injection through a dedicated supply line.
• the halogen gas or gasses used in the halogenation reactor may be formed in situ in the halogenation reactor.
• Metal organic salts useful in the disclosed method of FIG. 1 may be selected from the group consisting of metal formate, metal acetate, metal benzoate, and combinations thereof.
• the metal of the metal organic salt in various embodiments of the disclosed method of FIG. 1 may be selected from Magnesium, Zinc, and combinations thereof, for example. All combinations and subcombinations of the metal organic salts are disclosed and included herein.
• the metal organic salt may be magnesium formate, zinc acetate, magnesium benzoate, zinc dichlorobenzoate, zinc dichloroacetate, or any combination of two or more of the foregoing.
• Metal organic salts useful in the improvement methods disclosed below are selected based on the water solubility of the alkane halide with which the metal organic salt is reacted and the alkane ester product resulting from that reaction in water. Specifically, if the alkane ester product has a solubility that is less than the solubility of the reactant alkane halide, then the alkane ester product will precipitate out of the water into an insoluble layer which can be easily separated from the metallic halide which remains in the water. This separation of insoluble alkane ester from the metallic halide permits the metallic halide to be processed downstream independent from the alkane ester stream to form the metallic hydroxide required to be contacted with the alkane ester to form the alkane alcohol.
• the metal organic salt may be a magnesium benzoate or a magnesium butyrate or a magnesium salicylate, for example, which are the magnesium salts of benzoic acid, butyric acid, and salicyclic acid, respectivily.
• the solubility of the ethyl bromide in water is 0.91 grams per 100 ml of water, or 0.0835 moles per 1000 ml of water and the solubility of ethyl butyrate is 0.68 grams per 100 ml of water or 0.059 moles per 1000 ml. Because the solubility of the ethyl butyrate is less than the solubility of the magnesium butyrate in water, the ethyl butyrate will precipitate out of the water as an insoluble layer according the teachings of this disclosure.
• the solubility of the methyl formate is greater than the solubility of the ethyl bromide and hence the methyl formate will remain with the ethyl bromide in the aqueous solution.
• the alkane is methane
• the metal organic salt is magnesium formate
• the halide gas is bromine gas
• the alkanol is methanol.
• the disclosure provides a method of making alkanols except that the halogen gas is chlorine gas.
• the disclosure provides a method of making alkanols except that the halogen gas is a mixture of bromine and chlorine gasses.
• the disclosure provides a method of making alkanols except that the alkane is ethane.
• the disclosure provides a method of making alkanols except that the alkane is propane.
• the disclosure provides a method of making alkanols except that the alkane is butane.
• the disclosure provides a method of making alkanols except that the alkane is a mixture of methane and ethane.
• the invention provides a method of making alkanols except that the metal organic salt is magnesium acetate.
• the invention provides a method of making alkanols except that the metal organic salt is magnesium benzoate.
• the invention provides a method of making alkanols except that the metal organic salt is zinc benzoate.
• the invention provides a method of making alkanols except that the metal organic salt is magnesium acetate. In an alternative embodiment of FIG. 1, the invention provides a method of making alkanols except that the metal organic salt is zinc formate.
• the various steps of the disclosed method may be conducted in any appropriate reactor.
• the step of oxygenating the metal halide may occur in a fluidized bed reactor, otherwise known as. a fluo-solids reactor.
• the step of contacting the halogenation reaction product mixture with a metal organic salt occurs in a column packed with an inert packing material. Any one or more inert materials as are known in the art may be used in the step of contacting the halogenations reaction product mixture with a metal organic salt may be used, including for example Berl saddles.
• the step of contacting the halogenation reaction product mixture with a metal organic salt solution occurs by flowing the halogenation reaction product mixture against a countercurrent flow of the metal organic salt.
• the disclosed methods further comprises stripping the bromine from the bromine containing gasses and recycling the bromine into the halogenations reactor in the case of FIG. 1 and a brominator reactor in the case of FIG. 2.
• the alkane to halogen gas molar ratio may be greater than 2: 1. All individual values and subranges greater than a 2: 1 ratio are included herein and disclosed herein; for example, the alkane to halogen gas molar ration can be from a lower limit of 2: 1, 2.2: 1, 2.4: 1, 2.6: 1, 2.8: 1, 3: 1, 3.5: 1, 3.8: 1, 4: 1 ; 4.2:1. In at least one aspect of the present disclosure the alkane to halogen gas molar ratio is greater than or equal to 4: 1.
• the halogenations step in all the methods wherein the alkane and halogen gas are reacted to form an alkane halide and the hydrogen halide is, in some embodiments of the disclosed methods, autocatalytic following initiation.
• the halogenations reaction may be initiated by application of heat to a temperature between 350 and 450. degree. C. All individual values and subranges from 350 and 450. degree. C. are included herein and disclosed herein; for example, the halogenation reaction initiation temperature can be from a lower limit of 350, 360, 370, 380, 390, 400, 410, 420, 430, or 440.degree. C.
• the halogenation reaction initiation temperature may be in the range of from 350 to 380.degree. C., or in the alternative, halogenation reaction initiation temperature may be in the range of from 380 to 400.degree. C., or in the alternative, the halogenation reaction initiation temperature may be in the range of from 400 to 450.degree. C.
• the halogenations reaction may be initiated at lower temperatures in the presence of ultraviolet radiation.
• the halogenations reaction initiation temperature may be in the range from 250 to 350. degree. C. All individual values and subranges from 250 and 350.degree. C. are included herein and disclosed herein; for example, the halogenation reaction initiation temperature can be from a lower limit of 250, 260, 270, 280, 290, 300, 310, 320, 330, or 340.degree. C. to an upper limit of 260, 270,280, 290, 300, 310, 320, 330, 340 or 350.degree. C.
• the halogenation reaction initiation temperature may be in the range of from 250 to 280.degree. C, or in the alternative, halogenation reaction initiation temperature may be in the range of from 280 to 300.degree. C, or in the alternative, the halogenation reaction initiation temperature may be in the range of from 300 to 350.degree. C.
• the heat generated by the halogenation reaction is sufficient to maintain the halogenation reaction.
• natural gas comprising methane enters a mixing chamber 1 through line 2 in which it is mixed with bromine vapor entering mixing chamber 1 through line 3.
• the natural gas/bromine vapor mixture passes into the halogenations reactor 5 wherein methyl bromide and hydrobromic acid are formed.
• the halogenations reaction product mixture which may further comprise unreacted gasses passes through line 6 to condenser 7 wherein the mixture is cooled. Following cooling the halogenation reaction product mixture is passed through line 8 and flowed upward into extractor 9 through an inert packing material 10 (not shown) against a counterflow of magnesium formate solution which enters extractor 9 through line 38.
• Magnesium bromide is formed and magnesium bromide solution exits extractor 9 through line 11. Also formed in extractor 9 is methyl formate and formic acid gasses which exit extractor 9 through line 12. Magnesium bromide solution enters reactor 13 wherein it is heated and reacted with oxygen entering through line 16. Bromine containing gasses are led from reactor 13 through line 17 to cooler 18 where most of the bromine is recovered and exits cooler 18 through line 19. Gasses containing traces of bromine are led from cooler 18 to absorber 20 through line 21 wherein the gasses are contacted with a counterflow of solvent, thereby recovering the remainder of the bromine. Bromine free gasses may be vented or otherwise routed through line 22.
• the bromine containing solvent exits the bottom of absorber 20 and enters the top of stripper 23 through line 24.
• the bromine containing solvent is contacted with methane entering the stripper 23 through line 39, thereby stripping the bromine from the bromine containing solvent.
• Stripped solvent may be recovered from the bottom of stripper 23 and pumped using pump 26 through line 28 into the top of absorber 20.
• Magnesium oxide from oxidation reactor 13 enter reactor 29 through line 30. Water is added to reactor 29 through line 31.
• a slurry of magnesium oxide is formed in reactor 29 and is passed through line 32 into the top of stripper 33 wherein the magnesium oxide slurry is contacted with a counterflow of methyl formate and formic acid gasses.
• stripper 33 methanol is formed and exits stripper 33 to condenser 34.
• Condenser 34 cools the methanol which is collected through line 35.
• Gas products of stripper 33 which are substantially free of methanol are passed into mixing chamber 1 through line 36.
• Magnesium formate solution leaves stripper 33 through line 38 through which it is passed into extractor 9.
• the magnesium bromide, the liquid metallic halide in line 11 is separated from the liquid methyl formate, the alkane ester, under gaseous conditions in extractor 9 in Example 1 as follows:
• Alkane Ester (g) + Metallic Halide (1) which allows for the processing of the liquid magnesium bromide by oxidation reactor 13 and reactor 29 for the formation of the slurry of magnesium oxide found in line 6 required to form the methyl alkanol. More specifically, the alcohol is formed by reaction of the liquid magnesium hydroxide, the liquid metallic hydroxide in line 6, and methyl formate gas, the alkane ester gas in line 12 to form the liquid metallic salt, the metal ester in line 38, and the methanol gas, the alkane alcohol that enter condenser 34 for condensation and recover as follows:
• the reaction advantageously occurs under conditions such that the alkane esters formed are insoluble in the aqueous solution containing the liquid alkane halides and the liquid metal organic salt as the reactants. This allows for the separation of the liquid alkane esters from the liquid metallic halide so that the liquid metallic halide can be further processed into the slurry of metallic oxides that may be reacted with the liquid ester to form the alkane alcohol.
• the alkane halides that are contacted with the metallic organic salt in the Improvement Examples are selected such that the alkane esters formed from the reaction of the alkane halide and the metallic organic salt have a solubility in water that is less than the solubility of the alkane halide in water. If the alkane ester product has a solubility that is less than the solubility of the reactant alkane halide, then the alkane ester product will precipitate out of the water into an insoluble layer which can be easily separated from the metallic halide which remains in the water.
• This separation of insoluble alkane ester from the metallic halide permits the metallic halide to be processed downstream independent from the alkane ester stream to form the metallic hydroxide required to be contacted with the alkane ester to form the alkane ethanol. If, however, the alkane ester product has a solubility that is greater than the solubility of the reactant alkane halide, the alkane ester product will not precipitate out of the water but remain with the metallic halide as a mixture in the water; making the reaction of the metallic halide into metallic hydroxide not possible.
• Improvement Example 1 uses the same process and equipment as shown in FIG. 1 except that equipment 9 which is an extractor in the Example 1 is replaced with a separator in Example 2 for the purpose of separating alkane esters from metal halides in the mix of products that is formed in the separator.
• the alkane esters in Improvement Example 1 are formed from the reaction of the liquid alkane halide and the metallic organic salt, such that the reaction advantageously occurs under conditions such that the alkane esters formed are insoluble in the aqueous solution containing the liquid alkane halides and the liquid metal organic salt as the reactants. More specifically, the alkane esters formed in separator 9 in Improvement Example 1 are chosen to have a solubility in water that is less than the solubility of the alkane halide in water.
• the alkane ester remains as a liquid in the product mix in this reaction.
• an ethyl butyrate is used as the alkane ester.
• ethyl bromide is the alkane halide of choice as the alkane halide for use as a reactant to the metallic organic salt according to the following reaction occurring in separator 9: (5) Metallic Butyrate (1) + Ethyl Bromide (1) »-
• the solubility of the ethyl bromide (i.e., which reacts with the metallic organic salt to form the alkane ester according to chemical equation 5 above) in water is 0.91 grams per 100 ml of water, or 0.0835 moles per 1000 ml of water which is greater than the solubility of ethyl butyrate in water which is 0.68 grams per 100 ml of water or 0.059 moles per 1000 ml.
• the solubility of the ethyl butyrate (i.e., the alkane ester) in water is less than the solubility of its reactant ethyl bromide (i.e., its alkane halide reactant) in water.
• liquid ethyl butyrate in a liquid phase in separator 9. Since liquid ethyl butyrate is insoluble in water, the liquid ethyl butyrate advantageously forms an insoluble layer with the aqueous magnesium bromide solution layer. This allows the liquid ethyl butyrate to be
• an methyl benzoate is used as the alkane ester.
• ethyl methyl benzoate is chosen as the alkane halide for use as a reactant to the metallic organic salt according to the following reaction occurring in separator 9:
• the solubility of the methyl benzoate (i.e., the alkane ester) in water is less than the solubility of its reactant methyl bromide (i.e., its alkane halide reactant) in water.
• methyl benzoate i.e., the alkane ester
• its reactant methyl bromide i.e., its alkane halide reactant
• the methyl formate remains in the aqueous metal hydroxide solution in liquid separator 9 as a solvent which prevents the magnesium bromide solution to be processed into the magnesium oxide slurry in line 32 required for reaction to form the methanol.
• the solubility of the methyl formate was not less than the solubility of its reactant methyl bromide, there is no methyl formate product in line 12 for use in forming the methanol in stripper 33.
• Example 1 there was a gaseous methyl formate product formed in line 12 for use in the methanol production reaction in stripper 33 because the extractor 9 evaporates the methyl formate from the magnesium bromide solution to create the required separation between the magnesium bromide and the methyl formate in extractor 9.
• bromine is produced in fluo-solids reactor 1.
• the bromine vapor passes through line 3 to condenser 2 where most of the bromine, typically up to about 95%, for example, may be is condensed.
• the uncondensed bromine vapor passes through line 5 to absorber 4 and is flowed against a counterflow of water. Clean gasses from the cross-flow are vented to the atmosphere through line 6.
• Water saturated with bromine forming an aqueous bromine saturated solution passes through line 8 to extractor 7.
• extractor 7 the aqueous bromine saturated solution flows against a counterflow of ethane gas which strips all, or substantially all, of the bromine from the water.
• the ethane containing the stripped bromine passes through line 9 to brominator reactor 10.
• Liquid bromine from condenser 2 passes through line 11 to vaporizer 12 where the liquid bromine is vaporized and preheated before passing through line 13 to brominator reactor 10.
• Bromine and ethane in brominator reactor 10 react to form ethyl bromide, ethyl dibromide, ethyl tri bromide, and hydrogen bromide gasses.
• These gasses exiting reactor 10 pass through line 15 to neutralizing reactor 14 where ethyl di-bromide, ethyl tri -bromide, and hydrogen bromide are neutralized with a suspension of magnesium hydroxide flowing through line 19 from reactor 18.
• Liquids from neutralizing reactor 14 pass through line 32 to fluo solids reactor 1.
• Gasses from neutralizing reactor 14 pass through line 20 to condenser 12 where the gasses are cooled.
• the phase 2 insoluble ester layer contacts a suspension of magnesium hydroxide which enters distillation reactor 29 through line 41 from reactor 18.
• Alcohol (ethanol) from distillation reactor 29 is recovered as product through line 31.
• Magnesium hydroxide flows from reactor 18 to brominator reactor 10 and distillation reactor 29.
• the alkane halides that are contacted with the metallic organic salt in intensive mixer 23 are selected such that the alkane esters formed in intensive mixer 23 have a solubility in water that is less than the solubility of the alkane halide in water. If the alkane ester product has a solubility that is less than the solubility of the reactant alkane halide, then the alkane ester product will precipitate out of the water into an insoluble layer which can be easily separated from the metallic halide which remains in the water.
• This separation of insoluble alkane ester from the metallic halide permits the metallic halide to be processed downstream independent from the alkane ester stream to form the metallic hydroxide required to be contacted with the alkane ester to form the alkane alcohol. If, however, the alkane ester product has a solubility that is greater than the solubility of the reactant alkane halide, the alkane ester product will not precipitate out of the water but remain with the metallic halide as a mixture in the water; making the reaction of the metallic halide into metallic hydroxide not possible.
• the organic ester flowing on line 28 in Example 3 from decanter 27 to distillation reactor 29 is a liquid; just as the organic ester flowing into stripper 33 on line 12 in Example 2 is a liquid.
• the liquid organic ester may enable the use of smaller equipment in the process, eliminate the need for a gas pump, have lower energy requirements, be less expensive and produce more alcohol output per unit volume than is possible using the method of Example 1.
• FIG. 3 An illustrative alternative method for the production of alcohols is shown in FIG. 3 and includes the steps of reacting,: 1. producing a halogen gas in a fluo -solids reactor 101, solids comprising a metal and a halogen forms a halogen gas and a metal oxide;
• the liquid halogen may be vaporized in vaporizer 112 and fed to a brominator 110;
• condenser 121 condensing a portion of the neutralized gasses in condenser 121 forming a condensate and a gas
• the metals comprised in the solids fed to fluo solids reactor 101 comprises magnesium.
• the metal oxide fed to reactor 118 from fluo solids reactor 101 comprises MgO.
• the metal hydroxide fed to neutralizer 114 and distiller/reactor 129, from reactor 118, comprises MgOH.
• the metal benzoate or butyrate fed from distiller/reactor 129 comprises magnesium benzoate or butyrate.
• the halogens comprised in the solids fed to fluo solids reactor 101 comprises bromine.
• the halogens fed to brominator 110 comprise bromine.
• the alkane fed to extractor 107 comprises ethane.
• the halogen and alkane fed to brominator 110, from extractor 107 comprises ethane.
• the halogens comprised in the solids fed to fluo solids reactor 101 comprises bromine and the metals comprised in the solids fed to fluo solids reactor 101 comprises magnesium.
• the phase 1 liquid fed to fluo solids reactor 101, from decanter 127 comprises MgBr 2 .
• the method disclosed in connection with Improvement Example 5 involves liquid phase forming of alcohol esters from liquid alkane halides and a solution of metal salts of organic acids whose alkanes esters are less soluble in water than that of the alkane halide and treating of the alcohol ester formed with magnesium or metal hydroxides to form the alcohol and the metal salt of the organic acids.
• a method of making alcohols may involve forming of alcohol esters from liquid alkane halides and a solution of metallic salts of organic acids to produce gaseous alcohol esters for reaction with magnesium or metal hydroxides to form the alcohol and the metal salt of the organic acids.
• liquid phase alcohol esters instead of gaseous alcohol esters are produced from liquid alkane halides and a solution of metal salts of organic acids whose alkane esters are less soluble in water than that of the alkane halide and treating of the alcohol ester formed with magnesium or metal hydroxides to form the alcohol and the metal salt of the organic acids.
• the disclosed methods have wide use for producing alcohols from more readily available starting materials and may provide efficiencies in energy input requirements and costs over current industrial alcohol production from direct hydration of alkenes, or from cracking of appropriate fractions of distilled (or fractionated) crude oil.
• the disclosed improvement methods illustrated by the Improvement Examples in connection with FIG. 1 and the methods disclosed in connection with FIGS. 2 and 3 involve liquid phase forming of alcohol esters from liquid alkane halides and a solution of metal salts of organic acids whose alkanes esters are less soluble in water than that of the alkane halide and treating of the alcohol ester formed with magnesium or metal hydroxides to form the alcohol and the metal salt of the organic acids.
• the liquid organic ester may enable the use of smaller equipment in the process, eliminate the need for a gas pump, have lower energy requirements, be less expensive and produce more alcohol output per unit volume than is possible using the method of Original Example 1.

Landscapes

• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Inorganic Chemistry (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Priority Applications (9)

Applications Claiming Priority (1)

Publications (1)

Family

ID=48947862

Family Applications (1)

Country Status (9)

Families Citing this family (1)

Citations (3)

Family Cites Families (3)

• 2012
  • 2012-02-08 CA CA2862300A patent/CA2862300A1/en not_active Abandoned
  • 2012-02-08 CN CN201280069205.4A patent/CN104114523A/zh active Pending
  • 2012-02-08 MX MX2014009587A patent/MX2014009587A/es unknown
  • 2012-02-08 AU AU2012369143A patent/AU2012369143A1/en not_active Abandoned
  • 2012-02-08 EA EA201491476A patent/EA201491476A1/ru unknown
  • 2012-02-08 EP EP12867889.3A patent/EP2812301A4/en not_active Withdrawn
  • 2012-02-08 WO PCT/US2012/024382 patent/WO2013119230A1/en active Application Filing
  • 2012-02-08 IN IN6193DEN2014 patent/IN2014DN06193A/en unknown
  • 2012-02-08 BR BR112014019473A patent/BR112014019473A8/pt not_active IP Right Cessation

Patent Citations (3)

Non-Patent Citations (1)

Also Published As

Similar Documents

Legal Events