WO2021070193A1 - A method for removal of water from organic solvents - Google Patents

A method for removal of water from organic solvents Download PDF

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Publication number
WO2021070193A1
WO2021070193A1 PCT/IN2020/050781 IN2020050781W WO2021070193A1 WO 2021070193 A1 WO2021070193 A1 WO 2021070193A1 IN 2020050781 W IN2020050781 W IN 2020050781W WO 2021070193 A1 WO2021070193 A1 WO 2021070193A1
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Prior art keywords
water
organic solvents
metal carbonate
gas
removal
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PCT/IN2020/050781
Other languages
French (fr)
Inventor
Joy VADAKKAN THOMAS
Gopika K.N.
Jessiya JOY
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Vadakkan Thomas Joy
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Publication of WO2021070193A1 publication Critical patent/WO2021070193A1/en

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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G33/00—Dewatering or demulsification of hydrocarbon oils
    • C10G33/06—Dewatering or demulsification of hydrocarbon oils with mechanical means, e.g. by filtration
    • 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
    • C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
    • C07C29/88—Separation; Purification; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification of at least one compound
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/85—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to a chemical modification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
    • C07C7/14833—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with metals or their inorganic compounds
    • C07C7/1485—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with metals or their inorganic compounds oxides; hydroxides; salts
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B1/00—Production of fats or fatty oils from raw materials
    • C11B1/10—Production of fats or fatty oils from raw materials by extracting

Definitions

  • the present invention relates to a method for removal of water from organic solvents . More particularly, it relates to a very simple and green method for removal of water from organic solvents, particularly alcoholic solvents.
  • Anhydrous organic solvents are typically required for many laboratory processes and also for various other uses for e.g. anhydrous ethanol is widely used in chemical industry for the synthesis of esters, perfumes, detergents, paints, cosmetics, medicines, etc.
  • a very important use of anhydrous ethanol is as a gasoline additive.
  • Organic solvents are normally dried by vacuum drying in the presence of dehydrating agents or by direct treatment with dehydrating agents or by azeotropic distillation with the aid of an entraining agent.
  • compounds like CaSO 4 , Na 2 SO 4 , MgSO 4 , etc. remove water by forming hydrates.
  • drying agents such as CaO, CaH 2 , LiA1H 4 , P 4 O 10 , etc. remove water by chemically reacting with it. These methods produce lot of chemical waste and are not suitable for drying solvents in an industrial scale.
  • US4273621 discloses a process for dehydrating ethanol and for the production of gasohol therefrom.
  • the process involves utilizing a high-pressure distillation (with a single distillation column) of an aqueous ethanol admixture (preferably one derived from a conventional ethanol fermentation process), to achieve a vapor phase ethanol-water admixture containing about 90 percent, by weight, of ethanol, and then drying the vaporous admixture, in the presence of CO 2 , with a crystalline zeolite type 3 ⁇ .
  • a high-pressure distillation with a single distillation column
  • an aqueous ethanol admixture preferably one derived from a conventional ethanol fermentation process
  • Yet another process as disclosed in US4400241 includes the use of a hydrated aliphatic, monohydric alcohol to produce a fuel grade alcohol.
  • a select group of alkali-metal and alkaline- earth metal salts are added to and dissolved within a low volatility polyhydric alcohol to form a solution, or solvent extractant, and said solvent extractant is contacted and dissolved within said aliphatic, monohydric hydrated alcohol, the solvent extractant distilled, condensed, and a dehydrated fuel grade aliphatic monohydric fuel grade alcohol recovered.
  • the process is a very complicated procedure and regeneration of above substances by removing water is an additional tedious process.
  • the present invention provides a process for removal of water from organic solvent comprising the step of contacting the organic solvent with at least one anhydrous solid metal carbonate and dry CO 2 gas.
  • the present invention provides a process for removal of water from organic solvents.
  • the process is relatively fast and involves the use of inexpensive, non-toxic and readily available raw materials.
  • the present invention relates to a process for removal of water from organic solvent comprising the steps of contacting the organic solvent with at least one anhydrous solid metal carbonate and dry CO 2 gas at a predetermined reaction temperature.
  • CO 2 gas is in the range of 1:1-2 molar equivalents.
  • the predetermined temperature is in the range of -50 °C to 100 °C is preferred.
  • metal carbonate and the reaction temperature are chosen such that metal bicarbonate(s) formed is/are stable at the reaction temperature chosen:
  • metal carbonate chosen is selected from, but not limited to, Na 2 CO 3 , K 2 CO 3 ,
  • Rb 2 CO 3 and/or CS2CO 3 like carbonates of alkaline earth metals (MCO 3 , where M is an alkaline earth metal cation).
  • MCO 3 alkaline earth metals
  • the metal carbonate chosen is selected from, but not limited to, MgCO 3 ,
  • the solid bicarbonates (M(HCO 3 ) 2 ) of above alkaline earth metals are unstable at ordinary temperatures and hence in such cases a low reaction temperature selected from the range -50 °C to 10 °C is preferred.
  • the water combines with M 2 CO 3 and CO 2 to form solid MHCO 3 , according to the following reaction.
  • M 2 CO 3 /MCO 3 dissolved in organic solvent is not desirable and is to be removed, a simple distillation may be performed to get dry pure organic solvent. If the organic solvent has a high boiling point and if at that temperature appreciable thermal decomposition of MHCO 3 can occur, then a vacuum distillation at lower temperature is preferred. The M 2 CO 3 and CO 2 gas can be regenerated by the thermal decomposition of MHCO 3 .
  • the water formed in the reaction can be removed by passing the gas through a drying column or through a cold trap to get dry CO 2 gas.
  • drying organic solvents by the method of this invention does not produce any chemical waste.
  • the present invention provides “green” method for the removal of water from organic solvents.
  • the method can be applied to dry any organic solvent which is not acidic enough to react with M 2 CO 3 or MHCO 3 or MCO 3 and M(HC03) 2 , according to the type of metal carbonate chosen.
  • the organic solvent is selected from, but not limited to, alcohols, ketones, aldehydes, ethers, aliphatic and aromatic nitriles, aliphatic hydrocarbons like hexane, aromatic hydrocarbons like benzene, toluene. Since the solubilities of both M 2 CO 3 and MHCO 3 or MCO 3 and M(HCO 3 ) 2 in most organic solvents are very low, this reaction can be used for the efficient removal of water from such organic solvents.
  • the organic solvent to be dried is taken in a vessel fitted with an outlet tube and inlet tube.
  • Required amount of M 2 CO 3 or MCO 3 is then added to the solvent in the vessel.
  • a stream of dry CO 2 gas is passed through the inlet tube to the solvent containing water and M 2 CO 3 or MCO 3 under constant stirring.
  • the outlet tube is kept under dry oil to prevent the entry of moisture to the reaction vessel.
  • the temperature is selected in such a way that the rate of the reaction is maximum with the metal carbonate, carbon dioxide gas and the organic solvent chosen and at the same time appreciable thermal decomposition of MHCO 3 or
  • M(HCO 3 ) 2 does not occur at that temperature.
  • the temperature is preferably below 50°C.
  • the density of the solvent is checked at predetermined time intervals. When desired amount of water has been removed, as evident from density values, the reaction is stopped. The unreacted M 2 CO 3 and MHCO 3 or MCO 3 and M(HCO 3 ) 2 formed in the reaction is then removed from the dried solvent by filtration.
  • the organic solvent obtained has a moisture content less than 0.8%.
  • the water formed in the reaction can be removed by passing the gas through a drying column or through a cold trap to get dry CO 2 gas.
  • the process of the present invention is clean and environmentally friendly.
  • the drying of the organic solvents by the method of this invention does not produce any chemical waste.
  • the raw materials used such as the alkali metal carbonates like sodium carbonate or potassium carbonate are cheap and environmentally friendly.
  • the present invention provides “green” method for the removal of water from organic solvents. Moreover, it is a rapid process where the reaction proceeds at faster rate and results in almost quantitative dehydration with well optimized parameters.
  • the whole reaction was conducted at room temperature (—30 °C).
  • the outlet tube was kept under oil to prevent entry of moisture to the reaction vessel.
  • Density of the ethanol was checked at specific time intervals and sufficient amount of water was found to be removed, as shown by the density values, the reaction was stopped by stopping the flow of CO 2 gas. Both Na 2 CO 3 left unreacted and NaHCO 3 formed in the reaction were removed by simple filtration under dry atmosphere.
  • Example 2 About 60ml of acetone solution containing lg of water was taken in a flask fitted with an inlet tube and outlet tube. Then about 8 anhydrous Na 2 CO 3 was added to the flask and a stream of dry CO 2 gas was passed at room temperature, as described above. When the desired density values were obtained the reaction was stopped and Na 2 CO 3 unreacted and NaHCO 3 formed as a result of reaction was the reaction were removed by simple filtration under dry atmosphere.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Mechanical Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Analytical Chemistry (AREA)
  • Water Supply & Treatment (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A method for removal of water from organic solvents This invention discloses an environmentally friendly method for removing water from organic solvents. The process comprises the steps of contacting the organic solvent with at least one anhydrous solid metal carbonate and dry CO2 gas at a predetermined temperature.

Description

TITLE OF THE INVENTION
A method for removal of water from organic solvents
FIELD OF THE INVENTION
[001 ] The present invention relates to a method for removal of water from organic solvents . More particularly, it relates to a very simple and green method for removal of water from organic solvents, particularly alcoholic solvents.
BACKGROUND OF THE INVENTION
[002] Anhydrous organic solvents are typically required for many laboratory processes and also for various other uses for e.g. anhydrous ethanol is widely used in chemical industry for the synthesis of esters, perfumes, detergents, paints, cosmetics, medicines, etc. A very important use of anhydrous ethanol is as a gasoline additive.
[003] Organic solvents are normally dried by vacuum drying in the presence of dehydrating agents or by direct treatment with dehydrating agents or by azeotropic distillation with the aid of an entraining agent. In one method, compounds like CaSO4, Na2SO4, MgSO4, etc. remove water by forming hydrates. In another method, drying agents such as CaO, CaH2, LiA1H4, P4O10, etc. remove water by chemically reacting with it. These methods produce lot of chemical waste and are not suitable for drying solvents in an industrial scale.
[004] The four main methods used in industries for drying organic solvents are azeotropic distillation, extractive distillation, adsorption with molecular sieves or pervaporation. All these drying methods have many limitations such as high cost, use of expensive or hazardous substances, production of chemical waste or high energy requirement, etc. [005] For extremely high degrees of dryness for non-protic solvents like ethers, additional relatively costly procedures, such as, for example, drying with metallic sodium, lithium aluminum hydride or Grignard compounds, are required. Aside from the fact that such drying procedures as such are too costly and often cannot be carried out on a large commercial scale because of the danger involved in handling the drying materials. All these methods have many limitations such as production of chemical waste, use of expensive or hazardous substances, etc.
[006] US4273621 discloses a process for dehydrating ethanol and for the production of gasohol therefrom. The process involves utilizing a high-pressure distillation (with a single distillation column) of an aqueous ethanol admixture (preferably one derived from a conventional ethanol fermentation process), to achieve a vapor phase ethanol-water admixture containing about 90 percent, by weight, of ethanol, and then drying the vaporous admixture, in the presence of CO2, with a crystalline zeolite type 3 Å. Thus, the process involves extremely tedious process of drying in vapour phase with the use of a crystalline zeolite type 3 Å in the presence of CO2 and requires complicated distillation apparatus.
[007] Yet another process as disclosed in US4400241 includes the use of a hydrated aliphatic, monohydric alcohol to produce a fuel grade alcohol. A select group of alkali-metal and alkaline- earth metal salts are added to and dissolved within a low volatility polyhydric alcohol to form a solution, or solvent extractant, and said solvent extractant is contacted and dissolved within said aliphatic, monohydric hydrated alcohol, the solvent extractant distilled, condensed, and a dehydrated fuel grade aliphatic monohydric fuel grade alcohol recovered. However, the process is a very complicated procedure and regeneration of above substances by removing water is an additional tedious process. [008] Accordingly, there is a substantial need to overcome the disadvantages associated with the known processes for removal of water from organic solvents and for a simple, cheap and green process for the same.
SUMMARY OF THE INVENTION
[009] The present invention provides a process for removal of water from organic solvent comprising the step of contacting the organic solvent with at least one anhydrous solid metal carbonate and dry CO2 gas.
DESCRIPTION OF THE INVENTION
[010] The present invention provides a process for removal of water from organic solvents. The process is relatively fast and involves the use of inexpensive, non-toxic and readily available raw materials.
[011] The present invention relates to a process for removal of water from organic solvent comprising the steps of contacting the organic solvent with at least one anhydrous solid metal carbonate and dry CO2 gas at a predetermined reaction temperature.
[012] In an embodiment of the invention, the ratio of anhydrous solid metal carbonate and dry
CO2 gas is in the range of 1:1-2 molar equivalents.
[013] The predetermined temperature is in the range of -50 °C to 100 °C is preferred.
[014] The metal carbonate and the reaction temperature are chosen such that metal bicarbonate(s) formed is/are stable at the reaction temperature chosen:
(i) like carbonates of alkali metals (M2CO3, where M is an alkali metal cation). The metal carbonate chosen is selected from, but not limited to, Na2CO3, K2CO3,
Rb2CO3 and/or CS2CO3. (ii) like carbonates of alkaline earth metals (MCO3, where M is an alkaline earth metal cation). The metal carbonate chosen is selected from, but not limited to, MgCO3,
CaCO3, SrC03 and/or BaCO3. The solid bicarbonates (M(HCO3)2) of above alkaline earth metals are unstable at ordinary temperatures and hence in such cases a low reaction temperature selected from the range -50 °C to 10 °C is preferred.
In the case of alkali metal salts, the water combines with M2CO3 and CO2 to form solid MHCO3, according to the following reaction.
M2CO3 + H2O + CO2 → 2MHCO3
In the case of alkaline metal salts, the water combines with MCO3 and CO2 to form solid
M(HCO3)2, according to the following reaction.
MCO3 + H2O + CO2 → M(HCO3)2
When the desired amount of water has been removed from the solvent as MHCO3/ M(HCO3)2, the unreacted M2CO3/MCO3 and the MHCO3/M(HCO3)2 formed in the reaction is removed by simple filtration. The solubility of MHCO3/ M(HCO3)2 and M2CO3/MCO3 in the organic solvent to be dried should be preferably very low. If even small amounts of MHCO3/ M(HCO3)2 or
M2CO3/MCO3 dissolved in organic solvent is not desirable and is to be removed, a simple distillation may be performed to get dry pure organic solvent. If the organic solvent has a high boiling point and if at that temperature appreciable thermal decomposition of MHCO3 can occur, then a vacuum distillation at lower temperature is preferred. The M2CO3 and CO2 gas can be regenerated by the thermal decomposition of MHCO3.
2MHCO3 M2CO3 + H2O + CO2
The water formed in the reaction can be removed by passing the gas through a drying column or through a cold trap to get dry CO2 gas. Thus, drying organic solvents by the method of this invention does not produce any chemical waste. Thus, the present invention provides “green” method for the removal of water from organic solvents.
[015] The method can be applied to dry any organic solvent which is not acidic enough to react with M2CO3 or MHCO3 or MCO3 and M(HC03)2, according to the type of metal carbonate chosen.
The organic solvent is selected from, but not limited to, alcohols, ketones, aldehydes, ethers, aliphatic and aromatic nitriles, aliphatic hydrocarbons like hexane, aromatic hydrocarbons like benzene, toluene. Since the solubilities of both M2CO3 and MHCO3 or MCO3 and M(HCO3)2 in most organic solvents are very low, this reaction can be used for the efficient removal of water from such organic solvents.
[016] In a preferred drying process of this invention, the organic solvent to be dried is taken in a vessel fitted with an outlet tube and inlet tube. Required amount of M2CO3 or MCO3 is then added to the solvent in the vessel. A stream of dry CO2 gas is passed through the inlet tube to the solvent containing water and M2CO3 or MCO3 under constant stirring. The outlet tube is kept under dry oil to prevent the entry of moisture to the reaction vessel. The temperature is selected in such a way that the rate of the reaction is maximum with the metal carbonate, carbon dioxide gas and the organic solvent chosen and at the same time appreciable thermal decomposition of MHCO3 or
M(HCO3)2 does not occur at that temperature. The temperature is preferably below 50°C. The density of the solvent is checked at predetermined time intervals. When desired amount of water has been removed, as evident from density values, the reaction is stopped. The unreacted M2CO3 and MHCO3 or MCO3 and M(HCO3)2 formed in the reaction is then removed from the dried solvent by filtration. The organic solvent obtained has a moisture content less than 0.8%.
[017] The M2CO3/MCO3 and CO2 gas can be regenerated by the thermal decomposition of
MHC03/M(HCO3)2.
2MHCO3 M2CO3 + H2O + CO2
M(HCO3)2 → MCO3 + H2O + CO2 [018] The water formed in the reaction can be removed by passing the gas through a drying column or through a cold trap to get dry CO2 gas. Advantageously, the process of the present invention is clean and environmentally friendly. The drying of the organic solvents by the method of this invention does not produce any chemical waste. The raw materials used such as the alkali metal carbonates like sodium carbonate or potassium carbonate are cheap and environmentally friendly. Thus, the present invention provides “green” method for the removal of water from organic solvents. Moreover, it is a rapid process where the reaction proceeds at faster rate and results in almost quantitative dehydration with well optimized parameters.
EXAMPLES
The following experimental examples are illustrative of the invention but not limitative of the scope thereof:
Example 1
About 60ml of ethanol solution containing 2g of water was taken in a flask fitted with an inlet tube and outlet tube. Then about 15g anhydrous Na2CO3 was added to the flask and a stream of dry
CO2 gas was passed through the ethanol solution under constant stirring using magnetic stirrer.
The whole reaction was conducted at room temperature (—30 °C). The outlet tube was kept under oil to prevent entry of moisture to the reaction vessel. Density of the ethanol was checked at specific time intervals and sufficient amount of water was found to be removed, as shown by the density values, the reaction was stopped by stopping the flow of CO2 gas. Both Na2CO3 left unreacted and NaHCO3 formed in the reaction were removed by simple filtration under dry atmosphere.
Example 2 About 60ml of acetone solution containing lg of water was taken in a flask fitted with an inlet tube and outlet tube. Then about 8 anhydrous Na2CO3 was added to the flask and a stream of dry CO2 gas was passed at room temperature, as described above. When the desired density values were obtained the reaction was stopped and Na2CO3 unreacted and NaHCO3 formed as a result of reaction was the reaction were removed by simple filtration under dry atmosphere.
[019] The foregoing description of the invention has been set merely to illustrate the invention and is not intended to be limiting. Since the modifications of the disclosed embodiments incorporating the spirit and substance of the invention may occur to the person skilled in the art, the invention should be construed to include everything within the scope of the disclosure.

Claims

Claims:
1. A process for removal of water from organic solvents comprising the steps of contacting the organic solvent with at least one anhydrous solid metal carbonate and dry CO2 gas at a predetermined temperature.
2. The process as claimed in claim 1, wherein the ratio of the anhydrous solid metal carbonate and dry CO2 gas is in the range of 1:1-2 molar equivalents.
3. The process as claimed in claim 1, wherein the predetermined temperature in the range of -50
°C to l00 °C.
4. The process as claimed in claim 1, wherein the organic solvents are selected from alcohols, ketones, aldehydes, ethers, aliphatic and aromatic nitriles, aliphatic hydrocarbons like hexane, aromatic hydrocarbons like benzene, toluene.
5. The process as claimed in claim 1, wherein the at least one metal carbonate is selected from the carbonates of alkali metals and alkaline earth metals.
6. The process as claimed in claim 4, wherein alkali and alkaline earth metal carbonate is selected from Na2CO3, K2CO3, Rb2CO3, Cs2CO3.MgCO3, CaCO3, S1CO3, BaCO3 or a combination of two or more of these substances.
7. The process as claimed in claim 1, wherein the organic solvent obtained after the drying process has a moisture content less than 0.8%.
8. The process as claimed in claim 1, wherein the process further comprises simple filtration to remove metal bicarbonate by-product and unreacted metal carbonate formed.
PCT/IN2020/050781 2019-10-10 2020-09-09 A method for removal of water from organic solvents WO2021070193A1 (en)

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IN201941040876 2019-10-10

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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4769112A (en) * 1986-01-17 1988-09-06 United Distillers P.L.C. Method for removing water from ethanol

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4769112A (en) * 1986-01-17 1988-09-06 United Distillers P.L.C. Method for removing water from ethanol

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CAI YUANHAO, WANG WEILIN, LI LIANG, WANG ZHAOFENG, WANG SUYING, DING HAO, ZHANG ZHENGGUO, SUN LUYI, WANG WEIXING: "Effective capture of carbon dioxide using hydrated sodium carbonate powders.", MATERIALS, vol. 11, no. 2, 24 January 2018 (2018-01-24), pages 183, XP055816626, Retrieved from the Internet <URL:www.mdpi.com/journal/materials> DOI: 10.3390/ma11020183. *
KUMAR, SANTOSH, NEETU SINGH, AND RAM PRASAD ET AL.: "Anhydrous ethanol: A renewable source of energy", RENEWABLE AND SUSTAINABLE ENERGY REVIEWS, vol. 14, no. 7, 2010, pages 1830 - 1844, XP027068782, DOI: 10.1016/j.rser. 2010.03.01 5 *

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