IE42376B1 - Process for producing carbonic acid monoester salts - Google Patents
Process for producing carbonic acid monoester saltsInfo
- Publication number
- IE42376B1 IE42376B1 IE2690/75A IE269075A IE42376B1 IE 42376 B1 IE42376 B1 IE 42376B1 IE 2690/75 A IE2690/75 A IE 2690/75A IE 269075 A IE269075 A IE 269075A IE 42376 B1 IE42376 B1 IE 42376B1
- Authority
- IE
- Ireland
- Prior art keywords
- process according
- carbonic acid
- reaction
- salt
- acid monoester
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 18
- -1 carbonic acid monoester salts Chemical class 0.000 title claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 3
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 150000001727 carbonic acid monoesters Chemical class 0.000 claims description 4
- 150000001339 alkali metal compounds Chemical class 0.000 claims description 2
- 150000001341 alkaline earth metal compounds Chemical class 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 238000007710 freezing Methods 0.000 claims description 2
- 230000008014 freezing Effects 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 abstract description 2
- 238000007086 side reaction Methods 0.000 abstract description 2
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- VFOKYTYWXOYPOX-UHFFFAOYSA-N 2,3-diphenylprop-2-enenitrile Chemical compound C=1C=CC=CC=1C(C#N)=CC1=CC=CC=C1 VFOKYTYWXOYPOX-UHFFFAOYSA-N 0.000 description 1
- 101100168093 Caenorhabditis elegans cogc-2 gene Proteins 0.000 description 1
- 101100011365 Caenorhabditis elegans egl-13 gene Proteins 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- MHQHHBYRYFICDV-UHFFFAOYSA-M sodium;pyrimidin-3-ide-2,4,6-trione Chemical compound [Na+].O=C1CC(=O)[N-]C(=O)N1 MHQHHBYRYFICDV-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/04—Preparation of esters of carbonic or haloformic acids from carbon dioxide or inorganic carbonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/141—Feedstock
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Inorganic Fibers (AREA)
Abstract
METHOD FOR THE PREPARATION OF CARBONIC ACID MONOESTER SALTS . A method is disclosed for the preparation of salts of monoesters of the carbonic acid, the improvement consisting in that the alcohols corresponding to the esters are reacted with carbon dioxide and a compound of an alkali metal or an alkaline earth metal. A distinct advantage over the use of the alcoholates is obtained inasmuch as the reaction is less violent, side-reactions are put aside and the costs are lowered.
Description
This invention relates to a process for producing salts of monoesters of carbonic acid.
According to the invention there is provided a process for producing a salt of a carbonic acid monoester having the formula (RO - C - 0) M
II where M represents an alkali metal or an 'alkaline earth metal, ji is 1 or 2, and R represents an alkyl radical, a cycloalkyl radical, an aryl radical or an aralkyl radical, which method comprised reacting carbon dioxide, an alcohol of formula ROH and an alkali metal compound or alkaline earth metal compound having an anion selected from C03=, S03=, 0=, B03=, S= and SH-, to form the desired carbonic acid monoester salt.
The radical R may be substituted or unsubstituted, mono- or polyhydroxyl ated, and saturated or unsaturated.
The reaction takes place according to the following equation:
„+nC0,+hR0H— (R0C00)nM+HnXnMm-l· where m is 1, 2 or 3. It may be performed simply by causing a stream of COg
- 2 42376 to bubble through a solution or a suspension of the selected metal compound in the alcohol which is used, preferably with stirring. It is also possible to carry out the reaction in the presence of a solvent or diluent providing that it is inert to the reactants and products.
The pressure of CO^ may be varied, for example, from 0 to 100 atmospheres gauge.
The temperature of the reaction is preferably maintained between the freezing point and the boiling point temperature of the alcohol, more preferably from 0°C to 60°C.
The salts of carbonic acid monoesters produced by the process of the invention may be isolated 'from the product mixture by, for example filtration, if they are insoluble. Alternatively they may be precipitated from an appropriate solvent, or evaporated off from the product mixture.
The salts produced by the process of the invention may be used instead of the corresponding alcoholates in condensation reactions, for example in the condensation of aldehydes with active-hydrogen-containing molecules, or of esters with ureas. They may also be used as catalysts in the disproportionation reactions of aromatic aldehydes.
By comparison with alcoholates, the salts produced according to the present invention lead, in the above indicated reactions, to a less drastic reaction, which means that side reactions are limited and thus lower costs are incurred.
The following Examples 1 and 2 illustrate the invention; Examples 3 and 4 illustrate the uses to which the products of the process according to the invention may be put.
- 3 4 2376
EXAMPLE 1.
grants of anhydrous KgCOg were slurried in 100 mis of anhydrous methanol and a stream of COg was bubbled through the slurry with vigorous stirring at 25°C. The amount of COg used was slightly greater than that which was absorbed by the slurry under these conditions.
The reaction was both exothermic and rapid, and was completed within 30 minutes. On completion of the absorption, the residue, that is KHCOg, was collected on a filter and the solution was evaporated in vacuo.
There were obtained 8.5 grams of KOCOOCHgi this product was slightly impure since it contained traces of KHC03<
EXAMPLE 2.
.6 grams of CaO were slurried in 100 mis of allyl alcohol and stirred at 25°C under a stream of COg. There ensued a reaction which was both exothermic and rapid; this reaction was completed within 35 minutes. The bulky white precipitate which was produced was collected on a filter under a nitrogen atmosphere, washed with ethyl ether and dried in vacuo. There were obtained 20 grams of
Ca(OCOOCHgCH=CHg)g.
EXAMPLE 3.
grams of NaOCOOCHg (0.1 mol) were dissolved in 100 mis of methanol;
grams of diethylmalonate and 6 grams urea were added to the resulting solution. The mixture thus formed was refluxed for about 8 hours, and the reflux product was dried in vacuo to yield about 15 grams of sodium barbiturate. This salt, following hydrolysis with 2 N hydrochloric acid and extraction with ether, gave
12 grams of barbituric acid.
EXAMPLE 4.
grams of benzyl cyanide, 11 grams of benzaldehyde and 10 grams of NaOCOOCHg were dissolved in 100 mis of methanol and refluxed for two hours.
The sodium carbonate which formed was filtered from the mixture whilst hot
- 4 42376 and the solvent was evaporated in vacuo. There were obtained 22 grams of phenyl cinnamonitrile, having NagCO^ as an impurity. The pure product was obtained by washing with water.
Claims (8)
1. A process for producing a salt of a carbonic acid monoester having the formula (RO - C - 0) n M where M represents an alkali metal or an alkaline earth metal, jn is 1 or 2, and R represents an alkyl radical, a cyeloalkyl radical, an aryl radical or an aralkyl radical, which method comprises reacting carbon dioxide, an alcohol of formula ROH and an alkali metal compound or alkaline earth metal compound having an anion selected from C0 3 =, S0 3 =, 0=, B0 3 =, S= and SH-, to form the desired carbonic acid monoester salt.
2. A process according to Claim 1 wherein the carbon dioxide is at a pressure of from 0 to 100 atmospheres gauge.
3. A process according to Claim 1 or 2 wherein the reaction is carried out at a temperature which is between the freezing point and the boiling point of the alcohol.
4. A process according to Claim 3 wherein the reaction is carried out at a temperature of from 0 to 60°C.
5. A process according to any one of the preceding claims wherein the reaction is carried out in a diluent which is inert to the reactants and products.
6. A process according to any one of the preceding claims which includes the additional step of isolating the desired salt from the product mixture.
7. A process according to Claim T substantially as described in Example 1 or 2. - 5 42376
8. A salt of a carbonic acid mono ester whenever produced by the process according to any one of the preceding claims.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT30338/74A IT1026904B (en) | 1974-12-10 | 1974-12-10 | PROCEDURE FOR THE PREPARATION OF MONOESTER SALTS OF CARBONIC ACID |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE42376L IE42376L (en) | 1976-06-10 |
| IE42376B1 true IE42376B1 (en) | 1980-07-30 |
Family
ID=11229564
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2690/75A IE42376B1 (en) | 1974-12-10 | 1975-12-10 | Process for producing carbonic acid monoester salts |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS593982B2 (en) |
| AT (1) | AT343090B (en) |
| BE (1) | BE836385A (en) |
| CA (1) | CA1058204A (en) |
| CH (1) | CH620193A5 (en) |
| DE (1) | DE2555567C3 (en) |
| DK (1) | DK142749B (en) |
| ES (1) | ES443588A1 (en) |
| FR (1) | FR2294160A1 (en) |
| GB (1) | GB1523477A (en) |
| IE (1) | IE42376B1 (en) |
| IT (1) | IT1026904B (en) |
| LU (1) | LU73950A1 (en) |
| NL (1) | NL175520C (en) |
| NO (1) | NO144703C (en) |
| SE (1) | SE426390B (en) |
| SU (1) | SU656503A3 (en) |
| ZA (1) | ZA757614B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4123446A (en) * | 1977-04-11 | 1978-10-31 | Allied Chemical Corporation | Synthesis of metal alkyl carbonates |
| US4217298A (en) * | 1977-09-05 | 1980-08-12 | Tokuyama Soda Kabushiki Kaisha | Process for preparing organic carbonates |
| DE2748718A1 (en) * | 1977-10-29 | 1979-05-03 | Bayer Ag | PROCESS FOR THE PRODUCTION OF DIALKYLCARBONATES |
| JPH0251684U (en) * | 1988-10-03 | 1990-04-12 | ||
| FR2669925B1 (en) * | 1990-11-30 | 1993-01-29 | Rhone Poulenc Chimie | PROCESS FOR THE PREPARATION OF POLYALKOXYLATED AROMATIC COMPOUNDS. |
-
1974
- 1974-12-10 IT IT30338/74A patent/IT1026904B/en active
-
1975
- 1975-12-04 ZA ZA757614A patent/ZA757614B/en unknown
- 1975-12-04 CA CA241,070A patent/CA1058204A/en not_active Expired
- 1975-12-08 LU LU73950A patent/LU73950A1/xx unknown
- 1975-12-08 CH CH1594275A patent/CH620193A5/en not_active IP Right Cessation
- 1975-12-08 GB GB50306/75A patent/GB1523477A/en not_active Expired
- 1975-12-08 FR FR7537463A patent/FR2294160A1/en active Granted
- 1975-12-08 BE BE162534A patent/BE836385A/en not_active IP Right Cessation
- 1975-12-09 ES ES443588A patent/ES443588A1/en not_active Expired
- 1975-12-09 SE SE7513876A patent/SE426390B/en unknown
- 1975-12-09 NL NLAANVRAGE7514361,A patent/NL175520C/en not_active IP Right Cessation
- 1975-12-09 DK DK557375AA patent/DK142749B/en not_active IP Right Cessation
- 1975-12-09 NO NO754159A patent/NO144703C/en unknown
- 1975-12-09 AT AT932875A patent/AT343090B/en not_active IP Right Cessation
- 1975-12-10 DE DE2555567A patent/DE2555567C3/en not_active Expired
- 1975-12-10 SU SU752196662A patent/SU656503A3/en active
- 1975-12-10 IE IE2690/75A patent/IE42376B1/en unknown
- 1975-12-10 JP JP50146467A patent/JPS593982B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DK142749B (en) | 1981-01-12 |
| DE2555567B2 (en) | 1978-10-12 |
| IT1026904B (en) | 1978-10-20 |
| ES443588A1 (en) | 1977-05-01 |
| CA1058204A (en) | 1979-07-10 |
| ATA932875A (en) | 1977-09-15 |
| CH620193A5 (en) | 1980-11-14 |
| DK142749C (en) | 1981-08-17 |
| LU73950A1 (en) | 1976-07-01 |
| FR2294160B1 (en) | 1980-04-25 |
| NL7514361A (en) | 1976-06-14 |
| BE836385A (en) | 1976-06-08 |
| FR2294160A1 (en) | 1976-07-09 |
| AT343090B (en) | 1978-05-10 |
| NO754159L (en) | 1976-06-11 |
| DE2555567C3 (en) | 1979-06-07 |
| JPS5182214A (en) | 1976-07-19 |
| IE42376L (en) | 1976-06-10 |
| NL175520B (en) | 1984-06-18 |
| ZA757614B (en) | 1976-11-24 |
| GB1523477A (en) | 1978-08-31 |
| JPS593982B2 (en) | 1984-01-27 |
| DE2555567A1 (en) | 1976-06-16 |
| NL175520C (en) | 1984-11-16 |
| NO144703C (en) | 1981-10-21 |
| NO144703B (en) | 1981-07-13 |
| SU656503A3 (en) | 1979-04-05 |
| SE426390B (en) | 1983-01-17 |
| SE7513876L (en) | 1976-06-11 |
| DK557375A (en) | 1976-06-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5026676A (en) | Catalyst for the copolymerization of epoxides with CO2 | |
| EP0581131B1 (en) | A process for producing alkylene carbonates | |
| US4482738A (en) | Process for preparing semicarbazide hydrochloride | |
| EP0201957A2 (en) | Process for the preparation of a carboxylic acid salt | |
| US2784201A (en) | Process of making alkylene carbonates | |
| US3349100A (en) | Production of alkylene mono-thiolcarbonate and alkylene sulfide | |
| IE42376B1 (en) | Process for producing carbonic acid monoester salts | |
| EP0347045B1 (en) | Process for producing cyanamide from calcium cyanamide | |
| US4116997A (en) | Method for the preparation of carbonic acid monoester salts | |
| IE42792B1 (en) | Production of alkylene glycols | |
| CA1252113A (en) | Method for producing an ammonia complex of zinc- dithiocarbamate | |
| US3956405A (en) | Process for manufacturing polyfluoroalkyl propanols | |
| JPS6259104B2 (en) | ||
| US3972943A (en) | Process for preparing alkaliacetylacetonates | |
| US3886209A (en) | Process for preparing alpha, omega-diaminocarboxylic acids | |
| JPS6312865B2 (en) | ||
| US1584907A (en) | Production of esters from amide acid sulphates | |
| CN1041728C (en) | Synthsis of doxofylline | |
| US4083873A (en) | Novel bisulfate and sulfate salts of bis(2-aminoethyl) ether and methods of preparation | |
| US4946995A (en) | Process for the production of thiocarbohydrazide | |
| US3609163A (en) | Process for preparing 5- vinyl-1,3,4-dioxcazol-2-ones | |
| EP0699190B1 (en) | Preparation of 3-mercapto-5-amino-1h-1,2,4-triazole | |
| GB2024224A (en) | Production of peroxydicarbonates | |
| JPS5858339B2 (en) | Production method of alkali metal salt of carbonic acid monoester | |
| JPH09143169A (en) | Production of 4,6-diamino-1,3,5-triazin-2-yl-benzoic acids |