CA1058204A - Method for the preparation of carbonic acid monoester salts - Google Patents
Method for the preparation of carbonic acid monoester saltsInfo
- Publication number
- CA1058204A CA1058204A CA241,070A CA241070A CA1058204A CA 1058204 A CA1058204 A CA 1058204A CA 241070 A CA241070 A CA 241070A CA 1058204 A CA1058204 A CA 1058204A
- Authority
- CA
- Canada
- Prior art keywords
- reaction
- preparation
- carbonic acid
- carried out
- salts
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 11
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- -1 carbonic acid monoester salts Chemical class 0.000 title abstract 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 4
- 150000001298 alcohols Chemical class 0.000 claims abstract description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 3
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 238000007710 freezing Methods 0.000 claims description 2
- 230000008014 freezing Effects 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 2
- 150000001340 alkali metals Chemical class 0.000 abstract description 2
- 150000002148 esters Chemical class 0.000 abstract description 2
- 238000007086 side reaction Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 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
- 239000002253 acid Substances 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
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- 125000003118 aryl group Chemical group 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001727 carbonic acid monoesters Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 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
- 239000000203 mixture Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- OWSBHFWSKFIEGF-UHFFFAOYSA-M sodium;methyl carbonate Chemical compound [Na+].COC([O-])=O OWSBHFWSKFIEGF-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
ABSTRACT OF THE DISCLOSURE . -A method is disclosed for the preparation of salts of monoesters of the carbonic acid, the improvement con-sisting 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.
ACID MONOESTER SALTS
ABSTRACT OF THE DISCLOSURE . -A method is disclosed for the preparation of salts of monoesters of the carbonic acid, the improvement con-sisting 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 method for the preparation of salts of monoesters of the carboni~c acid, having the formula:
( RO -~C -~ )n Me o wherein R is a lower alkyl or a lower alkenyl radical, n is 1 or 2, and Me is an alkali metal or an alkaline earth metal, the method comprising the step of reacting the corresponding alcohols with carbon dioxide and a compound of the metal having the formula MemXn wherein X is selected from CO3, SO3, O , OH , BQ3, S , SH , etc. and m is 1, 2 or 3, n having the above indicated values.
The reaction, which takes place accordin~ to the following patternO
MemXn + n CO2 + nROH ~ (ROCOO)nMe + HnXn Mem-l , simply takes place by causing a stream of CO2 to bubble through a solution or a suspension of the selected salt in the alcohol concerned, preferably with stirring. The pressure of CO2 can be varied be-tween o and 100 atmospheres, whereas the temperature is maintained between the freezing and the boiling point temperature of the alcohol, preferably between 0C and ~0 C.
It is also possible to operate in the presence of any solvent whatsoever providing that it is inert to the ends of the subject reaction.
The salts of the carbonic acid monoesters can be isolated by filtration, should they be insoluble, or precipitated with an appropriate solvent, or, lastly, by evaporating of-f the reaction medium.
Such ~alts can be u~ed in lieu of the co~re~ponding alcoholates in the condensation reaction~ for example in the condensatlons of aldehydes with activ~hydrogen-containing molecules~ or of esters with ureas~ or also as the catalysts in the aromatic ~ldehyde disproportionation reaction3.
A~ comparqd with the alcoholates, the ~alt~ as obta~ned ascording to the present invention unfold~ in the above indicated r~action~g a les~ dra~tic action~ the ~ide reactions being limit~d and lower costs being achleYed.
The foregoing considerations will become more clearly apparent from the scrutiny of the followin~ examples~ which are intended tc elucidate the invention without ~ howerer~ limiting the same thereby.
~XAMPLE
-10 grams of a~hydrous K2~03 are ~lurried in 100 mls an~vdrou~ metha~ol and a str~am of C02 f~r an amount slightly over that whlch is absorbed is caused to bubble therethrough with ~igorous stirring at 25C.
The reaction is both e~o~hermic and rapid and is completed within 30 mlns. On completion of the absorption~ the residueg KHC03, is collected on a ~ilter and the solution is evaporated in a Yacuo ~ Th~re are obtained 8.5 grams of impure KOCOOCH
as it contains trace~ of KHC03.
EXAMPL~ ~
__ 5.6 grams o~ CaO are ~lurried in 100 mls allyl alcohal and stirred at 25C und~r a stream vf C02 A reaction which i~
both ex~thermic and rapid is obtained and is completed withir 35 mins. The bulky white precipitate is collected on a filter under a nitro~en blanket, washed with ethyl et~er and dried in a vacuo. There are ~btained 20 grams of Ca(OCOOCH2SH ~ CH2)2.
10 grams of NaOCOOCH3 ~0.1 mol) are dissolved in 100 mls methanol: 16 grams of diethylma~onate and 6 grams urea are added thereto The mixture is refluxed ~uring about & hours~ then is dried in a vacuo to obtain 15 g~ams (approx.) of the sodium salt oP the barbituriç acid. The l~tter~ upon hydrolysis with
( RO -~C -~ )n Me o wherein R is a lower alkyl or a lower alkenyl radical, n is 1 or 2, and Me is an alkali metal or an alkaline earth metal, the method comprising the step of reacting the corresponding alcohols with carbon dioxide and a compound of the metal having the formula MemXn wherein X is selected from CO3, SO3, O , OH , BQ3, S , SH , etc. and m is 1, 2 or 3, n having the above indicated values.
The reaction, which takes place accordin~ to the following patternO
MemXn + n CO2 + nROH ~ (ROCOO)nMe + HnXn Mem-l , simply takes place by causing a stream of CO2 to bubble through a solution or a suspension of the selected salt in the alcohol concerned, preferably with stirring. The pressure of CO2 can be varied be-tween o and 100 atmospheres, whereas the temperature is maintained between the freezing and the boiling point temperature of the alcohol, preferably between 0C and ~0 C.
It is also possible to operate in the presence of any solvent whatsoever providing that it is inert to the ends of the subject reaction.
The salts of the carbonic acid monoesters can be isolated by filtration, should they be insoluble, or precipitated with an appropriate solvent, or, lastly, by evaporating of-f the reaction medium.
Such ~alts can be u~ed in lieu of the co~re~ponding alcoholates in the condensation reaction~ for example in the condensatlons of aldehydes with activ~hydrogen-containing molecules~ or of esters with ureas~ or also as the catalysts in the aromatic ~ldehyde disproportionation reaction3.
A~ comparqd with the alcoholates, the ~alt~ as obta~ned ascording to the present invention unfold~ in the above indicated r~action~g a les~ dra~tic action~ the ~ide reactions being limit~d and lower costs being achleYed.
The foregoing considerations will become more clearly apparent from the scrutiny of the followin~ examples~ which are intended tc elucidate the invention without ~ howerer~ limiting the same thereby.
~XAMPLE
-10 grams of a~hydrous K2~03 are ~lurried in 100 mls an~vdrou~ metha~ol and a str~am of C02 f~r an amount slightly over that whlch is absorbed is caused to bubble therethrough with ~igorous stirring at 25C.
The reaction is both e~o~hermic and rapid and is completed within 30 mlns. On completion of the absorption~ the residueg KHC03, is collected on a ~ilter and the solution is evaporated in a Yacuo ~ Th~re are obtained 8.5 grams of impure KOCOOCH
as it contains trace~ of KHC03.
EXAMPL~ ~
__ 5.6 grams o~ CaO are ~lurried in 100 mls allyl alcohal and stirred at 25C und~r a stream vf C02 A reaction which i~
both ex~thermic and rapid is obtained and is completed withir 35 mins. The bulky white precipitate is collected on a filter under a nitro~en blanket, washed with ethyl et~er and dried in a vacuo. There are ~btained 20 grams of Ca(OCOOCH2SH ~ CH2)2.
10 grams of NaOCOOCH3 ~0.1 mol) are dissolved in 100 mls methanol: 16 grams of diethylma~onate and 6 grams urea are added thereto The mixture is refluxed ~uring about & hours~ then is dried in a vacuo to obtain 15 g~ams (approx.) of the sodium salt oP the barbituriç acid. The l~tter~ upon hydrolysis with
2 N hydrochloric acid and extraction with ether gives 12 gra~s of barbituric acid.
~
12 grams of benzyl cyani~e and 11 grams of benzaldehyde with 10 gFam~ of NaCCOOCH3 are dissolved in 100 mls methanol and refluxed during two hours The sodium carbonate is collectedg hot, on a filter and the solvent is evaporated in a Yacuo. There ~r~ obtained 22 grams of phenrlcinnamonitrile~ having Na2C03 as an impurity The pure produc~ i6 obtained by washing with water.
~
12 grams of benzyl cyani~e and 11 grams of benzaldehyde with 10 gFam~ of NaCCOOCH3 are dissolved in 100 mls methanol and refluxed during two hours The sodium carbonate is collectedg hot, on a filter and the solvent is evaporated in a Yacuo. There ~r~ obtained 22 grams of phenrlcinnamonitrile~ having Na2C03 as an impurity The pure produc~ i6 obtained by washing with water.
Claims (6)
1. A method for the preparation of salts of monoesters of the carbonic acid having the formula:
wherein R is a lower alkyl or a lower alkenyl radical, n is 1 or 2 and Me is an alkali or alkaline earth metal, consisting in reacting the corresponding alcohols with carbon dioxide and with a compound of said metal having the formula MemXn wherein X is selected from CO?, SO?, O= , OH- , BO?, S= , SH- , etc., m is 1, 2 or 3, and n is as defined above.
wherein R is a lower alkyl or a lower alkenyl radical, n is 1 or 2 and Me is an alkali or alkaline earth metal, consisting in reacting the corresponding alcohols with carbon dioxide and with a compound of said metal having the formula MemXn wherein X is selected from CO?, SO?, O= , OH- , BO?, S= , SH- , etc., m is 1, 2 or 3, and n is as defined above.
2. A method according to claim 1, characterized in that the reaction is carried out under a CO2 pressure ranging between 0 and 100 atmospheres.
3. A method according to claim 1, characterized in that the reaction is carried out at a temperature comprised between the freezing point and the boiling point temperature of the employed alcohol.
4. A method according to claim 3, characterized in that the reaction is carried out at a temperature comprised between 0°C and 60°C.
5. A method according to claims 1, 2 or 3, characterized in that the reaction is carried out in the presence of the alcohol only as the reaction medium.
6. A method according to claims 1, 2 or 3, characterized in that the reaction is carried out in the presence of a solvent which is inert for the reaction.
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 (1)
| Publication Number | Publication Date |
|---|---|
| CA1058204A true CA1058204A (en) | 1979-07-10 |
Family
ID=11229564
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA241,070A Expired CA1058204A (en) | 1974-12-10 | 1975-12-04 | Method for the preparation of 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 CA CA241,070A patent/CA1058204A/en not_active Expired
- 1975-12-04 ZA ZA757614A patent/ZA757614B/en unknown
- 1975-12-08 BE BE162534A patent/BE836385A/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 LU LU73950A patent/LU73950A1/xx unknown
- 1975-12-08 CH CH1594275A patent/CH620193A5/en not_active IP Right Cessation
- 1975-12-09 NO NO754159A patent/NO144703C/en unknown
- 1975-12-09 DK DK557375AA patent/DK142749B/en not_active IP Right Cessation
- 1975-12-09 NL NLAANVRAGE7514361,A patent/NL175520C/en not_active IP Right Cessation
- 1975-12-09 SE SE7513876A patent/SE426390B/en unknown
- 1975-12-09 AT AT932875A patent/AT343090B/en not_active IP Right Cessation
- 1975-12-09 ES ES443588A patent/ES443588A1/en not_active Expired
- 1975-12-10 JP JP50146467A patent/JPS593982B2/en not_active Expired
- 1975-12-10 IE IE2690/75A patent/IE42376B1/en unknown
- 1975-12-10 DE DE2555567A patent/DE2555567C3/en not_active Expired
- 1975-12-10 SU SU752196662A patent/SU656503A3/en active
Also Published As
| Publication number | Publication date |
|---|---|
| AT343090B (en) | 1978-05-10 |
| NO754159L (en) | 1976-06-11 |
| DE2555567B2 (en) | 1978-10-12 |
| LU73950A1 (en) | 1976-07-01 |
| IT1026904B (en) | 1978-10-20 |
| NO144703C (en) | 1981-10-21 |
| ATA932875A (en) | 1977-09-15 |
| JPS593982B2 (en) | 1984-01-27 |
| FR2294160B1 (en) | 1980-04-25 |
| DE2555567C3 (en) | 1979-06-07 |
| SE426390B (en) | 1983-01-17 |
| BE836385A (en) | 1976-06-08 |
| NL175520B (en) | 1984-06-18 |
| ES443588A1 (en) | 1977-05-01 |
| CH620193A5 (en) | 1980-11-14 |
| DK557375A (en) | 1976-06-11 |
| IE42376B1 (en) | 1980-07-30 |
| DK142749B (en) | 1981-01-12 |
| DE2555567A1 (en) | 1976-06-16 |
| FR2294160A1 (en) | 1976-07-09 |
| NO144703B (en) | 1981-07-13 |
| ZA757614B (en) | 1976-11-24 |
| NL7514361A (en) | 1976-06-14 |
| NL175520C (en) | 1984-11-16 |
| DK142749C (en) | 1981-08-17 |
| JPS5182214A (en) | 1976-07-19 |
| GB1523477A (en) | 1978-08-31 |
| SE7513876L (en) | 1976-06-11 |
| SU656503A3 (en) | 1979-04-05 |
| IE42376L (en) | 1976-06-10 |
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