SU580827A3 - Способ получени с-с-диалкиловых эфиров малоновой кислоты - Google Patents
Способ получени с-с-диалкиловых эфиров малоновой кислотыInfo
- Publication number
- SU580827A3 SU580827A3 SU7402078987A SU2078987A SU580827A3 SU 580827 A3 SU580827 A3 SU 580827A3 SU 7402078987 A SU7402078987 A SU 7402078987A SU 2078987 A SU2078987 A SU 2078987A SU 580827 A3 SU580827 A3 SU 580827A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- ester
- malonic acid
- acid
- reaction
- carried out
- Prior art date
Links
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 14
- 150000002148 esters Chemical class 0.000 title claims description 4
- 239000003054 catalyst Substances 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 3
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- UMYVESYOFCWRIW-UHFFFAOYSA-N cobalt;methanone Chemical compound O=C=[Co] UMYVESYOFCWRIW-UHFFFAOYSA-N 0.000 claims 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 11
- QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- -1 bromoacetic acid ester Chemical class 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 5
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 239000000292 calcium oxide Substances 0.000 description 3
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 3
- RVBUZBPJAGZHSQ-UHFFFAOYSA-N 2-chlorobutanoic acid Chemical compound CCC(Cl)C(O)=O RVBUZBPJAGZHSQ-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- 239000004808 2-ethylhexylester Substances 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- MQIKJSYMMJWAMP-UHFFFAOYSA-N dicobalt octacarbonyl Chemical group [Co+2].[Co+2].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] MQIKJSYMMJWAMP-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QZBQQHUYQKGPLQ-UHFFFAOYSA-N 2-ethylhexyl 2-chloroacetate Chemical compound CCCCC(CC)COC(=O)CCl QZBQQHUYQKGPLQ-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- HGINADPHJQTSKN-UHFFFAOYSA-N Monoethyl malonic acid Chemical compound CCOC(=O)CC(O)=O HGINADPHJQTSKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical group 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- IYPQZXRHDNGZEB-UHFFFAOYSA-N cobalt sodium Chemical compound [Na].[Co] IYPQZXRHDNGZEB-UHFFFAOYSA-N 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- GICBTEWABQGGPR-UHFFFAOYSA-N methoxymethane;propanedioic acid Chemical compound COC.OC(=O)CC(O)=O GICBTEWABQGGPR-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
- C07C69/38—Malonic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732359963 DE2359963C2 (de) | 1973-12-01 | 1973-12-01 | Verfahren zur Herstellung von Malonsäuredialkylestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU580827A3 true SU580827A3 (ru) | 1977-11-15 |
Family
ID=5899624
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU7402078987A SU580827A3 (ru) | 1973-12-01 | 1974-11-29 | Способ получени с-с-диалкиловых эфиров малоновой кислоты |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS5324049B2 (nl) |
| BE (1) | BE822546A (nl) |
| CH (1) | CH605575A5 (nl) |
| DD (1) | DD115350A5 (nl) |
| DE (1) | DE2359963C2 (nl) |
| DK (1) | DK134779C (nl) |
| ES (1) | ES432479A1 (nl) |
| FI (1) | FI61683C (nl) |
| FR (1) | FR2253006B1 (nl) |
| GB (1) | GB1448646A (nl) |
| IT (1) | IT1023464B (nl) |
| NL (1) | NL185839C (nl) |
| SU (1) | SU580827A3 (nl) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2603026C2 (de) * | 1976-01-28 | 1986-06-19 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur Herstellung von Malonsäuredialkylester |
| SU614742A3 (ru) * | 1975-06-02 | 1978-07-05 | Динамит Нобель Аг (Фирма) | Способ получени с - с диалкиловых эфиров малоновой кислоты |
| IT1075123B (it) * | 1977-02-24 | 1985-04-22 | Snam Progetti | Processo per la preparazione di derivati dell'acido malonico |
| JPS54128512A (en) * | 1978-03-29 | 1979-10-05 | Denki Kagaku Kogyo Kk | Preparation of malonic acid dialkyl ester |
| JPS5921851B2 (ja) * | 1978-08-17 | 1984-05-22 | 電気化学工業株式会社 | アルキルカルボン酸エステルの製法 |
| FR2631623B1 (fr) * | 1988-05-19 | 1990-10-19 | Rhone Poulenc Chimie | Procede de preparation de malonates d'alkyle |
| IL133909A0 (en) | 1999-01-11 | 2001-04-30 | Lonza Ag | Process for preparing malonic esters |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2542767A (en) * | 1949-02-11 | 1951-02-20 | Du Pont | Organic ester synthesis |
| NL272335A (nl) * | 1960-12-08 |
-
1973
- 1973-12-01 DE DE19732359963 patent/DE2359963C2/de not_active Expired
-
1974
- 1974-11-25 BE BE150808A patent/BE822546A/xx not_active IP Right Cessation
- 1974-11-28 FI FI345174A patent/FI61683C/fi active
- 1974-11-28 FR FR7439089A patent/FR2253006B1/fr not_active Expired
- 1974-11-29 IT IT5431174A patent/IT1023464B/it active
- 1974-11-29 GB GB5189474A patent/GB1448646A/en not_active Expired
- 1974-11-29 SU SU7402078987A patent/SU580827A3/ru active
- 1974-11-29 NL NL7415608A patent/NL185839C/nl not_active IP Right Cessation
- 1974-11-29 DD DD18267374A patent/DD115350A5/xx unknown
- 1974-11-29 DK DK622774A patent/DK134779C/da active
- 1974-11-29 CH CH1591374A patent/CH605575A5/xx not_active IP Right Cessation
- 1974-11-30 ES ES432479A patent/ES432479A1/es not_active Expired
- 1974-12-02 JP JP13827974A patent/JPS5324049B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7415608A (nl) | 1975-06-03 |
| DK622774A (nl) | 1975-08-11 |
| DK134779C (da) | 1977-06-06 |
| DD115350A5 (nl) | 1975-09-20 |
| GB1448646A (en) | 1976-09-08 |
| NL185839C (nl) | 1990-08-01 |
| FR2253006A1 (nl) | 1975-06-27 |
| NL185839B (nl) | 1990-03-01 |
| ES432479A1 (es) | 1976-11-16 |
| DE2359963C2 (de) | 1982-01-28 |
| FI345174A (nl) | 1975-06-02 |
| FI61683C (fi) | 1982-09-10 |
| DE2359963A1 (de) | 1975-06-05 |
| JPS5324049B2 (nl) | 1978-07-18 |
| FR2253006B1 (nl) | 1978-12-08 |
| BE822546A (fr) | 1975-03-14 |
| JPS50111015A (nl) | 1975-09-01 |
| CH605575A5 (nl) | 1978-09-29 |
| DK134779B (da) | 1977-01-17 |
| FI61683B (fi) | 1982-05-31 |
| IT1023464B (it) | 1978-05-10 |
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