GB893268A - Metal salts of 2-carboxy-3-metallo-propenes - Google Patents
Metal salts of 2-carboxy-3-metallo-propenesInfo
- Publication number
- GB893268A GB893268A GB40568/59A GB4056859A GB893268A GB 893268 A GB893268 A GB 893268A GB 40568/59 A GB40568/59 A GB 40568/59A GB 4056859 A GB4056859 A GB 4056859A GB 893268 A GB893268 A GB 893268A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carboxy
- metal
- compounds
- metallo
- propene
- 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
- 229910052751 metal Inorganic materials 0.000 title abstract 10
- 239000002184 metal Substances 0.000 title abstract 10
- 150000003839 salts Chemical class 0.000 title abstract 7
- 150000001875 compounds Chemical class 0.000 abstract 5
- -1 cacsium Chemical compound 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 159000000000 sodium salts Chemical class 0.000 abstract 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- HAZRYQYPIHFWKW-UHFFFAOYSA-N C(=O)(O)C(=C)C[Na] Chemical compound C(=O)(O)C(=C)C[Na] HAZRYQYPIHFWKW-UHFFFAOYSA-N 0.000 abstract 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- 150000001408 amides Chemical class 0.000 abstract 2
- 150000002430 hydrocarbons Chemical group 0.000 abstract 2
- 229910052700 potassium Inorganic materials 0.000 abstract 2
- 239000011591 potassium Substances 0.000 abstract 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 abstract 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- 229910052786 argon Inorganic materials 0.000 abstract 1
- 229910052790 beryllium Inorganic materials 0.000 abstract 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 229910052791 calcium Inorganic materials 0.000 abstract 1
- 239000011575 calcium Substances 0.000 abstract 1
- 239000001569 carbon dioxide Substances 0.000 abstract 1
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 238000006735 epoxidation reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical class C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000000524 functional group Chemical group 0.000 abstract 1
- 150000008282 halocarbons Chemical class 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 229910052743 krypton Inorganic materials 0.000 abstract 1
- DNNSSWSSYDEUBZ-UHFFFAOYSA-N krypton atom Chemical compound [Kr] DNNSSWSSYDEUBZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- PKMBLJNMKINMSK-UHFFFAOYSA-N magnesium;azanide Chemical class [NH2-].[NH2-].[Mg+2] PKMBLJNMKINMSK-UHFFFAOYSA-N 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 abstract 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 150000002902 organometallic compounds Chemical class 0.000 abstract 1
- 239000002245 particle Substances 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 abstract 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 229910052701 rubidium Inorganic materials 0.000 abstract 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 abstract 1
- ONQCKWIDZTZEJA-UHFFFAOYSA-N sodium;pentane Chemical compound [Na+].CCCC[CH2-] ONQCKWIDZTZEJA-UHFFFAOYSA-N 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 239000010936 titanium Substances 0.000 abstract 1
- 229910052719 titanium Inorganic materials 0.000 abstract 1
- 238000006478 transmetalation reaction Methods 0.000 abstract 1
- 229910000568 zirconium hydride Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/14—Monocyclic dicarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/15—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction of organic compounds with carbon dioxide, e.g. Kolbe-Schmitt synthesis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/03—Monocarboxylic acids
- C07C57/08—Crotonic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/46—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid
- C07C57/48—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid having unsaturation outside the aromatic rings
-
- 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
-
- 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
-
- 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
- C07F3/02—Magnesium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Enzymes And Modification Thereof (AREA)
Abstract
893,268. Metal salts of 2-carboxy-3-metallopropenes. ETHYL CORPORATION. Nov. 30, 1959 [Dec. 2, 1958], No. 40568/59. Class 2 (3). The invention comprises a metal salt of 2- carboxy-3-metallo-propene. They may be of formula (when both the metal of the salt and the metallo-substituent are monovalent) where each R represents hydrogen or hydrocarbon groups which can be the same or different, R<SP>1</SP> is an alkylene group and M and M<SP>l</SP> are metals which may be the same or different. It is preferred that M and M<SP>1</SP> are alkali or alkaline earth metals. They may be prepared by reacting a metal salt of a 2-carboxy-propene with a metallating agent such as a metal amide, hdyride or in some cases the metal itself and compounds of formula RxM. Lower alkyl derivatives of metal amides may also be used. Compounds specified include sodium, potassium, lithium, calcium and magnesium amides, potassium, aluminium, magnesium, cacsium, beryllium, rubidium, copper, titanium and zirconium hydrides, amyl sodium, disodiooctadiene, dimethyl and diethyl zinc. The reaction may be carried out at a temperature between 160‹C. and 300‹C. The reactants should be of particle size below about 50 microns. An inert atmosphere such as argon, nitrogen or krypton is employed: in some circumstances it is preferred to carry out the reaction under an inert liquid blanket such as a high boiling hydrocarbon oil. Sub-atmospheric pressure may be used to ensure rapid removal of volatile by-products. Many metal salts according to the invention are specified. The compounds of the invention are highly reactive. Carbonation with solid carbon dioxide followed by hydrolysis yields dicarboxylic acid (e.g. the sodium salt of 2-carboxy-3-sodiopropene yields itaconic acid). Alkylation yields longer chain acid salts, and using excess of an organo halide the compounds yield esters of long chain acids. Reaction with compounds of formula RX 2 where X is a functional group reactive with the 3-metallo substituent yields polyester derivatives. Sulphur gives rise to the sodium mercaptide, and epoxidation gives rise to the appropriate metallic hydroxy alkanates. Transmetallation gives rise to organo metallic compounds, e.g. the sodium salt of 2-carboxy-3- sodio propene reacts with a trialkyl tin halide to give the sodium salt of 2-carboxy-3-(trialkyl tin)- propene.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US893268XA | 1958-12-02 | 1958-12-02 | |
| US846819A US3108134A (en) | 1959-10-16 | 1959-10-16 | Metallometallic salt of unsaturated carboxylic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB893268A true GB893268A (en) | 1962-04-04 |
Family
ID=31980818
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB40568/59A Expired GB893268A (en) | 1958-12-02 | 1959-11-30 | Metal salts of 2-carboxy-3-metallo-propenes |
| GB34921/60A Expired GB912559A (en) | 1958-12-02 | 1960-10-12 | Metallic salts |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB34921/60A Expired GB912559A (en) | 1958-12-02 | 1960-10-12 | Metallic salts |
Country Status (3)
| Country | Link |
|---|---|
| DE (2) | DE1155778B (en) |
| FR (2) | FR1243589A (en) |
| GB (2) | GB893268A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1240699A (en) * | 1984-05-14 | 1988-08-16 | Thomas R. Verhoeven | Preparation of dibenzo(b,f)thiepin compounds |
-
1959
- 1959-11-30 GB GB40568/59A patent/GB893268A/en not_active Expired
- 1959-12-01 DE DEE18576A patent/DE1155778B/en active Pending
- 1959-12-02 FR FR811883A patent/FR1243589A/en not_active Expired
-
1960
- 1960-10-12 GB GB34921/60A patent/GB912559A/en not_active Expired
- 1960-10-15 FR FR841315A patent/FR1270929A/en not_active Expired
- 1960-10-17 DE DEE20052A patent/DE1175671B/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR1270929A (en) | 1961-09-01 |
| DE1155778B (en) | 1963-10-17 |
| FR1243589A (en) | 1961-01-16 |
| GB912559A (en) | 1962-12-12 |
| DE1175671B (en) | 1964-08-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1194503A (en) | Basic Sulfurised Salicylates and method for their preparation | |
| ES462702A1 (en) | Zinc alloy for galvanization processes | |
| US3043857A (en) | Preparation of hydrides of the fourth and fifth group elements | |
| HUT66777A (en) | Process for producing catalyst, catalyst system and process for polymerizing alfa-olefins | |
| US3159626A (en) | Triethylene-diamine alane and a process for its preparation | |
| GB893268A (en) | Metal salts of 2-carboxy-3-metallo-propenes | |
| US2815350A (en) | Method of preparing organic dithiophosphoric acid compounds | |
| US3127448A (en) | Method for preparing tertiary amine boranes | |
| GB1303500A (en) | Process for producing sodium,lithium or potassium dihydrocarbon dihydrides of aluminum | |
| US3047358A (en) | Preparation of boron-hydrogen compounds | |
| GB1015227A (en) | Process for making tetramethyl lead | |
| US3112989A (en) | Method for preparing metal compounds | |
| GB1004043A (en) | Improved procedure for preparing organolithium compounds | |
| KR870000285A (en) | Method for preparing 3-amino-4-hydroxybenzoic acid | |
| US3347891A (en) | Process for purifying organo-tin hydrides | |
| US3042723A (en) | Preparation of boron alkyls | |
| GB1496716A (en) | (3beta-hydroxy-2beta-(substituted-1-alkenyl)-5-oxo-1alpha-cyclopentyl)heptanoic acids | |
| US3401189A (en) | Tetramethyl lead manufacture | |
| GB1220851A (en) | METHOD FOR THE PREPARATION OF alpha,alpha-DIALKYL-beta-PROPIOLACTONES | |
| GB574092A (en) | Chemical process for the manufacture of alkaline earth metals and alloys thereof | |
| US2090592A (en) | Process for producing alkali metal | |
| US3547971A (en) | Preparation of dioxaborinane compounds | |
| US2950304A (en) | Preparation of organomercury compounds | |
| US3337637A (en) | Reduction of organo-sulfenyl chlorides to organic disulfides | |
| US2994718A (en) | Method for preparation of alkyldiboranes |