GB855883A - ª‡-cyanomethyl-ª‡-methyladipates and preparation thereof - Google Patents
ª‡-cyanomethyl-ª‡-methyladipates and preparation thereofInfo
- Publication number
- GB855883A GB855883A GB18674/57A GB1867457A GB855883A GB 855883 A GB855883 A GB 855883A GB 18674/57 A GB18674/57 A GB 18674/57A GB 1867457 A GB1867457 A GB 1867457A GB 855883 A GB855883 A GB 855883A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- radicals
- anhydrido
- cycloalkyl
- alkyl
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
- C08G18/3821—Carboxylic acids; Esters thereof with monohydroxyl compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/16—Nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Pyrrole Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Polyurethanes Or Polyureas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Compounds suitable as plasticizers, e.g. for polyvinyl chloride, are of formula:, <FORM:0855883/IV(a)/1> where R is an esterifying radical of 1-14 carbon atoms. Specified types of R radical are alkyl, alkenyl, cycloalkyl, alkylcycloalkyl, cycloalkylalkyl, aralkyl and alkoxyalkyl radicals. By hydrolysing and heating, such compounds are converted to an anhydrido-acid, which by reaction with isocyanates yields foams. The compounds or the anhydrido-acid may be converted to triesters, e.g. the tri (2-ethylhexyl) ester, which are plasticizers for polyvinyl chloride. On catalytic reduction, the compounds yield esters of 3-(3-carboxybutyl)-2-pyrrolidinone, which are plasticizers for polyvinyl chloride and polyacrylonitrile-containing plastics.ALSO:The invention comprises compounds of formula: <FORM:0855883/IV(b)/1> where R is a monovalent esterifying group of 1-14 carbon atoms, each R being the same or different, and their preparation by reacting HCN with a compound: <FORM:0855883/IV(b)/2> at a temperature of about 150-340 DEG C. in the presence of an alkaline catalyst which generates cyanide ion from HCN. When R is methyl or ethyl, other R radicals may be introduced by trans-esterification. Specified types of R radicals are alkyl, alkenyl, cycloalkyl, alkylcycloalkyl, cycloalkyl-alkyl, aralkyl and alkoxyalkyl radicals. Suitable alkaline catalysts include alkali metals and their carbonates, and lower alkoxides, oxides, cyanides and peroxides of alkali and alkaline earth metals, tertiary amines and quaternary ammonium bases. The HCN may be used in the gaseous or liquid state. The compounds of the invention are useful as plastizers, synthetic lubricants and fungicides and insecticides. They may be hydrolysed and heated to form an anhydrido-acid; this or the compounds themselves may be converted to triesters, e.g. the tri(2-ethylhexyl) ester. Catalytic hydrogenation of the compounds of the invention gives esters of 3-(3-carboxybutyl)-2-pyrrolidinone.ALSO:Foams are stated to be formed when isocyanates are reacted with the anhydrido-acid obtained from HOOC. <FORM:0855883/V/1>ALSO:Compounds of fungicidal and insecticidal activity, employed e.g. in standard 10% dust formulations, have the formula: <FORM:0855883/VI/1> where R is an esterifying radical of 1-14 carbon atoms. Specified types of R radicals are alkyl, alkenyl, cycloalkyl, alkylcycloalkyl, cycloalkylalkyl, aralkyl and alkoxyalkyl radicals.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59303956A | 1956-06-22 | 1956-06-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB855883A true GB855883A (en) | 1960-12-07 |
Family
ID=24373119
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB18674/57A Expired GB855883A (en) | 1956-06-22 | 1957-06-13 | ª‡-cyanomethyl-ª‡-methyladipates and preparation thereof |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE558571A (en) |
| CH (1) | CH366273A (en) |
| DE (1) | DE1102718B (en) |
| GB (1) | GB855883A (en) |
| NL (1) | NL97995C (en) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2516307A (en) * | 1949-01-06 | 1950-07-25 | Gen Mills Inc | Vinyl resins plasticized with cyano esters |
-
0
- BE BE558571D patent/BE558571A/xx unknown
- NL NL97995D patent/NL97995C/xx active
-
1957
- 1957-06-13 GB GB18674/57A patent/GB855883A/en not_active Expired
- 1957-06-21 CH CH4750557A patent/CH366273A/en unknown
- 1957-06-21 DE DER21370A patent/DE1102718B/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE1102718B (en) | 1961-03-23 |
| BE558571A (en) | |
| CH366273A (en) | 1962-12-31 |
| NL97995C (en) |
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