GB815232A - Bifunctional products from oxo reaction - Google Patents
Bifunctional products from oxo reactionInfo
- Publication number
- GB815232A GB815232A GB34355/55A GB3435555A GB815232A GB 815232 A GB815232 A GB 815232A GB 34355/55 A GB34355/55 A GB 34355/55A GB 3435555 A GB3435555 A GB 3435555A GB 815232 A GB815232 A GB 815232A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ester
- acid
- aldehyde
- dicyclopentadiene
- hydroxy
- 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
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/293—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/60—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members
- C07C2603/66—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members containing five-membered rings
- C07C2603/68—Dicyclopentadienes; Hydrogenated dicyclopentadienes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Polyvinyl chloride resin compositions are plasticized with a compound of the formula: <FORM:0815232/IV (a)/1> in which both hydrogen atoms on one of the carbon atoms marked with an asterisk are replaced by two <FORM:0815232/IV (a)/2> groups, in which R and R11 represent n-butyl radicals (see Group IV (b)).ALSO:The invention comprises compounds having the formula <FORM:0815232/IV (b)/1> in which both hydrogen atoms on one of the carbon atoms marked with an asterisk are replaced by two <FORM:0815232/IV (b)/2> groups, R and R11 being alkyl radicals; a process for the production of a dimethylol derivative of an ester aldehyde that comprises reacting a cyclic diolefin with an aliphatic monocarboxylic or dicarboxylic acid to form an olefinic ester and treating the ester with carbon monoxide and hydrogen, in the presence of a cobalt carbonylation catalyst and at a temperature within the range 225-375 DEG F. and a pressure within the range 1500 to 4500 p.s.i.g. to obtain an ester aldehyde and reacting the ester aldehyde with formaldehyde to produce the corresponding dimethylol derivative and a process for converting the dimethylol derivative to a triester by reaction with a monocarboxylic acid. Cyclic diolefins mentioned include cyclopentadiene, dicyclopentadiene, their homologues, vinyl cyclohexene, dipentene, limonene, terpinolene, terpinene and sylvestrene. Carboxylic acids specified for reaction with the diolefin include formic, acetic, propionic, capric, palmitic, isooctanoic, isodecanoic, isotridecanoic, adipic and sebacic acids. The reaction between the acid and diolefin is preferably catalysed by condensation catalysts such as sulphuric and perchloric acids, boron trifluoride and the boron trifluoride - phosphoric acid complex. Carbonylation catalysts mentioned include the naphthenate, stearate, oleate, acetate and oxide of cobalt. An apparatus for carrying out the process is described with reference to a drawing (not shown). In examples: an unsaturated ester is obtained by reacting formic acid with dicyclopentadiene in the presence of perchloric acid and is converted to an ester-aldehyde by heating with carbon monoxide and hydrogen using a cobalt oleate catalyst (I); in a similar process acetic acid is used instead of formic acid (II); in similar processes palmitic acid is employed instead of acetic acid using perchloric acid and a boron-trifluoride-phosphoric acid complex as catalyst in the first stage (III); the dimethylol derivative of the acetate of hydroxy-dihydro-dicyclopentadiene is obtained by treating with formaldehyde in an aqueous alcoholic potash solution the product obtained by oxonation of the acetate ester of hydroxy-dihydro-dicyclopentadiene (IV); and the dimethylol product of Example (IV) is converted to the valerate ester by heating with normal valeric acid and toluene sulphonic acid in toluene solution (V). The conversion of portions of the crude aldehyde-esters obtained in Examples (I) and (II) to hydroxy esters by hydrogenation over a nickel catalyst and the hydrolysis of the hydroxy ester obtained in (I) to the corresponding cyclic dihydric alcohol are described. The trivalerate ester obtained in (V) is employed as a plasticizer in polyvinyl chloride resin compositions (see Group IV (a)).
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US815232XA | 1954-12-31 | 1954-12-31 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB815232A true GB815232A (en) | 1959-06-24 |
Family
ID=22164735
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB34355/55A Expired GB815232A (en) | 1954-12-31 | 1955-11-30 | Bifunctional products from oxo reaction |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB815232A (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4275251A (en) | 1980-04-29 | 1981-06-23 | International Flavors & Fragrances Inc. | Substituted tricyclodecane derivatives, processes for producing same and organoleptic uses thereof |
US4318863A (en) * | 1980-04-29 | 1982-03-09 | International Flavors & Fragrances Inc. | Substituted tricyclodecane derivatives, processes for producing same and organoleptic uses thereof |
US4358617A (en) * | 1980-04-29 | 1982-11-09 | International Flavors & Fragrances Inc. | Substituted tricyclodecane derivatives, processes for producing same and organoleptic uses thereof |
US4430508A (en) | 1980-12-29 | 1984-02-07 | International Flavors & Fragrances Inc. | Substituted tricyclodecane derivatives, processes for producing same and organoleptic uses thereof |
DE3317476A1 (en) * | 1983-05-13 | 1984-11-22 | Dragoco Gerberding & Co Gmbh, 3450 Holzminden | MIXTURES OF TRICYCLODECAN DERIVATIVES AND THE PRODUCTION AND USE THEREOF AS A SMELLING AND FLAVORING SUBSTANCE |
CN103193639A (en) * | 2012-01-10 | 2013-07-10 | 南昌洋浦天然香料香精有限公司 | Synthetic method of perfume verdyl acetate |
CN103524339A (en) * | 2012-07-05 | 2014-01-22 | 国际香料和香精公司 | 3A,4,5,6,7,7A-cyclohe-3H-4,7-ylmethyl-indene-5-base ester and preparation method thereof |
-
1955
- 1955-11-30 GB GB34355/55A patent/GB815232A/en not_active Expired
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4275251A (en) | 1980-04-29 | 1981-06-23 | International Flavors & Fragrances Inc. | Substituted tricyclodecane derivatives, processes for producing same and organoleptic uses thereof |
US4318863A (en) * | 1980-04-29 | 1982-03-09 | International Flavors & Fragrances Inc. | Substituted tricyclodecane derivatives, processes for producing same and organoleptic uses thereof |
US4358617A (en) * | 1980-04-29 | 1982-11-09 | International Flavors & Fragrances Inc. | Substituted tricyclodecane derivatives, processes for producing same and organoleptic uses thereof |
US4430508A (en) | 1980-12-29 | 1984-02-07 | International Flavors & Fragrances Inc. | Substituted tricyclodecane derivatives, processes for producing same and organoleptic uses thereof |
DE3317476A1 (en) * | 1983-05-13 | 1984-11-22 | Dragoco Gerberding & Co Gmbh, 3450 Holzminden | MIXTURES OF TRICYCLODECAN DERIVATIVES AND THE PRODUCTION AND USE THEREOF AS A SMELLING AND FLAVORING SUBSTANCE |
DE3317476C2 (en) * | 1983-05-13 | 1988-04-07 | Dragoco Gerberding & Co Gmbh, 3450 Holzminden, De | |
CN103193639A (en) * | 2012-01-10 | 2013-07-10 | 南昌洋浦天然香料香精有限公司 | Synthetic method of perfume verdyl acetate |
CN103524339A (en) * | 2012-07-05 | 2014-01-22 | 国际香料和香精公司 | 3A,4,5,6,7,7A-cyclohe-3H-4,7-ylmethyl-indene-5-base ester and preparation method thereof |
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