7-methyloctanoic acid

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.2% Product of addition of 9 mols of ethylene oxide+10 mols of propylene oxide to nonylphenol

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 94 parts by weight of phenol are dissolved in 166 parts by weight of isononanoic acid. 107 parts by weight of 96% sulfuric acid are then added to this solution and the mixture is heated for 30 minutes to 100° to 110° C. The water of reaction is then largely distilled off under reduced pressure (20 mm) within 30 minutes. After cooling, 134 parts by weight of thionylchloride are added dropwise at 45° to 50° C., with addition of an antifoam. The mixture is stirred for one further hour. This gives a stable isononanoyloxybenzenesulfonic acid havingan AS content of 81%, and the Na salt as the end product, which is obtained in virtually quantitative yield (relatative to phenol), has an AS content of 85%. is then largely distilled off under reduced pressure (20 mm) within 30 minutes After cooling 134 parts by weight of thionylchloride are added dropwise at 45° to 50° C., with addition of an antifoam

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 94 parts by weight of phenol are dissolved in 166 parts by weight of isononanoic acid. 107 parts by weight of 96% sulfuric acid are then added to this solution and the mixture is heated for 30 minutes to 100° to 110° C. The water of reaction is then largely distilled off under reduced pressure (20 mm) within 30 minutes. After cooling, 134 parts by weight of thionylchloride are added dropwise at 45° to 50° C., with addition of an antifoam. The mixture is stirred for one further hour. This gives a stable isononanoyloxybenzenesulfonic acid havingan AS content of 81%, and the Na salt as the end product, which is obtained in virtually quantitative yield (relatative to phenol), has an AS content of 85%. is then largely distilled off under reduced pressure (20 mm) within 30 minutes After cooling 134 parts by weight of thionylchloride are added dropwise at 45° to 50° C., with addition of an antifoam

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Diisobutene, either prepared by the oligomerization of pure isobutene obtained by redissociation or obtained in the course of workup of a butadiene-free raffinate I, is then converted to a C9 derivative lengthened by one carbon atom. Industrial operation involves the hydroformylation or oxo process in which diisobutene is converted to the corresponding aldehyde with carbon monoxide and hydrogen in the presence of rhodium or cobalt catalysts. Since diisobutene predominantly comprises the octenes 2,4,4-trimethyl-1-pentene and 2,4,4-trimethyl-2-pentene, the hydroformylation reaction gives the C9 aldehyde 3,5,5-trimethylhexanal as the main constituent. Further C9 isomers present in small amounts are 3,4,4- and 3,4,5-trimethylhexanal, and also 2,5,5-trimethylhexanal, 4,5,5-trimethylhexanal and 6,6-dimethylheptanal. Oxidation of this aldehyde mixture gives an industrially available isononanoic acid typically having a content of 3,5,5-trimethylhexanoic acid of about 90% (Ullmanns Encyklopädie der technischen Chemie, 4th Edition, 1975, Verlag Chemie, Volume 9, pages 143-145; EP 1 854 778 A1).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Diisobutene, either prepared by the oligomerization of pure isobutene obtained by redissociation or obtained in the course of workup of a butadiene-free raffinate I, is then converted to a C9 derivative lengthened by one carbon atom. Industrial operation involves the hydroformylation or oxo process in which diisobutene is converted to the corresponding aldehyde with carbon monoxide and hydrogen in the presence of rhodium or cobalt catalysts. Since diisobutene predominantly comprises the octenes 2,4,4-trimethyl-1-pentene and 2,4,4-trimethyl-2-pentene, the hydroformylation reaction gives the C9 aldehyde 3,5,5-trimethylhexanal as the main constituent. Further C9 isomers present in small amounts are 3,4,4- and 3,4,5-trimethylhexanal, and also 2,5,5-trimethylhexanal, 4,5,5-trimethylhexanal and 6,6-dimethylheptanal. Oxidation of this aldehyde mixture gives an industrially available isononanoic acid typically having a content of 3,5,5-trimethylhexanoic acid of about 90% (Ullmanns Encyklopädie der technischen Chemie, 4th Edition, 1975, Verlag Chemie, Volume 9, pages 143-145; EP 1 854 778 A1).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 122 parts by weight of ClSO3H are added, at a temperature of 40° C., to 94 parts by weight of phenol in 158.5 parts by weight of isononanoic acid, and stirring is continued for a further hour at 40° C. 125 parts of SOCl2 are then metered in at such a rate that the evolution of gas takes place in a controlled manner, after which stirring is continued for a further hour. The Na salt of isononanoyloxybenzenesulfonic acid obtained after further working up as described in V1 has a D-content of 85% and an isomer ratio of 3.3 to 1. is continued for a further hour at 40° C after which stirring is continued for a further hour

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 122 parts by weight of ClSO3H are added, at a temperature of 40° C., to 94 parts by weight of phenol in 158.5 parts by weight of isononanoic acid, and stirring is continued for a further hour at 40° C. 125 parts of SOCl2 are then metered in at such a rate that the evolution of gas takes place in a controlled manner, after which stirring is continued for a further hour. The Na salt of isononanoyloxybenzenesulfonic acid obtained after further working up as described in V1 has a D-content of 85% and an isomer ratio of 3.3 to 1. is continued for a further hour at 40° C after which stirring is continued for a further hour

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 122 parts by weight of ClSO3H are added, at a temperature of 40° C., to 94 parts by weight of phenol in 158.5 parts by weight of isononanoic acid, and stirring is continued for a further hour at 40° C. 125 parts of SOCl2 are then metered in at such a rate that the evolution of gas takes place in a controlled manner, after which stirring is continued for a further hour. The Na salt of isononanoyloxybenzenesulfonic acid obtained after further working up as described in V1 has a D-content of 85% and an isomer ratio of 3.3 to 1. is continued for a further hour at 40° C after which stirring is continued for a further hour

Conditions: temp:200.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a four-neck 1000 mL flask equipped with a stirrer, a thermometer, a gas inlet tube, and a Dean-Stark condenser with a water measuring trap were placed 166.2 g (1.0 mol) of diglycerin, 237.3 g (1.5 mol) of isononanoic acid, and 150 mL of toluene as a solvent. Then, the reaction mixture was heated to 200 degrees C. under a flow of nitrogen gas in a rate of 20 mL/min. At the temperature, the reaction took place while distilling off the produced water with the solvent azeotropically. When the distillation-off water subsided, the temperature was raised to 220 degrees C. to further continue the reaction. When the distillation-off water stopped, the reaction was terminated. It took about 6 hours from the start of the reaction to this point. Diglycerin isononanoate was obtained as a pale yellow viscous oil in an amount of 411.5 g (hydroxyl value: 132, acid value: 0.3). In a four-neck 1000 mL flask equipped with a stirrer a thermometer, a gas inlet tube, and a Dean-Stark condenser with a water measuring trap were placed while distilling off the produced water with the solvent azeotropically the temperature was raised to 220 degrees C the reaction the reaction was terminated It took about 6 hours from the start of the reaction to this point

Conditions: temp:180.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 1 liter stirred reactor, equipped with a distillation column, condenser, and graduated receiver, the following constituents were added: 331.2 g of diisopropanol amine (DIPA) and 390.5 g (98%) of isononanoic acid. The contents were heated to 180° C. under a nitrogen blanket. After 3.5 hours, 43.4 g of water was collected overhead. The pressure was then slowly lowered to strip out unreacted DIPA. At a batch temperature of 183° C. and a pressure of 60 Pa, a cut consisting of 188 g of DIPA was removed. The batch temperature was then raised to 200° C. and the pressure dropped 333 Pa. During this period, a cut of 220 g of the amide acetal was recovered. The water of reaction passed through the condenser and was not captured with the amide acetal. This represents a 35% conversion of the isononanoic acid to amide acetal. equipped with a distillation column, condenser the following constituents were added 43.4 g of water was collected overhead At a batch temperature of 183° C. was removed The batch temperature was then raised to 200° C. the pressure dropped 333 Pa During this period a cut of 220 g of the amide acetal was recovered The water of reaction

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A reaction between 160 g of isononanoic acid and 160 g of isodecyl alcohol was carried out as in Example 1, obtaining 141 g of the desired ester.

Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In the equipment according to FIG. 1, a mixture of 178.8 g (1.53 mole) of chlorosulfonic acid and 136.5 g (0.86 mole) of isononanoic acid was placed into one of the two graduated funnels and a mixture of 143 g (1.52 mole) of phenol and 104 g (0.66 mole) of isononanoic acid was placed into the other, and the two mixtures were added under control to the continuous-flow reactor in such a way that the residence time was about 7 minutes. The total time for adding the starting compounds to the reactor under control was about 2 hours. The reactor, heated to 95° C. under thermostatic control, had a length of 60 cm and was packed with glass rings. Throughout the reaction period, 10 liters of nitrogen per hour were passed through the receiver and through the reactor. This gave a 93.3% yield of crude phenolsulfonic acid diluted with isononanoic acid, of the following composition: were added under control to the continuous-flow reactor in such a way that the residence time The total time for adding the starting compounds to the reactor under control was about 2 hours Throughout the reaction period, 10 liters of nitrogen per hour