N-dodecyldodecan-1-amine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 250 ml flask fitted with a mechanical stirrer and a reflux condenser, were placed 30.7 g (0.12 mole) of the 2-hydroxy-3,4,6-trimethylbenzoic acid phenyl ester prepared in step (2) and 42.36 g (0.12 mole) of didodecylamine. This mixture was heated in a nitrogen atmosphere at 120° C. for 12 hours. The phenol formed was distilled off under vacuum (7 g were thus collected). After cooling, the crystallization of the desired product was started by scraping. In a 250 ml flask fitted with a mechanical stirrer and a reflux condenser

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of didodecylamine 66 (25 g, 70 7 mmol) and diisopropylethylamine (18 g, 141 mmol) in anhydrous CH2Cl2 (700 mL) at −10° C., a solution of acryloyl chloride (7.68 g, 85 mmol) in CH2Cl2 (100 mL) was added dropwise over a period of 20 min. After the completion of the addition the reaction mixture was stirred for 4 h at 0° C. after which the TLC of the reaction mixture showed the completion of the reaction. The reaction mixture was washed with satd. NaHCO3 solution (200 mL), water (200 mL), brine (100 mL) and dried over NaSO4. Concentration of the organic layer provided the product 71 (28.4 g, 100%) which was used as such in the next step. 1H NMR CDCl3 δ 0.94 (t, J=6.5 Hz, 6H), 1.05-1.69 (m, 40H), 3.15-3.60 (dt, 4H), 5.64 (d, 1H), 6.36 (d, 1H), 6.63 (m, 1H). After the completion of the addition the reaction mixture the completion of the reaction The reaction mixture was washed with satd NaHCO3 solution (200 mL), water (200 mL), brine (100 mL) and dried over NaSO4

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

Procedure: A mixture of 18.1 g (0.063 mole) 1-acetoxy-4-naphthalenesulfonyl chloride, 22.4 g (0.063 mole) N,N-didodecylamine, 25 ml (18.1 g, 0.18 mole) triethylamine, and 200 ml acetonitrile was stirred at room temperature for 18 hrs. The mixture was diluted with ether and poured into water. The ether layer was separated, dried, and concentrated to 16.1 g of an amber oil, which was dissolved in 100 ml ethanol. To the solution was added 1.50 g (0.027 mole) potassium hydroxide; the mixture was stirred at room temperature for 2 days, acidified with hydrochloric acid, and diluted with water. The mixture was extracted with ether, and the extract was concentrated to 30.7 g of an amber oil, which partially crystallized. The ether layer was separated dried concentrated to 16.1 g of an amber oil, which was dissolved in 100 ml ethanol the mixture was stirred at room temperature for 2 days The mixture was extracted with ether the extract was concentrated to 30.7 g of an amber oil, which partially crystallized

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

Procedure: The same procedure as in Example 15 was repeated except for using 150 g (0.81 mol) of lauryl alcohol in place of stearyl alcohol and using ammonia in an amount of 69 g (4.06 mol), thereby conducting the reaction for 9 h. The initial maximum pressure as measured at a reaction temperature of 220° C. was 21 MPaG. The resultant reaction product was analyzed in the same manner as in Example 15. As a result, it was confirmed that the conversion of the raw alcohol was 96.3%, the selectivity to lauryl amine was 90.9%, the amount of dilauryl amine produced is 8.2%, and the amount of the other by-products produced was 0.6%. the reaction for 9 h as measured at a reaction temperature of 220° C. The resultant reaction product

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

Procedure: The same procedure as in Example 13 was repeated except for using the catalyst (K) produced in Preparation Example 10 in place of the catalyst (G), flowing ammonia and hydrogen through the autoclave at rates of 13.1 g (0.77 mol)/h and 4.3 L (0.19 mol)/h, respectively, thereby conducting the reaction for 6 h. The resultant reaction product was analyzed in the same manner as in Example 7. As a result, it was confirmed that the conversion of the raw alcohol was 65.5%, the selectivity to lauryl amine was 85.5%, the amount of dilauryl amine produced is 7.3%, and the amount of the other by-products produced was 2.2%. the reaction for 6 h The resultant reaction product

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

Procedure: A 500 mL autoclave of an electromagnetic induction rotary agitation type was charged with 150 g (0.55 mol) of stearyl alcohol and 3 g of the catalyst (G) produced in Preparation Example 6 (2.0% by mass on the basis of the raw alcohol), and then the contents of the autoclave were heated to 220° C. in a hydrogen atmosphere (0 MPaG) while stirring (at 1000 rpm). Then, while flowing ammonia and hydrogen through the autoclave at rates of 19.1 g (1.1 mol)/h and 2.6 L (0.12 mol)/h, respectively, so as to maintain the reaction pressure at a constant value of 2.0 MPaG, the reaction was conducted for 3 h. The resultant reaction product was filtered to remove the catalyst therefrom, and then subjected to gas chromatography to analyze a composition thereof. As a result, it was confirmed that the conversion of the raw alcohol was 96.0%, the selectivity to lauryl amine was 78.1%, the amount of dilauryl amine produced is 13.4%, and the amount of the other by-products produced was 7.6%. produced in Preparation Example 6 (2.0% by mass on the basis of the raw alcohol), and then the contents of the autoclave respectively, so as to maintain The resultant reaction product was filtered to remove the catalyst

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

Procedure: The same procedure as in Example 7 was repeated except for using 150 g (0.81 mol) of lauryl alcohol in place of stearyl alcohol and using ammonia in an amount of 69 g (4.06 mol), thereby conducting the reaction for 9 h. The initial maximum pressure as measured at a reaction temperature of 220° C. was 21 MPaG. The resultant reaction product was analyzed in the same manner as in Example 7. As a result, it was confirmed that the conversion of the raw alcohol was 97.9%, the selectivity to lauryl amine was 90.4%, the amount of dilauryl amine produced is 8.9%, and the amount of the other by-products produced was 0.6%. the reaction for 9 h as measured at a reaction temperature of 220° C. The resultant reaction product

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

Procedure: The same procedure as in Example 3 was repeated except for using 150 g (0.81 mol) of lauryl alcohol in place of stearyl alcohol and using ammonia in an amount of 69 g (4.06 mol), thereby conducting the reaction for 11 h. The initial maximum pressure as measured at a reaction temperature of 220° C. was 21 MPaG. The resultant reaction product was analyzed in the same manner as in Example 1. As a result, it was confirmed that the conversion of the raw alcohol was 96.3%, the selectivity to lauryl amine was 74.9%, the amount of dilauryl amine produced is 12.3%, and the amount of the other by-products produced was 10.9%. the reaction for 11 h as measured at a reaction temperature of 220° C. The resultant reaction product

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Linalyl chloroacetate (5.77 g, 25 mmol, 1 eq), in toluene (50 ml), was slowly added to didodecylamine (10 g, 28.3 mmol, 1.13 eq) and sodium carbonate (5.3 g, 0.05 mol, 2 eq), in toluene (50 ml). The reaction mixture was stirred at 60° C. for two weeks after which the reaction seemed completed by 1H NMR. The sodium carbonate was filtered off, the filtrate was concentrated under vacuum and diethyl ether (200 ml) was added before storage of the solution at 4° C. for 12 hours. Then, the solution was filtered and removal of ether under vacuum yielded to the expected N,N-didodecylglycine linalyl ester as a yellow oil. The sodium carbonate was filtered off the filtrate was concentrated under vacuum and diethyl ether (200 ml) was added before storage of the solution at 4° C. for 12 hours Then, the solution was filtered removal of ether under vacuum

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 250 ml flask fitted with a mechanical stirrer and a reflux condenser, were placed 30.7 g (0.12 mole) of the 2-hydroxy-3,4,6-trimethylbenzoic acid phenyl ester prepared in step (2) and 42.36 g (0.12 mole) of didodecylamine. This mixture was heated in a nitrogen atmosphere at 120° C. for 12 hours. The phenol formed was distilled off under vacuum (7 g were thus collected). After cooling, the crystallization of the desired product was started by scraping. In a 250 ml flask fitted with a mechanical stirrer and a reflux condenser

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 250 ml flask fitted with a mechanical stirrer and a reflux condenser, were placed 30.7 g (0.12 mole) of the 2-hydroxy-3,4,6-trimethylbenzoic acid phenyl ester prepared in step (2) and 42.36 g (0.12 mole) of didodecylamine. This mixture was heated in a nitrogen atmosphere at 120° C. for 12 hours. The phenol formed was distilled off under vacuum (7 g were thus collected). After cooling, the crystallization of the desired product was started by scraping. In a 250 ml flask fitted with a mechanical stirrer and a reflux condenser