Octylphosphonic acid

DryPowder; Liquid; WetSolid, Liquid

2.5 ml of 1-bromooctane was charged at room temperature into a 1000 ml flask, 12.9 g of aluminum trichloride was added, Stir evenly, And then heated to 85 deg C, 1.0 mol of triethyl phosphite was added dropwise, Temperature control between 85 ~ 105 deg C, 3.0h drop finished. After the dropwise addition, Heating up to 160 ° C, Insulation for 4h to continue the reaction. After the reaction, Cooling to 80 deg C, 506.0 g of a 40percent aqueous solution of hydrogen bromide was added dropwise to the reaction system, 60min drop finished. After the dropwise addition, Heated to reflux state, Maintain 4h to react. After the reaction, The aqueous bromine solution was distilled off at 105 ° C under normal pressure, Recovering these aqueous hydrogen bromide solutions; At a vacuum of 2.5 kPa, 90 under the conditions of 1 - bromooctane distillation; Then down to room temperature, A mixed solution of n-hexane and water in a volume ratio of 6: 1 was poured into a reactor, After mixing all into the separatory funnel, Extraction liquid separation; The lower aqueous liquid recovery, The upper oil phase is transferred to the flask, The n-hexane was distilled off at atmospheric pressure at 85 ° C, Recovering these n-hexane, To give 1-octylphosphonic acid; The yield of the reaction was 95.1percent; Sampling analysis, The chromatographic purity of the product was 98.2percent.The method comprises the following steps: (1) adding n-octyl phosphonic acid diethyl ester and 37percent wt hydrochloric acid into a reaction kettle, then dropping 93percent wt sulfuric acid (1.2 hours) After 93percent wt of sulfuric acid was added dropwise, the temperature was raised to 118 ° C and maintained for 50 hours. The reaction mixture was naturally cooled to 65 ° C. After the reaction, the material was discharged from the reaction vessel. After the reaction, the material was cooled to 35 ° C, And the mass ratio of diethyl n-octylphosphonate and 37percent wt hydrochloric acid is 11.9; the mass ratio of diethyl n-octylphosphonate and 93percent wt sulfuric acid is (N-heptane added to the mass of 0.8 times the mass of solid), heated to 75 ° C and 0.5 hours, the temperature dropped to 55 ° C after the material (1: 1, 0.05); (2) the solid added to the re-crystallization reactor, And the mixture was cooled to 35 ° C and allowed to stand at 35 ° C for 12 hours or more to obtain a solid by centrifugal separation. (3) Step 3 was repeated to obtain the n-octylphosphonic acid product (yield: 82.6percent , Purity 99.2percent).66.5 g (0.4 mol) of triethyl phosphite and 77.3 g (0.4 mol) of 1-bromooctane were placed in a 300 mL eggplant-shaped flask equipped with a cooling tube, and the mixture was heated and stirred at 100 °C for 8 hours under a nitrogen stream and reacted. After cooling down, adjust the equipment for distillation, gently raise the temperature to 120 °C under reduced pressure of 10 Torr (1.33 × 103 Pa), heat to remove unreacted raw materials and reaction byproducts, and 83.7 g (84percent) of diethyl octylphosphonate which is colorless and transparent was obtained. 5.0 g of diethyl octylphosphonate and 22 mL of 48percent hydrobromic acid were placed in a 100 mL recovery flask equipped with a Dean-Stark trap and a cooling tube, gradually heated to 160 °C and stirred at that temperature for 2.5 hours. When the reaction mixture was cooled, colorless and transparent plate crystals were precipitated, and then filtered and dried to obtain 2.7 g (70percent) of the product.General procedure: Alkylbromide (4.27 g of 1-bromo-3, 3, 4, 4, 5, 5, 6, 6, 7, 7, 8, 8, 8-tride-cafluorooctane or 1.93 g of 1-bromooctane, 10 mmol) was heated with triethyl phosphite (1.83 g, 11 mmol) for 4 h at 150 °C. After cooling, conc. HBr (12 ml) was added and heated for 4 h at 120 °C.The excess HBr and bromoethane was then distilled off and the crude products were crystallized. The same procedure of hydrolysis of diester 4 obtained by first synthetic approach was also used.To an oven-dried 100 mL two-neck flask, fitted with a reflux condenserwere added anhyd ZnCl2 (0.75 g, 5.5 mmol, 0.65 equiv) andanhyd Et2O (20 mL). The mixture was cooled in an ice-bath and octylmagnesiumbromide (4.2 mL, 8.4 mmol, 1 equiv) was slowly added.The reaction mixture was stirred 10 more min at 0 °C followed by 2 hat r.t. The solution was then cooled in an ice-salt mixture and POCl3(0.78 mL, 8.4 mmol, 1 equiv) was added. After stirring with coolingfor 5 min, the mixture was brought to r.t. and stirred for 20 h. Themixture was cooled again in an ice-salt mixture and H2O (5 mL) wasslowly added. Stirring with cooling for 5 min was followed by reactionat r.t. for 25.5 h. The crude mixture was then poured into CH2Cl2(100 mL), washed three times with dil HCl (1–2percent, 100 mL in total), dried (MgSO4), filtered, and evaporated to dryness. The resultingcrude product was purified by recrystallization from hot heptane (50mL), filtered and washed with pentane, providing the pure compoundas a white solid; yield: 0.49 g (30percent); mp 100–102 °C.IR (ATR): 2918, 1468, 1106, 994, 943, 778, 715 cm–1.1H NMR (CDCl3, 400 MHz): δ = 9.53 (s, 2 H), 1.81–1.68 (m, 2 H), 1.68–1.55 (m, 2 H), 1.41–1.33 (m, 2 H), 1.33–1.22 (m, 8 H), 0.88 (t, J = 6.8Hz, 3 H).13C NMR (CDCl3, 100 MHz): δ = 31.9, 30.7, 30.5, 29.2, 29.2, 26.1, 24.7, 22.8, 22.2, 22.1, 14.2.31P NMR (CDCl3, 162 MHz): δ = 37.7.MS (ESI): m/z = 193 [M – H]–, 387 [2 M – H]–, 581 [3 M – H]–, 603[3 M – 2 H + Na]–, 797 [4 M – 2 H + Na]–.Anal. Calcd for C8H19O3P: C, 49.48; H, 9.86. Found: C, 49.19; H, 9.71.

Corrosion inhibitors and anti-scaling agents

Cleaning and furnishing care products

100,000 - 500,000 lb

Molecular Weight:194.21
XLogP3:1.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:7
Exact Mass:194.10718146
Monoisotopic Mass:194.10718146
Topological Polar Surface Area:57.5
Heavy Atom Count:12
Complexity:141
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes