Hydrochloric Acid → HCID 11125018, compound

HRID 1577491Notes

Reaction equation

HRID 1577491 reaction equation
[P:1](Cl)(=[O:20])([O:11][CH2:12][CH:13]([CH2:18][CH3:19])[CH2:14][CH2:15][CH2:16][CH3:17])[O:2][CH2:3][CH:4]([CH2:9][CH3:10])[CH2:5][CH2:6][CH2:7][CH3:8].[CH3:22][CH2:23][CH2:24][CH2:25][CH:26]([CH2:29][O:30][PH:31]([O:33][CH2:34][CH:35]([CH2:38][CH2:39][CH2:40][CH3:41])[CH2:36][CH3:37])=[O:32])[CH2:27][CH3:28].C(C(CCCC)C[O:46]P(=O)(O)O)C.Cl>O>[O:2]([CH2:3][CH:4]([CH2:9][CH3:10])[CH2:5][CH2:6][CH2:7][CH3:8])[P:1]([O:20][P:31]([O:33][CH2:34][CH:35]([CH2:36][CH3:37])[CH2:38][CH2:39][CH2:40][CH3:41])([O:30][CH2:29][CH:26]([CH2:27][CH3:28])[CH2:25][CH2:24][CH2:23][CH3:22])=[O:32])(=[O:46])[O:11][CH2:12][CH:13]([CH2:18][CH3:19])[CH2:14][CH2:15][CH2:16][CH3:17].[CH3:8][CH2:7][CH2:6][CH2:5][CH:4]([CH2:3][O:2][PH:1]([O:11][CH2:12][CH:13]([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:18][CH3:19])=[O:20])[CH2:9][CH3:10]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 140502-Ethylhexyl dihydrogen phosphateHCID 173926Bis(2-ethylhexyl) phosphorochloridateHCID 178443864HCID 178443864, compound2×

Product 2

HCID 11125018HCID 11125018, compoundHCID 178443864HCID 178443864, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

The final major step in the process of this invention is the hydrolysis of the di-(2-ethylhexyl) phosphorochloridate to product DEHPA. This reaction is carried out using an excess amount of water over the stoichiometric amount. Dealkylation of the DEHPA to mono-(2-ethylhexyl) phosphoric acid by HCl at elevated temperatures is a side reaction that must be controlled to produce acceptable product. This dealkylation is minimized by adjusting the amount of water so that a final HCl content below about 11 wt. % is obtained. In general, the hydrolysis reaction is carried out at 80°-100° C. Considerable amounts (above 60 wt. %) of tetra-(2-ethylhexyl) pyrophosphate are formed in this process from the reaction of DEHPC with DEHPA. This lowers product purity and causes processing problems, such as poorer phase separation. This is overcome by extending the hydrolysis time to 4-6 hours to hydrolyze the pyrophosphate to DEHPA product. An alternative and preferred method to carry out the hydrolysis is to hydrolyze the mixture, as above described for about 2 hours at about 80° C. Then the aqueous layer containing the HCl is separated. A second hydrolysis, using the same amount of water as previously stated, is carried out at 95°-100° C. for about 3 hours.

Workup

  1. customa side reaction that
  2. customto produce acceptable product
  3. customis obtained
  4. customIn general, the hydrolysis reaction
  5. customis carried out at 80°-100° C

Sources & evidence

ORD record
ord-60c511417eed442ebcd7f2a5706018b4
Source dataset
uspto-grants-1981_09
Patent number
US04288392

Reaction notes

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