1,2-Hexadecanediol → Pentadecanediol Octadecanediol

HRID 1248070

Reaction equation

HRID 1248070 reaction equation
C(O)C(O)CCCCCCCCCCCCC.C(O)C(O)CCCCCCCCCCCCCC.C(O)C(O)CCCCCCCCCCCCCCC.[CH:55]([OH:74])([OH:73])[CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH3:72].P([O-])(OC)OC>CO>[CH:55]([OH:73])([OH:74])[CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH3:69].[CH:55]([OH:73])([OH:74])[CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH3:72]

Participants

7

Conditions

Temperature
70 °C

Procedure

Approximately 360 g of 1,2-mixed pentadecanediol to octadecanediol (commercially obtained as Vikol 158 from Viking Chemical Co. and containing about 28% 1,2-pentadecanediol, about 28% 1,2-hexadecanediol, about 28% 1,2-heptadecanediol and about 16% octadecanediol, all percentages by weight) were charged to a glass reactor equipped with heater, agitator, Dean-Stark tube with condenser and provision for blanketing the vapor space with nitrogen. The contents were heated to 70° C. to liquify the solids and 55 g of dimethyl phosphite were slowly added. The reaction mixture was heated to 110° C. and held for 2 hours, held at 120° C. for 1 hour and held at 130° C. for 1 hour. Methanol was observed forming and collecting in the trap. The crude product was vacuum stripped at 150° C. to remove volatile materials, producing 375 g of intermediate additive. The intermediate was an amber fluid which became waxy after cooling.

Workup

  1. additionall percentages by weight) were charged to a glass reactor
  2. customequipped with heater, agitator, Dean-Stark tube with condenser
  3. additionwere slowly added
  4. temperatureThe reaction mixture was heated to 110° C.
  5. waitheld at 120° C. for 1 hour
  6. waitheld at 130° C. for 1 hour
  7. customcollecting in the trap
  8. customstripped at 150° C.
  9. customto remove volatile materials

Sources & evidence

ORD record
ord-47186f20d039468fbee398b1fe8e76a8
Source dataset
uspto-grants-1985_06
Patent number
US04522629

Linked notes

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