Ethylene Oxide → Undecylenic Acid

HRID 2355237Notes

Reaction equation

HRID 2355237 reaction equation
C1OC1.C1OC1C.C1OC1C.C1OC1.[C:15]([OH:27])(=[O:26])[CH:16]=[CH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].[OH-].[K+]>>[C:15]([OH:27])(=[O:26])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH:24]=[CH2:25]

Participants

6

Reactant 5

HCID 6354Ethylene OxideHCID 6378Propylene OxideHCID 14797Potassium Hydroxide2×HCID 24751Crl-8131HCID 519180Hendecenoic acid

Product 1

HCID 5634Undecylenic Acid

Conditions

Temperature
120 °C

Procedure

In a 4 l multi-necked flask, 1829.9 g (0.7 mol) of an α,ω-dihydroxypoly(ethylene oxide-propylene oxide) copolymer having a hydroxyl number of 41.5 (mg KOH)/g with 50% by mass propylene oxide content and with ethylene oxide end blocks were heated with 249.4 g (1.4 mol) of undecenoic acid (molar mass: 184.3 g/mol, acid number: 304.4 mg KOH/g) to 70° C. with stirring and then 41.6 g of Novozym® 435 (2% by mass based on the total batch) were added. At 4 mbar and with further continual stirring, and also with the introduction of a gentle stream of nitrogen (˜2000 ml/h), the reaction mixture was reacted for 23 hours. During this time the initial acid number of the reaction mixture fell from originally 35.8 mg KOH/g solids to 1.4 mg KOH/g solids. Following filtration and 2-hour heat treatment at 120° C., the α,ω-bis-undecenoato-poly(ethylene oxide-propylene oxide) copolymer was ready for use for the subsequent reactions.

Workup

  1. additionwere added
  2. customAt 4 mbar and with further continual stirring, and also with the introduction of a gentle stream of nitrogen (˜2000 ml/h), the reaction mixture was reacted for 23 hours
  3. filtrationfiltration and 2-hour

Sources & evidence

ORD record
ord-456d6643fcb249b5948246ba6288a1e8
Source dataset
uspto-grants-2010_07
Patent number
US07754778B2

Reaction notes

Loading…