Propylene Glycol → Dicyclopentadiene

HRID 1447911Notes

Reaction equation

HRID 1447911 reaction equation
S(=O)(=O)(O)O.[C:6]1([CH3:16])[CH:11]=[CH:10][C:9](S(O)(=O)=O)=[CH:8][CH:7]=1.B(F)(F)F.[CH2:21](O)[CH:22](O)C.O[CH2:27]C(C)(CO)C.C(O)CC(O)C.C(O)CCCCCO.CC(O)COC(CO)C.S(CCO)CCO>C(O)COCCO.C(O)CO.CCOCC>[CH2:21]1[CH:7]2[CH:8]3[CH:9]=[CH:10][CH:11]([CH:6]2[CH:16]=[CH:22]1)[CH2:27]3

Participants

13

Reactant 9

HCID 1030Propylene GlycolHCID 1118Sulfuric AcidHCID 5447ThiodiglycolHCID 6101p-Toluenesulfonic acidHCID 6356Boron trifluorideHCID 78961,3-ButanediolHCID 123741,6-HexanediolHCID 31344Neopentyl glycolHCID 328812-(2-Hydroxypropoxy)-1-propanol

Product 1

HCID 6492DicyclopentadieneYield 60%

Reagents, catalysts & solvents 3

HCID 174Ethylene GlycolSolventHCID 3283Diethyl EtherSolventHCID 8117Diethylene GlycolSolvent

Procedure

Suitable acid catalysts for producing the ether include sulfuric acid, p-toluenesulfonic acid, boron trifluoride, beads or permeable sheets of acid ion-exchange resins, especially such resins containing sulfonic acid groups, such as the product available commercially under the registered trademark Amberlyst 15. Examples of (C2 to C6) diols or glycols that may be used include ethylene glycol, propylene glycol, neopentyl glycol, 1,3-butylene glycol, 1,6-hexanediol, diethylene glycol, dipropylene glycol, thiodiethanol, etc. The monohydroxy-glycol ether obtained in the first step of the reaction may be, and preferably is, isolated by distillation (generally with a 60-85% yield) from less volatile by-products such as bis-dicyclopentenyl ether and low polymers of dicyclopentadiene.

Workup

  1. additioncontaining sulfonic acid groups
  2. customobtained in the first step of the reaction

Sources & evidence

ORD record
ord-f6d4406d56d641538e98b9b859ac9a10
Source dataset
uspto-grants-1979_12
Patent number
US04178425

Reaction notes

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