Terephthalic Acid → Phosphorus

HRID 1914970Notes

Reaction equation

[Sb+]=O.[CH2:3]([P:5]([CH2:11][CH2:12][CH2:13][OH:14])(=[O:10])[O:6][CH2:7][CH2:8][OH:9])[CH3:4].[C:15]([OH:26])(=[O:25])[C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=1.[P:27]([O-])([O-])([O-])=O.[Na+].[Na+].[Na+]>C([O-])(=O)C.[Zn+2].C([O-])(=O)C.C(O)CO>[C:15]([OH:26])(=[O:25])[C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=1.[CH2:3]([P:5]([CH2:11][CH2:12][CH2:13][OH:14])(=[O:10])[O:6][CH2:7][CH2:8][OH:9])[CH3:4].[P:27]

Participants

Conditions

Temperature: 200 °C

Procedure

Terephthalic acid, ethylene glycol and 2-hydroxyethyl ethyl(3-hydroxy-propyl)phosphinate (produced as in Example 11) are polymerized in a weight ratio of 1000:650:70 in the presence of zinc acetate and antimony(III) oxide under the usual conditions. To 19.6 g of 2-hydroxyethyl ethyl(3-hydroxypropyl)phosphinate are added 290 g of terephthalic acid, 188 g of ethylene glycol and 0.34 g of zinc acetate, and the mixture is heated to 200° C. for 2 h. Then, 0.29 g of trisodium phosphate anhydrate and 0.14 g of antimony(III) oxide are added, followed by heating to 280° C. and subsequent evacuation. The melt obtained (351 g, phosphorus content 0.9%) is used to injection mold test specimens 1.6 mm in thickness for measurement of the limiting oxygen index (LOI) to ISO 4589-2 and also for the UL 94 (Underwriter Laboratories) flammability test. The test specimens thus produced gave an LOI of 40% O2 and were UL 94 classified as flammability class V-0. Corresponding test specimens without 2-hydroxyethyl ethyl(3-hydroxypropyl)phosphinate gave an LOI of just 31% O2 and were UL 94 classified as flammability class V-2 only. The polyester molded article containing 2-hydroxyethyl ethyl(3-hydroxypropyl)phosphinate hence clearly has flame-retardant properties.

Workup

temperatureby heating to 280° C.

Sources & evidence

ORD record: ord-6299641d596f4e0ba81c3a1f4a6139e3
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08614267B2

Reaction notes

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