Professional Documents
Culture Documents
[11]
' 4,297,290
Stockburger
[45]
[75] Inventor:
[51]
[52]
[58]
Field of Search
[56]
..................... .. 260/410.6
References Cited
U.S. PATENT DOCUMENTS
2,322,820
2,322,821
6/ 1943
6/1943
2,387,842
6/1943 Soltzberg .
260/4106
260/4106
OTHER PUBLICATIONS
Brandner, J. D. et al., Industrial and Engineering Chem
[57]
ABSTRACI
8 Claims, No Drawings
4,297,290
?rst in the presence of a basic catalyst at 200260 C., 40 which do not meet established speci?cations for sorbi
then in the presence of an acid catalyst at 180240 C.
tan fatty acid ester surfactants.
'
4,297,290
ordinarily required.
ature is reached and maintaining this temperature for a 40 about one mole of phosphoric acid for every 1.5 moles
used.
'
Sorbitan
Mono-
Sorbitan
Mono-
Sorbitan
Mono
laurate
stearate
oleate
Acid No.
4-7
5-10
5.5-8
Hydroxyl No.
Saponi?cation No.
330-358
158-170
235-260
145-157
149-160
193-209
4,297,290
Unbleached
4.3
Hydroxyl No.
Saponi?cation No.
Color, (Gardner):
Bleached
334
165
Initial
1+
24 hour
1+
48 hour
72 hour
5
5
96 hour
2
4+
4+
EXAMPLE 2
thermocouple, agitator, and a condenser and receiver 30 with Part A, 499 g. commercial lauric acid (approxi
the water was removed, 7.2 g. of p-toluenesulfonic acid 35 except as indicated. The product was neutralized with
phosphoric acid and ?ltered through diatomaceous
was charged, the vacuum was again applied, and the
earth, bleached with 0.5% (based on product weight) of
charge heated to 120 C. The charge was maintained at
35% (by weight) aqueous hydrogen peroxide solution
this temperature and at 5 mm Hg. pressure for 110 min
and again ?ltered.
utes. The charge was then cooled, 1.6 g. of sodium
hydroxide and 3.5 g. of diatomaceous earth (Super 40 Analysis of the product after re?ltration showed the
following:
Cel) were added, and the charge was agitated for 15
Gardner color (initial): less than 1
minutes and ?ltered under a nitrogen atmosphere at
Acid No.: 4.9
about 90~ll0 C. through a sintered glass ?lter funnel.
Saponi?cation No.: 162
The product had a hydroxyl number of 1195 (corre 45
Hydroxyl No.: 345
sponding to a degree of anhydrization of about 1.3) and
Percentage of soap: 0.12
a Gardner color of 3.
EXAMPLE 3
50
A. Anhydrization
Deionized sorbitol solution (70% solids) was anhy
drized in the manner described in Example 1, Part A,
except that the anhydrization time was 70 minutes. A
product having a hydroxyl number of 1308 and a Gard
B. Esteri?cation
nitrogen, treated with 1.49 g. of 85% phosphoric acid
and 1.5 g. of diatomaceous earth, and ?ltered through a
Anhydro sorbitol (324 g.) prepared in accordance
glass funnel at 90 to 110 C. under nitrogen. A 30 gram 65 with Part A of this example, commercial stearic acid
sample was withdrawn for color stability test. The re
(720.9 g. consisting of approximately 52% by weight
mainder was reheated to 100 C. under nitrogen and
stearic acid, 43% by weight palmitic acid, remainder
other fatty acids), 2.52 g. powdered sodium hydroxide,
bleached for 20 minutes with 1.1 g. of 35% aqueous
4,297,290
following analysis:
15
Part A. Anhydrization
The procedure of Example 3, Part A (second prepa
ration) was used, giving an anhydro sorbitol having a
hydroxyl number of 1314.
20
Acid No.: 13
Part B. Esteri?cation
speci?cations.
COMPARATIVE EXAMPLE A