New type of trifunctional alcohol was synthesized from commercially available trimer acid. Trifunctional alcohol is hydrocarbon with widely separated terminal hydroxyl groups, and was expressly developed as crosslinking agent for preparation of polyurethane propellants, binders and case liners

Hutchison, J. J.

Marsh, H. E., Jr.

English

NASA Technical Reports Server

September 1972
	 B72-10553 
. NASA TECH BRIEF 
NASA Pasadena Office
	 4V 
NASA Tech Briefs announce new technology derived from the U.S. space program. They are issued to encourage 
commercial application. Tech Briefs are available on a subscription basis from the National Technical Information 
Service, Springfield, Virginia 22151. Requests for individual copies or questions relating to the Tech Brief program may 
be directed to the Technology Utilization Office, NASA, Code KT, Washington, D.C. 20546. 
New Type of Trifunctional Alcohol 
A new type of trifunctional alcohol has been syn-
thesized from commercially available trimer acid. The 
tri.functional alcohol is a hydrocarbon with widely 
separated terminal hydroxyl groups, and it was 
expressly developed as a crosslinking agent for the 
preparation of polyurethane propellants, binders, and 
case liners; however, it may also be used as an ad-
ditive in formulations for epoxy resins, alkyd resins, 
and elastomer systems which require high thermal 
stability. 
The preferred method of synthesis involves quanti-
tative conversion of all carboxylic acid groups in 
trimer acid to form a trifunctional alcohol which is 
free of intermediate reduction products. The starting 
material for synthesis is a specially hydrogenated 
form of the trimer acid that is prepared commercially 
by trimerization of C-18 fatty acid; commercially 
available trimer acid is hydrogenated until the iodine 
number of the product is 0.4 or less. The hydrogen-
ation is performed at a temperature of about 1100 to 
140°C and a pressure of 12 to 14 MN/M2
 (1.8 to 2.0 
ksi) in a hydrocarbon solvent; the catalyst consists of 
about 5% by weight of palladium-on-charcoal. The 
hydrogenated trimer acid is then esterified over a 
period of seven days by refluxing in a solution of 
ethanol and toluene; sulfuric acid is used as catalyst. 
Water is removed continuously by separation of the 
ternary azeotrope and recycling of the toluene; at the 
conclusion of the esterification, the acid catalyst is 
removed by a sodium bicarbonate wash. The trimer 
acid triethyl ester is a nonviscous oil with a very low 
carboxyl content.
About 100 g of the timer acid triethyl ester is dis-
solved in 500 ml of anhydrous diethyl ether, and the 
resulting solution is slowly added to an agitated slurry 
of 300 g of lithium aluminum hydride in about one 
liter of anhydrous ethyl ether. Throughout the ad-
dition, the mixture is stirred by high-torque mechan-
ical stirrers. Some of the ether refiuxes immediately, 
indicating that chemical reaction is occurring; a solid 
is also formed. The resulting thick precipitate is a!-
lowed to stand overnight and then hydrolyzed by 
cautious addition of water. The hydrolysis is com-
pleted by addition of dilute sulfuric acid. Finally, the 
ether layer is separated, washed with aqueous sodium 
bicarbonate solution, and then with water. The ether 
is evaporated; there remains a liquid product which 
can be identified as a C-54 branched-chain alcohol 
with primary terminal hydroxyl groups and a func-
tionality value of 3.0. 
The molecular weight of the trifunctional alcohol is 
about 750. When used as a crosslinking agent, it can 
be readily poured, blended, and intermixed with 
typical propellant polyurethane materials prior to 
final cure. Additionally, the trifunctional alcohol is 
much more soluble in polyurethanes than are other 
commercially available lower molecular weight tn-
functional glycols and triols. 
Notes: 
1. The trifunctional alcohol can also be prepared by 
direct, copper chromite-catalyzed hydrogenation 
of trirner acid tniethylester at 250°C and 34.4 
(continued overleaf) 
This document was prepared under the sponsorship of the National
	 Government assumes any liability resulting from the use of the 
Aeronautics and Space Administration. Neither the United States
	 information contained in this document, or warrants that such use 
Government nor any person acting on behalf of the United States
	 will be free from privately owned rights.
[]
https://ntrs.nasa.gov/search.jsp?R=19720000552 2020-03-17T03:34:40+00:00Z
kN/m2 (5 ksi), but impurities such as aldehydes 
are apt to be present. 
2. Requests for further information may be directed 
to:
Technology Utilization Officer' 
NASA Pasadena Office 
4800 Oak Grove Drive 
Pasadena, California 91103 
Reference: 72-10553
Patent status: 
NASA has decided not to apply for a patent. 
Source: Harold E. Marsh, Jr. and 
John j:. Hutchison of 
Caltech/JPL 
under contract to 
NASA Pasadena Office 
(NPO-10714)
. 
B72-10553	 Category 04


New type of trifunctional alcohol

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