Production Process

9-Octadecen-1-amine,hydrochloride (1:1), (9Z)-

CAS No.:41130-29-4

(aka Oleylamine HCL)

The production process for this chemical involves the acidification of an aqueous solution of the 

precursor Oleylamine with hydrochloric acid to product the complementary hydrochloride salt. 

Other amines supplied in starting formulation are likewise converted each to their corresponding 

hydrochloride salt. The resulting mixture functions as an emulsifier used in the processing of 

asphalt materials and bituminous materials to produce stable aqueous emulations. The 

resulting asphalt emulsion is primarily used in road construction and paving.

Note: The material labeled as the emulsifier above the soap tank should be labeled emulsifier 

precursors.

1. The source product containing Oleylamine CASRN 112-90 and other amines are added to 

the mixing or “batch soap” tank with other non-reacting additives, are dispersed or dissolved 

in water (20-60 °C) at 0.05-0.50 w/w, then acidified with hydrochloric acid at 0-5 w/w until 

the target pH between pH 2 – 4 is reached. The resulting solution of emulsifier may be used 

immediately or be retained in the soap tank and used as needed within 2 days of production. 

Depending on the recipe used, each batch of approximately 6000 gallons (50,000 Ibs) of the 

finished emulsifier solution contains 25-125Ibs (10-50 kg) of alkyl amine hydrochlorides. 

Additionally, acidification also serves to solubilize the starting alkyl amine mixture, which are 

sparingly water soluble at neutral pH, as well as convert the amines to their chloride salt 

giving them their emulsification properties, and to stabilize that solution. The stability and 

properties of the final asphalt emulsion is dependent upon the complete acidification and 

dissolution of the starting mixture of amines.
2. An asphalt mixture is prepared in a separate mixing tank where the asphalt may optionally 

be mixed with latex rubber and or other additives. The mixture is heated.

3. The final asphalt emulsion is produced by piping the heated asphalt mixture (step #2) and 

the emulsifier (step#1) through a colloidal mill at a ratio of two parts asphalt to one part 

emulsifier. As the asphalt enters the mill it is mechanically broken down into fine particles 

which interact with cationic surfactants from the emulsifier mix. The solution of amine salts 

(step #1), when mixed with the milled asphalt, integrate with the substance of the asphalt 

particles to stabilize the asphalt particles to form a homogeneous aqueous emulsion. The 

20,000 gallon batch of the resulting emulsion is cooled and sent to a storage tank. The final 

emulsion contains about 0.02-0.20 % w/w of the new substance incorporated into the 

substance of the dispersed asphalt particles.

4. There is no washing or cleaning between batches, even if different emulsion recipes as 

produced, so there is no washout or waste other waste materials produced. A maximum of 

3 batches could be made within an 8 hour workday. All of the new substance produced

ends up being incorporated in the asphalt of the final aqueous emulsion.

Worker Exposure is described in greater detail attachment on Worker Exposure 

5. 2-3 workers are involved in the manufacture.

a. One to make the emulsifier (soap solution), controls the addition of the starting 

materials (amines, hydrochloric acid, additives) into the batch soap mix tank. This 

or another worker draws a small sample of the mixture from a valve on the side 

of the mix tank for analyses of the pH of the mixture.

As needed the final emulsifier solution containing the PMN chemical (Oleylamine 

HCL) is piped by a closed system to the colloidal mill.

b. Another operates the controls and monitors the colloidal milling process. 

c. Another worker takes approximately 1 gallon samples of the completed emulsion 

for quality control analyses performed in the laboratory. 

All wear a long-sleeved shirts, gloves and safety glasses. 

6. The final asphalt emulsion may be stored for hours or typically up to 5 days before shipment 

to user.

7. The final emulsion is pumped into tank trucks for shipment. Shipment size is typically 5600 

gallons (47,000Ibs) emulsion (ca. 10-1001bs (5-50kg) of new substance). Loading is 

performed by one man. He wears a long sleeved shirt, gloves and safety glasses. 

Items 8, 9, 10 describe the use of the asphalt emulsion at paving site which are controlled by companies other 

than Tri-State.
8. The end user of the emulsion is a road maintenance contractor, who may operate mobile 

emulsion tanks of up to 22,000 gallons capacity close to the road construction site. The 

emulsion is transferred by pump from these tanks to the paving equipment (asphalt 

distributor), or sometimes into intermediate delivery vehicles. 

9. The most common process of road maintenance, "chipseal", involves spraying emulsion at a 

rate of approximately 1-2 liters/sq m on the road, covering with aggregate and compacting. 

With the application of the aqueous emulsion, the water is either absorbed into the substrate 

and or evaporates. During this process the pH rises, the Oleylamine hydrochloride is 

neutralized, the amine salt converts back to a neutral amine which remains in the asphalt

but no longer possesses the repulsive charge that kept the asphalt particles from 

congealing/coalescing. As the emulsion breaks (separates) the asphalt substance is 

deposited on and in between the aggregate materials present or added during the chip 

sealing process. The amine remains incorporated in the asphalt substance in or on the 

surface of the road. Typically the chip sealed pavement is rolled to force the asphalt down 

into the aggregate to bind it together and to force the upper most aggregate to flatten out on 

the road surface. The asphalt suspension can also be used by itself to fill in small cracks in 

existing roads. 

10. In this use the PMN chemical is neutralized back to the starting amine precursor on 

exposure to environmental pH. Both pH changes and water evaporation on application to 

the paving surfaces causes the new chemical to lose its emulsifier properties resulting in the 

separation (breaking) of the asphalt suspension. Under such conditions the new chemical is

eventually converted back to the original amine which remains in the asphalt substance.