### Production Process **9 -** **Octadecen -**  **1 -** **amine,hy drochloride (1:1), (9Z)**  **-**

**CAS No.:41130 -** **29 -** **4 (aka Oley** **lamine HCL)** The production process for this chemical involves the acidification of an aqueous solution of the precursor Oley l amine wit h 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 proc essing 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 labe l ed emulsifier precursors. 1. The source product containing Oley l amine CASRN 112
- 90 and other amines are added to the mixing or “ batch soap ” tank wit h 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 re cipe 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 th e 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 p roperties, 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 aspha lt 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 par ticles wh ich 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. The re is no washing or cleaning between batches, even if different emulsion recipes as produced, so there is no wash out 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. Wo rker Exposure is described in greater detail attachment on Wo rker Exposure 5. 2 - 3 workers are involved in the manufacture

.

a. O ne 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 smal l 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 , 1 0 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 gallon s 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, "chipsea l", 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/coal escing. As the emulsion breaks (separates) the asphalt substance is deposited on and in between the aggregate materials present or added during the ch i p 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 smal l cracks in existing roads.
10. In this use t he 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 am ine which remains in the asphalt substance.