### Cover Letter

Cover Letter The phone number for Earl Goad, Senior Staff Scientist with toXcel, LLC who is serving as the Technical Contact for this PMN submission, is provided here as 703-754-0248 extension 117 since there is no space to enter his extension number in Section A Submitter page of the form. For the purpose of identification of the new substance to be listed 9-Octadecen-1-amine, hydrochloride (1:1), (9Z)- CAS No.:41130-29-4 will be also referred to using its common name of Oleylamine HCL and its precursor by the common name Olelyamine.
Overview: Production, Function and Use of the New Chemical The new compound, 9-Octodecen-1-amine, hydrochloride (1:1), (9Z) is produced by the acidification of a dilute aqueous solution/suspension of its precursor 9-Octadecen-1-amine, (9Z) with hydrochloric acid. This new chemical serves as a cationic surfactant/emulsifying agent in formulations of asphalt. Hot asphalt and the water solution containing the PMN chemical are piped in a closed system into a colloidal mill which breaks up the asphalt into fine globules/ particles while incorporating the surfactant resulting in a stable aqueous asphalt. This asphalt emulsion is used in the paving industry for “chip sealing” and other techniques for road maintenance. The structure of the new chemical is integral both in the forming as well as maintaining the stability asphalt emulsion. The alkyl hydrophobic portion of the new chemical incorporates into the substance of colloidal asphalt particles while the cationic hydrophilic portion stabilizes the suspended asphalt particles from coalescing or “breaking” from the aqueous phase. The asphalt emulsion is stabilized to the extent that it may be stored at typical ambient temperatures for a few days before use. As the emulsion is applied to road surfaces to coat and bind aggregate, a rise in pH as well evaporation of the water, initiate the “breaking” of the emulsion, coalescence of asphalt particles and adhesion of the asphalt onto the surfaces of the aggregate. The neutralization of the acid in the emulsion by the aggregate causes a reversion of the PMN chemical to the original neutral precursor oleylamine, which remains embedded in the deposited asphalt.

Properties of New Chemical: Test Substance, Fate, Health and Environmental Effects, Physical and Chemical Properties.

1) The production of the new chemical is solely by the conversion of the neutral amine form of the precursor molecule to its acid (protonated) form using hydrochloric acid. All material resulting from the production of the Oleyamine HCL is incorporated directly (dispersed) into the asphalt substances in the final asphalt emulsion. No

Page 1 NON-CBI SUBMISSIONmaterials are wasted, disposed of or released in the production of the new chemical.

2) The new chemical is formed in a dilute aqueous solution and is remains in its free form from the point of acidification until it is incorporated into the asphalt emulsion. 3) During the production of the Oleylamine HCL salt it is not isolated by purification.once produced it is incorporated into the asphalt. 4) In an aqueous solution, Oleylamine and its acid salt Oleylamine HCL will exist in a pH dependent equilibrium. Under acidic conditions the amine will be in a cationic form while at neutral to basic conditions the neutral amine will be predominant. 5) For these reasons, data on the precursor oleylamine are provided to support the listing of the Oleyamine HCL. Environmental fate, human health, and aquatic toxicity for the new chemical, the precursor amine has been used. Documents are attached to support the rationales summarized here taking into account structure activity relationships (SAR), read across, EPA screening level assessments, results of studies performed on the amine and estimation of properties and effects based on EPI Suite ver 4.11 computational modeling.

Page 2 NON-CBI SUBMISSIONTracking IDs: Pay. gov 25M1CPNE; Agency 74827855859 PMNX150805743135732
TS01TX

X X X X X

X

Page 3 NON-CBI SUBMISSIONX

Page 4 NON-CBI SUBMISSIONTodd Weist President Tri-State Asphalt, LLC PO Box 470, 1362 Bungalow Road Morris IL 60450 tweist@tsasphalt.com

Earl Goad Senior Staff Scientist toXcel LLC 7140 Heritage Village Plaza Gainesville VA 20155 Earl.Goad@toxcel.com 703-754-0248



### X X

X

X

Page 5 NON-CBI SUBMISSION

### X

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

41130-29-4


### X 393903 1 IES 393903_20150625+ Request.pdf C18H38ClN (mol.wgt 303.954)

See Attachment 002 (2 Structure Oleylamine hydrochloride.rtf)

2 Structure Oleylamine hydrochloride.rtf

Page 6 NON-CBI SUBMISSION9-Octadecen-1-amine, (9Z)- CASRN 112-90-3

Hydrochloric acid CASRN 7647-01-0

An aqueous mixture/suspension containing the precursor chemical is acidified with hydrochloric acid to produce the complementary amine hydrochloride.

Composition of the product mixture includes an aqueous solution of 9-Octadecen-1-amine, hydrochloride (1:1), (9Z) CASRN 41130-29-4, Hydrochloric acid CASRN 7647-01-0 and the acid salts of other amines which are listed, and inert chemicals which contribute to the physical properties of the formulation.

Page 7 NON-CBI SUBMISSIONPage 8 NON-CBI SUBMISSIONPage 9 NON-CBI SUBMISSIONOleylamine hydrochloride, Oleylamine HCl

Oleylamine hydrochloride 3 Impurities in Oleylamine hydrochloride..docx 9-Octadecen-1-amine, N-(9Z)-9-octadecen-1-yl-, (9Z), hydrochloride 5

None formed

Page 10 NON-CBI SUBMISSION752.96 911.08

Asphalt emusifier. Emulsifying agent used in the production of asphalt emulsions for "chipsealing" and other road maintenance techniques. 100 0.5 100 0 0 0

Page 11 NON-CBI SUBMISSION

### X

90.7 2.5 20 

### 1

The new chemical (Oleyamine HCL) is produced strictly for use as a surfactant in the manufacture of asphalt emulsions. It is produced by acidification of the alkyl amine (Olelyamine). The aqueous solution containing this new chemical is piped to a colloidal mill where it is mixed with asphalt forming an aqueous asphalt emulsion. The Oleyamine HCL is incorporated into the asphalt and functions as a stabilizer to keep the asphalt particles in suspension. The asphalt emulsion is used in the paving industry. Tri-State Asphalt, LLC 1362 Bungalow Road Morris IL 60450

Page 12 NON-CBI SUBMISSIONSee Attachment 004 (4 Production Process for Oleylamine HCL.docx)

4 Production Process for Oleylamine HCL.docx

Page 13 NON-CBI SUBMISSION5 Points of worker exposure.docx

See continuation page. id: <P9SA2(1)C1R1> PPE – ‘Rubber gloves, safety glasses, long sleeves and cuffs’ Aqueous solution 0.5% w/w 2 3 5

Page 14 NON-CBI SUBMISSIONP9SA2(1)C1R1 Part II, Section A, 2.(1) Worker Activity, Row 1

See atachment for site diagram and further details. During the acidification of the precursor substance in the "batch soap tank" QC samples are periodically taken from the tank via a side valve. The sampes are analyzed for pH and properties of the reaction mixture. Once the the samples have equilibrated to the required pH value, the reaction is considered to be complete. The product mixture containing the PMN chemical may be held in the batch mixing tank for several days. As the emulsifier solution is needed to produce the asphalt emulsion it is pumped via closed piping to the colloidal mill to be combined with the asphalt feed stock.

Page 15 NON-CBI SUBMISSION5 Points of worker exposure.docx 

### X None expected, oleylamine HCL is dispersed into asphalt 1 0 NA Other: Dispersed into asphalt emulsion See continuation page. id: <P9ASA3(5a)C1R1> O

Page 16 NON-CBI SUBMISSIONP9ASA3(5a)C1R1 Part II, Section A, B.(5a) Control Technology & Efficiency, Row 1

The new chemical Olelyamine hydrochloride is produced in the mixing tank (batch soap tank) and pumped into a colloidal mill where it acts as an emulsifier to aid in the homogenization, dispersion, and stabilization of the resulting aqueous asphalt emulsion.

Page 17 NON-CBI SUBMISSIONSee Attachment 006 (6 Use of Aqueous Asphalt Emulsion Sites Controlled by Others.docx)

6 Use of Aqueous Asphalt Emulsion Sites Controlled by Others.docx The use sites of the asphalt emulsion (containing the PMN substance) are under the control of commercial paving companies. The material is used in a standard paving process called "chipsealing".

Page 18 NON-CBI SUBMISSIONP10SB1(a)(4)1 Part II, Section B, 1(a)(4). Operation Site Locations

Use sites are inumerable. Use sites for the asphalt emulsion produced by the submitter are controlled those conducting paving operations. At the point of use the new PMN chemical has been integrated within the asphalt substance. The low pH of the emulsion stabilizes the aqueous asphalt suspension due to repulsive forces of the acidified amines imbedded in the asphalt particles. Due to their hydrophobicity the amines remain in the asphalt. Upon neutralization and evaporation of water from the emulsion the asphalt suspension breaks, resulting in the deposition of the asphalt in and on the pavement.

Page 19 NON-CBI SUBMISSIONSee continuation page. id: <P10ASB2(6)C1R1>

Not applicable, the new chemical is not available alone, it is dispersed in the asphalt substances used at sites controled by others in the paving industry

Page 20 NON-CBI SUBMISSIONP10ASB2(6)C1R1 Part II, Section B, 2.(6) Protective Equip./Eng. Controls, etc., Row 1

Workers are not exposed to the new chemical (Oleyamine HCL) because it is incorporated into the asphalt substance. Controls and protective equipment will follow typical precautions necessary for application of storage, handling, and application of asphalt emulsion at paving sites. There will be countless paving sites using the asphalt substance, all not controlled by others.

Page 21 NON-CBI SUBMISSION1) The oleylamine precursor for the production of the oleylamine hydrochloride emulsifier is a liquid (melting point ~12 C) and avoids both the

hazards of handling hot molten amines associated with solid or pasty precursor amines, such as tallowamines, which it replaces. The oleylamine precursor is easier and quicker to dissolve which streamlines the emulsion production process. 2) Techniques using asphalt emulsions allow road construction and maintenance to be carried out at lower temperatures avoiding the exposure of workers to burn hazards and fumes from hot asphalt cement, and avoiding the environmental problems associated with cut-back (solvents containing) asphalt. The use of low temperature processes using emulsion also reduced carbon emissions associated with energy use in hot processes. Emulsifying agents such as oleylamine hydrochloride allow the formulation of effective asphalt emulsion products. 3) The product is an efficient emulsifier at low use levels.

Page 22 NON-CBI SUBMISSION001 CAS - IES 393903 + Service Request 1 IES 393903_20150625+ Request.pdf Pt.I, Sec.B, 1c. 4

002 Structure of Oleylamine HCL 2 Structure Oleylamine hydrochloride.rtf Pt.I, Sec.B, 1e. 1

003 Impurities in Oleylamine HCL Production 3 Impurities in Oleylamine hydrochloride..docx Pt.I, Sec.B, 3. 1

004 Production Process for Oleyamine HCL 4 Production Process for Oleylamine HCL.docx Pt.2, Sec.A, 1d. 3

005 Worker Exposure - Submitter Production Site 5 Points of worker exposure.docx Pt.2, Sec.A, End 3

006 Use of Aqueous Asphalt Emulsion - by others 6 Use of Aqueous Asphalt Emulsion Sites Controlled by Pt.2, Sec.B, 1a. 1

007 EPI Suite v 4.11 for Oleylamine HCL 7 EPA SUITE oleylamine hydrochloride 20150623 egg.doc 13

008 EPA Suite v 4.11 for Oleylamine 8 -EPISUITE oleylamine 20150702.doc 13

009 SAR based read across for amine salts 9 SAR Read-Across Justification_pFAoAc_Final 7

010 Biodegredation Study Oleyamine - surrogate for Oleylamine HCL 10 Study Biodegradation of Armeen OD - Oleylamine.pdf 15

011 Environmental Fate Aquatic Toxicity of Oleylamine 11 Envir Fate Aquatic Toxicity Oleylamine.docx 3

012 Toxicity Oleylamine - Armeen OL 12 Oleylamine -Armeen O OL 6
013 Screening Level Assessment - FND Amines Sept 2010 13 Screening Level HazardCharacterization_FND See continuation page. id: <P12013> 76

014 Support for Bridging Physical Chem Properties 14 Support for Physical and Chemical Properties of 1

016 SDS for Armeen OL 90 - 100 % Oleylamine 16 Armeen OL 13

Page 23 NON-CBI SUBMISSIONP12013 List of Attachments, Associated PMN Section No., ID: 013

Worksheet: Physical State | Worksheet: Vapor Pressure | Worksheet: Solubility In Water | Worksheet: Melting temp | Worksheet: Boiling / sublimation temp | Worksheet: Dissociation Constant | Worksheet: Octanol / water partition coefficient | Worksheet: Henrys Law Const

Page 24 NON-CBI SUBMISSION013 

### X Measured

013 

### X 3.0 E-4 mm HG Estimate

013 

### X 0.00008 Estimate

013 

### X 21 Measured

013 

### X 335 Measured



### X 013 10.4 Estimate 

### X 013 7.5 Estimate 

### X 013 8.2 8.2 E-4 cu m / mol Estimate

Page 25 NON-CBI SUBMISSION

### ATTACHMENT HEADER SHEET

Attachment Number 001
Attachment Name CAS - IES 393903 + Service Request


### Associated PMN Section Number

Pt.I, Sec.B, 1c.

Does not contain CBI 

### Report Number PMNX150805743135732

### ATTACHMENT HEADER SHEET

Attachment Number 002
Attachment Name Structure of Oleylamine HCL


### Associated PMN Section Number

Pt.I, Sec.B, 1e.

Does not contain CBI 

### Report Number PMNX150805743135732

### ATTACHMENT HEADER SHEET

Attachment Number 003
Attachment Name Impurities in Oleylamine HCL Production


### Associated PMN Section Number

Pt.I, Sec.B, 3.

Does not contain CBI 

### Report Number PMNX150805743135732

### ATTACHMENT HEADER SHEET

Attachment Number 004
Attachment Name Production Process for Oleyamine HCL


### Associated PMN Section Number

Pt.2, Sec.A, 1d.

Does not contain CBI 

### Report Number PMNX150805743135732

### ATTACHMENT HEADER SHEET

Attachment Number 005
Attachment Name Worker Exposure - Submitter Production Site


### Associated PMN Section Number

Pt.2, Sec.A, End

Does not contain CBI 

### Report Number PMNX150805743135732

### ATTACHMENT HEADER SHEET

Attachment Number 006
Attachment Name Use of Aqueous Asphalt Emulsion - by others


### Associated PMN Section Number

Pt.2, Sec.B, 1a.

Does not contain CBI 

### Report Number PMNX150805743135732

### ATTACHMENT HEADER SHEET

Attachment Number 007
Attachment Name EPI Suite v 4.11 for Oleylamine HCL


### Associated PMN Section Number

N/A

Does not contain CBI 

### Report Number PMNX150805743135732

### ATTACHMENT HEADER SHEET

Attachment Number 008
Attachment Name EPA Suite v 4.11 for Oleylamine


### Associated PMN Section Number

N/A

Does not contain CBI 

### Report Number PMNX150805743135732

### ATTACHMENT HEADER SHEET

Attachment Number 009
Attachment Name SAR based read across for amine salts


### Associated PMN Section Number

N/A

Does not contain CBI 

### Report Number PMNX150805743135732

### ATTACHMENT HEADER SHEET

Attachment Number 010
Attachment Name Biodegredation Study Oleyamine - surrogate for Oleylamine HCL



### Associated PMN Section Number

N/A

Does not contain CBI 

### Report Number PMNX150805743135732

### ATTACHMENT HEADER SHEET

Attachment Number 011
Attachment Name Environmental Fate Aquatic Toxicity of Oleylamine


### Associated PMN Section Number

N/A

Does not contain CBI 

### Report Number PMNX150805743135732

### ATTACHMENT HEADER SHEET

Attachment Number 012
Attachment Name Toxicity Oleylamine - Armeen OL


### Associated PMN Section Number

N/A

Does not contain CBI 

### Report Number PMNX150805743135732

### ATTACHMENT HEADER SHEET

Attachment Number 013
Attachment Name Screening Level Assessment - FND Amines Sept 2010


### Associated PMN Section Number Worksheet: Physical State | Worksheet: Vapor Pressure | Worksheet: Solubility In Water | Worksheet: Melting temp | Worksheet: Boiling / sublimation temp | Worksheet: Dissociation Constant | Worksheet: Octanol / water partition coefficient | Worksheet: Henrys Law Const

Does not contain CBI 

### Report Number PMNX150805743135732

### ATTACHMENT HEADER SHEET

Attachment Number 014
Attachment Name Support for Bridging Physical Chem Properties


### Associated PMN Section Number

N/A

Does not contain CBI 

### Report Number PMNX150805743135732

### ATTACHMENT HEADER SHEET

Attachment Number 016
Attachment Name SDS for Armeen OL 90 - 100 % Oleylamine


### Associated PMN Section Number

N/A

Does not contain CBI 

### Report Number PMNX150805743135732