INITIAL REVIEW ENGINEERING REPORT PMN: 13-0931 Post-Focus Draft Revision 2 1 / 16 / 2014 PV (kg / yr): 10,000 ENGINEER: Macek \AH \REC Revision Notes / Assessment Overview: Revision #2 (1/16/14): Submitter indicated that the physical state of the PMN material as neat material and as processed and used is as a liquid (See contact report of 1/15/14 and MSDS). Therefore, CEB's models for estimating losses associated with transfer of solids are no longer applicable. Since the PMN chemical is a liquid with a v.p. of 0.001 torr, CEB ran applicable models to estimate air releases and vapor inhalation exposure. In amendment as well as in the 1/15/14 telecon the submitter indicated that there are no water releases from the site. | | | | Revision #1(1/8/2014: Submitter provided additional information on the production volume, category of use, mass balance and procedure, and MSDS within an Amendment submitted on 12/12/2013. Per Amendment, PV increased from 5,000 kg PMN/yr to 10,000 kg PMN/yr. Category of use changed to site limited endcapping agent for novel reactive polymers. Manufacturing releases for filter media disposal and stripping wastes to incineration have been added per the Amended Exposure and Release Data provided. MSDS information updated within the current assessment.

SUBMITTER: Henkel Corporation USE: Revision 1/8/2014: Site limited endcapping agent for novel reactive polymers. /// Polymerizable component (monomer) in adhesive formulations. Analog L-05- 4 30 is used as a monomer for adhesives for DVDs. Analog L-98-117 is used as a component of adhesives for plastic. OTHER USES: CA 151:537063, 131:291346, 130:200949

- Ophthalmic device material with high refractive index. CA 149:62770 - Production of polymeric ocular drug delivery devices. CA 131:291344 - Component of intraocular lens coating composition. CA 105:99271 - Reactive diluent for photocurable coatings for optical fibers. Analog P-01-579 is used as a component of radiation cured coatings. Analog P-01-420 is used as a monomer. Analogs P-08-161 and P-07- 5 99 are used as monomers for optical film resins.MSDS: Yes L abel: No Gen Eqpt: Safety goggles or safety glasses with side shields. // Chemical resistant, impermeable gloves. Respirator: A NIOSH-approved air

- purifying respirator with an organic vapor cartridge or canister may be permissible under certain circumstances where airborne concentrations are expected to exceed exposure limits. Protection provided by air-purifying respirators is limited. Use a positive-pressure, air- s upplied respirator if there is any potential for uncontrolled release, exposure levels are not known or any other circumstances where air-purifying respirators may not provide adequate protection. Health Effects: Inhalation: May cause respiratory tract irritation. // Skin contact: Irritating to skin. // Eye contact: Moderate eye irritation. // Ingestion: Not expected under normal conditions of use. // Existing conditions aggravated by exposure: Eye, skin, and respiratory disorders. TLV / PEL: None established. CRSS (10 / 21 / 2013): Chemical Name: 2-Propenoic acid, 4-phenoxybutyl ester S-H20: 0.0394 g / L @ Physical State and Misc CRSS Info: MW: 220.00 %<500 %<1000 VP: 1.0E-3 torr @ Neat: Solid Mfg: Solid Proc/Form: Solution (Est.): 10% PMN material in adhesive End Use: Destroyed. Submitted Properties: None. The GC- M S and 1H-NMR spectra are included with the PMN submission. The 1H-NMR spectrum is consistent with the structure submitted. Estimated Properties: BP = 300 °C (EPI), 324 ° C(ACD); VP = 0.00101 torr (EPI), 0.00024 torr (ACD); WS = 0.0394 g/L (EPI), 0.24 g/L (ACD); logP = 3.44 (EPI), 3.33 (ACD). Consumer Use: No SAT (concerns) (10 / 22 / 2013): Analogs:
. Related Cases and Misc SAT Info: Migration to groundwater: Negligible PBT rating: P1B1T1 Health: 1-2 Dermal, Drinking Water, Inhalation Eco: 3 Water (All releases to water with a CC = 1 ppb)INITIAL REVIEW ENGINEERING REPORT PMN: 13-0931 Manufacturing Henkel Salisbury Salisbury NC 28147 Number of Sites / Location: 1
Days / yr: 100 Basis: Revision 1/8/2014: Submitter increased PV from 5,000 kg PMN/yr to 10,000 kg PMN/yr. CEB assumes 1 site, 100 kg/bt, and 100% PMN in product; CS calculates 100 batches/site- yr. /// Per submission: 1 site, 100 kg/bt, 15 hr/bt, and 50 bt/yr. Process Description: Raw materials (liquid)

- - > reactor 1 -- > filtration --> phase separation --> liquid extraction --> vacuum -- > PMN product (liquid, 100%) stored on- s ite (submitter stated in 1/15/14 telecon and also indicated in phone log that the PMN material is a liquid). ENVIRONMENTAL RELEASES ESTIMATE SUMMARY IRER Note: The daily releases listed for any source below may coincide with daily releases from the other sources to the same medium. Revisi on 1/8/2013: Per 12/12/2014 Amendment (Exposure and Release Data), no water releases are expected. /// Note the PMN is slightly volatile; therefore, fugutive losses are assessed using std. CEB models.Air Typical: 6.0E-7 kg / site-day over 100 days / yr from 1 site or 6.0E-5 kg/site-yr from 1 site or 6.0E

- 5 kg/yr

- a ll sites Worst Case: 1.2E-6 kg / site

- day over 100 days / yr from 1 site or 1.2E-4 kg/site-yr from 1 site or 1.2E-4 kg/yr-all sites to: from: Loading Liquid Product into Drums basis: EPA/OAQPS AP-42 Loading Model. Air Output 2: 1.5E-4 kg / site- day over 100 days / yr from 1 site or 1.5E-2 kg/site-yr from 1 site or 1.5E-2 kg/yr-all sites to: from: Equipment Cleaning Losses of Liquids from a Single, Large Vessel basis: EPA/OPPT Mass Transfer Coefficient Model. Incineration Output 2: 1.0E-1 kg / site- day over 100 days / yr from 1 site or 1.0E+1 kg/site-yr from 1 site or 1.0E+1 kg/yr-all sites to: Incineration (per amendment 12/12/2013) from: Filter Media Changeout basis: User-Defined Loss Rate Model. Per 12/12/2013 Amendment (Exposure and Release Data), submitter estimates a release on 0.1 kg/bt to incineration from filter wastes.
Incineration Output 2: 1.0E-1 kg / site- day over 100 days / yr from 1 site or 1.0E+1 kg/site-yr from 1 site or 1.0E+1 kg/yr

- a ll sites to: Incineration (per amendment 12/12/2013) from: Stripping Wastes basis: User-Defined Loss Rate Model. Per 12/12/2013 Amendment (Exposure and Release Data), submitter estimates 0.1 kg/bt released to incineration from stripping wastes.
Incineration Conservative: 1.0E+0 kg / site

- day over 100 days / yr from 1 site or 1.0E+2 kg/site-yr from 1 site or 1.0E+2 kg/yr-all sites to: Incineration from: Equipment Cleaning Losses of Liquids from a Single, Large Vessel basis: EPA/OPPT Single Vessel Residual Model, CEB standard 1% residual. Submission estimates 0.1 kg/bt (0.1% loss) sent to off- s ite incineration as hazardous waste. CEB default of 1% loss is assessed as conservative.

RELEASE TOTAL1.2E+2 kg / yr - all sites

OCCUPATIONAL EXPOSURES ESTIMATE SUMMARY Tot. #of workers exposed via assessed routes: 4 Basis:Inhalation: Exposure to Vapor (volatile) (Class II) Typical: > Potential Dose Rate: 2.9E

- 4mg / day over 100 days / yr > Lifetime Average Daily Dose: 6.4E

- 7 mg / kg

- day over 100 days / yr > Average Daily Dose: 1.1E

- 6 mg / day over 100 days / yr > Acute Potential Dose: 4.1E

- 6 mg / day over 100 days / yr Worst Case: > Potential Dose Rate: 1.7E

- 2 mg / day over 1 00 days / yr > Lifetime Average Daily Dose: 3.8E

- 5 mg / kg

- day over 100 days / yr > Average Daily Dose: 6.7E

- 5 mg / day over 100 days / yr > Acute Potential Dose: 2.5E

- 4mg / day over 100 days / yr Number of workers (all sites) with inhalation exposure: 4 Basis: Loading Liquid Product into Drums; EPA / OPPT Mass Balance Model. NOTE: The respirator class is: II. Gas/vapor (all substances in the gas form). INHALATION MONITORING DATA REVIEW 1) Uncertainty (estimate based on model, regulatory limit, or data not specific to industry): Yes 2)a) Exposure level > 1 mg / day? No OR b) Hazard Rating for health of 2 or greater? 1

- 2 No => Inhalation Monitoring Data Desired? **No** Exposure to Vapor (volatile) (Class II) Typical: > Potential Dose Rate: 9.2E

- 4mg / day over 100 days / yr > Lifetime Average Daily Dose: 2.1E

- 6 mg / kg

- day over 100 days / yr > Average Daily Dose: 3.6E

- 6 mg / day over 100 days / yr > Acute Potential Dose: 1.3E

- 5 mg / day over 100 days / yr Worst Case: > Potential Dose Rate: 8.3E

- 3 mg / day over 100 days / yr > Lifetime Average Daily Dose: 1.9E

- 5 mg / kg

- day over 100 days / yr > Average Daily Dose: 3.3E

- 5 mg / day over 100 days / yr > Acute Potential Dose: 1.2E

- 4mg / day over 100 days / yr Number of workers (all sites ) with inhalation exposure: 4 Basis: Equipment Cleaning Losses of Liquids from a Single, Large Vessel; EPA/OPPT Mass Balance Model. NOTE: The respirator class is: II. Gas/vapor (all substances in the gas form). INHALATION MONITORING DATA REVIEW 1) Uncertainty (estimate based on model, regulatory limit, or data not specific to industry): Yes 2)a) Exposure level > 1 mg / day? No ORb) Hazard Rating for health of 2 or greater? 1

- 2 No => Inhalation Monitoring Data Desired? **No** Dermal: Exposure to Liquid at 100.00% concentration High End: > Potential Dose Rate: 2.2E+3 mg / day over 100 days / yr > Lifetime Average Daily Dose: 5.0E+0 mg / day over 100 days / yr > Average Daily Dose: 8.8E+0 mg / day over 100 days / yr > Acute Potential Dose: 3.2E+1 mg / day over 100 days / yr Number of workers (all sites) with dermal exposure: 4 Basis: Loading Liquid Product into Drums; EPA/OPPT 2

- Hand Dermal Contact with Liquids Model. Exposure to Liquid at 100.00% concentration High End: > Potential Dose Rate: 2.2E+3 mg / day over 100 days / yr > Lifetime Average Daily Dose: 5.0E+0 mg / day over 100 days / yr > Average Daily Dose: 8.8E+0 mg / day over 100 days / yr > Acute Potential Dose: 3.2E+1 mg / day over 100 days / yr Number of workers (all sites) with dermal exposure: 4 Basis: Equipment Cleaning Losses of Liquids from a Single, Large Vessel; EPA/OPPT 2-Hand Dermal Contact with Liquids Model.INITIAL REVIEW ENGINEERING REPORT PMN: 13-0931 Use: Site-limited Chemical Intermediate Henkel Salisbury Salisbury NC 28147 Number of Sites / Location: 1
Days / yr: 100 Basis: Revision 1/8/2014:Submitter increased PV from 5,000 kg PMN/yr to 10,000 kg PMN/yr. CEB assumes 100 bt/site- yr as the polymerization occurs at the mfg site. CS calculates a use rate of 100 kg PMN/st- b t. /// Per technical contact, polymerization occurs at the mfg site. CEB assumes 50 bt/site-yr. Process Description: PMN (liquid, 100%)

- - > charged into reaction vessel --> polymerized and destroyed (technical contact) ENVIRONMENTAL RELEASES ESTIMATE SUMMARY IRER Note: The daily releases listed for any source below may coincide with daily releases from the other sources to the same medium.Air Typical: 6.0E-7 kg / site-day over 100 days / yr from 1 site or 6.0E-5 kg/site-yr from 1 site or 6.0E

- 5 kg/yr

- a ll sites Worst Case: 1.2E-6 kg / site

- day over 100 days / yr from 1 site or 1.2E-4 kg/site-yr from 1 site or 1.2E-4 kg/yr-all sites to: from: Unloading Liquid Raw Material from Drums basis: EPA/OAQPS AP-42 Loading Model. Air Output 2: 2.0E-8 kg / site- day over 100 days / yr from 1 site or 2.0E-6 kg/site-yr from 1 site or 2.0E-6 kg/yr-all sites to: from: Cleaning Liquid Residuals from Drums Used to Transport the Raw Material basis: EPA/OPPT Penetration Model. Incineration High End: 6.2E+0 kg / site- day over 48 days / yr from 1 site or 3.0E+2 kg/site-yr from 1 site or 3.0E+2 kg/yr-all sites to: Incineration from: Cleaning Liquid Residuals from Drums Used to Transport the Raw Material basis: EPA/OPPT Drum Residual Model, CEB standard 3% residual. Submission indicated that all wastes are drummed and sent to off- s ite incineration as hazardous waste. In an amendment to the PMN, the submitter indicated that there are no aqueous wastes from this site.

RELEASE TOTAL 3.0E+2 kg / yr - all sites

OCCUPATIONAL EXPOSURES ESTIMATE SUMMARY Tot. # of workers exposed via assessed routes: 3 Basis:Inhalation: Exposure to Vapor (volatile) (Class II) Typical: > Potential Dose Rate: 2.9E

- 4mg / day over 100 days / yr > Lifetime Average Daily Dose: 6.4E

- 7 mg / kg - day over 100 days / yr > Average Daily Dose: 1.1E

- 6 mg / day over 100 days / yr > Acute Potential Dose: 4.1E

- 6 mg / day over 100 days / yr Worst Case: > Potential Dose Rate: 1.7E

- 2 mg / day over 100 days / yr > Lifetime Average Daily Dose: 3.8E

- 5 mg / kg

- day over 100 days / yr > Average Daily Dose: 6.7E

- 5 mg / day over 100 days / yr > Acute Potential Dose: 2.5E

- 4mg / day over 100 days / yr Number of workers (all sites) with inhalation exposure: 3 Basis: Unloading Liquid Raw Material from Drums; EPA/OPPT Mass Balance Model. NOTE: The respirator class is: II. Gas/vapor (all substances in the gas form). INHALATION MONITORING DATA REVIEW 1) Uncertainty (estimate based on model, regulatory limit, or data not specific to industry): Yes 2)a) Exposure level > 1 mg / day? No OR b) Hazard Rating for health of 2 or greater? 1

- 2 No => Inhalation Monitoring Data Desired? **No** Exposure to Vapor (volatile) (Class II) Typical: > Potential Dose Rate: 9.4E

- 6 mg / day over 100 days / yr > Lifetime Average Daily Dose: 2.1E

- 8 mg / kg

- day over 100 days / yr > Average Daily Dose: 3.7E

- 8 mg / day over 100 days / yr > Acute Potential Dose: 1.3E

- 7 mg / day over 100 days / yr Worst Case: > Potential Dose Rate: 2.8E

- 4mg / day over 100 days / yr > Lifetime Average Daily Dose: 6.3E

- 7 mg / kg

- day over 100 days / yr > Average Daily Dose: 1.1E

- 6 mg / day over 100 days / yr > Acute Potential Dose: 4.0E

- 6 mg / day over 100 days / yr Number of workers (all sites) with inhalation exposure: 3 Basis: Cleaning Liquid Residuals from Drums Used to Transport the Raw Material; EPA/OPPT Mass Balance Model. NOTE: The respirator class is: II. Gas/vapor (all substances in the gas form). INHALATION MONITORING DATA REVIEW 1) Uncertainty (estimate based on model, regulatory limit, or data not specific to industry): Yes 2)a) Exposure level > 1 mg / day? No ORb) Hazard Rating for health of 2 or greater? 1

- 2 No => Inhalation Monitoring Data Desired? **No** Dermal: Exposure to Liquid at 100.00% concentration High End: > Potential Dose Rate: 2.2E+3 mg / day over 100 days / yr > Lifetime Average Daily Dose: 5.0E+0 mg / day over 100 days / yr > Average Daily Dose: 8.8E+0 mg / day over 100 days / yr > Acute Potential Dose: 3.2E+1 mg / day over 100 days / yr Number of workers (all sites) with dermal exposure: 3 Basis: Unloading Liquid Raw Material from Drums; EPA/OPPT 2-Hand Dermal Contact with Liquids Model. Exposure to Liquid at 100.00% concentration High End: > Potential Dose Rate: 2.2E+3 mg / day over 100 days / yr > Lifetime Average Daily Dose: 5.0E+0 mg / day over 100 days / yr > Average Daily Dose: 8.8E+0 mg / day over 100 days / yr > Acute Potential Dose: 3.2E+1 mg / day over 100 days / yr Number of workers (all sites) with dermal exposure: 3 Basis: Cleaning Liquid Residuals from Drums Used to Transport the Raw Material; EPA/OPPT 2-Hand Dermal Contact with Liquids Model.CALL BY:

CALL TO: Organization: Henkel Date: 10 / 23 / 2013 Time: 1:30PM

PMN: 13-0931 Organization: ERG for CEB

Phone: Concerning what TSCA CBI? CBI: Yes MEMORANDUM of CBI TELEPHONE CONVERSATION

Q1: What is the physical form of the neat PMN? Is it a flakey solid? Fine powder? Resin? A1:It's a crystalline -- not a dusty solid. | | Q2: Please describe what happens to the PMN after it leaves MFG site. How many customers do you have? A2: After mfg, it's stored on-site then charged into another reaction vessel where it's combined with high- MW polymers and polymerized. The end- p roduct will then be sold to adhesive formulators, and is usually formualted sealan t products. By the time it leaves our site, it is no longer the same PMN substance. | | Q3: For EPA's perspective, this chemical really is an intermediate and is site-limited -- because the original PMN substance no longer exists by the time it's sold to an adhesive formulator. Is this correct? If so, please revise the PMN submission to clarify the category of use. A4: You are correct, this chemical is an intermediate. Also, I should've indicated this chemical as being site-limited. I will re-submit the PMN.CALL BY: Greg Macek

CALL TO: Organization: Henkel Date: 01 / 15 / 2014 Time: 2:30 pm

PMN: 13-0931 Organization: ERG for CEB

Phone: Concerning what TSCA CBI? CBI: Yes MEMORANDUM of CBI TELEPHONE CONVERSATION

The submitter technical contact was asked about the potential for releases during transfer of solid material. In response, the technical contact stated that the PMN chemical is a liquid as also indicated in the MSDS.| | The submitter also stated that ther eare no water releases from this facility.| |