## Cover Letter

This is a resubmission for submission number P14-251-252 based on discussions with Kathy Schechter and Diane Darling of the EPA who suggested that reaction product names would be more appropriate for this material. Revised names and CAS numbers are provided. Additionally, during this same discussion it was suggested that this product may be used to produce anionic forms of the compound. Therefore a use catagory as an intermediate has been assigned at an estimated amount of 5%. Ethox has not collected toxicity data for the submitted compounds. Toxicity testing has been performed on a related compound, E-Sperse 100, CAS# 116998-33-5 and CAS# 59891-11-1, which is an ethoxylated distyrenated phenol, ammonium sulfate salt. We expect the submitted compounds to have similar toxicity profiles. The compounds covered in this PMN differ from E-Sperse 100 in that they have added ally functionality to promote binding to materials in which they are dispersed. Additionally E-Sperse is an ammonium sulfate salt while the compounds covered in this PMN are neutral. The following tests were performed for E-Sperse 100, with the indicated results. Acute Toxicity to Rainbow Trout. Result: No mortality and sub-lethal effects at 500 mg/L exposure after 96 hrs. 10% mortality at 1000 mg/L. EC50 > 1000 mg/L. Acute Toxicity to Water Fleas. Result: No immobilization after up to 1000 mg/L after 48 hours. 24 and 48 hr NOEC and LOEC are 1000 mg/L and > 1000 mg/L, respectively. EC50 > 1000 mg/L. 96 Hr Toxicity Test with the Freshwater Green Alga, Under Static Conditions. Result: EC50 > 1000 @ 24 Hr, EC50 > 931 @ 48 Hr, EC50 > 532 @ 72 Hr, EC50 > 253 @ 96 Hr. NOEC 100 @ 96 Hr. Official reports of this testing are available and will be provided if they are needed to support approval of this PMN.

Page 1 NON-CBI SUBMISSION

### 25DUFSQC PCX7140224370258292 GR53EM

X X

X 2 Page 2 NON-CBI SUBMISSION

### X

X X X X

Page 3 NON-CBI SUBMISSIONJohn McKiernan Research Chemist Ethox Chemicals, LLC 1801 Perimeter Road Greenville SC 29605 jmckiernan@ethox.com

John McKiernan Research Chemist Ethox Chemicals, LLC PO Box 5094 Greenville SC 29606 jmckiernan@ethox.com 864-277-1620



## X 7038 

## X X
Page 4 NON-CBI SUBMISSION

## X

Phenol, styrenated, reaction products with polyethylene glycol and 2-[(2-propen-1-yloxy)methyl]oxirane
1539128-27-2 

## X 376784-1 376784-1.pdf 

### (C8H9)x(C6H(5-x)O)(C6H10O2)y(C2H4O)zH, where x=1-3, y=1, z=5-45

RS-1616.jpg Page 5 NON-CBI SUBMISSIONstyrenated phenol, 61788-44-1

potassium hydroxide, 45%, 1310-58-3 allyl glycidyl ether (AGE), 106-92-3 ethylene oxide (EO), 75-21-8

The material is manufactured in a two step process. 1) Styrenated phenol is reacted with allyl glycidyl ether in a base catalyzed nucleophilic substitution. 2) The product of step 1 is ethoxylated by addition of ethylene oxide.

1 equivalent styrenated phenol 1 equivalent allyl glycidyl ether 5-45 equivalents ethylene oxide

Page 6 NON-CBI SUBMISSION

## X

1093 0.69 16.98 RS-1616 GPC.pdf



### styrenated phenol 61788-44-1 27.83 2 

### potassium hydroxide, 45% 1310-58-3 0.34 2 

### allyl glycidyl ether (AGE) 106-92-3 9.93 2 

### ethylene oxide (EO) 75-21-8 61.91 2

Page 7 NON-CBI SUBMISSION

## X 376784-1 376784-1.pdf 

### Phenol, styrenated, reaction products with polyethylene glycol and 2-[(2-propen-1-yloxy)methyl]oxirane

1539128-27-2

RS-1616.jpg Page 8 NON-CBI SUBMISSIONDSP AGE POE

E-Sperse RS-1616
Styrenated phenol allyl glycidyl ether ethoxylate 1,4-dioxane 123-91-1 0.01

water 7732-18-5 ethylene glycol 107-21-1
Page 9 NON-CBI SUBMISSION

## X

Phenol, styrenated, reaction products with polyethylene glycol and 2-[(2-propen-1-yloxy)methyl]oxirane
1539128-27-2 

## X 376784-1 376784-1.pdf 

### (C8H9)x(C6H(5-x)O)(C6H10O2)y(C2H4O)zH, where x=1-3, y=2, z=5-45

RS-1617.jpg Page 10 NON-CBI SUBMISSIONstyrenated phenol, 61788-44-1

potassium hydroxide, 45%, 1310-58-3 allyl glycidyl ether (AGE), 106-92-3 ethylene oxide (EO), 75-21-8

1) Styrenated phenol is reacted with allyl glycidyl ether in a base catalyzed nucleophilic substitution. 2) The product of step 1 is ethoxylated by addition of ethylene oxide.

1 equivalent styrenated phenol 2 equivalents allyl glycidyl ether 5-45 equivalents ethylene oxide

Page 11 NON-CBI SUBMISSION

## X

1064 0.22 22.88 RS-1617 GPC.pdf



### styrenated phenol 61788-44-1 26.22 2 

### potassium hydroxide, 45% 1310-58-3 0.40 2 

### allyl glycidyl ether (AGE) 106-92-3 18.70 2 

### ethylene oxide (EO) 75-21-8 54.68 2

Page 12 NON-CBI SUBMISSION

## X 376784-1 376784-1.pdf 

### Phenol, styrenated, reaction products with polyethylene glycol and 2-[(2-propen-1-yloxy)methyl]oxirane

1539128-27-2

RS-1617.jpg Page 13 NON-CBI SUBMISSIONDSP (AGE)2 POE

E-Sperse RS-1617
Styrenated phenol allyl glycidyl ether ethoxylate 1,4-dioxane 123-91-1 0.01

water 7732-18-5 ethylene glycol 107-21-1
Page 14 NON-CBI SUBMISSION

### X X
9999 9999

A reactive emulsifier for manufacturing aqueous emulsion polymers or alkyd resins. Dispersant for pigments in aqueous or solvent-based coatings. 95 100 0 0 100 0 Intermediate for production of related anionic dispersants. 5 100 100 0 0 0

Page 15 NON-CBI SUBMISSION

### X



## X
4500 72 2 

## 1

The material is manufactured in the two step process described below. Masses given are for a 4500 kg batch. 1) Styrenated phenol (1252 kg) is reacted with allyl glycidyl ether (447 kg) in a base catalyzed nucleophilic substitution (15 kg KOH 45%). 2) The product of step 1 is ethoxylated by addition of ethylene oxide (2786 kg). Excess ethylene oxide is removed via nitrogen purge and is directed into the scrubber. The ethylene oxide is 100 % converted to ethylene glycol in the scrubber. 1% of the generated ethylene glycol is lost to fugitive air. The remainder is collected in water and sent for on-site biological pretreatment prior to release to POTW. Ethox Chemicals, LLC 1801 Perimeter Road Greenville Greenville SC 29605

Page 16 NON-CBI SUBMISSIONRS-1616 & RS-1617 production scheme.jpg Page 17 NON-CBI SUBMISSION

### X

Addition of styrenated phenol to the reactor PPE: rubber gloves, sleeves, apron, steel toed shoes, hard hat, safety glasses liquid 2 1 2 Addition of potassium hydroxide to the reactor PPE: rubber gloves, sleeves, apron, steel toed shoes, hard hat, safety glasses, face shield solid 2 1 2 Addition of allyl glycidal ether to the reactor See continuation page. id: <P9SA2(3)C1R3> liquid 2 1 2 Addition of ethylene oxide to the reactor by way of the weigh tank See continuation page. id: <P9SA2(3)C1R4> liquid 2 1 2

Page 18 NON-CBI SUBMISSIONP9SA2(3)C1R3 Part II, Section A, 2.(3) Prot. Equipment, etc., Row 3

PPE: rubber gloves, sleeves, apron, steel toed shoes, hard hat, safety glasses, full face supplied air respirator

Page 19 NON-CBI SUBMISSIONP9SA2(3)C1R4 Part II, Section A, 2.(3) Prot. Equipment, etc., Row 4

Contained system transported through piping. Standard PPE: PPE: steel toed shoes, hard hat, safety glasses

Page 20 NON-CBI SUBMISSION

## X WCRSA Reedy River Plant SCR000197

1d water vapor 17.72

kg/batch Fugitive Air 2d ethylen e glycol 0.19 kg Fugitive Air 2c ethylen e glycol 19.00 POTW Biological Pretreatment 0 kg/batch

Page 21 NON-CBI SUBMISSION

### X



## X
4500 72 2 

## 1

The material is manufactured in the two step process described below. Masses given are for a 4500 kg batch. 1) Styrenated phenol (1180 kg) is reacted with allyl glycidyl ether (842 kg) in a base catalyzed nucleophilic substitution (18 kg KOH 45%). 2) The product of step 1 is ethoxylated by addition of ethylene oxide (2461 kg). Excess ethylene oxide is removed via nitrogen purge and is directed into the scrubber. The ethylene oxide is 100 % converted to ethylene glycol in the scrubber. 1% of the generated ethylene glycol is lost to fugitive air. The remainder is collected in water and sent for on-site biological pretreatment prior to release to POTW. Ethox Chemicals, LLC 1801 Perimeter Road Greenville Greenville SC 29605

Page 22 NON-CBI SUBMISSIONRS-1616 & RS-1617 production scheme.jpg Page 23 NON-CBI SUBMISSION

### X

Addition of styrenated phenol to the reactor Closed system using piping. Steel toed shoes, hard hat, safety glasses liquid 2 1 2 Addition of potassium hydroxide to the reactor Rubber gloves, sleeves, apron, steel toed shoes, hard hat, safety glasses, face shield solid 2 1 2 Addition of allyl glycidyl ether See continuation page. id: <P9SA2(3)C2R3> liquid 2 1 2 Addition of ethylene oxide to the reactor by way of the weigh tank Closed system using piping. Steel toed shoes, hard hat, safety glasses liquid 2 1 2

Page 24 NON-CBI SUBMISSIONP9SA2(3)C2R3 Part II, Section A, 2.(3) Prot. Equipment, etc., Row 3

Rubber gloves, sleeves, apron, steel toed shoes, hard hat, safety glasses, full face supplied air respirator

Page 25 NON-CBI SUBMISSION

## X WCRSA Reedy River Plant SCR000197

1d water vapor 21.15

kg/batch Fugitive Air 2d ethylen e 0.17 kg Fugitive Air 2c ethylen e glycol 16.78 kg/batch POTW Biological Pretreatment 0 kg/batch

Page 26 NON-CBI SUBMISSION

### X X

0

Page 27 NON-CBI SUBMISSIONPage 28 NON-CBI SUBMISSIONPage 29 NON-CBI SUBMISSION001 RS-1616 RS-1616.jpg Pt.I, Sec.B, 1e. | Pt.I, Sec.B, 2e. 1 002 RS-1617 Structure RS-1617.jpg Pt.I, Sec.B, 1e. (Chem 2) | Pt.I, Sec.B, 2e. (Chem 2) 1 003 RS-1616 & RS-1617 production scheme RS-1616 & RS-1617 production scheme.jpg Pt.2, Sec.A, 1d. | Pt.2, Sec.A, 1d. (#2) 1 004 376784-1 376784-1.pdf See continuation page. id: <P12004> 1 006 RS-1616 FTIR RS-1616 FTIR.pdf Worksheet: Spectra 1 007 RS-1617 FTIR RS-1617 FTIR.pdf Worksheet: Spectra (#2) 1 008 RS-1616 GPC RS-1616 GPC.pdf Pt.I, Sec.B, 2a. 1 009 RS-1617 GPC RS-1617 GPC.pdf Pt.I, Sec.B, 2a. (Chem 2) 1

Page 30 NON-CBI SUBMISSIONP12004 List of Attachments, Associated PMN Section No., ID: 004

Pt.I, Sec.B, 1c. | Pt.I, Sec.B, 2c. | Pt.I, Sec.B, 1c. (Chem 2) | Pt.I, Sec.B, 2c. (Chem 2)

Page 31 NON-CBI SUBMISSION

### X



## X Measured 1.1098 Measured



## X 006 FTIR Measured

10.3 Measured 5%

58.84 mg KOH/g (MW 953 Daltons) Measured Hydroxyl number Page 32 NON-CBI SUBMISSION

### X



## X Measured 1.1094 Measured



## X 007 FTIR Measured

10.4 Measured 5%

54.99 mg KOH/g (MW 1020 Daltons) Measured Hydroxyl Value Page 33 NON-CBI SUBMISSION

## ATTACHMENT HEADER SHEET Attachment Number 001 Attachment Name RS-1616 

## Associated PMN Section Number Pt.I, Sec.B, 1e. | Pt.I, Sec.B, 2e. Does not contain CBI 

## Report Number PCX7140224370258292

## ATTACHMENT HEADER SHEET Attachment Number 002 Attachment Name RS-1617 Structure 

## Associated PMN Section Number Pt.I, Sec.B, 1e. (Chem 2) | Pt.I, Sec.B, 2e. (Chem 2)

Does not contain CBI 

## Report Number PCX7140224370258292

## ATTACHMENT HEADER SHEET Attachment Number 003 Attachment Name RS-1616 & RS-1617 production scheme 

## Associated PMN Section Number Pt.2, Sec.A, 1d. | Pt.2, Sec.A, 1d. (#2) Does not contain CBI 

## Report Number PCX7140224370258292

## ATTACHMENT HEADER SHEET Attachment Number 004 Attachment Name 376784-1 

## Associated PMN Section Number Pt.I, Sec.B, 1c. | Pt.I, Sec.B, 2c. | Pt.I, Sec.B, 1c. (Chem 2) | Pt.I, Sec.B, 2c. (Chem 2) Does not contain CBI 

## Report Number PCX7140224370258292

## ATTACHMENT HEADER SHEET Attachment Number 006 Attachment Name RS-1616 FTIR 

## Associated PMN Section Number

Worksheet: Spectra Does not contain CBI 

## Report Number PCX7140224370258292

## ATTACHMENT HEADER SHEET Attachment Number 007 Attachment Name RS-1617 FTIR 

## Associated PMN Section Number Worksheet: Spectra (#2) Does not contain CBI 

## Report Number PCX7140224370258292

## ATTACHMENT HEADER SHEET Attachment Number 008 Attachment Name RS-1616 GPC 

## Associated PMN Section Number

Pt.I, Sec.B, 2a. Does not contain CBI 

## Report Number PCX7140224370258292

## ATTACHMENT HEADER SHEET Attachment Number 009 Attachment Name RS-1617 GPC 

## Associated PMN Section Number Pt.I, Sec.B, 2a. (Chem 2) Does not contain CBI 

## Report Number PCX7140224370258292