### 25F9R8KS 4180140421412699712 RC85CK

X

X 3 Page 1 NON-CBI SUBMISSION

### X

X X X X

Page 2 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 PC7079 

## X X

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## X

Phosphoric acid, mixed Bu and decyl and octyl and 2-(2-phenoxyethoxy)ethyl and 2-phenoxyethyl esters

1502809-48-4 

## X 373562-1 Ethox 4180 CAS number.pdf 

### R1R2PO4H where R1 and R2 = CH3(CH2)7 or 9, C6H5O(OC2H4)1-2, CH3(CH2)3, H

4180.jpg Page 4 NON-CBI SUBMISSIONA. Glycol ether EPH, a purchased blend of 90% 2-phenoxyethanol (CAS# 122-99-6) and 10% Diethylene glycol phenyl ether (CAS# 104-68-7)

B. 810 alcohol, a purchased mixture of 45% n-octanol (CAS# 111-87-5), 55% n-decanol (CAS# 112-30-1). C. tributyl phosphate (CAS# 126-73-8) D. phosphoric anhydride (CAS# 1314-56-3)

A mixture is prepared of glycol ether EPH and 810 alcohol. This mixture is phosphated by addition of tributyl phosphate and phosphoric anhydride. Additional octyl and decyl groups are added to the phosphate ester by additional reaction with a phosphated C810 alcohol, produced in a separate reaction of C810 alcohol and phosphate anhydride. A + B + C + D ----> R1R2PO4H where, A = Glycol ether EPH B = 810 alcohol C = tributyl phosphate D = phosphoric anhydride R1 and R2 = CH3(CH2)7 or 9, (C2H4)3CH3, C6H5(OC2H4)1-2, H

The product will contain mono and di butylphosphate esters and phosphate esters containing octyl, decyl, and mono and di ethylene glycol phenyl functionality. Based on stoichiometry alone the final product is expected to contain the following: 44.6% butyl, octyl phosphate ester 44.9% butyl, decyl phosphate ester 9.7% butyl, ethylene glycol phenyl phosphate ester 0.8% butyl, diethylene glycol phenyl phosphate ester

Page 5 NON-CBI SUBMISSIONPage 6 NON-CBI SUBMISSIONPage 7 NON-CBI SUBMISSIONEthox 4180, Ethox 4158

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## X

Phosphoric acid, mixed Bu and decyl and octyl and 2-(2-phenoxyethoxy)ethyl and 2-phenoxyethyl esters, potassium salts

1502809-56-4 

## X 373562-2 Ethox 4576 CAS Number.pdf 

### R1R2PO4-K+ where R1 and R2 = CH3(CH2)7 or 9, C6H5O(OC2H4)1-2, CH3(CH2)3, H

4576.jpg Page 9 NON-CBI SUBMISSIONA. Glycol ether EPH, a purchased blend of 90% 2-phenoxyethanol (CAS# 122-99-6) and 10% Diethylene glycol phenyl ether (CAS# 104-68-7)

B. 810 alcohol, a purchased mixture of 45% n-octanol (CAS# 111-87-5), 55% n-decanol (CAS# 112-30-1). C. tributyl phosphate (CAS# 126-73-8) D. phosphoric anhydride (CAS# 1314-56-3) E. potassium hydroxide (CAS# 1310-58-3)

A mixture is prepared of glycol ether EPH and 810 alcohol. This mixture is phosphated by addition of tributyl phosphate and phosphoric anhydride. Additional octyl and decyl groups are added to the phosphate ester by additional reaction with a phosphated C810 alcohol, produced in a separate reaction of C810 alcohol and phosphate anhydride. The product is then reacted with potassium hydroxide to form potassium salts. A + B + C + D + E ----> R1R2PO4-K+ where, A = Glycol ether EPH B = 810 alcohol C = tributyl phosphate D = phosphoric anhydride E = potassium hydroxide R1 and R2 = CH3(CH2)7 or 9, (C2H4)3CH3, C6H5(OC2H4)1-2, H

The product will contain potassium salts of mono and di butylphosphate esters and potassium salts of phosphate esters containing octyl, decyl, and mono and di ethylene glycol phenyl functionality Based on stoichiometry alone the final product is expected to contain potassium salts of the the following: 44.6% butyl, octyl phosphate ester 44.9% butyl, decyl phosphate ester 9.7% butyl, ethylene glycol phenyl phosphate ester 0.8% butyl, diethylene glycol phenyl phosphate ester

Page 10 NON-CBI SUBMISSIONPage 11 NON-CBI SUBMISSIONPage 12 NON-CBI SUBMISSIONEthox 4576

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## X

Phosphoric acid, mixed decyl and Et and octyl and 2-(2-phenoxyethoxy)ethyl and 2-phenoxyethyl esters

1502809-58-6 

## X 373562-3 Ethox EG-2 CAS Number.pdf 

### R1R2PO4H where R1 and R2 = CH3(CH2)7 or 9, C6H5O(OC2H4)1-2, CH3CH2, H

EG-2.jpg Page 14 NON-CBI SUBMISSIONA. Glycol ether EPH, a purchased blend of 90% 2-phenoxyethanol (CAS# 122-99-6) and 10% Diethylene glycol phenyl ether (CAS# 104-68-7)

B. 810 alcohol, a purchased mixture of 45% n-octanol (CAS# 111-87-5), 55% n-decanol (CAS# 112-30-1). C. triethyl phosphate (CAS# 78-40-0) D. phosphoric anhydride (CAS# 1314-56-3)

Triethylene phosphate is reacted with phosphoric anhydride with water present. This produces monosubstituted ethyl phosphate esters. A blend of 810 alcohol and Glycol ether EPH is added, producing ethyl, octyl, decyl, and -(2-phenoxyethoxy)ethyl and 2-phenoxyethyl esters. A + B + C +D ----> R1R2PO4H where, A = Glycol ether EPH B = 810 alcohol C = triethyl phosphate D = phosphoric anhydride R1 and R2 = CH3(CH2)7 or 9, C6H5O(OC2H4)1-2, CH3CH2, H

The product will contain mono and di ethylphosphate esters and phosphate esters containing octyl, decyl, and mono and di ethylene glycol phenyl functionality. Based on stoichiometry alone the expected composition is: 32.11% ethyl, octyl phosphate ester 32.29% ethyl, decyl phosphate ester 11.53% ethylene glycol phenyl, ethyl phosphate ester 0.97% diethylene glycol phenyl, ethyl phosphate ester 23.1% other phosphate esters containing ethyl, octyl, decyl, or mono and di ethylene glycol phenyl functionality

Page 15 NON-CBI SUBMISSIONPage 16 NON-CBI SUBMISSIONPage 17 NON-CBI SUBMISSIONEthox EG-2

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### X

117300 120000

Gellant for use in oil fracturing. 100 100 19 0 81 0

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### X

272000 280000

Gellant for use in oil fracturing. 100 100 0 0 100 0

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### X

920000 950000

Gellant for use in oil fracturing. 100 100 0 0 100 0

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### X



## X

30000 72 25 

## 1

Ethox 4097 is prepared in a dedicated tank, therefore it is not cleaned before or after use. Release #1 is from cleanning of the reaction vessal used to prepare the intermediate, Ethox 4158. The residue is estimated to be 113 kg Ethox 4158. This is 0.5% of the maximaum batch size (22,500 kg). Release #2 is from cleanning of the reaction vessal used to prepare the intermediate, Ethox 2989. The residue is estimated to be 56 kg Ethox 2989. This is 0.8% of the portion of the Ethox 2989 batch used to prepare Ethox 4180 (7,500 kg). Release #3 is from cleanning of the reaction vessal used to blend Ethox 4158 and Ethox 2989 to make the final product, Ethox 4180. Residue is estimated to be 150 kg Ethox 4180 which is 0.5% of the batch size (30,000 kg). Ethox Chemicals, LLC 1801 Perimeter Road Greenville Greenville SC 29605

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1a) Charge 810 alcohol using an electric pump (for trucks) or diaphragm pump (totes or drums). Steel toed rubber boots, rubber gloves, hard hat, safety goggles Liquid 2 1 5 1b) Charge glycol ether EPH from totes or drums using a diaphragm pump. Steel toed rubber boots, rubber gloves, hard hat, safety goggles Liquid 2 1 5 1c) Drum the product of this first step (Ethox 4097) into totes or drums using an electric pump. Steel toed rubber boots, rubber gloves, hard hat, safety goggles Liquid 2 1 5 2a) Charge tributyl phosphate using using the mechanical inline mixer. See continuation page. id: <P9SA2(3)C1R4> Liquid 2 1 5 2b) Charge phosphoric anhydride from totes or drums using an in-line mixer. Same as step 2a. Solid 2 1 5 2c) Charge heel(s) to tank using a diaphram pump. Same as step 2a. Liquid 2 1 5 2d) Drum the product of this step (Ethox 4158) into totes or drums using an electric pump. Same as step 2a. Liquid 2 1 5 3a) Charge 810 alcohol from storage tank using an electric pump. Safety glasses, steel toed, rubber boots, rubber gloves, hard hat Liquid 2 1 5 3b) Charge phosphoric anhydride from totes or drums using an in-line mixer. Same as step 2a. Solid 2 1 5 3c) Transfer the material to a finishing tank using pumps and hoses. Safety glasses, steel toed rubber boots, rubber gloves, hard hat Liquid 2 1 5 

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## (1)

3d) Charge heel(s) to tank using a diaphram pump. Same as step 2a. Liquid 2 1 5 3e) Drum product of this step (Ethox 2989) into totes or drums using an electric pump. Steel toed rubber boots, rubber gloves, hard hat, sleeves, face shield, apron Liquid 2 1 5 4a) Charge Ethox 2989 from totes or drums into reactor using an air pump. Steel toed rubber boots, rubber gloves, hard hat, sleeves, face shield, apron Liquid 2 1 5 4b) Charge Ethox 4158 from totes or drums into reactor using an air pump. Steel toed rubber boots, rubber gloves, hard hat, sleeves, face shield, apron Liquid 2 1 5 4c) Drum the final product (Ethox 4180) into totes or drums using an electric pump. Steel toed rubber boots, rubber gloves, hard hat, sleeves, face shield, apron Liquid 2 1 5 See continuation page. id: <P9SA2(1)C1R16> Min PPE: Safety glasses, steel toed rubber boots, rubber gloves, hard hat or as required by MSDS Liquid or Solid 2 1 5

Page 25 NON-CBI SUBMISSIONP9SA2(3)C1R4 Part II, Section A, 2.(3) Prot. Equipment, etc., Row 4

Safety glasses, steel toed, rubber boots, rubber gloves, hard hat, sleeves, organic cartridge respirator, face shield, apron

Page 26 NON-CBI SUBMISSIONP9SA2(1)C1R16 Part II, Section A, 2.(1) Worker Activity, Row 16

Sampling of raw materials, intermediates and products may be performed at any step. Sampling performed via a sample port in the reactor, or using a sample cup for drummed or toted materials.

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## X WCRSA Reedy River Plant SCR000197

1 113 POTW On site biological treatment. 0 2 56 POTW On site biological treatment. 0 3 150 POTW On site biological treatment. 0

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### X



## X

19000 72 2 

## 1

Ethox 4576 is produced from Ethox 4180 that was previously toted. The wastes produced during production of Ethox 4180 are reported from consolidated chemical 1. Release #1 is for rinsing of the totes used. Residue is estimated 77 kg of Ethox 4180 which is 0.5% of the material used (15,485 kg). Release #2 for production of 4576 is from cleanning of the reaction vessal used to treat Ethox 4180 with potassium hydroxide. Residue is estimated to be 95 kg Ethox 4576 which is 0.5% of the batch size (19,000 kg). Ethox Chemicals, LLC 1801 Perimeter Road Greenville Greenville SC 29605

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### X

5a) Charge Ethox 4180 from totes or drums into reactor using an air pump. Steel toed rubber boots, rubber gloves, hard hat, sleeves, face shield, apron Liquid 2 1 5 5b) Charge heels from drums or totes using an air pump. Steel toed rubber boots, rubber gloves, hard hat, sleeves, face shield, apron Liquid 2 1 5 5c) Charge KOH, 45%, from totes or drums into reactor using a dedicated KOH injection system. Steel toed rubber boots, rubber gloves, hard hat, sleeves, face shield, apron Liquid 2 1 5 5d) Drum the final product (Ethox 4576) into totes or drums using an electric pump. Steel toed rubber boots, rubber gloves, hard hat, sleeves, face shield, apron Liquid 2 1 5 See continuation page. id: <P9SA2(1)C2R5> Min PPE: Safety glasses, steel toed rubber boots, rubber gloves, hard hat or as required by MSDS Solid or liquid 2 1 5

Page 31 NON-CBI SUBMISSIONP9SA2(1)C2R5 Part II, Section A, 2.(1) Worker Activity, Row 5

Sampling of raw materials, intermediates and products may be performed at any step. Sampling performed via a sample port in the reactor, or using a sample cup for drummed or toted materials.

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## X WCRSA Reedy River Plant SCR000197

1 77 POTW On site biological treatment. 0 2 114 POTW On site biological treatment 0

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### X



## X

23000 72 30 

## 1

Ethox 4097 is prepared in a dedicated tank, therefore it is not cleaned before or after use. Release #1. This is water from cleanning of the reaction vessal after use. It is estimated that 115 kg of residual EG-2, which is estimated to be 1% of the batch, will be sent for on-site biological pretreatment before it is released to POTW. Ethox Chemicals, LLC 1801 Perimeter Road Greenville Greenville SC 29605

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1a) Charge 810 alcohol using an electric pump (for trucks) or diaphragm pump (totes or drums). Steel toed rubber boots, rubber gloves, hard hat, safety goggles Liquid 2 1 5 1b) Charge glycol ether EPH from totes or drums using a diaphragm pump. Steel toed rubber boots, rubber gloves, hard hat, safety goggles Liquid 2 1 5 1c) Drum the product of this first step (Ethox 4097) into totes or drums using an electric pump. Steel toed rubber boots, rubber gloves, hard hat, safety goggles Liquid 2 1 5 2a) Charge triethyl phosphate using using the mechanical inline mixer. See continuation page. id: <P9SA2(3)C3R4> Liquid 2 1 5 2b) Charge phosphoric anhydride from totes or drums using an in-line mixer. Same as step 2a. Solid 2 1 5 2c) Charge Ethox 4097 from totes or drums into reactor using an air pump. Same as step 2a. Liquid 2 1 5 2d) Filter the product during transfer, using pumps and hoses, to a finishing tank. Safety glasses, steel toed, rubber boots, rubber gloves, hard hat Liquid 2 1 5 2e) Charge heels from drums or totes using a diaphram pump. Same as step 2a. Liquid 2 1 5 2f) Drum the final product (Ethox EG-2) into totes or drums using an electric pump. Same as step 2a. Liquid 2 1 5 See continuation page. id: <P9SA2(1)C3R10> Min PPE: Safety glasses, steel toed rubber boots, rubber gloves, hard hat or as required by MSDS Solid or liquid 2 1 5

Page 36 NON-CBI SUBMISSIONP9SA2(3)C3R4 Part II, Section A, 2.(3) Prot. Equipment, etc., Row 4

Safety glasses, steel toed, rubber boots, rubber gloves, hard hat, sleeves, organic cartridge respirator, face shield, apron

Page 37 NON-CBI SUBMISSIONP9SA2(1)C3R10 Part II, Section A, 2.(1) Worker Activity, Row 10

Sampling of raw materials, intermediates and products may be performed at any step. Sampling performed via a sample port in the reactor, or using a sample cup for drummed or toted materials.

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## X WCRSA Reedy River Plant SCR000197

1 115 POTW On site biological treatment 0

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### 0

Page 40 NON-CBI SUBMISSIONPage 41 NON-CBI SUBMISSIONPage 42 NON-CBI SUBMISSION001 4180 structure 4180.jpg Pt.I, Sec.B, 1e. 1 002 Ethox 4180 CAS number Ethox 4180 CAS number.pdf Pt.I, Sec.B, 1c. 1 003 4576 structure 4576.jpg Pt.I, Sec.B, 1e. (Chem 2) 1 004 Ethox 4576 CAS Number Ethox 4576 CAS Number.pdf Pt.I, Sec.B, 1c. (Chem 2) 1 005 Ethox EG-2 structure EG-2.jpg Pt.I, Sec.B, 1e. (Chem 3) 1 006 Ethox EG-2 CAS Number Ethox EG-2 CAS Number.pdf Pt.I, Sec.B, 1c. (Chem 3) 1 007 4180 scheme 4180 scheme.jpg 1 008 4576 scheme 4576 scheme.jpg 1 009 EG-2 scheme EG-2 scheme.jpg 1 010 Ethox 4180 FTIR Ethox 4180 FTIR.pdf Worksheet: Spectra 1 011 Ethox 4576 FTIR Ethox 4576 FTIR.pdf Worksheet: Spectra (#2) 1 012 EG-2 FTIR EG-2 FTIR.pdf Worksheet: Spectra (#3) 1

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### X



## X Measured 1.01



## X 010 FTIR Measured

2.0 - 3.0 Measured 5%

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### X



## X Measured 1.07 Measured



## X 011 FTIR Measured

3.2 Measured 5%

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### X



## X Measured 1.049 Measured



## X 012 FTIR Measured

1-3 Measured 5% IPA:water 1:1

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## ATTACHMENT HEADER SHEET Attachment Number 001 Attachment Name 4180 structure 

## Associated PMN Section Number

Pt.I, Sec.B, 1e. Does not contain CBI 

## Report Number 4180140421412699712

## ATTACHMENT HEADER SHEET Attachment Number 002 Attachment Name Ethox 4180 CAS number 

## Associated PMN Section Number

Pt.I, Sec.B, 1c. Does not contain CBI 

## Report Number 4180140421412699712

## ATTACHMENT HEADER SHEET Attachment Number 003 Attachment Name 4576 structure 

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

## Report Number 4180140421412699712

## ATTACHMENT HEADER SHEET Attachment Number 004 Attachment Name Ethox 4576 CAS Number 

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

## Report Number 4180140421412699712

## ATTACHMENT HEADER SHEET Attachment Number 005 Attachment Name Ethox EG-2 structure 

## Associated PMN Section Number Pt.I, Sec.B, 1e. (Chem 3) Does not contain CBI 

## Report Number 4180140421412699712

## ATTACHMENT HEADER SHEET Attachment Number 006 Attachment Name Ethox EG-2 CAS Number 

## Associated PMN Section Number Pt.I, Sec.B, 1c. (Chem 3) Does not contain CBI 

## Report Number 4180140421412699712

## ATTACHMENT HEADER SHEET Attachment Number 007 Attachment Name 4180 scheme 

## Associated PMN Section Number

N/A Does not contain CBI 

## Report Number 4180140421412699712

## ATTACHMENT HEADER SHEET Attachment Number 008 Attachment Name 4576 scheme 

## Associated PMN Section Number

N/A Does not contain CBI 

## Report Number 4180140421412699712

## ATTACHMENT HEADER SHEET Attachment Number 009 Attachment Name EG-2 scheme 

## Associated PMN Section Number

N/A Does not contain CBI 

## Report Number 4180140421412699712

## ATTACHMENT HEADER SHEET Attachment Number 010 Attachment Name Ethox 4180 FTIR 

## Associated PMN Section Number

Worksheet: Spectra Does not contain CBI 

## Report Number 4180140421412699712

## ATTACHMENT HEADER SHEET Attachment Number 011 Attachment Name Ethox 4576 FTIR 

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

## Report Number 4180140421412699712

## ATTACHMENT HEADER SHEET Attachment Number 012 Attachment Name EG-2 FTIR 

## Associated PMN Section Number Worksheet: Spectra (#3) Does not contain CBI 

## Report Number 4180140421412699712