Appendix A - ACS Symposium Series (ACS Publications)

Appendix A

Physical Properties of Fuel Oxygenates and Additives 1

2

Downloaded by UNIV OF MICHIGAN ANN ARBOR on February 18, 2015 | http://pubs.acs.org Publication Date: November 6, 2001 | doi: 10.1021/bk-2002-0799.ch018

Donna L . Drogos and Arthur F. Diaz 1

Santa Clara Valley Water District, 5750 Almaden Expressway, San Jose, CA 95118 ChemicaI and Materials Engineering Department, San Jose State University, One Washington Square, San Jose, CA 95192-0086

2

The use of oxygenates in gasoline formulations and the subsequent release of these compounds to the environment has lead to interest in the physical properties of oxygenates and other gasoline constituents. Knowledge of a compound's physical properties and chemical structure enables one to predict its behavior in the environment and identify potential cleanup methods. Often environmental data from actual release sites is unavailable for compounds in production or being researched and developed for future use. In these instances the only data available to evaluate the behavior of a compound is published physical property data obtained by laboratory measurements or predictive calculations. This appendix compiles the available data for fuel oxygenates and additives. The appendix consists of four tables that list the physical properties of the common alkyl ethers (Table 1), alkyl ethers being developed for use in fuel formulations (Table 2), alkyl alcohols (Table 3), and aromatic compounds (Table 4). The one ester, tert-Butyl Formate appears in Table 2. References 1. 2. 3.

4. 5.

258

Aldrich Chemical Company, "Aldrich Catalog/Handbook of Fine Chemicals," Aldrich Chemical Company, Inc., Milwaukee, WI, 2000-2001. Bauman, B., "MTBE and Groundwater Quality: Bioremediation Research," EPA OUST National Conference, March 12, 1997. Brown, Α., et al, "A Review of Treatment Technologies for Methyl tertiary Butyl Ether (MtBE) in Drinking Water, "Proceedings of the ACS 1997 Pacific Conference on Chemistry and Spectroscopy, April 1997. Budavari, S. et al., "Merck Index, 12 Edition," Merck Research Laboratories, Whitehouse Station, NJ, 1996. CambridgeSoft Corp., Chemfinder Database and Internet Search, 2001, http://www.chemfinder.com/ th

© 2002 American Chemical Society

In Oxygenates in Gasoline; Diaz, A., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2001.


Boiling Point (°Q

th

st

Properties Chemical Class CAS No. CRC No. (81 Ed.) Merck No. (12 Ed.) Formula Structural Formula Molecular Weight Melting Point (°Q

3

12

3

3

55.2 (4,10,12,16, 26)

55 (12, 13, 14) 55 - 56 ( l )

53.6- 55.2 (23,30)

-108.6 (16) -108.60 (10) -109 (4)

88.15

5

C H 0 CH OC(CH )

6111

Methyl tert-Butyl Ether MTBE Ether 1634-04-4 10072

TABLE 1. ALKYL ETHERS

2

5

14

2

85 - 86 ( l ) 86 (13, 14, 30) 86.3 (4, 12, 16, 26) 86-87 (12)

102.18

6

C H 0 C H C(CH3) OCH3

654

tert-Amyl Methyl Ether TAME Ether 994-05-08 3396

3

3

14

2

(16)

67 (30) 69-71 (4) 72 (14) 72.2 (12, 26) 72.6 (16)

-94

102.18

6

C H 0 (CH ) COC H

3821

5

Ethyl tert-Butyl Ether ETBE Ether 637-92-3 10040

2

7

2

16

5

3

2

101 (12, 13, 14) 101 -102 (12) 102 (16, 26)

5

C H 0 C H C(CH ) OC H 116.2

N/A

tert-Amyl Ethyl Ether TAEE Ether 919-94-8 3375


2

3

2

Continued on next page.

-60 (24) -85.5 (19) -85.50 (10,19) -86 (19, 27) -86.8 (16) 68 (13, 19) 68-69 (1,30) 68.2 (26) 68.30 (10) 68.34 (19)

3

(CH ) CHOCH (CH ) 102.18

CÔH^O

5231

DIPE Ether 108-20-3 10120

Diisopropyl Ether


Solubility inEtOH

Water Solubility (mg/l)

3

...continued Liquid Density (g/cm @ 20°C)

Properties Boiling Point (°Q

0.74

(26)

MTBE TAME 72.8 (4) 73 (12, 13) 73.1 (4)

ETBE TAEE

91 (19,30)

68.5 (16) 68.51 (19) 69 (19, 27)

DIPE

very soluble (16)

soluble (16) very soluble (16)

very soluble (16)

very soluble (16)

miscible (16)

50,000 (30)

51,260(25)

(19, 27, 30)

12,000 @20°C (19) slightly soluble (16)

48,000(4,12,13,26)

0.764 (5) 0.73 (30) 0.71854 (19) 0.75 (26) 0.7404(4,25) 0.77 (26, 30) 0.74 (26) 0.7239 (19) 0.7657 (12) 0.7404 - 0.7578 (23) 0.7656 @25°C (12) 0.7404 (4,12) 0.7241 (16) 0.751 @18°C (16) 0.7405 (11,12,16) 0.770 @25°C (1) 0.7353 @25°C (12) 0.7609 @25°C (12) 0.73 (26) 0.744 (23, 30) 0.7703 (4, 12, 16) 0.736 @25°C (16) 0.7705 @15.6°C (13) 0.7360 (19) 0.735 @25°C (29) 0.7758 @15.6°C (13) 0.7452 @15.6°C (13) 0.721 @25°C (29) 0.7352 @25°C (12) 0.725 @25°C ( l ) 0.740 @25°C (1) 0.7289 @15.6°C (13) 0.7460 @15.6°C (13) 0.73@10°C (27) 0.736-0.7491 (30) 42,000-54,300 (3) 11,500(4,12,13) 7,650 (30) 4,000 (12,13) 2,000 (26) 43,000 (15) 12,000 (26) 12,000(4,12,13,26) 2,039 (19,30) 43,000-54,300 -20,000 (30) 26,000 (15) 4,900 (19) (23, 30) insoluble (16) 9,000 @ 20°C

Table 1. Continued



Log Kow @25°C

Vapor Density (Air = 1) Log Koc @25°C

Properties Vapor Pressure (mmHg, 25°C)

1.23

(ll)

1.16(19) 1.20(23,30)

0.94 (19, 29) 1.01 (19) 1.06 (19)

0.94- 1.30(23,26)

1.091 (17) 1.91 (30)

1.09(25)

1.049 (30) 1.05 (22, 23)

1.04(25)

240 (26) 245 (4, 12, 25) 245 -251 (23) 245 - 256 (30) 250 (11) 251 (3) 3.1 (26) 3.80 (20) 0.55 -0.91 (26) 1.01 (11) 1.035 (30)

MTBE

1.55 (22)

1.74

(30)

0.95 (30) 2.2 (30)

1.27 (30) 2.2 (30)

(30)

3.6 (26)

152

130(4,12, 26)

ETBE

3.6 (26)

68.3 (30) 75 (4, 12, 26)

TAME

4.0 (26)

50 (12)

TAEE



1.95 (19) 2.03 (19)

1.56(19)

1.52 (19, 26,29, 30)

3.52 (27) 3.6 (26) 1.13 (26) 1.46 (30) 1.82 (30)

130 @20°C (27) 149-151 @20°C (30)

159(26)

149.11 (19) 150.71 (19)

DIPE


Dimensionless Henry's Law Constant @25°C

3

Properties Log Kow @25°C ...continued Henry's Law Constant (atm-m /mol) @25°C

1.24 (22, 25) 1.3 (19)

MTBE

2.2E-2-1.2E-1 (26) 2.399E-02 (23,30) 2.6E-02 (17) 2.7E-02 (30) 4.496E-02 (30)

2.16E-02(23)

1.41E-04 (19) 5.28E-04 (23) 5.28E-4 - 3E-3 (26) 5.4106E-04 (29) 5.5E-04 (25) 5.87E-04 (19, 23,30) 5.9E-04 (22) 5.92E-04 (19) 6.59E-04 (11) 1.1E-03 (30) 1.4E-03 (23,30) 3.00E-03 (17) 3E-03 (23,30) 3.01E-03 (19) 1.226E-01 (23,30)

Table 1. Continued

2.64E-03 (26) 2.66E-03 (30) 2.7E-03 (22)

1.087E-01 (30) 1.1E-01 (26)

5.191E-02 (30) 8.1E-02 (26)

ETBE

1.27E-03 (30) 1.3E-03 (22) 1.95E-03 (26)

TAME

TAEE


1.95E-01 (30) 1.99E-01 (26) 2.399E-01 (30) 4.075E-01 (30)

1.7593E-03 (29) 4.77E-03 (19, 26, 30) 5.87E-03 (19,30) 9.97E-03 (19,30)

DIPE


2

Research Octane Number (RON) Motor Octane Number (MON) Blending Octane No. (R+M)/2

2

Amount in Gasoline (W%0 /V%0 )

0

Properties Dimensionless Henry's Law Constant @25°C ...continued Flash Point ( C)

(7)

105(4, 9,13)

109(4, 9) 110(13) 111(7) 118(17)

105.5

98 (14) 99 (7)

111 (7,13)

110(4,9)

101 (14) 103 (7)

118(6, 14, 22) 119(6,7)

112(6, 7, 14)

-19(13)

2.0%/12.6% (20) 2.0%/12.8% (7) 2.7%/17.0% (20) 2.7%/17.1% (6) 2.7%/17.4% (28)

13)

ETBE

2%/12.8% (7) 2.7%/16.6% (6) 2.7%/16.7% (28) 2.7%/17.25% (7)

-11 ( 1 ,

TAME

101 (14) 103 (7)

119(7)

118 (6, 22)

117(14)

2.74%/15% (6)

(7, 20,28)

2%/11.0% (7, 20) 2.7%/15.0%

-32(1)

-26 (13) -27.78 (10,29) -28 (4) -30 (3)

(23, 30)

5.772E-02 (23,30) 1.8E-02 @20°C

MTBE

(14)

100 (13) 109 (9)

112(8)

95

105 (8,14)

107

(13)

110(22)

-12 ( l , 13) -27.78 (10,29)

DIPE


2.7%/19.3% (28)

TAEE



Odor Character

Taste Threshold in Water (ug/L)

Odor Threshold in Water (ug/L)

3

Odor Threshold in Air (mg/m )

Oxygen (W%)

Properties Neat RVP (psi) 100°F Blending RVP (psi)

7.8

(4, 14)

MTBE

40 - 140 (2) 134 (20) 2 4 - 135 ppb (21) terpene like, ether, alcohol (11) sweet (27)

39 (11,20)

95 (20) 10 -100 (3)

45 (11,20)

15-180(21)

18.2 (9) 0.32 - 0.47 (25) 5 - 53 ppb (3) 53ppbv (11) 300ppbv (11) 15-40 (2)

18.15(6,13)

7.8 psi (14) 8 psi (4, 13) 8 psi/55 kPa (13) 8-10 psi (9)

Table 1. Continued

128

194

15.7

15.66

(9)

(20)

(20)

(9)

(6,13)

3-5 psi

2.5 psi (4,14)

47

49

(9)

(6,13)

(20)

(20)

15.7

15.66

4 (4,13)

(4,14)

4 psi/28 kPa (13) 3-5 psi (9)

4.0

2(13)

(4, 14)

ETBE

2 psi / 14kPa (13)

2.5

TAME (14)

2 psi / 14kPa (13) 13.77 (13) 13.8 (9)

2(13)

0 - 2 psi (9) 1.2 psi (14)

1.2

TAEE


(13)

sweet, pleasant (27)

0.10(27)

15.66

0.7 (13) 0.7 psi/5kPa (13)

DIPE


Properties USEPA Drinking Water Health Advisory or MCL California DHS Primary MCL Secondary MCL Action Level Uses

5 ug/L 13 ug/L gasoline octane booster (4)

13 ppb

20-40ug/L

MTBE

fuel additive for gasoline; gasoline octane booster (4)

TAME

gasoline additive (4)

ETBE

TAEE


solvent for oils, waxes, and resins; paint and varnish removers (27)

DIPE


Boiling Point (°C)

th

st

Properties Chemical Class CAS No. CRC No. (81 Ed.) Merck No. (12 Ed.) Formula Structural Formula Molecular Weight Melting Point (°C)

3

2

5

143 (16)

7

3

CgHigO C H C(CH ) OC H 130.23

2

tert-Hexyl Ethyl Ether THxEE Ether 5756-43-4

T A B L E 2: A L K Y L E T H E R S

2

2

5

166 (16)

-68.3 (16)

2

OC H 144.26

C4H9C(CH3)

C9H QO

tert-Heptyl Ethyl Ether THpEE Ether 103-44-6

7

16

3

3

2

126.1 (16)

113(12)

-110 (13) 110-115(14)

3

7

C H 0 C H C(CH ) OCH 116.20

tert-Hexyl Methyl Ether THxME Ether 4747-07-3

130 - 135 (14) 151 (16)

3

3 2

CgHigO C4H9C(CH ) OCH 130.23

tert-Heptyl Methyl Ether THpME Ether 629-32-3

6

3

-24.82 (4)

-24.8 (1,5,16, 26)

-138.5 (5,19) -141 (l) -141.49 (io, 19) -141.5 (5,16) -141.50(4) -22 (5) -23.60 (19) -24.00 (19)

46.07

3

2

C H 0 CH OCH

6148

DME Ether 115-10-6 7523

Dimethyl Ether


3

0

82 (30)

3

5

2

C Hi O (CH ) COCH Ο 102.13

Tert-Butyl Formate TBF Ester 762-75-4


Solubility in EtOH Vapor Pressure (mmHg, 25°C) Vapor Density (Air - 1) Log Koc @25°C


3

Properties Boiling Point (°C) ...continued Liquid Density (g/cm @20°C)

very soluble (16)

0.7722 (16)

THxEE

0.790 (16)

THpEE

(13)

0.7860 @15.6°C

0.7815(12)

THxME -24.84 (10,19)

DME

TBF

(16)


1.15(24)

758-5,086 @25°C (26) 81 @20°C (30) 4,450 (5, 24) 1.6 (26) 1.62 (5) -0.29 (26) 1.11 (30) 0.1 (26)

0.66 (26) 0.886 (30) 0.6612 (19) 0.6689 (19) 0.655 @25°C (29) 35,300 (24) -40,000 (30) 47,000-353,000 (5,26) 47,483 (19) 71,000 (19) 270,876 (19) 292,479 (19) 353,000 (19) soluble (16) very soluble soluble (16)

0.7862 (16)

THpME



THxEE

Research (THxEEl) 105.9 (8) Octane Number (THxEE2) 104.9 (8) (RON) (THxEE3) 101.4 (8)

Dimensionless Henry's Law Constant @25°C Flash Point (°C)

Henry's Law Constant (atm-m3/mol) @25°C

Properties Log Kow @25°C

Table 2. Continued THpEE THxME THpME TBF

-41 (4,5) -41.11 (29)

2.03E-2-4.15E-2(26) 1.111E-02 (30)

0.23 (19) 4.89E-4 - 9.97E-4 (26) 2.72E-04 (30) 4.89E-04 (19) 7.4E-04 (19) 9.97E-04 (19) 1.04E-03 (19) 7.63E-03 (5) 6.6435E-04@18°C (29)

0.1 @18°C(29) 0.10(19) 0.12(19)

-0.188 (19) -0.27 (19)

DME



THxEE Properties Motor Octane (THxEEl)93.1(8) Number (MON) (THxEE2)91.9 (8) (THxEE3)91.5 (8) Blending (THxEEl) 100 (9) Octane No. (THxEE2) 99 (9) (R+M)/2 (THxEE3) 96 (9) Neat RVP (psi) 100°F Blending RVP (psi) Oxygen (W%) (THxEEl) 12.3 (9) (THxEE2) 12.3 (9) (THxEE3) 12.3 (9) Odor Character Uses THpEE

(13)

1 psi/7kPa (13) 13.77 (13) 13.8 (14)

1(6)

1 (14)

95

THxME

(14)

12.3 (14)

0.9 psi (14)

0.9

THpME

slight ethereal odor (4) alternative diesel fuel (4)

DME


TBF


Boiling Point (°C)

th

st

Properties Chemical Class CAS No. Formula CRC No. (81 Ed.) Merck No. (12 Ed.) Molecular Structure Molecular Weight Melting Point (°C)

6

82.41

(4)

101.8(27) 102 (1,22)

64.6 (16) 64.7 (4, 29, 30) 64.70 (10)

82.4 (16,26)

78 - 79 (30) 78.2 (16)

78 (1,13)

-114.10(10) -117(27)

102.4 (16)

-9(4) -11.9(27) -12(1)

-8.8 (16)

25 (27) 25 - 26 (1) 25.4 (16) 25.6 (4) 25.66 (10) 25.7 (4) 25.82 (29) 80 - 83 (13)

-114.1 (4,16,29)

-114(27)

-97.6 (16) -97.68 (10,29) -97.8 (4) -98 (27)

2

74.12

2

32.04

3

46.07

3

CH CH C (CH ) OH 88.15

3

12

7282

5

tert-Amyl Alcohol TAA Alcohol 75-85-4 C H 0 3628

(CH ) COH 3

1577

10389

C4H10O

tert-Butyl Alcohol TBA Alcohol 75-65-0

CH3OH

2

6024

4

MeOH Alcohol 67-56-1 CH 0 7581

Methanol

CH CH OH

3

3806

2

EtOH Alcohol 64-17-5 C H 0 5672

Ethanol

TABLE 3: ALKYL ALCOHOLS

8

2

82 (13) 82.2 (22) 82.26 (10,29)

-89.5 (1,16)

-89 (27)

-88.5 (4,10)

-86 (27) -87.87 (29)

60.10

3

(CH ) CHOH

5227

3

IPA Alcohol 67-63-0 C H 0 10335

Isopropanol


2

16,

107.03 (29) 107.66 (10) 107.8 (16)

27, 29)

-108 (1,4, 10,

2

3

(CH ) CHC H OH 74.12

5146

10388

C4H10O

IBA Alcohol 78-83-1

Isobutanol


(4,26)

65 (13,27) 83 (1,27)

82.42 (10,29) 82.9 (30)

TBA 102.5

TAA (4) (4)

(1,27)

82.5

82.4

82.3 (16)

IPA

108

107.9

(1,4)

(22,27)

IBA

121.58(30)

44 (26) 49 - 56.5 (30) 50 (27) 43.9 @20°C (27)

40 - 42 (30) 41 (26) 42 (27)

miscible (16)

miscible (16)

miscible (16)

Solubility in EtOH Vapor Pressure (mmHg, 25°C) 126 (18) 92 @20°C (27)

miscible (16)

miscible (16)

miscible (16)

miscible (16)

soluble (16)

(27)

140,000 @30°C

68,200(22)

10

(27)

soluble (16)

(16)

slightly soluble

(27)

95,000 @18°C


32 @20°C (27) 57 @30°C (27)

miscible (16)

miscible (16)

0.80 (27) 0.78 (27) 0.805 (22) 0.7914 (16) 0.78 (27) 0.789 (4) 0.8018(16) 0.78505 (4) 0.7915 (4) 0.78581 (4) 0.8084 (4) 0.7893 (16) 0.802 (22) 0.796 (30) 0.7887 (16) 0.789 (22) 0.809 (27) 0.79 (26, 27) 0.787 @25°C(29) 0.79 (26) 0.797 @25°C 0.7809 @25°C 0.8096 (16) 0.794 (30) (16) 0.791 (30) (29) 0.805 @25°C ( l ) 0.787 @25°C (29) 0.7963 @15.6°C 0.7810 @15.6°C (13) 0.775 @25°C (1) 0.803 @25°C (l) 0.790 @25°C (1) (13) 0.7899 @15.6°C 0.8@15°C(27) 0.806 @15°C (4) 0.7939 @15.6°C 0.783 @25°C(29) (13) (13) 0.785 @25°C ( l )

78.5

78.29 (10,29) 78.3 (22) 78.4 (27)

MeOH


3

...continued Liquid Density (g/cm @ 20°C)

Properties Boiling Point (°C)

EtOH



2.097E-04 (30) 2.1E-04 (17) 2.52E-04 (17) 2.522E-04 (30) 2.57E-04 (27) 2.571E-04 (30)

Dimensionless Henry's Law Constant

3

5.13E-06(30) 5.2E-06 (22) 6.17E-06 (30) 6.29E-06 (30) 8.1083E-06(29)

-0.31 (29,30) -0.32 (26,27)

-0.14(26) 0.2 (30) 1.21 (30) 1.77(22) -0.16(30)

1.6 (26, 27)

EtOH

Henry's Law Constant (atm-m /mol, 25°C)

Log Kow @25°C

Properties Vapor Density (Air = 1) Log Koc @25°C

Table 3. Continued

1.087E-04(30) 1.91E-04(27)

4.42E-06 (30) 4.55E-06 (18) 4.6E-06 (22) 5.1932E-06(29)

-0.77 (22,29) -0.82 (27)

-0.66 (27) -0.75 (30)

1.1 (27) 1.11(4) 0.44 (30) 0.921 (30) 0.95 (22)

MeOH

1.04E-05 (30) 1.175E-05 (30) 1.19E-05 (30) 1.21E-05 (26) 1.4E-05 (22) 1.47E-05 (30) 1.7279E-05 (29) 4.251E-04(30) 4.80E-04 (30) 4.803E-04 (30) 4.864E-04 (30) 4.90E-04 (27) 5.03E-04 (26) 5.927E-04 (30)

0.35 (26, 29, 30)

2.55 (27) 2.6 (26) 0.37 (27) 1.57 (26, 30)

TBA

5.62E-04 (27)

0.89 (22,27)

TAA

0.65 (27) 0.76 (22,29) 0.83 (27)

0.95 (22)

2.55 (27)

IBA

3.47E-04 (27)

7.90E-06 (22) 1.1796E-05 (29) 1.2408E-05 (29) 1.2E-05 (22)

0.05 (22, 29)

2.07 (27) 2.1(5) 1.4(22)

IPA



12.78 (10,29) 13 (4, 13) 16(1)

EtOH 11(13) 11.11 (10,29) 12(4)

MeOH

2

2

2.0%/5.7% (7,20) variable (28) Amount in 2.7%/7.5% (28) Gasoline (W%0 /V%0 ) 2.7%/7.7% (7,20) 3.5%/10.0%(7,20) 3.7%/10% (6) 133 (22) Research 111 (17) Octane Number 129 (6,7) (RON) 130 (22) 105 96(7) Motor Octane Number (MON) 102 116(9) Blending 112.5(7) Octane No. 119(13) 113 (4, 9) (R+M)/2 115(13) 129 (17) Neat RVP 2.3 (4) (psi) 100°F Blending RVP 40 (13) 14 psi (17) 40 psi/276 kPa 18(4,13) (psi) (13) 18psi/124kPa(l3) 31 -60 psi (9) 17-22 psi (9)

Properties Flash Point (°C)

9 (4, 13) 9 psi / 62 kPa (13) 10-15(9)

106 (22)

27 (1) 27.78 (10,29) 28(4)

IBA


14 (13) 14psi/ 97kPa (13)

106 (13)

97 (13) 101 (4, 9)

1.7(4)

98

100

11(1) 11.67 (10,29) 11.7(4) 12 (13) 2.7%/9.6% (20)

IPA

121 (22)

19(4) 21(1)

TAA

109 (22)

2.7%/11.8% (28)

11 (1,13) 11.1(4) 11.11 (10,29)

TBA



California DHS Action Level Uses

3

Odor Character Odor Threshold in Air (mg/m ) Taste Threshold in Water (ug/L) Odor Character

Oxygen (W%)

Properties

10-20,000 (18)

MeOH 49.33 (13) 49.9 (9)

camphor-like odor (4)

TBA 21.3 (13) 21.6 (9)

12 ppb EtOH gasoline octane EtOH dénaturant (27) dénaturant, booster (4) gasoline octane gasoline octane booster; booster (4) ingredient of as blending gasoline and agent up to 7% diesel oil fuels; to increase EtOH dénaturant octane rating of (4) unleaded gasoline (27) anti-icing additive (27)

EtOH 34.7 (9) 34.73 (13)

Table 3. Continued

EtOH

8.42 (27) 30.03 (27)

TAA

IBA

(4)

EtOH dénaturant

(27)

de-icing agent for liquid fuels

MeOH

1,750(27)

TBA

sharp, musty (27) sweet, musty (27)

IPA 26.62 (13)



3

Liquid Density (g/cm @20°C)

Boiling Point (°C)

th

st

Properties Chemical Class CAS No. Formula CRCNo. (81 Ed.) Merck No. (12 Ed.) Molecular Weight Melting Point (°Q

0.8786 (30) 0.866 (4) 0.865 @25°C 0.88 (23, 30) (1,29) 0.873 @25°C(29)

110.6(1,4,16, 30,23) 110.63 (10,29)

-93(1) -94.9 (16) -94.97 (10,29) -95 (4)

5.5 (1,4,16) 5.53 (10,29)

80 (l) 80.0 (16) 80.09 (ίο, 29) 80.1 (4,23,30)

92.14

9667

Aromatic 108-88-3 CyHg 1947

Toluene

78.11

1094

867

CÔHO

Aromatic 71-43-2

Benzene

T A B L E 4: A R O M A T I C COMPOUNDS

106.17 -25 (4) -25.17 (10,29) -25.2 (16) -25 to -23 (1)

-47.4 (4) -47.8 (16) -47.85 (10,29)

10214

Aromatic 95-47-6 QH10 1452

o-Xylene

106.17

10214

Aromatic 108-38-3 CgHio 1453

m-Xylene

12-13(1) 13 - 14 (4) 13.2 (16) 13.25 (10) 13.26(29) 137-138 (4,23,30) 138(1) 138.3 (16) 138.36(10,29)

106.17

10214

Aromatic 106-42-3 QH10 1454

p-Xylene

136(1) 136.1 (16) 136.20(10,29) 136.25 (4, 23,30)

138- 139 (l) 139.1 (16) 139.12(10,29) 139.3 (4, 23,30)


143 _ 145 (l) 144 (4) 144.4 (23, 30) 144.43 (10,29) 144.5 (16) 0.86104 (4) 0.8801 (4) 0.8642 (16) 0.867 (23,30) 0.8842(23,30) 0.88 02 (23,30) 0.858 @25°C(29) 0.8670 (16) 0.865 @25°C(29) 0.861 @25°C(29) 0.870 @25°C (1) 0.8611 (16,23,30)

-94.9 (16) -94.95 (10,29) -95 (1) -95.01 (4)

106.17

3812

1668

Aromatic 100-41-4

Ethyl Benzene



3

Henry's Law Constant (atm-m /mol, 25°C)

3

Ethyl Benzene

m-Xylene

o-Xylene

p-Xylene

8.3 (23,30)

9.53 (23,30) 4.57 (20)

28.4 (23, 30) 3.97 (20)

4.57 (20)

6.6 (23,30)

miscible (16)

8.7 (23,30)

miscible (16)

1.56 - 2.25(23,30) 1.98 - 3.04(23,30) 2.04 - 3.15(23,30) 1.68 - 1.83(23,30) 2.05 - 3.08(23,30) 2.94 (30) 2.72 @20°C (29) 2.31 (30) 2.48 @20°C (29) 2.20 (30) 2.72 @20°C (29) 2.72 @20°C (29) 2.72 @20°C (29)

miscible (16)

miscible (16)

miscible (16)

0.86 69 (16, 23,30) 0.867 @25°C (1) 0.868 @25°C (1) 0.876 @25°C(29) 0.866 @25°C(l) 0.8684 @15°C(4) 0.8802 @10°C (16) 156 (23,30) 175 (23, 30) 161 (23,30) 146 (23, 30) 534.8 (23, 30) insoluble (16) insoluble (16) insoluble (16) insoluble (16) insoluble (16)

Toluene

2.11 -2.80(23,30) 2.68-3.26(23) 2.73 (23, 29, 30) 3.15 (23,29, 30)

2.77-3.12 3.08 -3.29(23,30) 3.09 - 3.37(23) (23, 30) 3.15 (23,29, 30) 3.2 (29) 3.12 (23,29, 30) 3.20(23,30) 5.43E-03 (23,30) 5.94E-03 (23,30) 8.1413E-03 (29) 6.7775E-03 (29) 4.1895E-03 (29) 6.1547E-03 (29) 6.3522E-03 (29) 8.44E-03 (23,30) 7.68E-03 (23,30) 5.1E-03 (23,30) 7.68E-03 (23,30) 6.60E-03 8.75E-03 (23)

Benzene Properties Liquid Density 0.874 @25°C (l) (g/cm @ 20°C) 0.87 65 (16,23) 0.8787 @15°C(4) ...continued Water 1,780(23,30) 1,791 (23) Solubility slightly soluble (mg/l) (16) Solubility in miscible (16) EtOH Vapor Pressure 76 (30) (mmHg, 25°C) 95.19(23,30) Vapor Density 3.36 (20) (Air = 1) Log Koc 1.1-2.5(23) @25°C 1.50-2.16(30) 1.8- 1.99(30) 1.92 @20°C(29) Log Kow 1.56-2.15(23,30) @25°C 2.13 (23,29, 30)

Table 4. Continued



Amount in Gasoline Research Octane Number (RON) Blending RVP (psi) Oxygen (W%) Taste Threshold in Water (ug/L) USEPA Drinking Water MCL California DHS Primary MCL Uses

1750 ug/L

1750 ug/L 1750 ug/L 700 ug/L

150 ug/L gasoline additive (4)

lug/L gasoline additive (4)

10,000 ug/L 10,000 ug/L 10,000 ug/L

700 ug/L

1,000 ug/L

5 ug/L

0 0 0

0

0

0 -500 (2)

3 psi (11)

3 psi (11)

3 psi (11)

1 psi (11)

(6)

(2)

3 psi (11)

123

up to 3%

p-Xylene o-Xylene m-Xylene Ethyl Benzene Benzene Toluene Properties Dimensionless 2.219E-01 (23,30) 2.428E-01 (23,30) 3.45E-01 (23,30) 3.139E-01 (23,30) 2.084E-01 (23,30) 3.139E-01 (23,30) Henry's Law 2.89E-01 0.22 (30) 3.83E-01 (23) Constant 25 (1,4,10, 29) 17(4) 25 (1,4,10,29) 15 (10,29) Flash Point (°C) -11(1,4) 4(1) 17.22 (10,29) 18(4) -11.11 (10,29) 4.4 (4, 29) 32 (l) 4.44 (10) 22 (l)


278 6. 7. 8.


9. 10.

11.

12. 13.

14. 15. 16. 17. 18. 19.

20.

21. 22. 23. 24.

Chevron Products Company, "Motor Gasolines Technical Review (FTR1)," 1996. Reynolds, R.E., et al, "Changes in Gasoline III," Downstream Alternatives, Inc., Bremen, IN, 1996. Datta, R., "Liquid-Phase Synthesis of Ethanol-Derived Mixed Tertiary Alkyl Ethyl Ethers in an Isothermal Integral Packed-Bed Reactor," Ind. Eng. Chem. Res. 1997, 36, 4586-4594. Datta, R., Worcester Polytechnic Institute, Worcester, MA, Personal Communication, February 2000. Daubert, T.E., et al, "Data Compilation Tables of Properties of Pure Compounds," Design Institute for Physical Property Data, American Institute of Chemical Engineers, New York, NY, 1985. Davidson, J.M., Alpine Environmental, Inc., "MTBE Properties & Use, Atmosphere & Precipitation, Sources & Pathways, Fate & Transport, Occurrence, Remediation, California Presentations," February 1996. Evans, T.W., et al, "Tertiary Alkyl Ethers, Preparation and Properties." Ind. Eng. Chem. 1936, 28, 1186-1188. Gibbs, L.M., Chevron Research and Technology, "Transportation Fuels Automotive Gasoline," Encyclopedia of Energy Technology and the Environment, John Wiley & Sons, Inc., 1995. Jokirinnr, Juha, Neste Canada Inc., Personal Communication and Company Webpage, http://www.neste.com/, March 1998. Kapplan, I., Global Geochemistry, Canoga Park, California, Personal Communication, March 1998. Lide, David R., "CRC Handbook of Chemistry and Physics, 81 Ed.," CRC Press, New York, NY, 2000-2001. Malcolm Pirnie, Inc., "Evaluation of the Fate and Transport of Methanol in the Environment," January 1999. Malcolm Pirnie, Inc., "Evaluation of the Fate and Transport of Ethanol in the Environment," November 1998. Mackay, D., et al, "Illustrated Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals, Volume III, Volatile Organic Chemicals," Lewis Publishers, Chelsea, MI, 1993. Office of Science and Technology Policy (OSTP), Executive Office of the President, National Science and Technology Council, Committee on Environment and Natural Resources, "Interagency Oxygenated Fuel Assessment," Washington, D.C., June 1997. Osinski, Mike, US EPA, "Water Quality Issues and MTBE," 10 Annual UST/LUST Conference, Long Beach, CA, March 1998. Schmidt, T.C., Swiss Federal Institute for Environmental Science and Technology, Personal Communication, April 2000. Squillace, P.J. et al, "Review of the Environmental Behavior and Fate of Methyl tert-Butyl Ether," Environ. Toxicol. Chem., 1997, 16, 1836-1844. Syracuse Research Corporation, "Environmental Fate Database," 2001, Syracuse, NY, http://esc.syrres.com/efdb.htm. st

th


279 25. US EPA, "Chemical Summary for Methyl-Tert-Butyl-Ether," EPA 749-F94-017a, August 1994. 26. US EPA, "Oxygenates in Water: Critical Information and Research Needs," EPA/600/R-98/048, December 1998. 27. Verschueren, K, "Handbook of Environmental Data on Organic Chemicals, 3 Edition" Van Nostrand Reinhold, New York, NY, 1996. 28. White, J., "Oxyinfo.doc," White Environmental Associates, Brea, CA, March 1991. 29. Yaws, Carl L., "Chemical Properties Handbook," McGraw-Hill, New York, NY, 1999. 30. Zogorski, J., et al, "Fuel Oxygenates and Water Quality: Current Understanding of Sources, Occurrence in Natural Waters, Environmental Behavior, Fate, and Significance," Interagency Oxygenated Fuel Assessment, Office Of Science and Technology Policy, Executive Office of the President, Washington, D.C., 1996.


rd


Appendix A - ACS Symposium Series (ACS Publications)

Recommend Documents