United States
             Environmental Protection
             Agency
             Environmental Sciences Research
             Laboratory
             Resewch Triangle Park NC 27711
EPA-600/3-79-040
April 1979
             Research and Development
&EPA
Effect of
Diethylhydroxyl-
amine on Smog
Chamber Irradiations

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                RESEARCH REPORTING SERIES

Research reports of the Office of Research and Development, U.S. Environmental
Protection Agency, have been grouped into nine series. These nine broad cate-
gories were established to facilitate further development and application of en-
vironmental technology.  Elimination  of traditional grouping was  consciously
planned to foster technology transfer and a maximum interface in related fields.
The nine series are:

      1.  Environmental  Health Effects Research
      2.  Environmental  Protection Technology
      3.  Ecological Research
      4.  Environmental  Monitoring
      5.  Socioeconomic Environmental Studies
      6.  Scientific and Technical Assessment Reports (STAR)
      7.  Interagency  Energy-Environment Research and Development
      8.  "Special" Reports
      9.  Miscellaneous Reports

This report has been assigned to the ECOLOGICAL RESEARCH series. This series
describes research on  the effects of pollution on humans, plant and animal spe-
cies, and materials. Problems are assessed  for their long- and short-term influ-
ences. Investigations include formation, transport, and pathway studies to deter-
mine the fate of pollutants and their effects. This work provides the technical basis
for setting standards to minimize undesirable changes in living organisms in the
aquatic, terrestrial, and atmospheric environments.
This document is available to the public through the National Technical Informa-
tion Service, Springfield, Virginia  22161.

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                                             EPA-600/3-79-040
                                             April 1979
       EFFECT OF DIETHYLHYDROXYLAMINE
        ON SMOG CHAMBER IRRADIATIONS
                     by

               Larry T. Cupitt
                Eric W. Corse

Environmental Science and Emissions Research
           Northrop Services, Inc.
        Environmental Sciences Center
            Post Office Box 12313
Research Triangle Park, North Carolina  27709
           Contract No. 68-02-2566



               Project Officer

             Joseph J. Bufalini

 Atmospheric Chemistry and Physics Division
 Environmental Sciences Research Laboratory
    U.S. Environmental Protection Agency
Research Triangle Park, North Carolina  27711
 ENVIRONMENTAL SCIENCES RESEARCH LABORATORY
     OFFICE OF RESEARCH AND DEVELOPMENT
    U.S. ENVIRONMENTAL PROTECTION AGENCY
RESEARCH TRIANGLE PARK, NORTH CAROLINA  27711

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                                   DISCLAIMER

     This report has been reviewed by the Environmental Sciences Research
Laboratory, U.S. Environmental Protection Agency, and approved for publica-
tion.  Approval does not signify that the contents necessarily reflect the
views and policies of the U.S. Environmental Protection Agency, nor does
mention of trade names or commercial products constitute endorsement or
recommendation for use.
                                      11

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                                  ABSTRACT

     The addition of diethylhydroxylamine (DEHA) to the urban atmosphere had
been suggested as a means of preventing photochemical smog.  Smog chamber
studies were carried out to investigate the photochemical smog formation
characteristics of irradiated hydrocarbon-nitrogen oxides - DEHA mixtures.
Propylene and n-butane were the hydrocarbons used.  The effects of DEHA
upon ozone formation, aerosol formation, peroxyacetyl nitrate formation,
nitric oxide-to-NO  conversion, and hydrocarbon consumed are described.  The
                  X
rate constant for the reaction
                           DEHA + OH     products

was estimated as 4.1 + 3.4 X 10  ppm  min  .  Possible reaction schemes for
DEHA in the photochemical smog mechanism are discussed.
     The addition of DEHA to a HC/NO  system inhibits the conversion of NO
                                    X
to NO^ during the initial minutes of irradiation, but after continued
irradiation accelerates this conversion.
     This report is submitted in fulfillment of Contract No. 68-02-2566 by
Northrop Services, Inc., under the sponsorship of the U.S. Environmental
Protection Agency.  This work covers a period from November, 1976 to December,
1977, and work was completed as of May 1978.
                                      iii

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                                   CONTENTS
Abstract	'<	    iii
Figures	:	     vi
Tables	     ix
Abbreviations and Symbols	      x
Acknowledgments	    xii

     1.  Introduction	      1
                                       i
     2.  Experimental	      2
     3.  Results	      5
     4.  Discussion	     26
               DEHA Effects on Aspects  of Smog Formation	     26
               Potential Mechanisms to  Explain DEHA Effects on Smog
                 Formation	     31
     5.  Conclusions	     36

References	     38
Appendix	     40

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                                   FIGURES
Number
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15

Schematic diagram of chamber and. support equipment ....
Reaction profiles of DEHA-NO system 	
Reaction profiles of 0.25 ppm propylene-NO system ....
X
Reaction profiles of ~0.25 ppm propylene-NO -DEHA system .
Reaction profiles of 0.5 ppm propylene-NO system 	
Reaction profiles of ~0.5 ppm propylene-NO -DEHA system
X
Reaction profiles of 5.0 ppm propylene-NO system ....
X
Reaction profiles of ~5 ppm propylene-NO -DEHA system. . .
X
Reaction profiles of ~0.5 ppm n-butane-NO system ....
X
Reaction profiles of ~0.5 ppm n-butane-NO -DEHA system . .
X
Reaction profiles of 5.0 ppm n-butane-NO system 	
Reaction profiles of ~5 ppm n-butane-NO -DEHA system . . .
X
Reaction profiles of ~15 ppm n-butane-NO system 	
X
Reaction profiles of 15.0 ppm n-butane-NO -DEHA system . .
X
Effect of changes of [DEHA] o/ [HC] 0 on manifestations of
Page
... 3
... 8
... 9
... 10
... 11
... 12
... 13
... 14
... 15
... 16
... 17
... 18
... 19
... 20

          "smog" for an initial HC concentration of ~0.25
          ppm propylene	22

16      "Smog" manifestations for an initial HC concentration of
          ~0.5 ppm propylene		23

17      Effect of [DEHA]0/[HC]0 on "smog"  manifestations  for an
          initial HC concentration of ~5 ppm propylene	24

18      Aerosol formation data versus time for runs with  and
          without DEHA	25
                                     VI

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Number
19
20
A-l
A- 2
A- 3
A- 4
A- 5
A- 6
A- 7
A- 8
A- 9
A- 10
A- 11
A- 12
A- 13
A- 14
A- 15
A- 16
A- 17
A- 18
A- 19
A- 20
A-21
A- 22
A-23


Simulation profiles for HC, NO, N0_, 0 , and DEHA predicted

X
Reaction profiles of 0. 25 ppm propylene-NO system 	
X
Reaction profiles of 0. 25 ppm propylene— NO system 	
X
Reaction profiles of 0. 24 ppm propylene— NO —DEHA system. . .
X
Reaction profiles of 0. 26 ppm propylene— NO —DEHA system.
Reaction profiles of 0. 30 ppm propylene— NO -DEHA system. . .
X
Reaction profiles of 0. 30 ppm propylene-NO —DEHA system. . .
Reaction profiles of 0.49 ppm propylene— NO system 	
X
Reaction profiles of 0.48 ppm propylene— NO system 	
X
Reaction profiles of 0. 50 ppm propylene^NO system . * . . *
X
Reaction profiles of 0.60 ppm propylene-NO -DEHA system . .
Reaction profiles of 0. 50 ppm propylene-NO -DEHA system . .
Reaction profiles of 0. 54 ppm propylene— NO system 	
Reaction profiles of 0.47 ppm propylene— NO system 	
X
Reaction profiles of 0.50 ppm propylene-NO —DEHA system. . .
X
Reaction profiles of 0. 54 ppm propylene— NO system 	
X
Reaction profiles of 0. 55 ppm propylene-NO system 	
X
Reaction profiles of 0. 54 ppm propylene-NO —DEHA system. . .
X
Reaction profiles of 0.47 ppm propylene-NO system 	
Reaction profiles of 0. 52 ppm propylene-NO system 	
Reaction profiles of 0. 52 ppm propylene-NO system 	
X
Reaction profiles of 0. 50 ppm propylene-NO system 	
X
Reaction profiles of 0.55 ppm propylene-NO -DEHA system. . .
. Page
. . 32
. . 34
. . 41
. . 42
. . 43
. . 44
. . 45
. . 46
. . 47
. . 48
. . 49
. . 50
. . 51
. . 52
. . 53
. . 54
. . 55
. . 56
. . 57
. . 58
. . 59
. . '60
. . 61
. . 62
. . 63
VI1

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Number
A- 24
A-25
A- 26
A- 27
A- 28
A- 29
A- 30
A- 31
A- 32
A- 33
A- 34
A- 35
A- 36
A- 37
A- 38
A- 39
A-40
A- 41
A- 42
A- 43
A- 44
A- 45
A- 46
A-47

Reaction profiles of 5.0 ppm propylene-NO system 	
X
Reaction profiles of 5.2 ppm propylene-NO system 	
X
Reaction profiles of 5.1 ppm propylene-NO system 	
X
Reaction profiles of 5.3 ppm propylene-NO -DEHA system . . .
X
Reaction profiles of 4.7 ppm propylene-NO -DEHA system . . .
X
Reaction profiles of 4.9 ppm propylene-NO -DEHA system . . .
Reaction profiles of 5.0 ppm propylene-NO -DEHA system . . .
X
Reaction profiles of 4.7 ppm propylene-NO -DEHA system . . .
Reaction profiles of 0.49 ppm n-butane-NO system 	
X
Reaction profiles of 0.59 ppm n-butane-NO system 	
Reaction profiles of 0.48 ppm n-butane-NO system. 	
Reaction profiles of 0.46 ppm n-butane-NO -DEHA system . . .
X
Reaction profiles of 0. 55 ppm n-butane-NO -DEHA system . . .
X
Reaction profiles of 0. 59 ppm n-butane-NO -DEHA system . . .
Reaction profiles of 4.9 ppm n-butane-NO system 	
Reaction profiles of 4.9 ppm n-butane-NO system 	
X
Reaction profiles of 4.3 ppm n-butane-NO -DEHA system . . .
Reaction profiles of 4.7 ppm n-butane-NO -DEHA system . . .
X
Reaction profiles of 4.8 ppm n-butane-NO -DEHA system. . . .
Reaction profiles of 14.0 ppm n-butane-NO system 	
X
Reaction profiles of 14.3 ppm n-butane-NO system 	
Reaction profiles of 13.6 ppm n-butane-NO -DEHA system . . .
X
Reaction profiles of 13.5 ppm n-butane-NO -DEHA system . . .
X
Reaction profiles of NO system 	
Page
64
65
66
67
68
69
70
71
72
73
74
75
76
77
78
79
80
81
82
83
84
85
86
87
Vill

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                                     TABLES

Number                                                                   Page

  1      Results of Irradiation of HC/NO /DEHA Mixture Using
           Propylene	     21
                                      IX

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                           ABBREVIATIONS AND SYMBOLS
ABBREVIATIONS
approx.      — approximately
ARB          — Aerosol Research Branch
°C           — degree Celsius
cm           — centimeter
DVM          — digital voltmeter
EAA          — electrical aerosol analyzer
EPA          — U.S. Environmental Protection Agency
ERC          — Environmental Research Center
°F           — degree Fahrenheit
FID          — flame ionization detection
ft           — foot
FTIR         — Fourier transform infrared spectroscopy
GC           — gas chromatograph
hr           — hour
in           — inch
IR           — infrared
1            — liter
MCA          — multichannel analyzer
pm           — micrometer
min          — minute
MS           — mass spectrometer
NBS          — National Bureau of Standards
NSI          — Northrop Services, Inc.
OPC          — optical particle counter
ppb          — part per billion
ppm          — part per million

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RTP
sec
SYMBOLS
CH3CHO
C2H4
C2H5°H
C3H6
C4H10
DEHA
DENO
HC
HONO
  2
H2

NO
N02
NO
  x
N2
N2°
0
OH
°2
°3
PAN
THC
Research Triangle Park, North Carolina
second
acetaldehyde (ALD2) (C2H 0)
nitroe thane
ethylene
ethyl nitrite (NET) (nitroethane)
ethanol
ethyl nitrate (NIT)
propylene
n-butane
diethylhydroxylamine
(C2H5)2-N-0.
hydrocarbon
nitric acid
nitrous acid
hydroperoxide
hydrogen
water
nitric oxide
nitrogen dioxide
nitrogen oxides
nitrogen
nitrous oxide (N2O)
atomic oxygen
hydroxyl radical
oxygen
ozone
peroxyacetyl nitrate
total hydrocarbons
k       first-order dissociation constant for NO_
[OH]    steady-state hydroxyl radical concentration
    S 5
                                      XI

-------
                                 ACKNOWLEDGMENTS

     The authors especially thank Dr. T. A. Walter for his helpful discussions
of reaction mechanisms and intermediates.  We also thank Mr. T. Winfield  (for
assistance in analyzing for nitric acid), Mr. S. B. Joshi  (for help  in deter-
mining peroxyacetyl nitrate concentrations), and Mr. B. Gay and Dr.  T. Knudsen
(for aid in analysis of diethylhydroxylamine).
                                     XII

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                                   SECTION 1
                                 INTRODUCTION
     The idea of treating polluted air with a chemical "air freshener" has
been bandied about in the literature for a number of years (1).   The quest
for a "suitable" free radical scavenger led Heicklen and others to suggest
the use of DEHA as a photochemical smog inhibitor (2,3).  Because of the
announced intention of Heicklen and co-workers "to add DEHA into urban atmo-
spheres to prevent the formation of photochemical smog" (4),  and in an attempt
to resolve the controversy (5,6) regarding the efficacy of DEHA in inhibiting
the onset of the physical and chemical characteristics associated with smog
formation, this study was undertaken.

-------
                                   SECTION 2
                                 EXPERIMENTAL
     A series of irradiation experiments was conducted in a smog chamber using


propylene (C H ) or n-butane (C H  )  as the HC.  NO  in the ratio 4 parts NO
            J O                ^* Aw                X

to 1 part NO  were added to the chamber, and DEHA was either introduced or ex-


cluded in order to ascertain what differences were attributable to the role of


the inhibitor.





     The irradiations were carried out in a 400-ft  smog chamber described


elsewhere (7).  A schematic diagram of the chamber and support equipment is


shown in Figure 1.  An average value for k.. of 0.4 min   was measured.




                                                                       ®
     Cylinders of NO in nitrogen (N») and N0? in N_ from Scott Products  were


used to charge the chamber with the initial NO  concentrations.  Propylene and

                                              x                    ®
n-butane used for these runs were supplied by Matheson Gas Products .  An-

                                      ®
hydrous DEHA from Pennwalt Corporation  was used.  Initially, DEHA was purified


by vacuum distillation  (4).  However, this purification was discontinued for


two reasons:   (1) no difference in irradiations was attributable to use of the


purified material; and  (2) any widespread application of DEHA to smog control


strategies would have to use unpurified commercial product.
     NO and NO  concentrations were monitored on two Bendix  chemiluminescent
              x

monitors.  Periodic Saltzman determinations  (8) of N0_ concentration were

                                  ®
made.  0  was measured on a Bendix  Model 8002 0_ monitor.  HC concentrations

                                                                   ®
were measured using an FID gas chromatograph  (either a Perkin Elmer  Model 900

                     ®                ®
or a modified Beckman  6800).  Porapak  Q columns were used to separate and

                                                                     ®
analyze the HC.  DEHA in the gas phase was monitored using a Pennwalt  223

-------
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-------
amine packing in either a glass or Teflon  column in the Perkin Elmer  Model


900 GC.  Bag samples from the chamber were analyzed for peroxyacetyl nitrate

                         ®
(PAN) on the Perkin Elmer  GC with an electron capture detector.  Aerosol

                                             ®
formation was monitored with a Thermo Systems  EAA.  The dew point for each

                                                              ®
run was held between 52-56°F and was monitored with an E G & G  dew point

                                                                      ®
hygrometer.  The internal chamber temperature was monitored with a YSI


calibrated thermistor.

-------
                                   SECTION 3
                                    RESULTS
     The reaction profiles for 47 HC/NO /DEHA runs are displayed in the Appendix.
                                       X.
For convenience, selected runs will also be reproduced in the present section.
For all of the runs reported here, the nominal initial concentrations of NO
and NO were 100 and 400 ppb, respectively.  Stability measurements of DEHA and
HC gave gas-phase loss rates in the nonirradiated chamber that were experi-
mentally equivalent to the dilution losses.

     Figure 2 shows the results of irradiating DEHA and NO ,  with no HC added.
Conversion of NO to N0_ was inhibited for about 6 hr, after which rapid con-
version of NO and quick formation of 0  occurred.

     Figures 3 through 14 show the effects of irradiations with and without
DEHA for a variety of HC concentrations.  In Figures 3 and 4, the propylene
concentration is ~0.25 ppm.  In Figures 5 and 6, the propylene concentration
is ~0.5 ppm, and in Figures 7 and 8 the HC concentration is ~5 ppm.  Figures
9 through 14 show irradiations of n-butane.  HC concentration in Figures 9
and 10 is ~0.5 ppm; in Figures 11 and 12, ~5 ppm; and in Figures 13 and 14,
~15 ppm.

     These graphs of irradiation runs demonstrate strikingly the effects of
DEHA on the system.  During the initial portion of the run, the NO concentra-
tion increases as the NO_ is converted to NO and atomic oxygen (0) by irradia-
tion.  HC consumption is decreased relative to the "no DEHA" profile, and O
formation is retarded.  After the DEHA is consumed, the reaction proceeds with

-------
vigor!  The NO conversion is very rapid, 0_ formation is accelerated, and the
maximum 0  concentration attained is increased.

     Table 1 shows data taken from propylene runs.  The first column lists the
Appendix figure number (e.g., "1" refers to Figure A-l).  The second column
gives the initial propylene concentration, the third column tabulates the ini-
tial DEHA concentration,  and the fourth shows the ratio [DEHA]0/[HC]0.  The
next six columns represent various measurements of "smog formation."  The time
to reach 90% of initial NO concentration  (i.e., 10% conversion to NO  and other
products) is listed in minutes in column five.  The time at which only 10% of
[NO]0 remains as NO is given in the next column.  The times in minutes for 0
to reach 40 ppb and to reach its maximum concentration are listed in the next
two columns, while the maximum O  concentration obtained is given in column
nine.  The effective O  dosage for "1 day" (i.e., 11 hr of chamber irradia-
tion) is given in the tenth column.
     The next five columns list pseudo-first-order rate constants for HC or
DEHA removal.   (This assumes that concentrations of reactants other than HC or
DEHA are unchanging; i.e., that steady-state approximations are valid for
those species which react to remove the HC or DEHA.)  The first two of these
columns apply only to irradiations to which no DEHA has been added.  The first
column shows the rate constant calculated from data early in the reaction
(i.e., prior to a substantial 0  buildup), while the second column lists the
overall removal rate constant.  The third column tabulates the HC removal rate
when DEHA was present, and the fourth gives the HC removal rate after the DEHA
has been consumed.  Finally, the pseudo-first-order removal rate constant for
DEHA plus hydroxyl  (OH) is estimated.

     Figures 15 through 17 plot some of the data on "smog formation" listed in
Table 1 for the initial propylene concentrations of ~0.25, ~0.5, and ~5 ppm,
respectively.  Figure 15 demonstrates some interesting results.  At  [DEHA]0/[HC],
= 0.2, the initial conversion of NO to NO  is retarded; once the reaction
                                         X
begins, however, the 90% conversion point (the + in the plot) is soon reached
and is achieved earlier than in the no-DEHA case.  Therefore, under these
experimental conditions "smog formation" can be either retarded or enhanced,

                                       6

-------
depending upon which characteristic one chooses to examine.  Note also that,
while the onset of 0  production may be retarded, it is entirely possible that
the "1-day" 0  dosage may be enhanced.  Comparison of Figure 15 with Table 1
shows that, while the "1-day" O  dosage is reduced at high DEHA-to-HC ratios,
it comes about not because the potential for large values of [0_]    is reduced,
                                                               3 max
but rather because the onset of 0  formation is delayed sufficiently long for
the integrated 0 -time profile for the first 11 hr of irradiation to be di-
minished.
     Figures 5 and 6 demonstrate that PAN production seems to be increased
when DEHA is added to the system.  Also, Figure 8 includes the profile of HNO.
formation as monitored by the method of Miller and Spicer  (9).

                                                                      ®
     Aerosol formation was monitored in a series of runs using the TSI  Model
3030 EAA.  Figure 18 compares the aerosol data for some 5 ppm propylene runs,
with and without DEHA.

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CD
                      60    I2O   ISO    240   30O
                                                360   420   48O    S4O
                                                     1IME . minulei
                                                                            66O   72O   780   840    9OO
                 Figure  2.  Reaction profiles of DEHA-NO  system.

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0.9
0.8-
O.7-
             120    180    240   300  360   42O    -»8O   54O   6OO   66O   72O    780   84O
        60
                                   TIME, minules
   Figure 3.   Reaction profiles  of 0.25 ppm  propylene-NO   system.
                                                                X

-------
 I.OH
O.9
o.a
0.7
O.6
        60    I2O   ISO
                       240    3OO   560   42O
                          TIME,  minutes
                                            4BO   S40   CUO
   Figure 4.  Reaction profiles  of ~0.25 ppm propylene-NO -DEHA system.

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0.6
        60
                  I8O   24O    3OO
                    TIME, minutes
                                  360
                                       42O   480   540    6OO   66O
   Figure 5.  Reaction profiles  of 0.5 ppm propylene-NO   system.

-------
to
             O.9-
             0.8-
             0.7-
             0-6-
             0.5-
             O.4-
             0.3-
             0.2-
             0.1-
                                          30O    J6O   42O
                                           TIME . minutet
                                                           4BO   540    6OO   66O   72O    780
                Figure 6.   Reaction profiles  of ~0.5  ppm propylene-NO  -DEHA system.

-------
  6.0-
  S.O-
a
  3.0-
  2.0-
  1.0-
   0 J
           O 30 60 9O 120
               TIMC.minutet
           Figure 7.  Reaction profiles  of 5.0 ppm propylene-NO   system.

-------
6.O H
5.0
4.O-
3.0-
2.O-
I.O-
 O-J
       O.9-
       O.8-
       O.7-
       O.6
 0   NO,
 Id   NO
 4   Oj
 V   Propylene
 O   OtHA
I	1 Sulumon
 M   HNOj , micro CCKllomeliy


              NO.
                                                   TIME, minutes
          Figure  8.   Reaction profiles  of ~5  ppm  propylene-NO -DEHA system.

-------
0.6-J,
0.5
O.I -
        6O    120    ISO    240   300   36O    42O   48O   54O   6OO    660    72O   780    840   900   9CO   IO?O   lOUO   1140   1200
                                      TIME, imnules
   Figure  9.  Reaction profiles  of ~0.5 ppm n-butane-NO  system.

-------
0.9
                                                                                      IOZO   1080   I HO
                                      TIME, minulei
   Figure 10.  Reaction profiles of ~0.5 ppm n-butane-NO -DEHA  system.
                                                            X

-------
b.O-
3.0-
Z .0-
1.0-
 O J
      o.a
         o    eo
                                                         600   6OO
         Figure 11.   Reaction profiles of 5.0 ppm n-butane-NO  system.
                                                                X

-------
              1.0
             O.9-
00
      6.O-
      5.0-
      4.O .
      3.0 -
      2.O-
       1.0-
                     60
                                                                                                           I02O   1080   1140
                                                   TIME, minute*
                Figure  12.   Reaction profiles  of ~5 ppm n-butane-NO -DEHA system.

-------
  15.0-


  14.0-


  I3.O-



  12.0-


  11.0-


  IO.O-


  9.O-


f 8.0-




E

S 6.O-


  5.O-


  4.O-



  3.0-


  Z.O-


  I .O-
         0.9 -
         O.8-
                  6O
                       120    I8O    24O

                           TIME, minutes
                                         300   360
            Figure  13.   Reaction profiles of ~15 ppm n-butane-NO   system.
                                                                           X

-------
          1.0-
          0.9-
  16.0
  15.0-
  14.0-
  13.0-
  12.0-
  I I.O-
  10.0-
• 9.O-
| 8.0-
" 7.0-
a. 6.0-
  5.O-
  4.0-
  3.0-
  2.0-
   1.0-
    0-J
                  60    120    180    240   300    360   42O   48O   54O    6OO
            Figure 14.   Reaction profiles of  15.0  ppm  n-butane-NO -DEHA  system.

-------
TABLE
                               1.  RESULTS OF  IRRADIATION OF HC/NO /DEHA MIXTURE USING PROPYLENE
                                                                      X
K>


FICIJRE
1
2
3
4
5
6
7
10
13
21
22
11
23
12
15
25
26
27
28
29
30
31

"*••'<>
ppn
0.0
0.25
0.25
0.24
0.26
0.30
0.30
0.50
0.54
0.52
0.50
0.60
0.55
0.50
0.50
5.2
5.1
5.3
4.7
4.9
5.0
4.7

'Z'°
0.19
0.00
0.00
0.05
0.10
0.15
0.38
0.00
0.00
0.00
o.'oo
0.13
0.13
0.13
0.15
0.00
0.00
6.23
0.28
0.50
0.76
1.4

|DHIAI0
|ICI0
0.00
0.00
0.21
0.38
0.50
1.27
0.00
0.00
0.00
0.00
0.21
0.23
0.25
0.30
0.00
0.00
0.04
0.06
0.10
0.15
0.30
TIME FOR
0.9|NO]0
miji
380
25
25
46
274
253
474
14
8
8
11
191
226
168
215
2
1
45
42
85
175
310
o.]|iwi0
min
418
165
171
83
288
268
495
93
60
77
67
208
267
194
237
9
9
80
C5
132
245
353-
Ozone
= 40 ppb lOjIj^
mi n min
400
165
165
75
28R
266
495
81
55
64
67
204
252
189
234
R
7
115
125
ISO
300
402
840
750
780
480
900
660
930
430
405
360
340
*
715
-510
600
23
20
750
840
R40
990
1150
ppb
700
230
260
540
800
750
900
525
470
590
570
*
810
>700
630
330
320
760
760
740
700
800
"ONE
DAY"
1C Remwal
O3 Ozone UU1A
DOSAGE S70 ppb Overall Present
^m— nun min n\in nun
117
85
82
243
194
223
60
241
236
294
279
*
240
>253
213
22
23
245
255
183
98
65
.00655 .00655
.00550 .00550
.00513
— — .00134
.00151
— .00072
.00564 .00700
.00853 .01006
.00735 .00900
.00501 .00842
— — .00255
. 00094
— — . 00024
— — .00102
.00763
.00749
.00239
.00073
.00114
.00026
.00071

DEI [A
Consumed
min"1
-
—
.02-163
.02267
.01337
—
	
—
—
—
.02472
.02041
. 03047
.02387
—
—
.00773
.00822
.00555
.00545
.00298


^EHA
min 10 pun" min
-
—
.04748
.0)008
.01103
.00453
	
	
	
—
.00957
.00669
.00946
.00871
	
	
.01037
.01163
.OH947
.00446
.00931
-
	
3.3
2.7
2.6
2.3
	
	
	
	
1.4
2.6
14. 2
3.1
	
	
1.6
5.7
3.0
6.2
4.7
                *F/-|uipment Failure During Run

-------
             I 
-------
o — [NO] = o.

.30-
.28-
.26-
.24-
.22-
.20-
.18-
.16-
o
r~~l 1 4-
o -ln
I
.12-
.10-
.08-
.06-
.04-
.02-
0-
(
+ - [NO] = o.
w D — [ 0 3] = 4C
ME& w
X — "ONE DAY

HC = 0.5 ppm
°» X
oXOf










^o — m Y
) 100 200 300 400 500
MINUTES
                                                                 ppb
                                                          "ONE DAY" 03 DOSAGE IN ppm-minutes
Figure 16.   "Smog" manifestations  for an initial HC concentration of ~0.5 ppm
             propylene.
                                        23

-------
                                                   +   n
                                              D
                                                           O -[NO] = 0.9[NO]0
                                                           + -[NO] = o.i [NO]O
                                                           D - [ 03] - 40 ppb
                                                           X - "ONE DAY" 03 DOSAGE IN ppm-minules
                                                           HC- 5 ppm Propylene
1
100
1
200
300
t
400
500
                             MINUTES or ppm-minutes
Figure  17.  Effect of  [DEHA]0/[HC]0  on "smog"  manifestations for an initial
             HC  concentration of ~5 ppm propylene.
                                          24

-------
to
U1
       250-
          S      NMO )
              5O
       200-
       100-
        0J
              45
              40-
              30-
            O 25-
              20-
              10-
                                                                           SOLIO POINTS — NO OFHA
                                                                           OPEN POINTS — OIHA AODEO
                                                                                 ISO    20O    220    24O    26O    280     3OO
                                                               MINUTES
     Figure  18.  Aerosol formation  data versus time for  runs with (open  symbols)  and without  (filled  symbols)
                  DEHA.

-------
                                   SECTION 4
                                  DISCUSSION
DEHA EFFECTS ON ASPECTS OF SMOG FORMATION

     The results reported above illustrate that DEHA does indeed exhibit re-
markable influence on the progress of smog formation in chamber irradiations.
The effect of DEHA on a number of characteristics normally attributed to smog
formation will be discussed below.

NO Conversion

     One of the earliest suggestions for using DEHA as an inhibiting agent
arose because of its ability to inhibit conversion of NO to N0_ (2).  A series
of 10-min irradiations of NO/C,H./O0 were carried out, and the amount of N00
                              j b  ^                                       £.
formed was monitored.  DEHA was found to be one of the more efficient com-
pounds for retarding the formation of NO .  The data presented herein confirm
that result:  DEHA does inhibit the conversion of NO to NO  products.  Indeed,
in this system, N0? initially decreases while NO increases.  But 10-min irradia-
tions do not tell the whole story, for — in all but the most reactive HC/NO
systems — the addition of DEHA first inhibits and then accelerates the con-
version of NO.  As can be seen from Table 1, experimental conditions can be
found for which conversion of the first 10% of NO is retarded while conversion
of 90% of the NO is accelerated.  (See also Figures 9 and 10 for the 0.5 ppm
n-butane runs and Figures 11 and 12 for the 15 ppm n-butane runs,  where the
DEHA-added runs exhibit similar behavior.)  This means that the effect of DEHA
in inhibiting NO conversion to products is ambiguous, and that short irradia-
tion experiments could show an inhibiting effect, while longer irradiations
would indicate an enhancement.
                                      26

-------
03 Formation
     The data in Table 1 and the reaction profiles in the Appendix all show
[0,]    to be increased by the addition of DEHA to the reaction system.  With
  3 max
DEHA added to the propylene system,  [0_]    «750 ppb.  This compares to
                                      3 max
~250 ppb, ~550 ppb, and ~330 ppb for the 0.25 ppm, 0.5 ppm, and 5.0 ppm
propylene runs, respectively.
     In fairly reactive.systems, the onset of 0  production  (as represented by
the time at which the O  concentration reaches 40 ppb) and the time for 0
maximum are retarded by DEHA.  However, in the case illustrated by Figure A-4,
both onset of 0_ formation and the time for  [O_]    are advanced by the addi-
               3                              3 max
tion of DEHA.  Coupled with an increased value for the O  maximum, the "1-day"
0  dosage is three times as large with 50 ppb of DEHA in the system as with no
DEHA.
     0  dosages were determined by measuring the area under the 0  concentra-
tion profile for the first 11 hr of irradiation.  Schere and Demerjian  (10)
give 1/2-hr average values of k  for June 21 in Los Angeles.   In our experi-
ments, the area under the sinusoidal-like step function was calculated  to  give
a k 'time product.  The result was divided by the chamber k  value of 0.4  to
determine the length of time of chamber  irradiation equivalent to the Schere
and Demerjian k  profile.  This time was reduced by about 10%  to represent the
solar irradiance on an average spring or summer day instead of for the  longest
day of the year.   (Data taken from Leighton  (11) for a point at 35°N latitude
indicate that daily insolation for an average spring and summer day is  about
89% of the daily insolation at summer solstice.)  The result was that an 11-hr
irradiation in the chamber gave a k  •time product equivalent to that of an
average spring/summer day in Los Angeles; the integrated dosages for 11-hr
irradiations are given in Table 1 and Figures 15 through 17.
      In general,  the  time  for  onset  of  0  production  and the  time  to reach 0
                                        •J                                    J
maximum increase  with increasing  DEHA concentration.   This  affects the "1-day"
dosage figures, not by reducing the  0 -forming potential of the system but
                                      27

-------
rather by moving the O  profile out of the first 11-hr irradiation period.
Even so, the dosage figures are not lowered relative to the no-DEHA case until
a substantial amount of DEHA has been added.
PAN Formation

     The addition of DEHA to the propylene-NO  system roughly doubles the
maximum PAN concentration reached during irradiation (cf. Figures 5 and 6).
A similar result is reported by Pitts et al.  (5).

Aerosol Formation

     Figure 18 compares the aerosol growth dynamics of chamber irradiations
with and without DEHA.  In both instances, the rapid production of aerosol
coincides with the onset of O  formation.  Without DEHA, a large number of
small droplets is formed.  With DEHA in  the  system, the  number of particles
formed is not so large as in the "no-DEHA" case, but they are larger in diame-
ter (as evident in the substantial increases in volume and surface area).  This
means that there is considerably more material tied up in the aerosol when DEHA
is in the system.  Also, only with DEHA added do the aerosol particles exceed
0.05 ym in diameter.  Since 0.05 ym is (roughly) the smallest size particle
that can contribute to particulate light scattering (12), the net effect of
DEHA on visibility would seem to be increased degradation resulting from
particulate diffusion.

HC Consumption

     A second major inhibiting characteristic (in addition to retarding NO
conversion) ascribed to DEHA is that it slows the rate of HC consumption
(4,6).  This is to be expected of any compound which can effectively compete
with the HC for those reactive species which are capable of removing the HC.
Because the predominant reactive species early in an irradiation is OH  (12),
any compound which reacts with OH at a rate substantially higher than that of
the HC should effect a decrease in the HC consumption rate — so long as its
reaction products do not in turn produce even more OH or other reactive species.

                                     28

-------
     Table 1 shows that DEHA does substantially reduce the HC consumption rate
as long as DEHA is present in the chamber.  Once all the DEHA has been consumed,
however, the HC removal rate is accelerated and becomes as fast or faster than
the removal rate in the "no-DEHA" case.

     Figures 9 through 14 demonstrate a similar general behavior for n-butane
(i.e., the HC removal rate is decreased as long as DEHA is present and is
increased after all the DEHA has been consumed).

     The data listed in Table 1 for K „       , permit some interesting cal-
                                     HC Removal                       ^
culations.  If one assumes that HC removal prior to substantial buildup of O
is primarily due to reaction with OH (12), then the steady-state hydroxyl
radical concentration  [OH]   can be estimated as
                          ss

                   COHl   =  (k            - k        ) /k
                       ss     HC Removal    Dilution ' HC+OH

Using the data for k            (with 0  ^ 70 ppb) together with values of 2.6
    -4    -1             4    -1    -1
x 10   min   and 3.6 x 10  ppm   min   for k_._  .   and k       (13), one
                                            Dilution      HC+OH
calculates an average OH concentration of 1.6 x 10   ppm, or about 4 x 10
radicals cm  .  This value is roughly equivalent to the yearly daytime average
[OH] of 5 x 10  radicals cm   calculated  by Weinstock  (14) , and is less than
the daytime OH concentrations in ambient  air measured by Niki et al.  (15).
     The validity of using HC removal rate data taken before  [O  ] reaches 70 ppb
can be checked by calculating the ratio of HC removed by OH to the HC removed
by 03:

                              _kHC+OH
                                 kHC+03  [O  ]  [HC]
For  the propylene data given  in Table  1,  the ratio  is:
                            4    -1    -1           -7
                   (3.8 x  10 ppm   min  )  (1.6 x  10   ppm)    _  .
              R	—	—	—	 ~  5.1
                     (1.7  x  10   ppm   min  )  (0.070 ppm)
                                       29

-------
This means that the HC removal rate is dominated (by a ratio of 5:1 or greater)
by the OH reaction until 0  exceeds 70 ppb.  This calculation neglects HC
removal by other species like hydroperoxide  (HO.) and 0, the concentrations of
which are kept exceedingly low by other species present in the system.
     One may assume that when both DEHA and propylene are present in the
chamber they compete for the same reactive species.  If that species is OH,
then one may estimate the reaction rate constant for DEHA plus OH by the
following equation:,

                                 k            *k
                               _  DEHA Removal  HC + OH
                     DEHA + OH   k
                                  HC Removal (DEHA Present)
The last column in Table 1 shows the estimated values for DEHA + OH determined
from the experimental runs.  The results give a value of 4.1 x 10   (±3.4 x 10 )
ppm   min  .  This value is in good agreement with the direct measurement of
1.4 x 10  ppm   min   reported by Gorse et al. (16), especially in view of the
assumptions required to obtain the estimate.  This value is approximately one-
half the "hard-sphere" estimate for a collisional rate constant and implies
that the reaction of DEHA with OH is very efficient.
     The data show that the parent compound DEHA can act to inhibit many of the
manifestations of smog formation.  However, as Figure 2 illustrates, DEHA is
an organic molecule which, when irradiated with NO , yields reactive products.
                                                  X
These primary or secondary products may, in turn, rapidly convert NO to NO? and
form copious quantities of 0 .   This implies that the "reactivity" of DEHA
itself may set the limit on the extent of inhibition which is attainable by
injection of DEHA into the atmosphere.  Indeed, the striking similarity of
Figure 2 (DEHA alone) and Figure 10 (DEHA added to 0.5 ppm n-butane) supports
the idea that, in reasonably unreactive systems, smog formation is directly
controlled by the reactivity of the DEHA itself.
                                     30

-------
POTENTIAL MECHANISMS TO EXPLAIN DEHA EFFECTS ON SMOG FORMATION

     The behavior of the chamber runs described above can be explained in
general terms by assuming that DEHA interacts with OH and other reactive
intermediates to form inert or less reactive products.   (Indeed, the primary
applications for DEHA suggested by the manufacturer, Pennwalt, are as a radical
scavenger or "shortstopper" in polymerization or corrosion chemistry  (17).)
Radical scavenging by DEHA would:  (1) reduce the number of radicals capable
of reacting with HC, thus reducing the HC removal rate; and  (2) intercept
atomic 0 so that irradiation would convert the NO- to NO with subsequent
suppression of 0  formation.

     Attempts were made to adapt a reaction model for a propylene-NO  system
                                                                    X
developed by Dodge and Ascher  (private communication) to explain the results
described above.  Reactions for DEHA were added to the mechanism, based upon
reported product formation.
     The products attributed by Heicklen  (4) to addition of DEHA to a C_H /NO/
0_ irradiation system are:  acetaldehyde  (CH CHO)  (C?H 0)  (ALD2), ethyl nitrite
 (C H NO )  (NET), ethyl nitrate  (C H ONO )  (NIT), ethanol  (C H OH), nitrous
acid  (HONO), and nitrous oxide  (NO)  (N20).  The reaction of O  with DEHA  (in
the presence of excess O  or air) is  reported to yield CH CHO and C»H NO?
essentially quantitatively and without inhibition  (18).
     One possible mechanism that explains all of the observed products  is
shown in Figure 19.  The first reaction step, abstraction of the hydroxyl
hydrogen, was suggested by Heicklen  (4) and supported by Gorse e~b at.  (16),
based upon liquid phase kinetic studies.  Abstraction reactions are often  very
fast; in the case of abstraction by OH, a very stable product, water  (H_O), is
formed.  The resulting radical,  (C2H  ) -N-0* or DENO, is interesting  in that
resonant configurations may place  the  free electron on either the O or  N atom.
The intermediate DENO or some subsequent product may itself be relatively
unreactive, since the rapid conversion of NO  (and the other manifestations of
smog formation) is  suppressed so long  as DEHA is still present in the chamber.
                                      31

-------
u>
NJ
RO
o ;
°3 r
DEHA OH ^
N02^
HONO^
H * OWJBS^^
H C-C — N — Et •*** — ~ y
> /
H,C-C— N-Et Et-N0-+Et
O ii i
II INO
Vv 4
/ \ EtO-
CH CHOA Et-NO
•D
+ H
EtN02 H^-C-O-O-
H^ r~ * LI r* _ P 1
•a v< — ^ — ^ rl-aVy o v. '
\ ^ O
0- I 0
Hr- c nu 	
.3. Vrf v^ vj n ,
0 x"
" * /^
u r n ri-i ^_ -r
C2H5-N-C2H5
V
0
(DENO)
^ \°\
\ \2
, E,,EtN02\
EtO2-
\0
EtO<^
DEHAX I
EtOH CH3CHO
^ 3 2 2
b. rw r>. -+. HP — n
/
/ *
/ NO (Ft^ N NO
^
02/
Eto^. Ji£^ E)0
\ F + O^ ^- P 1 1 ^
» C.TU • *" Un,v
\ 4°
E1NO2
^EtO-
\v
EtON02
or
CH3CHO 4 HONO
                                                                                                 N02
                                Figure 19.   Possible  reaction mechanism for DEHA.

-------
Heicklen (4) reported an ~40-min inhibition period between onset of DEHA
removal and the appearance of CH CHO, nitroethane  (CH CH.NO-)  (EtNO ) and NO.
He suggests that the compound (Et) -N-NO may serve as an unidentified inter-
mediate in the reaction scheme.   (The suggested reactions are  included in
parentheses in Figure 19.)  Some of the reactions included in  the mechanism
must be considered to be speculative in nature.  The paucity of thermodynamic
data makes theoretical predictions of possible reaction routes and rates
extremely difficult.

     The photolytic rate constants in the model and an initial concentration
of HONO were adjusted to emulate the NO removal rate observed  in the chamber
runs without DEHA.  The model overpredicts 0  formation  (therefore, the HC re-
moval rate is also too fast), a feature characteristic of this particular
model (Dodge and Ascher, private communication).  Reactions involving DEHA
were then added to the mechanism.  Initial attempts at modeling the entire
reaction scheme actually increased the overall reaction rate.  For simplicity,
the DEHA reaction scheme was truncated with DENO, and the simulation was rerun
in an attempt to model the initial portion of the irradiation.  Figure 20
shows a comparison of the simulations with and without DEHA added.

     The simulations show that, with this particular reaction  mechanism, the
addition of DEHA does indeed retard onset of O  production and NO conversion
and slow the HC removal rate.  The NO does increase initially, as is observed
experimentally  (although the model achieves this primarily through reaction
of DEHA with HONO).  The difficulties involved in modeling the initial NO
increase indicate that the mechanism may be either incomplete  or inadequate
in regard to NO  chemistry.  This may also be the reason that  the model tends
               X
to over-predict 0  formation.

     The rate constant used for Reaction  (a)
                             DEHA + OH ->  DENO  +  HO                      (a)
                                       33

-------
              i.o-
             0.9-
             0.8-
             0.7H
             0.6-
             0.5
          E
          Q.
          O.
          O
          (-
          <
          O
          z
          O
          O
                       50
100    150    200    250
   TIME--*- (minutes)
300    350
Figure 20.  Simulation profiles for HC, NO, NO , 0,, and DEHA predicted by

            kinetic model.   Initial concentrations are:  [HC]0 = 0.5 ppm
            propylene;  [NO]0  = 0.4 ppm; [NO ]  = 0.1 ppm; [O  ]0 = 0.0 ppm;

            and  [DEHA]0 = 0.0 or 0.125 ppm.  Dotted lines are the  "no  DEHA"
            case.  Solid lines show simulation with DEHA included.
                                       34

-------
varied between 1.4 x 10  ppm   min   and 4.1 x 10  ppm   , with an intermediate
value of ~2.6 x 10  ppm   min   generally being used.


     An upper limit of 0.02 ppm   min   was estimated for reaction  (b)
                            DEHA + N02 ->• DENO + HONO                     (b)


based upon data obtained while charging the chamber for irradiations and from

data quoted by Heicklen  (2).  B. Gay detected by Fourier transform infrared

spectroscopy  (FTIR) the rapid formation in the dark of HONO from the mixture

of NO  and DEHA in a different chamber, but that rapid reaction may have been
influenced by wall effects.*
     The rate constant for reaction of O  and DEHA


                           0  + DEHA •*• DENO + OH + 0                     (c)


was estimated as >1.3 ppm   min   from plots of the reaction of O  with DEHA

published by Heicklen  (18).  A similar lower limit rate constant was used  for

reaction  (d):
                              O + DEHA -»• DENO + OH                       (d)


     The reaction rate constant of HONO and DEHA was permitted to vary as

required:


                          HONO + DEHA -»• DENO + HO + NO                  (e)


     Ratios of the subsequent reactions can be estimated  from product distribu-

tions.  The magnitudes of the rates must be adjusted to account  for  the  actual

reactivity of the system.
*Gay  (private communication).  The formation of HONO  in a  nonirradiated mixture
of NO  and DEHA was unmistakable, but because these two compounds have existed
in the gas phase in other chambers without rapid reaction,  the  results observed
by Gay may be attributable to surface effects.  A subsequent  5-min  irradiation
showed removal of both DEHA  and HONO with no identifiable  product buildup.
                                      35

-------
                                   SECTION 5
                                  CONCLUSIONS
     The results of adding DEHA to chamber irradiations of HC/NO  systems were
                                                                X
empirically defined for propylene and n-butane.
     As long as DEHA was present in the gas phase in the chamber, the physical
manifestations of smog formation were retarded or inhibited.  However, DEHA is
an organic molecule which does react to produce "smog" itself; once it was con-
sumed, all of the manifestations of smog production were aggravated in the
test reaction systems.  In particular, the chamber runs indicated that the
DEHA-consumed system produced:  (1) increased 0  formation;  (2) rapid con-
version of NO to NO ;  (3) increased HC consumption; (4) increased PAN pro-
                   X
duction;  (5) aerosol in greater volume and in a size distribution that is more
likely to affect visibility; and (6) a significantly different NO  product
profile.  These results have significant impact on any proposed control strategy
involving DEHA.

     It has been suggested  (4,6,16) that continual and sufficient introduction
of DEHA into the urban environment could significantly lower the exposure of
the urban population to smog.  Under normal meterological conditions, this
conclusion is probably correct.  However, addition of DEHA to the urban atmo-
sphere is much like "adding fuel to the fire."  Should the concentration of
DEHA drop below "adequate" levels, the adverse effects of smog on the urban
population are likely to be exacerbated.  In addition, these studies indicate
that the impact on rural areas downwind from the urban center may be significant
and undesirable.  Under conditions of stagnant air over the urban center, the
necessary amount of DEHA to be injected on the second and subsequent days
                                      36

-------
would have to be increased to overcome the reactivity of both the cumulative


HC and NO  emissions and the buildup of DEHA reaction products.  At some
         X

point, DEHA concentrations would become unacceptable  (on account of odor,


etc.), or the reactivity of the total organic chemical loading would become


sufficiently large to overwhelm the DEHA inhibition and produce smog effects


despite the presence of DEHA.





     Finally, introduction of DEHA into the atmosphere may expose the populace


to some unknown NO  product of DEHA.  The runs presented above show that the
                  X

NO  profile is significantly different with DEHA added to the system.  The
  X

high NO  concentrations late in the DEHA runs cannot be accounted for by PAN,
       X

NO , NO, and nitric acid (HNO,).  CH CH NO  and N0O (the major NO  products
  £.                          J      j  ^  £•      £               X

identified by Heicklen  (4)) could not be monitored because of gas chromato-


graphic insensitivity, but studies of the response of the chemiluminescent NO
                                                                             X

instrument indicate that substantial concentrations of these compounds would


be required to account for the observed NO  readings.  This implies that some
                                          X

other NO  product  (or a chemiluminescent interferent) must be formed during
        X

the reaction.  An attempt to analyze these NO  products by FTIR was unsuccessful
                                             X

because of experimental problems  (Gay, private communication; see previous


footnote).  The reaction scheme in Figure 19 suggests several possible inter-
                                ), EtN=C
mediate NO  products (EtNO, DENO, EtN=CHCH , etc.); Heicklen et al. (4) have
          X                               -J

                       ?
also suggested (C H ) -N-NO.  The possible hazards of exposure to these or


other possible NO  products of the reaction are currently unknown.
                 X
                                      37

-------
                                  REFERENCES
1.    Stephens, E. R.,  R.  H.  Linnell, and L. Reckner.  Atmospheric Photochemical
     Reactions Inhibited by Iodine.  Science 138:831, 1962.

2.    Jayanty, R. K. M., R. Simonaitis, and J. Heicklen.  The Inhibition of
     Photochemical Smog.   III.  Inhibition by Diethylhydroxylamine, N-Methylani-
     line, Triethylamine, Diethylamine, Ethylamine and Ammonia.  Atmos. Environ.
     8:1283, 1974.

3.    Two New Approaches to Smog Control.  Chemical and Engineering News 54(37):
     32, 1976.

4.    Stockburger, L. ,  B.  K.  T. Sie, and J. Heicklen.  The Inhibition of Photo-
     chemical Smog.  V.  Products of the Diethylhydroxylamine Inhibited Re-
     action.  Report No.  407-75, Center for Air Environment Studies, The
     Pennsylvania State University, University Park, Pennsylvania, 1975.

5.    Pitts, J. N., Jr., J. P. Smith, D. R. Fitz, and D. Grosjean.  Enhancement
     of Photochemical Smog by N,N'-Diethylhydroxylamine in Polluted Ambient
     Air.  Science 197:255,  1977.

6.    Schaal, D., K. Partymiller, and J. Heicklen.  The Inhibition of Photo-
     chemical Smog.  VII.  inhibition of Diethylhydroxylamine at Atmospheric
     Concentrations.   Report No. 483-77, Center for Air Environment Studies,
     The Pennsylvania State University, University Park, Pennsylvania, 1977.

7.    Cupitt, L. T., and E. W. Corse.  Status Report and DEHA Experiments.
     ESG-TR-78-17, Northrop Services, Inc., Research Triangle Park, North
     Carolina, 1978.

8.    Selected Methods for the Measurement of Air Pollutants.  Division of Air
     Pollution, Public Health Service, U.S. Department of Health, Education,
     and Welfare, 1965.

9.    Miller, D., and C. Spicer.  Measurement of Nitric Acid in Smog.  J. Air
     Pollution Control Assoc. 25:940, 1975.

10.  Schere, K., and K. Demerjian.  Calculation of Selected Photolytic Rate
     Constants over a Diurnal Range: A Computer Algorithm.  EPA-6001/4-77-015,
     U.S. Environmental Protection Agency, 1977.

11.  Leighton, P. A.   Photochemistry of Air Pollution.  Academic Press, New
     York, 1961.

                                      38

-------
12.  Finlayson, B.,  and J. Pitts, Jr.  Photochemistry of the Polluted Tropo-
     sphere.  Science 192:111, 1976.

13.  Reaction Rate and Photochemical Data for Atmospheric Chemistry — 1977.
     Circular No. 513, National Bureau of Standards, 1977.

14.  Weinstock, B.,  and H. Niki.  Carbon Monoxide Balance in Nature.  Science
     176:290, 1972.

15.  Wang, C., L. Davis, Jr., C. Wu, S. Japur, H. Niki, and B. Weinstock.
     Hydroxyl Radical Concentrations Measured in Ambient Air.  Science 189:797,
     1975.

16.  Gorse, R., Jr., R. Lii, and B. Saunders.  Hydroxyl Radical Reactivity
     with Diethylhydroxylamine.  Science 197:1365, 1977.

17.  N, N-Diethylhydroxylamine: Reactions and Applications.  PD-106, Product
     Development Department, Industrial Chemicals Division, Pennwalt Corpora-
     tion, 1969.

18.  Olszyna, K., and J. Heicklen.  The Inhibition of Photochemical Smog.
     VI.  The Reaction of 0- with Diethylhydroxylamine.  Report No. 405-75,
     Center for Air Environment Studies, The Pennsylvania State University,
     University Park, Pennsylvania, 1975.
                                      39

-------
APPENDIX
   40

-------
I.O-
0.9-
o.e-
0.7-
        6O   I2O
                                                                         84O   9OO
                                     TIME ,
   Figure A-l.   Reaction profiles of DEHA-NO  system.

-------
NJ
             0.9
             o.a
                    60    120   IBO   240    3OO   360   420   4SO    540   6OO   660   72O    760   B4O
                Figure A-2.   Reaction profiles of 0.25 ppm propylene-NO  system.
                                                                             X

-------
0.9
o.a
0.7H
o.e
O.I
        60    12O   ISO    24O   3OO
                                  36O   4 2O   460




                                   TIME, minulos
                                                   640   6OO   660   720    7BO   84O
   Figure  A-3.   Reaction profiles of 0.25  ppm propylene-NO   system.

-------
 I.OH
0.9-1
 O   NO,
 a   NO
 *   03
 O   OEHA
     Propylen
I  i   Sail i man
             I2O   ISO   240   3OO   36O   42O   480   S40    60O   66O
   Figure  A-4.  Reaction  profiles of 0.24 ppm propylene-NO -DEHA system.

-------
Ui
                       O   NO,
                       a   NO
                       A   Oj
                       O   DEHA
                          Propylene
                          Soltzmon
                               ISO    Z40   SOO    360   420   4BO   540
             O.
                                                                                      78O   840    9OO
                                                TIME, minute*
                 Figure  A-5.   Reaction profiles  of 0.26 ppm propylene-NO  -DEHA  system.

-------
 I.O
 0.9
o.a
0.7
0.6-
o.s
0.4
0.3<
0.2
O.I
 o NO,
 B NO
 A Oj
 V Piopykiw
 O UtHA
	1 Sollimon
        60    120   ISO
                         240   iOO   J6O    420   4BO    S4O    6OO
                            TIME, minulei
    Figure A-6.   Reaction profiles  of 0.30 ppm propylene-NO -DEHA  system.
                                                                      X

-------
 I.O-,
0.9-
0.8-
0.7-
0.6-
0.5-
0.4
O.i
0.2-
0.1 -
                                        42O    48O   540  6OO   660   720   780    840   9OO
   >     6O   120    180   240   3OO
    Figure  A-7.   Reaction profiles  of 0.30 ppm propylene-NO  -DEHA  system.

-------
00
              I.O-
             0.9-
              0.8-
             o.r-
             O.6 -
 o NO,
 13 NO
 A Oj
 tf Prop»l*n«
I	1 Sottlfnon
                      6O    IZO    ISO   240    3OO   360   42O   480   540   600
                 Figure A-8.   Reaction  profiles of  0.49 ppm propylene-NO   system.

-------
0.6-
0.51
0.4 -J
0.3-
0.2-
O.l -
   0     60    I2O   180   24O   JOO   J60   420   460   540
   Figure A-9.   Reaction profiles of  0.48 ppm propylene-NO  system.

-------
Ol
o
             0.6-
             0.5-6
             0.4
           E 0.3-
             0.2-
             0.1-
                                    24O    3OO  360    42O   480   540   6OO   660
                Figure A-10.   Reaction  profiles  of 0.50 ppm propylene-NO  system.

-------
(J1
            o.e
            O.7-
                              ISO   Z4O   3OO   36O   «ZQ   48O   54O   6OO
                Figure A-ll.   Reaction profiles of 0.60 ppm propylene-NO -DEHA  system.

-------
                       O   NOl
Ul
to
              O.7-
              0.6-
                     60
                          120    180   240   300   360   420   48O

                                       TIME, minutes
                                                               540
                Figure A-12.   Reaction profiles of  0.50 ppm propylene-NO  -DEHA system.

-------
 0.9
 O.8-
0.7-
0.6
0.5
0.4-J
0.3-
0.2-
0.1 -
          O   NO

          B   NO

          A
         60    120   180   240   3OO   36O   420   480   540   6OO


                           TIME, minutes
    Figure  A-13.   Reaction profiles of 0.54  ppm propylene-NO  system.
                                                                    X

-------
en
              0.9-
              0.8-
              0.7-
              0.6-
              0.5-
              0.4
              0.3-
              O.2 -
             0. I -
 o   NO,
 D   NO
 *   Oj
 U   Propylen<
	1   Soil/man
                           120    180   240   KM)   360   42O   4 BO    540
                Figure A-14.  Reaction profiles  of 0.47 ppm propylene-NO   system.

-------
en
                                     240    3OO   36O   420    480   54 O  600   660
             0.9-
             0.8-
             0.7-
             0.6-
             0.3-i
             0.4
             O.S -
             O.Z -
             O.I -
                     60    120    180
                                            TIME, minulos
                Figure  A-15.   Reaction profiles  of 0.50 ppm propylene-NO  -DEHA  system.

-------
0.6 -\
0.5 ^
0.4 e
0.2i
o-i -
          O    NO,

          O    NO

          *    Oj

          tf    Propylene

         	1   So Hi mun
   0    6O
              120    180   24O

              TIME, minutes
   Figure A-16.   Reaction  profiles of  0.54 ppm propylene-NO  system.
                                                                    X

-------
Ul
•-J
                     6O    120    ISO   240   30O

                     TIME, minutes
                Figure A-17.   Reaction profiles  of 0.55 ppm propylene-NO  system.

-------
CO
             I.O
             O.9 -
             o.e
             0.7-
             0.6-
             O.5-
             0.44
             0.3 -
             O.2
                     GO    12O   ISO   21O   3«)   360   42O   46O   MO   GOO   66O    720   7BO
                Figure A-18.   Reaction profiles of 0.54 ppm propylene-NO -DEHA system.

-------
vo
              O.6
              0.5
              0.4,
              O.3
              0.2-
              0.1
                      6O    120
                                180  240    300    360   42O

                                TIME . minutes
                Figure A-19.  Reaction profiles  of 0.47 ppm propylene-NO  system.
                                                                                X

-------
 O.6-
 0.5-
0.4 -I I
0.3-
0.2 -
O.I J
        60
              120    ISO    24O   JOO   36O

                   1IME. minutes
    Figure A-20.   Reaction profiles of  0.52 ppm  propylene-NO  system.
                                                                  X

-------
  0.6-
  O.S-
E O.4 -I
  0.3-
  0.2-
  O.l -
          6O    12O   180   240   3OO   J6O   42O  4BO   51O   6OO   66O
     Figure  A-21.   Reaction  profiles  of 0.52  ppm propylene-NO  system.

-------
en
NJ
              O.6-
              0.5
              0.4-
              0.3-
              0.2-
              0.1 -
                      O   NO.

                      a   NO

                      *   Oj

                      V   Propylent

                     	1  Soil/mod

                      +   PAN
                 0    60    120   180   24O    iOO   J6O

                                   TIME, minules
                                                             4BO   510   60O   660
                 Figure A-22.   Reaction  profiles  of 0.50 ppm propylene-NO  system.
                                                                                     X

-------
Co
              O.9-
              0.8-
              0.7-
              0.6-
              0.5-
             O.4 -
             O.3-
              0.2-
              O.l -
                      6O    I2O    180    240
                                           300    36O    420
                                            TIME . minulei
                                                            480   S4O   6OO    660   720   78O
                Figure  A-23.   Reaction profiles of  0.55 ppm propylene-NO  -DEHA  system.

-------
  6.0 H
  3.0H
e
a.
I 3.O
  2.0-\
  • oH
         O.6
            0  30 6O 9O IOO
             TIME, oimulei
            Figure  A-24.  Reaction profiles of  5.0 ppm propylene-NO  system.

-------
en
Ul
                       o   NO.

                       a   NO
                          Propylenc
      3.0-
             O.5
      3.0-
      1.0-
       o-
                0 SO 6O  9O I2O


                 TIME, cninutet
                Figure A-25.  Reaction profiles of  5.2 ppm propylene-NO  system.
                                                                                X

-------
            o  NO
6.0-
5.0-
4.0-
      O.6
2.0-
1.0-
 0 J
         0  30 6O 90  I2O
             TIME.mmuUt
         Figure A-26.  Reaction profiles of  5.1 ppm propylene-NO  system.

-------
CTi
   6.0 -


   S.O .



J  4.O •
«
I

E
a

   2.0-


   1.07


    O-
              o.s
              O.B -
              0.7
              O.6-
                   0   NO,
                   Itl   NO
                   A   03
                   ^   Propylene
                   O   OtHA
                   I	1 Sail i man
                   •>   HNOj .miciacoulomtlry


                                 NO it
                                                          TIME, mingles
                 Figure A-27.   Reaction profiles  of  5.3 ppm propylene-NO -DEHA  system.

-------
             0.9H
      6.0H
00
      4.0-1
    §

    |
    o.

    I
       I .OH
        o-J
                0  3O 60 90 120 ISO I8O 210 24O 27O JOO   36O   420    4BO   S4O   6OO   66O   72O   78O   840   9OO
                Figure A-28.   Reaction profiles  of 4.7 ppm propylene-NO -DEHA system.

-------
  6.0-
  5.0-
  4.O-
I 3.0H
  2.O-
  I .0-
    O-1
                                       1	1	1   i   i	1	1	1	1	1	1	1	1	1	1	1	1	1	1	1	1	r
            6  3O  6O 9O  120 150 180 210 24O 270 30O 330 36O 39O ISO 4SO 48O 510 54O 57O 6OO 63O 66O 690 72O 75O 780 810 840 870 9OO


                                                 TIME , minutes
             Figure A-29.   Reaction profiles of  4.9  ppm  propylene-NO  -DEHA system.
                                                                                X

-------
   6.0-
   5.0


«*



I  4.0-
   1.0-
   2.0-
   1.0-
    O-i
          0.3
          O.I -
              ' 	1	1	1	1	1	1	1	*—*?  ***  9  V  *P—9	1	1	1	1	1	1	1	1	1	1	1	1	1	1	1	1	1	1	1	1	1	1	
              0  30 60 9O 120 ISO 180 2K> 24O 270 3OO 330 36O 39O 
-------
6.0-
           O  3O 6O 9O 120 ISO 180 210 240 27O iOO 3JO J6O 39O 420 46O 48O SIO 540 570 600 630 660 69O 720 75O 760 610 640 870 9OO 93O 96O i«O 1020 I05O 1060 1110 IHO



                                                       TIME, minutes
           Figure  A-31.   Reaction  profiles of 4.7  ppm propylene-NO  -DEHA system.

-------
NJ
              O    6O
                                                                                    84O   .9OO   96O    IO2O
               Figure A-32.   Reaction profiles of 0.49 ppm  n-butane-NO  system.

-------
0.6 -(
0.5J
0.4
0.3
0.2-
O.l -
                                  360   420   480   540   60O660   T2O   78O   84O    9OO   96O
   Figure  A-33.   Reaction profiles of 0.59 n-butane-NO   system.
                                                            X

-------
O.4
0.2 -
        60     120    ISO    24O   MO    36O
                                                                    10 BO

                                                             TIME , minutes
                                                                                    I26O   IS20   IJ80    I44O   I50O
   Figure  A-34.   Reaction profiles  of 0.48 ppm  n-butane-NO   system.
                                                                  X

-------
                                                           72O   /6U   U4U   9OO   06O  IO2O   lOtIO   II4U
Figure  A-35.  Reaction profiles of 0.46 ppm n-butane-NO -DEHA system.
                                                            X

-------
cr>
            O.I
                    60
                                                                                     84O   9OO   961)  IO20  IOUO   II4O
                                                   1IME. minutM
               Figure A-36.   Reaction profiles of  0.55 ppm n-butane-NO -DEHA system.
                                                                            X

-------
-J
-o
             I.O-i
             0.9H
            O.I
                                                                                                          IO8O  IHO
                                                          TIME, minuies
               Figure A-37.   Reaction profiles of 0.59 ppm n-butane-NOx-DEHA system.

-------
-J
GO
       6.O-
       5.0-
       4.0-
    a>
    •   3.O-
       2.0-
       1.0-
                      60    120
                                 I6O    24O   3OO

                                  TIME,minute*
                                                36O   420
                 Figure A-38.   Reaction profiles  of 4.9  ppm n-butane-NO   system.

-------
       Ob
ti.O-
4.O -
3.0-
2 .O-
1.0-
  0 J
              6O    120   I BO
      r
240   3OO   36O
TIME, minultt
                                             420   46O   540
                                                                  6OO
         Figure A-39.   Reaction profiles of  4.9 ppm  n-butane-NO  system.

-------
00
o
                                                                       66O   720   7BO    840
                                                                                           loo
                                                                                                 960   I02O
                                                TIME.minulei
               Figure A-40.  Reaction profiles  of 4.3 ppm n-butane-NO -DEHA system.

-------
00
      5.0-
      4.0 -
   I 5-0-
     2 .0 -
     \ .0 -
                                                        480   540

                                                     TIME .minutes
                                                                                   780   840   9OO   960   1020    I08O
               Figure A-41.   Reaction profiles of  4.7 ppm n-butane-NO -DEHA  system.
                                                                            2C

-------
              i.o-
              O.9
             o.a
00
to
      6.0-
       5.O-
       4.O -
       3.0 -
       2.0
       1.0-
                                                                                                                O   1140
                                                   TIME. mmul«»
                 Figure A-42.  Reaction profiles of  4.8 ppm  n-butane-NO -DEHA system.

-------
en
U)
  16.0-
  15.O
  14.0
  13.0-
  12.0
  11.0-
  10.0-
   9.O-
J 8.0
o
I  7.0-
i
   6.O-
   50-
  4.0-
   3.O-
  2.0-
   I.O-
    0 -
     E
               0.9-
               0.8-
               0.7-
               0.6-
               0.5-
               0.4 '
               0.3.
              0.2-
              0.1-
                       60
                             120   180   24O    300    36O
                                     TIME . minulec
                  Figure A-43.   Reaction profiles of 14.0 ppm n-butane-NO  system.

-------
00
  15.0

  11.0

  I3.0

  I2.O-

  II.O

  IO.O

  9.0
•
o a.o

f ,oH
a
a 6.O

  3.O


  3.0

  Z.O

  I .0

   O
  0.9 -


  0.8


  O.7-


  0.6-



o
o
z
 M
i

| 0.3
a

  O.2-


  O.l -
                       6O    120    180    24O
                                TIME, minute.
                                              JOO    360
                   Figure A-44.   Reaction profiles of  14.3 ppm n-butcUie-NO  system.
                                                                                       X

-------
CO
(Jl
       16.0-
       15.0-
        .0-
       13.0-
  12.0-

  11.0-

  IO.O-

• 9.O-
o
5 8.O-
       7.0-

       6.0-

       3.0-

       ^.0-

       3.O-

       2.O-


       1.0-

         O-
               l.O-
               0.9-
               0.8-
               O.7-
               O.6-
                     o   NO,
                     a   NO

                     *   °s
                     O   n-Butanc
                     O   OEHA
                    	'  SalKmon
                      n-8ulaiw
                       6O    120    ISO    240    JOO    360   42O   480   54O   6OO
                 Figure A-45.   Reaction profiles  of  13.6 ppm n-butane-NO -DEHA system.
                                                                                       X

-------
00
 16.0



 15.0



 M.O-I



 I3.O-



 I?..fl-




 it.O-



 IO.O-



  9.O

•


| e.o




  7.0



6 6.0-

c&
a

  5.O-



  4.O



  3.O



  2.O



  I.O-j



   O-
    01
             0.3
             0.2
             0.1-
                                                                                           84O   9OO    96O
                Figure A-46.   Reaction profiles  of 13.5 ppm n-butane-NO -DEHA system.
                                                                                 X

-------
00
              o.s-<
              o.i
              o.j-
              O.2 -
              O.I -
                 0     6O    120    180   Z40   3OO   J6O   420    4 BO   S4O   GOO   66O
                                                    TIME, inlnules
                                                                                          780   84 O   90O
                  Figure A-47.   Reaction profiles  of NO  system.

-------
                                   TECHNICAL REPORT DATA
                            (Please read Instructions on the reverse before completing)
 1. REPORT NO.
    EPA-6QO/3-79-040
                              2.
                                                            3. RECIPIENT'S ACCESSION-NO.
 4. TITLE AND SUBTITLE
   EFFECT OF DIETHYLHYDROXYLAMINE ON SMOG CHAMBER
   IRRADIATIONS
                                                      5. REPORT DATE
                                                          April  1979
                                                      6. PERFORMING ORGANIZATION CODE
 7. AUTHOR(S)
   L.  T. Cupitt
   E.  W. Corse
                                                            8. PERFORMING ORGANIZATION REPORT NO.
'9. PERFORMING ORGANIZATION NAME AND ADDRESS
   Northrop Services  Inc.
   Environmental Sciences  Center
   Research Triangle  Park,  North Carolina
                                                      10. PROGRAM ELEMENT NO.

                                                        1AA603    AC-02   (FY-78)
                                                      11. CONTRACT/GRANT NO.
                                       27709
                                                             Contract no.   68-02-2566
 12. SPONSORING AGENCY NAME AND ADDRESS
  Environmental Sciences  Research Laboratory-RTF,  NC
  Office of Research  and  Development
  U.S.  Environmental  Protection Agency
  Research Triangle Park,  North Carolina  27711
                                                      13. TYPE OF REPORT AND PERIOD COVERED
                                                        Final
                                                      14. SPONSORING AGENCY CODE

                                                        EPA/600/09
 15. SUPPLEMENTARY NOTES
 16. ABSTRACT
        The addition of diethylhydroxylamine  (DEHA)  to  the urban atmosphere had
  been suggested as a means  of  preventing photochemical smog.  Smog chamber  studies
  were carried out to investigate the photochemical smog formation characteristics
  of  irradiated hydrocarbon-nitrogen oxides - DEHA  mixtures.   Propylene and  n-butane
  were the hydrocarbons used.   The effects of DEHA  upon ozone formation, aerosol
  formation, peroxyacetyl nitrate formation, nitric oxide-to-NO  conversion,  HHd
  hydrocarbon consumed are described.  The rate constant for  thS reaction
                                 DEHA + OH
                                           products
  was  estimated as 4.1 + 3.4  X 10  ppm  min  .  Possible reaction schemes for DEHA
  in the photochemical smog mechanism are discussed.

        The addition of DEHA to a HC/NO  system inhibits  the conversion of NO to
  NO-  during the initial minutes of irradiation, but after continued irradiation
  accelerates this conversion.
 7,
                                KEY WORDS AND DOCUMENT ANALYSIS
                  DESCRIPTORS
                                              b.lDENTIFIERS/OPEN ENDED TERMS
                                                                    c.  COSATI Field/Group
  *
  *
Air pollution
Hydroxyamine
Nitrogen oxides
Propylene
Butanes
Photochemical reactions
Test chambers
  13B
  07B
  07C
  07E
  14B
 8. DISTRIBUTION STATEMENT

  RELEASE TO  PUBLIC
                                         19. SECURITY CLASS (ThisReport)
                                          UNCLASSIFIED
21. NO. OF PAGES

        100
                                              20. SECURITY CLASS (Thispage)
                                                UNCLASSIFIED
                                                                         22. PRICE
EPA Form 2220-1 (9-73)

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