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Diesel (U)LSD Hydrotreating

UOP Technology Seminar Lima (Peru)
April 11-13, 2007
Albemarle Catalysts Company LP
Kaspar Vogt
Business Development Manager

Seminar Topics
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Chemistry / Kinetics
Diesel Sulfur Chemistry
Feed Effects
endpoint
cracked stocks (LCO & Coker Diesel)

Catalyst Inhibition
Diesel Color
Aromatics Saturation
H2 Consumption
Maximizing Hydrotreater Performance
Feed Management
Catalyst Selection
ULSD Catalyst Selection Guidelines
Commercial Example

ULSD Guard Catalyst Selection

2

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ULSD Chemistry & Kinetics

Diesel Sulfur Compounds

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Sulfur
Compound
Structure

Name

Relative D-86 EP
Reaction
When
Rate
Observed

dibenzothiophene

6 - 12

590F

4-methyldibenzothiophene

2-4

600-620F

4,6-dimethyldibenzothiophene

630-650F

3,4,6-trimethyldibenzothiophene

660-680F

H3C

H3C

CH3

CH3
H3C

CH3

Sterically hindered di-benzothiophene species (SH-DBT)

4

SH-DBT Source/Origin
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Significant levels of SH-DBT can be present in all feeds

SH-DBT Content: LCO > Coker Diesel > SRD
Endpoints > 600F:
SH-DBTs present

Endpoints > 630F:

Increase 4,6 DM-DBT concentration

Endpoints > 650F:

Increase tri-methyl-DBT concentration
Greater probability of DBT species with 4,6 di-methyl
substitution

Reducing endpoint is the only effective way to eliminate

these compounds from feeds
5

Sulfur Speciation
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counts
300000
Feed: ~5000 wppm S

250000
200000
150000
100000
50000
0
5

10

15

20

25

30 min

Straight run diesel has a wide variety of sulfur compounds

6

Sulfur Speciation
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counts
300000
250000

Feed:~5000 wppm S
Product: ~100 wppm S

200000
150000
100000
50000
0
5

10

15

20

25

30 min

Final ~100 ppm of sulfur is 4,6 DM-DBT and derivatives

7

Refractory SH-DBT Sulfur Species:

Reaction Mechanism

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Reaction paths for SH-DBT conversion:

4,6-Dimethyl-Dibenzothiophene
H3C

CH3

Aromatic Saturation Route (ASR)

Direct
Route
(DR)

S
H3C

CH3

kASR >> kDR

H3C

CH3

H3C

CH3

Steric Hindrance
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DMDBT has all sulfur and carbon atoms in the same plane
Direct hydrogenolysis route inhibited by steric hindrance of
alkyl groups on 4,6 position in the adsorbed sulfur
compound

DBT

4,6-DM-DBT

Hydrogenation Route
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Aromatic ring saturation relieves steric hindrance effect

10

Diesel HDS Lower Limit

(Sulfur Floor Phenomenon)

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100

Commercial, Low Pressure DHT

Feed: SR Diesel/LCO
Catalyst: KF-757 (CoMo STARS)

Product S (wppm)

90
80
70

Aromatic
saturation
equilibrium
limited

60
50
40

Kinetic
control

30
20
10
0
620

630

640

650

660

670

WABT (F)

The HDS limit of any diesel hydrotreating unit depends on

feed properties, pressure, LHSV, and catalyst activity
11

Organic Nitrogen: Reactivity & Boiling

Point

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10

Relative Reaction Rate

9
N

8
7
6
5
4

3
2
1
0
450

500

550

600

650

700

True Boiling Point (F)

12

750

800

850

Diesel Aromatic Species Boiling Points

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Aromatic
structure

13

Name

MW

True
Boiling
Point

D-86 FBP
When
Observed

Naphthalene

128.2

424F

~ 400F

Anthracene

178.2

644F

~ 605F

Phenanthrene

178.2

644F

~ 605F

Fluoranthene

202.3

707F

~ 665F

Pyrene

202.3

739F

~ 695F

0.5

100

0.0

14

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S (wt%)
N (ppm)

N (ppm)

200

F-12

1.0

F-11

300

F-10

1.5

F-9

400

F-8

2.0

F-7

500

F-6

2.5

F-5

600

F-4

3.0

F-3

700

F-2

3.5

F-1

S (wt%)

Effect of Feed Boiling Range on Nitrogen

& Sulfur Contents

TBP Basis
F-1: 360-390F
F-2: 390-410F
F-3: 410-445F
F-4: 445-480F
F-5: 480-505F
F-6: 505-535F
F-7: 535-560F
F-8: 560-600F
F-9: 600-640F
F-10: 640-665F
F-11: 665-695F
F-12: 695-725F

Relationship of Feed Endpoint and Total

Sulfur & Nitrogen Contents

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200

2.5

180
S (wt%)

160

N (ppm)

140
120

1.5

100
1.0

80
60

0.5

40
20

0.0
350

0
400

450

500

550

600

TBP Endpoint Temperature (F)

15

650

700

750

Total Feed N (ppm)

Total Feed S (wt%)

2.0

Relationship of Feed Endpoint and Total

Aromatics Content & API Gravity

32.0

API Gravity

46.0

Total Aromatics (vol%)

31.0

44.0

30.0

42.0

29.0

40.0

28.0

38.0

27.0

36.0

26.0

34.0

25.0

32.0

24.0

30.0

350

16

48.0

400

450

500
550
600
650
TBP Endpoint Temperature (F)

700

750

API Gravity ()

Total Feed Aromatics (vol%)

33.0

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Relationship of Feed Endpoint and

Feed Properties

17

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Total
API
Aromatics
Gravity ()
(vol%)

Feed TBP
EP (F)

Feed D-86
EP (F)

S (wt%)

N (ppm)

670

630

1.75

56

30.6

33.7

680

640

1.80

67

31.0

33.4

690

650

1.85

79

31.3

33.0

700

660

1.90

92

31.7

32.7

710

670

1.95

105

32.1

32.4

720

680

2.00

119

32.5

32.1

Impact of Feed Endpoint on Catalyst

Cycle Length: ULSD Operation
2.5

25

Model Projections

15
10
5

1.5

0
-5
1.0

-10
-15

0.5

-20
-25
-30

0.0
630
18

640
650
660
670
Feed D-86 Endpoint (oF)

680

Process Conditions:
Relative SOR WABT (F)

Relative Cycle Length

20
2.0

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LHSV = 1.0 hr-1

ppH2 = 450 psia
H2/Oil = 1400 SCFB
CoMo Catalyst
Product S = 7 wppm

Cycle Length
WABT

Feed Endpoint Effects: Commercial

Example with LCO

Normalized WABT (F)

+30F LCO EP

+20F LCO EP
+10F LCO EP
Base LCO EP

Impact of LCO EP on WABT required

to achieve product sulfur target.
Time on Stream
19

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Endpoint Effects - Summary

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SH-DBT species, organic nitrogen, and aromatics

concentration increase with increasing diesel feed
endpoint.
Higher feed endpoints result in:
increased process severity requirements
higher H2 Consumption
increased catalyst deactivation
significant reductions in cycle length

Feed Endpoint Management:

critical factor in achieving desired cycle length

20

Cracked Stock Effects on Feed

Properties: Western USA

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SRD

LCO

CGO

1.00

2.91

2.27

Nitrogen (ppm)

92

551

945

API Gravity ()

36.4

15.6

32.0

Bromine No. (g/100 g)

1.3

6.6

26.0

IBP

325

355

356

10 vol%

407

451

406

50 vol%

493

527

519

90 vol%

598

635

635

FBP

629

717

674

20.2

66.6

27.9

mono-

15.6

52.6

21.7

di-

4.6

13.5

6.0

tri-

0.1

0.5

0.2

Sulfur (wt%)

D-86 (F)

Aromatics (vol%)

21

Cracked Stock Effects on Feed

Properties: Gulf Coast USA

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SRD

LCO

CGO

Sulfur (wt%)

1.78

1.01

2.66

Nitrogen (ppm)

379

875

1028

API Gravity ()

31.7

14.3

30.1

Bromine No. (g/100 g)

1.9

2.9

22

IBP

417

396

438

10 vol%

503

476

458

50 vol%

568

540

518

90 vol%

631

638

596

FBP

661

685

636

36.0

84.8

40.2

mono-

19.5

16.6

21.2

di-

15.2

59.1

17.4

tri-

1.3

9.1

1.6

D-86 (F)

Aromatics (wt%)

22

Cracked Stock Effects on Feed

Properties: Gulf Coast USA
SRD/LCO/CGO (vol%)

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100/0/0

0/100/0

0/0/100

50/25/25

Sulfur (wt%)

1.78

1.01

2.66

1.78

Nitrogen (ppm)

379

875

1028

672

API Gravity ()

31.7

14.3

30.1

26.5

Bromine No. (g/100 g)

1.9

2.9

22

7.0

IBP

417

396

438

396

10 vol%

503

476

458

472

50 vol%

568

540

518

550

90 vol%

631

638

596

628

FBP

661

685

636

685

36.0

81.8

40.2

50.5

mono-

19.5

16.6

21.2

19.1

di-

15.2

59.1

17.4

27.9

tri-

1.3

9.1

1.6

3.5

D-86 (F)

Aromatics (wt%)

23

Cracked Stock Effects on Feed

Properties Summary

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Critical Cracked Feed Properties:

Organic Nitrogen
Polynuclear Aromatics
Olefins
SH-DBT Species

Cracked Feed Impacts:

More Refractory Feed Sulfur

Higher Catalyst Inhibitor Levels
Significantly Higher H2 Consumption
Higher Delta T / Exotherm
Greater Catalyst Fouling Potential

All feed properties influence unit performance

24

Cracked Stocks & Hydrogen Availability

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Cracked Stocks consume 600-1200 SCFB H2

pressure dependent
PNA content dependent
High H2 consumption can lead to localized hydrogen deficiency,
especially near the reactor outlet where temperature is highest
H2 deficiency:
catalyst fouling / deactivation
poor distribution
Hydrogen availability gives an indication of tendency for catalyst to
foul

H2 /OilInlet (SCFB)
H2 Availabil ity =
H2 Consumed (SCFB)

Hydrogen availability > 4 is recommended when processing Cracked

Stocks
25

Maximizing Cycle Length in Cracked

Stock Processing
Catalyst Break In
First 30 Days:
Reduce Cracked Stock
Reduce Cracked Stock Endpoint

Hydrogen Availability
> 4 Recommended

Maximize ppH2
Reduce Cracked Stock Endpoint

26

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Hydrotreating Catalyst Inhibition

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Catalyst Inhibitors
Organic Nitrogen
Basic
Non-Basic / Neutral

Aromatics
Organic Sulfur
H2S
NH3

Highly Specific Phenomenon

Inhibitor
Reactant

Strongest Inhibitor: Organic Nitrogen

27

Catalyst Inhibition: Inhibition Dynamics

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Experimental
Catalyst: CoMo/Al2O3
Fixed Bed Flow Reactor
Identical Parallel Rxrs
Common Furnace

Data
4,6 DE-DBT HDS
Inhibitor Effects
Transient
Steady State

ppH2 = 265 psia

Inhibitor Comparison
3-Ethylcarbazole
H2/Oil =650 SCFB
Naphthalene
WHSV = 2.4 hr-1
HDS Activity Recovery
WABT = 510F
4,6-Diethyl-DBT/N-Dodecane
(n-C12H26)
3-Ethylcarbazole &
Naphthalene Inhibitors Reference: T.C. Ho, Catalysis Today, 98 (2004) 3
28

Catalyst Inhibition: Inhibition Dynamics

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Inhibitor

MW

Boiling Point (F)

195.3

705 - 710

128.2

424

C2H5
N
H
3-Ethylcarbazole

Naphthalene

29

Catalyst Inhibition: Inhibition Dynamics

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Composition (wt%)

Feed

0.8

0.8

0.8

3-Ethylcarbazole

0.112
(80 wppm N)

Naphthalene

10

N-Dodecane

99.2

99.09

89.2

4,6-DE-DBT

Reference: T.C. Ho, Catalysis Today, 98 (2004) 3

30

Catalyst Inhibition: Inhibition Dynamics

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80

Feed B
Feed C
Feed A (after B)
Feed A (after C)

% HDS

60

40

20
Feed A used
before 400 hr TOS
0
400

450

500

550

TOS (hr)
31

600

650

Reference: T.C. Ho,

Catalysis Today, 98
(2004) 3

Catalyst Inhibition: Inhibition Dynamics

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HDS (%)

Product N (ppm)

80
TOS < 0:
TOS > 0:
60

40

Reference: T.C. Ho,

Catalysis Today, 98
(2004) 3

20

0
0

20

40

TOS (hr)
32

Feed A
Feed B

60

80

Diesel Color: A Complex Issue

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Color Bodies
Low Concentrations
Significant
Identification Difficult

Factors Impacting Diesel

Color
Feedstock
olefins
polynuclear aromatic (PNA)
species
nitrogen species
cracked stocks
reactive feed components

33

Factors Impacting Diesel

Color (cont.)
Process Conditions
low ppH2
high temperature operation
EOR

Feed Handling
exposure to oxygen
exposure to light

Yellow-Green, Blue, Red

Diesel Color: Effect of Aromatic

Saturation
Aromatic
Species

Relative
Fluorescence
Intensity

Partially Saturated
Species

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Relative
Fluorescence
Intensity

22.5

0.0
1,2,3,10btetrahydrofluoranthrene

fluoranthrene

7.0
anthracene

0.0
9,10-dihydroanthracene

Reference: X. Ma, et.al., Energy & Fuels, 10 (1996) 91

34

Diesel Color: 3 Ring Aromatic Structures

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Aromatic Species

MW

Relative
Fluorescence
Intensity

178.2

7.0

178.2

0.0

anthracene

phenanthrene

Reference: X. Ma, et.al., Energy & Fuels, 10 (1996) 91

35

Diesel Color: 4 Ring Aromatic Structures

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Aromatic Species

MW

Relative
Fluorescence
Intensity

228.3

1.3

228.3

2.0

228.3

0.0

202.3

0.3

naphthacene

2,3-benzophenanthrene

chrysene

pyrene
Reference: X. Ma, et.al., Energy & Fuels, 10 (1996) 91
36

Diesel Color: Effect of Boiling Range

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40

PNA (wt%)
Color (RFI)

35

F-1
F-2
F-3
F-4
F-5

30
25
20
15

< 535F
535-575F
575-610F
610-645F
> 645F

10
5
0
Feed

F-1

F-2

F-3

F-4

F-5

Heavy diesel fractions give darker color due to PNAs

37

Controlling Diesel Color Problems

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Maximize ppH2
Maintain Hydrogen Availability > 4
Reduce Dehydrogenation
Reduce Polymerization / Condensation Reactions
Aromatics
Organic Nitrogen

Reduce Feed Endpoint

Ensure Good Liquid Distribution

38

Diesel Aromatics Saturation

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Conventional (LSD) diesel hydrotreating converts

polynuclear aromatics (PNAs) to mono-aromatics with a
minimal net reduction in total aromatic content
ULSD production results in a significant reduction in total
aromatics content

39

Diesel Aromatics Saturation: ULSD

Operation (SRD Feed)
Operating Conditions

40

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KF-757

KF-757

Target Sulfur (ppm)

475

15

WABT (F)

592

664

ppH2 (psia)

400

400

H2/oil (SCFB)

750

750

LHSV (hr-1)

1.4

1.4

Feed Properties

SRD

Sulfur (wt%)

0.45

Nitrogen (ppm)

130

Bromine No. (g/100 g)

0.6

Aromatics (wt%)

31.3

D-86 FBP (F)

685

Diesel Aromatics Saturation: ULSD

Operation (SRD Feed)
Product Properties

Feed

KF-757

KF-848

Sulfur (ppm)

4500

475

15

Nitrogen (ppm)

127

57

11

Bromine No. (g/100 g)

0.6

API Gravity ()

33.3

34.6

35.3

Aromatics (wt%)

31.3

31.4

28.3

mono-

19.1

26.5

23.7

di-

11.1

4.7

4.4

tri+

1.1

0.2

0.2

150

190

H2 Consumption (SCFB)

41

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Diesel Aromatics Saturation: ULSD

Operation (Cracked Feed)
Operating Conditions

KF-757

KF-848

WABT (F)

685

665

ppH2 (psia)

650

650

H2/oil (SCFB)

2200

2200

1.5

1.5

Target Sulfur (ppm)

LHSV (hr-1)
LCO/CGO/SRD (vol%)

42

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25/25/50

Sulfur (wt%)

1.84

Nitrogen (ppm)

323

Bromine No. (g/100 g)

8.5

Aromatics (wt%)

44.1

D-86 FBP (F)

690

Diesel Aromatics Saturation: ULSD

Operation (Cracked Feed)
Product Properties

FEED

KF-757

KF-848

Sulfur (ppm)

18400

Nitrogen (ppm)

323

Bromine No. (g/100 g)

8.5

API Gravity ()

29.7

35.4

36.1

Aromatics (wt%)

44.1

36.6

32.7

mono-

21.2

31.9

29.5

di-

20.2

4.2

2.9

tri+

2.7

0.5

0.3

690

780

38

44

45

H2 Consumption (SCFB)
Cetane Index

43

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ULSD Hydrotreating H2 Consumption

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Aromatic saturation occurs simultaneously with ultra-deep

desulfurization
Sulfur removal from SH-DBTs requires aromatic
saturation
Sulfur-free aromatics species are saturated along with the
SH-DBTs
ULSD production results in much higher H2 consumption
compared to current LSD operations

44

Hydrogen consumption (Nl/l [SCFB])

ULSD Hydrotreating H2 Consumption

100
[600]
80
[480]
60
[360]
Nebula 56 bar (812 psia)

40
[240]

KF 848 56 bar (812 psia)

Nebula 50 bar (725 psia)
KF 848 50 bar (725 psia)

20
[120]

KF 757 50 bar (725 psia)

0
1

45

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10

100
Sulfur (wppm)

1000

10000

Maximizing Hydrotreater Deep HDS

Performance
Maximize ppH2
increase hydrogen recycle
scrub recycle gas
sharpen feed IBP/FBP
H2 Availability

Optimize Liquid Distribution

improve/upgrade reactor
internals
dense load catalyst
use proper bed grading

46

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Maximize Catalyst Activity

high activity catalyst
dense loading

Avoid Over-Treating
Feed Management

Avoid Overtreating
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Overtreating to lower product S levels requires

exponentially more catalyst activity and increases
deactivation
Increases SOR temperature
Increases deactivation rate
Two effects can combine to shorten run length dramatically

Example:
KF-757, 800 psig inlet pressure
1.4 LHSV, 0.22% feed S, 2000 scf/B H2/oil
Example is based on a commercial unit that treated ULSD to
4 ppm S instead of 7 ppm S
47

Overtreating Example
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WABT Required, F

720
700
680
660
640
0.0

2.0

4.0

6.0

8.0

10.0

12.0

10.0

12.0

Deactivation Rate, F/month

Product Sulfur, wppm

4.0
3.0
2.0
1.0
0.0
0.0

2.0

4.0

6.0

8.0

Product Sulfur, wppm

48

Overtreating Example (2)

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Run Length, mos

36
30
24
18
12
6
0
0.0

2.0

4.0

6.0

8.0

10.0

12.0

Product Sulfur, wppm

For a unit making 24 month cycles at 7 ppm product S

Cycle length decreases to 12 mos at 4 ppm product S
Commercially demonstrated

49

Feed Management
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Endpoint Effects
Concentrations of SH-DBT species, organic nitrogen, and aromatics
increases with diesel endpoint
Higher Processing Severity
Catalyst Inhibition
H2 Consumption

Feed Composition
Cracked Feeds (coker distillate/LCO) have high refractory sulfur (SHDBT), organic nitrogen, and aromatics contents.
Higher Processing Severity
Catalyst Inhibition
H2 Consumption

Feed Selection
Balance feed properties (treating requirements) and unit capabilities
Endpoint Reduction
Reduce Organic Nitrogen & Aromatics Contents
Control SH-DBT Content
50

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ULSD Catalyst Selection

ULSD Catalyst Options

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STARS
Super Type II Active Reaction Sites with very high intrinsic
activity for HDS, HDN and Hydrogenation
KF-757 - CoMo
KF-767 - CoMo
KF-848 NiMo
Combined NiMo/CoMo Loads

NEBULA
Bulk metal catalyst
Highest active site density of any hydrotreating catalyst
technology

52

ULSD Catalyst Options

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Moderate to High Pressure ULSD Operation

Typical Relative Relationships

53

Catalyst

HDS RVA

HDN RVA

Relative H2
Consumption

KF-757 (CoMo)

100

100

100

KF-767 (CoMo)

150

130

105

KF-848 (NiMo)

190

150

135

NEBULA

> 250

> 200

> 175

When is CoMo Catalyst Preferred for

ULSD Applications?
Performance constrained units:
low/moderate pressure (ppH2) operation
limited H2 supply / low H2 availability
balance unit capabilities / catalyst activity

Low SH-DBT / low organic N content feeds

straight run feeds
low endpoint feeds

Large reactor volume units

Reduced H2 consumption targeted

54

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When is NiMo Catalyst Preferred for

ULSD Applications?
Moderate/high pressure (ppH2) operation
High H2 Availability
High SH-DBT / high organic N feeds
high endpoint feeds
cracked stocks

Aromatics reduction
Color control/improvement
Cetane improvement
Application Constraints
High H2 consumption in ULSD service
H2 consumption management necessary
55

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When is NiMo/CoMo Preferred for ULSD

Applications?

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Moderate / high pressure (ppH2) operation

Optimize / manage H2 consumption
Optimize catalyst activity / stability
Greater activity than CoMo catalyst systems
Lower H2 consumption than NiMo systems
Potentially greater stability than NiMo catalyst systems

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When is Nebula Catalyst Preferred for

ULSD Applications?

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Moderate/high pressure (ppH2) operation

High H2 Availability
High SH-DBT / high organic N feeds
Feedstock or temperature constraints on cycle length
Aromatics reduction
Color control/improvement
Cetane improvement
ULSD Application Constraints
Potentially high H2 consumption
H2 consumption management necessary

57

Common Metal Catalyst Poisons in

Diesel Hydrotreating: Relative Toxicity

Poison
As
Na
Si

58

Relative Toxicity
10
0.3 1.0
< 0.1

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Common Metal Catalyst Poisons in

Diesel Hydrotreating: Sources & Impact
Poison

59

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Sources & Impact

As

Crude (Synthetic Crude, Russian, Chinese, West African)

Drilling Mud Diesel
Present in All Fractions
Naphtha > Distillate > VGO
Major Impact: Catalyst Activity

Na

Caustic
Seawater
Crude
Present in All Fractions
Major Impact: Catalyst Regenerability

Si

Coker Feeds (Anti-Foam Chemicals)

Predominantly in Naphtha Fraction
Major Impact: Catalyst Regenerability

Catalyst Poison Capacities

1.2
1.0

Guard
Catalysts

0.8

60

High
Activity
Guard
Catalysts

High Activity
Catalysts

Si
As

0.6
0.4
0.2

KF-757

KF-901

KF-841

KF-844

KF-859

KG-6

0.0
KF-647

Relative Poison Capacity

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Diesel Hydrotreating Summary (1)

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Feed effects
Endpoint
Cracked stocks
SH-DBT species
Organic nitrogen

Catalyst inhibition
Influencing factors:
Inhibitor molecule
Reactant molecule
Feed oil matrix

Strongest inhibitor: organic nitrogen

Inhibitor adsorption/desorption
Adsorption: fast/strong
Desorption: slow
61

Diesel Hydrotreating Summary (2)

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Color
Complex
Aromatics, Nitrogen Species
Feed Endpoint
High T / Low ppH2 Operation

Aromatics Saturation
Conventional Diesel Hydrotreating
PNAs saturated to mono-aromatics
mono-aromatics not saturated
minimal net reduction of total aromatics

ULSD
PNAs saturated
mono-aromatics saturated
significant net reduction of total aromatics
62

Diesel Hydrotreating Summary (3)

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H2 Consumption
30% - 75% higher
Influences:

Product S level
Catalyst type
Process conditions
Feed characteristics

Avoid Overtreating
Feed Management
Endpoint effects
Cracked stock effects
Match feed properties / unit capabilities
63

Diesel Hydrotreating Summary (4)

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Maximizing Performance
ppH2
H2 Availability
H2 Purity

Feed distribution
Catalyst activity

Catalyst selection - critical concerns

H2 Consumption / H2 Supply balance
Poison control

64