1. Petrochemical Technology (TKK-2130)
16/17 Spring Semester
Petrochemical Technology (TKK-2130)
Instructor: Rama Oktavian
Office Hr.: M.10-15, Tu , W , Th , F

2. Aromatic compound

3. Aromatic compound

4. Aromatic compound

5. Aromatic compound

6. Aromatic compound

7. Aromatic compound Benzene
a cyclical, six carbon, six hydrogen molecule
a clear, colourless, volatile liquid with a characteristic ‘aromatic’ smell

8. Aromatic compound Benzene

9. Aromatic compound Benzene uses
combined and processed with other basic chemicals (such as ethylene or propylene) to produce countless consumer goods
The largest derivative outlet for benzene is ethylbenzene
production of styrene
polystyrene
widely used to produce cumene
Phenol, cyclohexane, and aniline

10. Aromatic compound
Benzene uses

11. Aromatic compound Benzene global demand

12. Aromatic compound Benzene uses

13. Aromatic compound Benzene uses

14. Aromatic compound Benzene global demand
According to a new IHS Chemical (NYSE: IHS) global market study, global demand for benzene, an aromatic hydrocarbon and one of the primary chemical building blocks for the petrochemical industry, increased to 43.7 million metric tons in 2013, an increase of 2.8 percent above demand for benzene in 2012.

15. Aromatic compound Benzene demands

16. Aromatic compound Benzene sources

17. Aromatic compound Benzene sources

18. Aromatic compound

19. Aromatic compound Benzene production Hydrodealkylation
Extractive distillation
Catalytic reforming
Toluene dismutation and disproportionation
Pyrolysis gasoline
Production from coal tar

20. Benzene production Hydrodealkylation
This method is used to produce benzene from toluene
Reaction involves:
Development: Catalytic hydrodealkylation process using chromium oxide based catalyst

21. Benzene production
Hydrodealkylation

22. Benzene production
Hydrodealkylation

23. Benzene production Toluene dismutation
This technique, whose industrial development is recent, serves to increase the availability of benzene and of mixed xylenes, at the expense of toluene.
the Friedel-Crafts type, silica aluminas, dual-functional or zeolites.
The main reaction is the following:

24. Benzene production
Toluene dismutation
Vapor phase process

25. Benzene production Extractive distillation

26. Benzene production Catalytic reforming
Reforming takes straight chain hydrocarbons in the C6 to C8 range from the gasoline or naphtha fractions and rearranges them into compounds containing benzene rings
A typical catalyst is a mixture of platinum and aluminium oxide

27. Benzene production
Catalytic reforming

28. Benzene production Production from pyrolysis gasoline
Pyrolysis gasoline is the by-product of steam cracking of paraffin gases, naphtha, gas oils and other hydrocarbons used to make ethylene.
It contains 60% aromatics, 50% of which is benzene

29. Ethylbenzene production

30. Ethylbenzene production
Process chemistry

31. Ethylbenzene production

32. Aromatic compound Toluene = methylbenzene

33. Aromatic compound
Toluene uses

34. Aromatic compound
Toluene uses

35. Toluene Toluene consumption

36. Toluene Toluene consumption

37. Toluene
Toluene production technology

38. Toluene
Toluene production technology

39. Aromatic compound Toluene production process
In the cat reforming process, two important variables control toluene make: the composition of the feed and the operating conditions in the reactor. As to the first, some compounds are more suitable for reforming into toluene than others. These precursors (from the Latin, curro, “I run,” and pre, “before”) include ethyl cyclopentane, methyl cyclohexane, and dimethyl cyclopentane

40. Aromatic compound Toluene production process
Azeotropic distillation of toluene

41. Toluene Toluene to benzene production technology
Toluene hydrodealkylation
The hydrodealkylation is conducted either purely thermally at °C and bar or catalytically at somewhat lower temperatures of °C and bar Over Cr2O3, Mo2O3, or CoO on supports (e.g., Al2O3) or, as in a recent development, at °C over Rh/Al2O3.

42. Toluene Toluene to benzene production technology
Toluene disproportionation
2 toluene molecules are reacted and the methyl groups rearranged from one toluene molecule to the other, yielding one benzene molecule and one xylene molecule

43. Toluene Toluene to TDI production process
Toluene diisocyanate (TDI) is currently produced via a three-step process:
Nitration of toluene to dinitrotoluene (DNT)
Toluene is nitrated in two steps, producing the three isomers of mononitrotoluene. and the mixed mononitrotoluene isomers are further nitrated resulting in dinitrotoluene isomers
Reduction of dinitrotoluene to toluene diamine (TDA)
Dinitrotoluene is dissolved in methanol and reduced continuously by reaction with hydrogen in the presence of a suitable catalyst

44. Toluene Toluene to TDI production process
Toluene diisocyanate (TDI) is currently produced via a three-step process:
Phosgenation of TDA to TDI
The 80/20 TDA produced by any of the above processes is converted to diisocyanate by reaction with phosgene
phosgene

45. Aromatic compound TDI uses
As raw material for flexible polyurethane (PU) foam used in furniture, mattresses and car seats.
rigid foams and adhesives, paints, concrete sealers, as a cross-linking agent for nylon 6, and as an intermediate in PU coatings and elastomers

46. Aromatic compound Xylene
the o- isomer has the IUPAC name of 1,2-dimethylbenzene
the m- isomer has the IUPAC name of 1,3-dimethylbenzene
the p- isomer has the IUPAC name of 1,4-dimethylbenzene

47. Aromatic compound Xylene Properties
The melting point ranges from −47.87 °C (−54.17 °F) (m-xylene) to °C (55.87 °F) (p-xylene)
The boiling point for each isomer is around 140 °C ( °F)
The density of each is around 0.87 g/mL (7.26 lb/U.S. gallon)
Xylene in air can be smelled at 0.08 to 3.7 parts of xylene per million parts of air (ppm)

48. Aromatic compound
Xylene uses

49. Aromatic compound
Xylene production

50. Toluene Toluene to xylene production technology
Toluene disproportionation
2 toluene molecules are reacted and the methyl groups rearranged from one toluene molecule to the other, yielding one benzene molecule and one xylene molecule

51. Toluene Xylene separation process technology
Too much effort for xylene separation in distillation column.
Cryogenic crystallization was introduced since their freezing point is not close

52. Toluene
Xylene separation process technology
Cryogenic crystallization

53. Toluene Xylene separation process technology
Molecular sieve adsorption

54. Toluene
Xylene isomerization technology

55. Aromatic compound Recent update Developing technologies
China Petroleum and Chemical Corporation (CPCC) and Sinopec have developed a new composite solvent for extractive distillation (ED) of aromatics.
ExxonMobil proposes a bound zeolite catalyst for use in alkylation, transalkylation or isomerization of aromatic hydrocarbons.
UOP has developed a new family of zeolites that can be used in alkylation of aromatics, transalkylation of aromatics, isomerization of aromatics and alkylation of isoparaffins.

56. Aromatic compound Recent update
Catalyst development in aromatic hydrocarbon production using catalytic pyrolysis
1. Aromatic hydrocarbons production from ex situ catalysis of pyrolysis vapor over Zinc modified ZSM-5 in a packed-bed catalysis coupled with microwave pyrolysis reactor, published in Fuel Volume 129, 1 August 2014, Pages 78–85

57. Aromatic compound Recent update
Catalyst development in aromatic hydrocarbon production using catalytic pyrolysis from biomass
1. Production of aromatic hydrocarbons by catalytic pyrolysis of microalgae with zeolites: Catalyst screening in a pyroprobe, published in Bioresource Technology Volume 139, July 2013, Pages 397–401

58. Aromatic compound Recent update
Catalyst development in aromatic hydrocarbon production using catalytic pyrolysis from biomass
2. Production of aromatic hydrocarbons through catalytic pyrolysis of 5-Hydroxymethylfurfural from biomass, published in Bioresource Technology Volume 147, November 2013, Pages 37–42

59. Aromatic compound Recent update
Catalyst development in aromatic hydrocarbon production using catalytic pyrolysis from biomass
3. Production of Light Aromatic Hydrocarbons from Biomass by Catalytic Pyrolysis, published in Chinese Journal of Catalysis Volume Volume 29, Issue 9, September 2008, Pages 907–912

60. Thank You !