Claims
- 1. A process of making a modified alkylbenzene sulfonate comprising the steps of:a) passing a feed stream containing C8-C28 paraffins to an isomerization zone, operating the isomerization zone at isomerization conditions sufficient to isomerize paraffins and recovering from the isomerization zone an isomerized product stream comprising paraffins; b) passing at least a portion of said isomerized product stream admixed with a diluent material of hydrogen such that there is a hydrogen to hydrocarbon mole ratio of about 0.1:1 to about 40:1; to a dehydrogenation zone, operating the dehydrogenation zone at dehydrogenation conditions sufficient to dehydrogenate paraffins, and recovering from the dehydrogenation zone a dehydrogenated product stream comprising linear olefins, branched monoolefins and paraffins, wherein the branched monoolefins have from about 8 to about 28 carbon atoms and wherein at least a portion of the branched monoolefins in the dehydrogenated product stream comprise lightly branched monoolefins, wherein at least 70 mol % of the total lightly branched monoolefins have 3 or 4 primary carbon atoms and no quaternary carbon atoms; c) passing an aryl compound and at least a portion of the dehydrogenated product stream comprising branched monoolefins to an alkylation zone, operating the alkylation zone at alkylation conditions sufficient to alkylate the aryl compound with branched monoolefins in the presence of an alkylation catalyst to form arylalkane molecules having one aryl portion and one aliphatic alkyl portion containing from about 8 to about 28 carbon atoms; wherein at least a portion of the arylalkane molecules formed in the alkylation zone have 2, 3, or 4 primary carbon atoms, and no quaternary carbon atoms except for any quaternary carbon atom bonded by a carbon-carbon bond with a carbon atom of the aryl portion; and wherein the alkylation has a selectivity to 2-phenyl-alkanes of from 40 to 100 and a selectivity to internal quaternary phenyl-alkanes of less than 10; d) recovering from the alkylation zone an alkylate product stream comprising the aryl-alkane molecules and a recycle stream comprising paraffins; e) passing at least a portion of the recycle stream to the isomerization zone or the dehydrogenation zone; f) sulfonating said alkylate product stream to produce a sulfonated alkyl product stream; and g) optionally, neutralizing said sulfonated alkyl product stream to produce the modified alkylbenzene sulfonate with an average alkyl carbon chain length of from about 10 to about 14.
- 2. The process of claim 1 wherein at least a portion of the isomerized product stream, at least a portion of the dehydrogenated product stream, and at least a portion of the recycle stream comprise paraffins having from about 8 to about 28 carbon atoms.
- 3. The process of claim 2 wherein at least a portion of the paraffins in at least a portion of the isomerized product stream, at least a portion of the dehydrogenated product stream, and at least a portion of the recycle stream comprise 3 or 4 primary carbon atoms and no quaternary carbon atoms.
- 4. The process of claim 3 wherein at least a portion of the isomerized product stream comprises a concentration of paraffins of greater than about 25 mol-% having 3 or 4 primary carbon atoms and no quaternary carbon atoms.
- 5. The process of claim 2 wherein at least a portion of the paraffins in at least a portion of the isomerized product stream, at least a portion of the dehydrogenated product stream, and at least a portion of the recycle stream comprise secondary carbon atoms having 2 primary carbon atoms.
- 6. The process of claim 5 wherein at least a portion of the isomerized product stream has a concentration of less than about 75 mol-% paraffins comprising secondary carbon atoms and 2 primary carbon atoms.
- 7. The process of claim 2 wherein the isomerized product stream has a concentration of less than about 10 mol-% of paraffins, wherein at least a portion of the dehydrogenated product stream and at least a portion of the recycle stream comprise at least one quaternary carbon atom.
- 8. The process of claim 1 wherein the isomerization zone comprises an isomerization catalyst comprising a Group VIII (IUPAC 8-10) metal and a support material selected from the group consisting of amorphous alumina, amorphous silica-alumina, ferrierite, ALPO-31, SAPO-11, SAPO-31, SAPO-37, SAPO-41, SM-3, and MgAPSO-31.
- 9. The process of claim 1 wherein said isomerization zone operates at isomerization conditions comprising a temperature of from about 50 to about 400° C. and a molar ratio of hydrogen per hydrocarbon of greater than about 0.01:1.
- 10. The process of claim 1 wherein the dehydrogenation zone comprises a dehydrogenation catalyst comprising at least one Group VIII (IUPAC 8-10) metal, a promoter metal, a modifier metal, and a refractory inorganic oxide.
- 11. The process of claim 10 wherein the dehydrogenation catalyst comprises an inner core and an outer layer bonded to the inner core, the outer layer comprising an outer refractory inorganic oxide having uniformly dispersed thereon at least one Group VIII (IUPAC 8-10) metal and the promoter metal, and said dehydrogenation catalyst further having dispersed thereon the modifier metal.
- 12. The process of claim 11 herein the outer layer is bonded to the inner core of the dehydrogenation catalyst such that the attrition loss is less than about 10 wt-% based on the weight of the outer layer.
- 13. The process of claim 1 wherein the dehydrogenation zone operates at dehydrogenabon conditions comprising a temperature of from about 400 to about 525° C. and a pressure of less than about 345 kPa(g).
- 14. The process of claim 1 wherein the alkylation catalyst comprises a zeolite having a zeolite structure type selected from the group consisting of BEA, MOR, MTW and NES.
- 15. The process of claim 1 wherein the aryl compound comprises a compound selected from the group consisting of benzene, toluene, ethylbenzene and mixtures thereof.
- 16. The process of claim 1 wherein the monooletins comprise from 10 to 15 carbon atoms.
- 17. The process of claim 1 wherein the arylalkane molecule comprises an aliphatic alkyl portion from 10 to 15 carbon atoms.
- 18. The process of claim 1 wherein the lightly branched monoolefins comprise monomethyl-alkenes.
- 19. The process of claim 1 wherein the arylalkanes comprise monomethyl-phenyl-alkanes.
- 20. The process of claim 1 wherein at least a portion of the recycle stream comprises a concentration of monoolefins of less than about 0.3 wt-%.
- 21. The process of claim 1 wherein the dehydrogenated product stream has a first concentration of diolefins, at least a portion of the dehydrogenated product stream passes to a selective diolefin hydrogenation zone, a selective dioletin hydrogenation product stream having a second concentration of diolefins that is less than the first concentration of diolefins is recovered from the selective diolefin hydrogenation zone, and at least a portion of the selective diolefin hydrogenation product stream passes to the alkylation zone.
- 22. The process of claim 21 wherein the selective diolefin hydrogenation product stream has a first concentration of aromatic by-products, at least a portion of the selective diolefin hydrogenation product stream passes to an aromatics removal zone, an aromatics removal product stream having a second concentration of aromatic by-products that is less than the first concentration of aromatic by-products is recovered from the aromatics removal zone, and at least a portion of the aromatics removal product stream passes to the alkylation zone.
- 23. The process of claim 1 wherein the dehydrogenated product stream has a first concentration of aromatic by-products, at least a portion of the dehydrogenated product stream passes to an aromatics removal zone, an aromatics removal product stream having a second concentration of aromatic by-products that is less than the first concentration of aromatic by-products is recovered from the aromatics removal zone, and at least a portion of the aromatics removal product stream passes to the alkylation zone.
- 24. The process of claim 1 wherein at least a portion of the recycle stream passes to the isomerization zone.
- 25. The process of claim 24 wherein the isomerization zone contains a first bed containing isomerization catalyst and a second bed containing isomerization catalyst, the feed stream passes to the first bed operating at first bed conditions to isomerize paraffins, a first bed effluent comprising paraffins is withdrawn from the first bed, at least a portion of the first bed effluent and the at least a portion of the recycle stream passes to the second bed operating at second bed conditions to isomerize paraffins, and the isomerized product stream is recovered from the second bed.
- 26. The process of claim 1 wherein at least a portion of the recycle stream passes to the dehydrogenation zone.
- 27. The process of claim 26 wherein the dehydrogenation zone contains a first bed containing dehydrogenation catalyst and a second bed containing dehydrogenation catalyst, the at least a portion of the isomerized product stream passes to the first bed operating at first bed conditions to dehydrogenate paraffins, a first bed effluent comprising paraffins is withdrawn from the first bed, at least a portion of the first bed effluent and the at least a portion of the recycle stream passes to the second bed operating at second bed conditions to dehydrogenate paraffins, and the dehydrogenated product stream is recovered from the second bed.
- 28. The process of claim 1 wherein at least a portion of the isomerized product stream comprises paraffins having from about 8 to about 28 carbon atoms and the carbon atoms of the paraffins in the isomerized product stream comprise 3 or 4 primary carbon atoms and no quaternary carbon atoms.
- 29. The process of claim 1 wherein at least a portion of the alkylate product stream is contacted with a sulfonating agent at sulfonating conditions sufficient to sulfonate the arylalkane molecules and to produce a sulfonated product stream comprising arylalkane sulfonic acids, wherein the sulfonating agent is selected from the group consisting of sulfuric acid, chlorosulfonic acid, oleum and sulfur trioxide.
- 30. The process of claim 29 wherein at least a portion of the sulfonated product stream is contacted with a neutralizing agent at neutralizing conditions sufficient to neutralize the arylalkane sulfonic acids and to produce a neutralized product stream comprising arylalkane sulfonates, wherein the neutralizing agent is selected from the group consisting of sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium carbonate, sodium bicarbonate, potassium carbonate, magnesium hydroxide, magnesium carbonate, basic magnesium carbonate (magnesium alba), calcium hydroxide, calcium carbonate, and mixtures thereof.
- 31. A process of making a modified alkylbenzene sulfonate comprising the steps of:a) passing a feed stream containing paraffins to an isomerization zone, operating the isomerization zone at isomerization conditions sufficient to isomerize paraffins, and recovering from the isomerization zone an isomerized product stream comprising paraffins; b) passing at least a portion of said isomerized product stream admixed with a diluent material of hydrogen such that there is a hydrogen to hydrocarbon mole ratio of about 0.1:1 to about 40:1; to a dehydrogenation zone, operating the dehydrogenation zone at dehydrogenation conditions sufficient to dehydrogenate paraffins, and recovering from the dehydrogenation zone a dehydrogenated product stream comprising linear olefins, branched monoolefins and paraffins, wherein the branched monoolefins having from about 8 to about 28 carbon atoms and wherein at least a portion of the branched monoolefins in the dehydrogenated product stream comprise lightly branched monoolefins having 3 or 4 primary carbon atoms and no quaternary carbon atoms: c) passing an aryl compound and at least a portion of the dehydrogenated product stream comprising branched monoolefins to an alkylation zone, operating the alkylation zone at alkylation conditions sufficient to alkylate the aryl compound with branched monoolefins in the presence of an alkylation catalyst to form arylalkanes molecules having one aryl group and one aliphatic alkyl group, wherein the arylalkane molecules have: 1) an average weight of the aliphatic alkyl groups of the arylakane molecules of between the weight of a C10 aliphatic alkyl group and a C13 aliphatic alkyl group; 2) a content of the arylakane molecules having the phenyl group attached to the 2- and/or 3-position of the aliphatic alkyl group of greater than 55 wt-% of the arylakane molecules; and 3) an average level of branching of the aliphatic alkyl groups of the arylakane molecules of from 0.25 to 1.4 alkyl group branches per arylalkane molecules when the sum of the contents of 2-phenyl-alkanes and 3-phenyl-alkanes is more than 55 wt-% and less than or equal to 85 wt-% of the arylakane molecules, or an average level of branching of the aliphatic alkyl groups of the arylakane molecules of from 0.4 to 2.0 alkyl group branches per arylalkane molecule when the sum of the concentrations of 2-phenyl-alkanes and 3-phenyl-alkanes is greater than 85 wt-% of the arylakane molecules; and wherein the aliphatic alkyl groups of the arylakane molecules comprise linear aliphatic groups, mono-branched aliphatic alkyl groups, or di-branched aliphatic alkyl groups, and wherein the alkyl group branches, if any on the aliphatic alkyl chain of the aliphatic alkyl groups, comprise methyl group branches, ethyl group branches, or propyl group branches, and wherein the alkyl group branches, if any attach to any position on the aliphatic alkyl chain of the of the aliphatic alkyl groups provided that arylalkanes having at least one quaternary carbon atom, comprise less than 20% of the arylakane molecules; d) recovering from the alkylation zone an alkylate product stream comprising the arylakane molecules and a recycle stream comprising paraffins; e) passing at least a portion of the recycle stream to the isomerization zone or the dehydrogenation zone; f) sulfonating said alkylate product stream to produce a sulfonated alkyl product stream; and g) optionally, neutralizing said sulfonated alkyl product stream.
- 32. The process of claim 31 wherein at least a portion of the alkylate product stream is contacted with a sulfonating agent at sulfonating conditions sufficient to sulfonate arylalkanes and to produce a sulfonated product stream comprising arylalkane sulfonic acids, wherein the sulfonating agent is selected from the group consisting of sulfuric acid, chlorosulfonic acid, oleum, and sulfur trioxide.
- 33. The process of claim 31 wherein at least a portion of the sulfonated product stream is contacted with a neutralizing agent at neutralizing conditions sufficient to neutralize arylalkane sulfonic acids and to produce a neutralized product stream comprising arylalkane sulfonates, wherein the neutralizing agent is selected from the group consisting of sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium carbonate, sodium bicarbonate, potassium carbonate, magnesium hydroxide, magnesium carbonate, basic magnesium carbonate (magnesium alba), calcium hydroxide, calcium carbonate, and mixtures thereof.
Parent Case Info
This application claims the benefit of Provisional application No. 60/144,519, filed Jul. 19, 1991.
PCT Information
Filing Document |
Filing Date |
Country |
Kind |
PCT/US00/19647 |
|
WO |
00 |
Publishing Document |
Publishing Date |
Country |
Kind |
WO01/05755 |
1/25/2001 |
WO |
A |
Foreign Referenced Citations (3)
Number |
Date |
Country |
WO 99 05082 |
Feb 1999 |
WO |
WO 99 05243 |
Feb 1999 |
WO |
WO 99 05244 |
Feb 1999 |
WO |
Provisional Applications (1)
|
Number |
Date |
Country |
|
60/144519 |
Jul 1999 |
US |