CA1312883C - Process for paraffin isomerization of a distillate range hydrocarbon feedstock - Google Patents
Process for paraffin isomerization of a distillate range hydrocarbon feedstockInfo
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- CA1312883C CA1312883C CA000588005A CA588005A CA1312883C CA 1312883 C CA1312883 C CA 1312883C CA 000588005 A CA000588005 A CA 000588005A CA 588005 A CA588005 A CA 588005A CA 1312883 C CA1312883 C CA 1312883C
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Abstract
A PROCESS FOR PARAFFIN ISOMERIZATION OF A
DISTILLATE RANGE HYDROCARBON FEEDSTOCK
ABSTRACT
A process for paraffinic isomerization of a hydrocarbon feedstock, which has a paraffin content having no more than 20 carbon atoms per molecule, comprises contacting the feedstock with a crystalline aluminosilicate zeolite catalyst having pore openings defined by: (1) a ratio of sorption of n-hexane to o-xylene, on a volume percent basis, of greater than 3, which sorption is determined at a P/Po of 0.1 and at a temperature of 50°C for n-hexane and 80°C for o-xylene and (2) by the ability of selectively cracking 3-methylpentane (3MP) in preference to the doubly branched 2,3-dimethylbutane (DMB) at 540°C (1000°F) and 101 kPa (1 atmosphere) pressure from a 1/1/1 weight ratio mixture of n-hexane/3-methyl-pentane/2,3-dimethylbutane, with the ratio of rate constants k3MP/kDMB determined at a temperature of 540°C
(1000°F) being in excess of 2, e.g., ZSM-22, ZSM-23, ZSM-35 and mixtures thereof. The catalyst is combined with a Group VIII metal, and has a zeolite SiO2/Al2O3 ratio of at least 20:1.
DISTILLATE RANGE HYDROCARBON FEEDSTOCK
ABSTRACT
A process for paraffinic isomerization of a hydrocarbon feedstock, which has a paraffin content having no more than 20 carbon atoms per molecule, comprises contacting the feedstock with a crystalline aluminosilicate zeolite catalyst having pore openings defined by: (1) a ratio of sorption of n-hexane to o-xylene, on a volume percent basis, of greater than 3, which sorption is determined at a P/Po of 0.1 and at a temperature of 50°C for n-hexane and 80°C for o-xylene and (2) by the ability of selectively cracking 3-methylpentane (3MP) in preference to the doubly branched 2,3-dimethylbutane (DMB) at 540°C (1000°F) and 101 kPa (1 atmosphere) pressure from a 1/1/1 weight ratio mixture of n-hexane/3-methyl-pentane/2,3-dimethylbutane, with the ratio of rate constants k3MP/kDMB determined at a temperature of 540°C
(1000°F) being in excess of 2, e.g., ZSM-22, ZSM-23, ZSM-35 and mixtures thereof. The catalyst is combined with a Group VIII metal, and has a zeolite SiO2/Al2O3 ratio of at least 20:1.
Description
A PROCESS FOR PARAFFIN ISOMERIZATIO~ OF A DISTILLATE
R~JGE HYDROCAR~ON FFFDSTOCX
The present invention relates to a process for paraffin isomerization of a distillate range hydrocarbon feedstock.
Various catalytic processes have been proposed for isomerizing n-paraffins so as to lower the pour point of distillate range hydrocarbon feedstocks. ~owever, many available feedstocks contain nitrogen impurities (typically at least 20 ppm) which tend to poison conventional paraffin isomerization catalysts. An object of the present invention is therefore to obviate or alleviate this problem.
Accordingly, the present invention resides in a process for paraffin isomerization of a hydrocarbon feedstock havin~ a boiling range of 165 - 343G and a paraffinic content of molecules with not more than 20 carbon atoms, and preferably no more than 16 carbon atoms, which includes contacting the paraffin-containing feedstock with a crystalline aluminosilicate zeolite catalyst having pore openings defined by: (1) a ratio of sorption of n-hexane to o-xylene, on a volume percent basis, of greater than 3, ~Ihich sorption is determined at a P/PO of 0.1 and at a temperature of 50C for n-hexane and 80C for o-xylene and (2) by the ability of selectively cracking 3-methylpentane (3M~) in preference to the doubly branched 2,3-dimethylbutane (D~) at 540C (1000F) and 101 kPa (1 atmosphere) pressure from a 1/1/1 weight ratio mixture of n-hexane/3-methyl-pentane/2,3-dimethylbutane, with the ratio of rate constants k3Mp/kDMB determined at a temperature of 540C
(1000F) being in excess of 2, said catalyst including a Group VIII
metal, and having a zeolite SiO2/A12O3 ratio of at least 20:1, and said contacting being effected at a temperature of 199 - 454C
(390 to 850F) and a pressure of 790 - 7000 kPa (100 to 1,000 psig).
F-4648 --2-- 1 3 ~ 2 8 8 3 Preferably, said contacting is effected at a pressure of 1~25 - 4240 kPa (250 - 6~0 psig).
The expression, "P/P~, as utilized herein, is accorded its usual si~nificance as described in the literature, for example, in "The nynamical Character of Adsorption" by J.~. dePoer, 2nd ~dition, Oxford University Press (1968) and is the relative pressure defined as the ratio of the partial pressure of sorbate to the vapor pressure of sorbate at the temperature of sorption. The ratio of nts, k3Mp/kDMB, is determined from 1st order kinetics, in the usual manner, by the followin~ equation:
k-(l/Tc)In(~
where k is the rate constant for each component, Tc is the constant time and ~: is the fractional conversion of each component.
The crystalline aluminosilicate zeolite employed in the present invention has pore openings defined by: (1) a ratio of sorption of n-hexane to o-xylene, on a volume percent basis, of greater than 3, which sorption is determined at a P/PO of 0.1 and a temperature of 50C for n-hexane and 80C for o-xylene and (2) hy the ability of selectively cracking 3-methylpentane (3up) in preference to the doubly branched 2,3-dimethylbutane (DMB) at 1000F
and 1 atmosphere pressure from a 1/1/1 weight ratio mixture of n-hexane/3-methyl-pentane/2,3-dimethylbutane, with the ratio of rate constants k3Mp/kDM~ determined at a temperature of 1000F bein~
in excess of 2.
The zeolite catalysts described above are effective for the isomerization of n-paraffins and are resistant to nitrogen poisons, especially those found in distillate range feedstocks, as a result of their specific pore size openings which are effective to exclude most nitrogen containing organic molecules from entering therein.
Inasmuch as ~edium pore zeolites have in the past been considered as somewhat limited for purposes of isomerization as a result of their pore size, the present invention provides an unexpectedly effecient ~312883 procedure and catalyst for effectively isomerizing paraffinic feedstocks, especially in hydrocarbon distillate range feedstock having nitrogen poisons.
The group of medium pore zeolites which can he used in the process of the present invention includes ZSM-2Z, ZSM-23, and Z~SM-35. ZSM-22 is described in U.S. Patent ~o. 4556477, ZSM 23 is described in U.S. Patent ~'o. 4076842 and ZSM-35 is described in U.S.
Patent No. 4Q16245.
The ~roup VIII metals used in the catalyst of the present invention are preferably selected from platinum, palladium, iridium, osmium, rhodium and rhuthenium. The metal is preferably incorporated into the zeolite by ion exchange up to a metal content of 0.01~ to 10~, and preferably from 0.1% to 3~ by weight of the zeolite. The zeolite can be supported in a hinder selected from one of silica, alumina, silica-alumina, and titania.
; l~hen the feedstock is distillate range feedstock, having a boiling point of 165 - 343C (330 to 650F), the catalyst of the present invention has been shown to resist poisoning by nitrogenous compounds under the conditions necessary to isomerize n-paraffins in the feedstock.
Furthermore, a hydrocarbon feedstocX having a substantial paraffinic content can be converted to reduce the boiling point 5-11C (lQ to 20F) without the unwanted side effects of si~nificant cracking which normally results from high temperature, hi~h pressure procedures in the presence of a zeolitic catalyst. As a result, the feedstock can be treated without significan~ reduction of distillate range yield. The product resul~ing from this process contains a significantly grea~er amount of isoparaffinic compounds, i.e., branched hydrocarbon chains, than straight hydrocarbon chains. This is unlike the product resulting from hydrocracking processes which includes a ~reater amount of straight chain molecules.
Consequently, the yield of nonparaffinic distillate is significantly increased.
F-4648 ~~4~~ I 3 1 28~3 Thus, while other procedures have been found to be useful in reducing the paraf~inic content by hydrocrackin~, the present invention has been found to be unexpectedly efficient in reducin~
the n-paraffin content by hydroisomerization while maintaining high distillate ran~e yields.
The following Examples illustrate the invention.
Exam~le 1 (Comparative) The isomerization selectivity of Pt/ZSM-5/A1203 was measured using N-hexadecane at 355Q kPa (500 psig) 277C (531F), H2/HC=13.1 and 1 li~uid hourly space velocity (LHS~'). At 77%
n-C16 conversion, the selectivity (the ratio of the i-C16 yield and the n-C16 conversion) was only 0.30. ~enzoquinoline was then added to the n-C16 feed in an amount to obtain 20 ppm nitro~en.
It was necessary to increase the reactor temperature 30C (54F) to maintain the n-C16 conversion at 77 wt.%. The isomeri2a~ion selectivity increased to 0.43.
Fxample 2 The isomerization selectivity of Pt/Z~-22/A12O3 was measured as described in Fxample 1. 85 wt.% conversion of n-C16 was obtained at 302C (576F) and the isomerization selectivity was 0.76. When 20 ppm nitrogen was added as benzoquinoline, the reactor temperature was increased 29C (52F) to maintain conversion, no change in isomerization selectivity was observed. Thus this catalyst showed better isomerization selectivity compared to ZSM-5 for a clean feed and in the presence of a nitrogen poison.
Example_3 The performance of Pt/ZS~-23/A12O3 for isomerization was tested as described in Example l. At 320C (60~F), 6a wt.%
conversion of n-C16 was observed with 0.60 isomerization selectivity. The reactor temperat~re was increased only 20C (36F) to maintain the n-C16 conversion after benzoquinoline was added.
This catalyst shows higher isomerization selectivity and better nitrogen resistance compared to Pt/ZSM-5/~1203 in Example 1.
F-4648 --5-~
Example 4 Pt/ZSM-35/~1203 was used to isomerize n-C16 at the condi~ions described in F~ample 1. 76 wt.% n-C16 conversion was observed at 307C (585F) with 0~50 isomerization selectivity. hhen 20 ppm nitrogen as benzoquinoline was added the reactor temperature was increased by 60C (lORF) to maintain conversion, however, the isomerization selectivity increased to 0.70. Although a larger temperataure increase was required to maintain n-C16 conversion activity compared to Pt/ZSM-5/A1203, the isomerization selectivity was much higher for Pt/ZSM-35/A1203 for a clean feed and for a feed containing nitrogen.
The results of the above Examples are summarized in Table 1 below.
TABLE I
lC
Example l Example 2 Fxample 3 Fxa~ple 4 n-C16 Conversion 77% 85% 69% 76%
w/o Nitrogen n-C16 ,onversion 77% 85% 69% 76%
w/ Nitrogen i-C16* Selectivity 0.30 0.76 0.60 Q.50 w/o Nitrogen i-C16* Selectivity 0.43 0.76 0.60 0.70 w/ Nitrogen . _ *Isomerization selectivity is defined as the ratio of the i-C16 yield to the n-C16 conversion.
R~JGE HYDROCAR~ON FFFDSTOCX
The present invention relates to a process for paraffin isomerization of a distillate range hydrocarbon feedstock.
Various catalytic processes have been proposed for isomerizing n-paraffins so as to lower the pour point of distillate range hydrocarbon feedstocks. ~owever, many available feedstocks contain nitrogen impurities (typically at least 20 ppm) which tend to poison conventional paraffin isomerization catalysts. An object of the present invention is therefore to obviate or alleviate this problem.
Accordingly, the present invention resides in a process for paraffin isomerization of a hydrocarbon feedstock havin~ a boiling range of 165 - 343G and a paraffinic content of molecules with not more than 20 carbon atoms, and preferably no more than 16 carbon atoms, which includes contacting the paraffin-containing feedstock with a crystalline aluminosilicate zeolite catalyst having pore openings defined by: (1) a ratio of sorption of n-hexane to o-xylene, on a volume percent basis, of greater than 3, ~Ihich sorption is determined at a P/PO of 0.1 and at a temperature of 50C for n-hexane and 80C for o-xylene and (2) by the ability of selectively cracking 3-methylpentane (3M~) in preference to the doubly branched 2,3-dimethylbutane (D~) at 540C (1000F) and 101 kPa (1 atmosphere) pressure from a 1/1/1 weight ratio mixture of n-hexane/3-methyl-pentane/2,3-dimethylbutane, with the ratio of rate constants k3Mp/kDMB determined at a temperature of 540C
(1000F) being in excess of 2, said catalyst including a Group VIII
metal, and having a zeolite SiO2/A12O3 ratio of at least 20:1, and said contacting being effected at a temperature of 199 - 454C
(390 to 850F) and a pressure of 790 - 7000 kPa (100 to 1,000 psig).
F-4648 --2-- 1 3 ~ 2 8 8 3 Preferably, said contacting is effected at a pressure of 1~25 - 4240 kPa (250 - 6~0 psig).
The expression, "P/P~, as utilized herein, is accorded its usual si~nificance as described in the literature, for example, in "The nynamical Character of Adsorption" by J.~. dePoer, 2nd ~dition, Oxford University Press (1968) and is the relative pressure defined as the ratio of the partial pressure of sorbate to the vapor pressure of sorbate at the temperature of sorption. The ratio of nts, k3Mp/kDMB, is determined from 1st order kinetics, in the usual manner, by the followin~ equation:
k-(l/Tc)In(~
where k is the rate constant for each component, Tc is the constant time and ~: is the fractional conversion of each component.
The crystalline aluminosilicate zeolite employed in the present invention has pore openings defined by: (1) a ratio of sorption of n-hexane to o-xylene, on a volume percent basis, of greater than 3, which sorption is determined at a P/PO of 0.1 and a temperature of 50C for n-hexane and 80C for o-xylene and (2) hy the ability of selectively cracking 3-methylpentane (3up) in preference to the doubly branched 2,3-dimethylbutane (DMB) at 1000F
and 1 atmosphere pressure from a 1/1/1 weight ratio mixture of n-hexane/3-methyl-pentane/2,3-dimethylbutane, with the ratio of rate constants k3Mp/kDM~ determined at a temperature of 1000F bein~
in excess of 2.
The zeolite catalysts described above are effective for the isomerization of n-paraffins and are resistant to nitrogen poisons, especially those found in distillate range feedstocks, as a result of their specific pore size openings which are effective to exclude most nitrogen containing organic molecules from entering therein.
Inasmuch as ~edium pore zeolites have in the past been considered as somewhat limited for purposes of isomerization as a result of their pore size, the present invention provides an unexpectedly effecient ~312883 procedure and catalyst for effectively isomerizing paraffinic feedstocks, especially in hydrocarbon distillate range feedstock having nitrogen poisons.
The group of medium pore zeolites which can he used in the process of the present invention includes ZSM-2Z, ZSM-23, and Z~SM-35. ZSM-22 is described in U.S. Patent ~o. 4556477, ZSM 23 is described in U.S. Patent ~'o. 4076842 and ZSM-35 is described in U.S.
Patent No. 4Q16245.
The ~roup VIII metals used in the catalyst of the present invention are preferably selected from platinum, palladium, iridium, osmium, rhodium and rhuthenium. The metal is preferably incorporated into the zeolite by ion exchange up to a metal content of 0.01~ to 10~, and preferably from 0.1% to 3~ by weight of the zeolite. The zeolite can be supported in a hinder selected from one of silica, alumina, silica-alumina, and titania.
; l~hen the feedstock is distillate range feedstock, having a boiling point of 165 - 343C (330 to 650F), the catalyst of the present invention has been shown to resist poisoning by nitrogenous compounds under the conditions necessary to isomerize n-paraffins in the feedstock.
Furthermore, a hydrocarbon feedstocX having a substantial paraffinic content can be converted to reduce the boiling point 5-11C (lQ to 20F) without the unwanted side effects of si~nificant cracking which normally results from high temperature, hi~h pressure procedures in the presence of a zeolitic catalyst. As a result, the feedstock can be treated without significan~ reduction of distillate range yield. The product resul~ing from this process contains a significantly grea~er amount of isoparaffinic compounds, i.e., branched hydrocarbon chains, than straight hydrocarbon chains. This is unlike the product resulting from hydrocracking processes which includes a ~reater amount of straight chain molecules.
Consequently, the yield of nonparaffinic distillate is significantly increased.
F-4648 ~~4~~ I 3 1 28~3 Thus, while other procedures have been found to be useful in reducing the paraf~inic content by hydrocrackin~, the present invention has been found to be unexpectedly efficient in reducin~
the n-paraffin content by hydroisomerization while maintaining high distillate ran~e yields.
The following Examples illustrate the invention.
Exam~le 1 (Comparative) The isomerization selectivity of Pt/ZSM-5/A1203 was measured using N-hexadecane at 355Q kPa (500 psig) 277C (531F), H2/HC=13.1 and 1 li~uid hourly space velocity (LHS~'). At 77%
n-C16 conversion, the selectivity (the ratio of the i-C16 yield and the n-C16 conversion) was only 0.30. ~enzoquinoline was then added to the n-C16 feed in an amount to obtain 20 ppm nitro~en.
It was necessary to increase the reactor temperature 30C (54F) to maintain the n-C16 conversion at 77 wt.%. The isomeri2a~ion selectivity increased to 0.43.
Fxample 2 The isomerization selectivity of Pt/Z~-22/A12O3 was measured as described in Fxample 1. 85 wt.% conversion of n-C16 was obtained at 302C (576F) and the isomerization selectivity was 0.76. When 20 ppm nitrogen was added as benzoquinoline, the reactor temperature was increased 29C (52F) to maintain conversion, no change in isomerization selectivity was observed. Thus this catalyst showed better isomerization selectivity compared to ZSM-5 for a clean feed and in the presence of a nitrogen poison.
Example_3 The performance of Pt/ZS~-23/A12O3 for isomerization was tested as described in Example l. At 320C (60~F), 6a wt.%
conversion of n-C16 was observed with 0.60 isomerization selectivity. The reactor temperat~re was increased only 20C (36F) to maintain the n-C16 conversion after benzoquinoline was added.
This catalyst shows higher isomerization selectivity and better nitrogen resistance compared to Pt/ZSM-5/~1203 in Example 1.
F-4648 --5-~
Example 4 Pt/ZSM-35/~1203 was used to isomerize n-C16 at the condi~ions described in F~ample 1. 76 wt.% n-C16 conversion was observed at 307C (585F) with 0~50 isomerization selectivity. hhen 20 ppm nitrogen as benzoquinoline was added the reactor temperature was increased by 60C (lORF) to maintain conversion, however, the isomerization selectivity increased to 0.70. Although a larger temperataure increase was required to maintain n-C16 conversion activity compared to Pt/ZSM-5/A1203, the isomerization selectivity was much higher for Pt/ZSM-35/A1203 for a clean feed and for a feed containing nitrogen.
The results of the above Examples are summarized in Table 1 below.
TABLE I
lC
Example l Example 2 Fxample 3 Fxa~ple 4 n-C16 Conversion 77% 85% 69% 76%
w/o Nitrogen n-C16 ,onversion 77% 85% 69% 76%
w/ Nitrogen i-C16* Selectivity 0.30 0.76 0.60 Q.50 w/o Nitrogen i-C16* Selectivity 0.43 0.76 0.60 0.70 w/ Nitrogen . _ *Isomerization selectivity is defined as the ratio of the i-C16 yield to the n-C16 conversion.
Claims (7)
1. A process for paraffin isomerization of a distillate range hydrocarbon feedstock having a boiling range of 165 - 343°C
(330 - 650°F) and a paraffinic content of molecules with not more than 20 carbon atoms, comprising:
contacting said paraffin-containing feedstock with a catalyst including a crystalline zeolite catalyst having pore openings defined by: (1) a ratio of sorption of n hexane to o-xylene, on a volume percent basis, of greater than 3, which sorption is determined at a P/Po of 0.1 and at a temperature of 50°C for n-hexane and 80°C for o-xylene and (2) by the ability of selectively cracking 3-methylpentane (3MP) in preference to the
(330 - 650°F) and a paraffinic content of molecules with not more than 20 carbon atoms, comprising:
contacting said paraffin-containing feedstock with a catalyst including a crystalline zeolite catalyst having pore openings defined by: (1) a ratio of sorption of n hexane to o-xylene, on a volume percent basis, of greater than 3, which sorption is determined at a P/Po of 0.1 and at a temperature of 50°C for n-hexane and 80°C for o-xylene and (2) by the ability of selectively cracking 3-methylpentane (3MP) in preference to the
2,3dimethylbutane (DMB) at 540°C (1000°F) and 101 kPa (1 atmosphere) pressure from a 1/1/1 weight ratio mixture of n-hexane/3-methyl-pentane/2,3dimethylbutane (DMB), with the ratio rate constants k3Mp/kDMB determined at a temperature of 540°C
(1000°F) being in excess of 2, said catalyst including a Group VIII
metal, and having a zeolite SiO2/Al2O3 ratio of at least 20:1, and said contacting being effected at a temperature of 199 - 454°C
(390 to 850°F) and a pressure of 790 - 7000 kPa (100 to 1,000 psig).
2. The process of Claim 1 wherein said crystalline aluminosilicate catalyst is selected from ZSM-22, ZSM-23 and ZSM-35.
(1000°F) being in excess of 2, said catalyst including a Group VIII
metal, and having a zeolite SiO2/Al2O3 ratio of at least 20:1, and said contacting being effected at a temperature of 199 - 454°C
(390 to 850°F) and a pressure of 790 - 7000 kPa (100 to 1,000 psig).
2. The process of Claim 1 wherein said crystalline aluminosilicate catalyst is selected from ZSM-22, ZSM-23 and ZSM-35.
3. The process of Claim 2 wherein said Group VIII metal is selected from Pt, Pd, Ir, Os, Rh and Pu.
4. The process of Claim 1 wherein said metal is incorporated into said zeolite by ion exchange to a metal content in the range of 0.01% to 10.0% by weight.
5. The process of Claim 4 wherein said metal content is from 0.1% to 3.0% by weight.
6. The process of Claim 1, 2, 3, 4 or 5 wherein said zeolite is supported in a binder selected from silica, alumina, silica-alumina, and titania.
7. The process of Claim 1, 2, 3, 4 or 5 wherein said paraffin content has molecules of no greater than 16 carbon atoms.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000588005A CA1312883C (en) | 1987-12-28 | 1989-01-11 | Process for paraffin isomerization of a distillate range hydrocarbon feedstock |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/138,749 US4814543A (en) | 1987-12-28 | 1987-12-28 | Nitrogen resistant paraffin hydroisomerization catalysts |
| CA000588005A CA1312883C (en) | 1987-12-28 | 1989-01-11 | Process for paraffin isomerization of a distillate range hydrocarbon feedstock |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1312883C true CA1312883C (en) | 1993-01-19 |
Family
ID=25672372
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000588005A Expired - Fee Related CA1312883C (en) | 1987-12-28 | 1989-01-11 | Process for paraffin isomerization of a distillate range hydrocarbon feedstock |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA1312883C (en) |
-
1989
- 1989-01-11 CA CA000588005A patent/CA1312883C/en not_active Expired - Fee Related
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