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US3312750A - Hydrodesulfurization of crude alpha-pinene - Google Patents

Hydrodesulfurization of crude alpha-pinene Download PDF

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US3312750A
US3312750A US317806A US31780663A US3312750A US 3312750 A US3312750 A US 3312750A US 317806 A US317806 A US 317806A US 31780663 A US31780663 A US 31780663A US 3312750 A US3312750 A US 3312750A
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pinene
crude
sulfur
alpha
hydrogen
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Berg Lloyd
Isaacson William Bruce
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
    • C07C7/163—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by hydrogenation
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S585/00—Chemistry of hydrocarbon compounds
    • Y10S585/929—Special chemical considerations
    • Y10S585/947—Terpene manufacture or recovery

Definitions

  • This invention relates to the hydrodesulfurizationof crude alpha-pinene, and more particularly, to a process for removing sulfur compounds from crude alpha-pinene by means of a catalytic hydrogenation.
  • the furnace flue gases generally contain a relatively small concentration of the malodorous'substances; however, the total volume of discharge is so great that a considerable nuisance may result.
  • Condensates from the multiple-effect evaporator on the black liquor recovery system may contain a consider'able amount of the foul-smelling compounds, thus giving rise to a secondary nuisance.
  • the gases liberated in relieving and blowing the digesters are a major source for the foul odors associated with the kraft mill.
  • crude sulfate turpentine If the gases evolved from the digester relief valve are condensed, the material obtained is called crude sulfate turpentine.
  • the crude sulfate turpentine has a foul odor due to the sulfur-compounds present.
  • Mass spectrometerexamination of the volatile components in the condensate from the kraft pulp digester blow gas has confirmed the presence of hydrogen sulfide, methyl mercaptan, dimethyl sulfide, and dimethyl disulfide, and has shown that corresponding ethyl compounds and other sulfur-containing derivatives are not present in substantial concentrations.
  • the amount of loss of volatile organic sulfur compounds associatedwith the digester relief and blow as reported by Bergstrom and Trobeck is approximately two pounds of sulfur per ton of pulp produced. 'Pulping of Douglas fir produces one to five pounds of sulfur per ton of pulp produced of the same type of organic sulfur compounds, depending upon the pulping conditions. The most-critical factor in fixing the amount of this material produced is the cooking temperature. More sulfur compounds are produced at the higher temperatures. Due to the high vapor pressure of these compounds, they readily escapeinto the atmosphere during relief from the digester. Some of the materials are partially condensed with the steam and appear in the digester relief condensate (crude sulfate turpentine).
  • this invention has as an object the provision of an improved hydrogenation' process which will selectively convert the sulfur compounds in the crudev alpha-pinene to hydrogen sulfide while not appreciably alfecting'the unsaturated character of the alpha-pinene.
  • a further object of this invention is to provide a catalyst which will carry out the selective hydrogenation of the crude alpha-pinene without itselfbeingappreciably destroyed or inactivated.
  • the hydrogenation conditions include a temperature range of 300 F. to 500 F., pressures from 0 to 500 pounds per square inch, liquidjh'ourly space velocities of 1;25to 20 hour and hydrogen'rates of 1000 to 20,000 standard cubic feet per 42-gallon barrel of liquid feed.
  • the process is characterized by liquid yields in excess of percent and the effluent liquid will contain 20 percent or less of its original sulfur content.
  • the preferred catalyst consists of A" to pellets of alumina containing approximately 3% cobalt oxide and 15% molybdenum' oxide. 3 a
  • the activity of catalyst is enhanced by pre-sulfiding. This is accomplished by passing a gaseous mixture containing 80 volume percent hydrogen, 20 volume percent hydrogen sulfide over the catalyst at 400F. for about three hours.
  • the catalyst is rugged in this reaction. If it is used in the range of conditions designat'ed,it will operate for at least 600 volumes of oil per volume of catalyst with no deactivation.
  • Example 1 A feed comprising the alpha-pinene fraction from crude sulfate pulp liquor obtained from Springfield, Oregon, was passed over a catalyst comprising /8 pellets of Houdry Series C cobalt molybdate. ,This feed contained 510 p.p.m. of sulfur. Operating conditions comprised pressure, 25 p.s.i.g.; hydrogen rate, 5000 s.c.f./bbl.; temperature, 400 F.; liquid space velocity, 2.5 hour- The liquid yield was 95+% and the effluent liquid product contained 55 p.p.m. of sulfur.
  • Example 2 The crude alpha-pinene fraction from Springfield, Oregon, sulfate pulp mill liquor was passed over cobalt molybdate catalyst in the presence of hydrogen under the following conditions: pressure, 25 p.s.i.g.; temperature, 500 F.; hydrogen rate, 5000 s.c.f./bbl.; liquid space velocity, 10 hour- The sulfur content of the feed was 510 p.p.m.; the product contained 140 p.p.m. The yieldof liquid product exceeded 96%.
  • Example 3 The crude'alpha-pinene fraction from Springfield, Oregon, sulfate pulp mill liquor was passed over cobalt molybdate catalyst in the presence of hydrogen under the following conditions: pressure, 25 p.s.i.g.; temperature, 450 F.; hydrogen rate, 5000 s.c.f./bbl.; liquid space'velocity, hour ment, the sulfur content of the feed was reduced from 510 p.p.m. to 95 p.p.m. The yield of liquid was 97%.
  • Example 6 The following'ta-ble shows the'eifect of temperature on sulfur removal using the cobalt molybdate catalyst: Feedstock: Crude alpha-pinene from Springfield, Oregon sulfate pulp mill liquor. Sulfur Content of Feedstock: 510 p.p.m.
  • Feedstock Crude alpha-pinene from Springfield, Oregon sulfate pulp r. vSulfur Content of Feedstockf 510 p.p.m.
  • Reactor Temperature 40 Reactor Pressure: 25 p.s.i.g. Hydrogen Rate: 5000 s.c.f./bbl.
  • Example 5 The following table shows the effect of Hydrogen Rate: 5000 s.c.f./bbl.
  • liquid useful as a paint thinner, solvent, and raw mate rial for further syntheses.
  • a method for reducing the amount of sulfur compounds in the alpha-pinene fraction of sulfate pulp mill liquor which comprises passing said fraction over a cobalt molybdate catalyst at temperatures in the range of 300 F. to 500 F., pressures from 0 to 500 pounds per square inch gage, liquid hourly space velocities in the range of 1.25 to 20 hourand hydrogen rates in the range of 1000 to 20,000 standard cubic feet per 42-gallon barrel of liquor feed.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Analytical Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Water Supply & Treatment (AREA)
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Description

states ate't 3,3 12,75 Patented Apr. 4, 1967 ffice This invention relates to the hydrodesulfurizationof crude alpha-pinene, and more particularly, to a process for removing sulfur compounds from crude alpha-pinene by means of a catalytic hydrogenation.
The problem of controlling and reducing water and atmospheric pollution in the United States is becoming increasingly important. Eflluents from sulfate (or kraft) pulp mills are major contributors to the pollution problem. The release of foul odors has been a major defect of the kraft pulping process ever since its development in Germany more than 70 years ago. The odors are liberated at several points in the process which are usually widely separated in the mill, thus making the problem of containing and controlling. these odors difficult.
The furnace flue gases generally contain a relatively small concentration of the malodorous'substances; however, the total volume of discharge is so great that a considerable nuisance may result.
Condensates from the multiple-effect evaporator on the black liquor recovery system may contain a consider'able amount of the foul-smelling compounds, thus giving rise to a secondary nuisance.
The gases liberated in relieving and blowing the digesters are a major source for the foul odors associated with the kraft mill. The major offenders-are organic sulfur compounds, the principal malodorous substances being hydrogen sulfide, methyl mercaptan, dimethylsulfide, and dimethyl disulfide. Control of these gases is particularly difficult because their rate of release is 'subject to large fluctuations inherent from the batch digestion process.
If the gases evolved from the digester relief valve are condensed, the material obtained is called crude sulfate turpentine. The crude sulfate turpentine has a foul odor due to the sulfur-compounds present.
Mass spectrometerexamination of the volatile components in the condensate from the kraft pulp digester blow gas has confirmed the presence of hydrogen sulfide, methyl mercaptan, dimethyl sulfide, and dimethyl disulfide, and has shown that corresponding ethyl compounds and other sulfur-containing derivatives are not present in substantial concentrations. Thesame sulfur compounds-have been reported present in the-crude sulfate turpentine by Efishev, Prokhorov, and Matyushkina; also by Enkvist.
The amount of loss of volatile organic sulfur compounds associatedwith the digester relief and blow as reported by Bergstrom and Trobeck is approximately two pounds of sulfur per ton of pulp produced. 'Pulping of Douglas fir produces one to five pounds of sulfur per ton of pulp produced of the same type of organic sulfur compounds, depending upon the pulping conditions. The most-critical factor in fixing the amount of this material produced is the cooking temperature. More sulfur compounds are produced at the higher temperatures. Due to the high vapor pressure of these compounds, they readily escapeinto the atmosphere during relief from the digester. Some of the materials are partially condensed with the steam and appear in the digester relief condensate (crude sulfate turpentine).
Some sulfur analyses of samples of digester relief gases by Felicetta, Peniston, and McCarthy have shown the following distribution:
His omen cunts cunts,
Sample 1 131 5, 240 7, 350 4; 095 Sample 2 138 4, 880 7, 000 3, 870
Concentrations in parts per million by volume.
Most southern kraft mills obtain some reduction in the emission of odorous compounds from the digester gases through the recovery of the crude sulfate turpentine. The woods used by the southern mills yield up to four gallons of crude sulfate turpentine per ton of pulp produced and make the recovery of this material for refinement economically favorable. The yield of turpentine obtained from the northern and western mills is somewhat lower, approximately 1;5 gallons per tonof pulp produced, and recovery for refinement is seldom practiced. The type of trees processed, the operating conditions, and the efficiency of the recovery operation determine the yield of the turpentine obtained.
Current practices of recovery and disposal of crude sulfate turpentine from western pulp mills vary with different locations and with different mills. Burning as a partial fuel requirement is practiced in some mills. Others have dumped this material into the ocean where location permits. Repeated vaporization into the atmosphere has been tried, as Well as disposing intosettling ponds. In one case, no recovery system is used and all relief gases and turpentine emittedfforn the digest'ers'are dis-charged into the atmosphere.
Recovery of the crude sulfate turpentine is becoming of greater importance as a stable market for the material has developed, and also as pollution restrictions are tightened. An interest'in individual pure terpene1hydro carbons has also developed in the last few years and new sources of the basic terpenes are being sought. p
Once the crude sulfate turpentine has been recovered; the problem then becomes that of desulfurization'and purification to provide a product that will meet withpublic acceptance and also have the same desirable chemical and physical properties associated with pure gum spirits of turpentine. Many methods have been employed to accomplish these tasks with steam distillation and/or chemical treatment. Treating withhypo'chlorite or ethylene-diamine to further reduce the sulfur content appear to be the most common. Accordingly, this invention has as an object the provision of an improved hydrogenation' process which will selectively convert the sulfur compounds in the crudev alpha-pinene to hydrogen sulfide while not appreciably alfecting'the unsaturated character of the alpha-pinene.
A further object of this invention is to provide a catalyst which will carry out the selective hydrogenation of the crude alpha-pinene without itselfbeingappreciably destroyed or inactivated.
These objects are accomplished by the present invention wherein the crude alpha-pinene and gaseous hydrogen are passed over a cobalt-molybdate catalyst.
More specifically, the hydrogenation conditions include a temperature range of 300 F. to 500 F., pressures from 0 to 500 pounds per square inch, liquidjh'ourly space velocities of 1;25to 20 hour and hydrogen'rates of 1000 to 20,000 standard cubic feet per 42-gallon barrel of liquid feed.
The process is characterized by liquid yields in excess of percent and the effluent liquid will contain 20 percent or less of its original sulfur content. The preferred catalyst consists of A" to pellets of alumina containing approximately 3% cobalt oxide and 15% molybdenum' oxide. 3 a
The activity of catalyst is enhanced by pre-sulfiding. This is accomplished by passing a gaseous mixture containing 80 volume percent hydrogen, 20 volume percent hydrogen sulfide over the catalyst at 400F. for about three hours.
The catalyst is rugged in this reaction. If it is used in the range of conditions designat'ed,it will operate for at least 600 volumes of oil per volume of catalyst with no deactivation.
The following examples illustrate the remarkable results obtained in accordance with our invention on crude alpha-pinene obtained from widely scattered sources: 1 Example 1.-A feed comprising the alpha-pinene fraction from crude sulfate pulp liquor obtained from Springfield, Oregon, was passed over a catalyst comprising /8 pellets of Houdry Series C cobalt molybdate. ,This feed contained 510 p.p.m. of sulfur. Operating conditions comprised pressure, 25 p.s.i.g.; hydrogen rate, 5000 s.c.f./bbl.; temperature, 400 F.; liquid space velocity, 2.5 hour- The liquid yield was 95+% and the effluent liquid product contained 55 p.p.m. of sulfur.
Under identical operating conditions and the same catalyst, crude alpha-pinches from the following sources and sulfur content were treated and yielded the following final sulfur content.
, Example 2.-The crude alpha-pinene fraction from Springfield, Oregon, sulfate pulp mill liquor was passed over cobalt molybdate catalyst in the presence of hydrogen under the following conditions: pressure, 25 p.s.i.g.; temperature, 500 F.; hydrogen rate, 5000 s.c.f./bbl.; liquid space velocity, 10 hour- The sulfur content of the feed was 510 p.p.m.; the product contained 140 p.p.m. The yieldof liquid product exceeded 96%. Example 3.-The crude'alpha-pinene fraction from Springfield, Oregon, sulfate pulp mill liquor was passed over cobalt molybdate catalyst in the presence of hydrogen under the following conditions: pressure, 25 p.s.i.g.; temperature, 450 F.; hydrogen rate, 5000 s.c.f./bbl.; liquid space'velocity, hour ment, the sulfur content of the feed was reduced from 510 p.p.m. to 95 p.p.m. The yield of liquid was 97%. Example 4.-The following table shows the effect of space velocity on sulfur removal using the cobalt molybdate catalyst:
As a result of this treat-' reactor pressure on sulfur removal using the cobalt moly-bdate catalyst: V
Sulfur Content of Product, p.p.m. Average Reactor Pressure Conversion Trial 1 Trial 2 Average 70 75 72. 5 v 85.8 105 95 100.0 80.5 125 105 115.0 77. 5 145 135 140. 0 72. 6 500 42% pinane These data indicate'that increased pressure reduces somewhat the amount of desulfurization. The 500 p.s.i.g. run gave a 42% of pinane indicating that at this pressure, hydrogen adds, across the double bond in the alphapinene to drastically reduce the yield of the alpha-pinene. Example 6.The following'ta-ble shows the'eifect of temperature on sulfur removal using the cobalt molybdate catalyst: Feedstock: Crude alpha-pinene from Springfield, Oregon sulfate pulp mill liquor. Sulfur Content of Feedstock: 510 p.p.m.
' Reactor Pressure: 25 p.s.i.g
Feedstock: Crude alpha-pinene from Springfield, Oregon sulfate pulp r. vSulfur Content of Feedstockf 510 p.p.m.
Reactor Temperature: 40 Reactor Pressure: 25 p.s.i.g. Hydrogen Rate: 5000 s.c.f./bbl.
These data show that when other conditions are held constant, the lower the space velocity, the greater is the desulfurization.
Example 5.-The following table shows the effect of Hydrogen Rate: 5000 s.c.f./bbl.
, Sulfur Content of Average Space Product, p.p.m. Conver- Reactor Temp., F. Velocity sion,
hr.- Percent Trial 1' Trial 2 These data show the greatest desulfurization is obtained is about 400 F. and a liquid space velocity of 2.5 hrr Example 7.-The following table shows the effect of hydrogen rate'on sulfur removal using the cobalt molybdate catalyst:
mill liquor. Sulfur Content of Feedstock: 510 p.p.m. Reactor Temperature: 40 F. Reactor Pressure: 250 p.s.i.g. Liquid Space Velocity: 5 hour- Feedstock: Crude alpharpinene from Springfield, Oregon sulfate pulp Hydrogen Rate, Sulfur Content of Percent Conversion s.c.f./bbl. Product, p.p.m.
These data show that approximately 5000 s.c.f./bbl. of
hydrogen are required to obtain good desulfurization and that rates higher than this give little benefit.
The examples presented above show the effect of the variables temperature, pressure, space velocity, and hydrogen rate on the desulfurization of crude alpha-pinene. We have shown that by proper control of these variables, 60 to 90 percent sulfur removal can be accomplished with the cobalt molybdate catalyst.
Our invention has great economic advantages. The crude alpha-pinene containing 150 p.p.m. or more of sulfur is a malodorous liquid having little economic use other than a cheap fuel. After treatment by our process,
liquid, useful as a paint thinner, solvent, and raw mate rial for further syntheses.
1. A method for reducing the amount of sulfur compounds in the alpha-pinene fraction of sulfate pulp mill liquor which comprises passing said fraction over a cobalt molybdate catalyst at temperatures in the range of 300 F. to 500 F., pressures from 0 to 500 pounds per square inch gage, liquid hourly space velocities in the range of 1.25 to 20 hourand hydrogen rates in the range of 1000 to 20,000 standard cubic feet per 42-gallon barrel of liquor feed.
2. A method as defined in claim 1 in which the temperature is maintained at about 400 F. and the pressure at about 25 p.s.i.g.
References Cited by the Examiner UNITED STATES PATENTS DELBERT E. GANTZ, Primary Examiner. C. R. DAVIS. Assistant Examiner.

Claims (1)

1. A METHOD FOR REDUCING THE AMOUNT OF SULFUR COMPOUNDS IN THE ALPHA-PINENE FRACTION OF SULFATE PULP MILL LIQUOR WHICH COMPRISES PASSING SAID FRACTION OVER A COBALT MOLYBDATE CATALYST AT TEMPERATURE IN THE RANGE OF 300*F. TO 500*F., PRESSURES FROM 0 TO 500 POUNDS PER SQUARE INCH GAGE, LIQUID HOURLY SPACE VELOCITIES IN THE RANGE OF 1.25 TO 20 HOUR-1, AND HYDROGEN RATES IN THE RANGE OF 1000 TO 20,000 STANDARD CUBIC FEET PER 42-GALLON BARREL OF LIQUOR FEED.
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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3359342A (en) * 1967-01-16 1967-12-19 Glidden Co Pretreating and isomerizing alpha-pinene
US3360581A (en) * 1967-01-16 1967-12-26 Glidden Co Pretreating and isomerizing alpha-pinene
FR2597495A1 (en) * 1986-04-18 1987-10-23 Elf Aquitaine PROCESS AND CATALYST FOR DESULFURIZING TERPENIC ESSENCES
FR2605900A1 (en) * 1986-10-29 1988-05-06 Elf Aquitaine IMPROVEMENT TO THE PROCESS OF DESULFURING TERPENIC ESSENCES
WO2011004065A3 (en) * 2009-07-07 2011-02-24 Upm-Kymmene Corporation Process for producing hydrocarbons by hydrodesulphurizing a crude turpentine feed
WO2013029663A1 (en) * 2011-08-30 2013-03-07 Upm-Kymmene Corporation Method for hydroisomerising renewable hydrocarbons
US20130072730A1 (en) * 2010-05-25 2013-03-21 Upm-Kymmene Corporation Process and apparatus for producing hydrocarbons from feed-stocks comprising tall oil and terpene-compounds

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2976336A (en) * 1956-07-11 1961-03-21 British Petroleum Co Purification of benzene
US3125509A (en) * 1959-10-26 1964-03-17 Process for the treatment of petroleum
US3152091A (en) * 1959-02-24 1964-10-06 Sinclair Research Inc Process for preparing alumina-based catalysts
US3183180A (en) * 1964-02-18 1965-05-11 Hydrocarbon Research Inc Hydrogenation of oils

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2976336A (en) * 1956-07-11 1961-03-21 British Petroleum Co Purification of benzene
US3152091A (en) * 1959-02-24 1964-10-06 Sinclair Research Inc Process for preparing alumina-based catalysts
US3125509A (en) * 1959-10-26 1964-03-17 Process for the treatment of petroleum
US3183180A (en) * 1964-02-18 1965-05-11 Hydrocarbon Research Inc Hydrogenation of oils

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3359342A (en) * 1967-01-16 1967-12-19 Glidden Co Pretreating and isomerizing alpha-pinene
US3360581A (en) * 1967-01-16 1967-12-26 Glidden Co Pretreating and isomerizing alpha-pinene
FR2597495A1 (en) * 1986-04-18 1987-10-23 Elf Aquitaine PROCESS AND CATALYST FOR DESULFURIZING TERPENIC ESSENCES
EP0243238A1 (en) * 1986-04-18 1987-10-28 Societe Nationale Elf Aquitaine (Production) Process and catalyst for the desulfurization of terpenic oils
FR2605900A1 (en) * 1986-10-29 1988-05-06 Elf Aquitaine IMPROVEMENT TO THE PROCESS OF DESULFURING TERPENIC ESSENCES
EP0267833A1 (en) * 1986-10-29 1988-05-18 Societe Nationale Elf Aquitaine (Production) Process for the desulfurization of ternic oils
WO2011004065A3 (en) * 2009-07-07 2011-02-24 Upm-Kymmene Corporation Process for producing hydrocarbons by hydrodesulphurizing a crude turpentine feed
US20120108675A1 (en) * 2009-07-07 2012-05-03 Upm-Kymmene Corporation Process and apparatus for producing hydrocarbons by hydrogenating a terpene feed
US9677011B2 (en) * 2009-07-07 2017-06-13 Upm-Kymmene Corporation Process and apparatus for producing hydrocarbons by hydrogenating a terpene feed
EP2454343B1 (en) * 2009-07-07 2018-09-05 UPM-Kymmene Corporation Process for producing hydrocarbons by hydrogenating a terpene feed
US20130072730A1 (en) * 2010-05-25 2013-03-21 Upm-Kymmene Corporation Process and apparatus for producing hydrocarbons from feed-stocks comprising tall oil and terpene-compounds
US9382483B2 (en) * 2010-05-25 2016-07-05 Upm-Kymmene Corporation Process and apparatus for producing hydrocarbons from feed-stocks comprising tall oil and terpene-compounds
WO2013029663A1 (en) * 2011-08-30 2013-03-07 Upm-Kymmene Corporation Method for hydroisomerising renewable hydrocarbons

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