US3210434A - Production of phenylnapthalene - Google Patents
Production of phenylnapthalene Download PDFInfo
- Publication number
- US3210434A US3210434A US244780A US24478062A US3210434A US 3210434 A US3210434 A US 3210434A US 244780 A US244780 A US 244780A US 24478062 A US24478062 A US 24478062A US 3210434 A US3210434 A US 3210434A
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- Prior art keywords
- benzene
- mixture
- naphthalene
- phenylnaphthalene
- bed
- Prior art date
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- IYDMICQAKLQHLA-UHFFFAOYSA-N 1-phenylnaphthalene Chemical compound C1=CC=CC=C1C1=CC=CC2=CC=CC=C12 IYDMICQAKLQHLA-UHFFFAOYSA-N 0.000 title claims description 24
- 238000004519 manufacturing process Methods 0.000 title description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 114
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 68
- 239000000203 mixture Substances 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 18
- TURIHPLQSRVWHU-UHFFFAOYSA-N 2-phenylnaphthalene Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=C1 TURIHPLQSRVWHU-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 6
- 235000010290 biphenyl Nutrition 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 239000010453 quartz Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 239000000571 coke Substances 0.000 description 2
- 238000004939 coking Methods 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/76—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation of hydrocarbons with partial elimination of hydrogen
-
- 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
- Y10S585/8995—Catalyst and recycle considerations
- Y10S585/905—Catalyst and recycle considerations by-product conversion to feed
Definitions
- Phenylnaphthalene has the empirical formula It exists in two isomeric forms, which are conventionally designated as 1-phenylnaphthalene and 2-phenylnaph l-phenylnaphthalene has a melting point of 113 F, and boils at 617 F. Z-PhenyInaphthalene melts at 216.5 F. and boils at 657 F. The phenylnaphthalenes can be used as heat exchange media and chemical intermediates, as Well as for other purposes.
- a primary objective of this invention has been to provide ⁇ an economical process for producing phenylnaphthalene in substantial yields, from commercially available starting materials.
- the mol ratio of benzene to naphthalene in the input stream is important for obtaining the best yield. This ratio should preferably be above 2:3; with larger proportions of naphthalene, coking is severe. The best conversion results are obtained when the benzene/naphthalene ratio is about 3 :2.
- Residence time as measured by superficial velocity in the reaction zone, also beats an important relation to yield and to the degree to which high boiling residues and coke are formed. I -believe that the residencetime should preferably -be in the range of about 0.5 to 2 seconds; about 1.4 seconds is optimal at 1600 F. In general, coking and formation of high boiling compounds tend to increase with longer residue times.
- a feed comprising approximately 59 mol percent benzene and 41 mol percent naphthalene, both technical grade, was passed down flow through a bed of an inert material such as quartz chips or ceramic beads.
- the bed was externally heated, and peak temperature was 1594 F. Residence time in the bed at temperatures over 1500 F. was 1.42 seconds.
- the process was conducted in the absence of added hydrogen and at ⁇ atmospheric pressure.
- the liquid product yield was 94.3% of the feed, and the liquid product comprised 3.7% l-phenylnaphthalene, 7.1% 2-phenylnaphthalene, 20.2% benzene, and 55.4% naphthalene.
- biphenyl 7.1% biphenyl was formed as a side product, together ⁇ with 6.5% of coke ⁇ and compounds having boiling points higher than 2-phenylnaphthalene- The increased proportion of naphthalene was apparently due to synthesis from benzene. If ⁇ biphenyl is converted to benzene, which can be done by known technology, and the converted benzene is recycled together with unreacted benzene and naphthalene from the primary reaction, ultimate theoretical yields of 20.2% l-phenylnaphthalene and 38.7% 2-phenylnaphthalene could be expected.
- the reaction is a thermal reaction, and does not require a catalyst.
- Reactor design is not believed to be critical; while a downflow bed of quartz chips or beads is preferred, the reactor might also comprise any contiguration in which the reactants are passed through or over an inert material heated directly or indirectly.
- the resultant mixture which typically will comprise benzene, naphthalene, biphenyl produced as a side reaction product, and 1- and Z-phenylnaphthalenes, together with higher boiling compounds, is passed through a conventional fractionation or separation zone.
- the separation of the desired phenylnaphthalenes from this mixture may be accomplished, by way of example, by fractionating a cut comprising a relatively pure mixture of 1- and 2-phenylnaphthalenes. This cut is then separated into its phenylnaphthalene components by fractional crystallization.
- the very low conversions at temperatures of about 1400 F. indicate that the operating temperature should preferably be above that temperature.
- the mol ratio of benzene to naphthalene should be higher than about 2:3, because of the poor conversion at that ratio, as exemplified by Run EPN-13, in which there was a large conversion to high boiling materials that ultimately resulted in plugging the reactor.
- said mixture comprising at least 2 mol parts benzene and 3 parts naphthalene
- the mixture being maintained in contact with the bed for a residence time of between about 0.5 and 2 seconds,
- said mixture comprising at least 2 mol parts benzene to 3 parts naphthalene
- the mixture being maintained in contact with the bed for a residence time of between about 0.5 and 2 seconds,
- said mixture comprising about 3 mol parts benzene to about 2 parts naphthalene,
- said mixture comprising about 3 mol parts benzene to about 2 parts naphthalene,
- the benzene/naphthalene mol ratio of said mixture being about 3/ 2, the mixture being maintained in contact with the bed for a residence time of about 1.0-1.8 seconds, and separating 1- and 2-phenylnaphthalene from the mixture so treated.
- said mixture comprising at least 2 m01 parts benzene to 3 parts naphthalene,
- the mixture being maintained at said temperature for a period of between about 0.5 and 2 seconds,
- the method of producing phenylnaphthalene comprising, passing a mixture of benzene and naphthalene in contact with an inert bed at a temperature in the range of substantially 14001600 F., said mixture comprising at least 2 mol parts benzene to 3 m01 parts naphthalene, the mixture being maintained in contact with the bed for a residence time of between about 0.5 and 2 seconds, separating phenylnaphthalene, by-product diphenyl, and unreacted benzene and naphtbalene from the eflluent, converting the diphenyl to benzene and recycling benzene from the next previous step together with the separated unreacted benzene and naphthalene to the reaction zone.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Oct. 5, 1965 D. K. CHAPMAN PRODUCTION OF PHENYLNAPTHALENE Filed Deo. 14, 1962 m30. mmm m1 INVENTOR 17mm/[Ks BY M United States Patent O 3,210,434 PRODUCTION F PHENYLNAPTHALENE Duane K. Chapman, Ashland, Ky., assignor to Ashland Oil & Refining Company, Ashland, Ky., a corporation of Kentucky Filed Dec. 14, 1962, Ser. No. 244,780 9 Claims. (Cl. 2611-670) This invention relates to the production of phenylnaphthalene directly from benzene and naphthalene.
Phenylnaphthalene has the empirical formula It exists in two isomeric forms, which are conventionally designated as 1-phenylnaphthalene and 2-phenylnaph l-phenylnaphthalene has a melting point of 113 F, and boils at 617 F. Z-PhenyInaphthalene melts at 216.5 F. and boils at 657 F. The phenylnaphthalenes can be used as heat exchange media and chemical intermediates, as Well as for other purposes.
A primary objective of this invention has been to provide `an economical process for producing phenylnaphthalene in substantial yields, from commercially available starting materials.
I have empirically discovered a process whereby both 1- `and 2,-phenylnaphthalene may readily be synthesized from benzene and naphthalene. In accordance with this process, a mixture of naphthalene and benzene, in a certain range of mol ratios, is contacted with an inert bed, for example, packed with quartz or ceramic chips, at a temperature in excess of substantially 1400 and preferably at about 1600 F.
At these Aconditions the benzene and naphthalene apparently undergo thermal pyrolysis. The over-all reaction may be illustrated:
3,210,434 Patented Oct. 5, 1965 lCC As will be shown, the relative yields of lphenylnaph thalene and 2-phenylnaphthalene are in the ratio of approximately 1:2, as theory would suggest.
The mol ratio of benzene to naphthalene in the input stream is important for obtaining the best yield. This ratio should preferably be above 2:3; with larger proportions of naphthalene, coking is severe. The best conversion results are obtained when the benzene/naphthalene ratio is about 3 :2.
Residence time, as measured by superficial velocity in the reaction zone, also beats an important relation to yield and to the degree to which high boiling residues and coke are formed. I -believe that the residencetime should preferably -be in the range of about 0.5 to 2 seconds; about 1.4 seconds is optimal at 1600 F. In general, coking and formation of high boiling compounds tend to increase with longer residue times.
An important feature of the process I have discovered is that it may be carried out at atmospheric pressures, thereby making possible the use of inexpensive equipment. Moreover, the reaction will proceed in the absence of added hydrogen, thus eliminating the need for a separate source of hydrogen.
The accompanying drawing is a flow sheet illustrating the preferred practice of this process.
In accordance with a preferred example of the process I have discovered, a feed comprising approximately 59 mol percent benzene and 41 mol percent naphthalene, both technical grade, was passed down flow through a bed of an inert material such as quartz chips or ceramic beads. The bed was externally heated, and peak temperature was 1594 F. Residence time in the bed at temperatures over 1500 F. was 1.42 seconds. The process was conducted in the absence of added hydrogen and at `atmospheric pressure. The liquid product yield was 94.3% of the feed, and the liquid product comprised 3.7% l-phenylnaphthalene, 7.1% 2-phenylnaphthalene, 20.2% benzene, and 55.4% naphthalene. 7.1% biphenyl was formed as a side product, together `with 6.5% of coke `and compounds having boiling points higher than 2-phenylnaphthalene- The increased proportion of naphthalene was apparently due to synthesis from benzene. If` biphenyl is converted to benzene, which can be done by known technology, and the converted benzene is recycled together with unreacted benzene and naphthalene from the primary reaction, ultimate theoretical yields of 20.2% l-phenylnaphthalene and 38.7% 2-phenylnaphthalene could be expected.
The following table illustrates practice of this process over a range of residence times, temperatures, and feed ratios.
4 2. The method of producing phenylnaphthalene comprising,
passing a mixture of benzene and naphthalene in con- TABLE Operatzng condztzons and product analysls Run Number BPN-6B EPN-6G EPN-6D EPN-7 BPN-S EPN-11 EPN-13 EPN-14 Residence Time, over 1,500u F., Sec.. 1.02 1. 1. 42 1. 63 1. 83 1. 23 1. 44 0. 0 6211; Temperature, F 1, 590 1, 591 1, 594 1, 590 1, 590 1, 569 1, 555 1, 404
Benzene, Mol percent 59 59 59 53 64 81 40 61 Naphthalene Mol pereent 41 41 41 47 36 19 60 39 Product Yield, Wt. percent 87. 7 93. 0 94. 3 85.0 90. 1 92.0 85. 4 91.0 Product Analysis, Wt percent:
Benzene 22. 9 31. 8 20. 2 33. 1 43. 8 58. 6 20. 9 40. 6 58.8 48. 7 55. 4 48. 7 41. 8 23. 2 58. 2 56. 3 y 5.1 4.9 7.1 3.4 5.6 10.5 5.4 1.8 1-Phenylnaphthalene 3. 2 3. 3 3. 7 2. 8 2. 3 1. 8 2. 3 0. 5 2-Phenylnaphthalene 5. 6 6. 4 7. 1 5. 9 4. 6 3. 6 4. 5 0. 8 t 2Phenylnaphthalene 4.4 4.9 6.5 6.1 1.9 2.3 8.7 0.0 Yleld of 1- and ZPhenylnaphthalene and Higher Boiling compounds' v l-Phenylnaphthalene-- 21. 3 21. 1 20. 2 16. 1 23. 6 21. 5 12. 7 35.0 2Phenylnaphthalene 37. 2 40.8 38.7 33. 9 47. 1 43. 1 24. 8 56. 0 2Phenylnaphthalene 29. 3 31. 2 35. 4 35. 1 19. 5 27. 5 47. 9 0. 0
From the table it will be apparent that the yields of 1- and 2phenylnaphthalene are poorest at an operating temperature of about 1400 F. (Run EPN-14), and that in general much better yields are obtained at temperatures of about 1600 F. As illustrated by Run EPN-6D, which corresponds to the specific example previously given, the best conversions at 1600 F. are obtained at residence times of about 1.4 seconds and at a feed ratio of approximately 3 mol parts benzene to 2 mol parts naphthalene. At times these operating conditions, residence times in excess of about 1.4 seconds tend to cause progressively poorer yields of 1- and Z-phenylnaphthalene, although the yields are nonetheless better than the yield obtained at about 1400 F.
The reaction is a thermal reaction, and does not require a catalyst. Reactor design is not believed to be critical; while a downflow bed of quartz chips or beads is preferred, the reactor might also comprise any contiguration in which the reactants are passed through or over an inert material heated directly or indirectly.
Following passage through the reactor, the resultant mixture, which typically will comprise benzene, naphthalene, biphenyl produced as a side reaction product, and 1- and Z-phenylnaphthalenes, together with higher boiling compounds, is passed through a conventional fractionation or separation zone. The separation of the desired phenylnaphthalenes from this mixture may be accomplished, by way of example, by fractionating a cut comprising a relatively pure mixture of 1- and 2-phenylnaphthalenes. This cut is then separated into its phenylnaphthalene components by fractional crystallization.
The very low conversions at temperatures of about 1400 F. indicate that the operating temperature should preferably be above that temperature. The mol ratio of benzene to naphthalene should be higher than about 2:3, because of the poor conversion at that ratio, as exemplified by Run EPN-13, in which there was a large conversion to high boiling materials that ultimately resulted in plugging the reactor.
Having described my invention, what is claimed is:
1. The method of producing phenylnaphthalene comprising,
passing a mixture of benzene and naphthalene in contact with an inert bed at a temperature in the range of substantially 14001600 F.,
said mixture comprising at least 2 mol parts benzene and 3 parts naphthalene,
the mixture being maintained in contact with the bed for a residence time of between about 0.5 and 2 seconds,
and separating phenylnaphthalene from the mixture so treated.
tact with an inert bed at a temperature of at least 1400 F.,
said mixture comprising at least 2 mol parts benzene to 3 parts naphthalene,
the mixture being maintained in contact with the bed for a residence time of between about 0.5 and 2 seconds,
and separating phenylnaphthalene from the mixture so treated.
3. The method of claim 2 wherein the benzene/naphthalene mol ratio of said mixture is in the range of about 2/ 3 to 4/ 1.
4. The method of producing phenylnaphthalene comprising,
passing a mixture of benzene and naphthalene in contact with an inert bed at a temperature of about 1600 F.,
said mixture comprising about 3 mol parts benzene to about 2 parts naphthalene,
the mixture being maintained in contact with the bed for a residence time of between about 1.0 and 1.8 seconds,
and separating 1- and Z-phenylnaphthalene from the mixture so treated.
5. The method of producing phenylnaphthalene comprising,
passing a mixture of benzene and naphthalene in contact with an inert bed of quartz bodies at a temperature of about 1600a F.,
said mixture comprising about 3 mol parts benzene to about 2 parts naphthalene,
the mixture being maintained in contact with the bed for a residence time of between about 1.0 and 1.8 seconds,
and separating 1- and Z-phenylnaphthalene from the mixture so treated.
6. The method of producing 1- and 2-phenylnaphthalene comprising,
passing a mixture of benzene and naphthalene in contact with a quartz bed at a temperature of about 15001600 F. and at substantially atmospheric pressure,
the benzene/naphthalene mol ratio of said mixture being about 3/ 2, the mixture being maintained in contact with the bed for a residence time of about 1.0-1.8 seconds, and separating 1- and 2-phenylnaphthalene from the mixture so treated.
7. The method of claim 6 wherein said residence time` is about 1.4 seconds and wherein said temperature is about 1600 F.
8. The method comprising,
subjecting a mixture of benzene and naphthalene to pyrolysis at a temperature of at least 1400" F.,
said mixture comprising at least 2 m01 parts benzene to 3 parts naphthalene,
the mixture being maintained at said temperature for a period of between about 0.5 and 2 seconds,
and separating phenylnaphthalene from the mixture so treated.
9. The method of producing phenylnaphthalene comprising, passing a mixture of benzene and naphthalene in contact with an inert bed at a temperature in the range of substantially 14001600 F., said mixture comprising at least 2 mol parts benzene to 3 m01 parts naphthalene, the mixture being maintained in contact with the bed for a residence time of between about 0.5 and 2 seconds, separating phenylnaphthalene, by-product diphenyl, and unreacted benzene and naphtbalene from the eflluent, converting the diphenyl to benzene and recycling benzene from the next previous step together with the separated unreacted benzene and naphthalene to the reaction zone.
References Cited by the Examiner UNITED STATES PATENTS 1,996,738 4/35 Drossbach et al. 260-670 ALPHONSO D. SULLIVAN, Primary Examiner.
JOSEPH R. LIBERMAN, Examiner.
UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No 3, 210,434 October 5 1965 Duane K. Chapman It is hereby certified that error appears in the above numbered patent requiring correction and that the said Letters Patent should read as corrected below.
Column Z, line 20, for "beats" read bears line 26, for "residue" read residence n; Column 3, line 33, strike out "tmes"; line 70, for "and" read to Signed and sealed this 3rd day of May 1966.
SEAL) `ttest:
RNEST w. SWTDEE EDWARD J. BRENNERV ttesting Ufficer Commissioner of Patents
Claims (1)
1. THE METHOD OF PRODUCING PHENYLNAPHTHALENE COMPRISING, PASSING A MIXTURE OF BENZENE AND NAPHTHALENE IN CONTACT WITH AN INERT BED AT A TEMPERATURE IN THE RANGE OF SUBSTANTIALLY 1400*-1600*F., SAID MIXTURE COMPRISING AT LEAST 2 MOL PARTS BENZENE AND 3 PARTS NAPHTHALENE, THE MIXTURE BEING MAINTAINED IN CONTACT WITH THE BED FOR A RESIDENCE TIME OF BETWEEN ABOUT 0.5 AND 2 SECONDS, AND SEPARATING PHENYLNAPHTHALENE FROM THE MIXTURE SO TREATED.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US244780A US3210434A (en) | 1962-12-14 | 1962-12-14 | Production of phenylnapthalene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US244780A US3210434A (en) | 1962-12-14 | 1962-12-14 | Production of phenylnapthalene |
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| Publication Number | Publication Date |
|---|---|
| US3210434A true US3210434A (en) | 1965-10-05 |
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| Application Number | Title | Priority Date | Filing Date |
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| US244780A Expired - Lifetime US3210434A (en) | 1962-12-14 | 1962-12-14 | Production of phenylnapthalene |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3517076A (en) * | 1966-02-14 | 1970-06-23 | Monsanto Co | Thermal hydrodealkylation of alkyl aromatic hydrocarbons |
| US3548019A (en) * | 1968-04-22 | 1970-12-15 | Sun Oil Co | Process for the production of naphthalene |
| US20040043969A1 (en) * | 2000-03-10 | 2004-03-04 | Pinney Kevin G. | Tubulin binding agents and corresponding prodrug constructs |
| EP4036189A1 (en) | 2021-02-02 | 2022-08-03 | Indian Oil Corporation Limited | Process for synthesis of polyhydrocarbons as heat transfer agents |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1996738A (en) * | 1929-12-16 | 1935-04-09 | Ig Farbenindustrie Ag | Production of condensation products from aromatic hydrocarbons |
-
1962
- 1962-12-14 US US244780A patent/US3210434A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1996738A (en) * | 1929-12-16 | 1935-04-09 | Ig Farbenindustrie Ag | Production of condensation products from aromatic hydrocarbons |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3517076A (en) * | 1966-02-14 | 1970-06-23 | Monsanto Co | Thermal hydrodealkylation of alkyl aromatic hydrocarbons |
| US3548019A (en) * | 1968-04-22 | 1970-12-15 | Sun Oil Co | Process for the production of naphthalene |
| US20040043969A1 (en) * | 2000-03-10 | 2004-03-04 | Pinney Kevin G. | Tubulin binding agents and corresponding prodrug constructs |
| US7001926B2 (en) * | 2000-03-10 | 2006-02-21 | Oxigene, Inc. | Tubulin binding agents and corresponding prodrug constructs |
| WO2004087061A3 (en) * | 2003-04-01 | 2005-03-17 | Oxigene Inc | Tubulin binding agents and corresponding prodrug constructs |
| EP4036189A1 (en) | 2021-02-02 | 2022-08-03 | Indian Oil Corporation Limited | Process for synthesis of polyhydrocarbons as heat transfer agents |
| US11548838B2 (en) | 2021-02-02 | 2023-01-10 | Indian Oil Corporation Limited | Process for synthesis of polyhydrocarbons as heat transfer agents |
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