US2500161A - Conversion of 1-olefins in the presence of lead tetraacetate - Google Patents
Conversion of 1-olefins in the presence of lead tetraacetate Download PDFInfo
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- US2500161A US2500161A US44403A US4440348A US2500161A US 2500161 A US2500161 A US 2500161A US 44403 A US44403 A US 44403A US 4440348 A US4440348 A US 4440348A US 2500161 A US2500161 A US 2500161A
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- olefin
- normal
- olefins
- lead
- conversion
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- JEHCHYAKAXDFKV-UHFFFAOYSA-J lead tetraacetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O JEHCHYAKAXDFKV-UHFFFAOYSA-J 0.000 title claims 2
- 238000006243 chemical reaction Methods 0.000 title description 13
- 150000001336 alkenes Chemical class 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 18
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 17
- 150000005673 monoalkenes Chemical class 0.000 claims description 11
- 238000010438 heat treatment Methods 0.000 claims description 9
- 239000007791 liquid phase Substances 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 239000003921 oil Substances 0.000 description 21
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 17
- 239000000314 lubricant Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000005484 gravity Effects 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- -1 aromatic sulfonic Chemical class 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- DAEVZSVHMGSIEQ-UHFFFAOYSA-N C1=CC=CC=C1.[Ba] Chemical compound C1=CC=CC=C1.[Ba] DAEVZSVHMGSIEQ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000004129 EU approved improving agent Substances 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 208000009989 Posterior Leukoencephalopathy Syndrome Diseases 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Natural products OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000007965 phenolic acids Chemical class 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000010689 synthetic lubricating oil Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/14—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of germanium, tin or lead
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
Definitions
- This invention has to do with hydrocarbon conversion and with synthetic lubricants or viscous oils prepared by such a conversion. More specifically. the invention is concerned with a new process for converting certain mono-oleilnic hydrocarbons to lubricants of outstanding quality.
- the mono-olefins of this invention are normal or straight chain alpha monoolefins and contain from about 6 to about 12 carbon atoms. Such mono-olefins are normally liquid at temperatures of the order of 20-25 C. Illustrative of such mono-olefins are the following: hexene-l, octene-l, decene-l, dodecene-l, and the like. Of such olefins, decene-l is preferred in view of the particularly outstanding characteristics of the lubricants formed therefrom. It will be clear from the foregoing examples that an alpha olefin may also be referred to as a l-olefin.
- mono-oleflns may be used individually, but they may also be used in admixture with each other.
- olefin mixtures containing a substantial proportion of such mono-olefins may be used. 'Preferred of such mixtures are those'containing a major proportion of a normal l-olefln or of normal l-olefins.
- hydrocarbon mixtures are those obtained by the cracking of paraflin waxes and other paraflin products, and those obtained from the Fischer-Tropsch and related processes.
- These hydrocarbon mixtures may contain, in addition to the normal l-olefin' or normal l-olefins, such materials as: other oleflns, parailins, naphthenes and aromatics.
- Lead tetra-acetate used herein to convert the foregoing normal i-olefins to synthetic lubricants is well known, as are. methods by which it may be prepared.
- One typical method of preparation involves reaction of lead dioxide (PbOz) and acetic anhydride.
- lead tetra-acetate may be formed in situ, as from lead dioxide and acetic anhydride. 7
- the pressure to be employed depends upon the temperature used, and ordinarily a pressure suflicient to maintain the olefin in substantially the liquid phase is adequate. With temperatures within the 500-700" F. range, pressures of the order of 300-600 pounds per square inch are generally developed in the reaction vessel used. Reaction times will vary depending upon the particular olefin involved, quantity of olefin, temperature and, to a certain extent, pressure. In general, the higher the temperature employed, the shorter the reaction time required, the criterion used being the time required at a given reaction temperature to eflect substantial conversion of the normal l-olefin to a viscous oil. Generally, reaction times within the range of 1 to 10 hours are satisfactory.
- the process .contemplated herein is rather sim-' ply accomplished by mixing the normal l-olefin. and lead tetra-acetate in a shaker bomb type of reactor, replacing the air therein by an inert atmosphere of nitrogen or the like, and applying the desired temperature and pressure for a suflicient length of time to complete the conversion. It will be apparent to those skilled in the art that the process may be carried out in a batch procedure such as indicated, or may be carried out in a continuous or semi-continuous operation of the type ,widely used in the petroleum industry.
- Example I A typical conversion was accomplished as follows: A. shaker bomb was charged with 280 grams (2.0 mols) of decene-l and 44 grams (0.1 mol) of lead tetraacetate. The air therein was replaced with nitrogen and the bomb heated toapproxi- 3 mately 500 F. (260 C.) for five hours. A pressure of 650 pounds per square inch developed in the bomb during the run.
- the liquid contents of the bomb were filtered free of the relatively large amount of lead salt which was found to be present.
- a small amount of unreacted decene-l was distilled out at atmospheric pressure.
- a vacuum distillate cut was collected up to approximately 200 C. at 2 millimeters pressure.
- the residual oil weighed 60 grams and had the following characteristics:
- Example II Decene-l was in contact with lead peroxide or dioxide (PbOa) and acetic anhydride, which most probably formed lead tetra-acetate in situ.
- the quantities used were: 280 grams (2.0 mols) of decene-l; 24 grams (0.1 mol) of PhD: and 41 grams (0.4 mol) of acetic anhydride.
- the synthetic oils impart desirable viscosity index (V. I.) and pour point characteristics to the oils in combination therewith, for, as indicated above, they have advantageous viscosity index and pour point properties.
- V. I. desirable viscosity index
- pour point characteristics to the oils in combination therewith, for, as indicated above, they have advantageous viscosity index and pour point properties.
- the synthetic oils find utility in upgrading" other lubricants.
- Typical oils with which the synthetic oils may be blended are mineral oils such as are normally used in internal combustion and turbine engines. When so blended, the synthetic oils may comprise the major proportion of the final blended oil, or may even comprise a minor proportion thereof.
- One or more of the individual properties of the synthetic lubricants of this invention may be further improved by incorporating therewith a small, but effective amount, of an addition agent such as a detergent, an extreme pressure agent, a foam suppressor, a viscosity index (V. I.) improver. etc.
- an addition agent such as a detergent, an extreme pressure agent, a foam suppressor, a viscosity index (V. I.) improver. etc.
- Typical detergents which may be so used are metal salts of alkyl-substituted aromatic sulfonic or carboxylic acids, as illustrated by diwax benzene barium sulfonate and barium phenate-barium carboxylate of a wax-substituted phenol carboxylic acid.
- Extreme pressure agents are well known; illustrating such materials are numerous chlorine and/or sulfur containing compositions, one such material being a chlornaptha xanthate.
- Silicones such as dimethyl silicone, may be used to illustrate foam suppressing compositions.
- Viscosity index improving agents which may be used are typified by polypropylenes, polyisobutylenes, polyacrylate esters and the like.
- the process for converting a normal, alpha mono-olefin having from six to about twelve carbon atoms per molecule, to a viscous oil characterized by high viscosity index and low pour point which comprises: heating said olefin with lead tetra-acetate at a temperature between about 400 F. and about 700 F. for a period of time from about ten hours to about one hour, respectively, and under a pressure sufiicient to maintain the olefin in substantially the liquid phase.
- the process for converting a normal, alpha mono-olefin having from six to about twelve carbon atoms per molecule, to a viscous oil characterized by high viscosity index and low pour point which comprises: heating said olefin with from about 0.02 mol to about 0.4 mol of lead tetraacetate, per mol of said olefin, at a temperature between about 400 F. and about 700 F. for a period of time from about ten hours to about one hour, respectively, and under a pressure sufficient to maintain the olefin in substantially the liquid phase.
- the process for converting n-decene-l to a viscous oil characterized by high viscosity index and low pour point which comprises: heating n-decene-l with from about 0.02 mol to about 0.4 mol of lead tetra-acetate, per mol of n-decene-l, at a temperature between about 400 F. and about 700 F. for a period of time'from about ten hours to about one hour, respectively, and under a pressure sufiicient to maintain the olefin in substantially the liquid phase.
- n-decene-l to a viscous oil characterized by high viscosity index and low pour point, which comprises: heating one molar proportion of n-decene-l with about 0.05 molar proportion of lead tetra-acetate, at a temperature of about 500 F. for about five hours and under a pressure of about 650 pounds per square inch.
- the process for converting n-decene-l to a viscous oil characterized by high viscosity index and low pour point which comprises: heating one molar proportion of n-decene-l with about 0.05 molar proportion of PhD: and with about 0.2 molar proportion of acetic anhydride, at a temperature of about 600 F. for about eleven hours and under a pressure of about 1100 pounds per square inch.
- a viscous oil characterized by high viscosity index and low pour point obtained by: heating a normal, alpha mono-olefin having from six to about twelve carbon atoms per molecule with from about 0.02 mol to about 0.4 mol of lead tetra-acetate, per mol of said olefin, at a temperature between about 400 F. and about 700 F. for a period of time from about ten hours to about one hour, respectively, and under a pressure sufficient to maintain the olefin in substantially the liquid phase.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Description
Patented Mal-.14, rose OFFICE I CONVERSION OF 1-0LEF1NS IN THE PRES- ENCE F LEAD TE'IBAACETATE Francis M. Seger, Pltman, and Alexander N.
Bachanen, Woodbury, N. 1., assignorl to Socony-Vacnnm Oil Company, Incorporated, a corporation of New York No Drawing. Application am: 14, ms,
v Serial m. 44,40
9 Claims. (o1. zoo-683.15)
This invention has to do with hydrocarbon conversion and with synthetic lubricants or viscous oils prepared by such a conversion. More specifically. the invention is concerned with a new process for converting certain mono-oleilnic hydrocarbons to lubricants of outstanding quality.
It has now been discovered that normal alpha mono-olefins having from about 6 to about 12 carbon atoms per molecule are converted to synthetic lubricants when in contact with lead tetraacetate at elevated temperatures. The synthetic lubricants so formed are characterized by high viscosity indices, low pour points and high stability. These characteristics are such as to make these lubricants suitable for use alone or blended with other lubricants.
As indicated above, the mono-olefins of this invention are normal or straight chain alpha monoolefins and contain from about 6 to about 12 carbon atoms. Such mono-olefins are normally liquid at temperatures of the order of 20-25 C. Illustrative of such mono-olefins are the following: hexene-l, octene-l, decene-l, dodecene-l, and the like. Of such olefins, decene-l is preferred in view of the particularly outstanding characteristics of the lubricants formed therefrom. It will be clear from the foregoing examples that an alpha olefin may also be referred to as a l-olefin.
Not only may the foregoing mono-oleflns be used individually, but they may also be used in admixture with each other. In addition, olefin mixtures containing a substantial proportion of such mono-olefins may be used. 'Preferred of such mixtures are those'containing a major proportion of a normal l-olefln or of normal l-olefins.
Representative of such mixtures are those obtained by the cracking of paraflin waxes and other paraflin products, and those obtained from the Fischer-Tropsch and related processes. These hydrocarbon mixtures may contain, in addition to the normal l-olefin' or normal l-olefins, such materials as: other oleflns, parailins, naphthenes and aromatics.
Lead tetra-acetate used herein to convert the foregoing normal i-olefins to synthetic lubricants is well known, as are. methods by which it may be prepared. One typical method of preparation, forexample, involves reaction of lead dioxide (PbOz) and acetic anhydride. As contemplated herein, lead tetra-acetate may be formed in situ, as from lead dioxide and acetic anhydride. 7
Conversion or the foregoing normal l-olefins in the presence of lead tetra-acetate is eflected at elevated temperatures between about 400 F. and
F. The pressure to be employed depends upon the temperature used, and ordinarily a pressure suflicient to maintain the olefin in substantially the liquid phase is adequate. With temperatures within the 500-700" F. range, pressures of the order of 300-600 pounds per square inch are generally developed in the reaction vessel used. Reaction times will vary depending upon the particular olefin involved, quantity of olefin, temperature and, to a certain extent, pressure. In general, the higher the temperature employed, the shorter the reaction time required, the criterion used being the time required at a given reaction temperature to eflect substantial conversion of the normal l-olefin to a viscous oil. Generally, reaction times within the range of 1 to 10 hours are satisfactory.
With regard to proportions of olefin and lead tetra-acetate, satisfactory results may be obtained with as little as one mol of lead tetraacetate to fifty mols of a given normal l-olefin.
In such cases, however, much of the olefin is usually recovered unreacted. Large proportions of lead tetra-acetate, however, result in waste of this relatively expensive material without realizing corresponding enhancement of the. desired product. Excellent results are realized with from about 0.02 mol to about 0.4 mol of lead tetraacetate per mol of normal 1--olefin.
The process .contemplated herein is rather sim-' ply accomplished by mixing the normal l-olefin. and lead tetra-acetate in a shaker bomb type of reactor, replacing the air therein by an inert atmosphere of nitrogen or the like, and applying the desired temperature and pressure for a suflicient length of time to complete the conversion. It will be apparent to those skilled in the art that the process may be carried out in a batch procedure such as indicated, or may be carried out in a continuous or semi-continuous operation of the type ,widely used in the petroleum industry.
The following detailed examples are provided for the purpose of illustrating the process of this invention. It is to be understood, howeventhat the invention is not to be' considered as limited to I the specific normal l-olefin shown, or the conditions or operation set forth therein.
Example I A typical conversion was accomplished as follows: A. shaker bomb was charged with 280 grams (2.0 mols) of decene-l and 44 grams (0.1 mol) of lead tetraacetate. The air therein was replaced with nitrogen and the bomb heated toapproxi- 3 mately 500 F. (260 C.) for five hours. A pressure of 650 pounds per square inch developed in the bomb during the run.
The liquid contents of the bomb were filtered free of the relatively large amount of lead salt which was found to be present. A small amount of unreacted decene-l was distilled out at atmospheric pressure. A vacuum distillate cut was collected up to approximately 200 C. at 2 millimeters pressure. The residual oil weighed 60 grams and had the following characteristics:
Viscosity at 100 F., centistokes 44.22 Viscosity at 210 F. centistokes 7.40 Viscosity at 100 F., Saybolt, secs. 204.8 Viscosity at 210 F., Saybolt, secs 50.37 Viscosity index 132.6 Specific gravity 0.8423 Gravity, A. P. I 36.5 Neutralization number (N. N.) 0.5 Saponification number 4.5
Example II Decene-l was in contact with lead peroxide or dioxide (PbOa) and acetic anhydride, which most probably formed lead tetra-acetate in situ. The quantities used were: 280 grams (2.0 mols) of decene-l; 24 grams (0.1 mol) of PhD: and 41 grams (0.4 mol) of acetic anhydride.
The conversion and recovery procedures were effected in the manner described in Example I, with the temperature, pressure and time, respectively: 610 F. (321 0.), 1100 pounds per square inch, and 11 hours. The residual oil, 89 grams, thus obtained had the following characteristics:
Viscosity at 210 F., Saybolt, secs 47.27 Viscosity index 136.1
Specific gravity 0.8348 Neutralization number (N .N.) 0.3 Bromine number 12.6 Refractive index 1.4654
Pour point 30 It will be apparent that the present invention provides an efilcient and commercially feasible process for eflecting the conversion of normal l-olefins, of the character described above. This process is oi. value in the manufacture of synthetic lubricating oils, as well as in the manufacture of organic products (as the intermediate oils of Examples I and II) important as intermediates in organic synthesis.
From the characteristics of the products produced in the illustrative examples above, it will be apparent that the products are highly useful in reducing friction when placed between relatively moving parts, either alone or when blended with other lubricating oils. The synthetic oils impart desirable viscosity index (V. I.) and pour point characteristics to the oils in combination therewith, for, as indicated above, they have advantageous viscosity index and pour point properties. In short, the synthetic oils find utility in upgrading" other lubricants. Typical oils with which the synthetic oils may be blended are mineral oils such as are normally used in internal combustion and turbine engines. When so blended, the synthetic oils may comprise the major proportion of the final blended oil, or may even comprise a minor proportion thereof.
One or more of the individual properties of the synthetic lubricants of this invention may be further improved by incorporating therewith a small, but effective amount, of an addition agent such as a detergent, an extreme pressure agent, a foam suppressor, a viscosity index (V. I.) improver. etc. Typical detergents which may be so used are metal salts of alkyl-substituted aromatic sulfonic or carboxylic acids, as illustrated by diwax benzene barium sulfonate and barium phenate-barium carboxylate of a wax-substituted phenol carboxylic acid. Extreme pressure agents are well known; illustrating such materials are numerous chlorine and/or sulfur containing compositions, one such material being a chlornaptha xanthate. Silicones, such as dimethyl silicone, may be used to illustrate foam suppressing compositions. Viscosity index improving agents which may be used are typified by polypropylenes, polyisobutylenes, polyacrylate esters and the like.
contemplated also as within the scope of this invention, is a method of lubricating relatively moving surfaces by maintaining therebetween a film consisting of any of the aforesaid synthetic lubricants and blends thereof.
It is to be understood that the foregoing description and representative examples are nonlimiting and serve to illustrate the invention, which is to be broadly construed in the light of the language of the appended claims.
We claim:
1. The process for converting a normal, alpha mono-olefin having from six to about twelve carbon atoms per molecule, to a viscous oil characterized by high viscosity index and low pour point, which comprises: heating said olefin with lead tetra-acetate at a temperature between about 400 F. and about 700 F. for a period of time from about ten hours to about one hour, respectively, and under a pressure sufiicient to maintain the olefin in substantially the liquid phase.
2. The process for converting a normal, alpha mono-olefin having from six to about twelve carbon atoms per molecule, to a viscous oil characterized by high viscosity index and low pour point, which comprises: heating said olefin with from about 0.02 mol to about 0.4 mol of lead tetraacetate, per mol of said olefin, at a temperature between about 400 F. and about 700 F. for a period of time from about ten hours to about one hour, respectively, and under a pressure sufficient to maintain the olefin in substantially the liquid phase.
3. The process for converting n-decene-l to a viscous oil characterized by high viscosity index and low pour point, which comprises: heating n-decene-l with from about 0.02 mol to about 0.4 mol of lead tetra-acetate, per mol of n-decene-l, at a temperature between about 400 F. and about 700 F. for a period of time'from about ten hours to about one hour, respectively, and under a pressure sufiicient to maintain the olefin in substantially the liquid phase.
4. The process for converting n-decene-l to a viscous oil characterized by high viscosity index and low pour point, which comprises: heating one molar proportion of n-decene-l with about 0.05 molar proportion of lead tetra-acetate, at a temperature of about 500 F. for about five hours and under a pressure of about 650 pounds per square inch.
5. The process for converting n-decene-l to a viscous oil characterized by high viscosity index and low pour point, which comprises: heating one molar proportion of n-decene-l with about 0.05 molar proportion of PhD: and with about 0.2 molar proportion of acetic anhydride, at a temperature of about 600 F. for about eleven hours and under a pressure of about 1100 pounds per square inch.
ll 6. A viscous oil characterized by high viscosity index and low pour point. and obtained by: heating a normal, alpha mono-olefin having from six to about twelve carbon atoms per molecule with lead tetra-acetate at a temperature between about 400 F. and about 700 F. for a period of time from about ten hours to about one hour, respectively, and under a pressure sufiicient to maintain the olefin in substantially the liquid phase.
7. A viscous oil characterized by high viscosity index and low pour point, and obtained by: heating a normal, alpha mono-olefin having from six to about twelve carbon atoms per molecule with from about 0.02 mol to about 0.4 mol of lead tetra-acetate, per mol of said olefin, at a temperature between about 400 F. and about 700 F. for a period of time from about ten hours to about one hour, respectively, and under a pressure sufficient to maintain the olefin in substantially the liquid phase.
8. A viscous oil characterized by high viscosity index and low pour point, and obtained by: heating one molar proportion of n-decene-l with about 0.05 molar proportion of PhD: and with about 0.2 molar proportion of acetic anhydride, at a temperature of about 600 F. for about eleven liours and under a pressure of about 100 pounds per square inch.
FRANCIS M. SEGER. ALEXANDER N. SACHANEN.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Number Name Date 2,091,398 Sullivan et al. Aug. 31, 1937 2,117,022 Cramer May 10, 1938 2,262,804 Jean Nov. 18, -1941 FOREIGN PATENTS Number Country Date 366,112 Great Britain Jan. 25, 1932 OTHER REFERENCES Hutchinson et al.: Jour. Chem. Soc. (London), vol. 69 (1896), pages 212-221.
Claims (1)
1. THE PROCESS FOR CONVERTING A NORMAL, ALPHA MONO-OLEFIN HAVING FROM SIX TO ABOUT TWELVE CARBON ATOMS PER MOLECULE, TO A VISCOUS OIL CHARACTERIZED BY HIGH VISCOSITY INDEX AND LOW POUR POINT, WHICH COMPRISES: HEATING SAID OLEFIN WITH LEAD TETRA-ACETATE AT A TEMPERATURE BETWEEN ABOUT 400*F. AND ABOUT 700*F. FOR A PERIOD OF TIME FROM ABOUT TEN HOURS TO ABOUT ONE HOUR, RESPECTIVELY, AND UNDER A PRESSURE SUFFICIENT TO MAINTAIN THE OLEFIN IN SUBSTANTIALLY THE LIQUID PHASE.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44403A US2500161A (en) | 1948-08-14 | 1948-08-14 | Conversion of 1-olefins in the presence of lead tetraacetate |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44403A US2500161A (en) | 1948-08-14 | 1948-08-14 | Conversion of 1-olefins in the presence of lead tetraacetate |
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| US2500161A true US2500161A (en) | 1950-03-14 |
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| Application Number | Title | Priority Date | Filing Date |
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| US44403A Expired - Lifetime US2500161A (en) | 1948-08-14 | 1948-08-14 | Conversion of 1-olefins in the presence of lead tetraacetate |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3149178A (en) * | 1961-07-11 | 1964-09-15 | Socony Mobil Oil Co Inc | Polymerized olefin synthetic lubricants |
| US5396013A (en) * | 1993-07-12 | 1995-03-07 | Albemarle Corporation | Olefin oligomerization process |
| US5633420A (en) * | 1995-09-22 | 1997-05-27 | Amoco Corporation | Olefin oligomerization process |
| US5650548A (en) * | 1995-06-16 | 1997-07-22 | Amoco Corporation | Olefin oligomerization process |
| US5744676A (en) * | 1996-02-26 | 1998-04-28 | Theriot; Kevin J. | Olefin oligomerization process |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB366112A (en) * | 1930-10-24 | 1932-01-25 | Ig Farbenindustrie Ag | Improvements in the manufacture and production of valuable hydrocarbons from gaseoushydrocarbons |
| US2091398A (en) * | 1931-03-21 | 1937-08-31 | Standard Oil Co | Synthesis of lubricating oils |
| US2117022A (en) * | 1934-01-04 | 1938-05-10 | Gen Motors Corp | Conversion of hydrocarbons |
| US2262804A (en) * | 1939-01-31 | 1941-11-18 | James W Jean | Catalyst |
-
1948
- 1948-08-14 US US44403A patent/US2500161A/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB366112A (en) * | 1930-10-24 | 1932-01-25 | Ig Farbenindustrie Ag | Improvements in the manufacture and production of valuable hydrocarbons from gaseoushydrocarbons |
| US2091398A (en) * | 1931-03-21 | 1937-08-31 | Standard Oil Co | Synthesis of lubricating oils |
| US2117022A (en) * | 1934-01-04 | 1938-05-10 | Gen Motors Corp | Conversion of hydrocarbons |
| US2262804A (en) * | 1939-01-31 | 1941-11-18 | James W Jean | Catalyst |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3149178A (en) * | 1961-07-11 | 1964-09-15 | Socony Mobil Oil Co Inc | Polymerized olefin synthetic lubricants |
| US5396013A (en) * | 1993-07-12 | 1995-03-07 | Albemarle Corporation | Olefin oligomerization process |
| US5650548A (en) * | 1995-06-16 | 1997-07-22 | Amoco Corporation | Olefin oligomerization process |
| US5633420A (en) * | 1995-09-22 | 1997-05-27 | Amoco Corporation | Olefin oligomerization process |
| US5744676A (en) * | 1996-02-26 | 1998-04-28 | Theriot; Kevin J. | Olefin oligomerization process |
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