US3350360A - Separation of olefins from aluminum trialkoxides - Google Patents
Separation of olefins from aluminum trialkoxides Download PDFInfo
- Publication number
- US3350360A US3350360A US596830A US59683066A US3350360A US 3350360 A US3350360 A US 3350360A US 596830 A US596830 A US 596830A US 59683066 A US59683066 A US 59683066A US 3350360 A US3350360 A US 3350360A
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- US
- United States
- Prior art keywords
- aluminum
- trialkoxide
- carbon atoms
- hydrocarbon
- olefins
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229910052782 aluminium Inorganic materials 0.000 title claims description 40
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 title claims description 38
- 150000001336 alkenes Chemical class 0.000 title claims description 23
- 238000000926 separation method Methods 0.000 title description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 17
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 12
- 238000000638 solvent extraction Methods 0.000 claims description 6
- 238000000622 liquid--liquid extraction Methods 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 description 19
- 150000002430 hydrocarbons Chemical class 0.000 description 19
- 239000004215 Carbon black (E152) Substances 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- 238000000605 extraction Methods 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 10
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- -1 aluminum tritetracosoxy, aluminum tripentacosoxy, aluminum trihexacosoxy, aluminum triheptacosoxy, aluminum Chemical compound 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 241001647090 Ponca Species 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229910018516 Al—O Inorganic materials 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
- C07C29/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups with molecular oxygen only
- C07C29/54—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups with molecular oxygen only starting from compounds containing carbon-to-metal bonds and followed by conversion of the -O- metal to -OH groups
Definitions
- This invention relates to a method of separating olefins from aluminum trialkoxides.
- Aluminum trialkyls are oxidized to aluminum trialkoxides which in turn are hydrolyzed to alcohols.
- the growth of aluminum trialkyls with ethylene produces olefins as by-product materials which are removed prior to the hydrolysis step.
- the removal of olefins may be accomplished by distillation, stripping, etc.
- An object of this invention is to provide a method of separating olefins from aluminum trialkoxides.
- Another object of this invention is to provide a simple and eliective method of removing olefins from aluminum trialkoxides.
- aluminum trialkoxide containing a small amount of olefin is extracted with a hydrocarbon which contains on the average about 20 to 25 carbon atoms less than the average number of carbon atoms contained in the alkyl substituents of the aluminum trialkoxide.
- the hydrocarbon employed as an extraction solvent is preferably saturated and aliphatic in type.
- the hydrocarbon includes the parafiinic hydrocarbons having a boiling point of about 36 to 215 C., preferably about 36 to 100 C.
- the hydrocarbon may be a single compound, such as: pentane, hexane, heptane, etc., or a mixture of hydrocarbons, such as a petroleum fraction, which has an A.S.T.M. initial boiling point of about 36 to 100 C. and an end point of about 85 to 100 C.
- Specific examples of petroleum fractions are petroleum ether, natural gasoline, light hydrocarbon fraction containing C to C hydrocarbons, etc.
- the hydrocarbon solvent may have a ICC boiling point of about 35 to 215 0., preferably about to 250 C. less than the olefin being extracted.
- R R and R are the same or different alkyl groups, and the average of R R and R varies from about 24 to 36 carbon atoms, more usually about 26 to 34 carbon atoms.
- Specific examples of aluminum trialkoxide are aluminum tritetracosoxy, aluminum tripentacosoxy, aluminum trihexacosoxy, aluminum triheptacosoxy, aluminum octacosoxy, aluminum nonacosoxy, aluminum triacontoxy, aluminum trihentriacontoxy, aluminum tridotriacontoxy, etc., and admixtures thereof.
- the aluminum trialkoxide is contaminated with olefinic material.
- the olefinic material may be a single compound or a mixture of compounds.
- the olefinic compounds may be monoor diunsaturated and may contain about 16 to 36 carbon atoms, more usually about 18 to 26 carbon atoms.
- the olefinic material is present with the aluminum trialkoxide in an amount of about 0.5 to 30 percent by weight, more usually about 1 to 9 percent by weight. Greater or less amounts of olefinic material may be present in the aluminum trialkoxide; however, the present invention is uniquely adapted for removal of relatively small quantities of olefinic material from the aluminum trialkoxide.
- the extraction of olefin is usually conducted at a temperature of about 35 to 215 C., preferably about 35 to 100 C., and at a pressure of about 1 to 30 p.s.i.a., preferably about one atmosphere.
- the extraction time is about 1 to 24 hours, preferably about 4 to 12 hours.
- the conditions of extraction can be varied still more from What is described above and be Within the scope of the present invention.
- the extraction step can be accomplished by co-current or countercurrent flow, or by the simple batch technique.
- the countercurrent technique is preferred; however, any of the methods can be used for my invention.
- the hexane insoluble material was hydrolyzed by means of diulte HCl.
- the organic layer after hydrolysis was found to contain 33.4 percent hydrocarbon.
- Example 2 50 grams of the aluminum trialkoxide described in Example 1 and 400 ml. of petroleum ether having an A.S.T.M. boiling range of 30 to 60 C. were charged to the same extractor as used in Example 1. The extraction took 32 hours. The solvent-soluble fraction was hydrolyzed with 25 percent HCl to give an organic phase containing 61.5 percent hydrocarbon. The solvent insoluble fraction was also hydrolyzed with 25 percent HCl and the organic phase contained 30.8 percent hydrocarbon.
- Example 3 450 ml. of dry n-hexane and 18.2 gm. of aluminum trialkyl prepared by reacting aluminum triethyl with ethylene at 120 C. and 1,500 p.s.i.g. to form a product (same as Example 1) having an average of 30 carbon atoms per substituent and which is oxidized with air at 50-70" C. until oxidation ceased is added to a Soxhlet extractor equipped with a calcium chloride drier.
- the thimble employed is a Green No. 703. The extraction is continued for 24 hours.
- the hexane soluble portion is found to be 7.2 grams.
- the hexane insoluble material is hydrolyzed by means of dilute HCl.
- the organic layer is found to contain 33.4 percent hydrocarbon. Analysis of this hydrocarbon material discloses that it is essentially saturated hydrocarbons with less than about 2 percent olefins. It is believed that the saturated hydrocarbons result from the hydrolysis of unoxidized aluminum alkyls.
- a process which comprises extracting olefinic material having an average number of carbon atoms of about 16 to 36 from an aluminum trialkoxide having alkyl substituents containing an average number of carbon atoms of about 24 to 36 by means of liquid-liquid extraction with an aliphatic hydrocarbon having an average number of carbon atoms of about 20 to 25 less than said aluminum trialkoxide.
- a process which comprises extracting olefinic material having an average number of carbon atoms of about l636 from an aluminum trialkoxide having alkyl substituents containing an average number of carbon atoms of about 24-36 by means of liquid-liquid extraction with an aliphatic hydrocarbon having a boiling point of about 36215 C.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
Description
United States Patent 3,350,360 SEPARATIQN 0F OLEFINS FROM ALUMINUM TRIALKOXIDES Giliord G. McClafiin, Ponca City, Okla, assignor to Continental Oil Company, Ponca City, Okla, a corporation of Delaware No Drawing. Filed Nov. 25, 1966, Ser. No. 596,830
8 Claims. (Cl. 260-677) ABSTRACT OF THE DISCLOSURE A mixture of aluminum trialkoxides having an average of about 24 to 36 carbons per alkyl, and olefins having an average of about 16 to 36 carbons, is separated by liquidliquid extraction using as solvent an aliphatic hydrocarbon having an average of about 20 to 25 carbons less than the trialkoxide.
Cross-reference to related application This is a continuation-in-part of the co-pending application of the present inventor, entitled, Separation of Olefins From Aluminum Trialkoxides, Serial No. 132,- 544, filed Aug. 21, 1961, now abandoned.
Disclosure This invention relates to a method of separating olefins from aluminum trialkoxides. Aluminum trialkyls are oxidized to aluminum trialkoxides which in turn are hydrolyzed to alcohols. The growth of aluminum trialkyls with ethylene produces olefins as by-product materials which are removed prior to the hydrolysis step. The removal of olefins may be accomplished by distillation, stripping, etc. Unfortunately,
such methods involve subjecting the aluminum trialkoxide to heat; consequently, there is a tendency for undesirable decomposition reactions to occur. The problem is further aggravated by the fact that the olefin is usually present in relatively small amounts, viz, up to about 9 percent by weight of the aluminum trialkoxide material; so care must be taken to avoid loss of the trialkoxide. Following an extensive investigation of this problem, quite surprisingly, I have discovered a simple, eliective and inexpensive solution.
An object of this invention is to provide a method of separating olefins from aluminum trialkoxides.
Another object of this invention is to provide a simple and eliective method of removing olefins from aluminum trialkoxides.
Other objects and advantages of this invention will become apparent from the following description and explanation thereof.
In accordance with this invention, aluminum trialkoxide containing a small amount of olefin is extracted with a hydrocarbon which contains on the average about 20 to 25 carbon atoms less than the average number of carbon atoms contained in the alkyl substituents of the aluminum trialkoxide.
The hydrocarbon employed as an extraction solvent is preferably saturated and aliphatic in type. The hydrocarbon includes the parafiinic hydrocarbons having a boiling point of about 36 to 215 C., preferably about 36 to 100 C. The hydrocarbon may be a single compound, such as: pentane, hexane, heptane, etc., or a mixture of hydrocarbons, such as a petroleum fraction, which has an A.S.T.M. initial boiling point of about 36 to 100 C. and an end point of about 85 to 100 C. Specific examples of petroleum fractions are petroleum ether, natural gasoline, light hydrocarbon fraction containing C to C hydrocarbons, etc. The hydrocarbon solvent may have a ICC boiling point of about 35 to 215 0., preferably about to 250 C. less than the olefin being extracted.
The hydrocarbon extraction solvent is sufiiciently close in property to the high boiling olefin so that substantially all or a significant amount is dissolved in the solvent upon extraction of the mixture of aluminum trialkoxide and olefin therewith. The aluminum trialkoxide, on the other hand, is substantially insoluble or significantly less soluble so that it remains essentially out of solution with re spect to the hydrocarbon solvent. The aluminum trialkoxide contains about 10 to 30 percent by weight, more usually about 10 to 20 percent by weight of olefin. The aluminum trialkoxide is extracted with hydrocarbon solvent in relative quantities of about 2 to 50 parts by weight of solvent per unit weight of aluminum trialkoxide, preferably about 5 to 15 parts by weight of solvent per unit weight of aluminum trialkoxide.
The aluminum trialkoxide of the present invention has the following formula:
/OR1 Al-O R2 wherein R R and R are the same or different alkyl groups, and the average of R R and R varies from about 24 to 36 carbon atoms, more usually about 26 to 34 carbon atoms. Specific examples of aluminum trialkoxide are aluminum tritetracosoxy, aluminum tripentacosoxy, aluminum trihexacosoxy, aluminum triheptacosoxy, aluminum octacosoxy, aluminum nonacosoxy, aluminum triacontoxy, aluminum trihentriacontoxy, aluminum tridotriacontoxy, etc., and admixtures thereof.
The aluminum trialkoxide is contaminated with olefinic material. The olefinic material may be a single compound or a mixture of compounds. The olefinic compounds may be monoor diunsaturated and may contain about 16 to 36 carbon atoms, more usually about 18 to 26 carbon atoms. The olefinic material is present with the aluminum trialkoxide in an amount of about 0.5 to 30 percent by weight, more usually about 1 to 9 percent by weight. Greater or less amounts of olefinic material may be present in the aluminum trialkoxide; however, the present invention is uniquely adapted for removal of relatively small quantities of olefinic material from the aluminum trialkoxide.
The extraction of olefin is usually conducted at a temperature of about 35 to 215 C., preferably about 35 to 100 C., and at a pressure of about 1 to 30 p.s.i.a., preferably about one atmosphere. The extraction time is about 1 to 24 hours, preferably about 4 to 12 hours. The conditions of extraction can be varied still more from What is described above and be Within the scope of the present invention. The extraction step can be accomplished by co-current or countercurrent flow, or by the simple batch technique. The countercurrent technique is preferred; however, any of the methods can be used for my invention.
For a fuller understanding of the present invention, reference will be had to the following specific examples.
Example .I
450 ml. of dry n-hexane and 18.2 gm. of aluminum trialkyl prepared by reacting aluminum triethyl with ethylene at C. and 1,500 p.s.i.g. to form a product having an average of 30 carbon atoms per substituent and which was oxidized with air at 5070 C. until oxidation ceased were added to a Soxhlet extractor equipped with a calcium chloride drier. The thimble employed was a Green No. 703. The extraction occurred for 24 hours. The hexane soluble portion was found to be 7.2 grams.
The hexane insoluble material Was hydrolyzed by means of diulte HCl. The organic layer after hydrolysis was found to contain 33.4 percent hydrocarbon. The aluminum alkoxide when hydrolyzed with the solvent extraction step omitted yielded a product containing 45.0 percent hydrocarbon. Analysis of this hydrocarbon material discloses that about 33 percent is saturated hydrocarbons and about 12 percent is olefins.
Example 2 50 grams of the aluminum trialkoxide described in Example 1 and 400 ml. of petroleum ether having an A.S.T.M. boiling range of 30 to 60 C. were charged to the same extractor as used in Example 1. The extraction took 32 hours. The solvent-soluble fraction was hydrolyzed with 25 percent HCl to give an organic phase containing 61.5 percent hydrocarbon. The solvent insoluble fraction was also hydrolyzed with 25 percent HCl and the organic phase contained 30.8 percent hydrocarbon.
Example 3 450 ml. of dry n-hexane and 18.2 gm. of aluminum trialkyl prepared by reacting aluminum triethyl with ethylene at 120 C. and 1,500 p.s.i.g. to form a product (same as Example 1) having an average of 30 carbon atoms per substituent and which is oxidized with air at 50-70" C. until oxidation ceased is added to a Soxhlet extractor equipped with a calcium chloride drier. The thimble employed is a Green No. 703. The extraction is continued for 24 hours. The hexane soluble portion is found to be 7.2 grams. The hexane insoluble material is hydrolyzed by means of dilute HCl. The organic layer is found to contain 33.4 percent hydrocarbon. Analysis of this hydrocarbon material discloses that it is essentially saturated hydrocarbons with less than about 2 percent olefins. It is believed that the saturated hydrocarbons result from the hydrolysis of unoxidized aluminum alkyls.
It is apparent from the foregoing examples that the process of this invention produces a product which is greatly reduced in olefin content.
Having thus described the invention by providing specific examples thereof, it is to be understood that no undue limitations or restrictions are to be drawn by reason thereof and that many variations and modifications are within the scope of the invention.
I claim:
1. A process which comprises extracting olefinic material having an average number of carbon atoms of about 16 to 36 from an aluminum trialkoxide having alkyl substituents containing an average number of carbon atoms of about 24 to 36 by means of liquid-liquid extraction with an aliphatic hydrocarbon having an average number of carbon atoms of about 20 to 25 less than said aluminum trialkoxide.
2. The process of claim 1 wherein the temperature of extraction is about 35 to 215 C. and the pressure about 1 to 30 p.s.i.a.
3. The process of claim 1 wherein the aliphatic hydrocarbon is a petroleum fraction.
4. The process of claim 1 wherein the aliphatic hydrocarbon is petroleum ether.
5. The process of claim 1 wherein the aliphatic hydrocarbon is n-hexane.
6. The process which comprises extracting from aluminum trialkoxide having an average number of carbon atoms per substituent in the order of about 30 and contaminated with not more than about 30 percent of olefin having the same average number of carbon atoms by liquid-liquid extraction with n-hexane to remove a substantial amount of olefin from the aluminum trialkoxide.
7. A process which comprises extracting olefinic material having an average number of carbon atoms of about l636 from an aluminum trialkoxide having alkyl substituents containing an average number of carbon atoms of about 24-36 by means of liquid-liquid extraction with an aliphatic hydrocarbon having a boiling point of about 36215 C.
8. A process according to claim 7 wherein the boiling point of the aliphatic hydrocarbon is about 36lOO C.
References Cited UNITED STATES PATENTS 2,863,895 6/1956 Kirshenbaum et al. 260448 2,892,858 6/1959 Ziegler 260448 3,062,857 1/1960 Acciarri et al. 260448 DELBERT E. GANTZ, Primary Examiner.
I. D. MYERS, Assistant Examiner.
Claims (1)
- 6. THE PROCESS WHICH COMPRISES EXTRACTING FROM ALUMINUM TRIALKOXIDE HAVING AN AVERAGE NUMBER OF CARBON ATOMS PER SUBSTITUENT IN THE ORDER OF ABOUT 36 AND CONTAMINATED WITH NOT MORE THAN ABOUT 30 PERCENT OF OLEFIN HAVING THE SAME AVERAGE NUMBER OF CARBON ATOMS BY LIQUID-LIQUID EXTRACTION WITH N-HEXANE TO REMOVE A SUBSTANTIAL AMOUNT OF OLEFIN FROM THE ALUMINUM TRIALKOXIDE.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US596830A US3350360A (en) | 1966-11-25 | 1966-11-25 | Separation of olefins from aluminum trialkoxides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US596830A US3350360A (en) | 1966-11-25 | 1966-11-25 | Separation of olefins from aluminum trialkoxides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3350360A true US3350360A (en) | 1967-10-31 |
Family
ID=24388885
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US596830A Expired - Lifetime US3350360A (en) | 1966-11-25 | 1966-11-25 | Separation of olefins from aluminum trialkoxides |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3350360A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3655520A (en) * | 1969-03-06 | 1972-04-11 | Ethyl Corp | Distillation of olefins with alkanol addition to prevent degradation |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2863895A (en) * | 1956-06-12 | 1958-12-09 | Exxon Research Engineering Co | Method of oxidizing aluminum alkyls |
| US2892858A (en) * | 1959-06-30 | Certificate of correction | ||
| US3062857A (en) * | 1960-01-14 | 1962-11-06 | Continental Oil Co | Process for the purifying metal alkoxides with a lower nitroalkane |
-
1966
- 1966-11-25 US US596830A patent/US3350360A/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2892858A (en) * | 1959-06-30 | Certificate of correction | ||
| US2863895A (en) * | 1956-06-12 | 1958-12-09 | Exxon Research Engineering Co | Method of oxidizing aluminum alkyls |
| US3062857A (en) * | 1960-01-14 | 1962-11-06 | Continental Oil Co | Process for the purifying metal alkoxides with a lower nitroalkane |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3655520A (en) * | 1969-03-06 | 1972-04-11 | Ethyl Corp | Distillation of olefins with alkanol addition to prevent degradation |
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