US2948762A - Process for preparing alkaline metals having high reactive power - Google Patents
Process for preparing alkaline metals having high reactive power Download PDFInfo
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- US2948762A US2948762A US646553A US64655357A US2948762A US 2948762 A US2948762 A US 2948762A US 646553 A US646553 A US 646553A US 64655357 A US64655357 A US 64655357A US 2948762 A US2948762 A US 2948762A
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- Prior art keywords
- sodium
- metal
- anthracene
- hydrocarbon
- alkali
- Prior art date
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- Expired - Lifetime
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- 229910052751 metal Inorganic materials 0.000 title description 22
- 239000002184 metal Substances 0.000 title description 22
- 238000004519 manufacturing process Methods 0.000 title description 5
- 150000002739 metals Chemical class 0.000 title description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 19
- 150000002430 hydrocarbons Chemical class 0.000 claims description 19
- 239000004215 Carbon black (E152) Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 3
- 150000001339 alkali metal compounds Chemical class 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 26
- 229910052708 sodium Inorganic materials 0.000 description 13
- 239000011734 sodium Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 8
- 238000007792 addition Methods 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000000203 mixture Substances 0.000 description 6
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 5
- 235000021286 stilbenes Nutrition 0.000 description 5
- 238000004448 titration Methods 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 150000001491 aromatic compounds Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- -1 tri-sodium anthracene Chemical compound 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000005662 Paraffin oil Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- QAUVECTWHJILLI-UHFFFAOYSA-N [Na]C1C2=CC=CC=C2C([Na])C2=C1C=CC=C2 Chemical compound [Na]C1C2=CC=CC=C2C([Na])C2=C1C=CC=C2 QAUVECTWHJILLI-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 150000003388 sodium compounds Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PGTKVMVZBBZCKQ-UHFFFAOYSA-N Fulvene Chemical compound C=C1C=CC=C1 PGTKVMVZBBZCKQ-UHFFFAOYSA-N 0.000 description 1
- QXOPMVCCPTYJPU-UHFFFAOYSA-N anthracene;sodium Chemical class [Na].C1=CC=CC2=CC3=CC=CC=C3C=C21 QXOPMVCCPTYJPU-UHFFFAOYSA-N 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229920005547 polycyclic aromatic hydrocarbon Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J16/00—Chemical processes in general for reacting liquids with non- particulate solids, e.g. sheet material; Apparatus specially adapted therefor
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic System
Definitions
- hydrocarbons containing more than 'twomolecules of alkaline metal per molecule of addition compound are decomposed with alcohol or Water, a quantity of hydrogen is obtained which in most cases corresponds approximately to the quantity of x minus 2, Where x represents the quantity in molecules of alkaline metal that is absorbed by the hydrocarbon. It then for instance six molecules of sodium-areabsorbed by one molecule of anthracene and the compound formed is decomposed with water, there is obtained a quantity of hydrogen that corresponds about to tour molecules of sodium.
- alkaline metals are extraordinarily simple. It is only necessary to treat with the alkaline metal a suitable hydrocarbon in an inert solvent or in a suspending medium such as toluene, xylene, parafiin oil etc., preferably at elevated temperature and excluding water and the oxygen of air.
- a suitable hydrocarbon in an inert solvent or in a suspending medium such as toluene, xylene, parafiin oil etc., preferably at elevated temperature and excluding water and the oxygen of air.
- the comparatively elevated temperature indicated above is not indispensable; however, with to reduce the duration of the reaction. If operating at temperatures beyond the meltingpoint of the alkaline metal, it is not always necessary to employ the alkaline metal finely distributed. It is possible to employ even pieces of any size. I i S'oitisnot always necessary toadd the wholequantity of alkaline metal that one wants toadd tothe hydrocarbon, at once at the beginning, although this be the preferred method or production. Above all if itis desired to carry out this reaction for the first time with a new hydrocarbon it may be advisable to use first only 2 molecules of alkaline metalper molecule of desired addition compound and to add further alkaline metal after those molecules having been absorbed completely. These addition compounds appear as; heavy colored powders, mostly of black bluish color orblack towards brown color, which separate from the solvent or from the suspension medium in the shape of Antiesand.
- Hydrocarbons suitable are for instance anthracene, phenanthrene, stilbene, diphenyl' butadiene, fulvene and others.
- V i I V The alkaline-organic addition compounds containing more than two molecules of metal per molecule of hydrocarbon, can be employedin lieu ofthe alkaline metal, for instance-asreducing agents in organic 'dgemis'try or in the polymerization of butadiene catalyzed by means of alkali metal. These sodium compounds" and; processes of making them and uses as actuators ofj'catalysts are described but not claimed in; our copending applications Serial Nos. 646,552 and 646,554 filed March 18, 1957,
- Example-1 To 170 g. of anhydrous xylene in a nitrogen atmosphere there are. added. 25.8 'g. of sodium finely comminuted, and: 20g; of 'anth-racene. 'Fhe mixture is stirred at first for two hours at ordinary temperaturefand then from 0.1 to 0.2 g. of e rsodiurn anthracene are added. The mixture is slowly heated to C its color becomesintensive blue already in thecold "on'as soonas the temperature begins 'to rise.
- the ratio b :a is equal to 1:0.78 or 10 mol:7.8 mol.
- the ratio b ra is therefore equal to 1:0.77 or 10 mol:7.7 mol.
- Example 2 Into 150 g. of paraffin oil free from water and in a nitrogen atmosphere there are introduced 10.3 g. of comminuted sodium and 19.9 g. of anthracene. The mixture is stirred for four hours at normal temperature, 0.1 g. of tetra-sodium anthracene is added and the mass is heated for three hours up to 110 C. In most cases already in the cold or at the beginning of heating, the suspension becomes dark-colored. After stopping the stirrer, the tetra-sodium anthracene formed separates from the clear and colorless liquid.
- the analysis (carried out as described in Example 1) give the following data:
- the ratio bza are equal to 1:0.44 and 1:05 respectively, which corresponds approximately to the ratio of 4 molecules to 2 molecules.
- Example 3 To 200 g. of anhydrous xylene in nitrogen atmosphere there are added 15.2 g. of finely comminuted sodium and 20 g. of stilbene. The mixture is stirred for 12 hours at normal temperature and in nitrogen atmosphere, 0.1 to 0.2 g. of di-sodium stilbene are added and under stirring the mass is heated for 8 hours to 100 C. The suspension becomes dark-colored at once and after stopping the stirrer the hexa-sodium stilbene separates in the shape of a brown-black colored powder.
- the analysis of two samples of the substance, carried out as described in Example 1, give the following values:
- Example 4 To 150 g. of anhydrous xylene in nitrogen atmosphere there are added 7 g. of comminuted sodium and 18.05 of anthracene. The mixture is treated as described in the preceding examples and a product is obtained the analytical values whereof, as indicated here below, correspond about to those of tri-sodium anthracene. During some experiments however it is found that the anthracene added has not reacted completely. If allowing to rest, sometimes there deposits under the clear liquid also some nontransformed anthracene.
- a process of forming an alkali-metal compound of a normally solid polynuclear aromatic hydrocarbon containing 2-10 atoms alkali-metal comprising stirring an alkali-metal with said aromatic hydrocarbon for at least about two hours in an inert anhydrous liquid hydrocarbon at atmospheric temperature under a non-oxidizing atmosphere and then heating to about C. to about C. with stirring until a dark precipitate forms.
- liquid hydrocarbon is a benzene homologue
- liquid hydrocarbon is paraffin oil
Description
PROCESS FOR PREPARING ALKALINE METALS HAVING HIGH REAQTIVE POWER N Drawing. Filed Mar 18, 1957, Ser. No. 646,553 Claims priority, application Italy Mar. 23, 1956 7 Claims- (Cl. 260-665) It is known that some hydrocarbons add finely distributed alkaline metals (Schlenk, Ben, 47, 473 (1914) )1 These hydrocarbons possess conjugated double bonds activated by aromatic groups which may be either simple or conjugated. it is also known that these hydrocarbons can add normally two metal atoms, by giving up one of those activated double bonds and in exceptional cases even only one single metal atom. In, most cases these additions of metals are efiected in ether or in a cyclic ether in the absence of water and, of the oxygen of air.
It has now been found and this represents. the object of the present invention, that these hydrocarbons are able to add not only two atoms of metal, as is indicated in the literature, but, under suitable operating conditions, a sensibly greater number of metal atoms per molecule of non-saturated hydrocarbon.
In many cases this alkali-metal linked inrexcess gives the same reactions that are caused by the free alkalimetal. I
It is not possible to define accurately the manner in which the quite considerable quantities of alkaline metal are linked by those hydrocarbons. It may be that the addition takes place by means of a progressive dissolving of all the double links, that is, also of those of the aromatic series. However, it may also be that there is only a solid solution of the alkaline metal at the surface of the hydrocarbon.
If those hydrocarbons containing more than 'twomolecules of alkaline metal per molecule of addition compound, are decomposed with alcohol or Water, a quantity of hydrogen is obtained which in most cases corresponds approximately to the quantity of x minus 2, Where x represents the quantity in molecules of alkaline metal that is absorbed by the hydrocarbon. It then for instance six molecules of sodium-areabsorbed by one molecule of anthracene and the compound formed is decomposed with water, there is obtained a quantity of hydrogen that corresponds about to tour molecules of sodium.
What has been set forth hereinbefore is true with approximative accuracy only in the case in which the first two molecules of sodium are absorbed while in mutual position 1,4, as happens with anthracene. If the first two molecules of alkalinemetal have been added in position 1,2 during the decomposition there is obtained a quantity of hydrogen slightly greater than would correspond to the formula x,-2.
The production of these addition compounds. of alkaline metals is extraordinarily simple. It is only necessary to treat with the alkaline metal a suitable hydrocarbon in an inert solvent or in a suspending medium such as toluene, xylene, parafiin oil etc., preferably at elevated temperature and excluding water and the oxygen of air.
It is advantageous but not necessary to effect this treatment in such a manner that the hydrocarbon be treated with the alkaline metal at first for the duration of one or assignors, by mesne assign-.
tates Patent 2,948,762 Patented Aug. 9,
2 more hours in the cold and keeping then the temperature further for from one to three hours above the melting point of the alkaline metal. It may even be advantageous to add at the beginning a small quantity of a metallorganic addition compound previously prepared.
The comparatively elevated temperature indicated above is not indispensable; however, with to reduce the duration of the reaction. If operating at temperatures beyond the meltingpoint of the alkaline metal, it is not always necessary to employ the alkaline metal finely distributed. It is possible to employ even pieces of any size. I i S'oitisnot always necessary toadd the wholequantity of alkaline metal that one wants toadd tothe hydrocarbon, at once at the beginning, although this be the preferred method or production. Above all if itis desired to carry out this reaction for the first time with a new hydrocarbon it may be advisable to use first only 2 molecules of alkaline metalper molecule of desired addition compound and to add further alkaline metal after those molecules having been absorbed completely. These addition compounds appear as; heavy colored powders, mostly of black bluish color orblack towards brown color, which separate from the solvent or from the suspension medium in the shape of afinesand.
Hydrocarbons suitable are for instance anthracene, phenanthrene, stilbene, diphenyl' butadiene, fulvene and others. V i I V The alkaline-organic addition compounds containing more than two molecules of metal per molecule of hydrocarbon, can be employedin lieu ofthe alkaline metal, for instance-asreducing agents in organic 'dgemis'try or in the polymerization of butadiene catalyzed by means of alkali metal. These sodium compounds" and; processes of making them and uses as actuators ofj'catalysts are described but not claimed in; our copending applications Serial Nos. 646,552 and 646,554 filed March 18, 1957,
I Example-1 To 170 g. of anhydrous xylene in a nitrogen atmosphere there are. added. 25.8 'g. of sodium finely comminuted, and: 20g; of 'anth-racene. 'Fhe mixture is stirred at first for two hours at ordinary temperaturefand then from 0.1 to 0.2 g. of e rsodiurn anthracene are added. The mixture is slowly heated to C its color becomesintensive blue already in thecold "on'as soonas the temperature begins 'to rise. {Thesodium 'whie at the beginning is perfectly "ble, slowly disappears'coni pletelyand afiter three hours the reaction is terminated and after stopping the stlrrerthe d'eca-sodiuni anthraceiie deposits as a sandy powder of bluish-black color under the. clear and colorless l'i'qhi'd. For the analysis;- about 7 0.5 to 1 25' ml. are ut into a small flask without exposin to contact 'with air. I Accurate weighing is useless because the quantity of sodium obtained during the ex ert ment is determined afterwards'by tit-ration with 'nj/l tl H 804- The flaskis closed with a dotible-borediruhber stopper. One of the bores serves to connect the'small flask with a buret filled with water, "the otherone dor connecting with the upper part of ajBuntie bu-ret filled With water the lower part-of Whi'ch isconne'cted with a level vessel From-the buret "about 5 mllof waten are allowed to pass into the small flask, the latter agitatedt the hydrogen. devlopedxis" brought into the Bunte bunt by lowering the level vessel, this operation is repeated if needed until no more hydrogen is found to develop and finally the flask is filled completely with water. Then the Bunte buret is closed and as usual the volume of gas obtained is determined, from which the cubit centimetres of water are deducted which have been employed e for the decomposition of the sodium compound and for i filling the flask. Now the procedure of usual titration] it is possible ther (b 49.65 cu. cm. of n/lO H SO =55.66 cu. cm. of
g. Hence the ratio b :a is equal to 1:0.78 or 10 mol:7.8 mol.
The ratio b ra is therefore equal to 1:0.77 or 10 mol:7.7 mol.
This corresponds for both analyses with good approximation to the value of 10 moles to 8 moles.
Example 2 Into 150 g. of paraffin oil free from water and in a nitrogen atmosphere there are introduced 10.3 g. of comminuted sodium and 19.9 g. of anthracene. The mixture is stirred for four hours at normal temperature, 0.1 g. of tetra-sodium anthracene is added and the mass is heated for three hours up to 110 C. In most cases already in the cold or at the beginning of heating, the suspension becomes dark-colored. After stopping the stirrer, the tetra-sodium anthracene formed separates from the clear and colorless liquid. The analysis (carried out as described in Example 1) give the following data:
(I) Hydrogen developed by means of decomposition and collected above water, reduced to normal pressure and at C.;
(11 4.46 cu. cm.
(a 6.25 cu. cm.
(H) Titration with 12/10 sulfuric acid:
(b 9.15 cu. cm. of 12/10 H SO =10.25 cu. cm. of
(b 10.05 cu. cm. of n/ H SO =12.4 cu. cm. of
The ratio bza are equal to 1:0.44 and 1:05 respectively, which corresponds approximately to the ratio of 4 molecules to 2 molecules.
Example 3 To 200 g. of anhydrous xylene in nitrogen atmosphere there are added 15.2 g. of finely comminuted sodium and 20 g. of stilbene. The mixture is stirred for 12 hours at normal temperature and in nitrogen atmosphere, 0.1 to 0.2 g. of di-sodium stilbene are added and under stirring the mass is heated for 8 hours to 100 C. The suspension becomes dark-colored at once and after stopping the stirrer the hexa-sodium stilbene separates in the shape of a brown-black colored powder. The analysis of two samples of the substance, carried out as described in Example 1, give the following values:
(I) Hydrogen developed by means of decomposition and collected above water, reduced to normal conditions:
(a 14.84 cu. cm.
(a,) 22.4 cu. cm.
(H) Titration with n/ 10 H 80 (b 17.55 cu. cm. of n/lO H SO 19.66 cu. cm. Of Hg.
(b;;) 25.9 cu. cm. of n/ 10 H;SO. ,=29.0 cu. of H The ratio b :a is equal to 1:0.77 and the ratio [1 x1 is equal to 1:075; this corresponds to a molecular ratio of 6245.
Example 4 To 150 g. of anhydrous xylene in nitrogen atmosphere there are added 7 g. of comminuted sodium and 18.05 of anthracene. The mixture is treated as described in the preceding examples and a product is obtained the analytical values whereof, as indicated here below, correspond about to those of tri-sodium anthracene. During some experiments however it is found that the anthracene added has not reacted completely. If allowing to rest, sometimes there deposits under the clear liquid also some nontransformed anthracene. It may be that a tri-sodium anthracene itself does not exist and that a mixture is obtained of disodium anthracene with other sodium anthracenes which contain more than two atoms of sodium, such as for instance tetra-sodium or hexa-sodium anthracene. It is also possible that during certain experiments made for the production of di-sodium anthracene there are obtained compounds containing more than two atoms of sodilnn, besides the anthracene not transformed. The analysis of the substance obtained during the experiment described hereinbefore has given the following results:
(I) Hydrogen obtained by means of decomposition with water, reduced to normal conditions:
(a 7.1 cu. cm.
(a 9.8 cu. cm.
(II) Titration with n/ 10 H ([2 22.63 cu. cm, of n/10 H SO =25.3 cu. cm. of H (12 29.47 cu. cm. of 12/10 H SO =33.0 cu. cm. of H The ratio of bza are 3.56:1 and 3.33:1, which corresponds approximately to the ratio of 3 molecules to 1 molecule.
We claim:
1. A process of forming an alkali-metal compound of a normally solid polynuclear aromatic hydrocarbon containing 2-10 atoms alkali-metal comprising stirring an alkali-metal with said aromatic hydrocarbon for at least about two hours in an inert anhydrous liquid hydrocarbon at atmospheric temperature under a non-oxidizing atmosphere and then heating to about C. to about C. with stirring until a dark precipitate forms.
2. A process according to claim 1, wherein the aromatic compound is anthracene.
3. A process according to claim 1, wherein the aromatic compound is stilbene.
4. A process according to claim 1, wherein the aromatic compound is phenanthrene.
5. A process according to claim 1, wherein the aromatic compound is diphenyl butadine.
6. A process according to claim 1, wherein the liquid hydrocarbon is a benzene homologue.
7. A process according to claim 1, wherein the liquid hydrocarbon is paraffin oil.
References Cited in the file of this patent UNITED STATES PATENTS 2,183,847 Scott Dec. 19, 1939 2,194,450 Scott et al. Mar. 19, 1940 2,816,913 Frank et a1 Dec. 17, 1957 2,839,566 Lctsinger et a1 June 7, 1958 OTHER REFERENCES Wooster et al.: Jour. Amer. Chem. Soc., vol. 53, June 1931, pages 179-187.
Claims (1)
1. A PROCESS OF FORMING AND ALKALI-METAL COMPOUND OF A NORMALLY SOLID POLYNUCLEAR AROMATID HYDROCARBON CONTAINING 2-10 ATOMS ALKALI-METAL COMPRISING STIRRING AN ALKALI-METAL WITH SAID AROMATIC HYDROCARBON FOR AT LEAST ABOUT TWO HOURS IN AN INERT ANHYDROUS LIQUID HYDROCARBON AT ATMOSPHERIC TEMPERATURE UNDER A NON-OXIDIZING ATOMSPHERE AND THEN HEATING TO ABOUT 100*C. TO ABOUT 110*C. WITH STIRRING UNTIL A DARK PRECIPITATE FORMS.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT840814X | 1956-03-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2948762A true US2948762A (en) | 1960-08-09 |
Family
ID=11323953
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US646553A Expired - Lifetime US2948762A (en) | 1956-03-23 | 1957-03-18 | Process for preparing alkaline metals having high reactive power |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US2948762A (en) |
| DE (1) | DE1177156B (en) |
| FR (1) | FR1169904A (en) |
| GB (1) | GB840814A (en) |
| NL (1) | NL102713C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3452112A (en) * | 1963-12-27 | 1969-06-24 | Lithium Corp | Preparation of solutions of lithiumhydrocarbon compounds |
| US3983182A (en) * | 1972-09-05 | 1976-09-28 | Massachusetts Institute Of Technology | Alkali metal organic compounds and their method of preparation |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2183847A (en) * | 1935-11-13 | 1939-12-19 | Du Pont | Process of reacting alkali metals with aromatic hydrocarbons |
| US2194450A (en) * | 1934-07-25 | 1940-03-19 | Du Pont | Dimer of 1,4-dihydronaphthalene |
| US2816913A (en) * | 1953-11-25 | 1957-12-17 | Nat Distillers Chem Corp | Preparation of substituted acids |
| US2839566A (en) * | 1955-06-27 | 1958-06-17 | Callery Chemical Co | Preparation of heterocyclic organoboron compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE292310C (en) * |
-
0
- NL NL102713D patent/NL102713C/xx active
-
1956
- 1956-09-25 DE DEP17070A patent/DE1177156B/en active Pending
-
1957
- 1957-03-01 GB GB6965/57A patent/GB840814A/en not_active Expired
- 1957-03-18 US US646553A patent/US2948762A/en not_active Expired - Lifetime
- 1957-03-21 FR FR1169904D patent/FR1169904A/en not_active Expired
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2194450A (en) * | 1934-07-25 | 1940-03-19 | Du Pont | Dimer of 1,4-dihydronaphthalene |
| US2183847A (en) * | 1935-11-13 | 1939-12-19 | Du Pont | Process of reacting alkali metals with aromatic hydrocarbons |
| US2816913A (en) * | 1953-11-25 | 1957-12-17 | Nat Distillers Chem Corp | Preparation of substituted acids |
| US2839566A (en) * | 1955-06-27 | 1958-06-17 | Callery Chemical Co | Preparation of heterocyclic organoboron compounds |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3452112A (en) * | 1963-12-27 | 1969-06-24 | Lithium Corp | Preparation of solutions of lithiumhydrocarbon compounds |
| US3983182A (en) * | 1972-09-05 | 1976-09-28 | Massachusetts Institute Of Technology | Alkali metal organic compounds and their method of preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1177156B (en) | 1964-09-03 |
| GB840814A (en) | 1960-07-13 |
| NL102713C (en) | |
| FR1169904A (en) | 1959-01-07 |
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