DE1052986B - Process for the preparation of organoboron compounds - Google Patents
Process for the preparation of organoboron compoundsInfo
- Publication number
- DE1052986B DE1052986B DEK31389D DEK0031389D DE1052986B DE 1052986 B DE1052986 B DE 1052986B DE K31389 D DEK31389 D DE K31389D DE K0031389 D DEK0031389 D DE K0031389D DE 1052986 B DE1052986 B DE 1052986B
- Authority
- DE
- Germany
- Prior art keywords
- boron
- weight
- parts
- compounds
- hydride
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title description 3
- 239000003513 alkali Substances 0.000 claims description 12
- 229910052796 boron Inorganic materials 0.000 claims description 12
- 150000004678 hydrides Chemical class 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 9
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 6
- 230000003213 activating effect Effects 0.000 claims description 4
- 150000002894 organic compounds Chemical class 0.000 claims description 4
- 239000000375 suspending agent Substances 0.000 claims description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052733 gallium Inorganic materials 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- -1 boron halides Chemical class 0.000 description 11
- 150000001336 alkenes Chemical class 0.000 description 7
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical group [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 5
- 239000012190 activator Substances 0.000 description 4
- 229910000085 borane Inorganic materials 0.000 description 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 4
- 229910015844 BCl3 Inorganic materials 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- PQZTVWVYCLIIJY-UHFFFAOYSA-N diethyl(propyl)amine Chemical compound CCCN(CC)CC PQZTVWVYCLIIJY-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910001623 magnesium bromide Inorganic materials 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/30—Organic compounds compounds not mentioned before (complexes)
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- B01J31/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
- B01J31/146—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron of boron
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von b oro rganis chen Verbindungen Es sind Verfahren zur Herstellung von bororganischen Verbindungen bekannt, die auf einer Umsetzung von Borhalogeniden mit Grignardverbindungen, beispielsweise Alkylmagnesiumbromid, oder mit alumininmorganischen Verbindungen beruhen, oder welche durch die Anlagerung von Olefinen an Diboran gekennzeichnet sind. Diese bekannten Verfahren haben den Nachteil, entweder zu kostspielig oder zu schwierig in der Ausführung zu sein. Process for the preparation of organic compounds There are Process for the preparation of organoboron compounds known on a Reaction of boron halides with Grignard compounds, for example alkyl magnesium bromide, or with aluminine-organic compounds, or which are based on the addition are characterized by olefins on diborane. These known methods have the Disadvantage of being either too expensive or too difficult to execute.
Es wurde nun ein einfaches und billiges Verfahren zur Herstellung von bororganischen Verbindungen gefunden, welches aus der Umsetzung von Bothalogeniden mit Alkalihydriden und Olefinen in Gegenwart eines organischen Am ins und einer Alkalihydrid aktivierenden Verbindung besteht. It now became a simple and inexpensive method of manufacture of organoboron compounds found, which results from the conversion of bothalides with alkali hydrides and olefins in the presence of an organic amine and a Alkali hydride activating compound exists.
Unter Borhalogeniden werden allgemein solche Verbindungen verstanden, die mindestens ein Halogenatom am Boratom gebunden enthalten, wie beispielsweise Bortrichlorid, DibortetrachLorid oder auch Alkvlborchloride und Alkoxyborchlolride. Das vorteilhafteste Alkalihydrid ist das Natriumbydrid, welches einfach und billig herzustellen und bequem in der Anwendung ist. Aber auch Kaliumhydrid reagiert nach dem erfindungsgemäßen Verfahren. Als Olefine werden normale, verzweigte oder auch suhstituierte, eine Doppelbindung enthaltende Kohlenwasserstoffe angewandt, deren Auswahl sich nach den vorgesehenen, ein Wasserstoffatom mchr tragenden, gesättigten Kohlenwas serstoffresten am Boratom richtet. Boron halides are generally understood to mean those compounds which contain at least one halogen atom bonded to the boron atom, such as, for example Boron trichloride, dibortetrachloride or also alkoboron chlorides and alkoxyborochlorides. The most advantageous alkali hydride is sodium hydride, which is simple and cheap and is convenient to use. But potassium hydride also reacts the method according to the invention. As olefins are normal, branched or also substituted hydrocarbons containing a double bond are used, their Selection is based on the intended saturated, hydrogen atom-bearing Hydrogen radicals on the boron atom.
Die Umsetzung wird durch die folgende Gleichung dargestellt: BCl3 + 3NaH + 3C2H4 ~~~ B(C2H5)3 + 3NaCl. (1) Die Reaktion tritt so einfach jedoch nicht ein, da das in einem gegen die Reaktionsteilnehmer indifferenten Suspensionsmittel eingebrachte unlösliche Natriumhydrid zunächst in eine aktivierte, lösliche Form übergeführt werden muß. Für diesen Zweck eignen sich besonders die organischen Verbindungen einiger Elemente der III. Gruppe des Periodischen Systems, insbesondere die Alkyle, Alkylhydnde und Alkoholate des Bors, Aluminiums und Galliums. Von diesen Verbindungen sind im allgemeinen schon 0,1 0/o, bezlogen auf das suspendierte Alkalihydrid, ausreichend; vorzugsweise werden jedoch 5 bis 30ozon eingesetzt. Werden andere metallorganische Verbindungen verwendet, so setzen sich diese meist mit dem verwendeten Borhalogenid zu hororganischen Verbindungen um, so daß im Endeffekt auch mit b4erorganischen Verbindungen als Aktivator gearbeitet wird. The conversion is represented by the following equation: BCl3 + 3NaH + 3C2H4 ~~~ B (C2H5) 3 + 3NaCl. (1) The reaction does not occur that easily, however one, since that in a suspension medium that is indifferent to the reactants Introduced insoluble sodium hydride initially in an activated, soluble form must be transferred. The organic compounds are particularly suitable for this purpose some elements of the III. Group of the periodic table, especially the alkyls, Alkyl hydrates and alcoholates of boron, aluminum and gallium. From these connections 0.1%, based on the suspended alkali hydride, are generally sufficient; however, 5 to 30 ozone are preferably used. Will other organometallic Compounds used, so these usually settle with the boron halide used to organic compounds, so that in the end also with organic compounds Compounds is worked as an activator.
Die Gegenwart eines organischen, vorzugsweise tertiären Amins ist erforderlich, um das bei der Hydrierung des Borhalogenids mit aktiviertem Alkalihydrid entstehende Borin B H3 abzufangen. Besonders geeignet sind tertiäre Amine, wie Trimethylamin, Triäthylamin, Tripopylamin, Diäthylpropylamin, aber auch Dibutylamin, Morpholin und Piperidin. Es ist vorteilhaft, mit etwa 5 bis 20°/o Überschull über die stö,chiometrische Menge zu arbeiten. The presence of an organic, preferably tertiary, amine is required for the hydrogenation of the boron halide with activated alkali hydride intercept resulting borine B H3. Tertiary amines such as trimethylamine, Triethylamine, tripopylamine, diethylpropylamine, but also dibutylamine, morpholine and piperidine. It is advantageous to have about 5 to 20% overshoot over the stoichiometric Amount to work.
Berücksichtigt man bei der Reaktion der Gleichung (1) unter Einbeziehung
des Aktivators fur das Alkalihvdrid und des Borin bindenden Amins das Zwischenprodukt,
so lassen sich die Gleichungen (2) und (3) statt der Gleichung (1) anfühWren:
Selbstverständlich kann man auch die Reaktion auf der Stufe der Boralkylhydride zum Stillstand kommen lassen, wenn weniger Olefin eingeleitet wird, als der für die totale Alkylierung berech,neten Menge entspricht. Dabei ergeben sich auch für die teilweise alkylierten Produkte noch Anlagerungsverbindungen mit dem eingesetzten Amin. Of course, the reaction at the boron alkyl hydride stage can also be used Let come to a standstill if less olefin is introduced than that for the total alkylation corresponds to the calculated amount. This also results for the partially alkylated products still add addition compounds with the used Amine.
Wird die reine Verbindung gewünscht, so kaun diese meist durch Destillation von dem Amin befreit werden. If the pure connection is desired, this can usually be obtained by distillation be freed from the amine.
Es ist zweckmäßig, die Umsetzung in Gegenwart von gegen die Reaktionsteilnehmer indifferenten Lösungs- oder Suspensionsmitteln bei Tetnperaturen bis zu 2200'C duirchzuführen. Zur ReaktionsbesclDleunigung empfiehlt es sich, insbesondere bei der Olefinanlagerung unter leichtem Druck zu rbeiten. Aktion. vator und Amin können im Kreislauf geführt werden. It is appropriate to carry out the reaction in the presence of against the reactants indifferent Solvents or suspending agents at temperatures up to 2200'C. It is particularly recommended to accelerate the reaction to work with the addition of olefins under slight pressure. Action. vator and amine can be circulated.
Das entsprechend der Reaktion der Gleichung (21 entstandene Alkalihalogenid wird zweckmäßigerweise vor der Olefinanlagerung entsprechend Gleichung (3) abgetrennt.The alkali halide formed according to the reaction of equation (21 is expediently separated off in accordance with equation (3) before the addition of olefins.
Die erfindungsgemäß hergestellten bororganischen Verbindungen finden als Katalysatoren in der organischen Chemie, als Treibstoffe oder Zusätze zu Treibstoffen, als Schädlingsbekämpfungsmittel und in der pharmazeutischen Industrie Verwendung. Find the organoboron compounds prepared according to the invention as catalysts in organic chemistry, as fuels or additives to fuels, as a pesticide and in the pharmaceutical industry.
Beispiel 1 Eine Suspension von 50 Gewichtsteilen Natriumhvdrid in 200 Gewichtsteilen eines Mineralöls vom IÇp. 200 bis 2200 C wurde auf 700 C erhitzt und mit 15 Gewichtsteilen Bortriäthyl versetzt. Hierauf wurden 68 Gewichtsteile Triäthylamin zugegeben und unter gutem Rühren in das Gemisch insgesamt 79 Gewichtsteile Bortrichlorid eingeleitet. Example 1 A suspension of 50 parts by weight of sodium hydride in 200 parts by weight of a mineral oil from IÇp. 200 to 2200 C was heated to 700 C. and mixed with 15 parts by weight of boron triethyl. Thereupon were 68 parts by weight Triethylamine was added and a total of 79 parts by weight into the mixture with thorough stirring Boron trichloride initiated.
Dann wurde die Temperatur auf 150 bis 170°C erhöht und Äthylen eingeleitet. Die Aufnahme betrug 48 Gewichtsteile = iiber 90°/o der Theorie. Wurde das erzeugte N-Triäthylborazan vorher im Vakuum abdestilliert und hierauf bei 140 bis 170;0 C Äthylen eingeleitet, so war die Ausbeute an hergestelltem Bortriäthyl noch etwas besser, was auch der Fall ist, wenn bei Temperaturen bis 2000 C unter Druck ge arbeitet wurde. The temperature was then increased to 150 to 170 ° C. and ethylene was passed in. The uptake was 48 parts by weight = over 90% of theory. Was that generated N-triethylborazane was previously distilled off in vacuo and then at 140 to 170.degree Introduced ethylene, the yield of boron triethyl produced was still somewhat better, which is also the case when working under pressure at temperatures up to 2000 C. became.
Beispiel 2 25 Gewichtsteile Natriumhydrid, ssuspendiert in 180 Gewichtsteilen Octan, wurden bei einer Temperatur von 800 C zunächst mit 15 Gewichtsteilen Bortriäthyl, danach mit 35 Gewichtsteilen Triäthylamin versetzt, worauf bei 80 bis 950 C insgesamt 40Gewichtsteile Bortrichlorid eingeleitet wurden. Nach Abzentrifugieren des ausgefallenen Na Cl wurden 90 Géwíchtsteile Cyclohexen zugesetzt, und es wurde 2 Stunden unter Rückfluß gekocht. Nach Abdestillieren des abgespaltenen Bortriäthyls sowie Triäthylamin,s und des als Suspensionsmittel benutzten Octans wurden oG'ewichtsteile Bortricyclohexyl als Rückstand erhalten (über 760/0 der Theorie). Example 2 25 parts by weight of sodium hydride suspended in 180 parts by weight Octane, were initially at a temperature of 800 C with 15 parts by weight of boron triethyl, then mixed with 35 parts by weight of triethylamine, whereupon at 80 to 950 C in total 40 parts by weight of boron trichloride were introduced. After centrifuging off the precipitated Na Cl were 90 parts by weight of cyclohexene were added and it was taken for 2 hours Refluxed. After the split off boron triethyl and triethylamine have been distilled off, s and the octane used as a suspending agent were oW parts by weight of boron tricyclohexyl obtained as a residue (about 760/0 of theory).
Beispiel 3 25 Gewichtsteile Natriumhydrid, suspendiert in 18 Gewichtsteilen Cyclohexen, wurden bei 750 C mit 18 Gewichtsteilen Bortriäthyl und 35 Gewichtsteilen Triäthylamin versetzt. Hierauf wurden 39,5 Gewichtsteile Borchlorid bei einer Temperatur von 75 bis 850 C- eingeleitet. Nach Abkühlen wurde zentrifugiert, und die flüchtigen Anteile wurden unter Normaldruck abdestilliert. Als Rückstand verblieben 40 Gewichtsteile B ortricyclohexyl. Example 3 25 parts by weight of sodium hydride suspended in 18 parts by weight Cyclohexene, were at 750 C with 18 parts by weight of boron triethyl and 35 parts by weight Triethylamine added. Thereupon 39.5 parts by weight of boron chloride were added at one temperature initiated from 75 to 850 C-. After cooling it was centrifuged and the volatile Fractions were distilled off under normal pressure. 40 parts by weight remained as residue Boron tricyclohexyl.
PATENTANSPROCIIE 1. Verfahren zur Herstellung von bororganischen Verbindungen, dadurch gekennzeichnet, daß Borhalogenide mit Alkalihydriden und Olefinen in Gegenwart von organischen Aminen und von Alkalihydrid aktivierenden Verbindungen umgesetzt werden. PATENT APPLICATION 1. Process for the production of organic boron Compounds, characterized in that boron halides with alkali hydrides and olefins in the presence of organic amines and of alkali hydride activating compounds implemented.
Claims (1)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK31389D DE1052986B (en) | 1957-03-13 | 1957-03-13 | Process for the preparation of organoboron compounds |
| GB7998/58A GB835847A (en) | 1957-03-13 | 1958-03-12 | Method of preparing boro-organic compounds |
| DEK42484D DE1151800B (en) | 1957-03-13 | 1960-12-22 | Process for the preparation of organoboron compounds |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK31389D DE1052986B (en) | 1957-03-13 | 1957-03-13 | Process for the preparation of organoboron compounds |
| DEK42484D DE1151800B (en) | 1957-03-13 | 1960-12-22 | Process for the preparation of organoboron compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1052986B true DE1052986B (en) | 1959-03-19 |
Family
ID=33030654
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEK31389D Pending DE1052986B (en) | 1957-03-13 | 1957-03-13 | Process for the preparation of organoboron compounds |
| DEK42484D Pending DE1151800B (en) | 1957-03-13 | 1960-12-22 | Process for the preparation of organoboron compounds |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEK42484D Pending DE1151800B (en) | 1957-03-13 | 1960-12-22 | Process for the preparation of organoboron compounds |
Country Status (2)
| Country | Link |
|---|---|
| DE (2) | DE1052986B (en) |
| GB (1) | GB835847A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1115250B (en) * | 1959-11-13 | 1961-10-19 | Kali Chemie Ag | Process for the preparation of organoboron compounds |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108178770B (en) * | 2017-12-11 | 2020-04-28 | 华南理工大学 | Method for synthesizing α -amino boron compound |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1038019B (en) * | 1957-03-20 | 1958-09-04 | Kali Chemie Ag | Process for the preparation of hydrogen boride compounds |
| FR1222316A (en) * | 1958-04-25 | 1960-06-09 | Purdue Research Foundation | Process for the preparation of organic boron compounds |
-
1957
- 1957-03-13 DE DEK31389D patent/DE1052986B/en active Pending
-
1958
- 1958-03-12 GB GB7998/58A patent/GB835847A/en not_active Expired
-
1960
- 1960-12-22 DE DEK42484D patent/DE1151800B/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1115250B (en) * | 1959-11-13 | 1961-10-19 | Kali Chemie Ag | Process for the preparation of organoboron compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| GB835847A (en) | 1960-05-25 |
| DE1151800B (en) | 1963-07-25 |
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