GB929656A - Production of esters of alkylboronic acids and dialkylborinic acids - Google Patents
Production of esters of alkylboronic acids and dialkylborinic acidsInfo
- Publication number
- GB929656A GB929656A GB3626461A GB3626461A GB929656A GB 929656 A GB929656 A GB 929656A GB 3626461 A GB3626461 A GB 3626461A GB 3626461 A GB3626461 A GB 3626461A GB 929656 A GB929656 A GB 929656A
- Authority
- GB
- United Kingdom
- Prior art keywords
- esters
- ester
- olefines
- acids
- acid esters
- 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
Links
- 150000002148 esters Chemical class 0.000 title abstract 10
- 239000002253 acid Substances 0.000 title abstract 5
- 150000007513 acids Chemical class 0.000 title abstract 3
- 238000009835 boiling Methods 0.000 abstract 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- 150000001298 alcohols Chemical class 0.000 abstract 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 239000004327 boric acid Substances 0.000 abstract 2
- -1 boric acid ester Chemical class 0.000 abstract 2
- UYANAUSDHIFLFQ-UHFFFAOYSA-N borinic acid Chemical class OB UYANAUSDHIFLFQ-UHFFFAOYSA-N 0.000 abstract 2
- 229910052796 boron Inorganic materials 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 150000001336 alkenes Chemical class 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000004171 alkoxy aryl group Chemical group 0.000 abstract 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 abstract 1
- 150000005215 alkyl ethers Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 150000001414 amino alcohols Chemical class 0.000 abstract 1
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 1
- 125000005001 aminoaryl group Chemical group 0.000 abstract 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 abstract 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 238000000354 decomposition reaction Methods 0.000 abstract 1
- OKVJWADVFPXWQD-UHFFFAOYSA-N difluoroborinic acid Chemical class OB(F)F OKVJWADVFPXWQD-UHFFFAOYSA-N 0.000 abstract 1
- VNWHJJCHHGPAEO-UHFFFAOYSA-N fluoroboronic acid Chemical class OB(O)F VNWHJJCHHGPAEO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
-
- 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
- C07F5/025—Boronic and borinic acid compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
Esters of boronic and borinic acids having the formula RnB(OR1)3-n, wherein R represents an alkyl radical having at least two carbon atoms which may be substituted by aryl groups or halogen atoms, n is 1 or 2, and R1 represents alkyl, cycloalkyl, alkoxyalkyl, aminoalkyl, alkylaminoalkyl, aryl, alkoxyaryl, aminoaryl or alkylaminoaryl or 2R1 represents alkylene when n is 1, are made by reacting an ester of a halogeno-boric acid having the formula XnB(OR1)3-n wherein X means a halogen, n and R1 are as above, with an olefin and an alkali metal or alkaline earth metal borohydride and recovering the ester formed. The olefines are those derived from radical R by splitting off a hydrogen atom and include olefines of the ethylene series, halo-olefines and arylolefines. Monofluoroboronic acid esters and difluoroborinic acid esters are suitable starting materials. Temperatures between -20 DEG C. and the decomposition point of the reactants or the boiling point of any solvent may be used, the optimum temperature lying between 30 and 100 DEG C. The haloboric acid esters may be made in situ by introducing boron trihalide into a mixture of borohydride and boric acid ester in a solvent. Thus the boronic or borinic acid esters may be made by reacting akali metal or alkaline earth metal borohydrides with boric acid esters B(OR1)3, alkyl ether addition compounds of boron trihalide and olefines. Esters of alkylboronic acid or dialkylborinic acids with alkanols, such as methanol, ethanol, propanol, butanol or amyl alcohol, can be converted into esters of higher boiling alcohols, alkoxyalkyl alcohols or aminoalcohols by heating the esters of said alkanols with said higher-boiling alcohols, if necessary in a vacuum, to temperatures between the boiling point of the lower alcohol and that of the higher boiling alcohol, until the alkanol bound in the ester is completely distilled off and recovering the desired ester.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF29686A DE1094747B (en) | 1959-10-23 | 1959-10-23 | Process for the preparation of esters of alkyl boric acids |
| DEF31573A DE1121613B (en) | 1959-10-23 | 1960-07-02 | Process for the preparation of esters of alkyl boric acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB929656A true GB929656A (en) | 1963-06-26 |
Family
ID=25974462
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3626461A Expired GB929656A (en) | 1959-10-23 | 1960-10-21 | Production of esters of alkylboronic acids and dialkylborinic acids |
Country Status (2)
| Country | Link |
|---|---|
| DE (2) | DE1094747B (en) |
| GB (1) | GB929656A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4795821A (en) * | 1986-08-29 | 1989-01-03 | Aldrich-Boranes, Inc. | Optically active borinic esters and ketones |
| CN112746289A (en) * | 2021-01-21 | 2021-05-04 | 合肥工业大学 | Synthesis method of alkyl borate compound |
-
1959
- 1959-10-23 DE DEF29686A patent/DE1094747B/en active Pending
-
1960
- 1960-07-02 DE DEF31573A patent/DE1121613B/en active Pending
- 1960-10-21 GB GB3626461A patent/GB929656A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4795821A (en) * | 1986-08-29 | 1989-01-03 | Aldrich-Boranes, Inc. | Optically active borinic esters and ketones |
| CN112746289A (en) * | 2021-01-21 | 2021-05-04 | 合肥工业大学 | Synthesis method of alkyl borate compound |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1121613B (en) | 1962-01-11 |
| DE1094747B (en) | 1960-12-15 |
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