GB722538A - Cyclic esters of boric acid - Google Patents
Cyclic esters of boric acidInfo
- Publication number
- GB722538A GB722538A GB458852A GB458852A GB722538A GB 722538 A GB722538 A GB 722538A GB 458852 A GB458852 A GB 458852A GB 458852 A GB458852 A GB 458852A GB 722538 A GB722538 A GB 722538A
- Authority
- GB
- United Kingdom
- Prior art keywords
- diol
- borate
- alcohol
- ethyl
- 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
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 title abstract 5
- 239000004327 boric acid Substances 0.000 title abstract 5
- 125000004122 cyclic group Chemical group 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 9
- 150000002148 esters Chemical class 0.000 abstract 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 6
- 150000002009 diols Chemical class 0.000 abstract 6
- 235000019441 ethanol Nutrition 0.000 abstract 6
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 abstract 4
- 230000032050 esterification Effects 0.000 abstract 4
- 238000005886 esterification reaction Methods 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- WWYCCHFWPNKQPM-UHFFFAOYSA-N boric acid;2-methylpentane-2,4-diol Chemical compound OB(O)O.CC(O)CC(C)(C)O WWYCCHFWPNKQPM-UHFFFAOYSA-N 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 3
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- MHNYUMPVQKTSLK-UHFFFAOYSA-N 2,4-dimethylhexane-2,4-diol Chemical compound CCC(C)(O)CC(C)(C)O MHNYUMPVQKTSLK-UHFFFAOYSA-N 0.000 abstract 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 abstract 2
- JHWQMXKQJVAWKI-UHFFFAOYSA-N 3-phenylpropane-1,2-diol Chemical compound OCC(O)CC1=CC=CC=C1 JHWQMXKQJVAWKI-UHFFFAOYSA-N 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 abstract 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 150000005690 diesters Chemical class 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 abstract 2
- 238000010992 reflux Methods 0.000 abstract 2
- 150000005691 triesters Chemical class 0.000 abstract 2
- ZWVMLYRJXORSEP-LURJTMIESA-N (2s)-hexane-1,2,6-triol Chemical compound OCCCC[C@H](O)CO ZWVMLYRJXORSEP-LURJTMIESA-N 0.000 abstract 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 abstract 1
- WFSOUGZEVPHHSM-UHFFFAOYSA-N 1-phenylbutane-1,2-diol Chemical compound CCC(O)C(O)C1=CC=CC=C1 WFSOUGZEVPHHSM-UHFFFAOYSA-N 0.000 abstract 1
- QTYZWFQTOYXFBL-UHFFFAOYSA-N 1-phenylbutane-1,3-diol Chemical compound CC(O)CC(O)C1=CC=CC=C1 QTYZWFQTOYXFBL-UHFFFAOYSA-N 0.000 abstract 1
- MZQZXSHFWDHNOW-UHFFFAOYSA-N 1-phenylpropane-1,2-diol Chemical compound CC(O)C(O)C1=CC=CC=C1 MZQZXSHFWDHNOW-UHFFFAOYSA-N 0.000 abstract 1
- BAYAKMPRFGNNFW-UHFFFAOYSA-N 2,4-dimethylpentan-3-ol Chemical compound CC(C)C(O)C(C)C BAYAKMPRFGNNFW-UHFFFAOYSA-N 0.000 abstract 1
- DBTGFWMBFZBBEF-UHFFFAOYSA-N 2,4-dimethylpentane-2,4-diol Chemical compound CC(C)(O)CC(C)(C)O DBTGFWMBFZBBEF-UHFFFAOYSA-N 0.000 abstract 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 abstract 1
- LNCZPZFNQQFXPT-UHFFFAOYSA-N 2-phenyl-1,2-propanediol Chemical compound OCC(O)(C)C1=CC=CC=C1 LNCZPZFNQQFXPT-UHFFFAOYSA-N 0.000 abstract 1
- SNCPNGLMZQUXGY-UHFFFAOYSA-N 2-phenylbutane-1,2-diol Chemical compound CCC(O)(CO)C1=CC=CC=C1 SNCPNGLMZQUXGY-UHFFFAOYSA-N 0.000 abstract 1
- BQNJVHGCZBNKBG-UHFFFAOYSA-N 3-phenylbutane-1,3-diol Chemical compound OCCC(O)(C)C1=CC=CC=C1 BQNJVHGCZBNKBG-UHFFFAOYSA-N 0.000 abstract 1
- NYHOBXZEBFBAHD-UHFFFAOYSA-N 4-phenylbutane-1,2-diol Chemical compound OCC(O)CCC1=CC=CC=C1 NYHOBXZEBFBAHD-UHFFFAOYSA-N 0.000 abstract 1
- NJFWVADANWBCLW-UHFFFAOYSA-N B(O)(O)O.C(C)CC(CC(C)O)O Chemical compound B(O)(O)O.C(C)CC(CC(C)O)O NJFWVADANWBCLW-UHFFFAOYSA-N 0.000 abstract 1
- BJUMBVWDMMXCQJ-UHFFFAOYSA-N B(O)(O)O.C(C)CC(O)(C)C(C)(C)O Chemical compound B(O)(O)O.C(C)CC(O)(C)C(C)(C)O BJUMBVWDMMXCQJ-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- -1 alkane diols Chemical class 0.000 abstract 1
- 150000007860 aryl ester derivatives Chemical class 0.000 abstract 1
- 238000010533 azeotropic distillation Methods 0.000 abstract 1
- ZPKQJIWCBWCCSU-UHFFFAOYSA-N boric acid 2,4-dimethylheptane-2,4-diol Chemical compound B(O)(O)O.C(C)CC(CC(C)(O)C)(O)C ZPKQJIWCBWCCSU-UHFFFAOYSA-N 0.000 abstract 1
- VRCWBBPZGPYUGV-UHFFFAOYSA-N boric acid 3,5-dimethyloctane-3,5-diol Chemical compound B(O)(O)O.C(C)CC(CC(CC)(O)C)(O)C VRCWBBPZGPYUGV-UHFFFAOYSA-N 0.000 abstract 1
- KXANELPMVRFXAE-UHFFFAOYSA-N boric acid 4-methylheptane-2,4-diol Chemical compound B(O)(O)O.C(C)CC(CC(C)O)(O)C KXANELPMVRFXAE-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 238000002485 combustion reaction Methods 0.000 abstract 1
- 229930003836 cresol Natural products 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 239000000446 fuel Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- AEIJTFQOBWATKX-UHFFFAOYSA-N octane-1,2-diol Chemical compound CCCCCCC(O)CO AEIJTFQOBWATKX-UHFFFAOYSA-N 0.000 abstract 1
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 abstract 1
- GTCCGKPBSJZVRZ-UHFFFAOYSA-N pentane-2,4-diol Chemical compound CC(O)CC(C)O GTCCGKPBSJZVRZ-UHFFFAOYSA-N 0.000 abstract 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 abstract 1
- 229940067107 phenylethyl alcohol Drugs 0.000 abstract 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical class CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 abstract 1
- 238000001577 simple distillation Methods 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
- BOOITXALNJLNMB-UHFFFAOYSA-N tricyclohexyl borate Chemical class C1CCCCC1OB(OC1CCCCC1)OC1CCCCC1 BOOITXALNJLNMB-UHFFFAOYSA-N 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 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
- C07F5/04—Esters of boric acids
-
- 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)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention comprises as new compounds cyclic esters of boric acid of the general formula <FORM:0722538/IV (b)/1> wherein n represents 0 or 1, R represents a hydrogen atom or an alkyl, aralkyl, cycloalkyl, or aryl group and R1 is an alkyl, aralkyl, cycloalkyl or aryl group. The esters may be prepared by reacting, at elevated temperature the appropriate diol having the hydroxy groups on adjacent carbon atoms or on carbon atoms separated by one carbon atom with an alkyl, aralkyl, cycloalkyl or aryl ester of boric acid. The preferred diols are the alkane diols such as the propane diols, butane-1,2(1,3- or 2,3-)-diol, pentane 1,2-diol and the corresponding 2,3- and 2,4-diols, hexane-1,2(2,3-, 2,4- or 3,4-)-diol, heptane 1,2- or 3,4-diol, octane-1,2-diol, and the corresponding 4,5-diol, 2,4-dimethylhexane-2,4-diol, 2,4 - dimethylpentane - 2,4 - diol, pinacol and 2-methylpentane-2,4-diol. Specified aromatic substituted diols which may be employed are 1-, 2- or 3-phenylpropane-1,2-diol, 1-, 2- or 4-phenylbutane-1,2-diol and 1- or 3-phenylbutane-1,3-diol. The boric ester used is preferably a triester but mono- or di-esters may also be used. If a triester or diester is used it should preferably be derived from an alcohol or phenol capable of being removed readily from the reaction as it is formed, e.g. by simple or azeotropic distillation. Specified esters are trimethyl, triethyl, tributyl, triphenyl and tricyclohexyl borates. An esterification catalyst, e.g. sulphuric, p-toluene sulphonic acid or hydrogen chloride may be employed if desired. An inert liquid diluent may also be present. Another method of preparing the esters comprises esterifying with the appropriate alcohol or phenol, an acid ester of the general formula p <FORM:0722538/IV (b)/2> wherein R and n are as defined above. These acid esters may be made by esterification of boric acid with the appropriate diol, e.g. one of the diols specified above. The alcohol or phenol may be an alkanol such as methanol, ethanol, a propanol, butanol, pentanol or homologue thereof, benzyl alcohol, phenylethyl alcohol, phenol or a cresol of xylenol or homologue thereof. If desired an esterification catalyst may be present. The esterification may be conducted by refluxing a mixture of the acid ester and the alcohol or phenol diluted with an inert solvent such as benzene, toluene or xylene under such conditions that water is removed from the system. In examples: (1) ethyl 2,4-dimethylhexane-2,4-diol borate is obtained by distilling azeotropically a mixture of 2,4-dimethylhexane-2,4-diol and triethyl borate dissolved in benzene until the liberation of ethyl alcohol is complete; (2) ethyl pentane-2,4-diol borate is obtained from pentane-2,4-diol and triethyl borate by a similar procedure as in (1); (3), (4) and (5) ethyl-2,4-dimethylpentane-2,4-diol borate, ethyl pinacol borate and ethyl 2-methyl-pentane-2,4-diol borate respectively are obtained in a similar manner from the corresponding diol and triethyl borate; (c) 2-methylpentane-2,4-diol borate is refluxed with diisopropylcarbinol in the presence of toluene until water evolution is complete to yield diisopropyl-carbinyl 2-methylpentane-2,4-diol borate. The 2-methylpentane-2,4-diol borate is prepared by refluxing 2-methylpentane-2,4-diol with boric acid and benzene until no more water is evolved. The ester products may be used as additives in liquid fuels for internal combustion engines as described in Specification 722,537, [Group III].
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB458852A GB722538A (en) | 1952-02-21 | 1952-02-21 | Cyclic esters of boric acid |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB458852A GB722538A (en) | 1952-02-21 | 1952-02-21 | Cyclic esters of boric acid |
Publications (1)
Publication Number | Publication Date |
---|---|
GB722538A true GB722538A (en) | 1955-01-26 |
Family
ID=9779994
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB458852A Expired GB722538A (en) | 1952-02-21 | 1952-02-21 | Cyclic esters of boric acid |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB722538A (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1082453B (en) * | 1956-04-09 | 1960-05-25 | Ethyl Corp | Fuel for jet engines |
US3189637A (en) * | 1962-05-24 | 1965-06-15 | United States Borax Chem | Cycloalkenyl glycol boric acid esters |
US4104374A (en) | 1976-05-18 | 1978-08-01 | Basf Aktiengesellschaft | Wood preservative |
US4742044A (en) * | 1987-08-19 | 1988-05-03 | International Flavors & Fragrances Inc. | Aralkoxy, alkoxy, alkadienyloxy and alkenyloxy-1,3,2-dioxaborinane derivatives and uses thereof in augmenting or enhancing the aroma of perfume compositions, perfumed articles and perfumed polymers |
CN114517407A (en) * | 2022-02-25 | 2022-05-20 | 江苏恒力化纤股份有限公司 | Preparation method of cyclic borate flame retardant and flame-retardant polyester fiber product thereof |
-
1952
- 1952-02-21 GB GB458852A patent/GB722538A/en not_active Expired
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1082453B (en) * | 1956-04-09 | 1960-05-25 | Ethyl Corp | Fuel for jet engines |
US3189637A (en) * | 1962-05-24 | 1965-06-15 | United States Borax Chem | Cycloalkenyl glycol boric acid esters |
US4104374A (en) | 1976-05-18 | 1978-08-01 | Basf Aktiengesellschaft | Wood preservative |
US4742044A (en) * | 1987-08-19 | 1988-05-03 | International Flavors & Fragrances Inc. | Aralkoxy, alkoxy, alkadienyloxy and alkenyloxy-1,3,2-dioxaborinane derivatives and uses thereof in augmenting or enhancing the aroma of perfume compositions, perfumed articles and perfumed polymers |
CN114517407A (en) * | 2022-02-25 | 2022-05-20 | 江苏恒力化纤股份有限公司 | Preparation method of cyclic borate flame retardant and flame-retardant polyester fiber product thereof |
CN114517407B (en) * | 2022-02-25 | 2023-08-29 | 江苏恒力化纤股份有限公司 | Cyclic borate flame retardant and preparation method of flame-retardant polyester fiber product thereof |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US2839564A (en) | Cyclic esters of boric acid | |
US2802856A (en) | Methods of preparing tri-esters of thiophosphoric acids | |
US2907787A (en) | Preparation of phosphono-thiono esters of 2-hydroxyethyl sulfides | |
GB722538A (en) | Cyclic esters of boric acid | |
US2335953A (en) | Diesel fuel | |
US2476052A (en) | Ester exchange reaction | |
US2441183A (en) | Hexahydrobenzyl ester | |
US3013016A (en) | Trialkylamine boranes and their preparation | |
US2940839A (en) | Fuel composition | |
US3021206A (en) | Gasoline containing dialkanolamine boronic acid bis-esters | |
US2898352A (en) | Ester type surface active agents | |
US3253013A (en) | Esters of metaboric acid and process for the preparation thereof | |
US2907783A (en) | Carbon functional organo-siloxane dibasic acid esters | |
US3259671A (en) | Process for preparing organic phosphinic acids and esters from olefins and products produced thereby | |
US2939876A (en) | Preparation of acid anhydrides | |
US3271436A (en) | Process for the production of heterocyclic boron compounds | |
US3081332A (en) | Process for reacting trialkyl phosphites with disulfides to produce phosphorothiolate triesters | |
US3796734A (en) | Preparation of omega-nitroesters by thermal cleavage and reaction of cyclic alpha-nitroketones with alcohols | |
US2938930A (en) | Preparation of chlormethylated alkyl aromatic hydrocarbons | |
US3206493A (en) | Preparation of o, o, s-triesters of monothiophosphoric acid | |
GB742949A (en) | Improvements in and relating to the condensation of di-alkyl succinates | |
Fields | Thiophosphoryl Derivatives of the Adducts from Hexachlorocyclopentadiene and Unsaturated Alcohols | |
US3045037A (en) | Process for making phosphorus ester lube oil additive | |
US1741877A (en) | New process of preparing phenyl-oxalyl acetic-acid alkyl esters | |
GB929656A (en) | Production of esters of alkylboronic acids and dialkylborinic acids |