CH401941A - Verfahren zur Herstellung von Metaborsäureestern und Polyborsäureestern - Google Patents

Verfahren zur Herstellung von Metaborsäureestern und Polyborsäureestern

Info

Publication number: CH401941A
Authority: CH; Switzerland
Prior art keywords: acid ester; catalyst; boron oxide; orthoboric acid; acid esters
Prior art date: 1958-02-12

Application number

CH6945559A

Other languages

German (de)

English (en)

Inventor

Lester Hunter Don

Original Assignee

United States Borax Chem

Priority date (The priority date 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 date listed.)

1958-02-12

Filing date

1959-02-12

Publication date

1965-11-15

1959-01-21 Priority claimed from US788040A external-priority patent/US3099677A/en

1959-02-12 Application filed by United States Borax Chem filed Critical United States Borax Chem

1965-11-15 Publication of CH401941A publication Critical patent/CH401941A/de

Links

150000002148 esters Chemical class 0.000 title claims description 36
238000000034 method Methods 0.000 title claims description 23
239000002253 acid Substances 0.000 title claims description 12
VGTPKLINSHNZRD-UHFFFAOYSA-N oxoborinic acid Chemical class OB=O VGTPKLINSHNZRD-UHFFFAOYSA-N 0.000 title claims description 6
238000002360 preparation method Methods 0.000 title claims description 6
-1 orthoboric acid ester Chemical class 0.000 claims description 40
JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 claims description 29
229910052810 boron oxide Inorganic materials 0.000 claims description 28
238000006243 chemical reaction Methods 0.000 claims description 25
239000003054 catalyst Substances 0.000 claims description 24
229960002645 boric acid Drugs 0.000 claims description 20
235000010338 boric acid Nutrition 0.000 claims description 20
239000011541 reaction mixture Substances 0.000 claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 9
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 7
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
150000001875 compounds Chemical class 0.000 claims description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 5
150000003333 secondary alcohols Chemical class 0.000 claims description 3
150000003509 tertiary alcohols Chemical class 0.000 claims description 3
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 2
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 2
HEBKCHPVOIAQTA-QWWZWVQMSA-N D-arabinitol Chemical compound OC[C@@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-QWWZWVQMSA-N 0.000 claims description 2
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 2
WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims description 2
239000004386 Erythritol Substances 0.000 claims description 2
UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 claims description 2
RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 2
239000005715 Fructose Substances 0.000 claims description 2
229930091371 Fructose Natural products 0.000 claims description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 2
229930195725 Mannitol Natural products 0.000 claims description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 2
UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 claims description 2
235000019414 erythritol Nutrition 0.000 claims description 2
229940009714 erythritol Drugs 0.000 claims description 2
239000008103 glucose Substances 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
239000000594 mannitol Substances 0.000 claims description 2
235000010355 mannitol Nutrition 0.000 claims description 2
HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 2
150000002894 organic compounds Chemical class 0.000 claims description 2
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 2
150000002989 phenols Chemical class 0.000 claims description 2
125000000075 primary alcohol group Chemical group 0.000 claims description 2
239000000600 sorbitol Substances 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 3
238000010438 heat treatment Methods 0.000 claims 2
125000003158 alcohol group Chemical group 0.000 claims 1
230000007062 hydrolysis Effects 0.000 claims 1
238000006460 hydrolysis reaction Methods 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
229910052796 boron Inorganic materials 0.000 description 20
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 17
239000007788 liquid Substances 0.000 description 11
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
238000003756 stirring Methods 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 6
239000000203 mixture Substances 0.000 description 6
239000002245 particle Substances 0.000 description 6
239000007795 chemical reaction product Substances 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 3
MDCWDBMBZLORER-UHFFFAOYSA-N triphenyl borate Chemical compound C=1C=CC=CC=1OB(OC=1C=CC=CC=1)OC1=CC=CC=C1 MDCWDBMBZLORER-UHFFFAOYSA-N 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
ZFMOJHVRFMOIGF-UHFFFAOYSA-N 2,4,6-trimethoxy-1,3,5,2,4,6-trioxatriborinane Chemical compound COB1OB(OC)OB(OC)O1 ZFMOJHVRFMOIGF-UHFFFAOYSA-N 0.000 description 2
229910011255 B2O3 Inorganic materials 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
238000009835 boiling Methods 0.000 description 2
238000005485 electric heating Methods 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
125000004430 oxygen atom Chemical group O* 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
IZEVWCPYYXBRCQ-UHFFFAOYSA-N 2,4,6-tri(propan-2-yloxy)-1,3,5,2,4,6-trioxatriborinane Chemical compound CC(C)OB1OB(OC(C)C)OB(OC(C)C)O1 IZEVWCPYYXBRCQ-UHFFFAOYSA-N 0.000 description 1
JMAQTHFIHWVLJK-UHFFFAOYSA-N 2,4,6-triethoxy-1,3,5,2,4,6-trioxatriborinane Chemical compound CCOB1OB(OCC)OB(OCC)O1 JMAQTHFIHWVLJK-UHFFFAOYSA-N 0.000 description 1
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
150000001639 boron compounds Chemical class 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
238000000265 homogenisation Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002605 large molecules Chemical class 0.000 description 1
229920002521 macromolecule Polymers 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
150000003138 primary alcohols Chemical class 0.000 description 1
230000036632 reaction speed Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
KDQYHGMMZKMQAA-UHFFFAOYSA-N trihexyl borate Chemical compound CCCCCCOB(OCCCCCC)OCCCCCC KDQYHGMMZKMQAA-UHFFFAOYSA-N 0.000 description 1
NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
RTMBXAOPKJNOGZ-UHFFFAOYSA-N tris(2-methylphenyl) borate Chemical compound CC1=CC=CC=C1OB(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C RTMBXAOPKJNOGZ-UHFFFAOYSA-N 0.000 description 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)

CH6945559A 1958-02-12 1959-02-12 Verfahren zur Herstellung von Metaborsäureestern und Polyborsäureestern CH401941A (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US71469358A	1958-02-12	1958-02-12
US788040A US3099677A (en)	1959-01-21	1959-01-21	Preparation of metaborate and polyborate esters

Publications (1)

Publication Number	Publication Date
CH401941A true CH401941A (de)	1965-11-15

Family

ID=27109194

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH6945559A CH401941A (de)	1958-02-12	1959-02-12	Verfahren zur Herstellung von Metaborsäureestern und Polyborsäureestern

Country Status (2)

Country	Link
BE (1)	BE575596A (fr)
CH (1)	CH401941A (fr)

1959
- 1959-02-11 BE BE575596A patent/BE575596A/fr unknown
- 1959-02-12 CH CH6945559A patent/CH401941A/de unknown

Also Published As

Publication number	Publication date
BE575596A (fr)	1959-05-29

Publication	Publication Date	Title
DE869956C (de)	1953-03-09	Verfahren zur Herstellung von Organodisiloxanen
DE69832645T2 (de)	2006-08-24	Tetrakis(fluoraryl)-borat/Etherkomplexe und Verfahren zu deren Herstellung
CH365724A (de)	1962-11-30	Verfahren zur Herstellung von Organo-Borverbindungen
DE1168407B (de)	1964-04-23	Verfahren zur Herstellung von Trimethylphosphit oder Triaethylphosphit
DE2556760A1 (de)	1977-06-30	Verfahren zur herstellung von carbodiimiden
CH401941A (de)	1965-11-15	Verfahren zur Herstellung von Metaborsäureestern und Polyborsäureestern
DE68913304T2 (de)	1994-09-08	Transesterifikation von alkoxyestern.
DE2234133A1 (de)	1974-01-24	Verfahren zur herstellung von triarylboranen
CH483397A (de)	1969-12-31	Verfahren zur Herstellung von Phenylalaninderivaten
AT250334B (de)	1966-11-10	Verfahren zur Herstellung von α-Carbalkoxy-β-arylamino-acrylsäureestern
DE1134385B (de)	1962-08-09	Verfahren zur Herstellung eines Borazolderivats
DE1024944B (de)	1958-02-27	Verfahren zur Herstellung von Phosphorigsaeureestern
DD233846A5 (de)	1986-03-12	Verfahren zur herstellung von triarylphosphaten
DE2651775A1 (de)	1977-05-18	Verfahren zur herstellung von triarylboranen
DE1089384B (de)	1960-09-22	Verfahren zur Herstellung von ringfoermigen Borkohlenwasserstoffen
AT255436B (de)	1967-07-10	Verfahren zur Herstellung von Tri-(organoperoxy)-boranen
DE806036C (de)	1951-06-11	Verfahren zur Herstellung von Penicillinsalzen
DE1294376B (de)	1969-05-08	Verfahren zur Herstellung von quartaeren Phosphoniumhalogeniden
CH427770A (de)	1967-01-15	Verfahren zur Herstellung von a-Keto-y-lactonen
DE862607C (de)	1953-01-12	Verfahren zur Herstellung von Triorganosilylphenoxysilanen
DE1063591B (de)	1959-08-20	Verfahren zur Herstellung von in organischen Loesungsmitteln leichtloeslichen basischen Aluminium-alkoholaten
DE2609126A1 (de)	1977-09-08	Verfahren zur herstellung von eckige klammer auf 2-(halogenformyl)- vinyl eckige klammer zu organyl-phosphinsaeurehalogeniden
DE2334609C2 (de)	1981-11-12	Verfahren zur Herstellung von O,O-Dialkyl-O-phenylestern von Thionophosphorsäuren
CH631182A5 (en)	1982-07-30	Process for preparing the hydrazide of diphenylphosphinylacetic acid.
DE3643761A1 (de)	1988-06-30	Reinigung von phosphorsaeureestern