IL25616A - Process for the preparation of organoperoxyboranes - Google Patents

Process for the preparation of organoperoxyboranes

Info

Publication number: IL25616A
Authority: IL; Israel
Prior art keywords: process according; radical; orthoborate; alkyl; tri
Prior art date: 1965-04-21

Application number

IL25616A

Other languages

English (en)

Original Assignee

Rhone Poulenc Sa

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.)

1965-04-21

Filing date

1966-04-20

Publication date

1969-11-12

1965-04-21 Priority claimed from FR14026A external-priority patent/FR1458153A/fr

1965-09-29 Priority claimed from FR33152A external-priority patent/FR1458613A/fr

1965-11-26 Priority claimed from FR39965A external-priority patent/FR89138E/fr

1966-04-20 Application filed by Rhone Poulenc Sa filed Critical Rhone Poulenc Sa

1969-11-12 Publication of IL25616A publication Critical patent/IL25616A/en

Links

238000000034 method Methods 0.000 title claims description 43
238000002360 preparation method Methods 0.000 title claims description 8
239000000203 mixture Substances 0.000 claims description 34
238000006243 chemical reaction Methods 0.000 claims description 26
239000002904 solvent Substances 0.000 claims description 25
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical class B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 22
-1 methylcyclohexyl Chemical group 0.000 claims description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 17
229910000085 borane Inorganic materials 0.000 claims description 15
125000000217 alkyl group Chemical group 0.000 claims description 13
150000001491 aromatic compounds Chemical class 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 10
KUGSJJNCCNSRMM-UHFFFAOYSA-N ethoxyboronic acid Chemical compound CCOB(O)O KUGSJJNCCNSRMM-UHFFFAOYSA-N 0.000 claims description 9
150000002432 hydroperoxides Chemical class 0.000 claims description 6
239000011541 reaction mixture Substances 0.000 claims description 5
125000001931 aliphatic group Chemical group 0.000 claims description 4
150000002989 phenols Chemical class 0.000 claims description 4
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 2
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 2
241001128391 Taia Species 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
239000003960 organic solvent Substances 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
238000009835 boiling Methods 0.000 description 18
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 16
239000001301 oxygen Substances 0.000 description 16
229910052760 oxygen Inorganic materials 0.000 description 16
239000007788 liquid Substances 0.000 description 15
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 13
239000000243 solution Substances 0.000 description 13
238000004821 distillation Methods 0.000 description 12
FGGJBCRKSVGDPO-UHFFFAOYSA-N hydroperoxycyclohexane Chemical compound OOC1CCCCC1 FGGJBCRKSVGDPO-UHFFFAOYSA-N 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
FDGWMSICARGDKC-UHFFFAOYSA-N tricyclohexyloxy borate Chemical compound C1(CCCCC1)OOB(OOC1CCCCC1)OOC1CCCCC1 FDGWMSICARGDKC-UHFFFAOYSA-N 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
UYVXZUTYZGILQG-UHFFFAOYSA-N methoxyboronic acid Chemical compound COB(O)O UYVXZUTYZGILQG-UHFFFAOYSA-N 0.000 description 9
238000007254 oxidation reaction Methods 0.000 description 9
239000000047 product Substances 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
230000003647 oxidation Effects 0.000 description 8
MLSKXPOBNQFGHW-UHFFFAOYSA-N methoxy(dioxido)borane Chemical compound COB([O-])[O-] MLSKXPOBNQFGHW-UHFFFAOYSA-N 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
238000005481 NMR spectroscopy Methods 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical compound CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 4
LTEHWCSSIHAVOQ-UHFFFAOYSA-N tripropyl borate Chemical compound CCCOB(OCCC)OCCC LTEHWCSSIHAVOQ-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
239000000470 constituent Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical class COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
238000005406 washing Methods 0.000 description 3
BSPCSKHALVHRSR-UHFFFAOYSA-N 2-chlorobutane Chemical compound CCC(C)Cl BSPCSKHALVHRSR-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
229910052796 boron Inorganic materials 0.000 description 2
238000001816 cooling Methods 0.000 description 2
YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical compound OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000012467 final product Substances 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
239000010410 layer Substances 0.000 description 2
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
150000002976 peresters Chemical class 0.000 description 2
229930195734 saturated hydrocarbon Natural products 0.000 description 2
238000001577 simple distillation Methods 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
UUUYXCLERBDLEO-UHFFFAOYSA-N 1-hydroperoxy-1-methylcyclohexane Chemical compound OOC1(C)CCCCC1 UUUYXCLERBDLEO-UHFFFAOYSA-N 0.000 description 1
AKUNSTOMHUXJOZ-UHFFFAOYSA-N 1-hydroperoxybutane Chemical compound CCCCOO AKUNSTOMHUXJOZ-UHFFFAOYSA-N 0.000 description 1
ZEOVXNVKXIPWMS-UHFFFAOYSA-N 2,2-dichloropropane Chemical compound CC(C)(Cl)Cl ZEOVXNVKXIPWMS-UHFFFAOYSA-N 0.000 description 1
MOEFFSWKSMRFRQ-UHFFFAOYSA-N 2-ethoxyphenol Chemical class CCOC1=CC=CC=C1O MOEFFSWKSMRFRQ-UHFFFAOYSA-N 0.000 description 1
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
JNMYDPIEECRVJZ-UHFFFAOYSA-N C(C1=CC=CC=C1)OOB Chemical compound C(C1=CC=CC=C1)OOB JNMYDPIEECRVJZ-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
238000006136 alcoholysis reaction Methods 0.000 description 1
125000002723 alicyclic group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
229960002645 boric acid Drugs 0.000 description 1
235000010338 boric acid Nutrition 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000013065 commercial product Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
150000001896 cresols Chemical class 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
WZRXFPOWHQQSRJ-UHFFFAOYSA-N cyclohexyloxyboronic acid Chemical compound OB(O)OC1CCCCC1 WZRXFPOWHQQSRJ-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
SURBAJYBTYLRMQ-UHFFFAOYSA-N dioxido(propan-2-yloxy)borane Chemical compound CC(C)OB([O-])[O-] SURBAJYBTYLRMQ-UHFFFAOYSA-N 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011521 glass Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
YVJRCWCFDJYONJ-UHFFFAOYSA-N hydroperoxymethylbenzene Chemical compound OOCC1=CC=CC=C1 YVJRCWCFDJYONJ-UHFFFAOYSA-N 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
125000003884 phenylalkyl group Chemical group 0.000 description 1
XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
NDRRIWRRYCMFKC-UHFFFAOYSA-N tributoxy borate Chemical class CCCCOOB(OOCCCC)OOCCCC NDRRIWRRYCMFKC-UHFFFAOYSA-N 0.000 description 1
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
YRBBKBBNTQECII-UHFFFAOYSA-N tris(2-phenylpropan-2-yloxy) borate Chemical compound C1(=CC=CC=C1)C(C)(OOB(OOC(C)(C1=CC=CC=C1)C)OOC(C)(C1=CC=CC=C1)C)C YRBBKBBNTQECII-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/60—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by oxidation reactions introducing directly hydroxy groups on a =CH-group belonging to a six-membered aromatic ring with the aid of other oxidants than molecular oxygen or their mixtures with molecular oxygen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
- 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)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

IL25616A 1965-04-21 1966-04-20 Process for the preparation of organoperoxyboranes IL25616A (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
FR14026A FR1458153A (fr)	1965-04-21	1965-04-21	Nouveau procédé pour la préparation d'organoperoxyboranes
FR33152A FR1458613A (fr)	1965-09-29	1965-09-29	Procédé de préparation de composés phénoliques
FR39965A FR89138E (fr)	1965-11-26	1965-11-26	Nouveau procédé pour la préparation d'organoperoxyboranes

Publications (1)

Publication Number	Publication Date
IL25616A true IL25616A (en)	1969-11-12

Family

ID=27242099

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL25616A IL25616A (en)	1965-04-21	1966-04-20	Process for the preparation of organoperoxyboranes

Country Status (8)

Country	Link
BE (1)	BE679792A (fr)
CH (1)	CH443292A (fr)
DE (1)	DE1793671A1 (fr)
DK (1)	DK123532B (fr)
GB (1)	GB1147874A (fr)
IL (1)	IL25616A (fr)
LU (1)	LU50928A1 (fr)
NL (1)	NL6604935A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8904798D0 (en) *	1989-03-02	1989-04-12	Interox Chemicals Ltd	Aldehyde oxidation

1966
- 1966-04-13 NL NL6604935A patent/NL6604935A/xx unknown
- 1966-04-20 DK DK203166AA patent/DK123532B/da unknown
- 1966-04-20 LU LU50928A patent/LU50928A1/xx unknown
- 1966-04-20 BE BE679792D patent/BE679792A/xx unknown
- 1966-04-20 IL IL25616A patent/IL25616A/en unknown
- 1966-04-21 DE DE19661793671 patent/DE1793671A1/de active Pending
- 1966-04-21 CH CH579966A patent/CH443292A/fr unknown
- 1966-04-21 GB GB17571/66A patent/GB1147874A/en not_active Expired

Also Published As

Publication number	Publication date
LU50928A1 (fr)	1966-06-20
BE679792A (fr)	1966-10-20
DK123532B (da)	1972-07-03
DE1593298B2 (de)	1973-01-25
DE1593298A1 (de)	1970-07-23
NL6604935A (fr)	1966-10-24
CH443292A (fr)	1967-09-15
DE1793671A1 (de)	1972-03-30
GB1147874A (en)	1969-04-10

Publication	Publication Date	Title
Brown et al.	1959	Hydroboration. II. A Remarkably Fast Addition of Diborane to Olefins—Scope and Stoichiometry of the Reaction
US4076756A (en)	1978-02-28	Process for the preparation of triarylborane
Hillman	1962	The carbonylation of organoboranes. I. The carbonylation of trialkylboranes. A novel synthesis of trialkylcarbinols
US4046815A (en)	1977-09-06	Process for the preparation of triarylborane
Krishnamurthy et al.	1977	Lithium. beta.-isopinocamphenyl-9-borabicyclo [3.3. 1] nonyl hydride. A new reagent for the asymmetric reduction of ketones with remarkable consistency
US3090801A (en)	1963-05-21	Aryl polyboronic acids and esters and process for their preparation
US3971833A (en)	1976-07-27	Method for the preparation of alcohol-free alkali and alkaline earth metal alcoholates
US3159626A (en)	1964-12-01	Triethylene-diamine alane and a process for its preparation
US3553271A (en)	1971-01-05	Process for the preparation of phenolic compounds
Naruse et al.	1974	The reaction of lithium trialkylalkynylborates with oxiranes: γ-Hydroxyketone synthesis and stereoselective preparation of trisubstituted ethylenes
US2880243A (en)	1959-03-31	Manufacture of trisubstituted boranes
US3622611A (en)	1971-11-23	Process for the preparation of triorganoperoxyboranes
US3709946A (en)	1973-01-09	Preparation of acetylenic alcohols
US2880242A (en)	1959-03-31	Production of trisubstituted boranes
US4005132A (en)	1977-01-25	Process for reacting trialkyl boranes with compounds containing protons
JPS5849389A (ja)	1983-03-23	トリアルキルアルミニウム化合物の製造方法
US2830070A (en)	1958-04-08	Preparation of trimethyl borate
US3238238A (en)	1966-03-01	Selective oxidation of aliphatic hydro- carbons to alcohols in presence of tert-butyl borate
US3129251A (en)	1964-04-14	Preparation of polyols from olefins
US2980507A (en)	1961-04-18	Process for preparing zirconium oxide
US3091627A (en)	1963-05-28	Preparation of alcohols
US3216790A (en)	1965-11-09	Preparation of sodium hydrosulfite
US2886599A (en)	1959-05-12	Process for the production of boron alkyls
US2671812A (en)	1954-03-09	Reaction of ozonides with grignard reagents
US2425343A (en)	1947-08-12	Making cycloalkylacetic acids