US3024265A - Preparation of dialkoxyvinylboranes - Google Patents

Preparation of dialkoxyvinylboranes Download PDF

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Publication number
US3024265A
US3024265A US67155A US6715560A US3024265A US 3024265 A US3024265 A US 3024265A US 67155 A US67155 A US 67155A US 6715560 A US6715560 A US 6715560A US 3024265 A US3024265 A US 3024265A
Authority
US
United States
Prior art keywords
dialkoxyvinylboranes
mineral oil
metal
general formula
trialkoxyvinylborate
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 - Lifetime
Application number
US67155A
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English (en)
Inventor
George W Willcockson
Joseph K Sandie
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
US Borax Inc
Original Assignee
United States Borax and Chemical Corp
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.)
Filing date
Publication date
Application filed by United States Borax and Chemical Corp filed Critical United States Borax and Chemical Corp
Priority to US67155A priority Critical patent/US3024265A/en
Priority to GB27747/61A priority patent/GB936369A/en
Priority to CH1062561A priority patent/CH397674A/de
Priority to DEU8339A priority patent/DE1138774B/de
Application granted granted Critical
Publication of US3024265A publication Critical patent/US3024265A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/55—Boron-containing compounds

Definitions

  • This invention relates to an improved process for the preparation of dialkoxyvinylboranes.
  • the present invention comprises the method of preparing dialkoxyvinylboranes having the general formula which comprises heating a metal trialkoxvinylborate having the general formula in an inert solvent until said metal trialkoxyvinylborate is thermally decomposed and distilling substantially pure dialkoxyvinylborane as it is formed from said solvent, said solvent being selected from the group consisting of anhydrous hydrocarbons, chlorinated aromatic hydrocarbons, and ethereal solvents having a boiling point greater than about 150 C., and when R is an alkyl group and M is a material selected from the group consisting of MgCl and MgBr.
  • the present invention can he used to prepare the dialkoxyvinylboranes in a continuous manner. Distillation of the dialkoxyvinylboranes may be started immediately upon reaching the decomposition temperature of the vinyltrialkoxyborate, and by maintaining a balanced continuous feed and discharge system while maintaining the required decomposition temperature the process can be performed continuously. Still further, the present process can be carried out at atmospheric or reduced pressures.
  • the present invention is relatively simple and it eliminates the necessity for additional reactants other than the metal trialkoxyvinylborates and is easily carried out in conventional distillation equipment.
  • R is an alkyl group and M is either MgCl or MgBr.
  • One easy method of making them is by the reaction of the vinylmagnesium chloride or bromide with a trialkylborate ester.
  • the number of carbon atoms in the alkyl group of the ester is immaterial.
  • Trimethyl borate or trinonyl borate or borate esters having even longer carbon chains can be made and the corresponding metal trialkoxyvinylborate can be derived from these esters.
  • metal trialkoxyvinylborates the alkyl portion of which contains from 1 to 4 carbon atoms.
  • size-of the alkyl group is immaterial to the present process.
  • Any anhydrous hydrocarbon, chlorinated aromatic hydrocarbon or ethereal solvent having a boiling point higher than about 150 C. which is inert to the metal trialkoxyvinylborate is applicable to the present invention.
  • the following list is illustrative of this group of compounds:
  • a three-liter, 3-necked, round-bottomed flask equipped with a motor stirrer, a pot thermometer, anitrogen inlet tube and a distillation assembly was used in each of the following examples.
  • the apparatus was flushed with-dry,
  • bromomagnesium triisopropoxyvinylborate was placed in the flask with 1200 ml. of light mineral oil. At a pot temperature of 163 C. the first of the distillate was observed. The heat was slowly increased to 250 C. and after about 30 minutes the distillate stopped coming over and the temperature was lowered. The total yield of product was 59 grams,
  • the method of preparing dimethoxyvinylborane which comprises heating chloromagnesium trimethoxyvinylborate in mineral oil at a temperature of from about 150 C. ot about 250 C. until said chloromagnesiumtrimethoxyvinylborate is thermally decomposed and distilling substantially pure dimethoxyvinylborane as it is formed from said mineral oil.
  • the method of preparing diethoxyvinylborane which comprises heating chloromagnesium triethoxyvinylborate in mineral oil at a temperature of from about 150 C. to about 250 C. until said chloromagnesium triethoxyvinylborate is thermally decomposed and distilling substantially pure diethoxyvinylborane as it is formed from said mineral oil.
  • the method of preparing diisopropoxyvinylborane which comprises heating bromomagnesium triisopropoxyvinylborate in mineral oil at a temperature of from about C. to about 250 C. until said bromomagnesiumtriisopropoxyvinylborate is thermally decomposed and distilling substantially pure diisopropoxyvinylborane as it is formed from said mineral oil.
  • the method of preparing di-n-butoxyvinylborane which comprises heating bromomagnesium tri-n-butoxyvinylborate in mineral oil at a temperature of from about 160 C. to about 260 C. until said bromomagnesium tri-n-butoxyvinylborane is thermally decomposed and distilling substantially pure dibutoxyvinylborane as it is formed from said mineral oil.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
US67155A 1960-11-04 1960-11-04 Preparation of dialkoxyvinylboranes Expired - Lifetime US3024265A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US67155A US3024265A (en) 1960-11-04 1960-11-04 Preparation of dialkoxyvinylboranes
GB27747/61A GB936369A (en) 1960-11-04 1961-07-31 Preparation of dialkoxyvinylboranes
CH1062561A CH397674A (de) 1960-11-04 1961-09-13 Verfahren zur Herstellung von Dialkoxyvinylboran
DEU8339A DE1138774B (de) 1960-11-04 1961-09-15 Verfahren zur Herstellung von Dialkoxyvinylboranen

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US67155A US3024265A (en) 1960-11-04 1960-11-04 Preparation of dialkoxyvinylboranes

Publications (1)

Publication Number Publication Date
US3024265A true US3024265A (en) 1962-03-06

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
US67155A Expired - Lifetime US3024265A (en) 1960-11-04 1960-11-04 Preparation of dialkoxyvinylboranes

Country Status (4)

Country Link
US (1) US3024265A (de)
CH (1) CH397674A (de)
DE (1) DE1138774B (de)
GB (1) GB936369A (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5788552A (en) * 1995-12-01 1998-08-04 Alioto; Frank J. Educational device for teaching the severely mentally retarded

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Also Published As

Publication number Publication date
DE1138774B (de) 1962-10-31
GB936369A (en) 1963-09-11
CH397674A (de) 1965-08-31

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