US3131208A - Glycol monoborates - Google Patents
Glycol monoborates Download PDFInfo
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- US3131208A US3131208A US193013A US19301362A US3131208A US 3131208 A US3131208 A US 3131208A US 193013 A US193013 A US 193013A US 19301362 A US19301362 A US 19301362A US 3131208 A US3131208 A US 3131208A
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- carbon atoms
- glycol
- present
- methyl
- chloride
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims description 26
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title claims description 15
- 150000004820 halides Chemical class 0.000 claims description 8
- 150000003863 ammonium salts Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 description 20
- -1 aminoalkyl glycol Chemical compound 0.000 description 12
- 239000000376 reactant Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 125000001453 quaternary ammonium group Chemical group 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 150000008282 halocarbons Chemical class 0.000 description 3
- 229910052740 iodine Chemical group 0.000 description 3
- 239000011630 iodine Chemical group 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- UWJKMSTUOSZXAI-UHFFFAOYSA-N CC1OBOC1C Chemical compound CC1OBOC1C UWJKMSTUOSZXAI-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- NCWDBNBNYVVARF-UHFFFAOYSA-N 1,3,2-dioxaborolane Chemical compound B1OCCO1 NCWDBNBNYVVARF-UHFFFAOYSA-N 0.000 description 1
- SQCZQTSHSZLZIQ-UHFFFAOYSA-N 1-chloropentane Chemical compound CCCCCCl SQCZQTSHSZLZIQ-UHFFFAOYSA-N 0.000 description 1
- YFTHTJAPODJVSL-UHFFFAOYSA-N 2-(1-benzothiophen-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(SC=C2)C2=C1 YFTHTJAPODJVSL-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- NFLGILHQOYHUJY-UHFFFAOYSA-N 4-methyl-1,3,2-dioxaborinane Chemical compound CC1CCOBO1 NFLGILHQOYHUJY-UHFFFAOYSA-N 0.000 description 1
- JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- HFEHLDPGIKPNKL-UHFFFAOYSA-N allyl iodide Chemical compound ICC=C HFEHLDPGIKPNKL-UHFFFAOYSA-N 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 239000000022 bacteriostatic agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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)
- C10L1/301—Organic compounds compounds not mentioned before (complexes) derived from metals
- C10L1/303—Organic compounds compounds not mentioned before (complexes) derived from metals boron compounds
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/16—Anti-static materials
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
- D06L1/00—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods
- D06L1/02—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using organic solvents
- D06L1/04—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using organic solvents combined with specific additives
Definitions
- the present invention relates to a new class of glycol monoborate compounds, the quaternary ammonium alkyl glycol monoborate halides, and has further reference to a method for preparing the same.
- the present invention comprises the quaternary ammonium aikyl glycol monoborate halides of the formula where R is an alhylene radical of from 2 to 3 carbon atoms in length and containing a total of from 2 to 20 carbon atoms, R is an allrylene radical of from 2 to 3 carbon atoms in length and containing a total of from 2 to 5 carbon atoms, R and R are alkyl radicals of from 1 to 18 carbon atoms, R, is selected from the group consisting of benzyl, allyl, and primary alkyl of from 1 to 18 carbon atoms, and X is selected from the group consisting of bromine, chlorine and iodine.
- the quaternary ammonium a'll'yl glycol monoborate halides of the present invention have a wide variety of industrial applic tions. They can be used in resins and coating compositions as anti-static agents. They have use as active bactericides and fungicides in soap, detergents and in dry cleaning compositions, and they are effective herbicides when used alone or in combination with other phytotoxie ma erials. Additionally, the present compounds have utility as bacteriostatic agents which prevent microbiological degradation and sludge formation when added to hydrocarbon fuels such as gasoline, jet engine fuels and diesel fuels.
- the preferred method for performing the above reaction is a direct single-step process which involves admixing an aminoalkyl glycol monoborate ester with an applicable organohalide, with or without the presence of a heat transfer medium which is inert to the reactants.
- the reaction mixture is heated to a temperature of from about 50 C. to about 250 C. and the desired quaternary ammonium alkyl glycol monoborate halide is recovered from the resultant reaction mass.
- the organohalide reactant used in the present invention is a lower alkyl halide of from 1 to 3 carbon atoms
- the reactant is a gas at the stated reaction temperatures. Therefore, when employing alkyl halides of from 1 to 3 carbon atoms as reactants, I perform the present process in a closed system, to more adequately utilize the reactant by preventing its escape from the reaction system.
- the present reaction will proceed with or Without employing an inert solvent as a heat transfer medium.
- the reaction proweds more readily and the recovery of a substantially pure product is easier when a solvent or heat transfer medium is present, and in the preferred embodiment of the invention the reaction is carried out in the presence of a solvent which is inert to the reactants.
- the common hydrocarbon solvents such as benzene, n-heptane, xylene, aliphatic naphtha, toluene, etc, are inert to the present reactants and are typical of the solvents which are applicable in the present process.
- the first of these are the aminoalkyl glycol monoborate esters having the foimula where R is an alkylene radical of from 2. to 3 carbon atoms in length and containing a total of from 2 to 20 carbon atoms, R is an alkylene radical of from 2 to 3 carbon atoms in length and containing a total of from 2 to 5 carbon atoms, and R and R are alkyl radicals of from 1 to 18 carbon atoms.
- the aminoalkyl glycol monoborate esters are obtained by reacting boric acid or boron tiioxide with an applicable glycol and an applicable aminoalkanol. The following example is given to lllustrate a method for producing these compounds.
- R is an alkylene radical of from 2 to 3 carbon atoms in length and containing a total of from 2 to 20 carbon atoms
- R is an alkylene radical of from 2 to 3 carbon atoms in length and containing a total of from 2 to 5 carbon atoms
- R and R are alkyl of from 1 to 18 carbon atoms
- R is selected from the group consisting of benzyl, allyl, and primary alkyl of from 1 to 18 carbon atoms
- X is a halogen selected from the group consisting of bromine, chlorine and iodine.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Textile Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
United States Patent 3,131,203 GLYCOL MQNGEGRATES William G. Woods, Anaheim, Calif., assignor to United States Borax Chemical Corporation, Los Angeles, (Salli, a corporation of Nevada No Drawing. Filed May 7, E62, Ser. No. 193,013 Claims. (Cl. 260-462) The present invention relates to a new class of glycol monoborate compounds, the quaternary ammonium alkyl glycol monoborate halides, and has further reference to a method for preparing the same.
it is, therefore, the principal object of the present invention to provide as new compositions the quaternary ammonium alkyl glycol monoborate halides.
It is a further object of this invention to provide a method for preparing the quaternary ammonium alityl glycol monoborate halides.
Other objects of the present invention will appear as the description proceeds.
To the accomplishment of the foregoing and related ends, said invention then comprises the features hereinafter fully described and particularly pointed out in the claims, the following description setting forth in detail certain illustrative embodiments of the invention, these being indicative, however, of but a few of the various Ways in which the principle of the invention may be employed.
Broadly stated, the present invention comprises the quaternary ammonium aikyl glycol monoborate halides of the formula where R is an alhylene radical of from 2 to 3 carbon atoms in length and containing a total of from 2 to 20 carbon atoms, R is an allrylene radical of from 2 to 3 carbon atoms in length and containing a total of from 2 to 5 carbon atoms, R and R are alkyl radicals of from 1 to 18 carbon atoms, R, is selected from the group consisting of benzyl, allyl, and primary alkyl of from 1 to 18 carbon atoms, and X is selected from the group consisting of bromine, chlorine and iodine.
The quaternary ammonium a'll'yl glycol monoborate halides of the present invention have a wide variety of industrial applic tions. They can be used in resins and coating compositions as anti-static agents. They have use as active bactericides and fungicides in soap, detergents and in dry cleaning compositions, and they are effective herbicides when used alone or in combination with other phytotoxie ma erials. Additionally, the present compounds have utility as bacteriostatic agents which prevent microbiological degradation and sludge formation when added to hydrocarbon fuels such as gasoline, jet engine fuels and diesel fuels.
The method for prepa ing the quaternary ammonium alkyl glycol monoborate halides can best be illustrated by the following equation:
where R, R R R R and X are as defined in the foregoing broadly stated paragraph. The reaction will 3,131,208 Patented Apr. 28,1964
proceed when there is an excess of either reactant present. Such excess, however, tends to interfere with the separation of the desired product from the reaction mass, and for the sake of economy and ease of separation, in
the preferred embodiment of the invention, I use equi- 10131 amounts of the reactants.
The preferred method for performing the above reaction is a direct single-step process which involves admixing an aminoalkyl glycol monoborate ester with an applicable organohalide, with or without the presence of a heat transfer medium which is inert to the reactants. The reaction mixture is heated to a temperature of from about 50 C. to about 250 C. and the desired quaternary ammonium alkyl glycol monoborate halide is recovered from the resultant reaction mass. I
It will be noted that when the organohalide reactant used in the present invention is a lower alkyl halide of from 1 to 3 carbon atoms, the reactant is a gas at the stated reaction temperatures. Therefore, when employing alkyl halides of from 1 to 3 carbon atoms as reactants, I perform the present process in a closed system, to more adequately utilize the reactant by preventing its escape from the reaction system.
it will also be noted -that the present reaction will proceed with or Without employing an inert solvent as a heat transfer medium. However, the reaction proweds more readily and the recovery of a substantially pure product is easier when a solvent or heat transfer medium is present, and in the preferred embodiment of the invention the reaction is carried out in the presence of a solvent which is inert to the reactants. The common hydrocarbon solvents such as benzene, n-heptane, xylene, aliphatic naphtha, toluene, etc, are inert to the present reactants and are typical of the solvents which are applicable in the present process.
Referring to the reactants applicable to the present invention, the first of these are the aminoalkyl glycol monoborate esters having the foimula where R is an alkylene radical of from 2. to 3 carbon atoms in length and containing a total of from 2 to 20 carbon atoms, R is an alkylene radical of from 2 to 3 carbon atoms in length and containing a total of from 2 to 5 carbon atoms, and R and R are alkyl radicals of from 1 to 18 carbon atoms. The aminoalkyl glycol monoborate esters are obtained by reacting boric acid or boron tiioxide with an applicable glycol and an applicable aminoalkanol. The following example is given to lllustrate a method for producing these compounds.
A mixture of 103.2 grams (1.00 mole) of N,Ndimethyl- 1-am-1'no-2-propanol, 61.84 grams (1.00 mole) of boric acid, and 90.12 grams (1.00 mole) of 2,3-butanediol was placed in a 2-liter round-bottomed flask containing 400 of benzene. The flask was equipped \with a reflux condenser, a Dean-Stark trap and a magnetic stirrer, and was heated under reflux for about 8 to 10 hours at which time the theoretical amount of Water, 54 ml., had been removed. The excess benzene was then removed by distillation and 149.4 grams (74.3% yield) of Z-(B-dimethylaminoisopropoxy) 4,5 dimethyl 1,3,2 dioxaborolane was recovered, B.P. 131-132 C. (33-85 mm), 11 (24.5 C.) =1.452. Chemical analysis of the product yielded the following data:
Calculated for C H BNO The following list is illustrative of the aminoalkyl glycol monoborate esters applicable to the present invention:
2-(fl-diisopropylaminoethoxy) 1,3,2 dioxaborolane Z-(fi-dioctadecylaminoethoxy) 4 methyl-1,3,2-dioxaborinane 2-(fi-dimethylaminoisopropoxy) 4,5 dimethyl-1,3,2-dioxaborolane 2-(fi-di n hexylaminoisopropoxy)-4,4,6-trimethyl-1,3,2-
dioxaborinane 2-('y-diethylaminopropoxy) 4,5 dimethyl-1,3,2-dioxohorolane 2-( -diisoamylpropoxy) 1,3,2 dioxaborinane 2-(N,N-dimethyl ,8 methyl v aminopropxy)-5- methyl-S-ethyl-I,3,2-dioxaborinane 2- (N, N-di-n-octyl fl methyl-' -aminopropoxy)-4-rnethyl- 1,3,2-dioxaborolane 2(N,N-di-n-propyl [3,5 dimethyl- -aminopropoxy)-4,
4,6-trimethyl-1,3,2-dioxaborinane 2-(N;N-diisohutyl 18,19 dimethyl-y-aminopropoxy)1,3,2-
dioxaborolane Z-(N-rnethyl-N-n-butyl 8 aminoethoxy)-4-propyl-5- ethyl-1,3,2-diox-aborinane 2-(N-ethyl-N-octadecyl- B aminoisopropoxy 4,4,6 trimethyl-1,3,2-dioxaborinane 2-(N-isopropyl N octyl-y-aminopropoxy)-4-methyl- 1,3,2-dioxaborolane 2-(N-methyl N ethyl-5,5-dimethyl-y-aminopropoxy)- 4-methyl-1,3,2-dioxaborolane The second group of reactants are the organohalides having the formula XR where R is either a primary alkyl radical of from 1 to 18 carbon atoms, benzyl or allyl, and X is either bromine, chlorine, or iodine. The following list is illustrative of such compounds:
Methyl iodide Methyl bromide Ethyl chloride n-Propyl chloride n-Butyl bromide n-Amyl chloride n-Hexyl iodide n-Heptyl chloride n-Octyl chloride n-Decyl iodide n-Dodecyl bromide n-Hexadecyl iodide n-Octodecyl bromide n-Hexyl chloride Benzyl chloride Benzyl bromide Allyl chloride Allyl iodide It is to be clearly understood that the foregoing lists are only a partial enumeration of the reactants applicable to the present invention and are in no Way intended to limit the invention.
So that the present invention can be more clearly understood, the following examples are given for illustrative purposes:
Calculated for C H BClNO Percent B 3.17 Cl 10.38
4 Found in product:
Percent B 3.11 C1 9.84
Calculated fOI' C1 H33BC1NO3:
Percent Cl 10.63 Found in product:
A mixture of 51.44 grams (0.20 mole) of Z-(q -diethylaminopropoxy) 5 methyl 5 ethyl-1,3,2-dioxaborinane and 28.39 grams (0.20 mole) of methyl iodide were placed in an autoclave under .a nitrogen atmosphere. The autoclave was heated at from about C. to about 200 C. for about 4 hours. The reaction mass was allowed to cool to about ambient temperature, and the volatile materials were removed from the autoclave by distillation at reduced pressure to yield the desired product, 2-(7-diethylmethylammoniumpropoxy) 5 methyl 5 ethyl-1, 3,2-di0xaborinane iodide. Chemical analysis of the produot yielded the following data:
Calculated for C H BINO Percent I 31.80 Found in product:
Percent Br 17.75 Found in product:
Other modes of applying the principle of the invention may be employed, change being made as regards the details described, provided the features stated in any of the following claims or the equivalent of such be employed.
where R is an alkylene radical of from 2 to 3 carbon atoms in length and containing a total of from 2 to 20 carbon atoms, R is an alkylene radical of from 2 to 3 carbon atoms in length and containing a total of from 2 to 5 carbon atoms, R and R are alkyl of from 1 to 18 carbon atoms, R; is selected from the group consisting of benzyl, allyl, and primary alkyl of from 1 to 18 carbon atoms, and X is a halogen selected from the group consisting of bromine, chlorine and iodine.
2. 2 (/8 dimethylbenzylarnmoniumethoxy) -4,4,6-trimethyl-1,3,2-dioxaborinane chloride.
3. 2 (t3 diisopropylallylarnmoniumisopropoxy)-4,5- dimethyl-l,3,2-dioxaborolane chloride.
4. 2 ('y diethylmethylammoniumpropoxy)-5methy1- S-ethyl-l,3,2-dioxaborinane iodide.
5. 2 (B diethyl'dodecylammoniumethoxy)-4-rnethyl- 10 1,3,2-dioxaborolane bromide.
References Cited in the file of this patent UNITED STATES PATENTS 2,883,373 Bossard et a1. Apr. 21, 1959 2,972,508 Kruckenberg et a1 Feb. 21, 1961
Claims (1)
1. QUATERNARY AMMONIUM ALKYL GLYCOL MONOBORATE HALIDES OF THE FORMULA
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US193013A US3131208A (en) | 1962-05-07 | 1962-05-07 | Glycol monoborates |
| GB2777/63A GB978340A (en) | 1962-05-07 | 1963-01-22 | Improvements relating to glycol monoborate compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US193013A US3131208A (en) | 1962-05-07 | 1962-05-07 | Glycol monoborates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3131208A true US3131208A (en) | 1964-04-28 |
Family
ID=22711933
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US193013A Expired - Lifetime US3131208A (en) | 1962-05-07 | 1962-05-07 | Glycol monoborates |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US3131208A (en) |
| GB (1) | GB978340A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3325262A (en) * | 1963-08-01 | 1967-06-13 | Standard Oil Co | Glycol borate amine salts and compositions containing the same |
| WO1983004255A1 (en) * | 1982-05-26 | 1983-12-08 | The Children's Hospital Medical Center | Reporter compounds |
| US4537773A (en) * | 1983-12-05 | 1985-08-27 | E. I. Du Pont De Nemours And Company | α-Aminoboronic acid derivatives |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2883373A (en) * | 1955-01-28 | 1959-04-21 | Geigy Ag J R | Water soluble azo colour salts |
| US2972508A (en) * | 1955-12-29 | 1961-02-21 | Bayer Ag | Dyeing of polymers of acrylonitrile |
-
1962
- 1962-05-07 US US193013A patent/US3131208A/en not_active Expired - Lifetime
-
1963
- 1963-01-22 GB GB2777/63A patent/GB978340A/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2883373A (en) * | 1955-01-28 | 1959-04-21 | Geigy Ag J R | Water soluble azo colour salts |
| US2972508A (en) * | 1955-12-29 | 1961-02-21 | Bayer Ag | Dyeing of polymers of acrylonitrile |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3325262A (en) * | 1963-08-01 | 1967-06-13 | Standard Oil Co | Glycol borate amine salts and compositions containing the same |
| WO1983004255A1 (en) * | 1982-05-26 | 1983-12-08 | The Children's Hospital Medical Center | Reporter compounds |
| US4537773A (en) * | 1983-12-05 | 1985-08-27 | E. I. Du Pont De Nemours And Company | α-Aminoboronic acid derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| GB978340A (en) | 1964-12-23 |
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