WO2002022530A2 - Reduced toxycity 1-bromopropane cleaning agent production process - Google Patents
Reduced toxycity 1-bromopropane cleaning agent production process Download PDFInfo
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- WO2002022530A2 WO2002022530A2 PCT/US2001/028649 US0128649W WO0222530A2 WO 2002022530 A2 WO2002022530 A2 WO 2002022530A2 US 0128649 W US0128649 W US 0128649W WO 0222530 A2 WO0222530 A2 WO 0222530A2
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- WO
- WIPO (PCT)
- Prior art keywords
- bromopropane
- propyl alcohol
- composition
- less
- cleaning agent
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 16
- 239000012459 cleaning agent Substances 0.000 title claims abstract description 15
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 title claims description 48
- 238000000034 method Methods 0.000 claims abstract description 34
- 231100000419 toxicity Toxicity 0.000 claims abstract description 13
- 230000001988 toxicity Effects 0.000 claims abstract description 13
- 239000002904 solvent Substances 0.000 claims abstract description 12
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 46
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 39
- 230000008569 process Effects 0.000 claims description 27
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 13
- 239000003381 stabilizer Substances 0.000 claims description 8
- 238000005893 bromination reaction Methods 0.000 claims description 6
- 230000031709 bromination Effects 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 5
- 238000004140 cleaning Methods 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- CYNYIHKIEHGYOZ-ZDOIIHCHSA-N 1-bromopropane Chemical group [13CH3][13CH2]CBr CYNYIHKIEHGYOZ-ZDOIIHCHSA-N 0.000 claims description 3
- 150000001241 acetals Chemical class 0.000 claims description 3
- 239000000853 adhesive Substances 0.000 claims description 3
- 230000001070 adhesive effect Effects 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 239000000976 ink Substances 0.000 claims description 2
- 150000002118 epoxides Chemical class 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 2
- 230000009257 reactivity Effects 0.000 claims 2
- 238000009834 vaporization Methods 0.000 claims 2
- 230000008016 vaporization Effects 0.000 claims 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 239000002689 soil Substances 0.000 abstract description 2
- XELBLRVZYIETED-UHFFFAOYSA-N CC(C)Br.Br Chemical compound CC(C)Br.Br XELBLRVZYIETED-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000005802 health problem Effects 0.000 abstract 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 231100000053 low toxicity Toxicity 0.000 description 4
- 239000013527 degreasing agent Substances 0.000 description 3
- 230000004907 flux Effects 0.000 description 3
- 239000002529 flux (metallurgy) Substances 0.000 description 3
- WTZJRKRVDNASJG-UHFFFAOYSA-N BrC(C)C.C(C)(C)Br Chemical compound BrC(C)C.C(C)(C)Br WTZJRKRVDNASJG-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 230000004075 alteration Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 230000000779 depleting effect Effects 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 231100000024 genotoxic Toxicity 0.000 description 2
- 230000001738 genotoxic effect Effects 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- CMQUQOHNANGDOR-UHFFFAOYSA-N 2,3-dibromo-4-(2,4-dibromo-5-hydroxyphenyl)phenol Chemical compound BrC1=C(Br)C(O)=CC=C1C1=CC(O)=C(Br)C=C1Br CMQUQOHNANGDOR-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 208000032170 Congenital Abnormalities Diseases 0.000 description 1
- 206010010356 Congenital anomaly Diseases 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000007698 birth defect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- -1 coatings Substances 0.000 description 1
- 208000002173 dizziness Diseases 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 231100000206 health hazard Toxicity 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 231100000616 occupational exposure limit Toxicity 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/42—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/075—Acyclic saturated compounds containing halogen atoms containing bromine
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
- C09D11/033—Printing inks characterised by features other than the chemical nature of the binder characterised by the solvent
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/20—Diluents or solvents
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/24—Organic compounds containing halogen
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/50—Solvents
- C11D7/5004—Organic solvents
- C11D7/5018—Halogenated solvents
-
- C11D2111/22—
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Cleaning And De-Greasing Of Metallic Materials By Chemical Methods (AREA)
- Detergent Compositions (AREA)
Abstract
A method for the production of a cleanining agent and a solvent carrier with reduced toxicity resulting from lower isoropyl bromide (2-bromopropane) content will be described. The cleaning agents are effective for removal of various soils but have a lower tendency to create health problems upon inhalation.
Description
REDUCED TOXICITY 1-BROMOPROPANE CLEANING AGENT PRODUCTION
PROCESS
CROSS NOTING TO RELATED APPLICATIONS
This application is a continuation - in- part of U.S. Application Serial No. 09/546,490, filed April 10, 2000 which is a divisional of U. S. Application Serial No. 09/022,779, filed February 12, 1998, now U.S. Patent No. 6,048,471, which claims priority to Provisional Application Serial No. 60/053,073 filed July 18, 1997.
FIELD OF THE INVENTION
This invention pertains to the field of solvents. In particular, this invention pertains to the production and use of 1-brompropane as a reduced toxicity cleaning agent.
BACKGROUND OF THE INVENTION
Solvent cleaning of articles containing fluxes, greases and various soils has been an industrial and commercial standard for many years. However, solvents have several problems which have concerned environmentalists and toxicologists. Many non-flammable solvents have been classified as ozone depleting compounds because they contain chlorine or bromine atoms and have been banned under the Montreal Protocol. Other solvents, such as hydrocarbon-based
solvents, have fallen out of favor because they have been classified by the United States Environmental Protection Agency (U.S.E.P.A) and other international regulatory agencies as materials that contribute to the formation of ground based ozone and smog. Still other solvents have been banned due to high inherent toxicity upon inhalation by the user. These toxic effects can be headaches, nausea, dizziness, liver disease or worse.
One of the newest solvents to be considered as a candidate to replace some of the banned ozone depleting type compounds is 1-bromopropane (n-propyl bromide or nPB) . 1- bromopropane has a very low ozone depletion potential of only 0.014 and a very short atmospheric lifetime of about 11 days. 1-bromopropane also has relatively low toxicity to mammals. A workplace exposure limit for handlers of 1-bromopropane has been established by independent testing to be 100 ppm for an 8 hour workday.
A negative consequence of the manufacturing process currently used in production of 1-bromopropane has been the production of an isomer of 1-bromopropane which is 2- bromopropane (isopropyl bromide) . 2-bromopropane has been linked to birth defects and is known as genotoxic.
United States Patent No. 6,049,014 describes the production of n-propyl bromide by a non-aqueous propyl alcohol and tetrabromobisphenol process. This process produces n-propyl bromide which contains an unacceptable and
unsafe level of isopropyl bromide (2-bromopropane) . The n- propyl bromide produced from this process may be suitable as a pharmaceutical intermediate however the process for producing the n-propyl bromide is not as safe as the process shown according to this application which minimizes isopropyl bromide .
Other methods for producing n-propyl bromide are known. For example, U.S. Patent No. 5,773,672 discloses a process for producing n-propyl bromide which does not use n-propyl alcohol. JP8337795A2, JP10046197A2, JP11246898A2, JP7150197A2, JP6220494A2, JP09302389A2, U.S. Patent No. 5,824,162, U.S. Patent No. 5,707,954, U.S. Patent No. 5,690,862, U.S. Patent No. 5,679,632, U.S. Patent No. 5,669,985, U.S. Patent No. 5,665,173, U.S. Patent No. 5,616,549, U.S. Patent No. 5,938,859, U.S. Patent No. 5,990,071, U.S. Patent No. 5,858,953 and U.S. Patent No. 5,792,277 all disclose cleaning processes utilizing n-propyl bromide. However, no mention is made of 2-bromopropane content or the toxicity to the user in these patents. Accordingly, the present invention provides a process which produces a cleaning agent comprising 1-bromopropane that is safer than any of the prior art processes known. The production of this safer and less toxic 1-bromopropane based cleaning agent is accomplished by the use of a propyl alcohol feedstock which contains less than 0.1% by weight of isopropyl alcohol. It has been discovered that careful
selection of propyl alcohol feedstock having less than 0.1% by weight of isopropyl alcohol will minimize the unwanted side reaction which produces the isopropyl bromide (2- bromopropane) .
As such, it is the object of this invention to produce a 1-bromopropane based cleaning agent which contains less than 0.1% by weight of 2-bromopropane so as not to create a serious health hazard to the user of a 1-bromopropane based cleaning agent.
SUMMARY OF THE INVENTION
In accordance with the present invention a novel process is described for producing n-propyl bromide with sufficiently low isopropyl bromide content so as to be useful in meeting the occupational exposure limits required by the United States Environmental Protection Agency. The process of the invention produces n-propyl bromide which can be used to produce a low toxicity cleaning agent or solvent carrier.
An object of this invention is directed to a novel high performance processes which produces n-propyl bromide that is of very high purity and mostly free of the unwanted isopropyl bromide which has been shown to be genotoxic.
Another object of this invention is to produce a low toxicity cleaning agent utilizing the high purity, 1- bromopropane produced from the novel process.
A further object of this invention is to demonstrate how
this high purity, low toxicity, 1-bromopropane can be used as a solvent carrier for resins and polymers in the production of adhesives, coatings, inks and the like.
Still other objects, advantages and benefits of the invention will become apparent to those skilled in the art upon a reading and understanding of the following detailed description.
DESCRIPTION OF THE PREFERRED EMBODIMENTS In practicing the invention, any type of bromination reaction utilizing as a starting material, n-propyl alcohol, can be used. Typically HBr, elemental bromine or hydrobromic acid is used to brominate the n-propyl alcohol. This bromination is then followed by distillation. In this process, careful attention will be made as to the content of unwanted alcohols, in particular isopropyl alcohol, present in the n-propyl alcohol feedstock. Gas chromatographic analysis can be used, for example, to determine the concentration of isopropyl alcohol or sec-butanol present in said feedstock. Fractional distillation of technical grade propyl alcohol will reduce the IPA (isopropyl alcohol) content. In a preferred embodiment, a final concentration of 0.1% or less of isopropyl bromide is desired.
The following table lists various sources of n-propyl alcohol which can be used as the starting material in the reaction according to the present invention (identified by
yes in column five of the table) . The n-propyl alcohol feedstock materials have less than or equal to 0.1 wt.% isopropyl alcohol.
Table 1
The following examples demonstrate the production of the lower toxicity n-propyl bromide according to the present invention.
Example 1
N-propyl alcohol having 1% by weight isopropyl alcohol (determined by GC analysis) was obtained. The n-propyl alcohol was fractionally distilled so as to separate the isopropyl alcohol from the n-propyl alcohol. After distillation, GC analysis showed that the isopropyl alcohol content was reduced to 100 ppm or 0.01% by weight. The distilled n-propyl alcohol was then bro inated using the method of mixing an alcohol with bromine, and refluxing the
mix at a temperature of about 79°C for about three hours and separating the reaction products by distillation thereby producing 1-bromopropane. The 1-bromopropane produced was analyzed by GC and was found to contain 80 ppm of isopropyl bromide.
Example 2
5 gallons of the 1-bromopropane from Example 1 was stabilized with 5% by volume of a stabilizer package which contained 68 grams of 1,3 dioxolane, 12 grams of 1,2 butylene oxide and 12 grams of nitromethane. This stabilizer package inhibits the decomposition of the 1-bromopropane and prevents attack upon metals. Stabilizers which may be used include, but are not limited to, epoxides, acetals and nitroparrafins . More or less of the stabilizer can be used depending upon the severity of the application. The mixture was added to the boiling sump of a vapor degreaser. The temperature of the boiling sump is maintained at about 159 to 161°F so that the 1-bromopropane is vaporized. Circuit boards with rosin fluxes and various greases were immersed into the vapors. The fluxes and greases were dissolved by the hot 1- brbmopropane vapors and were removed from the circuit boards . A measurement of the surrounding air was made using a Draeger tube and subsequent GC analysis. The GC analysis showed that the air surrounding the vapor degreaser contained less than 5 ppm of isopropyl bromide therefore indicating a high degree
of safety for the degreaser operator and falling within the permissible guidelines established by the E.P.A.
Example 3 100 ml of the 1-bromopropane prepared in accordance with Example 1 was mixed with 30 grams of various resins and polymers including styrene-butadiene, polychloroprene, natural rubber, urethane, PVC, and acrylic. Ten (10) grams of a hydrocarbon tackifier (i.e. an olefin or methacrylate) can then be added. In each case an adhesive with excellent bond strength was found. Approximately one (1) minute after the 1-bromopropane evaporated, a measurement of the surrounding air was made using the technique of Example 2. The air was found to contain less than 5 ppm of isopropyl bromide indicating a high degree of safety for the user and falling within the permissible guidelines established by the E.P.A.
Various compositions comprising 1-bromopropane, having reduced toxicity to the user, can be formulated utilizing the 1-bromopropane produced in accordance with the- present invention. U.S. Patent Application 6,048,471, incorporated herein by reference, describes various 1-bromopropane containing compositions for which the 1-bromopropane prepared in accordance with the present invention is particularly suitable for.
The invention has been described with reference to the
preferred embodiments. Obviously, modifications and alterations will occur to others upon a reading and understanding of this specification. It is intended to include all such modifications and alterations insofar as they come within the scope of the appended claims or the equivalents thereof.
Claims
1. An improved process for the production of a reduced toxicity cleaning agent comprising 1-bromopropane and containing 0.1% or less of 2-bromopropane wherein said process comprises the step of bromination of n-propyl i alcohol, further wherein the improvement comprises providing an n-propyl alcohol feedstock which contains less than 0.1% by weight of isopropyl alcohol.
2. An improved process for the production of a reduced toxicity cleaning agent comprising 1-bromopropane and containing 0.05% or less of 2-bromopropane wherein said process comprises the step of bromination of a n-propyl alcohol further wherein the improvement comprises providing an n-propyl alcohol feedstock which contains less than 0.05% by weight of isopropyl alcohol.
3. An improved process for the production of a reduced toxicity cleaning agent comprising 1-bromopropane and containing 0.01% or less of 2-bromopropane wherein said process comprises the step of bromination of n-propyl alcohol further wherein the improvement comprises providing an n-propyl alcohol feedstock which contains ' less than 0.01% by weight of isopropyl alcohol.
4. An improved process for the production of a reduced toxicity cleaning agent comprising 1-bromopropane and containing 0.01% or less of 2-bromopropane wherein said process comprises the steps of distilling n-propyl alcohol to a purity of 99.99% n-propyl alcohol, recovery of the n-propyl alcohol from the distillation, and bromination of the n-propyl alcohol recovered from the distillation.
5. A reduced toxicity cleaning agent composition comprising 1-bromopropane produced by the process according to claim 1.
6. The composition of claim 5 further comprising 0.1% to 10% by weight a stabilizer package which prevents decomposition and reactivity of the 1-bromopropane.
7. A reduced toxicity solvent carrier used in production of adhesives, coatings and inks comprising 1-bromopropane produced by the process according to claim 1.
8. The composition of claim 7 further comprising 0.1% to 10% by weight of a stabilizer package which prevents decomposition and reactivity of the 1-bromopropane.
9. The composition of claim 6 wherein the stabilizer package comprises one or more of a compound selected from the group consisting of epoxides, acetals and nitroparaffins .
10. The composition of claim 8 wherein the stabilizer package comprises one or more of a compound selected from the group consisting of epoxides, acetals and nitroparaffins .
11. A method for cleaning circuit boards comprising heating the composition of 1-bromopropane according to claim 6 to its vaporization point and exposure of said circuit boards to vapors emanating from the composition of claim 6.
12. The method according to claim 11 wherein the vapors emanating from the heated 1-bromopropane contain less than 5 ppm of 2-bromopropane.
13. An improved process according to claim 1, wherein the 1-bromopropane produced by the process is fractionally distilled.
14. A method for cleaning circuit boards comprising heating the composition of 1-bromopropane according to claim 6 to its vaporization point and exposure of said circuit boards to vapors emanating from the composition of claim 6 wherein the vapors emanating from the heated 1-bromopropane contain less than 1000 ppm of 2-bromopropane.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2001292649A AU2001292649A1 (en) | 2000-09-13 | 2001-09-13 | Reduced toxycity 1-bromopropane cleaning agent production process |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US66127400A | 2000-09-13 | 2000-09-13 | |
| US09/661,274 | 2000-09-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2002022530A2 true WO2002022530A2 (en) | 2002-03-21 |
| WO2002022530A3 WO2002022530A3 (en) | 2002-08-01 |
Family
ID=24652910
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US2001/028649 WO2002022530A2 (en) | 2000-09-13 | 2001-09-13 | Reduced toxycity 1-bromopropane cleaning agent production process |
Country Status (2)
| Country | Link |
|---|---|
| AU (1) | AU2001292649A1 (en) |
| WO (1) | WO2002022530A2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006119213A2 (en) | 2005-05-03 | 2006-11-09 | Albemarle Corporation | 1-bromopropane having low acidity |
| WO2006119212A3 (en) * | 2005-05-03 | 2006-12-21 | Albemarle Corp | 1-bromopropane having low acidity |
| CN109456141A (en) * | 2018-11-13 | 2019-03-12 | 湖南兴同化学科技有限公司 | A kind of method that oxadiazon etherificate waste water prepares isopropyl bromide |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB565452A (en) * | 1944-01-06 | 1944-11-10 | Arthur Israel Vogel | Improvements in the manufacture of iodides and bromides from alcohols |
| WO1998050517A1 (en) * | 1997-05-02 | 1998-11-12 | Advanced Chemical Design | Environmentally-safe solvent compositions utilizing 1-bromopropane that are stabilized, non-flammable, and have desired solvency characteristics |
| US5858953A (en) * | 1995-04-12 | 1999-01-12 | Tosoh Corporation | Stabilized 1-bromopropane composition |
-
2001
- 2001-09-13 WO PCT/US2001/028649 patent/WO2002022530A2/en active Application Filing
- 2001-09-13 AU AU2001292649A patent/AU2001292649A1/en not_active Abandoned
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB565452A (en) * | 1944-01-06 | 1944-11-10 | Arthur Israel Vogel | Improvements in the manufacture of iodides and bromides from alcohols |
| US5858953A (en) * | 1995-04-12 | 1999-01-12 | Tosoh Corporation | Stabilized 1-bromopropane composition |
| WO1998050517A1 (en) * | 1997-05-02 | 1998-11-12 | Advanced Chemical Design | Environmentally-safe solvent compositions utilizing 1-bromopropane that are stabilized, non-flammable, and have desired solvency characteristics |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006119213A2 (en) | 2005-05-03 | 2006-11-09 | Albemarle Corporation | 1-bromopropane having low acidity |
| WO2006119212A3 (en) * | 2005-05-03 | 2006-12-21 | Albemarle Corp | 1-bromopropane having low acidity |
| WO2006119213A3 (en) * | 2005-05-03 | 2006-12-28 | Albemarle Corp | 1-bromopropane having low acidity |
| CN109456141A (en) * | 2018-11-13 | 2019-03-12 | 湖南兴同化学科技有限公司 | A kind of method that oxadiazon etherificate waste water prepares isopropyl bromide |
| CN109456141B (en) * | 2018-11-13 | 2020-04-07 | 湖南兴同化学科技有限公司 | Method for preparing isopropyl bromide from oxadiazon etherification wastewater |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2002022530A3 (en) | 2002-08-01 |
| AU2001292649A1 (en) | 2002-03-26 |
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