GB463545A - Improvements in or relating to the production of boron compounds and their use as catalysts - Google Patents
Improvements in or relating to the production of boron compounds and their use as catalystsInfo
- Publication number
- GB463545A GB463545A GB2388535A GB2388535A GB463545A GB 463545 A GB463545 A GB 463545A GB 2388535 A GB2388535 A GB 2388535A GB 2388535 A GB2388535 A GB 2388535A GB 463545 A GB463545 A GB 463545A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- reaction
- produce
- propylene
- fluoride
- 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
Links
- 239000003054 catalyst Substances 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title abstract 3
- 150000001639 boron compounds Chemical class 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 12
- 238000006243 chemical reaction Methods 0.000 abstract 11
- 239000002253 acid Substances 0.000 abstract 10
- 229910015900 BF3 Inorganic materials 0.000 abstract 9
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 abstract 9
- -1 butylene, propylene Chemical group 0.000 abstract 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 6
- 229930195733 hydrocarbon Natural products 0.000 abstract 6
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract 6
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 6
- YQUQWHNMBPIWGK-UHFFFAOYSA-N 4-isopropylphenol Chemical compound CC(C)C1=CC=C(O)C=C1 YQUQWHNMBPIWGK-UHFFFAOYSA-N 0.000 abstract 4
- 239000004215 Carbon black (E152) Substances 0.000 abstract 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 4
- 239000005977 Ethylene Substances 0.000 abstract 4
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 abstract 4
- 150000002148 esters Chemical class 0.000 abstract 4
- 150000002430 hydrocarbons Chemical class 0.000 abstract 4
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 abstract 4
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 abstract 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 abstract 4
- 150000002989 phenols Chemical class 0.000 abstract 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 abstract 3
- 229910000040 hydrogen fluoride Inorganic materials 0.000 abstract 3
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 abstract 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 abstract 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract 2
- 150000001298 alcohols Chemical class 0.000 abstract 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 abstract 2
- 239000004327 boric acid Substances 0.000 abstract 2
- 229910052810 boron oxide Inorganic materials 0.000 abstract 2
- WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 abstract 2
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropyl acetate Chemical class CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 abstract 2
- 229940101209 mercuric oxide Drugs 0.000 abstract 2
- 229940102398 methyl anthranilate Drugs 0.000 abstract 2
- 229940095102 methyl benzoate Drugs 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 150000007524 organic acids Chemical class 0.000 abstract 2
- 235000005985 organic acids Nutrition 0.000 abstract 2
- 150000008379 phenol ethers Chemical class 0.000 abstract 2
- 238000006116 polymerization reaction Methods 0.000 abstract 2
- ZYNMJJNWXVKJJV-UHFFFAOYSA-N propan-2-yloxybenzene Chemical compound CC(C)OC1=CC=CC=C1 ZYNMJJNWXVKJJV-UHFFFAOYSA-N 0.000 abstract 2
- 239000001632 sodium acetate Substances 0.000 abstract 2
- 235000017281 sodium acetate Nutrition 0.000 abstract 2
- 239000001117 sulphuric acid Substances 0.000 abstract 2
- 235000011149 sulphuric acid Nutrition 0.000 abstract 2
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 abstract 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 abstract 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 abstract 1
- 229910001634 calcium fluoride Inorganic materials 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B35/00—Boron; Compounds thereof
- C01B35/06—Boron halogen compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Dihydroxyfluoboric acid or its addition compound with boron fluoride may be used in place of boron fluoride in reactions where the latter functions as a catalyst. The reaction in question described are: the polymerization of unsaturated hydrocarbons such as ethylene or propylene if desired under pressure, the esterifying of organic acids with the appropriate alcohols to produce esters such as ethyl, methyl or isopropyl acetates, methyl benzoate and methyl anthranilate or with unsaturated compounds such as butylene, propylene, amylene or vinyl chloride to produce esters such as tertiary butyl acetate &c., the reaction of hydrocarbons such as benzene with olefines such as ethylene or propylene to produce alkylated aromatic hydrocarbons, the reaction of phenols with olefines such as propylene to produce alkylated phenols and/or phenol ethers, the reaction of a hydrocarbon, e.g. benzene, or an acid, e.g. acetic acid, with an acetylene hydrocarbon to produce vinyl derivatives, and the production of 2.4-isopropylphenol from isopropyl phenyl ether. According to one example, vinyl acetylene is passed into a mixture of acetic acid, mercuric oxide and dihydroxyfluoboric acid at 25--30 DEG C., the product being neutralized with sodium acetate and fractionated to produce methyl vinyl ketone and acetic anhydride.ALSO:Dihydroxyfluoboric acid is obtained by reacting boron fluoride with boric acid, or anhydrous hydrogen fluoride with boron oxide, and heating the reaction mixture to above the boiling point of dihydroxyfluoboric acid at the pressure employed. The reaction may be effected by passing boron fluoride into a suspension of boric acid in an inert liquid medium such as heptane or octane. When reacting anhydrous hydrogen fluoride with boron oxide, the latter reactant is preferably employed in excess and the hydrogen fluoride may be replaced by equivalent quantities of sulphuric acid and an alkali or alkaline earth fluoride, e.g. calcium fluoride. One mol. of dihydroxyfluoboric acid reacts with one mol. of boron fluoride to form an addition compound which is decomposed on heating with the evolution of boron fluoride. Dihydroxyfluoboric acid or the above referred to addition compound may be decomposed by concentrated sulphuric acid with the evolution of boron fluoride. Dihydroxyfluoboric acid or its addition compound with boron fluoride may be used in place of boron fluoride in reactions where the latter functions as a catalyst. The reaction in question described are: the polymerization of unsaturated hydrocarbons such as ethylene or propylene if desired under pressure, the esterifying of organic acids with the appropriate alcohols to produce esters such as ethyl, methyl or isopropyl acetates, methyl benzoate and methyl anthranilate or with unsaturated compounds such as butylene, propylene, amylene or vinyl chloride to produce esters such as tertiary butyl acetate, &c., the reaction of hydrocarbons such as benzene with olefines such as ethylene or propylene to produce alkylated aromatic hydrocarbons, the reaction of phenols with olefines such as propylene to produce alkylated phenols and/or phenol ethers, the reaction of a hydrocarbon, e.g. benzene, or an acid, e.g. acetic acid, with an acetylene hydrocarbon to produce vinyl derivatives, and the production of 2,4-isopropylphenol from isopropyl phenyl ether. According to one example, vinyl acetylene is passed into a mixture of acetic acid, mercuric oxide and dihydroxyfluoboric acid at 25--30 DEG C., the product being neutralized with sodium acetate and fractionated to produce methyl vinyl ketone and acetic anhydride.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2388535A GB463545A (en) | 1935-08-26 | 1935-08-26 | Improvements in or relating to the production of boron compounds and their use as catalysts |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2388535A GB463545A (en) | 1935-08-26 | 1935-08-26 | Improvements in or relating to the production of boron compounds and their use as catalysts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB463545A true GB463545A (en) | 1937-03-30 |
Family
ID=10202888
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2388535A Expired GB463545A (en) | 1935-08-26 | 1935-08-26 | Improvements in or relating to the production of boron compounds and their use as catalysts |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB463545A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2502337A (en) * | 1944-09-28 | 1950-03-28 | Pure Oil Co | Use of fluoboric acid as a means of removing core sands from castings |
| US4830842A (en) * | 1987-02-19 | 1989-05-16 | Basf Aktiengesellschaft | Preparation of pure boron trifluoride |
-
1935
- 1935-08-26 GB GB2388535A patent/GB463545A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2502337A (en) * | 1944-09-28 | 1950-03-28 | Pure Oil Co | Use of fluoboric acid as a means of removing core sands from castings |
| US4830842A (en) * | 1987-02-19 | 1989-05-16 | Basf Aktiengesellschaft | Preparation of pure boron trifluoride |
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