GB590571A - Improvements in and relating to a process for reacting olefines with formaldehyde - Google Patents
Improvements in and relating to a process for reacting olefines with formaldehydeInfo
- Publication number
- GB590571A GB590571A GB25733/44A GB2573344A GB590571A GB 590571 A GB590571 A GB 590571A GB 25733/44 A GB25733/44 A GB 25733/44A GB 2573344 A GB2573344 A GB 2573344A GB 590571 A GB590571 A GB 590571A
- Authority
- GB
- United Kingdom
- Prior art keywords
- butylene glycol
- water
- atmospheres
- formaldehyde
- yields
- 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
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 title abstract 8
- 238000000034 method Methods 0.000 title abstract 2
- 229940058015 1,3-butylene glycol Drugs 0.000 abstract 5
- 235000019437 butane-1,3-diol Nutrition 0.000 abstract 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 4
- PUPZLCDOIYMWBV-UHFFFAOYSA-N butylene glycol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 abstract 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 3
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L Calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium monoxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 239000000463 material Substances 0.000 abstract 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 2
- 239000000376 reactant Substances 0.000 abstract 2
- 239000001117 sulphuric acid Substances 0.000 abstract 2
- 235000011149 sulphuric acid Nutrition 0.000 abstract 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-Trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 abstract 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-Propanediol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 abstract 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N Boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 abstract 1
- 210000003298 Dental Enamel Anatomy 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- 229910001209 Low-carbon steel Inorganic materials 0.000 abstract 1
- TZIHFWKZFHZASV-UHFFFAOYSA-N Methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000002378 acidificating Effects 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- 239000000292 calcium oxide Substances 0.000 abstract 1
- 239000001175 calcium sulphate Substances 0.000 abstract 1
- 235000011132 calcium sulphate Nutrition 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 150000002009 diols Chemical class 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- -1 ethylene, propylene Chemical group 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 239000011521 glass Substances 0.000 abstract 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 229910052709 silver Inorganic materials 0.000 abstract 1
- 239000004332 silver Substances 0.000 abstract 1
- BQCADISMDOOEFD-UHFFFAOYSA-N silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 abstract 1
- 229910001220 stainless steel Inorganic materials 0.000 abstract 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Olefines are condensed with formaldehyde or a polymer thereof in the presence of an aqueous acid-reacting condensation catalyst under 75-2000 atmospheres pressure forming 1 : 3-alkane diols or 1 : 3-alkane-diol-cyclic or -linear formals. The temperatures may be 30 DEG C.-250 DEG C. and preferably 100 DEG C.-200 DEG C. When some of the 1,3-alkane-diol-cyclic formals are added to the feed or when the molar ratio of water to formaldehyde is about 8 : 1, the diols are largely formed, but if the water/formaldehyde ratio is 1 : 1 the formals are mainly formed. The preferred olefines are ethylene, propylene or butylene and the catalysts are, e.g hydrated boron fluoride, sulphuric acid, methyl formate, formic acid, acidic clay-like materials, phosphoric acid or calcium sulphate. The reaction vessel is made or lined with an acid resisting material such as stainless or mild steel, copper, silver, nickel, enamel and glass and the process may be conducted continuously. In examples: (1) a mixture of trioxymethylene, water, sulphuric acid and 1,3-butylene glycol cyclic formal is agitated at 165 DEG C. under 600 to 700 atmospheres of propylene pressure. The product is cooled, neutralized with aqueous calcium oxide, filtered and distilled to yield mainly 1,3-butylene glycol with some butylene glycol cyclic formal and isopropanol; (2) the same reactants as in (1) but with less water and without the addition of cyclic formal are agitated at 150 DEG C. and 200 atmospheres propylene pressure. The product is extracted with chloroform and yields 1,3-butylene glycol cyclic formal. The aqueous layer is neutralized and on distillation yields mainly 1,3-butylene glycol linear formals and a little 1,3-butylene glycol; (3) the same reactants as in (2) but with more water are heated at 190 DEG C. under 900 atmospheres ethylene pressure. Extraction with chloroform yields trimethylene glycol cyclic formal and the aqueous layer yields trimethylene glycol. According to the Provisional Specification any high pressure may be employed. Specifications 511,966 and 544,737 are referred to.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB590571A true GB590571A (en) | 1947-07-22 |
Family
ID=1739468
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB25733/44A Expired GB590571A (en) | 1944-12-22 | Improvements in and relating to a process for reacting olefines with formaldehyde |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB590571A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0013600A1 (en) * | 1979-01-05 | 1980-07-23 | Mobil Oil Corporation | Production of alkenols and alkanediols by condensation of aldehyde and ethylenically unsaturated compounds |
| CN108586197A (en) * | 2018-05-03 | 2018-09-28 | 浙江新化化工股份有限公司 | A kind of production method of 1,3 butylene glycol |
-
1944
- 1944-12-22 GB GB25733/44A patent/GB590571A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0013600A1 (en) * | 1979-01-05 | 1980-07-23 | Mobil Oil Corporation | Production of alkenols and alkanediols by condensation of aldehyde and ethylenically unsaturated compounds |
| CN108586197A (en) * | 2018-05-03 | 2018-09-28 | 浙江新化化工股份有限公司 | A kind of production method of 1,3 butylene glycol |
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