GB599357A - Improvements in the manufacture of pentaerythritol - Google Patents
Improvements in the manufacture of pentaerythritolInfo
- Publication number
- GB599357A GB599357A GB2394245A GB2394245A GB599357A GB 599357 A GB599357 A GB 599357A GB 2394245 A GB2394245 A GB 2394245A GB 2394245 A GB2394245 A GB 2394245A GB 599357 A GB599357 A GB 599357A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acetaldehyde
- formaldehyde
- acid
- solution
- pentaerythritol
- 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
- WXZMFSXDPGVJKK-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 title abstract 4
- 238000004519 manufacturing process Methods 0.000 title 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 abstract 16
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 14
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L Calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 abstract 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 239000001175 calcium sulphate Substances 0.000 abstract 3
- 235000011132 calcium sulphate Nutrition 0.000 abstract 3
- 239000001117 sulphuric acid Substances 0.000 abstract 3
- 235000011149 sulphuric acid Nutrition 0.000 abstract 3
- AYJRCSIUFZENHW-UHFFFAOYSA-L Barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 abstract 2
- 229940044172 CALCIUM FORMATE Drugs 0.000 abstract 2
- CBOCVOKPQGJKKJ-UHFFFAOYSA-L Calcium formate Chemical compound [Ca+2].[O-]C=O.[O-]C=O CBOCVOKPQGJKKJ-UHFFFAOYSA-L 0.000 abstract 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L Calcium hydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 abstract 2
- CEQFOVLGLXCDCX-WUKNDPDISA-N Methyl red Chemical compound C1=CC(N(C)C)=CC=C1\N=N\C1=CC=CC=C1C(O)=O CEQFOVLGLXCDCX-WUKNDPDISA-N 0.000 abstract 2
- 239000004281 calcium formate Substances 0.000 abstract 2
- 235000019255 calcium formate Nutrition 0.000 abstract 2
- 239000000920 calcium hydroxide Substances 0.000 abstract 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 abstract 2
- 235000011116 calcium hydroxide Nutrition 0.000 abstract 2
- 238000001704 evaporation Methods 0.000 abstract 2
- 238000001914 filtration Methods 0.000 abstract 2
- 235000019253 formic acid Nutrition 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxyl anion Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 2
- 239000011541 reaction mixture Substances 0.000 abstract 2
- 238000001256 steam distillation Methods 0.000 abstract 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N Hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 abstract 1
- 229960004011 Methenamine Drugs 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 1
- 239000004312 hexamethylene tetramine Substances 0.000 abstract 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000002002 slurry Substances 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/24—Tetrahydroxylic alcohols, e.g. pentaerythritol
- C07C31/245—Pentaerythritol
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Pentaerythritol is produced from formaldehyde and acetaldehyde in the presence of a strongly basic hydroxide by employing at least 5 moles, and preferably at least 7 moles, of formaldehyde per mole, acetaldehyde and sufficient hydroxide to leave an excess on the disappearance of the acetaldehyde, maintaining the reaction mixture at a temperature not exceeding 33 DEG C. until the disappearance of the acetaldehyde and then, still at a temperature not exceeding 33 DEG C., removing its free alkalinity, preferably by adding sufficient of an acid, e.g. sulphuric or formic acid, to render the solution only slightly acid to an indicator changing colour at about the same acidity as Methyl Red. The unreacted excess of formaldehyde may then be stripped from the reaction mixture, preferably by steam distillation at ordinary or increased pressure. The pentaerythritol may then be recovered in known manner, for instance, when calcium hydroxide has been used, as is preferable, by addition of sufficient sulphuric acid to liberate the formic acid from the calcium formate in the solution, filtration from calcium sulphate, treatment with witherite to convert the calcium sulphate remaining in solution into known sulphate and calcium formate, further filtration and evaporation under reduced pressure. In examples: (1) formaldehyde and later acetaldehyde are added to a slurry of hydrated lime and water, the rate of addition of the acetaldehyde solution being such that the reaction temperature remains at or below 30 DEG C. After adding all the acetaldehyde the mixture is stirred and then cooled to 20 DEG C. when sulphuric acid is added to render the liquor acid to methyl red. The calcium sulphate is filtered off and after steam distillation to remove formaldehyde the pentaerythritol is recovered as above, ammonia being added to the filtered liquor before evaporation to convert any residual formaldehyde into hexamethylene tetramine; (2) as in (1) but using a molar formaldehyde: acetaldehyde ratio of 8 to 1.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB599357A true GB599357A (en) | 1948-03-10 |
Family
ID=1738036
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2394245A Expired GB599357A (en) | 1945-09-17 | Improvements in the manufacture of pentaerythritol |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB599357A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110092711A (en) * | 2019-05-20 | 2019-08-06 | 中国石化长城能源化工（宁夏）有限公司 | A kind of formaldehyde separation method of butanol purifying technique |
| CN110330418A (en) * | 2019-06-20 | 2019-10-15 | 湖北楚星化工股份有限公司 | A method of recycling the formaldehyde gas to volatilize in atmospheric unit in Production of pentaerythritol |
-
1945
- 1945-09-17 GB GB2394245A patent/GB599357A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110092711A (en) * | 2019-05-20 | 2019-08-06 | 中国石化长城能源化工（宁夏）有限公司 | A kind of formaldehyde separation method of butanol purifying technique |
| CN110330418A (en) * | 2019-06-20 | 2019-10-15 | 湖北楚星化工股份有限公司 | A method of recycling the formaldehyde gas to volatilize in atmospheric unit in Production of pentaerythritol |
| CN110330418B (en) * | 2019-06-20 | 2022-03-15 | 湖北楚星化工股份有限公司 | Method for recovering formaldehyde gas volatilized in normal pressure device in pentaerythritol production |
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