US841999A - Process of making formaldehyde sulfoxylates. - Google Patents
Process of making formaldehyde sulfoxylates. Download PDFInfo
- Publication number
- US841999A US841999A US30703206A US1906307032A US841999A US 841999 A US841999 A US 841999A US 30703206 A US30703206 A US 30703206A US 1906307032 A US1906307032 A US 1906307032A US 841999 A US841999 A US 841999A
- Authority
- US
- United States
- Prior art keywords
- sulfoxylates
- formaldehyde
- acetone
- formaldehyde sulfoxylates
- making formaldehyde
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 title description 6
- QJQZEJFUIOWFMS-UHFFFAOYSA-N formaldehyde;sulfanediol Chemical class O=C.OSO QJQZEJFUIOWFMS-UHFFFAOYSA-N 0.000 title description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- -1 ketone sulfoxylates Chemical class 0.000 description 4
- ZQRIKJMJOWMJGA-UHFFFAOYSA-L S([O-])[O-].CC(=O)C.[Na+].[Na+] Chemical compound S([O-])[O-].CC(=O)C.[Na+].[Na+] ZQRIKJMJOWMJGA-UHFFFAOYSA-L 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- HRKQOINLCJTGBK-UHFFFAOYSA-N dihydroxidosulfur Chemical class OSO HRKQOINLCJTGBK-UHFFFAOYSA-N 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- FHIDNBAQOFJWCA-UAKXSSHOSA-N 5-fluorouridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(F)=C1 FHIDNBAQOFJWCA-UAKXSSHOSA-N 0.000 description 1
- 101000685724 Homo sapiens Protein S100-A4 Proteins 0.000 description 1
- 102100023087 Protein S100-A4 Human genes 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- HRKQOINLCJTGBK-UHFFFAOYSA-L dioxidosulfate(2-) Chemical compound [O-]S[O-] HRKQOINLCJTGBK-UHFFFAOYSA-L 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical class OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 229940017705 formaldehyde sulfoxylate Drugs 0.000 description 1
- SBGKURINHGJRFN-UHFFFAOYSA-N hydroxymethanesulfinic acid Chemical compound OCS(O)=O SBGKURINHGJRFN-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C313/02—Sulfinic acids; Derivatives thereof
- C07C313/04—Sulfinic acids; Esters thereof
Definitions
- Ph. D., and WOLDEMAR W LLENBER Phl- D chemists citizens of the Empire of Germany, residing at H6chst-onthe-Main, Ger many,,have invented certain new and useful Improvements in Formaldehyde Sulfoxylates and Processes of Making Same, of which the following is a specification. v
- ketone s'ulfoxylates can also be produced by reducing the products of reaction of bisulfites, sulfurous acid, or hydro sulfite on acetone or ethylmethylketone or by subject'- ing these compounds to reduction in press ence of said ketones;
- the ketone sulfoxylates are obtained, for instance, as follows: Into asolution of sixtyfive parts of acetone in one thousand parts of water are introduced sixty-four parts of sul- 2 5 fur dioxid. One hundred and twenty parts of zinc-dust are thcn'addedwhile stirring and well cooling, and if no further spontaneous heating occurs thetemperature is raised to 50 to 60 ccntigrade. After heating for some hours a solution of acetone .zinc sulfoxylate is obtained, which when treated with sodium carbonate is transformed int acetone sodium sulfoxylate. v
- the rocess for obtaining formaldehyde sulfoxy ate from ketone sulfoxylates may be carried out, for instance, as follows: To a solution containing one hundred and forty parts of acetone sodium sulfoxylate of one hundred percent. strength in one liter of water are added while stirring seventy five parts of formaldehyde of fortyper -cent. strength. -The combination occurs rapidly, and the formaldehyde sodium sulfoxylate may then be obtained in solid form by evaporating in a vacuum, While the acetone is dis tilled ofi.
- other salts-such, for instance, as the zinc salt- may be used in a like manner.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
RUDOLF Mf'lLL-ER AND .-WOLDEMAR WOLLENBERG, or Hooiisr oN-THE- MAIN, GERMANY, AssicNoRs TO FARBWERKE, V-ORM. MEisrEa' LUCIUS & BRUNIN'G, OF HOGHST-ONJIHE-MAIN,'GERMANY, A CORPO- RATION OF GERMANY.
- PROCESS OF-MAKING: YFORMALDIEHYDE SULFOXYLATES.
Specification of Letters Patent. I
Patented. J an. 22, 1907.
Application filed March 20,1906. vi Serial N el 307.032. (Specimens) To all mil/m it may concern.-
Be it known that we, RUDoLF Mt'in En,
Ph. D., and WOLDEMAR W LLENBER Phl- D chemists, citizens of the Empire of Germany, residing at H6chst-onthe-Main, Ger many,,have invented certain new and useful Improvements in Formaldehyde Sulfoxylates and Processes of Making Same, of which the following is a specification. v
As by the action of formaldehyde on h drosulfite 'ketone sulfoxylates mayv also ev obtained by the action ofacetqne or ethylmeth lketone on alkaline hydrosulfites, which may e isolated afterward. by crystallization is These ketone s'ulfoxylates can also be produced by reducing the products of reaction of bisulfites, sulfurous acid, or hydro sulfite on acetone or ethylmethylketone or by subject'- ing these compounds to reduction in press ence of said ketones;
The ketone sulfoxylates are obtained, for instance, as follows: Into asolution of sixtyfive parts of acetone in one thousand parts of water are introduced sixty-four parts of sul- 2 5 fur dioxid. One hundred and twenty parts of zinc-dust are thcn'addedwhile stirring and well cooling, and if no further spontaneous heating occurs thetemperature is raised to 50 to 60 ccntigrade. After heating for some hours a solution of acetone .zinc sulfoxylate is obtained, which when treated with sodium carbonate is transformed int acetone sodium sulfoxylate. v
We have found that lretone sulfoxylates may be transformed into the more stable formaldehyde sulfoxylates if the former are treated with formaldehyde. By the action of the formaldehyde on kctonc sulfoxylatcs' theketone is eliminated with formation of 4 formaldehyde sulfoxylate, which is readily observed in that thesolution of the ketone sulfoxylates treated with the equivalent proportion offormaldehyde no longer reduces indigo-sulfonic acid in the cold. The reaction of this process may be interpreted by the following equation:
The rocess for obtaining formaldehyde sulfoxy ate from ketone sulfoxylates may be carried out, for instance, as follows: To a solution containing one hundred and forty parts of acetone sodium sulfoxylate of one hundred percent. strength in one liter of water are added while stirring seventy five parts of formaldehyde of fortyper -cent. strength. -The combination occurs rapidly, and the formaldehyde sodium sulfoxylate may then be obtained in solid form by evaporating in a vacuum, While the acetone is dis tilled ofi. For the acetone sodium sulfoxylate other salts-such, for instance, as the zinc salt-may be used in a like manner.
Having now described our invention, what' we claim'is 1. The herein-described process for the manufacture of formaldehyde sulfoxylates, which consists in treating the sulfoxylates of ketones having the. formula CH COX, wherein X means methyl or ethyl, with formaldeiyde. 2. The herein-described process for the "manufacture of formaldehyde sulfoxylates, which consists in treating the sulfoxylates of acetone with formaldehyde.
In testimony that we claim the foregoing as our invention we have signed our names in preseni ze of two subscribing witnesses.
\ UDOLF MULLER.
VVOLDEMAR VVOLLENBERG. Witnesses:
JEAN GRUND,
CAPL GR ND.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30703206A US841999A (en) | 1906-03-20 | 1906-03-20 | Process of making formaldehyde sulfoxylates. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30703206A US841999A (en) | 1906-03-20 | 1906-03-20 | Process of making formaldehyde sulfoxylates. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US841999A true US841999A (en) | 1907-01-22 |
Family
ID=2910470
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US30703206A Expired - Lifetime US841999A (en) | 1906-03-20 | 1906-03-20 | Process of making formaldehyde sulfoxylates. |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US841999A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3248278A (en) * | 1962-02-16 | 1966-04-26 | Pritchard & Co J F | Method of recovering monovalent cations from spent monovalent cation sulfite pulpingliquor |
| US4657593A (en) * | 1981-11-10 | 1987-04-14 | Skw Trostberg Aktiengesellschaft | Modifying surface tension of finely-divided materials in a liquid |
| US4818288A (en) * | 1983-12-07 | 1989-04-04 | Skw Trostberg Aktiengesellschaft | Dispersant for concrete mixtures of high salt content |
-
1906
- 1906-03-20 US US30703206A patent/US841999A/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3248278A (en) * | 1962-02-16 | 1966-04-26 | Pritchard & Co J F | Method of recovering monovalent cations from spent monovalent cation sulfite pulpingliquor |
| US4657593A (en) * | 1981-11-10 | 1987-04-14 | Skw Trostberg Aktiengesellschaft | Modifying surface tension of finely-divided materials in a liquid |
| US4818288A (en) * | 1983-12-07 | 1989-04-04 | Skw Trostberg Aktiengesellschaft | Dispersant for concrete mixtures of high salt content |
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