US2039046A - Nitration of sugars - Google Patents
Nitration of sugars Download PDFInfo
- Publication number
- US2039046A US2039046A US727591A US72759134A US2039046A US 2039046 A US2039046 A US 2039046A US 727591 A US727591 A US 727591A US 72759134 A US72759134 A US 72759134A US 2039046 A US2039046 A US 2039046A
- Authority
- US
- United States
- Prior art keywords
- sugar
- nitrated
- nitration
- sugars
- solvent
- 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
- 235000000346 sugar Nutrition 0.000 title description 22
- 238000006396 nitration reaction Methods 0.000 title description 8
- 150000008163 sugars Chemical class 0.000 title description 6
- 239000002253 acid Substances 0.000 description 12
- 239000000463 material Substances 0.000 description 10
- -1 alkyl nitrates Chemical class 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 230000000802 nitrating effect Effects 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000000746 purification Methods 0.000 description 5
- 239000002360 explosive Substances 0.000 description 4
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 230000000087 stabilizing effect Effects 0.000 description 3
- 229960004793 sucrose Drugs 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- FVHAWXWFPBPFOS-UHFFFAOYSA-N 1,2-dimethyl-3-nitrobenzene Chemical group CC1=CC=CC([N+]([O-])=O)=C1C FVHAWXWFPBPFOS-UHFFFAOYSA-N 0.000 description 2
- ZPTVNYMJQHSSEA-UHFFFAOYSA-N 4-nitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1 ZPTVNYMJQHSSEA-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 230000002950 deficient Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229960002737 fructose Drugs 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 229960001031 glucose Drugs 0.000 description 2
- 229930182470 glycoside Natural products 0.000 description 2
- 150000002338 glycosides Chemical class 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 229960001375 lactose Drugs 0.000 description 2
- RTSODCRZYKSCLO-UHFFFAOYSA-N malic acid monomethyl ester Natural products COC(=O)C(O)CC(O)=O RTSODCRZYKSCLO-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- PVRATXCXJDHJJN-UHFFFAOYSA-N dimethyl 2,3-dihydroxybutanedioate Chemical compound COC(=O)C(O)C(O)C(=O)OC PVRATXCXJDHJJN-UHFFFAOYSA-N 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- ZXQYGBMAQZUVMI-GCMPRSNUSA-N gamma-cyhalothrin Chemical compound CC1(C)[C@@H](\C=C(/Cl)C(F)(F)F)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-GCMPRSNUSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229960003711 glyceryl trinitrate Drugs 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229960002160 maltose Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229940082615 organic nitrates used in cardiac disease Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 239000003799 water insoluble solvent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H11/00—Compounds containing saccharide radicals esterified by inorganic acids; Metal salts thereof
- C07H11/02—Nitrates; Nitrites
Definitions
- My invention relates to improvements in the nitration of sugars, and more particularly relates to improved means for the purification of the products obtained by the nitration of sugars by 5 the action of nitric acid or nitrating acids.
- One of the objects of my invention is to provide means for the purification and stabilization of the gummy and doughy acid products which are obtained as the result of the nitration step.
- Tne nitration of cane sugar and similar sugars dissolved in glycerin, glycol, and other polyhydric alcohols is well known.
- the usual procedure is to dissolve the sugar in the alcohol and to then nitrate the mixture, and up to the present time the difficulties inherent in the nitration of the sugars alone has prevented their commercial preparation, as the physical conditions of the nitrated products have been such as to prevent their purification to a sufficient extent to enable a stable product to be obtained by the methods of purification and stabilization heretofore used.
- I may employ such solvents as mononitrobenzene, mononitrotoluene, mononitroxylene, alkyl nitrates, aliphatic ethers, chlorinated aliphatic ethers, chlorinated paraffins, alkvl carbonates, nitrated esters of hy- 0 droxy acids such as nitrated methyl glycolate, nitrated methyl lactate, nitrated methylmalate, nitrated dimethyltartrate, etc. and in general I may employ in the practice of my invention any material which is combustible and oxygen-deficient and which is insoluble in water and unaffected by dilute spent acid, and which is a solvent for nitrated sugar.
- solvents as mononitrobenzene, mononitrotoluene, mononitroxylene, alkyl nitrates, aliphatic ethers, chlorinated aliphatic ethers, chlorinated paraffins, alkvl carbonates, nit
- the products obtained from the practice of my invention are liquids which are capable of use in the formulation of explosive mixtures as substitutes for the nitrated polyhydric alcohols and in 25 general the products obtained by the practice of my invention may be employed to advantage either directly as liquid explosive materials or indirectly in the preparation of explosive mixtures, in combination with the usual constituents of for- 30 mulated explosives.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
Description
Patented Apr. 28, 1936 UNITED STATES NITRATION F SUGABS Joseph A.
Wyler, Allentown, Pa., assignor to Trojan Powder Company, a corporation of New York No Drawing. Application May 25, 1934, Serial No. 727,591
3 Claims. (01. 52-20) My invention relates to improvements in the nitration of sugars, and more particularly relates to improved means for the purification of the products obtained by the nitration of sugars by 5 the action of nitric acid or nitrating acids. One of the objects of my invention is to provide means for the purification and stabilization of the gummy and doughy acid products which are obtained as the result of the nitration step.
Tne nitration of cane sugar and similar sugars dissolved in glycerin, glycol, and other polyhydric alcohols is well known. In the manufacture of these products the usual procedure is to dissolve the sugar in the alcohol and to then nitrate the mixture, and up to the present time the difficulties inherent in the nitration of the sugars alone has prevented their commercial preparation, as the physical conditions of the nitrated products have been such as to prevent their purification to a sufficient extent to enable a stable product to be obtained by the methods of purification and stabilization heretofore used.
I have discovered that by nitrating a sugar in the usual manner employed in the nitration of other materials, (and without the presence of any solvent fornitrated sugar except the nitrating acids themselves) and thereafter separating the resulting gummy, viscous nitrated sugar layer and admixing it with a suitable solvent for nitrated sugar which is insoluble in water or in the dilute spent acid, it is possible to obtain a solution of the nitrated sugar in condition suitable for further purification.
In the practice of my invention I may employ such solvents as mononitrobenzene, mononitrotoluene, mononitroxylene, alkyl nitrates, aliphatic ethers, chlorinated aliphatic ethers, chlorinated paraffins, alkvl carbonates, nitrated esters of hy- 0 droxy acids such as nitrated methyl glycolate, nitrated methyl lactate, nitrated methylmalate, nitrated dimethyltartrate, etc. and in general I may employ in the practice of my invention any material which is combustible and oxygen-deficient and which is insoluble in water and unaffected by dilute spent acid, and which is a solvent for nitrated sugar. In the above list where I have mentioned the methyl compounds for example, I may also employ the ethyl compounds or the other homologues of the compounds named.
I As an example of my invention, I will describe the process which I prefer to employ in the treatment of a sugar such as cane sugar, glucose, lactose, levulose, and the like. a
55 To parts, by weight, of 98% HZNOa, add. 30
parts, by weight, of sugar, keeping the temperature below 20 C. When all of the sugar has been dissolved, add 300 parts of oleum or strong H2504. This forms either a thick, gummy plastic mass or a. viscous solution in suspension in the spent acid. 5 This suspension is drowned in tap water and stirred a few minutes in order to free alarge portion of its occluded acid. Then add 15 parts of mononitrobenzene and stir. This results in a thin solution of nitrated sugar in the agent added, 10 which can be washed, stabilized and settled, by the methods commonly used in the washing and stabilizing of nitroglycerine and other liquid organic nitrates.
It will of course be recognized that the above 15 is given as an illustration only, and my invention is not to be limited to the specific proportions named. In general, my invention may be applied to the treatment of cane sugar, glucose, levulose, maltose, lactose, etc. as well as any of the glyco- 20 ides derived from these sugars.
The products obtained from the practice of my invention are liquids which are capable of use in the formulation of explosive mixtures as substitutes for the nitrated polyhydric alcohols and in 25 general the products obtained by the practice of my invention may be employed to advantage either directly as liquid explosive materials or indirectly in the preparation of explosive mixtures, in combination with the usual constituents of for- 30 mulated explosives.
It will be evident that many modifications may be made within the. limits of the disclosure as herein made, and accordingly no limitations should be placed upon my invention, except as 35 indicated in the appended claims.
I claim:
1. The process of treating an organic body selected from the group of a sugar and the glycoside 40 of a sugar, which comprises nitrating the material, separating the plastic viscous nitrated material from the spent acid, adding a water-insoluble combustible and oxygen-deficient organic solvent for the nitrated material which solvent is unai- 4,5 iected by dilute spent acid, and thereafter washing and stabilizing the mixture so obtained.
.2. The process of treating an organic body selected from the group of a sugar and the glycoside of a sugar which comprises nitrating the material, 5 separating .the plastic viscous nitrated material from the spent acid, adding a water-insoluble solvent selected from the group of mononitrobenzene, mononitrotoluene, mononitroxylene, alkyl nitrates, aliphatic ethers, chlorinated aliphatic 5 of a sugar which comprises nitrating the material, separating the plastic viscous nitrated material from the spent acid, adding a solvent nitrated ester of an aliphatic hydroxy acid, and
thereafter washing and stabilizing the mixture so 5 obtained.
JOSEPH A. WYLER.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US727591A US2039046A (en) | 1934-05-25 | 1934-05-25 | Nitration of sugars |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US727591A US2039046A (en) | 1934-05-25 | 1934-05-25 | Nitration of sugars |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2039046A true US2039046A (en) | 1936-04-28 |
Family
ID=24923243
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US727591A Expired - Lifetime US2039046A (en) | 1934-05-25 | 1934-05-25 | Nitration of sugars |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2039046A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2921846A (en) * | 1955-02-11 | 1960-01-19 | Midland Chemical Corp | Thickened or gelled normally liquid nitroparaffin propellants |
| US2969354A (en) * | 1957-12-19 | 1961-01-24 | Atlas Powder Co | Aldohexose nitroureide tetranitrate and salts thereof |
| US4195174A (en) * | 1977-04-14 | 1980-03-25 | Chembiomed Ltd. | Synthesis of 2-amino-2-deoxyglycoses and 2-amino-2-deoxyglycosides from glycals |
-
1934
- 1934-05-25 US US727591A patent/US2039046A/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2921846A (en) * | 1955-02-11 | 1960-01-19 | Midland Chemical Corp | Thickened or gelled normally liquid nitroparaffin propellants |
| US2969354A (en) * | 1957-12-19 | 1961-01-24 | Atlas Powder Co | Aldohexose nitroureide tetranitrate and salts thereof |
| US4195174A (en) * | 1977-04-14 | 1980-03-25 | Chembiomed Ltd. | Synthesis of 2-amino-2-deoxyglycoses and 2-amino-2-deoxyglycosides from glycals |
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