US3000942A - N,n'-(nitrazaalkyl) oxamides - Google Patents
N,n'-(nitrazaalkyl) oxamides Download PDFInfo
- Publication number
- US3000942A US3000942A US666269A US66626957A US3000942A US 3000942 A US3000942 A US 3000942A US 666269 A US666269 A US 666269A US 66626957 A US66626957 A US 66626957A US 3000942 A US3000942 A US 3000942A
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- US
- United States
- Prior art keywords
- nitraza
- oxamide
- bis
- compounds
- formula
- 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
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- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical class NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 title claims description 17
- 239000000203 mixture Substances 0.000 claims description 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 18
- -1 for example Chemical class 0.000 description 15
- 239000002253 acid Substances 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000002360 explosive Substances 0.000 description 6
- 235000006408 oxalic acid Nutrition 0.000 description 6
- 150000005690 diesters Chemical class 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- 125000003431 oxalo group Chemical group 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- JRMAQQQTXDJDNC-UHFFFAOYSA-M 2-ethoxy-2-oxoacetate Chemical compound CCOC(=O)C([O-])=O JRMAQQQTXDJDNC-UHFFFAOYSA-M 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001540 azides Chemical class 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 150000002431 hydrogen Chemical group 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 235000010005 Catalpa ovata Nutrition 0.000 description 1
- 240000004528 Catalpa ovata Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- MHWLNQBTOIYJJP-UHFFFAOYSA-N mercury difulminate Chemical compound [O-][N+]#C[Hg]C#[N+][O-] MHWLNQBTOIYJJP-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C06—EXPLOSIVES; MATCHES
- C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
- C06B25/00—Compositions containing a nitrated organic compound
Definitions
- the oxarnides of the present invention are particularly valuable as starting materials for preparing high energy oxamide compounds, such as, for example, N,N'-bis (3- nitraza-l-butyl)-N,N'-dinitro oxamide, as more fully disclosed in my copending US. patent application Serial No. 666,270, filed concurrently with the present application.
- the high energy oxamide compounds of the copending application are useful as high explosives, and can be used in any conventional explosive missile, projectile, rocket, or the like, as the main explosive charge.
- any conventional explosive missile, projectile, rocket, or the like as the main explosive charge.
- One Way of using the high explosives of this invention in a device such as that disclosed in United States Patent No. 2,470,162, is to pack the crystalline explosive in powder form into the warhead of the missile. Alternatively, the crystals can be first pelletized and then packed.
- a charge thus prepared is sutliciently insensitive to withstand the shock entailed in the ejection of a shell from a gun barrel or from a rocket launching tube under the pressure de veloped from ignition of a propellant charge, and can be caused to explode on operation of an impactor time fuse-mechanism firing a detonating explosive such as lead azide or mercury fulminate.
- oxamide compounds of this invention are readily prepared by condensing nitraza amines with oxalyl compounds in accordance with the general reaction scheme set forth below:
- Example I Preparation of N,N'-bis (3-nitraza-1- butyl) oxamide To a solution of 11.9 g. (0.1 mole) of 3-nitraza-l-butylamine in 50 ml. of chloroform was added 7.3 (0.05 mole) of ethyl oxalate. An immediate exothermic reaction occurred with the precipitation of a white solid. The solid was collected and dried to produce 9.9 g. (67.8%) of final product having a melting point of 225-230 C.
- Reaction temperature is non-critical in the practice of this invention, the only eliect of temperature variation being a corresponding increase or decrease in reaction rate.
- nitraza amines useful as starting materials in the 3,000,942 Patented Sept. 19, 1961 practice of this invention are generated from their correponding strong mineral acid salt by neutralizing the strong mineral acid salts with inorganic basic salts, as for example hydroxides or carbonates, or weak organic acid salts, such as acetates, of alkali or alkaline earth metals such as sodium, calcium, etc.
- inorganic basic salts as for example hydroxides or carbonates
- weak organic acid salts such as acetates, of alkali or alkaline earth metals such as sodium, calcium, etc.
- the strong mineral acid salts of the nitraza amines are prepared by reacting corresponding nitraza isocyanates, such as 3- nitraza-l-butyl isocyanate, with aqueous strong mineral acid solutions, as more fully disclosed in my copending US. patent application Serial No. 666,273.
- nitraza isocyanates are prepared by reacting nitraza-acid halides, such as 4-nitrazapentanoyl chloride, with alkali or alkaline earth metal azides, as for example sodium azide, to form the corresponding nitraza azides and then heating said nitraza azides under anhydrous conditions to eflect rearrangement to the desired natraza isocyanates.
- nitraza-acid halides such as 4-nitrazapentanoyl chloride
- alkali or alkaline earth metal azides as for example sodium azide
- nitraza-acid halides from which the nitraza isocyanates are prepared are obtained by reacting thionyl halides, such as thionyl chloride, with appropriate nitrazaacids, as more fully disclosed in my copending US. patent application Serial No. 514,384.
- the nitraza-acids can be nitroalkyl-aza-acids which are prepared by condensing nitroalcohols with amino acids, as more fully disclosed in assignees copending US. patent application Serial No. 416,385, filed March 15, 1954, or alkylnitraza-acids which are prepared by the acid hydrolysis of nitraza-nitriles, as disclosed in my copending US. patent application Serial No. 514,386, filed June 9, 1955.
- mixtures of suitable nitraza amines can be employed in the preparation of the oxamide compounds of this invention. It is thus within the purview of the invention to condense such mixtures of nitraza amines with suitable oxalyl compounds and thereby obtain oxamide compounds of the general formula shown hereinbefore in which the two Rs and/or the two As are respectively different. For reasons of convenience and economy, however, I prefer to employ relatively pure nitraza amines as starting materials, in which case symmetrical oxamide compounds having identical Rs and identical As are produced.
- the oxalyl compounds used as starting materials in the practice of the present invention can be acyl dihalides of oxalic acid, as for example, oxalyl chloride, or diesters of oxalic acid, as for example ethyl oxalate.
- oxalyl chloride diesters of oxalic acid, as for example ethyl oxalate.
- diesters of oxalic acid rather than the dihalides of oxalic acid, for purposes of my invention since when the former compounds are used alcohols are formed as by-products whereas when the latter compounds are used halogen acids are formed as by-products.
- the presence of the aforesaid alcohols has substantially no effect on the reaction of my invention but the presence of halogen acids interferes with the reaction since they form salts with the nitraza amine reactants present.
- Diesters of oxalic acid other than ethyl oxalate are suitable for the practice of my invention.
- diesters prepared from the lower alcohols, such as methyl, n-propyl, n-butyl, etc., alcohol can be employed within the scope of the invention.
- oxamide compounds can be prepared in accordance with the method of my invention.
- 4-nitraza-1-hexyl amine and 3-aza-3,5,5-t:rinitro-l-hexylamine react with diesters of oxalic acid and the lower alcohols to yield N,N'-bis (4-nitraza-1-hexyl) oxamide and N,N-bis (3- aza-3,5,5-trinitro-l-hexyl) oxamide, respectively.
- Other members of this new series of oxamide compounds are prepared simply by reacting appropriate starting materials as taught herein.
- R-CH21IA-CHFNC ONCHT'-A'AICHZR wherein each R is a radical selected from the group consisting of hydrogen, lower alkyl, and lower nitroalkyl radicals and each A is a lower alkylene radical.
- N,N'-bis (3-aza- 3,5,5-trinitrohexyl) oxarnide having the structural formula:
- the method of preparing N,N'-bis (nitrazaalkyl) oxarnides having the formula:
- each R is a radical selected from the group consisting of hydrogen, lower alkyl, and lower nitroalkyl radicals; each A is a lower alkylene radical; and each R is a radical selected from the group consisting of halogen and alkoxy radicals.
- each R is a lower nitroalkyl radical and each R is an alkoxy radical.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
United States Patent 3,000,942 N,N'- AALKYL) OXAMIDES Milton B. Frankel, Pasadena, Calif., assignor to Aerojet- General Corporation, Azusa, Califl, a corporation of Ohio No Drawing. Filed June 13, 1957, Ser. No. 666,269 12 Claims. (Cl. 260-561) This invention relates to new compositions of matter and to their preparation. In particular, the invention relates to N,N'-bis (nitrazaalkyl) oxamides having the general formula:
N O: H O O H blloz R-CHr-l I-ACHz-Ik-ii-ik-IL-GIh-A-N-Cflr-R wherein each R is a hydrogen, alkyl, or nitroalkyl radical and each A is an alkylene radical.
The oxarnides of the present invention are particularly valuable as starting materials for preparing high energy oxamide compounds, such as, for example, N,N'-bis (3- nitraza-l-butyl)-N,N'-dinitro oxamide, as more fully disclosed in my copending US. patent application Serial No. 666,270, filed concurrently with the present application.
The high energy oxamide compounds of the copending application are useful as high explosives, and can be used in any conventional explosive missile, projectile, rocket, or the like, as the main explosive charge. .An example of such a missile is disclosed in United States Patent No. 2,470,162, issued May 17, 1949. One Way of using the high explosives of this invention in a device such as that disclosed in United States Patent No. 2,470,162, is to pack the crystalline explosive in powder form into the warhead of the missile. Alternatively, the crystals can be first pelletized and then packed. A charge thus prepared is sutliciently insensitive to withstand the shock entailed in the ejection of a shell from a gun barrel or from a rocket launching tube under the pressure de veloped from ignition of a propellant charge, and can be caused to explode on operation of an impactor time fuse-mechanism firing a detonating explosive such as lead azide or mercury fulminate.
The oxamide compounds of this invention are readily prepared by condensing nitraza amines with oxalyl compounds in accordance with the general reaction scheme set forth below:
N0: 2R-OH,-IiT-ACH -NH,+R'-ii-ii-1t' N01 H O O H IIIOQ R-CH I IACHr-I I I ICHz-ANOH2-R wherein each R and each A is as previously defined and each R is a halogen or alkoxy radical.
To more clearly illustrate my invention, the following example is presented. It is to be understood, however, that this example is intended merely as a means of illustrating my invention and that it should not be construed as limiting the scope of said invention in any way.
Example I.Preparation of N,N'-bis (3-nitraza-1- butyl) oxamide To a solution of 11.9 g. (0.1 mole) of 3-nitraza-l-butylamine in 50 ml. of chloroform was added 7.3 (0.05 mole) of ethyl oxalate. An immediate exothermic reaction occurred with the precipitation of a white solid. The solid was collected and dried to produce 9.9 g. (67.8%) of final product having a melting point of 225-230 C.
Reaction temperature is non-critical in the practice of this invention, the only eliect of temperature variation being a corresponding increase or decrease in reaction rate.
The nitraza amines useful as starting materials in the 3,000,942 Patented Sept. 19, 1961 practice of this invention are generated from their correponding strong mineral acid salt by neutralizing the strong mineral acid salts with inorganic basic salts, as for example hydroxides or carbonates, or weak organic acid salts, such as acetates, of alkali or alkaline earth metals such as sodium, calcium, etc. This method of generating ditraza amines from their strong mineral acid, i.e., hydrochloric acid, nitric acid, or the like, salts is more fully disclosed in my copending US. patent application Serial No. 666,273, filed concurrently with the present application.
The strong mineral acid salts of the nitraza amines, suitable for use in the present invention, are prepared by reacting corresponding nitraza isocyanates, such as 3- nitraza-l-butyl isocyanate, with aqueous strong mineral acid solutions, as more fully disclosed in my copending US. patent application Serial No. 666,273.
The above-mentioned nitraza isocyanates are prepared by reacting nitraza-acid halides, such as 4-nitrazapentanoyl chloride, with alkali or alkaline earth metal azides, as for example sodium azide, to form the corresponding nitraza azides and then heating said nitraza azides under anhydrous conditions to eflect rearrangement to the desired natraza isocyanates. This method of preparing nitraza isocyanates is more fully disclosed in my copending US. patent application Serial No. 514,384, filed June 9, 1955.
The nitraza-acid halides from which the nitraza isocyanates are prepared are obtained by reacting thionyl halides, such as thionyl chloride, with appropriate nitrazaacids, as more fully disclosed in my copending US. patent application Serial No. 514,384. The nitraza-acids can be nitroalkyl-aza-acids which are prepared by condensing nitroalcohols with amino acids, as more fully disclosed in assignees copending US. patent application Serial No. 416,385, filed March 15, 1954, or alkylnitraza-acids which are prepared by the acid hydrolysis of nitraza-nitriles, as disclosed in my copending US. patent application Serial No. 514,386, filed June 9, 1955.
It should be pointed out that mixtures of suitable nitraza amines can be employed in the preparation of the oxamide compounds of this invention. It is thus within the purview of the invention to condense such mixtures of nitraza amines with suitable oxalyl compounds and thereby obtain oxamide compounds of the general formula shown hereinbefore in which the two Rs and/or the two As are respectively different. For reasons of convenience and economy, however, I prefer to employ relatively pure nitraza amines as starting materials, in which case symmetrical oxamide compounds having identical Rs and identical As are produced.
The oxalyl compounds used as starting materials in the practice of the present invention can be acyl dihalides of oxalic acid, as for example, oxalyl chloride, or diesters of oxalic acid, as for example ethyl oxalate. I prefer to employ the diesters of oxalic acid, rather than the dihalides of oxalic acid, for purposes of my invention since when the former compounds are used alcohols are formed as by-products whereas when the latter compounds are used halogen acids are formed as by-products. The presence of the aforesaid alcohols has substantially no effect on the reaction of my invention but the presence of halogen acids interferes with the reaction since they form salts with the nitraza amine reactants present.
Diesters of oxalic acid other than ethyl oxalate are suitable for the practice of my invention. For example, diesters prepared from the lower alcohols, such as methyl, n-propyl, n-butyl, etc., alcohol, can be employed within the scope of the invention.
It will be appreciataed that a wide variety of oxamide compounds can be prepared in accordance with the method of my invention. For example, 4-nitraza-1-hexyl amine and 3-aza-3,5,5-t:rinitro-l-hexylamine react with diesters of oxalic acid and the lower alcohols to yield N,N'-bis (4-nitraza-1-hexyl) oxamide and N,N-bis (3- aza-3,5,5-trinitro-l-hexyl) oxamide, respectively. Other members of this new series of oxamide compounds are prepared simply by reacting appropriate starting materials as taught herein.
I claim:
1. As a new composition of matter, an N,N'-bis (nitrazaalkyl) oxamide having the formula:
N; Ill (I) (1? 1'1 NO:
R-CH21IA-CHFNC ONCHT'-A'AICHZR wherein each R is a radical selected from the group consisting of hydrogen, lower alkyl, and lower nitroalkyl radicals and each A is a lower alkylene radical.
2. As a new composition of matter, an N,N'-bis (nitrazaalkyl) oxamide having the formula:
6. As a new composition of matter, N,N'-bis (3-aza- 3,5,5-trinitrohexyl) oxarnide having the structural formula:
N05 NO: NO: NO; l l I ll il I l l CHg- CH2N-CH:CHrN-O -NCHzCH9-NCH5 -CH| 7. The method of preparing N,N'-bis (nitrazaalkyl) oxarnides having the formula:
which comprises condensing nitraza amines having the formula:
RCHgNA-GHr-NH with oxalyl compounds having the formula:
wherein each R is a radical selected from the group consisting of hydrogen, lower alkyl, and lower nitroalkyl radicals; each A is a lower alkylene radical; and each R is a radical selected from the group consisting of halogen and alkoxy radicals.
8. The method of preparing N,N'-bis (nitrazaalkyl) oxamides having the formula:
which comprises condensing nitraza amines having the formula:
RN-AC H|'NH| with oxalyl compounds having the formula:
R'c-ti-R' wherein each R is a lower alkyl radical; each A is a lower alkylene radical; and each R is an alkoxy radical.
9. The method of claim 7 wherein each R is a lower nitroalkyl radical and each R is an alkoxy radical.
10. The method of preparing N,N'-bis (El-nitraza-butyl} oxamide which comprises condensing 3-nitraza-1- butylamine with ethyl oxalate.
11. The method of preparing N,N'-bis (4-nitraza-1- hexyl) oxamide which comprises condensing 4-nitraza-lhexylarnine with an oxalyl compound having the formula:
I ll R -(l-G-R wherein each R is a lower alkoxy radical.
12. The method of preparing N,N-bis (3-aza-3,5,5- trinitro-l-hexyl) oxamide which comprises condensing g3-aza-3,5,5-trinitro-l-l1exylamine with an oxalyl compound having the formula:
0 0 H II R-CCR' wherein each R is a lower alkoxy radical.
No references cited.
Claims (1)
1. AS A NEW COMPOSITION OF MATTER, AN N,N''-BIS (NITRAZAALKYL) OXAMIDE HAVING THE FORMULA:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US666269A US3000942A (en) | 1957-06-13 | 1957-06-13 | N,n'-(nitrazaalkyl) oxamides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US666269A US3000942A (en) | 1957-06-13 | 1957-06-13 | N,n'-(nitrazaalkyl) oxamides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3000942A true US3000942A (en) | 1961-09-19 |
Family
ID=24673512
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US666269A Expired - Lifetime US3000942A (en) | 1957-06-13 | 1957-06-13 | N,n'-(nitrazaalkyl) oxamides |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3000942A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090050535A1 (en) * | 2007-05-18 | 2009-02-26 | Wayne Errol Evans | Reactor system, and a process for preparing an olefin oxide, a 1,2-diol, a 1,2-diol ether, a 1,2-carbonate and an alkanolamine |
| US20090286998A1 (en) * | 2008-05-15 | 2009-11-19 | Wayne Errol Evans | Process for the preparation of alkylene carbonate and/or alkylene glycol |
| US20090287011A1 (en) * | 2008-05-15 | 2009-11-19 | Wayne Errol Evans | Process for the preparation of an alkylene carbonate and an alkylene glycol |
| US8569527B2 (en) | 2007-05-18 | 2013-10-29 | Shell Oil Company | Reactor system, an absorbent and a process for reacting a feed |
| US9144765B2 (en) | 2007-05-18 | 2015-09-29 | Shell Oil Company | Reactor system, an absorbent and a process for reacting a feed |
-
1957
- 1957-06-13 US US666269A patent/US3000942A/en not_active Expired - Lifetime
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090050535A1 (en) * | 2007-05-18 | 2009-02-26 | Wayne Errol Evans | Reactor system, and a process for preparing an olefin oxide, a 1,2-diol, a 1,2-diol ether, a 1,2-carbonate and an alkanolamine |
| US8569527B2 (en) | 2007-05-18 | 2013-10-29 | Shell Oil Company | Reactor system, an absorbent and a process for reacting a feed |
| US9144765B2 (en) | 2007-05-18 | 2015-09-29 | Shell Oil Company | Reactor system, an absorbent and a process for reacting a feed |
| US20090286998A1 (en) * | 2008-05-15 | 2009-11-19 | Wayne Errol Evans | Process for the preparation of alkylene carbonate and/or alkylene glycol |
| US20090287011A1 (en) * | 2008-05-15 | 2009-11-19 | Wayne Errol Evans | Process for the preparation of an alkylene carbonate and an alkylene glycol |
| US8193374B2 (en) | 2008-05-15 | 2012-06-05 | Shell Oil Company | Process for the preparation of alkylene carbonate and/or alkylene glycol |
| US8273912B2 (en) | 2008-05-15 | 2012-09-25 | Shell Oil Company | Process for the preparation of an alkylene carbonate and an alkylene glycol |
| US8858893B2 (en) | 2008-05-15 | 2014-10-14 | Shell Oil Company | Process for the preparation of an alkylene carbonate and an alkylene glycol |
| US9527787B2 (en) | 2008-05-15 | 2016-12-27 | Shell Oil Company | Process for the preparation of alkylene carbonate and/or alkylene glycol |
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