DE1518655C3 - Verfahren zur Herstellung von Nitroalkanen - Google Patents

Verfahren zur Herstellung von Nitroalkanen

Info

Publication number: DE1518655C3
Authority: DE; Germany
Prior art keywords: nitric acid; reaction; methane; temperature; acid
Prior art date: 1964-06-22
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

Application number

DE1518655A

Other languages

German (de)

English (en)

Other versions

DE1518655B2 (de

DE1518655A1 (de

Inventor

Richard S. Egly

Emory E. Toops Jun.

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Commercial Solvents Corp Terre Haute Ind (vsta)

Original Assignee

Commercial Solvents Corp Terre Haute Ind (vsta)

Priority date (The priority date 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 date listed.)

1964-06-22

Filing date

1965-06-19

Publication date

1975-09-04

1965-06-19 Application filed by Commercial Solvents Corp Terre Haute Ind (vsta) filed Critical Commercial Solvents Corp Terre Haute Ind (vsta)

1969-02-06 Publication of DE1518655A1 publication Critical patent/DE1518655A1/de

1975-01-09 Publication of DE1518655B2 publication Critical patent/DE1518655B2/de

1975-09-04 Application granted granted Critical

1975-09-04 Publication of DE1518655C3 publication Critical patent/DE1518655C3/de

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 12
125000004971 nitroalkyl group Chemical group 0.000 title claims 4
238000002360 preparation method Methods 0.000 title claims 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 68
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 35
229910017604 nitric acid Inorganic materials 0.000 claims description 34
238000006243 chemical reaction Methods 0.000 claims description 31
239000000047 product Substances 0.000 claims description 12
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 9
239000007789 gas Substances 0.000 claims description 8
238000006396 nitration reaction Methods 0.000 claims description 6
238000010791 quenching Methods 0.000 claims description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
230000015572 biosynthetic process Effects 0.000 claims description 4
230000000171 quenching effect Effects 0.000 claims description 4
238000002347 injection Methods 0.000 claims description 3
239000007924 injection Substances 0.000 claims description 3
238000007086 side reaction Methods 0.000 claims description 3
239000006227 byproduct Substances 0.000 claims description 2
238000002485 combustion reaction Methods 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
239000000203 mixture Substances 0.000 claims description 2
239000011541 reaction mixture Substances 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
150000001335 aliphatic alkanes Chemical class 0.000 claims 8
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 4
239000012071 phase Substances 0.000 claims 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 2
125000004432 carbon atom Chemical group C* 0.000 claims 2
239000003345 natural gas Substances 0.000 claims 2
239000001294 propane Substances 0.000 claims 2
230000035484 reaction time Effects 0.000 claims 2
239000012808 vapor phase Substances 0.000 claims 2
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical class [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 1
206010010774 Constipation Diseases 0.000 claims 1
230000002378 acidificating effect Effects 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
229910002090 carbon oxide Inorganic materials 0.000 claims 1
239000003365 glass fiber Substances 0.000 claims 1
238000005121 nitriding Methods 0.000 claims 1
229910052757 nitrogen Inorganic materials 0.000 claims 1
239000003973 paint Substances 0.000 claims 1
239000000376 reactant Substances 0.000 claims 1
230000004044 response Effects 0.000 claims 1
230000000391 smoking effect Effects 0.000 claims 1
239000007795 chemical reaction product Substances 0.000 description 7
230000000694 effects Effects 0.000 description 4
230000003647 oxidation Effects 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
229910002651 NO3 Inorganic materials 0.000 description 2
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-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
229910052799 carbon Inorganic materials 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
238000011084 recovery Methods 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
230000002411 adverse Effects 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
230000006735 deficit Effects 0.000 description 1
238000009826 distribution Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000000446 fuel Substances 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
LYGJENNIWJXYER-BJUDXGSMSA-N nitromethane Chemical group [11CH3][N+]([O-])=O LYGJENNIWJXYER-BJUDXGSMSA-N 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
230000001331 thermoregulatory effect Effects 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1

Classifications

- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/0006—Controlling or regulating processes
- B01J19/0013—Controlling the temperature of the process
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
- B01J2219/00121—Controlling the temperature by direct heating or cooling
- B01J2219/00123—Controlling the temperature by direct heating or cooling adding a temperature modifying medium to the reactants
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
- B01J2219/00159—Controlling the temperature controlling multiple zones along the direction of flow, e.g. pre-heating and after-cooling
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00162—Controlling or regulating processes controlling the pressure
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00164—Controlling or regulating processes controlling the flow
- B01J2219/00166—Controlling or regulating processes controlling the flow controlling the residence time inside the reactor vessel
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DE1518655A 1964-06-22 1965-06-19 Verfahren zur Herstellung von Nitroalkanen Expired DE1518655C3 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US37686164A	1964-06-22	1964-06-22
US37668164A	1964-06-22	1964-06-22

Publications (3)

Publication Number	Publication Date
DE1518655A1 DE1518655A1 (de)	1969-02-06
DE1518655B2 DE1518655B2 (de)	1975-01-09
DE1518655C3 true DE1518655C3 (de)	1975-09-04

Family

ID=27007503

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE1518655A Expired DE1518655C3 (de)	1964-06-22	1965-06-19	Verfahren zur Herstellung von Nitroalkanen

Country Status (6)

Country	Link
BE (1)	BE665694A (da)
BR (1)	BR6570539D0 (da)
DE (1)	DE1518655C3 (da)
DK (1)	DK120074B (da)
GB (1)	GB1088619A (da)
NL (2)	NL6507757A (da)

0
- NL NL128575D patent/NL128575C/xx active
1965
- 1965-06-17 GB GB25642/65A patent/GB1088619A/en not_active Expired
- 1965-06-17 NL NL6507757A patent/NL6507757A/xx unknown
- 1965-06-19 DE DE1518655A patent/DE1518655C3/de not_active Expired
- 1965-06-21 BE BE665694D patent/BE665694A/xx unknown
- 1965-06-21 BR BR170539/65A patent/BR6570539D0/pt unknown
- 1965-06-21 DK DK312665AA patent/DK120074B/da unknown

Also Published As

Publication number	Publication date
DE1518655B2 (de)	1975-01-09
BR6570539D0 (pt)	1973-12-27
NL6507757A (da)	1965-12-23
DE1518655A1 (de)	1969-02-06
DK120074B (da)	1971-04-05
GB1088619A (en)	1967-10-25
BE665694A (da)	1965-10-18
NL128575C (da)

Legal Events

Date	Code	Title	Description
1975-09-04	C3	Grant after two publication steps (3rd publication)
1977-12-31	E77	Valid patent as to the heymanns-index 1977

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