CN105330551B - A kind of method for preventing N methylanilines from changing colour - Google Patents
A kind of method for preventing N methylanilines from changing colour Download PDFInfo
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- CN105330551B CN105330551B CN201510915379.3A CN201510915379A CN105330551B CN 105330551 B CN105330551 B CN 105330551B CN 201510915379 A CN201510915379 A CN 201510915379A CN 105330551 B CN105330551 B CN 105330551B
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- alkyl
- combination
- heterocyclylalkyl
- compound
- cyclopropylamine
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- 238000000034 method Methods 0.000 title claims abstract description 17
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical class CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 title claims abstract description 16
- -1 alkyl amine compound Chemical class 0.000 claims abstract description 36
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Natural products C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims abstract description 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 5
- VEBLEROFGPOMPB-UHFFFAOYSA-N n-methylcyclopropanamine Chemical compound CNC1CC1 VEBLEROFGPOMPB-UHFFFAOYSA-N 0.000 claims description 5
- KLMZKZJCMDOKFE-UHFFFAOYSA-N 1-octylimidazole Chemical class CCCCCCCCN1C=CN=C1 KLMZKZJCMDOKFE-UHFFFAOYSA-N 0.000 claims description 3
- AMQKPABOPFXDQM-UHFFFAOYSA-N 1-tert-butylimidazole Chemical class CC(C)(C)N1C=CN=C1 AMQKPABOPFXDQM-UHFFFAOYSA-N 0.000 claims description 3
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 claims description 3
- PFYPDUUXDADWKC-UHFFFAOYSA-N 2-propan-2-ylpyridine Chemical class CC(C)C1=CC=CC=N1 PFYPDUUXDADWKC-UHFFFAOYSA-N 0.000 claims description 2
- GIMBKDZNMKTZMG-UHFFFAOYSA-N Isopropylpyrazine Chemical class CC(C)C1=CN=CC=N1 GIMBKDZNMKTZMG-UHFFFAOYSA-N 0.000 claims description 2
- 150000003222 pyridines Chemical class 0.000 claims description 2
- 150000002460 imidazoles Chemical class 0.000 claims 1
- 150000003233 pyrroles Chemical class 0.000 claims 1
- 238000002845 discoloration Methods 0.000 abstract description 4
- 230000009286 beneficial effect Effects 0.000 abstract description 3
- MFEIKQPHQINPRI-UHFFFAOYSA-N 3-Ethylpyridine Chemical compound CCC1=CC=CN=C1 MFEIKQPHQINPRI-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 3
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- KVFIJIWMDBAGDP-UHFFFAOYSA-N ethylpyrazine Chemical class CCC1=CN=CC=N1 KVFIJIWMDBAGDP-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- OHQOKJPHNPUMLN-UHFFFAOYSA-N n,n'-diphenylmethanediamine Chemical class C=1C=CC=CC=1NCNC1=CC=CC=C1 OHQOKJPHNPUMLN-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical class CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 description 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical class CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
- KNDUGOWIKQAXHL-UHFFFAOYSA-N 1-propan-2-ylpyrrole Chemical class CC(C)N1C=CC=C1 KNDUGOWIKQAXHL-UHFFFAOYSA-N 0.000 description 1
- QUYPSOKUBYENRV-UHFFFAOYSA-N 1h-pyrazole;pyridine Chemical class C=1C=NNC=1.C1=CC=NC=C1 QUYPSOKUBYENRV-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000686 essence Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- CAWHJQAVHZEVTJ-UHFFFAOYSA-N methylpyrazine Chemical class CC1=CN=CC=N1 CAWHJQAVHZEVTJ-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 229910001753 sapphirine Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/90—Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Developing Agents For Electrophotography (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
The invention discloses a kind of method for preventing N methylanilines from changing colour, it is characterised in that：Heterocyclylalkyl aminated compounds is added into N methylanilines, the Heterocyclylalkyl aminated compounds is ternary, quaternary, five yuan, hexa-atomic alkyl amine compound, including alkyl cyclopropylamine, alkyl pyrroles, alkyl imidazole, alkyl pyridine, alkyl pyrazine, the beneficial effects of the present invention are：Substantially improve the discoloration problem of N methylanilines.
Description
Technical field
Preapred for an unfavorable turn of events color method the present invention relates to a kind of chemistry, particularly a kind of method for preventing methylphenylamine from changing colour.
Background technology
Methylphenylamine is the important intermediate in the Chemical Manufactures such as agricultural chemicals, dyestuff, medicine, rubber, and purposes is quite varied.
It by aniline and methanol under catalyst gas phase reaction and obtain.But methylphenylamine is not easy to maintain, usually given birth to because of oxidation
Various dark compounds are produced, cause product not meet in quality standard " outward appearance " this basic and important index request and shadow
Sale is rung, how also the synthesis of subsequent product can be badly influenced sometimes due to over oxidation is rotten and can not use
The outward appearance for keeping product original more and more draws attention.
Chinese invention patent CN1906151A discloses a kind of method for preventing discoloration of methylene-bisaniline compounds, uses
Organic phosphine compound of the addition selected from phosphine, phosphite ester and phosphate, methylene-bisaniline compounds nondiscolouring.But in N- first
Organic phosphine compound, nondiscolouring in first day are added in base aniline, but after three days, color is changed into brown, over time,
Color is by brown-brown-russet-black.Seal approach is also taken to avoid contact with air and make moist, using dark color or every light
Packaging, reduces illumination and heated；It is general to be packed using metal bucket, polybag etc., the indifferent gas such as nitrogen are filled with if necessary
Body, it is to avoid phenomenon just oxidized occurs before finished product output.Methylphenylamine nitrogen filled protection after three days color also gradually become
It is deep.
Accordingly, it would be desirable to which the problem of changing colour to methylphenylamine solves.
The content of the invention
The goal of the invention of the present invention is：Prevent what methylphenylamine from changing colour there is provided a kind of for above-mentioned problem
Method.
The technical solution adopted by the present invention is such：
A kind of method for preventing methylphenylamine from changing colour, it is characterised in that：Heterocyclylalkyl amine is added into methylphenylamine
Class compound.
Further, the Heterocyclylalkyl aminated compounds be ternary, quaternary, five yuan, hexa-atomic alkyl amine compound or its
Combination.
Further, the Heterocyclylalkyl aminated compounds is：Alkyl cyclopropylamine, alkyl pyrroles, alkyl imidazole, alkylated pyrazole
Pyridine, alkyl pyrazine or its combination.
Further, the alkyl cyclopropylamine compound is：N- methyl cyclopropylamine, N- ethyls cyclopropylamine or its combination.
Further, the alkyl azole compounds are：N- methylpyrroles, N- N-ethyl pyrrole Ns, N- octyl groups pyrroles, N- isopropyls
Pyrroles or its combination.
Further, the alkyl imidazole compound is：N- methylimidazoles, N- ethyl imidazol(e)s, N- octylimidazoles, N- isopropyls
Imidazoles, N- t-butyl imidazoles or its combination.
Further, the alkyl pyridinium compounds are：2- picolines, 3-ethylpyridine, 4- n-heptyls pyridine, 2- isopropyls
Yl pyridines, 2- tert .-butylpyridines or its combination.
Further, the alkyl pyrazine compound is：2- methylpyrazines, 3- ethyl pyrazines, 2- n-pentyls pyrazine, 3- isopropyls
Base pyrazine, 2- tert-butyl-pyrazins or its combination.
Further, the addition of the Heterocyclylalkyl aminated compounds is 100-5000ppm.
Further, the addition of the Heterocyclylalkyl aminated compounds is 500-1000ppm.
In summary, by adopting the above-described technical solution, the beneficial effects of the invention are as follows：
1st, the colourshifting process of methylphenylamine is slow down significantly, improves the quality of product.
Embodiment
With reference to subordinate list, the present invention is described in detail.
In order to make the purpose , technical scheme and advantage of the present invention be clearer, it is right below in conjunction with subordinate list and embodiment
The present invention is further elaborated.It should be appreciated that the specific embodiments described herein are merely illustrative of the present invention, and
It is not used in the restriction present invention.
Embodiment 1：
100ml methylphenylamines are added in volumetric flask, 1000ppm N- methyl cyclopropylamines is added, stoppers bottle cap, are placed
72 hours, 120 hours, 240 hours, determine its discoloration respectively using chromascope, and with no addition N- methyl cyclopropylamines
Compare, its chromatic value L, a, b are measured using U.S.'s HunterLab chromascopes, as a result take the average value of three measurements.Before measure
The situation of change of color, represents that testing result is shown in Table 1 with L* values and a* values afterwards：
Table (one)
Embodiment 2：
By anti-toner N- methyl cyclopropylamine, N- ethyls cyclopropylamine, N- methylpyrroles, N- N-ethyl pyrrole Ns, N- octyl groups pyrroles, N-
Isopropyl pyrroles, N- methylimidazoles, N- ethyl imidazol(e)s, N- octylimidazoles, N- isopropylimdazoles, N- t-butyl imidazoles, 2- methyl
Pyridine, 3-ethylpyridine, 4- n-heptyls pyridine, 2- isopropyl pyridines, 2- tert .-butylpyridines, 2- methylpyrazines, 3- ethyl pyrazines,
2- n-pentyls pyrazine, 3- isopropylpyrazines, 2- tert-butyl-pyrazins respectively with 100ppm, 500ppm, 800ppm, 1000ppm,
2000ppm, 3000ppm, 5000ppm are separately added into methylphenylamine, are placed 240 hours, using national standard<Uniform color is empty
Between and colour difference formula>(GB7921-87) CIE1976LAB systems, Lab color model is made up of three key elements, and a key element is bright
Spend (L), a and b are two Color Channels.The color that a includes be from bottle green (low brightness values) to grey (middle brightness value) again to
Bright pink (high luminance values)；B is again to yellow (high luminance values) from sapphirine (low brightness values) to grey (middle brightness value).It is real
Test and its chromatic value L, a, b are measured using U.S.'s HunterLab chromascopes, as a result take the average value of three measurements.Face before and after determining
The situation of change of color, is represented with L* values and a* values, such as following table：
Table (two)
The beneficial effect of the present embodiment is：Found by contrasting, after with the addition of corresponding resistance toner, N- methylbenzenes
The process of the discoloration of amine greatly slows down, and general naked eyes all are difficult to out, improve the quality of finished product.
The foregoing is merely illustrative of the preferred embodiments of the present invention, is not intended to limit the invention, all essences in the present invention
Any modifications, equivalent substitutions and improvements made within refreshing and principle etc., should be included in the scope of the protection.
Claims (7)
1. a kind of method for preventing methylphenylamine from changing colour, it is characterised in that：Heterocyclylalkyl amine is added into methylphenylamine
Compound, the Heterocyclylalkyl aminated compounds be ternary, quaternary, five yuan, hexa-atomic alkyl amine compound or its combination, it is described
Heterocyclylalkyl aminated compounds is：Alkyl cyclopropylamine, alkyl pyrroles, alkyl imidazole, alkyl pyridine, alkyl pyrazine or its combination,
The alkyl cyclopropylamine compound is：N- methyl cyclopropylamine, N- ethyls cyclopropylamine or its combination.
2. according to the method described in claim 1, it is characterised in that：The alkyl azole compounds are：N- methylpyrroles, N- second
Base pyrroles, N- octyl groups pyrroles, N- isopropyls pyrroles or its combination.
3. according to the method described in claim 1, it is characterised in that：The alkyl imidazole compound is：N- methylimidazoles, N- second
Base imidazoles, N- octylimidazoles, N- isopropylimdazoles, N- t-butyl imidazoles or its combination.
4. according to the method described in claim 1, it is characterised in that：The alkyl pyridinium compounds are：2- picolines, 3- second
Yl pyridines, 4- n-heptyls pyridine, 2- isopropyl pyridines, 2- tert .-butylpyridines or its combination.
5. according to the method described in claim 1, it is characterised in that：The alkyl pyrazine compound is：2- methylpyrazines, 3- second
Base pyrazine, 2- n-pentyls pyrazine, 3- isopropylpyrazines, 2- tert-butyl-pyrazins or its combination.
6. according to the method described in claim 1, it is characterised in that：The addition of the Heterocyclylalkyl aminated compounds is 100-
5000ppm。
7. method according to claim 6, it is characterised in that：The addition of the Heterocyclylalkyl aminated compounds is 500-
1000ppm。
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510915379.3A CN105330551B (en) | 2015-12-10 | 2015-12-10 | A kind of method for preventing N methylanilines from changing colour |
Applications Claiming Priority (1)
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|---|---|---|---|
| CN201510915379.3A CN105330551B (en) | 2015-12-10 | 2015-12-10 | A kind of method for preventing N methylanilines from changing colour |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105330551A CN105330551A (en) | 2016-02-17 |
| CN105330551B true CN105330551B (en) | 2017-09-29 |
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| CN (1) | CN105330551B (en) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3359315A (en) * | 1964-10-15 | 1967-12-19 | Du Pont | Reduction of aromatic nitro compounds to aromatic amines |
| CA1264475A (en) * | 1985-09-16 | 1990-01-16 | Charles F. Weidig | Discoloration inhibitors for aromatic amines |
| JP2771011B2 (en) * | 1990-04-03 | 1998-07-02 | 三井化学株式会社 | Method for stabilizing aromatic amine |
| JP4459612B2 (en) * | 2003-12-25 | 2010-04-28 | イハラケミカル工業株式会社 | Method for preventing discoloration of methylenebisaniline compound |
| JP5536904B2 (en) * | 2009-12-29 | 2014-07-02 | コーロン インダストリーズ インク | Aromatic diamine and method for producing the same, aramid fiber and method for producing the same |
| CN105037178B (en) * | 2015-06-26 | 2017-04-12 | 沈阳化工研究院有限公司 | Complex antioxidant composition for preventing aromatic amine from discoloring |
-
2015
- 2015-12-10 CN CN201510915379.3A patent/CN105330551B/en active Active
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| Publication number | Publication date |
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| CN105330551A (en) | 2016-02-17 |
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Address after: No. 1 Weihua Road, Xinbei District, Changzhou City, Jiangsu Province, 213127 Patentee after: Jiangsu Jingying New Materials Co.,Ltd. Address before: No. 1 Weihua Road, Xinbei District, Changzhou City, Jiangsu Province, 213127 Patentee before: Jiangsu Jingying Chemical New Materials Co.,Ltd. |
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