CN1189445C - Method for refining 4-amino diphenylamine - Google Patents
Method for refining 4-amino diphenylamine Download PDFInfo
- Publication number
- CN1189445C CN1189445C CNB031481965A CN03148196A CN1189445C CN 1189445 C CN1189445 C CN 1189445C CN B031481965 A CNB031481965 A CN B031481965A CN 03148196 A CN03148196 A CN 03148196A CN 1189445 C CN1189445 C CN 1189445C
- Authority
- CN
- China
- Prior art keywords
- tower
- refining
- still
- aminodiphenylamine
- temperature
- 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.)
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- ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 title claims abstract description 41
- 238000000034 method Methods 0.000 title claims abstract description 26
- 238000007670 refining Methods 0.000 title claims abstract description 15
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 46
- 239000007788 liquid Substances 0.000 claims abstract description 15
- 238000000998 batch distillation Methods 0.000 claims abstract description 11
- 241000282326 Felis catus Species 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 12
- 238000010992 reflux Methods 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 239000012043 crude product Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000006200 vaporizer Substances 0.000 claims description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 abstract 1
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 abstract 1
- 238000002844 melting Methods 0.000 abstract 1
- 230000008018 melting Effects 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- 239000000047 product Substances 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 238000004821 distillation Methods 0.000 description 8
- 238000007599 discharging Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 238000011084 recovery Methods 0.000 description 4
- 238000001577 simple distillation Methods 0.000 description 4
- 238000004939 coking Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000009825 accumulation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- -1 azophenlyene Chemical compound 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 239000002893 slag Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a method for refining 4-amino diphenylamine through continuous rectification and batch distillation in three towers, which comprises: coarse products of 4-amino diphenylamine are obtained through rectification in an NO. 1 tower, and aniline, phenoxazine, azobenzene, etc. are obtained on the tower top; the coarse products are purified in an NO. 2 tower, aniline is separated in an NO. 3 tower, and 4-amino diphenylamine prepared by the batch distillation of residual liquid of the No. 2 tower in a batch kettle returns to the No. 2 tower. Certain technical processes are controlled to effectively refine raw material liquid. The melting point of finished products is higher than 71 DEG C, the 4-amino diphenylamine content of finished products is high than 99 wt%, and the yield of the whole technical process is enhanced to 99% from 94%. Simultaneously, aniline is recovered and utilized.
Description
Technical field
The present invention relates to a kind of method of refining 4-amino pentanoic, relate in particular to the method that adopts three-tower rectification and batch distillation refining 4-amino pentanoic.
Background technology
The 4-aminodiphenylamine is the important intermediate compound of rubber antioxidant, and its quality has directly influenced the quality of derived product.The method of existing distillation 4-aminodiphenylamine generally is to take simple distillation, its vacuum tightness 0.095MPa, the still temperature is at 280 ℃-330 ℃, the top temperature is at 220 ℃-240 ℃, add heating of thermal recovery stack gas or far-infrared heating, adopt this method in the simple distillation later stage, still Wen Gaoda is more than 300 ℃, in still, form a large amount of cokings simultaneously, cause the product yield and the downgrade of 4-aminodiphenylamine; Simultaneously, adopt simple distillation, less because of theoretical plate number, separating effect is often undesirable.In addition, also wayward because of reflux ratio, product content is about 95%, between about 69 ℃-70 ℃ of the fusing point of 4-aminodiphenylamine, has hindered the further raising of 4-aminodiphenylamine quality.
Employing is a feedstock production 4-aminodiphenylamine with oil of mirbane and aniline, contains 4-aminodiphenylamine, aniline and azophenlyene, nitrogen benzide etc. in the stock liquid.As adopt the method for simple distillation, be difficult to above-mentioned each component distillation is separated; If adopt two column distillations, then aniline, azophenlyene and three kinds of materials of nitrogen benzide are in the discharging of front-end volatiles column overhead, the 4-aminodiphenylamine is in the discharging of tower still, then the 4-aminodiphenylamine is continuously fed into the product tower, the 4-aminodiphenylamine is in the cat head discharging, remaining material is drained at the tower still, this technical process is owing to contain azophenlyene and two kinds of materials of nitrogen benzide in the aniline of product column overhead discharging, aniline a large amount of in the product cat head can not be applied mechanically and get back to preceding operation, therefore aniline can not be used by recovery set, cause the wasting of resources, production cost increases.
Summary of the invention
Technical problem to be solved by this invention provide a kind of can recovery set aniline, improve the method for the refining 4-amino pentanoic of the quality of 4-aminodiphenylamine and yield simultaneously.
The method of refining 4-amino pentanoic of the present invention is the method that adopts three tower continuous rectifications and batch distillation.Wherein No. 1 rectifying tower separates feed liquid, and the tower still obtains crude product 4-aminodiphenylamine, and cat head obtains materials such as aniline, azophenlyene, nitrogen benzide, and No. 2 rectifying tower are used for purifying raw 4-aminodiphenylamine, and No. 3 rectifying tower is used for separating aniline.The laggard distillation of in the ranks having a rest of tower bottoms accumulation of No. 2 rectifying tower, what distillation was remaining is the 4-aminodiphenylamine, and the 4-aminodiphenylamine that steams is applied mechanically back No. 2 towers purify.
Concrete treating process of the present invention is as follows: feed liquid is gone in No. 1 rectifying tower by pump delivery, cat head discharging aniline, azophenlyene and nitrogen benzide, the discharging of tower still is a crude product 4-aminodiphenylamine, the cat head discharging of No. 1 rectifying tower enters in No. 3 rectifying tower, No. 3 the rectifying tower cat head steams aniline, its content is 99%, operation before can directly applying mechanically back, remaining azophenlyene of tower still and nitrogen benzide.No. 1 rectifying tower tower bottoms is by pump delivery to 2 tower, No. 2 the rectifying tower cat head distills out finished product 4-aminodiphenylamine, tower still feed liquid runs up to a certain amount of, enter the batch still distillation, distill out remaining a spot of 4-aminodiphenylamine in the feed liquid, eject material from still and return rectifying tower No. 2, other material slag is emitted at the bottom of by still.
The vacuum tightness of No. 1 rectifying tower is 0.09-0.098 (MPa), and reflux ratio is 2: 1-10: 1, tower top temperature be 80-130 (℃), tower still temperature be 260-290 (℃); The vacuum tightness of No. 2 rectifying tower is 0.09-0.098 (MPa), and reflux ratio is 1: 0.5-1: 4, tower top temperature be 140-190 (℃), tower still temperature be 260-300 (℃); The vacuum tightness of No. 3 rectifying tower is 0.09-0.098 (MPa), and reflux ratio is 1: 0.5-1: 2, tower top temperature be 80-120 (℃), tower still temperature be 120-170 (℃).
The tower still temperature of No. 2 rectifying tower is relatively low, reduced the coking degree of 4-aminodiphenylamine, the 4-aminodiphenylamine that accounts for total amount 96% has separated at the cat head of No. 2 rectifying tower of relatively low tower still temperature and has made, thereby the amount of carrying out 4-aminodiphenylamine in the feed liquid of batch distillation significantly reduces.The batch still temperature be 280-330 (℃), batch distillation top temperature be 235-250 (℃), vacuum tightness is 0.09-0.098 (MPa).
No. 1 rectifying tower and No. 2 rectifying tower adopt shallow liquid layer formula vaporizer heating, and heating agent adopts high-temperature molten salt, and No. 3 the rectifying tower heating agent adopts steam, and batch distillation adopts the chuck heating, and heating agent adopts high-temperature molten salt.
4-aminodiphenylamine crude product stock liquid has reduced the residence time of stock liquid at the tower still after separating through continuous three towers, has reduced the tower still temperature of distillation finished product 4-aminodiphenylamine, has alleviated the coking degree.From No. 3 isolated aniline of rectifying tower according to processing requirement directly cover use the last operation, thereby solved aniline apply mechanically liquid contain nitrogen benzide, these two impurity of azophenlyene in reaction system because of accumulation makes product yield, degradation problem under the content.At last, No. 2 rectifying tower tower bottomss steam remaining 4-aminodiphenylamine, and return No. 2 rectifying tower rectifying through batch distillation, can improve the yield of 4-aminodiphenylamine.The content of whole technology gained 4-aminodiphenylamine is higher than 99%, and fusing point is higher than 71 ℃, and distillation yield can bring up to 99% from 94%, and aniline obtains recovery set and uses simultaneously.
Description of drawings
Accompanying drawing is the process flow sheet of the method for refining 4-amino pentanoic
1-aniline 2-azophenlyene and nitrogen benzide
3-finished product 4-aminodiphenylamine 4-contains the feed liquid of 4-aminodiphenylamine
5-cumulative tower feed liquid 6-residue
Embodiment
The crude product (containing 4-aminodiphenylamine 78.1%, aniline 20.1%, nitrogen benzide 1.1%, azophenlyene 0.7%) that will contain the 4-aminodiphenylamine enters rectifying tower with 120 kilograms/hour of flows No. 1 by the toothed gear pump successive.270 ℃ of control tower still temperature, 110 ℃ of control tower top temperatures, vacuum tightness is at 0.094MPa, reflux ratio 5: 1, light constituent aniline, nitrogen benzide, three kinds of materials of azophenlyene are from the cat head extraction, and flow is about 26.2 kilograms/hour, enter rectifying tower No. 3,150 ℃ of No. 3 rectifying Tata still temperature, 90 ℃ of tower top temperatures, vacuum tightness 0.094MPa, reflux ratio 1: 1, cat head distills out aniline for 24 kilograms/hour with flow, what the tower still was remaining is nitrogen benzide, azophenlyene, 1 rectifying tower tower bottoms enters rectifying tower No. 2, keeps 280 ℃ of tower still temperature, vacuum tightness 0.097MPa, tower top temperature is controlled at 170 ℃, reflux ratio 1: 1, and it is finished product 4-aminodiphenylamine that the cat head of No. 2 rectifying tower obtains, No. 2 the rectifying tower bottoms enters batch still, the still temperature control 285-320 (℃), vacuum tightness 0.094MPa, the top temperature remain on 235-250 (℃), boil off remaining 4-aminodiphenylamine, apply mechanically back No. 2 rectifying tower rectifying again.It is continuous that the method for refining 4-amino pentanoic of the present invention has technological process, 4-aminodiphenylamine yield height, and quality is good.It is 99.1% that above-mentioned technology obtains finished product 4-ADP amine content, and yield is 99%, 72 ℃ of the fusing points of finished product, and 72.4 ℃ at zero pour, aniline obtains reclaiming simultaneously.
Claims (6)
1, a kind of method of refining 4-amino pentanoic, it is characterized in that adopting the method for three tower continuous rectifications and batch distillation, No. 1 rectifying Tata still obtains crude product 4-aminodiphenylamine, cat head obtains aniline, No. 2 rectifying tower is used for purifying raw 4-aminodiphenylamine, No. 3 rectifying tower is used to separate aniline, and the 4-aminodiphenylamine that No. 2 tower tower bottomss of batch still batch distillation make also returns No. 2 rectifying tower and makes with extra care.
2, the method for refining 4-amino pentanoic according to claim 1, the vacuum tightness that it is characterized in that No. 1 rectifying tower is 0.09-0.098MPa, reflux ratio is 2: 1-10: 1, tower top temperature is 80-130 ℃, tower still temperature is 260-290 ℃.
3, the method for refining 4-amino pentanoic according to claim 1, the vacuum tightness that it is characterized in that No. 2 rectifying tower is 0.09-0.098MPa, reflux ratio is 1: 0.5-1: 4, tower top temperature is 140-190 ℃, tower still temperature is 260-300 ℃.
4, the method for refining 4-amino pentanoic according to claim 1, the vacuum tightness that it is characterized in that No. 3 rectifying tower is 0.09-0.098MPa, reflux ratio is 1: 0.5-1: 2, tower top temperature is 80-120 ℃, tower still temperature is 120-170 ℃.
5, the method for refining 4-amino pentanoic according to claim 1 is characterized in that batch still vacuum tightness is 0.09-0.098MPa, and tower still temperature is 280-330 ℃, and tower top temperature is 235-250 ℃.
6, the method for refining 4-amino pentanoic according to claim 1, it is characterized in that No. 1 rectifying tower and No. 2 rectifying tower adopt shallow liquid layer formula vaporizer heating, heating agent adopts high-temperature molten salt, and No. 3 rectifying tower adopts steam heating, batch distillation adopts the chuck heating, and heating agent adopts high-temperature molten salt.
Priority Applications (31)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB031481965A CN1189445C (en) | 2003-07-04 | 2003-07-04 | Method for refining 4-amino diphenylamine |
| EA200501647A EA009395B1 (en) | 2003-07-04 | 2004-07-02 | A process for preparing 4-aminodiphenylamine |
| PCT/CN2004/000734 WO2005003079A1 (en) | 2003-07-04 | 2004-07-02 | A method for producing 4-aminodiphenylamine |
| ES04738332T ES2373720T3 (en) | 2003-07-04 | 2004-07-02 | METHOD FOR THE PRODUCTION OF 4-AMINODYPHENYLAMINE. |
| DE602004010234T DE602004010234T2 (en) | 2003-07-04 | 2004-07-02 | PROCESS FOR THE PREPARATION OF 4-AMINODIPHENYLAMINE |
| ES04738331T ES2298762T3 (en) | 2003-07-04 | 2004-07-02 | PROCESS TO PREPARE 4-AMINODYPHENYLAMINE. |
| JP2006517937A JP4546958B2 (en) | 2003-07-04 | 2004-07-02 | Method for producing 4-aminodiphenylamine |
| US10/882,677 US7176333B2 (en) | 2003-07-04 | 2004-07-02 | Process for preparing 4-aminodiphenylamine |
| EP04738331A EP1591438B1 (en) | 2003-07-04 | 2004-07-02 | A process for preparing 4-aminodiphenylamine |
| KR1020040051541A KR100612922B1 (en) | 2003-07-04 | 2004-07-02 | A process for producing 4-aminodiphenylamine |
| JP2006500463A JP4500302B2 (en) | 2003-07-04 | 2004-07-02 | Method for producing 4-aminodiphenylamine |
| EA200600052A EA009396B1 (en) | 2003-07-04 | 2004-07-02 | A method for producing 4-aminodiphenylamine |
| EP04738332A EP1645555B1 (en) | 2003-07-04 | 2004-07-02 | A method for producing 4-aminodiphenylamine |
| AT04738332T ATE526305T1 (en) | 2003-07-04 | 2004-07-02 | METHOD FOR PRODUCING 4-AMINODIPHENYLAMINE |
| CA2531074A CA2531074C (en) | 2003-07-04 | 2004-07-02 | Process for preparing 4-aminodiphenylamine |
| PCT/CN2004/000733 WO2005003078A1 (en) | 2003-07-04 | 2004-07-02 | A process for preparing 4-aminodiphenylamine |
| PT04738332T PT1645555E (en) | 2003-07-04 | 2004-07-02 | A method for producing 4-aminodiphenylamine |
| CA2515238A CA2515238C (en) | 2003-07-04 | 2004-07-02 | Process for preparing 4-aminodiphenylamine |
| US10/883,042 US7084302B2 (en) | 2003-07-04 | 2004-07-02 | Process for preparing 4-aminodiphenylamine |
| MXPA05013788A MXPA05013788A (en) | 2003-07-04 | 2004-07-02 | A process for preparing 4-aminodiphenylamine. |
| BRPI0412101-5A BRPI0412101A (en) | 2003-07-04 | 2004-07-02 | process for the preparation of 4-aminodiphenylamine |
| PL04738332T PL1645555T3 (en) | 2003-07-04 | 2004-07-02 | A method for producing 4-aminodiphenylamine |
| KR1020040051932A KR100612923B1 (en) | 2003-07-04 | 2004-07-05 | A process for preparing 4-aminodiphenylamine |
| US11/477,954 US7235694B2 (en) | 2003-07-04 | 2006-06-30 | Process for preparing 4-aminodiphenylamine |
| US11/757,277 US20080039657A1 (en) | 2003-07-04 | 2007-06-01 | Process for preparing 4-aminodiphenylamine |
| US11/759,897 US8293673B2 (en) | 2003-07-04 | 2007-06-07 | Process for preparing 4-aminodiphenylamine |
| US11/759,901 US20070227675A1 (en) | 2003-07-04 | 2007-06-07 | Process for preparing 4-aminodiphenylamine |
| US12/195,371 US7989662B2 (en) | 2003-07-04 | 2008-08-20 | Process for preparing 4-aminodiphenylamine |
| US12/900,459 US8486223B2 (en) | 2003-07-04 | 2010-10-07 | Falling film evaporator |
| US13/104,900 US8686188B2 (en) | 2003-07-04 | 2011-05-10 | Process for preparing 4-aminodiphenylamine |
| US13/620,588 US9029603B2 (en) | 2003-07-04 | 2012-09-14 | Process for preparing alkylated p-phenylenediamines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB031481965A CN1189445C (en) | 2003-07-04 | 2003-07-04 | Method for refining 4-amino diphenylamine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1470499A CN1470499A (en) | 2004-01-28 |
| CN1189445C true CN1189445C (en) | 2005-02-16 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB031481965A Expired - Lifetime CN1189445C (en) | 2003-07-04 | 2003-07-04 | Method for refining 4-amino diphenylamine |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1189445C (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104529916B (en) * | 2014-12-25 | 2017-01-25 | 天津大学 | Method for separating high-purity phenazine from waste material generated in chemical product production |
-
2003
- 2003-07-04 CN CNB031481965A patent/CN1189445C/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CN1470499A (en) | 2004-01-28 |
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Address after: Room 1, building 606, medicine City Avenue, Jiangsu, Taizhou, China, 225316 Patentee after: SENNICS Co.,Ltd. Address before: 225300 Jiangsu City, Taizhou Province medicine city road, room 1, No. 212 Patentee before: Jiangsu Sinorgchem Technology Co.,Ltd. |
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Address after: 200120 China (Shanghai) free trade pilot area, Pudong Avenue, room 1200, 2304. Patentee after: SENNICS Co.,Ltd. Address before: 225316 Room 606, medicine City Avenue, Taizhou, Taizhou, Jiangsu Patentee before: SENNICS Co.,Ltd. |
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