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Method For Producing E Caprolactam

Abstract: ABSTRACT A method of producing s-caprolactam from 3-oxoadipic acid which is preferred as a biomass resource is disclosed.  The method of producing s-caprolactam includes: the step 1 of mixing at least one selected from the group consisting of 3-oxoadipic acid and salts thereof with a catalyst and a solvent in the presence of hydrogen to produce 3-hydroxyadipic acid; and the step 2 of reacting the 3-hydroxyadipic acid which is a product of the step 1, a salt or carboxylic acid derivative thereof, or a mixture of these with hydrogen and ammonia.

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Notices, Deadlines & Correspondence

Patent Information

Application #
Filing Date
03 April 2018
Publication Number
15/2018
Publication Type
INA
Invention Field
CHEMICAL
Status
Email
Parent Application

Applicants

TORAY INDUSTRIES, INC
1-1, Nihonbashi-Muromachi 2-chome, Chuo-ku, Tokyo 103-8666, Japan.

Inventors

1. TSUKAMOTOO Daijiro
c/o Basic Research Center, Toray Industries, Inc., 10-1, Tebiro 6-chome, Kamakura-shi, Kanag aw a 248 -8555,Japan.
2. ITO, Masateru
c/o Basic Research Center, ToraYIndustries, Inc., 10-1, Tebiro 6-chome,Kamakura-shi, Kanag aw a 248 -8555,Japan.
3. YAMADA, Katsushige
c/o Basic Research Center, Toray Industries, Inc., 10-1, Tebiro 6-chome, Kamakura-shi, Kanag aw a 248 -8555, Japan.
4. YAMASHITA, Kohei
c/o Nagoya Plant, Toray Industries, Inc., 9- 1, Oe-cho, Minato-ku, Nagoya-shi, Aichi 455-8502, Japan.
5. AKAHIRA, Masato
c/o Nagoya Plant, Toray Industries, Inc., 9-1, Oe-cho, Minato-ku, Nagoya-shi,Aichi 455-8502, Japan.
6. YAMAUCHI, Koji
c/o Nagoya Plant, Toray Industries, Inc.,9-1, Oe-cho, Minato-ku, Nagoya-shi,Aichi 455-8502, Japan.

Specification

CLAIMS
1. A method of producing s-caprolactam, comprising: the step 1 of mixing at least one selected from the group consisting of 3-oxoadipic acid and salts thereof with a catalyst and a solvent in the presence of hydrogen to produce 3-hydroxyadipic acid; and the step 2 of reacting the 3-hydroxyadipic acid which is a product of the step 1, a salt or carboxylic acid derivative thereof, or a mixture of these with hydrogen and ammonia.
2. The method according to claim 1, wherein the solvent is an aqueous solvent or an organic solvent having a polarity value of 0 to 0.3.
3. The method according to claim 1 or 2, wherein the solvent is an organic solvent that mainly contains at least one selected from the group consisting of ether solvents and ester solvents.
4. The method according to any one of claims 1 to 3, wherein the solvent is an organic solvent that mainly contains at least one selected from tetrahydrofuran, dioxane, 1,2-dimethoxyethane, diglyme, and ethyl acetate.
5. The method according to any one of claims 1 to 4, wherein the step 1 is carried out under the condition of the following (i) or (ii):
(i) in an aqueous solvent at a reaction temperature of 0°C to 50°C; (ii) in an organic solvent having a polarity value of 0 to 0.3 at a reaction temperature of not lower than 0°C and lower than 75°C.
6. The method according to any one of claims 1 to 5, wherein the step 2 is carried out in the presence of a catalyst.
7. The method according to any one of claims 1 to 6, wherein the catalyst used in the step 1 and/or the step 2 comprises one or more metals selected from the group consisting of palladium, platinum, ruthenium, rhodium, rhenium, nickel, iridium, osmium, copper, and chromium.

8. The method according to claim 7, wherein the metal is supported on at least one support selected from the group consisting of alumina, carbon, silica, titania, zirconia, tantalum oxide, niobium oxide, and zeolite.
9. The method according to any one of claims 1 to 8, wherein the partial pressure of hydrogen in the step 1 and the step 2 is 0.1 MPa to 10 MPa at ordinary temperature in terms of gauge pressure.
10. The method according to any one of claims 1 to 9, wherein the reaction temperature in the step 2 is 150°C to 280°C.
11. A method of producing 3-hydroxyadipic acid, comprising mixing at least one selected from the group consisting of 3-oxoadipic acid and salts thereof with a catalyst in the presence of hydrogen under the condition of the following (i) or (ii):
(i) in an aqueous solvent at a reaction temperature of 0°C to 50°C; (ii) in an organic solvent having a polarity value of 0 to 0.3 at a reaction temperature of not lower than 0°C and lower than 75 °C.

Documents

Orders

Section Controller Decision Date

Application Documents

# Name Date
1 201847012638-TRANSLATIOIN OF PRIOIRTY DOCUMENTS ETC. [03-04-2018(online)].pdf 2018-04-03
1 201847012638-US(14)-HearingNotice-(HearingDate-02-02-2021).pdf 2021-10-17
2 201847012638-STATEMENT OF UNDERTAKING (FORM 3) [03-04-2018(online)].pdf 2018-04-03
2 201847012638-Correspondence to notify the Controller [25-01-2021(online)].pdf 2021-01-25
3 201847012638-PROOF OF RIGHT [03-04-2018(online)].pdf 2018-04-03
3 201847012638-CLAIMS [19-08-2020(online)].pdf 2020-08-19
4 201847012638-PRIORITY DOCUMENTS [03-04-2018(online)].pdf 2018-04-03
4 201847012638-FER_SER_REPLY [19-08-2020(online)].pdf 2020-08-19
5 201847012638-POWER OF AUTHORITY [03-04-2018(online)].pdf 2018-04-03
5 201847012638-FORM 3 [19-08-2020(online)].pdf 2020-08-19
6 201847012638-Information under section 8(2) [19-08-2020(online)].pdf 2020-08-19
6 201847012638-FORM 1 [03-04-2018(online)].pdf 2018-04-03
7 201847012638-OTHERS [19-08-2020(online)].pdf 2020-08-19
7 201847012638-DECLARATION OF INVENTORSHIP (FORM 5) [03-04-2018(online)].pdf 2018-04-03
8 201847012638-PETITION UNDER RULE 137 [19-08-2020(online)].pdf 2020-08-19
8 201847012638-COMPLETE SPECIFICATION [03-04-2018(online)].pdf 2018-04-03
9 201847012638-CLAIMS UNDER RULE 1 (PROVISIO) OF RULE 20 [03-04-2018(online)].pdf 2018-04-03
9 201847012638-certified copy of translation [15-07-2020(online)].pdf 2020-07-15
10 201847012638-FER.pdf 2020-02-21
10 Correspondence by Agent_Form 1_09-04-2018.pdf 2018-04-09
11 201847012638-FORM 18 [22-08-2019(online)].pdf 2019-08-22
11 201847012638-FORM 3 [04-07-2018(online)].pdf 2018-07-04
12 201847012638-FORM 18 [22-08-2019(online)].pdf 2019-08-22
12 201847012638-FORM 3 [04-07-2018(online)].pdf 2018-07-04
13 201847012638-FER.pdf 2020-02-21
13 Correspondence by Agent_Form 1_09-04-2018.pdf 2018-04-09
14 201847012638-certified copy of translation [15-07-2020(online)].pdf 2020-07-15
14 201847012638-CLAIMS UNDER RULE 1 (PROVISIO) OF RULE 20 [03-04-2018(online)].pdf 2018-04-03
15 201847012638-COMPLETE SPECIFICATION [03-04-2018(online)].pdf 2018-04-03
15 201847012638-PETITION UNDER RULE 137 [19-08-2020(online)].pdf 2020-08-19
16 201847012638-DECLARATION OF INVENTORSHIP (FORM 5) [03-04-2018(online)].pdf 2018-04-03
16 201847012638-OTHERS [19-08-2020(online)].pdf 2020-08-19
17 201847012638-FORM 1 [03-04-2018(online)].pdf 2018-04-03
17 201847012638-Information under section 8(2) [19-08-2020(online)].pdf 2020-08-19
18 201847012638-FORM 3 [19-08-2020(online)].pdf 2020-08-19
18 201847012638-POWER OF AUTHORITY [03-04-2018(online)].pdf 2018-04-03
19 201847012638-PRIORITY DOCUMENTS [03-04-2018(online)].pdf 2018-04-03
19 201847012638-FER_SER_REPLY [19-08-2020(online)].pdf 2020-08-19
20 201847012638-PROOF OF RIGHT [03-04-2018(online)].pdf 2018-04-03
20 201847012638-CLAIMS [19-08-2020(online)].pdf 2020-08-19
21 201847012638-STATEMENT OF UNDERTAKING (FORM 3) [03-04-2018(online)].pdf 2018-04-03
21 201847012638-Correspondence to notify the Controller [25-01-2021(online)].pdf 2021-01-25
22 201847012638-US(14)-HearingNotice-(HearingDate-02-02-2021).pdf 2021-10-17
22 201847012638-TRANSLATIOIN OF PRIOIRTY DOCUMENTS ETC. [03-04-2018(online)].pdf 2018-04-03

Search Strategy

1 SearchStrategyMatrix-f_18-02-2020.pdf