The following is one PROPOSED timeline for the Pauline epistles:

Pre-Prison Epistles:  1 and 2 Thessalonians were written during Paul’s visit at Corinth – 54 A.D. (Acts 18:1, 5, 11; cf. I Thes 3:1-13).

1 and 2 Corinthians were penned at Ephesus where the apostle Paul resided for a period of two years – 59-60 A.D. (Acts 19:1, 8-10; cf. I Cor 15:30-34).

Romans and Galatians were the fruits of Paul’s stay at Corinth for three months – 60 A.D. (Acts 20:1-3).

Prison Epistles:  Ephesians, Philippians, Colossians, Philemon, and 1 Timothy

Ephesians was written from Rome in 64 A.D. by Paul.  Due to the apostle’s failing eyesight, he normally dictated his letters to a personal secretary.  In this particular case, Tychicus was apparently called upon for the task at hand.  We do know for certain that Tychicus carried this epistle to its final destination (Eph. 1:1 cf. 6:21).  This letter is the first of Paul’s prison epistles, which marks the division between the apostle’s early and latter ministries.

Philippians, Colossians, Philemon, and 1 Timothy were also products of the apostle Paul’s labors during his first Roman imprisonment – 64 A.D. (Acts 28:16, 29, 30; cf. Eph 6:20; Phil 1:12-19; Col 4:7-10; Philemon 1:1; 1 Tim 3:14; Phil 2:17-24).

Liberty Epistle:  Titus was probably written during Paul’s brief release from prison while he resided at Nicopolis awaiting the return of Titus from Crete – 65 A.D. (Titus 3:12).

Second Roman Imprisonment Epistle:  2 Timothy was the last epistle that Paul wrote just prior to his death at Rome – 66 A.D. (2 Tim 1:8; 4:6-9).